Category: Monocategorized

Hello everyone and welcome to 2021! I thought I would start off this year by continuing to talk about positive team-related activities. So without further ado, let’s discuss how your team can choke to death on small pebbles.

Woah… Wait… What? Let’s back it up just a little bit. Because it is January, just about everyone working for a company is about to write the end of year reviews for themselves and their subordinates. This process can take days or it can take weeks depending on who controls the budgets for compensation adjustments and just how deep into Workday your current company is invested. All of the Bidness Leadership are looking at the graphs to find the best way to capture how much Value they created and why they should be at the front of the line for the stock handouts and fat stacks of cash.

As they go through this exercise, they probably have a list of projects that were completed as well as what “moved the needle” on metrics that they can put into a Pretty Pretty Presentation to Senior Leadership.

Every place I have ever worked, I have seen these presentations and the graphs that show the numbers going up and to the right. Universally, this is how businesses grow, and also how people get rewarded.

So what is wrong with this picture?

The problem is that this puts some pretty strong incentives on making small meaningful incremental steps in your product that could lead to deeper problems in the long term.

There is significant interest in getting releases to your customers on a cadence that is measurable and also that tells a particular story for management and investors. If you happen to be working for a public company, the yardstick that everyone applies to these stories is known as the Quarterly Earnings Report. This means that every three months you are going to need to have a pretty significant nugget of data and numbers to feed to your hungry investors and shareholders.

Even if you are not a public company, you may have investors who work at venture funds, or leadership who previously worked at public companies. There is a bit of conditioning and reinforcement from those roles in expecting to hear something interesting on a drip-feed basis. I am not at all saying there is an unhealthy addiction to this schedule. Okay, maybe I am.

The problem this creates is that it puts some pretty drastic limits on what you can get approved for your engineering teams. As an engineering leader you will find that you might be put on an aggressive schedule of projects that requires a pretty fast turnover from inception to release date. If you are lucky, you might have two or more teams who can stagger the release schedule so it is more sustainable. If you are unlucky, you are going to have to take a deep breath for the brisk unending run you are about to take in your particular hamster wheel.

There are also some pretty ugly side effects to the need to do meaningful releases on a schedule like this. The first of these side effects is that you will have a shot clock on infrastructure projects. This gets more and more serious the more successful you are and the older your product becomes.

The pace of tool updates, library updates, and platform updates introduces obsolescence into your project relentlessly. I have inherited decrepit old projects that still work in production with old code in a state that you cannot even rebuild from scratch without the benefit of a hoarder’s repo of old tools.

Upgrading your software to keep it maintainable and current is a huge problem. It can also be a massive investment of time. As a result, it is likely going to be deprioritized repeatedly in favor of smaller “revenue positive” projects that will give “more bang for the buck”. Expect the person who delivers this verdict to you to wink and point finger guns at you. I don’t know why they do that.

The problem there is that if you continue operating a coal-powered locomotive in modern times, you might have difficulty obtaining coal to keep it operating, or worse, you might find that steam engine parts are only available by robbing a nearby railroad museum. Not only is this illegal, but it will make train-loving children cry.

In my head I am already reliving all of the panicked hand waving and appealing to senior leadership that I have done related to this particular situation. I am also reliving all of the times that this was taken out of the roadmap in favor of incremental revenue. Unfortunately, there are a high number of times this turned out to be a fatal mistake. It is also one of the reasons why a lot of people are nervous or afraid of experienced engineering leadership on the team. If you have fought these battles and won, the only real measurable upside is “we are still alive to keep doing this again tomorrow”. “We are still here!” is not a real compelling metric.

Also, nobody in product management understands that deferring this kind of upgrading is one of the best ways to inspire resume updating by people who you do not want to have sending out resumes. The older your product gets, the harder it is to maintain. The harder it is to maintain, the harder it is to add new things to it. The harder it is to add new things to it, the less exciting it is for people to work on it. The less exciting it is for people to work on it, the more likely the people are to leave for something more interesting to work on. It is a pretty frightening slippery slope.

So if you find yourself in this situation, what can you do about it?

The first thing you need to do is to sit down and measure the effort for each of your projects. I like to use the pebbles-to-boulders analogy here. Small projects are pebbles, medium projects are rocks, and large projects are boulders. You will find that the product roadmaps for most companies are loaded with small pebbles, and sometimes will have the intermittent rock. Very seldom do they have boulders.

What you need to do next is to point out that a slow and steady drip feed of pebble-sized projects will only ever be a constant incremental improvement over time for your business.

This means if you are in second place, you will always be in second place. You can assume most times that the people above you are there because they have a good cadence of releases and growth, and it can be sustained. That means to cover ground you are going to need to create genre-busting step functions to catch up to them and surpass them.

If you are in first place, we can assume one of two things is true. 

First, we can assume that you are more successful than your competitors at shipping new features, in which case you will continue to push pebbles into the marketplace which will slowly create a drag on your business. 

Eventually, you hit a failure-state where something has a cascading problem and your dependence of consistent pebbles being released into the marketplace will suddenly be broken which opens the door to your competitors to catch ground. In my opinion, Jira is one of the best examples of a marketplace leader who ships a lot of pebbles. We will see how that works out for them in the long run.

Second, we can alternatively assume that you are not more successful than your competitors at shipping new features, in which case you are eventually going to be surpassed by them and lose your position at the front.

Very seldom do you find a product that is far out in front and stays there. If you find yourself in that position, congratulations on getting a job at Apple.

If you are not that fortunate, then you need to figure out how to change your organization’s behavior to be more successful, and generally you will find that the companies that suffer the most from this are slowly losing their forward momentum on a small-pebble strategy.

Until you point out to them that you are choking to death on those small pebbles, you will likely struggle with getting them to agree to taking on rocks or boulders as a part of the product roadmap.

Please do not promise magic silver bullets for your first time doing this. Temper their expectations that it will take a few tries to perfect step-function changes. It is not likely that you will get it perfect right out of the gate.

Be patient with this process. It is a very difficult position to be in and it will likely be a great ‘growth opportunity’ for you. Engaging with your peers to change organizational behaviors for the better is really hard and you are likely to encounter resistance at every step of the way. I assure you that it is worth it in the long run.

If you do not want to do this or are unsuccessful at getting buy-in on performing preventative large scale maintenance, you should take a deep breath between pebbles. Eventually you will be fed enough of them that you are going to choke to death on them. Hopefully you can successfully convince enough people that it is worth doing something about those pebbles before that happens.

At any rate, if this all sounds like rubbish to you then maybe you just like to eat pebbles. See how many pebbles you can eat in a business quarter—then try to beat that record!

Thank you again for reading along. I hope you find some value here. I love comments and questions in response to my weekly articles—feedback is a gift. Failing any feedback, I will give you some more of my thoughts to consume in deep contemplative silence next week!

Now that we are rolling into the end of the year and most of you are doing holiday things, I thought I would find something a little warmer and fuzzier than normal to write about. So I am going to talk about one of the things I work hard to find with teams: Shared understanding.

Over twenty years of being involved in software development I have seen every flavor of process management. I have signed off on weekly status reports for ISO-9000 certified waterfall releases, and I have released software without a single Jira item logged against it.

Through all of these processes and philosophical arguments with people over what is and what isn’t agile, I have come to understand that different people and different industries tend to ship software effectively according to different rules.

Writing dispatch software for emergency works and 911 systems requires more deeply embedded waterfall design and structure. Making entertainment software tends to work better with shippable masters that are iterated upon using agile methodologies. I acknowledge that this is my personal experience speaking and that everyone has their own preferences for how to get stuff done.

One thing that is universally in common in all of these systems is the need for the people who design and plan for a product, and the people who build and maintain a product, to have a means of negotiation on what done means. Sometimes the things that are asked for require refinement or introduce special edge cases that need to be accounted for. Sometimes the requirements for the end product are not even possible as defined at the start.

One thing I have come to realize, through building lots of software and managing lots of teams, is that the best outcomes all had one thing in common—everyone was working to improve their shared understanding.

I am going to illustrate what that means through a badgile story. Yes I made up a word. Bad Agile equals badgile.

Once upon a time I was working on a consumer-facing website that had commerce integration. We partnered with a credit card processing company and we had a two week sprint to finish a set of tasks related to making credit card transactions work.

One of the developers picked up a task to generate a token that gets surfaced to the end user when a transaction gets approved by the credit card company.

At the end of the sprint, the developer in question demonstrated the api call and showed how entering in valid credit card information resulted in a Unique GUID that gets created and stored into the player’s account and added to his payment history.

The project owner shook his head and said “No, that is not done. This token is not human readable, I cannot approve the story.”

Record Scratch Noise… Wait What?

We stopped the meeting at this point to have a sidebar conversation. What we had here was a hidden acceptance criteria that was not communicated in the story, nor was that intent clear anywhere. On the surface, I can see the value of having a token that can be read aloud to a customer service agent over the phone, but that is extra work that was not in the scope of the original work request.

The good news is that everyone had an “aha” moment about this and we were able to declare that the work was done, and that we added a new story to modify the GUID to be human readable as the next task.

This is about the best example of a lack of shared understanding as I have ever seen, and I use it to help people understand its importance.

When I am working with new teams I do my best to try to introduce a few core concepts to help make them successful. The first and easiest is the notion of quorum, taken from multiple terms in student council while still in school and also taken cheerfully from Robert’s Rules of Order;the book that everyone loves to hate.

When I attend a meeting, I make sure that all the stakeholders are in attendance, and I am eager to ask people if we have quorum. If we do not then there is no point in starting the meeting only to regurgitate large amounts of it when all of the relevant stakeholders arrive.

The next thing that I do is teach the notion of shared understanding, which is one of the most important things I do when working with a new team.

I do not think that you can build great software as a team without shared understanding.

I also do not think you can develop shared understanding quickly without pointing out its importance.

It turns out that shared understanding is a powerful safety word for software development. I am the first to tell everyone to pump the brakes when I am confused, whereupon I will freely state “I do not think we have shared understanding here”.

It is a great way to get everyone to stop, think about what they know, and more importantly, how to communicate what they know to other people so we can all agree on the knowledge.

If you can get your teams to a point of declaring a lack of shared understanding, then suddenly the focus rapidly becomes how to communicate that understanding from the person who has it, to the person who does not.

Over time it is a beautiful process to watch. The act of declaring a lack of shared understanding helps people to refine their communication tools and to improve their ability to define and accept work.

The next time you are on a team and things are not working well, you should take a step back and ask yourself: Do we have shared understanding here?

If you do not then I suggest you declare it to all parties involved and try to figure out how to reach shared understanding together.

Thank you for reading along. This week’s article was short and sweet. I look forward to writing more articles next year, and as always I treasure your feedbackey-words, your likey-clicks, and your linkey-shares. The more social reciprocity you give me as adults, the less I will use cutesy-wutesy words to endear you to perform said activities.

There are many things I learned in my career that I could never explain to a younger version of me and expect him to accept it and understand it. Today we are going to talk about one of my favorites. We are going to talk about being right.

I was painfully right early on in my career way too often. I recall many times sitting in a room patiently waiting to say something that I knew either was true, or soon would be true. Maybe I wasn’t sitting patiently all of the time. Sometimes I would steamroll the conversation to get it out there. Regardless, even now I can feel the awkwardness of many meetings after making a powerful statement that would pour cold water over the mood of the room.

It was at least six years of being “that guy” before I started to realize it was a spectacularly unhelpful activity. About half of the time I would say something that was painfully true, and nobody wanted to acknowledge it or change it because of the size and nature of the pain. We can chalk those times up to the sunk-cost fallacy and move on. Equally frustrating were the times when I would say something horribly true and nobody at the time understood it, or agreed with it.

The downside of both of these activities is that if you are the first person to bring these things up, or are the largest source of this kind of information in your organization, it starts to rub off on you, and people will avoid you like you have cartoon stink-lines emanating from your body.

I recall being on a team creating a games publishing lineup and learning from a very experienced designer/producer how to model revenue and predict sales. We did a pretty comprehensive analysis of our competitors’ products, and projected initial revenues for our own products. My friend and I were very proud of ourselves, and decided we would share this with the rest of the company.

Our prediction was not well-received and I recall the horror and puzzlement on everyone’s faces. Part of the problem is that we predicted our own product would outsell everyone else’s products. The fact that a month later, we proved to be correct was not a soothing balm to the stinging rebuke we received organizationally. We were castigated as troublemakers from that point onwards and nobody wanted anything to do with us despite the fact that we not only gave sales projections for our products, but also gave advice to people on how to improve their products to sell better!

I think this particular case was when I hit rock-bottom. I was thoroughly confused that the two people who had the most revenue-impact on the business and had demonstrated the most knowledge and foresight were pretty much shoved into the corner to sit down and think about what we did wrong. And so we did. We sat there for a long time and neither of us could make sense of the situation.

I watched a great presentation yesterday where someone told a similar story about making logical presentations of information and having it rejected. I realized we both had a very similar epiphany moment, although she reached hers professionally way before I reached mine.

What we both learned is that sometimes people do not want to have the truth poured over them like scalding hot water—you have to weave it into a story for them to accept it as their own.

Some of you know I have a deep love of story telling. I love movies and books, and I weave much of the more interesting parts of what I watch and read into my own Dungeons & Dragons game. It took me a while to make the connective leap from from story telling for fun to storytelling for work.

It turns out that is really important. I heard in the presentation I watched yesterday that there are six stories people tell. I have read in science fiction literature that there are twelve. I ordered someone’s book yesterday to learn about six types of stories because six is easier to remember than twelve. Yes, I am that basic.

I am going to put this out there as some low-hanging fruit for you, Mr or Mrs Right: If you find yourself getting shoved into a corner because you are constantly right about things, you are going to have to figure out some new tools for helping people to understand your point if you want to rejoin the other kids in the classroom.

So let’s go over story telling and some additional tools to help you get your point across to people.

Storytelling

As someone who was a product evangelist, a part-time writer and a conference presenter, I cannot stress the value of this skill enough. You have to be able to tell a story. I have some innate storytelling abilities I have used intermittently over the years, but I believe I do not use these enough professionally. Even now I am ordering my first storytelling book because I believe I can learn to do this better and more frequently.

Consensus Building

At a previous employer, we had these meetings that people dreaded called “Architecture Reviews”. The reason they dreaded them is because people would go into the review, present a plan, and then sit there while more senior staff tore it apart in front of the whole room.

Some of the people on our team experienced slightly better success with these for one reason: They set up separate private meetings with stakeholders to review the plan up front. If you pre-sold your architecture document to senior staff, generally they would go over all of the roadblocks and speed bumps that needed to get addressed.

Many people would use the meeting as a way of getting people to look at their plan, and if it was the first time people saw it, someone would start picking at it publicly. Generally this critique is delivered by a senior staff member, which sets the tone for everyone else in the room. Everyone would suddenly sharpen their swords and find something to nitpick as a part of the festivities. If this was your architecture document, you just had a very bad time.

If you spend the time with subject matter experts privately to go over the material and explore facts, you will get a better outcome when discussing it publicly. The same goes with being right about something. Go over it with everyone in advance individually to get them to figure out options or minor course-corrections on their own time and dime. If you publicly flog them with some kind of truth, you will likely get a similar negative reaction that will take all of the wind out of your sails.

Verifiable Data

If you are struggling with getting your point across, it never hurts to appeal to authority. If you can demonstrate the validity of your data, that certainly helps your position. Making sure this is combined with the above two never hurts. Make sure it is clearly spelled out. “Do YoUr OwN rEsEaRcH” is not a good way to get people to be persuaded to accept what you are telling them. I may have been guilty of this far more than I would like to admit.

Soak Time

Bad ideas are like stubborn stains—sometimes they need to be soaked in something to be removed. Fun fact: The duration of one meeting is insufficient soak time. For anyone out there who ever sat in a meeting with me where I was furiously trying to pave over your stupidity, consider this to be a part of the apology I owe you for not giving you more time to figure out that I was trying to help you in my own horrible gaslighting way.

For small ideas, you might want to give people a day or two of soak time. For big ideas, be prepared for the window of time to be a week, or possibly even a few months.

Dark Powers

When all else fails and you really need to do the right thing, you can always throw in the towel and go crying to their manager. I will ask you to exercise caution here, because if you go to this particular font of dark power, it is a dangerous place from which to extract utility. It is addicting and all-consuming. Do this privately and gently and cautiously. I have done this a few times publicly and all it netted me was putting my name at the top of other people’s nasty little revenge books. I put this here as a last resort and something I seldom did except in extreme circumstances, and I was punished in different ways for each of them.

If you are going to someone else’s boss to rat them out for doing something dumb, just understand that it is functionally equivalent to violence, and violence is the last refuge of the incompetent. This means you are unable to solve the problem on your own and you are asking someone else to do your work for you. If you are going to go there at least sit down and write out the problem and self-soak in it for awhile so you can at least develop better tools for the future.

So there you have it! It sucks to be right, and it sucks even more to be the messenger that gets shot for communicating that. Try to develop some tools to help communicate that better to people. 

There are ways to get your point across, good and bad.

It will take some time to develop the right tools to make sure you can get people onto the same page as you, and even for me this is a work-in-progress.

So here we are at the end of today’s rambling screed of learnings. I hope you all can absorb some kind of value from the summation of these keypresses.

If you think there is someone in your life who could benefit from this message, think of how you can convey it to them without just passive-aggressively linking them to this article and saying “HEY DO YOU KNOW ANYONE WHO COULD LEARN FROM THIS” and laughing to yourself all the while—or possibly crying.

In any event, stay safe out there and give me some feedbacks. I am not yet trending on twitter, and I am not yet twerking on tiktok. I cannot decide which of those is more important for me in 2021.

So here we come into the end of 2020 and it is time to wrap up my twenty lessons in twenty years. It has been amazing to hear from the many people who have accompanied me on this journey; they have offered both feedback and encouragement for these subjects. It is hard to capture in words how much I have appreciated learning all of these things over the years, and I sincerely hope that people can use what I have written on their own quests for meaning.

If you are joining us late, here are links to the original three posts.

Without further ado, here are the last of my twenty lessons:

Choose Your Boss

I think that this is probably one of those things that you should learn earlier in your career than I did in mine. Your boss really matters for quite a lot. Your boss is more than someone who approves your expense reports and decides how many stars you get in your end of year review. Your boss ought to be considered a source of training, guidance, and experience. I will admit to having bosses I did not enjoy working with, and many I have considered great friends. When I am hiring other people, I try to market myself for what I can do for them as a boss to help them accelerate achieving their career goals. It is only recently that I realized that I never put my own early career choices through that lens.

It really matters for more reasons than I can put words to. There are a handful of people I have worked for whom I would work for again. There are a slightly larger number of people I have worked with as a peer whom I would work for as an employee. There are even a small number of people who have worked for me whom I would consider working for similarly.

If you find yourself in a situation where your boss is not helping you enough, then you should contemplate how to fix that. You should give that person the courtesy of a year if at all possible and then figure out how you can gracefully transition to something else that makes more sense for you.

Put Your People First

This is also one of those things that took too long for me to learn but I truly appreciate. You have to put your people first. I have suffered for this personally a few times over the years, but without regret. I have forsaken some promotions and tried to structure compensation and rewards according to this principle. There was one time when we were working at a struggling startup when I suggested to leadership that we offer each employee in the  company a $1000 reward for hitting a very important milestone. We jokingly called it “The Grand Bonus”.

This may not have meant much for some of our most senior people, but I will say that it made a lot of difference for our more junior team members and people in roles that were not as heavily compensated as engineering.

Quite a few people on the team realized this, and I think they worked harder to get the milestone completed for the sake of making sure everyone was rewarded.

Watching people on this project, and how they adopted a caring attitude for their team in taking this project over the finish line for the benefit of others was humbling.

There are many times I have seen people go above and beyond to help other people professionally. 

At the same struggling startup, when the end finally arrived, I spent three weeks after we closed our doors ensuring that I could do the most to help place our people into new roles and careers. That was painful for me financially as a parent; however, at the end when we had finished placing the team members into new roles I felt like a great burden was lifted. I would work with just about everyone from that team again—they were all amazing people.

The Serenity Prayer

I have commented on this before. I find myself quoting variants of the Serenity Prayer to people at work:

God, grant me the serenity to accept the things I cannot change,

courage to change the things I can,

and wisdom to know the difference.

I do not know how much more explanation that needs. Quite a few of the lessons I have learned over the years revolved around me trying to move items from one category to another. There are many times I tried to change things I could not, and many times I did not possess the serenity, or patience, to accept things that I could not change.

It is a great first-pass filter for events happening around your workplace and in fact the whole world around you too. 2020 as a whole, for example, is a master class in things we probably could not change. I am sure we are going to look back at this year for all of the things we did and scrutinize what we did with that time and how we applied serenity, courage, and wisdom to reach those outcomes.

Manage Excessive Risk

I have recently been speaking with one of my peers about their long-term career goals and how they can get there from here. Quite a bit of the road ahead of them is fraught with risk. The challenge now for them is that they will not get to take on some of that risk at their current company, nor will they get a job tackling that risk if they make a lateral move to another company.

This puts someone into a real chicken-and-egg situation. There is a solution to it, however. They are going to need to make a substantive life-change to increase the risk profile of their career.

If you are a director-level person and you want to break into your first vice president role, you might find that all the seats in your current company are taken for the next few years. There might be a clear succession already established or you might have better-qualified peers. This is one of those situations you should look at carefully for what you ought to do next.

Making the transition from one category of responsibility to another is hard. This is one of those times when it might make sense for taking a professional sidegrade. The challenge here is that you have to look at the size of the business and the size of the role accordingly. If you are too long in your current role at your current employer you might need to find a smaller company with a smaller number of existing directors and vice presidents to increase the chance you will get a viable promotion that suits your career goals.

The challenge is that this constitutes a very significant risk.

If you are only making changes to the risk you are managing at work, you are not going to accelerate your ability to transcend it. Sometimes you are going to have to take on more responsibility professionally than people will give you currently, and the only way to do that is to take a leap of faith into a new role.

This is an excessive risk; however, if you do not take excessive risk, you will not reap outsized rewards.

I am now spending some of my time with former coworkers helping them evaluate their career goals and the amount of risk they are managing. Some of these conversations are weeks old, some of these conversations are years old. In almost all of them, they are taking excessive risks to accelerate their careers.

It is terrifying to do that, honestly. I am relieved for them that they are not doing it alone, and happy to help coach them through the evaluation process and sometimes even the negotiation process that ensues.

Make Time For Little Things

The last lesson I learned that I want to leave you with is the importance of the little things. Downtime. Books. Hobbies. Cooking. Side projects.

Please make time for little things.

Writing every Sunday morning for me is one of the little things, as is a Saturday morning ritual to make a full pancake-and-eggs breakfast for the family. I make time for these things the same as I make time two nights a week for World of Warcraft raiding.

No one will force you to have a hobby or to do little things in your life for yourself or other people. You are going to have to carve out that time explicitly and just make it happen.

I am pleased that, in the most recent months, I have inspired someone to commit to writing more, as well as helped a friend build a small application that we will be publishing and talking about here in the new year.

With everything going on in the world today I picked up a small gardening hobby as well as committed to taking thirty to forty minute walks every day since I no longer commute to work.

I also explicitly make time every week to connect with someone not related to my current job. Either I am reconnecting with a former coworker or classmate, or meeting someone new on Lunch Club. Almost every single one of these meetings has been instructive or educational for me or for the other participant in some way.

Take a look at your weekly routine and if you are consumed with obligations, you should take a step back and ask yourself what you are doing for yourself, and what you are doing for your family. It is easy now, with all the electronics, to be answering emails and Slack messages around the clock. World events may have infected you with an unrealistic sense of urgency to be omnipresent professionally. I am not certain that is healthy. I have taken some mindful steps to ensure I have mental space and time for little things.

You should too.

And that wraps it up for my twenty lessons! Please share my statements of supreme obviousness on the socials, tweeter, facebake and linkum. Give me some likes, clip-claps, and stars. The more you reward me for writing, the more I will feed you. I believe this is equitable, and I hope you agree.

Thank you for reading along and I hope to engage with you in deep discussions on things to help us all be a little better every day!

So we are halfway to twenty lessons learned now, and getting into the really deep topics. I hope you are sitting down for these, possibly in possession of safety harnesses and airbags. Most of the things in today’s list are difficult to do because sometimes it feels like you are going backward while still moving forward.

Invest Time In People

Somewhere along the way you will focus less on what you are doing directly, and focus more on empowering other people to do things for you. This is the proverbial “will it scale?” meme that delights us all. It is worthwhile to empower junior developers, through creating software frameworks, providing training, or doing code reviews. Honestly, you should probably be doing all three. This is around the time that people will start to tend towards “managing people” or “managing codebases”. Do not treat this split as a set of plate-spinning exercises. If you are better at managing codebases, just focus on that. Similarly, if your chops are in people-management, then hand off maintaining the codebase to someone else. This is a great time to train up people and give them more responsibility. I generally invest some amount of my time in keeping up both sets of skills; however, you should be aware that it is okay to dive deeply into one and have other people be responsible for the other.

You should develop tools to help younger people be successful on your teams. Having talent-assessment exercises, codebase-ramping tasks, and talent-development tasks are all great things to have in your tool chest. If you are at a decade of professional software engineering experience and these words sound alien to you, you should probably take a long hard look at your five-year plan.

Do Not “Just Become Older”

This one is a favorite! I have started many companies as a bootstrapping entrepreneur. There is something exciting about that first milestone check, and eventually that final milestone check! As you build your career and your business, it is worth it to critically examine the outcome of all of your projects.

At Mofactor, my business partner and I would regularly discuss the outcomes of our projects. Sometimes we did service contracts to pay the bills, and would re-invest the margins into our own intellectual property. Of course, software development is hard, and sometimes unavoidable changes or unexpected software issues will erode those margins and we will wind up getting to the end of a project with a very thin return on investment. When we did projects that took four months or eight months and left us exactly where we started, I began to realize that the opportunity-cost of those projects were devastating. We kept the lights on during that time, sure, but also we lost significant time. I began to refer to the outcome of those projects simply as “This made us older”.

This is a powerful statement. Certainly we did not perish in the aforementioned projects—which would be bad, and that does happen—but becoming older means we are still moving forward, but we have less time. Being neutral after a project is a mild net negative and it is worthwhile to identify what things “make you older” so you can do less of them.

Always Be Recruiting 

It is time for me to give away one of my Super Secrets. Get your pens and notepads out, this is probably one worth writing down, especially if you creeped me on linkedin and found this article because I am going to be interviewing you in a few days.

I am always recruiting. I have big ideas and a large appetite to do audacious things. I have been blessed with meeting an extremely large number of talented people and I generally do a good job of helping find and fit people to their level of expertise and desired career goals. If you are in the business of making software, you should always be working towards building your ideal team. Even after people have moved on to new teams, or even new jobs, you should invest time in staying connected with them.

I spend equal amounts of time meeting new people, and maintaining connections to talented people. It is harder now than ever for me, largely due to being blessed with so many talented friends, but I still spend time maintaining it. Do not feel weird about keeping in touch with your best team members. Feel less weird about asking them to come and work with you again when you start something new.

Develop tools for recruiting as you go along. I think I waited too long to write mine down formally, but I continue to improve and refine them. Share them with other people at work. Try new things to see if you can improve them.

There are a series of questions I ask people when I am recruiting for leadership roles that help me understand if you appreciate the value of teams and your best contributors. If you are in a leadership role I will often ask you to describe the best person you ever worked with. It is interesting to see if people have just one person, or if they have many to choose from.

The follow-up question to me is equally important—I ask if they still currently talk to the best person they ever worked with. I will confess that I enjoy people’s various reactions to this question. Sometimes people realize that if they are looking for a leadership role, that this is something they did not do and ought to start. You can see it on their faces. The reaction is visceral. Sometimes people have already realized this and have an answer because they know this is important. And then, there is a third group that shrugs and does not answer the question, nor do they see its relevance. Here is that Super Secret I mentioned earlier. If you are in that third group of people, I will put this in the “areas of concern” column for me.

You should always be recruiting.

Establish Your Successors

A great follow-up to recruiting is succession planning. If you are thinking about this in the first five or six years of your career, you should probably turn off the Game of Thrones. That is probably harsher than it ought to be, but it is the rare individual who accomplishes so much in the early part of their career that they should figure out how to set up and maintain their legacy or their business.

Having a successor is important. Some people fear it, and use it as a corporate toy. Many people will have someone who is “almost there” and will keep them on standby so they do not get made redundant by their boss. There is perhaps another type of person out there who has no real clear successor and thrives on collecting a ransom from their employer for being so special and important.

I do my best to find one or two people, in each team I manage, to whom I can give the keys to the car and then walk in the other direction and know that everything will be okay. I treat this person as a peer and I generally bring them very deep into the circle of trust.

Other people you work with may resent your successor, especially if you name them as such. I really do not have a good answer for this. Too bad maybe? I just know it is important to me and it is important to the business and it is an important thing to think about.

Establishing your successor is hard, by the way. I have fucked this up royally in the past. It is possible if you have three very talented people that you want them all to have the same level of experience that they turn on each other as some sort of whacky zero-sum game. I was guilty of creating this situation exactly once, and I feel ashamed for that to this day.

It is also possible for your successor to abuse this power. Be very careful here. One time I gave someone very clear and very explicit orders and they flipped the script and said I wanted something else. This is one of those times where I will get heavy-handed. If the chain of command and communication paths do not work, then this requires a heavy role alteration and I have had to demote people for this, or worse.

It is really easy to screw this up, especially the first few times that you try it. It will hurt people’s feelings, and some people will quit their jobs because of it. It is nonetheless very important.

Let People Fail… Carefully

Phew! Where do we go after that last one right? This one is a softball. As you get farther along in your career you will be doing error-correction on your people around the clock. You will listen to them and tell them “This idea is good”, or possibly “this implementation is bad”. The shareholder value will go up more and more, the more you can redirect people towards good outcomes.

There is a problem with that though. The problem is that people won’t know how to react when the shit hits the fan.

It is important to let people follow through on bad decisions sometimes. If they do not, they will not build the tissue and muscle memory to adapt when that is needed. Also, it helps if you can identify and mitigate these failures so that it does not cause a business catastrophe.

I see this as a struggle between growing people and growing revenue. As a leader you are likely charged with balancing these two decisions. It is entirely possible you may want to get in front of every runaway freight train and just stop all of the bad ideas in their tracks. This creates learned helplessness in your team, and also prevents people from growing. Sometimes you have to let people figure things out on their own and suffer through the consequences of their own decisions.

A few times, I have sat down with people to calibrate where they are professionally and examine what they need to do in order to achieve their next career-goal or promotion. What I have found is that many of them are iterating on talents inside of a very finite box and not being stretched or given opportunities to grow out of it in the direction they want.

How do you fix that inside of an organization? The answer is: Any way you can. If you do not give those learning moments to people, or those growth opportunities, they will probably leave you for another company or another project.

You have to give people projects that make them a little uncomfortable, even if it makes you a lot uncomfortable. It is better to manage some failures on purpose than to wait for the shit to hit the fan and then have to pick up the pieces if things unravel. There are businesses that capture and institutionalize this very well. There are also businesses that bury their heads in the sand and pretend it is not important.

So there you have it, these are meaty lessons learned, and some of them still have deep, deep impact. Some of the incidents described above were horrible lessons learned and I try my best to apologize when I make mistakes that are that egregious. I truly hope that these produce a solid path through the wilderness for any of you, either now or in the future, and I look forward to wrapping this up next week!

Introduction 

This is the second of two articles co written by John and Joe.

Joe is an Investor with the early-stage seed-fund Coast to Crest. He is a startup founder with two successful exits who turned his attention to community building, starting a biotech incubator and running a startup accelerator program for 5 years. He also is a consultant who works with  growth-stage companies transitioning from startup to scaleup.  He has worked with hundreds of early-stage founders. You can read more of Joe’s writings on Medium.

John is the CTO of a startup building blockchain games and a veteran engineering leader with over two decades of startup and games industry experience. He is blogging for educational and therapeutic reasons at https://www.mofactor.com and soon hopes to announce what he is working on full time.

Why did we write this article?

John: 

I recently met with a first-time entrepreneur about to go raise money for the first time. It sent me on a wild roller coaster ride reliving experiences from over a decade ago. There is so much I wanted to say and only had a half hour or so to spare. I made them some quick introductions, including to Joe, to offer some additional thoughts about what they should be doing. At that moment I realized that, for a lot of people, raising money for their business is something they see in the news and hear about, and they do not fully understand the process. Much like our mentorship article, Joe and I decided to work on another shared article to help illuminate the process a little.

Raising funds

John:

So I have been on the management teams of companies that have gone through tremendous sums of investment money to try to do many, many different things. I have also attempted to raise money as a business founder a few times with less success. Given the amount of PR by companies raising rounds, and the number of people who I was spending time with at various tradeshows and in professional settings, it seemed like it would be an easy thing to do.

I am going to talk about why I did not raise money as a first-time fundraising entrepreneur and hopefully provide some transparency that surrounds the process.

Joe:

I founded a company that did NOT raise money, but was on the ‘other side of the table’ for my game company; we invested in startup indie game studios as a publisher. I also raised money for my accelerator program and my seed fund. I can provide insight into what I was looking for to fund (or not fund) a potential company, as well as techniques I used to raise money. 

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Why should you raise money?

John:

Building amazing things takes audacity. Just about anyone can build anything. That does not make a successful business. Generally, building an amazing thing and a successful business takes audacity… and investment capital.

There are a lot of reasons to raise money, and I was trying to raise the wrong kind of money right out of the gate; I wanted the wrong amount, and I needed it to solve the wrong problems. Because I was surrounded by people in silicon valley trying to raise millions of dollars of venture capital to do crazy things, I figured I would just jump in alongside them and do the same. I re-read some of my old pitch decks with more than a little regret, because I was clearly making a lot of rookie mistakes along the way.

So why should you raise money?

You should raise money to reduce risk. The type of risk you are reducing and the capital available to help you should generally be aligned. I was asking a lot of investors for a small investment round to help me build out a product to prove an idea. The people I was asking were always gently encouraging but almost never told me that I was going about it backwards. I would have been better off finding a few angel investors, or continuing bootstrapping, rather than distracting myself to ask for the wrong kind of money to reduce the technology risk.

Venture capital generally comes in at a later stage in a company’s life cycle. It did not really matter that we had a decent revenue pipeline and were profitable as a game studio. We wanted to do a crazy and risky platform to go direct-to-consumer in the carrier-centric world of 2005. Regardless of how good the idea was, and how the plan would have worked, no one I was asking was going to write our team a check for the amount we were asking to solve the problem we had.

Joe:

I am going to first state the main reason I choose not to invest, and that is the ‘validation’ problem. Too many entrepreneurs are looking for an investor to validate their idea as ‘worthy’ by agreeing to invest. Startups founders are often on the hunt for traction—attempting to see if their idea has merit. Getting investment is a shortcut to the process of having the product validated by the market.

Why raise money? Big things take resources. If the idea and its execution are good, then it is all about time. You could bootstrap, but it might take years to get to a scale that makes a significant impact. By the time this happens, the opportunity may have passed or a competitor may have surpassed you. If the idea is solid and the execution against that idea is working, it is time to exchange future value for present resources in order to make it happen quickly.

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When should you raise money?

John: 

It might sound trite but the worst time to raise money is when you need it. The best time to raise money is when you are about to embark on a structural change in your business that will be a significant step-function increase in its value.

You can try to raise speculative money on how successful you will be before you get the product live, which is where the most aggressive investors will want to be, or you can prove out the business and completely de-risk it which makes it a more clearly definable bank transaction. I have seen both of these investment rounds. Generally the more mature your business, the more it looks like the latter.

The amount of money you want to raise is also significant. Raising modest angel money should be started earlier in the process, compared to raising large tranches of B and C rounds later in the process. Your current series A and B investors will also participate in the timing and raising of later rounds.

Joe:

When to raise money is an interesting question, as there is no right answer. It depends on the industry, location, and team. That being said, generally the best time to raise money is when you are convinced there is a real opportunity there. If you are casting about for a market and think there is an opportunity there, you will probably not have much luck. In order to convince others, you need to be really convinced yourself and be ‘all in’ on the opportunity.

The process of starting raising money should start early. Raising money takes time, and the relationship that leads to investment should start as early in the process of your startup journey as possible. If an investor invests, they know that it is going to be an 8-10 year relationship.  Entering into such a relationship usually does not happen at the first meeting/conversation. 

How much to raise is also important. You need to raise enough to get to the next meaningful milestone. I also tell founders that the best size of a round is one you can close. You have a plan, but there is a back-and-forth in the fundraising process where the plan needs to adjust to the amount of funding you can close. Appetite for investment needs to be measured. You do this by having conversations with investors.  

It is never too early to start, but from the start of a conversation to a closed round could be a long time. Stay lean during this process and make sure that you can keep your operations running for six months or more. 

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Why won’t people give me money?

John: 

If you have glaring holes in your plans, team, or leadership, no one will invest in your business. Quite often most of them might see nuggets of potential and they will not directly say no to your face. This drives me up the wall. Most “no thank you” replies will be phrased as “let’s see where you are in two months”. Another reason people won’t give you money is you are asking for the wrong amount, or asking the wrong people. Quite possibly you might also be asking at the wrong time. Maybe you are doing all three.

In 2005, asking for 3 million dollars as a series A investment for a 50% services-based profitable studio was a bad idea. We should have put together a 500k angel round with specific milestones to prove out our new business, or else figured out how to ask for 6 million dollars for marketing and growth after figuring out how to fund the product ourselves. We could have increased the amount of recurring revenue we were generating on non-service-based product sales, or else found a few juicier service contracts with better margins. We went out and asked the wrong people on top of asking for the wrong amount.

Joe:

The answer is in the question. Investors exist to invest money, not give it away. I would say that 50% of startups I meet with use the term ‘give’ and it is a big turnoff. They are looking to raise money because they need or want money. As a founder myself, I get it. As an investor, the founder needs to understand that my goal is to take money and turn it into more money. I am not there to ‘give’ people money. It is not a gift. When a founder asks for someone to give them money, it is like asking for someone to give them a cookie. One cookie leads to a second cookie and more cookies until there are no more cookies. 

There is ‘what you think you need’, and there is ‘the right amount’ that, if deployed, will turn that money into more money.  

Too much money too early can create problems. There is the old adage “work expands to fill all available time”. Money buys time. More money makes more time available, and the amount of work will expand to consume all of it. My job is to figure out not how much you want, but how much you actually need. If we can agree on that number, then it might be a good investment. 

You have an idea. You need a plan. The idea might be good, but a clear plan that executes on that idea is necessary. Yes, the plan is probably not 100% correct (it is probably completely wrong), but there needs to be at least an initial list of needed resources in order to execute on the idea. This is usually a list of people, some activities that need to be done, and some initial guesses at the scope of the work. If the guess does not seem wildly off the mark, you may have a good shot at getting investment.  

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Why will people give me money?

John:

There are a handful of reasons why people want to invest in you. Largely they see a potential for you to give them a desired rate of return for the dollars they invest.

The four or five other factors after this include:

Location – Some funds like to invest in specific geographies. I have heard that talking to specific Sand Hill Road investors would be a waste of my time even from the Davis California area because some investors want to have a short drive to their portfolio companies. Some funds are specialized around cities or states also as a part of economic growth programs.

Business Focus – Some funds also possess an investment thesis. They believe in a particular market segment and are focusing their investments into these areas to establish synergy and to leverage expertise amongst their partners and their portfolio of companies.

The “right stuff” – When you go and ask for money the three basic requirements most people look for are:

The right idea

The right team

The right strategy

If you are two out of three, that is not necessarily a complete show stopper but then it will boil down to the investor figuring out if they have the time, energy, resources, or network to help get you to three out of three. Unfortunately for me, in 2005, when I was first raising money I did not have the right strategy. I had a mostly solid team, and a reasonably good idea. That was not enough. We had a pretty solid commitment from a marketing leader to join us after fundraising to help close the team gap, but too much of what we wanted to raise would have been spent on product development. That translates as pure market risk. Unfortunately that is not a very popular thing for venture capital investors.

Joe:

An investor will invest in, 

A clearly articulated idea, 

That solves a customer problem

In a market that is large enough to matter 

And

In a market that the founder understands (and the investor understands)

And

Has created a team that has some of the skills to start (that the investor can determine based on their experience in that market)

And

A clear plan with a clear price tag to enact that plan on a timeline that seems reasonable (based on knowledge of others doing work in that sector)

For an amount that , if successful, will generate returns in excess of the next person to walk through the door. (based on similar investments in that area of focus).

The order of risk reduction from smallest to largest is:

Reduce management risk, reduce technical risk, and finally reduce capital risk.

For early stage companies, the first thing that gets looked at is the team.  Does this team make sense to solve this problem? Have they done a startup before?  Do they understand the work that is ahead of them?  When I am assessing a team, my #1 criteria is ‘are they coachable’.  If a founder is not coachable they will not get investment.   

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Final thoughts:

John:

While I was out smashing through walls as a bootstrapping entrepreneur and building tight-knit teams that could create amazing products, that was not enough for me to level-up the business alone. Even taking on a technical co-founder, we did not de-risk our business enough, nor did we come up with a compelling enough strategy to get an investor to come on board.

Our plan at the time was to spend a few million dollars in building a high-end action RPG game that we would launch on only the best of next generation mobile phones, since we predicted there would be a must-have smartphone arriving in 2007 to 2008. A few years later after failing to raise money for this, that phone did arrive in the form of the iPhone. There were a lot of things we could have done differently to be prepared to launch compelling platform-defining content at just the right time. There were probably a lot of things we could have done differently to get one or more investors on board to make that journey less risky along the way.

Joe:

It is tough to add final thoughts as I feel we have just scratched the surface. My best advice for those starting the process is to focus on the long term. Many founders are focused on what they need right now. The short term immediate focus can be dangerous as it can leave you in no man’s land. If you are doing a cross-country trip, it is not a great idea to travel from gas station to gas station putting $5 in the tank. You can’t fill up for the entire trip, but you are better served to assume, and plan for, the probability that you will need gas during the journey. You should choose a path where there are gas stations along the way and for certain sections of the trip, plan to have enough gas just to get to the next one. You don’t want to be in Death Valley and out of gas.  

Having been a founder, I know now how long and arduous the journey can be. Back then, I was living very much in the ‘now’. I focused on what I needed then. I was not thinking from the perspective of the investor, which is longer term and focused on turning their investment money into a larger pool of money. You need to get out of the founder bubble and think of the needs of your investor, which are aligned with your needs, but different. My final thought and best advice: If your goal is to make your investor successful, you will fare better when you go out to raise. 

Good morning and hello! It is time for part two of my four part journey through twenty years of hard-learned lessons.

I have tried to group them loosely into four sections that each cover five-year chunks of my career. The first set of five lessons was mostly stuff I learned while I was still feeling invincible, and could code my way out of any problem. This next set of lessons is stuff that I was learning while slowly realizing that maybe I should consider approaching my problems differently.

So let’s jump in!

Lesson the sixth: Test Your Limits.

I think that most of us spend some time in our early adult life breaking the rules and testing our limits. It is a badge of honor for many to pull your first all-nighter. We all want to know how far we can push ourselves until we break.

The younger you are, the easier this is. After five years, this gets harder. I recall having a few project deadlines with branded partners that all managed to get delayed into one horrible week where everything was due at once. Everyone involved knew that I was a victim of unfortunate events. They were all sympathetic. They all needed their stuff completed and shipping regardless of all of that. I literally spent the whole week alternating between drinking coffee and Pepto Bismol, straight from the bottle. I managed to get through it all in one piece, but I had to take some time to recover.

The older you get, the less likely you can do this. You should know what your limits are at all times. By figuring out what changed from the time you were working all night in college to what it is like five years later, you will realize that the Reaper will be waiting at the blurry edges of your vision more and more often the harder you try to push yourself. Know what you are capable of doing when push comes to shove. You should also know that every time you do push those limits, Mister Reaper likes to sneak closer.

Lesson the seventh: Be Ready To Walk Away

One of the first contracts I ever signed was this twenty page beast that I barely understood. I would like to think that I had a great time working with that publishing company, and I did a lot of very unusual things for them for not very much money. Around that time I also was adding a child to my family. I was nervous as we were coming to the end of a long term contract and I was about to go into economic freefall. I continually brought this up regularly with the publisher during the last month of our agreement, and I was incredibly worried because there was almost no talk about contract extension or renewal.

Around that time, they had a competitor entering the marketplace. A friend of mine was working there and was able to get me an introduction. It was clear that I could give them an edge in shipping content faster, and I nervously entered conversations with them that led to an agreement that was financially twice as generous as the first company. On the one hand I knew they were taking a cheap shot at the incumbent. On the other hand, I have bills to pay.

Finally it came down to the final week of my agreement with the original company. We got on the phone and they laid out an embarrassing lowball offer. I remember being silent because it was a pay cut, for a longer agreement, and I felt pretty horrified considering my wife was expecting.

After a few moments of stunned silence I was asked point blank:

“Look, do you want to be in business with us or not?”

That one sentence and its exasperated delivery haunts me to this day.

I don’t even remember the rest of the conversation, honestly. I don’t think I was angry. I don’t think I said anything significant. I just know I took the competitor’s offer.

I know this angered them more than a little. I learned at that point the value in having a BATNA in hand. If you don’t know what that word means, you should look it up.

Sometimes you will reach a point in your negotiations or conversations with people where the only thing you can do is walk away.

Lesson the eighth: It Never Hurts To Ask For A Meeting

When someone makes an announcement that they are starting a company, or that they are making a significant career change, it does not hurt to ask to meet. Some of the best things that happened to me in my life happened simply because I asked for a meeting.

Do not be afraid to leverage your networks to get an introduction. In my entire career I can only think of one time that I was ever explicitly rebuffed by someone when I asked for an intro.

Yes, that person’s name went down in my little book. No, karma has not caught up with them yet.

Most people are willing to invest forty five minutes to an hour of their time if it makes sense. Sometimes simply asking and providing a reason are all you need for it to make sense.

Lesson the ninth: Do Not Trade Sideways

This is one of those places where I almost want to hashtag some people to offer testimony to this lesson. Almost.

I have observed when I interview people that half of the people interested in a new job are not at all interested in the new job. They are running away from their old job. 

If you are going to change jobs, do not run away from it. Bide your time. Find an upgrade. It is out there. You can thank me for it later. If you are running away from your old job, it will catch up with you. Every job will suddenly feel like you need to run away from it and you will treat hard challenges with learned helplessness. Instead of trying to figure out how to battle through your problems, you can take a 10% salary increase, a cooler title, and a new flavor of sparkling water. It can get addicting after a period of time, and then suddenly everyone will look at your resume and all they will see is a hamster spinning in a wheel. I own that resume, and I have looked at other people’s version of that resume in equal measure.

I can assure you it is quite unattractive.

In the first ten years of your career you should be pushing for growth and new responsibilities. I assure that there will always be someone who needs smart people to solve problems who is willing to take a chance on you if you can show them you are intelligent, curious, and ambitious.

Seek these opportunities out. Take them when they present themselves. Please do not trade sideways.

Also, keep in mind this advice is in the second bucket of five-year lessons. There will come a time when you have hit a ceiling in growth and all you can do is trade sideways. The longer you can postpone that day, the better off you will be.

Lesson the tenth: Measure Your Sacrifices

I have five children, and I am the sole financial provider for my family. I always promised my wife that I would keep a roof over our heads, and that we would have solid medical insurance. I have been pretty good about keeping up on that for the entirety of my children’s lives, but not without cost.

I have had to make some terrible decisions to protect my family and to keep those promises to them over the years. Sometimes it involved burning a bridge with someone I really enjoyed working with. Sometimes it involved walking away from an opportunity with a lot of upside.

There are times when that was leveraged against me, where people believed that I would turn tail and sign something or amend an agreement simply because I had no recourse or leverage. I have done my best to have a BATNA in hand for the times that I felt that was about to happen. There is a pattern that repeats itself when people are about to turn ugly. I have also done my best to ensure I knew how far I could stretch myself in the short term to ensure I can crash the cargo-plane of my career and ensure my family lives through it.

Over the years I have been blessed by getting to work with a number of people who have observed some of those sacrifices, and have also observed the mark that those sacrifices have left on me. I know some of them read along regularly. I appreciate that more than I can put into any kind of words.

As you build your career, and possibly build a family alongside it, you will have to make horrible choices along the way. This is not some “woe is me” bullshit. I knew what I was getting myself into. In California, the how-much-is-your-rent speedway is run by a DINK (Dual Income No Kids) pace car. It is relentless, has passive income, and it vacations frequently in Europe.

I have foamed at the mouth elsewhere about the cost of living in California, and the talent diaspora that is becoming more real every day. I am now past the point of feeling any shame when someone asks me why I do not own a house yet. I no longer blink when I point out that twenty years of early-stage innovation without a liquidity event in California have not let me join the monocle-eyed cloud-people club of land-owner weathiness. I knew that when I signed up. I still know it now.

Be prepared for the day when you have to make those sacrifices. Also be aware that not everyone you work with will sympathize with them. Some people will be angry with you for your choices. As circumstances have permitted, I have mended as many of those fences as I could.

Do your best to feel sorry about the situation if they do not understand your sacrifices.

Do your best to avoid them if they bear malice despite understanding your sacrifices.

Stay tuned for part three in two weeks. Next week I am taking a hiatus from baring my soul to you all, in order to publish a second shared article!

Have a great turkey week!

Last year I sat down and realized that in 2020 it will have been twenty years since I started doing professional games development. So what better time to reflect on the “20/20 hindsight” lessons of 20 years than to do it in 2020? Surely the fine folks at GDC would not say no to such a cleverly titled session… Would they? Maybe let’s change the subject.

So here are my thoughts from twenty years in the games industry. I am going to write this in four parts since this is a considerable buffet of trauma and “learnings”. I don’t know that you could stomach it all in one sitting. I am not sure I could write it in one sitting either, honestly. So let’s talk about the first five years of my career and things I ought to have learned.

Lesson the first: Don’t Just Sign It.

Whether it is a non-disclosure agreement, a work-for-hire agreement, or an employment contract, it is important to understand what you are signing. Some states and some countries, like Canada for example, enforce variations on non-compete clauses. That would be a tragic way to lose out on exercising lucrative employee stock options as I may have accidentally discovered. Setting aside the fact that I would have made the most amount of money on stocks from my first official job, it takes my feral equity negotiations with startups to the next level knowing that I had a multi-million dollar paper loss the first time out of the gate. Just about every other piece of equity I have had has gone to nearly zero or precisely zero since then, but that does not stop old people from buying lottery tickets when they go to get their White Claw and Marlboro menthols on their way to bingo night, does it?

I have to give a shout-out to the small handful of great corporate attorneys I have had over the years. I do not regret a penny I have ever spent on a lawyer and in some cases I paid extra to have them sit down and explain to me what it is that they are bickering about. As a result, I have enough of an understanding of what goes into a legal agreement that I can sign most of them without need of writing a check, and in a few cases, have taken expensive attorneys to the mat on issues I care about. I am grateful for the education I received in the process of working with some of the best startup attorneys in the world. I wish I would have had that benefit when I flipped a coin and decided to arbitrarily quit my first job ever, seemingly for no good reason.

Lesson the second: Let The Dough Rise.

It is no less than the esteemed Trip Hawkins, the founder of EA, who counseled me after I handed in my first resignation at Digital Chocolate that “You need to let your success catch up with you”. I had no idea what the hell he was talking about at the time. I understand it a little better now.

Early on in my career, I made a silent one way contract with every employer I had. “You have exactly one year to prove to me I am not wasting my time here” was the ultimatum I harbored in my soul. Perhaps it was a toxic overreaction to the one year vesting cliff; If I have one year to prove myself to you, then you have one year to prove yourself to me. Early on I enjoyed the defiance of Hammurabi’s inflexible eye-for-an-eye wisdom in many of my professional decisions. We can let the consequences of zero-sum-game thinking be debated at a later date. What I did learn from this, eventually, is that one year is nowhere near enough time to invest in a career choice. The skipping stone trash heap of entries on my resume and the scrutiny I get for latter-year career conversations on leadership roles is a dance I must make frequently. I caution you that that is a regret you would best avoid. When you make a career-choice to join a company, you will be better off if you stick around for three to five years. Seven if you can stomach it.

Lesson the third: Deal With It.

I remember going to a meeting with a business development person who would later on become a mentor of sorts for me as we gallivanted around the globe. I was given a product demo for an unsellable pile of garbage. I proceeded to dismantle it, point for point, as to why no one would want to buy it.

After shredding it to pieces and standing defiantly over its defeated corpse, I was not expecting his next question.

“Would you like to come work here with me?”

Learning how to sell things and the art of making a deal was probably one of the best early wins in my career as a software developer. I had a pretty myopic view of the value chain, and this was something that was transformative for me.

It does not matter if you make the best thing ever. If you do not know how to sell it, no one will know. I am grateful that I spent the time outside of formal engineering amongst a team of hardcore old skool enterprise sales people. I learned so much from them that reverberated through the course of my career.

I profoundly recall the advice that my soon-to-be manager would give me upon handing me an offer letter.

“Before you sign this letter, go watch Glengarry Glenross.”

So I did. And if you have not seen it, you should. It is a powerful piece of film.

Lesson the fourth: The Five Year Plan.

If you made it this far, you are probably halfway through a box of kleenex, a cup of chamomile tea, or a tub of chocolate ice cream. Maybe all three. Or maybe I glossed over the trauma that was experienced from the journeys described above. Or maybe I have forgotten it. There is photographic evidence of me being detained in a foreign country without having the right entry papers to give a presentation on multiplayer technology: I am in possession of an ear infection at the time, a not-quite-sober boss who is about to go to prison with me, and a belt that 96 hours previous to that had three thousand dollars of emergency cash money. We will not speak of what happened to it. I assure you, gentle reader, we all survived, with our freedom.

Instead, let’s talk about something more exciting: Career planning. Always have a plan. I know that is very ‘A-team’.

Fairly early on in my career, I decided it was a good idea to have a plan. After a few iterations of “I will figure out what to do after I sober up”, I realized I needed to set my sights a little higher and my view a little farther. Eventually I settled on having a five year plan as the right length. If you have read everything above you might correctly conclude that I was never able to get to the five year mark on the majority of my plans. Indeed I am pretty sure that I failed at almost all of them. The truth is that I always change my five year plan every three years. I assure you this is okay. If I ever become your boss, I will work with you on a five year plan. It is a good thing to have. If you cannot come up with one on your own I will give you one. Just understand that if I give you a five year plan, it is a part of my five year plan. You might want to ask me how long ago I came up with it. Keep me honest.

Lesson the fifth: Understand Your Passions.

I did a little zigging and zagging in and out of games in some tumultuous years. The games industry is cruel to people who have a “high cost structure”. HR does not like it when you refer to your “high cost structure” as “families”. I guess in California it is not an okay thing to tell someone “I cannot hire you because you have kids” but that is what they are saying by keeping the salary so low that they can give you a bucket of “ blah blah blah culture fit” as they walk you to the exit.

Always try to work on something that inspires you. I say this with a bit of caution. I got into game development because I loved playing games. It turns out that if you really love playing games, becoming a game developer is the last thing you want to do. You will likely never work as hard, for less money, than as a game developer. There is a lot of supply and demand economics at work that keep the wage claims low. There is always someone willing to do your job for ten percent less money because making games must be as fun as playing games.

Now that I have seen the truth I still care deeply about making games, but mostly because I found that it is something I love much more than playing them. Whenever I try a game now I find myself evaluating the experience as if I was watching the experience through a one way mirror. The instant I find structural flaws in the experience and I can map it to the deadline they were rushing to hit, I am done with the game. I add my learnings to my little notebook of “things to do” or more likely “things not to do” in my own projects.

I am passionate about a handful of things in work. I can emotionlessly perform at a high level for things I am not passionate about, provided I am putting danger-pay in the bank to buy future-me some time to get back to my passions. That creeps people out by the way. If you cannot check the “this is my passion” box, people think you are a weirdo, and they probably won’t want to pay you without a more in-depth explanation.

I will leave a list of John Szeder’s Four Passions off of this article out of self-preservation, in the unlikely event some future hiring manager uses this article against me. You might find it in the Young Adult Fiction section someday.

Stay tuned next week for lessons six through ten!

Introduction

This is the first of a couple co-written articles by Joe Maruschak and John Szeder.

Joe is an Investor with the early-stage seed-fund Coast to Crest. He is a startup founder with two successful exits who turned his attention to community building, starting a biotech incubator and running a startup accelerator program for 5 years. He also is a consultant who works with  growth-stage companies transitioning from startup to scaleup.  He has worked with hundreds of early-stage founders. You can read more of Joe’s writings on Medium.

John is the CTO of a startup building blockchain games and a veteran engineering leader with over two decades of startup and games industry experience. He is blogging for educational and therapeutic reasons at https://www.mofactor.com and soon hopes to announce what he is working on full time.

We both have had experience mentoring startup founders and employees we have worked with, and through our discussions on the challenges of mentoring and how it relates to the growth of companies, we thought it would be useful to get some of our collected thoughts out there in the hopes it might help.

What is mentoring?

John:

At some point in your career you will have checked off a considerable number, if not all, of the professional accomplishments you wish to attain on your work bucket-list. While you are on your way towards that goal you will achieve a level of fluency with your chosen profession that lets you take a step back from your work and ask yourself “how does this compare to other people?”

If you find yourself in this position, and you have given some people some guidance to help increase their level of fluency with work, then congratulations! You have exercised mentorship!

To me, mentoring is providing some of your experience to other people in a format that lets them benefit from your mistakes.

Joe:

I found this great definition online:

“Mentoring is to support and encourage people to manage their own learning in order that they may maximise their potential, develop their skills, improve their performance, and become the person they want to be.”

I picked that definition because it has some key concepts that I like. Key to this is that mentoring is the process of assisting someone to manage their own growth. It is not the job of a mentor to teach you like a high school teacher would.  The goal of a mentor is to guide you as you do what you need to do to grow. 

A mentor’s job is not to set a goal for you or give you direction. A mentor’s job is to guide you in the direction you set for yourself.  Much of the work is a look inward; a guided tour of self-discovery.  A mentor holds up the mirror so you can accurately see yourself. 

As part of this process, a skilled mentor can give you tasks and projects that help you develop skills that you may need on your journey. The mentor can teach a technique, and critique the practice, acting as a coach.  

In this way the mentor can help a person unlock what is already within them in order to discover things about themselves they did not know and enable them to do things they did not yet know they were capable of. 

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Why Mentor?

John:

I have had a few conversations with executive-level people who bootstrapped their way to success. Most of us never had a mentor and we made a lot of mistakes along the way. I find that is one of the biggest reasons I mentor people. One of the struggles as a technical leader is this strange dichotomy with keeping product-development flowing and reducing technical debt at a reasonable rate at the same time as working on succession and giving people room enough to fail at things in order to grow professionally. Mentorship helps to provide some of the growth people need if you can find the right structure and format to impart the things you learned to them, often the hard way.

I find mentorship to be one of the most important things to do when I am in an executive role, or senior leadership role on a team. I often mentor people directly outside of my organization as well; sometimes as a part-time recruiting activity, and sometimes to help make sure that what I am doing to mentor people is effective when the table-stakes do not include how they are measured in their end-of-year bonus.

Setting aside all of those reasons, I also do it because I think it is a decent thing to help people grow, and it feels good when it works.

Joe:

Not to get too ‘meta’, but I think that the world is a better place when everyone is functioning and living their life to the fullest of their potential. When you encounter someone who is excited to ‘make a dent in the universe’, there is a moral obligation to assist in achieving that if you are able to help. 

As a species, I think that unlocking our potential is the highest form of what it means to be human.  As it relates to what I do, which is helping people build companies, it often means helping people learn how to inspire and focus others on a common shared goal.  Working with others to create outcomes that would be impossible alone is an amazing thing to experience. It is empowering to do it; it is doubly empowering to be able to help others learn how to do it.

Personally, it is out of profound empathy for others that I mentor.  I spent the first half of my life feeling a bit lost. It was only after I started a company that I felt like I had found my calling. I see the struggle in others, and when I can help them to stop struggling and point them on the way toward where they would ultimately arrive, I feel compelled to do it.  There are many who go through life and wind up at the end feeling that their life was somehow half-lived. If I can empower a few to explore and experience it fully, then I feel that I have done some good, and in some way earned a chance at redemption for the sins I have committed. 

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How can you find a Mentor?

John:

There are a few different ways to find a mentor. Some companies have created internal formal mentoring programs. There are many reasons to create a formal mentoring program for a company; from succession to retention to trying to break apart tribal knowledge clusters. Finding a company which has a mentoring program will be hit or miss.

In addition to formal mentoring, you can also find an informal mentor. Maybe it is someone you worked with in the past or want to work with in the future. I have a long view on recruiting and sometimes I connect with people I do not immediately hire for whatever reason. I have informally mentored some of them over the years with the hope that our paths may someday cross.

You might meet a mentor giving a presentation on something interesting at a tradeshow. I recently joined a service called LunchClub and it is likely at least one of the people I met there is someone I will wind up mentoring.

Joe:

It starts with a decision to grow. When you are ready to get real and improve, it is the right time. If the goal is just career-advancement and the focus is transactional and the goal is part of a corporate-ladder-climbing exercise, your success will be limited and any mentor you get may not be able to help you much.  When you are ready to REALLY grow as a person and unlock the potential within, it will be obvious and good mentors will be very open to working with you.

The best way to find a mentor is to seek out someone who models who you want to be.  You see someone who seems to effortlessly solve a problem that you could not solve, or one who goes into a meeting and gets the outcome you could not seem to get.  You think to yourself “How were THEY able to do that?”  When you see in them a vision of what you think your future-self could be, you may have found your mentor. 

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How can you find a Mentee?

John: 

If you are a mentor, and looking for mentees, just look around you. The world is filled with promising young people who may or may not be outright asking for guidance or assistance, but certainly would benefit from it.

The previously-mentioned Lunchclub would be a good way, or just reach out to someone who is writing interesting articles on the internet or has a commanding social media presence. Start by asking questions and being appreciative of their help and answers.

Joe:

Open your eyes and look around.  Potential mentees are everywhere.  Be open to entering into a relationship as a guide.  A mentor/mentee relationship is two-way.  You often learn as much as the mentee from the process.  Along the path to being a better leader, first you lead, then you teach others to lead, and then you teach others to teach others to lead.  It is a never-ending ‘leveling up’  and it takes practice and to keep sharp; you need to keep doing it all the time. It is also a test of the mentor.  A good mentor never stops growing or learning, so as a mentor looking for a mentee you need to be aware of your own growth, your own path and challenges, and seek out situations and relationships that will challenge you to help you grow.

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What do you do as a Mentor?

John: 

I accidentally started mentoring the first engineer I ever hired. It was a young student who was looking for a games-industry summer job, and my little one-man shop happened to be the only game studio around. I was boot-strapping at the time, and while I found him to be very impressive, I felt a little guilty that I could barely afford to pay him anything. Accordingly, I thought it would be a good idea for me to include, as a part of his daily schedule, some time where I essentially just teach him things about what work means and how I was functioning as a developing business owner; things that I was pretty certain he was not learning in engineering college.

The student in question professionally flourished over the next decade. I feel that his success was greatly increased through the mentorship he received, and it inspired me to provide that to people.

I never really thought about it at the time, but some time in the intervening years I got to the point where I set up formal 1:1 meetings with people on a weekly, biweekly, monthly, or quarterly basis to meet and either give them a long-winded bloviating sermon about something on my mind, or else I let them ask free-form questions.

Sometimes people are looking for specific mentoring help, in which case it makes sense to set up something that is more goals-oriented and maybe includes a little bit of homework between meetings.

At the end of the day I find that mentoring is a bit of talking, a lot of thinking, and much, much more listening.

Joe:

I ask a lot of questions. Being a mentor is being a guide to someone discovering themselves. It is my job to hold up the mirror so they can more clearly see themselves, and to ask questions that encourage them to think more deeply. 

When I mentor I try to be very careful not to give the answers, but to ask the right questions. The process of discovering the answer is up to the mentee.  This is important to me. To give someone the answer takes away their agency, and having agency is important to the process of knowing oneself and developing personal leadership—the first step in becoming a leader.

I often use metaphors to suggest a way of looking at a concept or situation.  When confronted with a challenge I try to tell a story from my own experience that has the same characteristics of the problem with which the mentee is dealing. I walk through the story, explain what I thought was important, and why I think it is similar. Then I describe what I did and what the outcome was.  I think it is very important to explain that my solution was one of several possible outcomes and that doing what I did may not bring the same results.  The goal is to give the mentee a way to think through an issue or problem, and not give them the answer.

In certain circumstances, I do offer little tips and tricks that help someone be personally more effective, but these are frequently very specific and usually have to do with language choice in meetings and similar ‘tactical’ learnings.