On Becoming A Manager

You have been putting in the hard work and shipping great products over and over again. Eventually you will be brought into a room with one or more important people who will have a small folder from HR with your name on it. You get overwhelmed with a sense of dread that the company is about to do something awful to you. You could not be more right. I am sorry to say it: You have just been promoted to management.

Wait what? How is this bad? It isn’t really. Well it might not be. It still could be. Let’s discuss.

If this has happened to you, or is about to happen to you, you should start off with being super appreciative. When someone gives you an opportunity to explore a management role, it means you have done enough work and created enough value that they want to increase the scope of your responsibilities. If you are a smart person who can solve smart individual contributor problems, the thinking goes, then you are likely a smart person who can solve smart team problems.

After you are done being appreciative, you should be utterly terrified. If you are not, then you might not be ready for what is about to happen to you. Your whole world is about to change.

The reason to be terrified is that generally the exceptional engineer promoted into management is pretty much just thrown into it. There is a high degree of trust that somehow people will figure it out. This is probably a self-justification repeated by someone over and over again while they are making the decision to promote someone. Saying it repeatedly, unfortunately, does not make it true. Generally, a promotion to a manager role happens outside of the scope of your existing career progression track. Most of the promotions I have observed are battlefield promotions that plug an organizational hole created by attrition.

We can discuss the nature of the attrition problem, especially among leaders and managers, at a later date. It is complicated. There is a lot of fear that hiring a talented manager from outside of an existing team will come across as a betrayal to existing individual contributors, especially ones who feel like they are ready to advance in their careers. Whether that has any merit, it is scary to bring someone into your organization from the outside as a manager. You do not have a lot of time to get to know them through the interview process. It is, unfortunately, far too easy to just promote someone into that role who has already earned the trust from their leadership. Everyone will sign off on that. There will be many high-fives and fist-bumps all the way around.

You might get the sense that I am not overly excited about promoting people to managers. That could not be farther from the truth. I have made a point to promote all of my best people, when they are ready for it. There is some nuance there. I am very unhappy at the average battlefield promotion that I have observed. Quite often the people are not ready for it. As a result, it can end up as a catastrophic failure.

I was asked by one of my peers at a previous job about what I do to prepare a future manager. I very quickly launched into a monologue about a series of conversations I have with a manager-to-be. We go through a litany of topics on very important things that they need to think about in their new role. We talk about hiring people. We talk about firing people. We talk about how to run a meeting, and how to write an email. From the time that I want to start grooming someone for a management role, to the time that I make it happen, is generally a six week window.

For the first time, I decided to write all of these things down. I was doing this process pretty much ad hoc over the years and it had become second nature for me. There was enough interesting stuff here that my peer started a boot camp to discuss these items, and eventually it turned into a weekly lunch meeting for future managers to help them understand the scope and depth of management.

However, since I am not presently somewhere in your org chart, the odds are you have just received a battlefield promotion and now you are trying to figure out what the hizzeck to do about it.

Do not panic. I am here to offer you some advice and assistance.

For starters, the first question to ask yourself is “what is in it for me?” If your leadership has given you this role provisionally and has hand-waved over the compensation part of it, you should be concerned. You should get something in writing about danger pay for your role, even if it is something that arrives at the next corporate pay cycle, and ideally retroactive. Before this moment is anything else, it is a negotiation. If you are given more work and more responsibility, and they are not giving you more consideration, you should make note of that. See my previous discussion about attrition. I have bumped some people up in the past on a promotion. If it had red tape issues around that, I always did my best to get it addressed eventually.

Once you have made sure you are getting the extra moneys or the extra equities, you should also make sure that you can build an escape hatch into your promotion. I generally try to give everyone an opportunity to sample the exquisite fruits of management roles with the promise of letting them return to an individual contributor role if they do not like it. After all, not everyone likes pineapple on their pizza. I defend the pay-bump for people who fail to want to stay a manager, by the way. If you get a slight bit more cheddar for having taken a shot at management I believe you are truly more valuable whether it works out or not. I also think that establishing that escape hatch makes people more comfortable in discussing their issues and concerns. And there will be issues and concerns.

How do you work through these issues and concerns? Do not do it alone. Find an ally. It is vitally important to find someone to help you work through these as fast as possible. It can be someone you work with directly, or someone who has been through this transition in the past. There is no worse manager than the person who goes dark and keeps all of their issues bottled up inside. If this is you, and you do not have someone within your leadership group with whom you can have safe discussions about what concerns you, then you are violating the trust placed in you. Please make sure to find a supportive ally with whom you can resolve your fears and concerns. If that does not exist for you, then you are going to be eating a lot of pain and suffering alone in the darkness. I have lived this before. It is not fun. I hope you can endure it and it does not break you.

Now that you have your escape hatch, ally, and maybe a little extra beer money, please explicitly ask what success in your new role looks like. You are being given this role because you were very good as a developer, or perhaps as an architect. The people who gave you this promotion trust you a great deal. What they do not realize is that they are likely trusting you too much, and might not be giving you the scaffolding and support you need to be successful. This is a scary place to be, especially if you do not have clear success criteria.

Most people promoted to a first time management role were very successful individual contributors. They were very good at getting stuff done. The problem with this is that the definition of success changes with a management role and being very good as an individual contributor can be a net negative as a manager. It is sometimes too easy to just assume when things go pear shaped that you can just jump in and individually contribute your way out of the jam you are in. This trains your teams to wait for Superman to come rescue them. Congratulations! You are now doing two (or more) jobs that are very difficult.

If you have to jump in and do things directly, you have to make it clear to everyone on the team that This Is Not Okay. This is a sign that something is not working and that there needs to be change accordingly. It is important to figure out what made the kids incapable of doing their own science fair project. Make sure that if you do this once that it is a moment of pain and regret for everyone and that there is a path forward for everyone to do their own work successfully.

You should also be aware that you are about to enter productivity freefall as a manager. It feels good to write code and build things. You must resist these urges most of the time. It is a dangerous trap because you get a false sense of accomplishment while you build something that probably would have earned you kudos in your last role. Instead it harms your team’s growth, which is what you should be measuring in your new role.

I could go on here. Some people are not clear about what their new role is and are constantly trying new things to see what fits, and what works, and what feels good. Sometimes people take on product management responsibilities, assuming that this is somehow a part of their new role. I have been guilty of this in the past. It took me a while to learn that your output as a manager should be reflected in the product through other people’s work.

The mind-blowing realization you should take away from this is:

Your team is your product. 

Quite often that is the realization that most people miss which is so important to your success.

Am I a jerk for burying the lede so deeply? Maybe. I am doing this for free, you know. If I put that up at the top I may as well have started twerking too and then put this whole thing on TikTok. Enjoy that mental picture!

Now that I have scared you a little about staring into the abyss, it is important that the abyss stares back at you. You should absolutely ask the person who promoted you for a series of check-ins on your new role. Start it weekly or biweekly, move it to monthly as you get comfortable and get enough positive feedback, and then move it to quarterly or cancel it outright if you are in your groove. Making sure you have checkpoints is important for two reasons. First of all it makes it clear to the person who promoted you that they have some work to do too. Second, it makes sure that there is a dialog about any gaps that need to be addressed for you to be successful in your new role.

So let’s recap in point form for everyone who survived my wall of text so far:

• Get paid.
• Have an escape hatch.
• Find an ally.
• Define success.
• Your team is your product.
• Set up checkpoints.
• Seems like a pretty good list for a first-time manager, I think.

Once again thank you for reading along. I enjoy the follow-up conversations that arise from these articles; I have been humbled by the messages, both private and public, from people who have put their eyeballs all over my brain-pourings.

See you next week! We are fast approaching my attempt to do a four part miniseries that I will use to bring 2020 to a close. Who knows? Maybe it will be optioned for a series on Netflix.