Humpty Dumpty

I attended an OC CTO Tech Talk this week. The speaker was impressive and told an awesome story about migrating from Redshift to Databricks on AWS. There was a really well-built slide in the middle about the importance of mapping your long-term technical roadmap projects to business objectives and metrics, and this one bullet point stood out to me: “Avoid chasing shiny new tech.” I scanned the audience on this slide and witnessed an ocean of furrowed brows and puzzled expressions. At the end of the talk, there was this hilarious schizophrenic Q&A where about half of the questions came from the audience around shiny new tech and tactical questions, and I had my hand up to ask a series of related questions around soft skills, coaching, and having a mentor.

I talked with the speaker at the end of the event and thanked her for an amazing presentation. We spent a few minutes discussing the challenges of growing people professionally. In particular, we both commented on how there is a decent amount of trauma from previous bosses for most people who join your team at a startup.

Sometimes, managing people feels a little like being a professional psychologist. I first encountered this phenomenon over twenty years ago at Digital Chocolate. I was in my first director-level role and struggled a little with some of the business strategy and product direction. After some of my 1:1 meetings with company leadership, one of my peers, a producer, would ask me how the head shrinking was going. Five years later, I reflected on that comment while managing a team. We hired a new developer, and I spent considerable time unpacking that team member’s issues to help them be more successful.

Let’s fast-forward to today, after many years of high-velocity team building. I have learned that most people’s performance is heavily impacted by their previous managers—sometimes positively and sometimes negatively.

If you have an employee who has had a toxic manager or a manager with a scarce mindset, you will need to spend considerable time helping them work through that trauma to make them successful. I know that my two worst managers have shaped some of my behaviors. Now that I am in a leadership role, I find myself staring in the mirror occasionally to see if I can see them staring back at me. Whatever my faults are as a leader and a manager, there is a subset of behaviors that I self-regulate heavily to make sure that I never manifest them.

I don’t want to make light of people with startup trauma, but making them successful long-term is a lot like rebuilding Humpty Dumpty after his wall incident. It takes a lot of effort to get people into a place where they can deliver great work and feel safe to take important professional risks.

What are some things you should look out for?

The frightened messenger. If people try to hide bad news or get others to deliver it on their behalf, they fear being held accountable for it. If something breaks, it is important to confidently tell leadership there is a problem, especially if it is serious. The sooner, the better.

Swimming in denial. Have you heard someone say, “We will be late on the deliverable, and we will move the deadline by one week” three weeks in a row? Understanding how far something is behind and what needs to be done to deliver something is important. “I need more time!” is not enough. “How much time do you really need?” is needed.

Superman syndrome. Volunteering to step in and stop the bank robbers is also another problem. This is a super serious problem if you save it and still do not manage to move the needle on a struggling project. It is also a problem if you do it too many times because if you are good at doing your team’s work and you do it enough times, they will develop learned helplessness. Sometimes, this is absolutely necessary, but it is less often than most people think.

The hedge-hog. If you think about considering the possibility of contemplating a decision after consulting with stakeholders to align synergies, you might be a hedge-hog. A trivial example of this behavior is asking someone, “What is the ETA for your current task?” They reply, “I am working on it right now!” Sometimes, people do not love committing to dates because they have been punished. It is important to make decisions and commitments.

The hungry hoarder. When I took too much food at the family dinner table, my parents would look at me and ask, “Are your eyes bigger than your stomach?” Taking on too much work and not necessarily reconciling that work against your existing commitments before accepting it suggests that someone may be a people pleaser. If they over-commit and under-deliver, they may have had a toxic manager in the past who rewarded people who would work long hours and try to push through as the hero who saves the day. This is an unhealthy behavior. I recall offering some strategic tasks to a team member as an optional activity. I was interviewing three candidates and suggested they could shadow one or more candidates to see how I do my initial screens. I know they had some tasks that were due soon, and in my mind’s eye, I believed they would decline to do all three if they were worried about missing deadlines. They cheerfully accepted all three optional interview screens, and a week later, they missed delivering on their core work. It was an unfortunate situation.

When I encounter some of these behaviors in team members, I often spend time with them unpacking the source of the behavior. If we can figure out where it started, we can create a plan to fix it.

After giving someone an opportunity to stretch and grow, like the previous hungry hoarder example, you will have a pretty clear “teachable moment” to discuss with your team member what went wrong and help go through the decision-making that led to the unfortunate result.

A previous boss often constructed hard tasks for his direct reports to observe how they got stuff done. He would assign them a challenging project with insufficient information or resources to witness their “default tendencies.” He would do this under a controlled environment to be prepared for their default tendencies when there is an actual work crisis.

It is an effective way to understand what your people are capable of, although it is a bit “old skool” as a way to learn how your team operates.

You cannot learn this early on as a leader or manager. This is one of those things you develop over time through hard practice. You will also develop the skill of fixing team members through breaking deliverables, teams, or entire companies.

Situations like these are why I choose to mentor and coach people. I have had some people who have started a new role, and from the way they describe their new boss, you can tell that there are rocks in the waters ahead. I do feel a certain amount of relief when I can help someone steer through those waters clearly. I also feel empathy during the times when we are not able to clear the rocks together, and the ship gets wrecked. Talking through what went wrong and how to do better next time is a part of professional improvement and personal healing.

I suppose this is where I make the sales pitch. I like to mentor people and help them professionally. Let’s talk if you feel like you have team members in these situations or bosses who exhibit some of these traits and want a partner to give you perspective and help steer you through some of your challenges.

Have an excellent week!