Hey all! I am sending this a bit later than usual as we spent the day yesterday doing a trail run on the Rattlesnake Mountain Traverse. I remember asking my wife, "hey, should I bring my crampons?" and her reply was, "It's possible there's a little snow, so you probably should bring them, just in case."

This answer turned out to be hilarious because we spent hours forging a new trail through multi-foot deep snow. And yet, we succeeded, only a bit colder and wetter than expected.

Careers (as they grow) can feel like waves.

  • You are asked to accomplish tasks. Those tasks are challenging.
  • You learn new skills to accomplish those tasks. You're able to accomplish those tasks.
  • They become easier, so you're promoted, get bigger assignments, are assigned into leadership positions.
  • You attempt to apply your old skills to those harder tasks. You're not as successful.
  • You unlearn some skills and learn new ones.
  • You're able to accomplish those tasks.

That bold line is what I'm talking about today.

If your career is growing, you've had success along the way. You learned how to do certain things well, and have been rewarded for those behaviors.

Some of those behaviors will be rewarded forever. If you code well, that will never hurt you. If you write well, it's good forever. If you have an eye for design, that's useful anywhere.

However, other behaviors or skills work, until they don't. And it can be hard to recognize those moments. You've recently built a successful career using a specific way of working, and changing how you work can be difficult.

I'll walk through three types of behaviors / skills which helped move me from a junior manager to a senior manager, and then review the changes needed to get me to a Director / Executive position.

Quick independent decisions worked well ...

As an IC, I relied on my manager to help make strategic decisions. Is X feature more important, or Y? Should we deploy now, or Friday? Who should I notify about X feature launch? Sometimes my manager would make decisions slowly, and our team would grind to a halt.

As a manager, I realized that unblocking my team quickly was a great skill to have. I took the available information, and learned to make decisions in ambiguous situations quickly. Being decisive became an advantage as a manager.

As a leader of primarily ICs and more junior managers, taking away ambiguous / complex decisions frees them up to accomplish their daily tasks.

I remember a situation as a manager, where I was speaking with an engineer on my team. They explained that they had spent the entire two previous days with our legal partner. The lawyer was working with the engineer to determine some data retention policies. The problem and potential issues were unclear (and had large impact), and the engineer spent a significant amount of time researching and collecting data. This means we'd spent approximately 1% of that engineer's yearly output on an ambiguous legal investigation.

I took over the issue, and quickly realized that none of the data we had needed to be stored long term. I was able to get the engineer back to working on tasks, and the lawyer was relieved to have an answer.

Being decisive and moving quickly became an advantage against other managers. Not like it's a competition, but it somewhat is. Particularly as you get more senior, you need to stand out from the crowd. Moving quickly can make you stand out from the crowd.

While another manager waffled on an important project which required re-prioritizing their roadmap, my team was already done with the important work. In cases where other teams were spinning their wheels with unclear requirements, my team was plowing ahead full speed with Dave's decisions.

Essentially, one of the reasons I reached senior management was because I heard of a decision for my team, I listened to the available data, and personally made the decision quickly. It ensured that my team could execute, and I could lead.

... until my team members became more senior

Everyone wants to have autonomy in their work. Demonstrating leadership and ownership over your tasks feels great. At least when the scope and impact and type of problem is appropriate for your skills and interests.

As a software engineer with a few years of experience, creating a data retention policy for a large application may be uncomfortable. It's not the type of autonomy and leadership many engineers are excited about. Therefore, it wouldn't have been right for me to leave that engineer chugging away with the lawyer. It really wasn't a good fit for their skills, interests, or experience.

As I became an executive, the employees reporting to me changed. They were senior managers, with organizations of their own. They had many more years of experience than my previous team members, and they had an interest (and skill) in making larger, impactful, ambiguous decisions.

As I attempted to continue to make quick decisions, it began backfiring. What were the issues?

  • My senior leaders lost their expected autonomy if I attempted to decide in their space.
  • I didn't have enough context to make quality decisions.

As my team grew more senior, I realized that I needed to react differently to complex and ambiguous problems in my space.

Rather than solving issues, I needed to ensure that my team had the relevant information and guidance necessary to make their own decisions.

Several years later, I had another ambiguous legal issue come up in my organization. As a side note, ambiguous legal issues are frequent in large companies. Unfortunately.

Rather than helping to solve the problem personally, I ensured that the team involved recognized the stakes of their decisions. I asked about the potential ramifications for our peer teams, and our PR teams. I was able to escalate for them to obtain some time from a peer team to do an investigation they needed.

And then I stepped back. I let them have their meetings, do their investigations, and decide.

Their decision may not have been what I would have chosen, but it was an acceptable decision. The important thing is that it was their decision. They were able to have the autonomy necessary to feel like owners in their space.

Being a decisive person with a strong opinion can lead to career growth – for a time. Then it begins to be a career limitation unless you can recognize when it's time to take a step back and let your team take the lead.

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