Notes on enginering leadership and software development.

Pattern Recognition

As a manager, you're a part of at least two teams. You're a peer in the leadership team, and you're a leader in your team or managers or ICs. Your words and actions have weight on both of them.

The times WILL come when the teams you support will be royally puzzled by some decisions of your company leadership. Why do we RTO? Why did we fire person Jack? Anyone understands our product strategy for 6+ months into the future?

Sometimes you'll disagree and commit to a decision, and will have to get your team to work thorugh it. Sometimes, it would be really tempting to admit to your team that, frankly, this is not a decision you would make, but you commit and keep leadership accountable for the outcomes.

You might feel that you want to tell the team that this unpopular decision is not a pattern, and it won't happen again.

“Okay, we're done with this, for the next year, we'll do this and this, and we won't come back to XYZ instead.”

“No more layoffs! Sure we're not hiring outside of San Francisco but we won't RTO remote folks. Sure we RTOd junior roles, but senior folks are safe for the next year.”

But you can't say any of that. Well, the first time this happens and your leaders tell you they won't pull another layoff, you might broadcast it, but you really really can't make promises you can't guarantee. Ask me how I know.

This triggers a loyaly crisis. How can I be an extension of the leadership team if I can't trust they'll generally keep their word?

More experienced leaders understand their words have weight and try to be better at this, but there's really no guarantee anyone keeps their word. Companies change, and what was clear as day a year ago, won't hold later. As you get more experienced, you realize that it's not the leadership words that matter, it's the pattern of their actions in a given situation.

Note

Yeah. It pretty much doesn't matter what people say they will do, only what they actually do, and the impact of that on the org.

Any leader at some point has to make decisions that will be unpopular, and that don't feel reasonable with the context people in the company have. To support your teams better, your job is to have as much context on what your leaders are dealing with, and as much intuition in how they think and react as possible.

You have to get good at pattern recognition. Most of the time, the writing is on the wall. There are a few shortcuts to this:

  • Figure out the playbook. Some leaders would be open about their "heroes" in the industry. Maybe the organization values are modeled after another company, or every leader gets the same book recommendataion as they start in the company. Read that. Folks who idolize DHH would be different fron ones admiring "No Rules Rules".
  • Listen inside your organization better. Schedule regular 1:1s with other organization leadership folks: product, design, customer success, and of course your skip-level leadership. Which in startups is likely C-level already. If you report into a VP eng, 1:1s with your CEO is a good idea. If your skip-level is a VP / CTO, still asking for CEO's time is fair, just make sure to not waste it. Bring questions, poke, and listen.
  • Work with mentors. Folks who have been in the industry can help you read the room better. They've likely "seen every movie" and can help you play the situation out, and perhaps even prepare you to how you can assert more agency and affect change.

The kneejerk reaction to "my leaders don't keep their word" is quitting and finding another gig where leaders are "honest". But that's not how organization leadership works. As you grow as a leader, you too will make unpopular, puzzling decisions.

A good leaders is accountable. They show up and own their decisions. They coach a leadership team that can explain what happened to the org. They setup a leadership team support network that minimizes the surprise decisions. The more the leadership team shares the context with folks in the organization, the less leaders find themselves in surprise damage control scenarios.

You can affect change by soaking and sharing out more and more useful context with folks on your team.

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Originally published on Apr 5th 2025.