Tech Leadership Maxims

My website recently crossed the 300 articles mark. Those, along with two books and hundreds of podcasts and videos made me want to write down a few basic maxims and concepts for tech executives. It’s a fun exercise for me, and definitely enjoyable for you. I’m sure you’ll hate at least one!

  1. You don’t need a tech/engineering strategy, you need to incorporate tech into forming the company’s strategy.
  2. Obsess over creating more tech capital as opposed to fighting infinitesimal tech debt.
  3. Management is a profession and requires intentional effort. A post on LinkedIn with your new title doesn’t magically provide you with the skills needed.
  4. Geeks belong in the boardroom, and if you shy away from speaking business you’ll ensure your organization will be a cost center.
  5. Cost centers tend to get resources and attention only when things are painful. Create an innovation center that’s always growing more valuable.
  6. Innovation should be habitual and take place regularly. Yearly hackathons are creativity cages.
  7. Peter Pan employees remain juniors forever. You’re supposed to help your people grow regularly.
  8. Tech executives who are not in charge of their time end up serving their calendar and make little progress in anything strategic. Design your ideal week.
  9. Putting a manager over a two-person team usually introduces more overhead than it is worth.
  10. Introducing a new level in the hierarchy to leave you with 1-2 direct reports often means you’re prematurely optimizing and disconnecting yourself from the work.
  11. An engineering team that’s consistently delivering 100% of what it committed to is underperforming.
  12. If you cannot take two weeks off without worrying about being constantly contacted, you’re failing as a manager.
  13. A leader should always have initiatives ongoing and personal goals. Don’t merely aim to deliver the roadmap.
  14. Never automatically fill a position when someone leaves.
  15. Startups that boast no one ever quit or was fired are retaining too many people who are not a good fit.
  16. Tech executives should never work with a fixed ‘engineering tasks’ budget (e.g., 15% of your time). It always gets filled even with things that are unimportant and works against you when you actually need to perform something bigger.
  17. You can teach tech mastery, but you cannot easily create growth mindsets. Look for it in interviews.
  18. Engineering teams that eagerly execute all requests from Product should introduce healthy friction.
  19. Engineers can and should understand the product and business well enough to question decisions and introduce new ideas.
  20. You’re not ‘protecting someone from getting dispirited,’ you’re withholding critical feedback.
  21. When asked to imagine having to cut 10% of projects/people, most executives immediately have names come to mind. Don’t wait until it becomes an issue and proactively move things ahead of time.
  22. Every month ask yourself if—given a magic wand that would make it so no one was upset or hurt—you’d choose to leave your role. If so, take some action now.
  23. Defrag/reset your calendar quarterly. Most of those recurring meetings can be shortened/made less frequent/deleted.
  24. Product specs shouldn’t be perfect and entail everything an engineer needs to implement the feature without talking to anyone.
  25. Arbitrary deadlines aren’t all bad. Nothing happens with a deadline.
  26. Every company gathers organizational debt from time to time. Unaligned teams and weak leaders harm companies more than bugs.
  27. Leaders should regularly wonder why no one spoke up when discovering issues.
  28. Constraints are incredibly effective in fostering creativity. Stop creating too much freedom.
  29. Leadership is not about “getting out of people’s way.” That’s abdication.
  30. Life is too short for average. Don’t lead an average team. Don’t get used to ‘meh’ months.
  31. Experience can be greatly accelerated. People can grow in a year more than many do in five.
  32. Avoid tech for tech’s sake. Your users don’t care how bleeding edge your stack is.
  33. You should be innovative in your product, that’s it. Let’s be less creative in management practices, organizational structures, methodologies, etc.
  34. Take regular time for yourself to learn, research things, tinker with your product, and think. Leadership cannot take place when you’re rushing from one meeting to the next.
  35. Stop feeding the beast: Your product backlog should never be decided months in advance.
  36. Similarly, tech teams boasting of being ‘ahead of the business’ are either too big or not focusing on the company’s bottlenecks.