Leadership in Tech
Leadership in Tech
#340 – August 23, 2026
tech loves chasing trends often copying them without asking if they fit
You don’t have to be at the edge
5 minutes by Francisco Trindade
Tech loves chasing trends like Agile, the Spotify model, or heavy AI quotas, often copying them without asking if they fit. Being reasonable and understanding your own context matters more than following the latest meme. Strong experimentation and solid execution let you catch up later, so you don't need to be first to succeed.
[Webinar] How to stop babysitting your agents
sponsored by Unblocked
Agents can generate code. Getting it right for your system is the hard part – you end up wasting time and tokens in the back and forth. More MCPs solve access but not understanding. Join us for a FREE webinar on Sep 2 to see how to give agents exactly what they need the first time (includes a live demo).
Coach and judge
5 minutes by Jim Grey
Coaching an underperformer too long hurts both the team and the person. Five signals suggest it's time to stop coaching and start giving direct feedback: the same excuse keeps repeating, you've named the same gap more than once, support was given but nothing changed, the team is covering for them, and your own language has turned defensive. Being direct is the kinder path.
Incubate, compound, refinance, liquidate
6 minutes by John Cutler
Software portfolios have assets that create value, assets that cost too much to maintain, active bets, and dead weight. Where each asset sits, and which direction it's moving, shapes what AI can actually do for you. AI can speed up prototyping, refactoring, or exploration, but it can also accelerate the wrong motion. The real question isn't whether AI makes you faster, but faster toward what.
Roadmap decisions rather than dates
11 minutes by Will Larson
Modern software teams are rarely blocked by time or bandwidth. The real bottleneck is making good decisions fast enough. Prototyping cuts through ambiguity by eliminating bad options quickly, turning complex problems into simple ones. AI tools now make this approach cheap enough that any team can use it, and organizations that focus on accelerating decisions rather than scheduling work will consistently ship faster.
Abductive reasoning
8 minutes by Phil McKinney
Sherlock Holmes wasn't deducing. He was guessing well. That skill has a name: abductive reasoning. It means working backward from a surprising fact to the best explanation that fits it. Unlike finding patterns or following logical rules, abduction creates new ideas, which is why it remains something humans do better than AI. You can sharpen it by noticing surprises, forcing multiple explanations, and testing your best guess cheaply before committing to it.
How do you evaluate a senior engineer in the age of AI?
sponsored by AssureSoft
When AI can accelerate execution, traditional signals of seniority don’t tell the whole story. This 30-point checklist gives engineering leaders a practical framework to score senior-level readiness. It includes a ready-to-use interview questionnaire, so you can see if your hiring criteria have kept up.
And the most popular article from the last issue was: