Most leaders I meet are shallow. Not because they lack care. They’re shallow because they’ve stopped treating their role with the same urgency, curiosity, and responsibility they had as engineers. As ICs, they were obsessed with mastering their craft: learning, experimenting, improving. As leaders, far too many settle for “keeping things afloat.” A new year is coming. Time to get out of the shallows.
The Shallows Are Comfortable—And That’s the Trap
Your phone is slowly dissolving your ability to think. Add the convenience of AI to “polish” half-baked ideas, and leadership becomes the intellectual equivalent of fast food. Leadership is also amorphous. As engineers, “moving forward” has clearer signals. As managers, there are obvious developmental ladders. But senior leaders? Many feel stuck measuring progress with useless metrics like headcount.
Depth in leadership requires intention. It means you choose to think, shape, evaluate, and act with purpose. It means your impact becomes profound, not just present. Here are the tactics I routinely suggest to clients to get out of the kiddie pool.
Commit to Real Reviews
If even 5% of tech leaders conduct personal weekly reviews, I’d be impressed. Most teams don’t run retros consistently anymore—so imagine the odds their leaders do it for themselves. Start now: every week, 20 minutes. No multitasking. Sit and think.
What actually made a difference? What did you learn? What would you do differently?
Use whatever medium helps you stick to it—writing, sketching, dictating to AI—but the act of sitting down and thinking on purpose already puts you on a different playing field.
Call Your Shots
If you never state your predictions aloud, your mind will quietly rewrite history to protect your ego. You’ll “remember” having expected the thing that happened. You’ll overlook the bet that failed. Improvement becomes impossible when performance is blurry.
Call it. Name what you expect to happen. Put a reminder in your calendar. Track the things you claim to believe in.
During your weekly reviews, revisit key areas: is the team stronger than last quarter? Are your hires proving valuable in hindsight? Are the initiatives you pushed actually delivering?
Contrast your beliefs with reality.
Consume Better Inputs
If your intellectual diet is built from social feeds, memes, and algorithmically-tuned outrage bait, you’ll think like someone who eats junk food all day.
Pick books. Long-form articles. Read publications that require thought to digest (e.g., Refactoring and Stratechery). Replace the intellectual fast food with proper slow food. You cannot produce meaningful leadership from shallow input.
Experiment Like a Scientist
“Move fast and break things” is still popular. What’s less popular is checking whether anything actually improved. Before starting an initiative, state your hypothesis: What do you expect to happen? Why? By when?
This aligns the team on actual outcomes, not vibes. It also creates clear criteria for evaluating the work. Depth comes from intentional experimentation, not flailing your arms around.
Deliberate Exposure
No one becomes profound staring at their own Slack channels all day. LinkedIn doesn’t count. Join a community. Attend conferences. Meet peers. Build a mastermind. Talk to leaders who aren’t inside your building.
Perspective is impossible when your entire universe is your own company’s hallway chatter.
Schedule Deep Work for Yourself
Senior leaders often guard their team’s time better than their own. Your engineers have maker schedules. You have chaos. If you want deeper thinking, you must protect the time where deeper thinking happens. Block it and put it to use.
If you need help understanding how to construct true leadership blocks, I recorded a video about it, but the core idea is simple: you deserve to get time to think and work as well.
Take Actual Offsites, Not Vacations With Laptops
If you’re going to take your staff away for two days, make it count. Define the desired outcome. Assign prep work. Run it like a short iteration. Produce deliverables that move the organization forward.
Depth thrives when you step back from the frantic loops of daily execution. Real offsites create space for strategic clarity.
The Move From Shallow to Deep
I cannot tell you what to do—that’s the point. Depth isn’t a list of tactics; it’s a posture. I can help you find your path and make time to get there (and if you need tailored help, you know where to find me). But the actual shift? That’s yours.
Start with space. Then intention. Then deliberate practice. Everything else follows.