“Does this ever get easier?”
It’s a question I’ve been asked probably a dozen times by first-time managers, directors, and even VPs.
I’ve watched exceptionally experienced leaders mishandle situations they’ve mastered before. Even run-of-the-mill things like writing OKRs, executive status updates, bootstrapping new projects, and delivering negative feedback. No matter how much experience you collect, you can’t just run on instinct—it will never feel truly “easy” the way riding a bike, touch typing, or other sorts of muscle memory do.
The root cause isn’t that “people are hard,” or even that each level you ascend exposes new challenges. Both are true, but the deeper problem is the sheer breadth of any management1 job.
Most of what you know is cold
Leaders must deal with nigh on thousands of insane situations; I trauma-dumped an entire listicle with 142 of them. Each problem individually isn’t even that complicated, but there’s just so. damn. many. of them! Most leaders already carry the right mental models somewhere, but any given one may go untouched for 6+ months.
Worse, small permutations can completely change the ideal approach. Consider an example: at some point you’ve probably had to alter a peer’s priorities or stop a nearby project that is interfering with one of your own. No big deal—a productive escalation to resolve conflicting priorities is literally the ABCs of management—except you might also be dealing with one of a zillion different complications, including…
The project in question is someone’s “promo project” so the other manager will defend it with their life to avoid attrition.
Your boss and their boss are actively feuding over something else entirely, and this escalation will give your enemy ammunition.
The other project is halfway done, and sunk-cost fallacy is clouding everyone’s judgment.
Your engineers were wrong about the technical needs here and got you all gassed up about nothing.
…on and on the list goes.
There are some really dark corners—when did you last deal with an export control audit or a coordinated disclosure of a zero-day in your product? As a result, at any given time, probably 70% of the leadership skills you’ve previously mastered have gone stale from disuse.
No matter how experienced and well-read you are, it will feel like flying by the seat of your pants. You’ll be in a meeting with 15 people, the discussion will take a surprise turn, and there won’t be time for a study break—you’ll have 500ms to intercede and say something intelligent. There will always be this vague feeling of “I know I could do this better…”
Mastery requires maintenance
You need to keep renewing and applying key concepts to stay at the top of your game. That’s why I think of leadership skills like soil: it compacts and hardens unless you work it. You can’t endlessly plant new ideas; you need to till the soil to keep the ground workable.
I’m sitting here in the airport reading Alex M. H. Smith’s No Bullsh*t Strategy—this is probably the 18th “strategy” book I’ve read in my career. You would think we’d run out of interesting and novel things to say on the subject by now…and you would be right. It’s a lovely book and earns my recommendation—it just doesn’t say anything I haven’t heard before, and that’s fine. The point of continually re-reading and reflecting on these business books is not to receive novel insight; it’s really about keeping the core patterns alive so they are readily available when you need them.
Then, when a situation pops up at work, the effort to recall what you read and apply it cements the concept permanently: consolidating memory traces and improving recall.
Teaching is even better. When I mentor another leader, I can’t merely recognize the right answer when I see it. I have to reconstruct the model, explain why it works, turn it into steps, answer objections, and watch whether the other person can actually use it. If they never mention the framework again, that’s useful feedback too: perhaps I didn’t understand it as well as I thought, or perhaps I packaged it badly.
Writing this blog is, in part, the same exercise.
This works so well because of the Retrieval Effort Hypothesis, which posits that greater mental effort exerted during retrieval yields stronger, more durable memory retention. The exertion of continuously reading, reflecting, applying, and teaching keeps the framework available the next time you need it.
Early on, you’ll spend a lot of energy trying to climb the skill curve and patch over missing experience rapidly…but at this late stage in my career, I’ve changed my intellectual habits. I’m less concerned with constantly searching for novel ideas because there is plenty of value in encountering an old idea at the right time, thinking about it again, and putting it back into circulation.
Really, it’s any leadership job, IC or manager. Taking accountability for a larger and larger piece of the pie looks mostly the same no matter what title is on the door 🤷♂️