I became a manager in 1981. The biggest challenge, at the time, was delegating work to people who sat ten feet away.
That sounds trivial now. It wasn’t. Handing something to a person you can see, then watching them do it slower and differently than you would have, is the hardest thing a new manager has to learn, and proximity makes it worse instead of better. You can see every choice they make. The temptation to lean over and take it back is constant.
Nearly two decades later I was running technical operations at Trader Joe’s, in a company that prided itself on moving fast. The mechanics of the job by then were unrecognizable. The thing underneath hadn’t moved at all.
What has changed about management?
Nearly all of the practical apparatus.
Your best developer is in another country. Your newest hire expects a say in significant decisions inside their first month. Two people who have never met in person, who communicate through a chat channel, can develop the kind of mutual resentment that needs a mediator and a conversation most managers have no idea how to have.
None of those situations existed in 1981 and nothing I learned covers any of them. The org chart, the weekly meeting, the walk through the department that told you what kind of week everybody was having: all of it assumed you could see people.
None of those situations existed in 1981 and nothing I learned covers any of them.Share on X
What I learned the hard way at Trader Joe’s is that the managers who succeeded were the ones who could make good decisions with incomplete information and build trust with people they didn’t see every day.
What has not changed?
The core failure, the one I made first and watched almost everybody else make since.
I made it first because nobody taught me anything else. I was promoted from programmer to supervisor of eight people, because management was the only way to make money on a raise. I had no management experience, no classes, no nothing. Later I went on to VP. Did I know what I was doing back then? Not a prayer.
A manager takes on the difficult piece themselves because they can do it faster and the deadline is real. It works. The thing ships. And the team has learned nothing, and is exactly as dependent on that manager as it was before. That’s the job being done backwards, and it feels like leadership the entire time it’s happening because the output is good.
What is the difference between output and capacity?
Output is what got delivered this quarter. Capacity is what the team could deliver next quarter without you in the room.
These get confused constantly, because output is visible and capacity isn’t. You can run a team at high output for a year while building no capacity whatsoever, and every review will be excellent, and the team will fall over the first time you’re unavailable.
The test is simple and uncomfortable. Take a week off and see what happens. If everything waits for you, you’ve been producing output. If it moves without you, you’ve built something. I’ve been on the wrong side of that test. It’s not a pleasant discovery and it’s considerably better to have it while you’re still there to fix it.
Why does a book of principles not help?
Because nobody has a management problem in the abstract.
You have a specific person, on a specific Tuesday, who has done something you didn’t expect, and you have about four minutes to decide what to do. Principles are easy to agree with in an armchair and useless at that moment, because the difficulty was always recognizing which one applies while somebody is waiting for you to speak.
That’s why I wrote the book as three managers going through the situations instead of as a list of lessons. You watch somebody make the decision, badly, and see what it cost. That sticks in a way a principle doesn’t, and it means the next time the situation arrives you’ve seen it before.
The book on this: Street-Smart Management Wisdom follows three managers through the situations you’re living, in 14 chapters, so you can watch somebody else make the mistake first.
What is the hardest part of becoming a manager?
Let them do it worse than you would. That’s the job. The alternative is a team that never improves and a manager who never gets a holiday.
Test for capacity. Take a week off and watch what happens.
Build trust deliberately, because it no longer accumulates on its own. Proximity used to do this for free. It doesn’t any more.
Decide with incomplete information. You’ll never have the full picture, and waiting for it is itself a decision, usually a worse one.
Handle the small resentments early. Two people who can’t see each other’s faces will assume the worst about tone, and it builds until it needs a mediator.
Forty-five years since I first had to hand work to somebody ten feet away, and I still think that was the correct thing to find difficult. Everything else in management is a variation on it.
