One of my wife’s many hobbies is cultivating a wide variety of plants on the windowsill in our kitchen. We’re not limited to the usual herbs either. We’ve got avocado pits that are trying to turn into trees, pineapple tops that are trying to turn into bushes, and she’s figured out how to keep a bunch of orchids alive so those are well represented too. She’s also picked up or been given plenty of succulents to round out this motley crew of plant life.
One succulent in particular is this somewhat flat cactus that could stand six inches high or taller if it so desired … but it never does. It’s always bent over, curved like it’s picking something up that just fell into the dirt at its feet. But this little cactus is never bent over in the same direction as the last time you looked at it.
She didn’t plant them expecting acrobatics, but they’ve become some of the most interesting parts of our windowsill garden. This cactus, along with a handful of others, is either moving during the day when nobody is looking, growing new shoots, or turning into something totally unexpected.
Nobody plants a garden thinking that they’ll never look at it or tend to it. You put the seeds in, you water, and then you check on it every few days to see what’s happening. Sure enough, something is wilting (like this plant in my office). Something you almost didn’t plant is taking over the fence. The one you put in the sunniest spot straight up died.
You didn’t plant it to let it die with no one to witness its passing. You also didn’t plant it so you could stand over it all day. You walk through your garden and enjoy it.
Most owners hand off the work and never walk the garden, or they sit and they watch for changes every moment of the day.
A few weeks ago we talked about what good looks like. Last week it was which work to hand off first. Those are the first half of delegating. This is the second half, and it’s the half many of us either skip or never reach.
Why do we skip it? Checking in feels like taking the work back. In our heads it’s black and white: either I own it or someone else does. There’s no in-between. The whole point of handing it off was to get the time back, and a standing meeting about the thing you handed off feels like giving the time right back. You said, “it’s yours,” and now showing up feels like you didn’t mean it.
So we say “let me know if you need anything,” and we wait. Sometimes that works out. Sometimes you find out in month three what went sideways in week two. Either way, you were relying on hope.
Instead, put the first check-in on the calendar the moment you hand it off, before you leave the conversation. When the cadence is part of the plan from day one, nobody reads it as doubt. It becomes how work gets done.
I won’t pretend there’s one right interval. Weekly for something new, every other week or monthly once it settles. I will say that “whenever it comes up” is not an interval.
The check-in has three jobs.
The first is catching drift. A small miss in week two is a thirty-second conversation. The same miss in month three is a client call or worse.
The second is offering help. This is where you find out what they needed and didn’t ask for. People rarely volunteer “I’m stuck” to the person who just told them the work was theirs. So ask. What’s slowing you down? What would you want from me that you haven’t asked for?
The third is the one I think gets missed: learning and/or observing the unexpected. You handed off something you’ve done a hundred times, and the person you gave it to has, over time, done it their way. What did they change? Did it work? Sometimes their way is worse, and you’ve caught it early (this is the result most of us expect and go looking for). Sometimes, though, it’s better, and you never would have known if you hadn’t asked. Sometimes the cactus is bent over in a new direction and you have no idea how or when that happened.
One rule for when you do find a difference: ask before you correct. “Walk me through why you did it this way.” Either you learn something, or they hear their own reasoning out loud and fix it themselves. If you correct first, they learn to run things by you before acting, which is the exact habit you were trying to hand away.
This week, pick one thing you’ve handed off. Put a check-in on the calendar, tell the person it’s coming and why, and write down one question to ask: What did you do differently than I would have, and how did it turn out?
Then listen to the answer before you say anything. Email me what you hear, or poke me the next time you see me.