03/09/2026
A client spent months trying to delegate. One question fixed it.
We'd been circling the same topic since spring. He'd make a list of tasks to hand off, then quietly take them all back within two weeks.
His theory was workload. Too busy to train anyone properly.
I believed that for a while too.
Then one call I asked him: what would you delegate if you trusted the outcome would be 80% of yours?
Long pause.
Then he named four things. Fast. Like they'd been sitting there ready.
The block was never his calendar. It was that anything under 100% felt like a failure with his name on it.
The 80% version ships. The 100% version sits in his head while he does everything himself.
He handed off two of the four that week. Kept two, which honestly is fine, some things should stay yours.
But the list existed the whole time. He just needed permission to accept good instead of perfect.
03/09/2026
That "difficult" person on your team probably isn't difficult at all.
I sat in a meeting last month that should've taken 20 minutes. It took an hour.
The leader was a Red-Dominant. She wanted a decision. Fast. Move on.
Her report was a Greed-Steadfast. He kept asking who this would affect. What happens to the two people on the old process. Whether anyone had talked to them yet.
She heard stalling.
He heard recklessness.
Neither was true. Actually, that's not quite right. Both were a little true, which is what made it so annoying to watch.
Here's my system for these meetings now:
1. Name it out loud. "You want a decision, he wants to know the impact on people. Both are on the table."
2. Give the S the people question first. Five minutes, who's affected, what changes for them.
3. Then hand the D the decision. She gets her speed, he already got his answer.
That's it. The meeting shortened by half the next time they ran it. Not because anyone changed. Because nobody was fighting a personality that didn't exist.
The D still wants speed. The S still wants safety for people.
You just stop pretending one of them is the problem.
03/09/2026
I ran the same broken 1:1 for almost a year.
Same guy. ADHD, brilliant, always "on track."
I'd open with the task list. He'd give me clean answers. Everything fine.
Then a deadline would blow up and I'd find out the real blocker had been sitting there for three weeks.
The problem was my first two minutes. I asked about tasks, so I got the tidy answer. The rehearsed one. The one that ends the conversation fastest.
Now I open with one question:
"What's loudest in your head right now?"
Not what's most important. Loudest.
Sometimes it's the project. Sometimes it's a Slack message from Tuesday he's been chewing on. Sometimes it's something at home that's eating half his focus.
Whatever it is, that's the actual blocker. The task list can wait five minutes.
First time I asked it he went quiet, then talked for ten minutes straight. Stuff I'd never have gotten from a status check.
The tidy answer is a defense. Stop asking for it.
11/05/2026
🌴✈️ Do you love planning dream holidays but hate the 9-5?
I turned my travel passion into flexible income with InteleTravel. Earn commissions booking for yourself and others, no experience needed. Who’s ready to escape the desk? DM me! 🌴✈️ https://stephenkeery.inteletravel.com