Leadership self-check
Are you a good boss(to your team and to yourself)?
Free, no email, about fifteen minutes. You’ll learn something either way.

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You lead a team
Eight situations from inside a team. Pick what you would actually do, not what you would like to have done.
Someone on your team quietly fixed a problem that would have cost the company a week. Nobody outside the team noticed.
Here’s what usually happens
Usually the more human one
c. Tell the people whose week they saved what they did
Praise where it reaches the people who decide things is career currency.
Recognition that never leaves the room isn’t recognition. It’s politeness.
- a. Thank them properly in your next 1:1
- Kind, and it stops at the door of the room.
- b. Call it out in the team channel
- Better — but it still only reaches the people who already saw it happen.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
You handed someone a task. Three days in, they’re doing it in a way you wouldn’t have.
Here’s what usually happens
Usually the more human one
b. Ask what outcome they’re optimising for, then decide
The question that separates a genuinely bad approach from an unfamiliar one. Ask it before deciding it’s wrong.
Autonomy dies in the small corrections, not the big ones.
- a. Step in and correct the approach
- Most of us pick this one and call it standards.
- c. Say nothing until the deadline
- Not autonomy, just absence. You will still have the opinion on the deadline; you have only saved it up.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
It’s 21:40. You’ve just written a thoughtful message about a change happening tomorrow.
Here’s what usually happens
Usually the more human one
b. Schedule it for 09:00
Costs you one click.
What you do at 21:40 quietly sets what your team believes is expected of them.
- a. Send it
- Their evening has your thought in it now, and tomorrow’s version would have read exactly the same.
- c. Send it with “no need to reply tonight”
- Feels considerate and isn’t. You have still put a work thought into someone’s evening, now with a small helping of guilt.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
Someone new starts on Monday. Put these in the order you’d actually do them.
- Give them their first real task
- Introduce them to the people they’ll depend on
- Walk them through the tools
- Tell them what this team is actually for
Drag an item, or use the arrows. Then confirm.
Here’s what usually happens
Most onboarding starts with tools and ends with a task. People who know why the team exists and who to ask stop needing you inside a week. Tools are the easiest thing to learn and almost always the first thing we teach.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
In a planning meeting, someone asks: “Why are we doing this project?”
Here’s what usually happens
Usually the more human one
c. Say you’re not entirely sure either, and go find out
Costs you nothing and buys enormous trust. Pretending costs you both.
If you can’t answer in one sentence without opening the deck, your team can’t either.
- a. Give them the business reason
- The right answer, if it takes one sentence and no slides.
- b. Ask what’s prompting the question
- A good coaching instinct at the wrong moment: it turns their reasonable question into their problem.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
Your strongest person mentions they’re thinking about a role somewhere else.
Here’s what usually happens
Usually the more human one
b. Ask what that role offers that this one doesn’t
The only one that gets you information you can act on.
And what you learn is for them, and for the next three people who are quietly feeling the same thing.
- a. Ask what would make them stay
- Hands them the work of negotiating with you.
- c. Go get them a raise
- Assumes it’s money, and it usually isn’t.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
“My team gets feedback from me more often than once a quarter.”
Here’s what usually happens
Usually the more human one
a. True
Then the loop is short enough to be worth something.
Quarterly and annual reviews are a compliance artefact, not a feedback system. Feedback that arrives more than about two weeks after the thing it’s about has stopped being feedback and become a history lesson.
- b. Not really
- Common, and not a character flaw — it is what the review calendar trains.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
Your team has hit its targets three quarters running. Two people have quietly started taking Fridays off.
Here’s what usually happens
Usually the more human one
b. Ask the team, openly, whether this pace is actually sustainable
The only move that turns a guess into information while it is still a guess.
Sustained performance and quiet withdrawal very often arrive together. High performers rarely announce that they’re running out; they reduce their surface area first.
- a. Nothing. They’ve earned it
- Generous, and it leaves you guessing which of the two things this is.
- c. Raise the target: clearly there’s capacity
- How you find out too late.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
You lead yourself
Eight situations from a business of one. Nobody is watching, so answer honestly.
It’s Monday morning. What decides what you work on first?
Here’s what usually happens
Usually the more human one
b. The thing I decided on Friday
Made with a calm head instead of an inbox-shaped one.
Deciding on Friday what Monday is for is the cheapest productivity system there is.
- a. The most urgent message waiting for me
- Then the day belongs to whoever wrote to you last.
- c. Whatever I’ve got the energy for
- Not wrong — energy is real data. It just can’t be the only input.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
A client asks for something small. It’s Sunday afternoon.
Here’s what usually happens
Usually the more human one
b. Reply Monday morning
Nothing breaks. Monday was always when this was going to happen.
And you will not be the one who gets to close it.
- a. Do it. It’s five minutes
- The five minutes isn’t the cost. The precedent is.
- c. Reply now to say you’ll do it Monday
- Fine once. Done twice, it has taught your client that Sunday is a channel.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
A new skill would clearly help your work. Put these in the order you’d do them.
- Buy the course
- Block the time in your calendar
- Tell someone you’re doing it
- Find one real piece of work to use it on
Drag an item, or use the arrows. Then confirm.
Here’s what usually happens
Courses are the easiest thing to buy and the easiest thing to abandon. A real piece of work gives the skill somewhere to land, and one witness does more for follow-through than any curriculum.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
“I could name three things I did well in the last month.”
Here’s what usually happens
Usually the more human one
a. Yes
Then you are keeping the list. Almost nobody working alone does.
Working solo means nobody else is keeping that list. If you don’t keep it either, the only record accumulating is the one of things that went wrong, and that becomes what you think your year looked like. Keep a done-list, not just a to-do list.
- b. Not off the top of my head
- The usual answer, and the reason for the line below.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
You quoted a price. The client says it’s too high.
Here’s what usually happens
Usually the more human one
b. Come down on scope, keep the rate
Keeps your rate honest and turns a rejection into a conversation about what they actually need.
What they are testing is not the number. It is whether the number moves.
- a. Come down on price
- Teaches the client the first number was invented.
- c. Ask what budget they’re working with
- A good second move. Just not before you’ve held your ground once.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
Other than clients, who have you talked to about your actual work this month?
Here’s what usually happens
Usually the more human one
b. One person who gets it
One standing conversation with someone who understands the work. That is what the people who last longest almost all have.
Usually the more human one
c. A group I’m part of
The same thing with more people in the room. Both count.
That’s not networking. It’s maintenance.
- a. Nobody, really
- Solo isn’t the same as alone, but this is how it turns into that — slowly enough that you don’t notice.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
You’ve had a genuinely bad week. Nothing landed.
Here’s what usually happens
Usually the more human one
c. Look at what actually happened before deciding
Twenty minutes, and then (a) or (b) is a decision instead of a flinch.
One bad week is noise. Three in a row is a signal. You can’t tell which one you’re in without looking.
- a. Push harder next week
- A reflex, and sometimes the right one. You just reached for it without looking.
- b. Take a full day off
- Also a reflex, also sometimes right, same problem.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
“I’ve said yes to work I didn’t want, because the money was good.”
Here’s what usually happens
It’s whether you knew why, and whether you know how many more of these you’re willing to take before something has to change. A yes with a number attached is a decision. A yes without one is a drift.
- a. Yes
- Sometimes that’s exactly the right call. The test isn’t whether you took it.
- b. No
- Also fine — and the same question applies to the ones you turned down.
No answer here is the right one. It depends on the situation, the team and the day — some approaches just tend to cost people less.
Keys: arrows move, Enter or Space chooses, 1–3 pick an option, Escape pauses.
Your shape
| Component | Reading |
|---|---|
| Purpose | |
| Autonomy | |
| Recognition | |
| Growth | |
| Belonging | |
| Wellbeing |
Where it is thin
Strongest
Where most leaders land
What now?
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