Cars get an annual inspection because things wear out slowly and, to the naked eye, invisibly. Also, because nobody enjoys discovering a problem whilst they’re driving at seventy miles an hour. Leadership works in much the same way, believe it or not, except almost nobody books the annual appointment.

So, this article will give you a leadership check-in. Specifically, it’ll give you ten questions about yourself, your people, and your business. Now, let’s stop talking about it and let’s dive in, shall we?

Part One: Yourself

1. What am I tolerating that I shouldn't be?

We encourage what we tolerate, both in others and in ourselves. Be it the meeting that always overruns, the colleague who is always late with their numbers, or the silently slipped standard.

If you let them, every one of these things teaches your people what’s acceptable in your organization. Whether you explicitly say so or not.

2. If someone shadowed me for a week, what would they think I value?

What would an observer conclude from your calendar, your reactions, the things you chase, and the things you let slide? Your behavior is the only version of your values that other people can actually see. So, that’s your answer, rather than good intentions alone.

3. When did living my stated values last cost me something?

If you can't think of an example, either your values have never been tested, or they’ve fallen apart when they were. It's remarkable how quickly our deeply held principles can become flexible guidelines when the quarterly numbers look a bit wobbly, which is precisely when they matter most.

So, look back and truly reflect honestly about the last time this kind of thing happened.

4. Who holds me accountable for my own development?

Nobody will hold you accountable for your growth if you don't hold yourself accountable first, and if the honest answer to this question is "nobody," then that's your next move.

Find someone who tells you the truth, asks uncomfortable questions, and reminds you what you said you'd do.

Part Two: Your People

5. Where am I too involved?

Think about how things run when you're away for a few weeks. If you're on vacation and it feels important to check in every day or so, then you have your answer and a warning sign rolled into one.

Because the best leaders work to make themselves redundant, which lots of leaders miss.

6. Who am I not developing enough?

Most leaders invest disproportionately in their A-players, because it's enjoyable and the returns are quick. So, ask yourself when you last coached a B-player, or had a genuine development conversation with someone in the C category rather than a performance one.

Your A-players would likely thrive with or without you, which makes the others the more interesting option.

7. Do I default to "here's what to do" when the moment calls for "here's how I'm thinking about it"?

Most leaders communicate what needs doing, by when, and to what standard. Now, this is useful, but if your team only ever knows what to do, they'll always need you around to tell them.

Sharing your reasoning and your trade-offs is how people learn to think like you instead of simply executing your instructions. So, do that!

Part Three: Your Business

8. What are we doing that no longer serves our strategy?

Every organization accumulates activity the way a garage accumulates paint tins. The client relationship you've outgrown, the reporting nobody reads, the product line that made sense in 2019. Pick the biggest one and ask what would break if it stopped.

9. What are we great at that the market values?

If you're great at something the market doesn't value, that's a hobby. If the market loves it but anyone can do it, that's a commodity. If it's unique but you're not excellent at it, that's a gamble.

Your strategic edge is where all three overlap, and if you can't name yours in a sentence, that's a useful discovery to build on.

10. If I disappeared tomorrow, would this business be stronger or weaker?

We’ve left the hardest one for last, and the one most worth sitting with. Would the leaders you've developed know exactly what to do, or would things grind to a halt while everyone waits to be rescued?

Every day you're building one of two legacies, and this question tells you which.

Final Thoughts

A leadership review only works if you write the answers down and then do something with them, which is admittedly the tricky bit. But it’s important because leadership reflection has a habit of helping you produce very wise observations that then go absolutely nowhere.

So, choose the two answers that made you wince most from the above, decide on one concrete action for each, and put those actions in your calendar before you close the notepad.

Find Out More

These leadership questions to ask yourself are a solid start, though self-assessment has an obvious limitation in that you're marking your own homework.

The My Daily Leadership Leadership Insights Scorecard gives you a clearer picture of where you're strong, where you're not, and which of the Five Levers of Leadership needs your attention most. It takes a few minutes, and it's considerably more honest than your own handwriting.