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The one question every leader should ask themselves

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Boris is the wise ol’ CEO of TNW who writes a weekly column on everything about being an entrepreneur in tech — from managing stress to embracing awkwardness. You can get his musings straight to your inbox by signing up for his newsletter!

I know a business coach who always starts his sessions by asking his clients a single question: ”Who would you be if you weren’t you?”

What he means is; if you didn’t have your current job and responsibilities, and if you wouldn’t have invested time and energy in your current career, who would you be and what would you do?

It’s an excellent question to ask yourself every now and then, but it can be extremely difficult to answer. It’s because you are the result of a very complicated puzzle, consisting of thousands and thousands of pieces, and you’re only half-assembled.

[Read: Stop listening to your #yesbut brain if you want to grow]

The same thing goes for companies and projects. There are a lot of things you do simply because you’ve been doing them for a while. You might stick with projects that you’ve started only to find yourself now stuck with them.

That’s why you should ask yourself — at least once a year — if you were starting today, would you still continue with this project? The answer could be a firm “yes,” and that’s great. But a hesitant “no” is also interesting because it will allow you to reassess your work.

It doesn’t stop there, though, because you can apply the same thinking to your partners and employees.

If the person you work with applied today, would you hire them? It can be a painful realization when your answer is less than an enthusiastic “yes,” but maybe that discomfort shouldn’t be avoided. In fact, I tell my managers to think about employees not as fixed assets but as living beings who change alongside your company and the world — because they are.

I think it’s healthy and respectful to have a conversation with someone you work with and establish how long you’re going to work together. Back in the day, people might’ve stayed at the same job for 40 years, but I expect most people to work for you for about 5 years. Some a little bit longer, some a lot shorter.

The great thing about setting these expectations from the beginning is that when they leave — instead of feeling betrayed and abandoned — you can thank them for their contribution and accept that they gave it all they had.

You can then also view the opportunities it provides clearly and ask yourself: now that I have the budget for a new employee, who can I hire that’ll be perfect for what I want to achieve now?

So when an employee decides to leave, you can both look back on a fruitful partnership, and you’ll both have something to celebrate. You can now hire the perfect person for your next goal, and the leaving employee can move on to their next challenge. Everybody wins.

Back to the original question and your homework for the week: who would you be if you weren’t you?

Can’t get enough of Boris? Check out his older stories here, and sign up for his newsletter here.

Published March 4, 2021 — 16:21 UTC

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