Do I really wanto to run a business?

Self-Leadership Check-In: 30 Questions to See If You're Ready to Lead a Company

Running a business requires more than skills and knowledge.It also demands a mindset, a drive — and I’d even say, a way of living. After years of working with CEOs, I’ve discovered a handful of questions that, when I ask them, trigger hesitation, doubt, or even resignation.

So here they are: 30 questions. Each one is designed to make you stop and think.

You can take this as a challenge: answer one question per month (ideally), and give yourself the time to reflect.

Are you up for it?

Questions about self-awareness and purpose

Because the person who gets up every morning to lead your company... is you.

• Why do you want to lead a company?

• Are you doing this out of passion, ego, or fear of not doing it?

• What does success mean to you? Can you define it in one sentence?

• Are you willing to make deep personal changes if your business requires it?

• If you didn’t have this company (or business idea) today, what would you be doing instead

  
  

Questions about energy and self-care

Because if you’re not well, no one will be well for you.

• Do you get enough sleep to think clearly and make sound decisions?

• Do you take care of your nutrition, exercise regularly, and allow yourself to rest without guilt?

• Do you know when in the day you’re at your best, and do you organise your schedule around that?

• Do you have time for yourself outside of work? And do you enjoy it, or do you just half-disconnect?

• Do you have habits that recharge you... or just ways to numb yourself?

Questions about personal management and decision-making

Because good organisation is the foundation of any organisation.

• Do you have clear priorities every week, or do you improvise as you go?

• Do you postpone important decisions out of fear of getting it wrong?

• Are you really in control of your company, or just putting out fires?

• Can you stop in time when you're physically or emotionally at your limit?

• Do you have actual time in your schedule to think — or only to react?

Questions about coherence and leadership

Do you say, think and do the same?

• Are the values you talk about really the ones you live by? Can others see them in the way you work?

• Do you delegate clearly and follow up — or just hand things off to get rid of them?

• Do you avoid hard conversations, or face them when needed?

• Does your team know what you expect of them, or are they guessing?

• Are you the first to model the behaviour you ask of others?

Questions about culture and relationships

Because people are at the centre of everything.

• Can your team speak the truth to you without fear?

• Do you share the bad news too, or only the good?

• Are you approachable — without being invasive?

• Do you care about the actual wellbeing of the people you work with?

• Do you feel connected to the people you lead — or do you struggle to empathise?

Questions of uncomfortable truth

The ones you don’t really want to ask yourself.

• Do you genuinely like leading people — or would you rather just be left to work in peace?

• Can you see yourself still being CEO five years from now?

• What is this costing you more than you’re willing to pay?

• Do you feel you’re where you’re meant to be — or are you forcing yourself to fit?

• If you could start from scratch… would you choose to lead this company again?

Now that you've asked yourself these questions…Have you reached any conclusions?

Do you really want to lead your company? Is there something you're missing — or something you’ve got too much of?

Maybe this is just the beginning of a bigger change.

See you soon

Natalia