15 Brilliant Questions to Ask Other Leaders

Have you ever met a leader you really admired at an industry conference … only to go completely blank?

Maybe you felt a little starstruck. Maybe you knew there were all sorts of good questions you could ask them … but you ended up blurting out the first one into your head.

Having been on both ends of the situation in my career, I can definitely relate to this scenario.

Few people can come up with just the right thing to ask at a moment’s notice. All you need to do to make things different next time is to have a few great questions up your sleeve.

Preparing to Ask Great Questions

If there’s a particular leader you admire, you’re probably familiar with their work. You read their blog or newsletter, listen to their podcast, and/or follow them on social media. If they’ve written a book, you’ve read that too.

Don’t waste precious moments of face-to-face, one-to-one interaction on questions that they’ve already answered a dozen times.

There’s no point, for instance, asking them how they got started in their industry if the whole story is already published on their blog or in their memoir.

Questions That Help You Learn

These questions may lead to vital insights that you’d spend months, if not years, learning on your own. You may also find that some of the answers are encouraging and affirming: while you might not yet be far along your own leadership path, the person you’re talking to has been in your position too.

1. What are you most proud of?

Be prepared for unexpected answers. It might be their kids or their spouse, or something they achieved twenty years ago, rather than their current business.

2. Which one thing do you wish you’d done differently?

This can be very revealing – and it may steer you away from dangerous mistakes that are only really obvious in hindsight.

3. What’s the best book you’ve read this year?

As a leader, you should be regularly reading great books by other leaders: these will contain the best of their wisdom in an easy-to-digest format.

4. Who are your role models or mentors?

This can also be revealing, and it may lead you to follow other great leaders in your field. It can also be an opportunity to find a good point of connection – perhaps one of those role models or mentors has also played a part in your life.

5. When you’re considering partnering with another person or business, what factors are deal-breakers for you?

A good partnership can lead to great gains on both sides … but a poor one can eat up a huge amount of time, energy and money. This question helps you learn the red flags to watch out for.

6. How do you keep your employees (or team members) keen and motivated?

Even if you don’t lead a paid team – e.g. you’re the leader of an online community or a group of volunteers – it’s crucial to know how to motivate the people you’re working with.

7. What’s the most important factor you consider when hiring someone?

You might not yet be in a position to hire a full-time employee, but even working with the wrong contractor can cause a lot of hassle.

8. What’s the biggest risk you’ve ever taken?

This could lead to a couple of potentially interesting answers: either you’ll hear about a great risk that paid off, or you’ll hear about something that doesn’t initially sound like much of a risk (e.g. working long hours) but that turns into a cautionary tale.

9. What are your current goals?

It’d be very surprising to find a leader who didn’t have specific goals. You might want to take a mental note of how many goals they have and what timeframe those goals cover, and see how their approach to goal-setting compares to your own.

10. How do you help new hires quickly “get” your businesses’ values?

Even if you hire someone who’s clearly got the skills you need, you also want them to quickly fit into the culture that you’ve deliberately fostered and developed. This won’t happen by accident. By learning how other leaders do it, you could prevent serious problems for your own company in the future.

11. When would you make the decision to let a difficult employee go?

This is about deal-breakers or lines in the sand: is there a particular offense that this leader would consider so bad that they’d fire someone? How patient would they be? This can give you some key insights into their personal values – vital if you’re hoping you might work with them or partner with them in the future.

12. How do you choose who to promote?

In some ways, this is the flip side of the previous question. It helps you establish what qualities the leader considers especially important – and it can help you come up with a good framework or guideline for using when you’re in a position to promote someone in your team.

Questions That Help You Directly

Be cautious with these types of questions – but not too cautious. The worst that someone can say is “no, sorry” – and if you don’t ever ask, you won’t ever get. With that in mind, though, always be respectful and don’t expect busy leaders to be able to give you lots of their time for free.

13. Can I write a guest post for your blog?

This is a great win-win: you’re providing a fellow leader with great content, and they’re giving you access to their audience – which is probably larger than, and at the very least different from, your own. Don’t expect them to make any promises without knowing whether you’re any good!

Most likely, they’ll invite you to submit a piece for consideration by their blog’s editor or content manager; however, having got permission, this gives you a quick “in”. “I bumped into John at XYZ conference last week, and he invited me to submit a guest post…” will clue the editor in to who you are.

14. Could you introduce me to…?

If you’re talking to a leader who knows someone else you’d like to be in touch with, ask for an introduction. This isn’t the sort of question you can normally ask right at the start of a conversation, unless the leader already knows you. They will probably need to learn a little bit about you, and trust that you’re a sane and potentially useful contact, before introducing you to someone else in their network.

15. Can I pay you for an hour of your time?

If you’d dearly love to consult with a particular leader, this is a great question to ask! Even if they don’t offer a consultation service as such, they may well be willing to give you an hourly rate and arrange something.

Sometimes, you may even get lucky: they’ll offer to talk to you for free (though perhaps for a shorter period of time) or in exchange for something of value from you. Even if you think they might be willing to, it’s better to start off by offering to pay: that way, they know you genuinely value them and their time.

When you’re at a conference, great questions aren’t going to just pop into your mind at the right moment. Think through some ahead of time, commit them to memory, and you’ll be ready to get the maximum possible value from any chance encounter.

Which leader would you love to chat to at a conference? What’s the one question you’d ask him or her? Let me know in the comments.

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