The Three Leadership Questions I Always Ask

Excerpted with permission from Chapter 2 of Ignite Your Leadership Expertise by Nathan Magnuson

How do you talk with other people about leadership?

Unless I’m already a trusted leadership advisor, most people don’t just come up and ask me to help them evaluate their personal and organizational leadership effectiveness. (And when they do, it’s a little more organic than that!)  It’s true the more responsibilities people acquire, the more complicated their leadership situation gets. Executive leaders usually have access to budget, resources and personnel to address the leadership challenges they face. Everyday leaders often have to figure things out on their own. You may be able to help, but how do you get the conversation started?

One of the things I’ve come to learn over the years (sometimes the hard way) is that people are often sensitive about their leadership challenges. They won’t want to talk about it if they sense you have an agenda (even if the agenda is just to be helpful). And most of the time, it doesn’t matter how much or little you know. You have to be invited. Another thing I’ve learned is that, among other things, leadership is a conversation.

So instead of trying to solve folks’ leadership challenges for them, start with taking an interest in them as a person and inviting them into a natural conversation without an agenda. Don’t start with what you know, but with the other person’s situation. Follow Stephen Covey‘s fifth habit advice, “seek first to understand, then to be understood.” This way, whether or not you’re asked for your input, the other leader knows that you care.

To help with these conversations, I’ve included my three favorite leadership questions to ask, whether I’m speaking with a new client for the first time, a friend or a new acquaintance. Instead of inviting myself to solve their problems, these questions help me invite others to talk about themselves. Here they are.

What are you working on that you’re really excited about?

This is a great opening question because it engages the other person’s positive emotions. People like talking about the things that get them excited. It highlights what is really working for them. No matter how challenging things may be, if there is something to get excited about, then hope is alive and well.

What would you like to get to next when you’re able?

This is a great follow-up question because it speaks to the other person’s goals or foresight. Do they possess a clear path forward or are they struggling to fight fires? Is the future likely to be more exciting down the road or bring more complications?

What concerns are you experiencing right now?

This is a very mild and non-intrusive way to inquire about problems the other leader is facing. Perhaps a more direct version is to ask, “What is keeping you up at night?” Instead of putting the other person on the defensive by insinuating they may by the cause, this question simply inquires about a feeling they possess. Everyone has concerns. Once you’ve engaged positive emotions, it’s much easier to inquire about any negative ones.

By the way, you may not even have to ask this question. If the future looks complicated, the other leader may volunteer as much and tell you why.

At the end of a short conversation based on these three questions, you’ll have a good grasp on what’s working, what the plan is and what the challenges are. This puts you in a great position to provide input, offer a possible solution or to simply ask how you can provide support.

Theodore Roosevelt is credited with observing that, “People don’t care how much you know until they know how much you care.”  Will you join me in leadership conversations that are unmistakably others-centered?

Nathan Magnuson


Nathan Magnuson is a corporate leadership development consultant, author and communicator. He’s worked in a staff or consulting role with several Fortune 500 companies and large public service organizations, including Accenture, MASCO, FBI and Defense Intelligence Agency. Nathan is also a military veteran, having served a tour with the Army Special Operations in Operation Iraqi Freedom. You can visit him at or on Facebook, or purchase his book Ignite Your Leadership Expertise.


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