The Three Leadership Questions I Always Ask

QuestionsHow 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 is a leadership consultant, coach, trainer and thought leader.  Receive his ebook Trusted Leadership Advisor by subscribing to his website or   follow him on Twitter.

Nathan Magnuson is an executive leadership consultant, speaker and author of the books Stand Out! and Ignite Your Leadership Expertise. Click to see the exciting ways Nathan is helping organizations and teams become more effective with Leadership-in-a-Box.

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7 thoughts on “The Three Leadership Questions I Always Ask

  1. This also works for leaders to ask their employees. It’s amazing how much is gained when a person senses that you care about them, not just what they can do for you.

  2. I am working on a great Strategic Planning project for my Church. What concerns me the most is my preconceived ideas about the way things should be, instead of allowing the staff to formulate their own ideas and strategies.

    As the facilitator, I fear steering the strategic meetings we are about to have in my direction. Any ideas for a bias facilitator?

    Also, the Pastor wants to approach the strategy from a systems point of view. Three key systems we will explore include: 1) Exceptional Sunday Morning experience (all of it worship, children’s and student ministries, welcome formats, refreshments and use of technology), 2) improve use of technology (in all areas worship, connecting with others, spiritual growth etc.) and 3) Volunteers (recruiting, training organizaing, and building enthusiasm for ministry and service.)

    Thoughts are welcome.


    • Wow, John, big question! I haven’t gotten to do a post on strategic planning yet, but I do know that it’s hard to “steer” this kind of facilitated conversation if you are asking open-ended questions (vs. closed or leading questions). If you invite input from everyone (even encouraging conflict/debate), there is a good chance most of the sides will be represented (including your side). I’m guessing the church asked you to fill this role because they want your influence. Perhaps your involvement will give them the confidence/security that their plans will work out. If that’s the case, you owe it to them to influence away from areas you know are not the best, but it’s always easier if they come to that realization themselves. Even asking permission to add your two cents (or to mention a concern you have) from time to time keeps them in the driver’s seat.

      That’s my two cents, thanks for making me think! Let me know how it turns out.

  3. I love this. These questions can occur quite naturally and organically in a conversation, but they’re targeted well to really get to the heart of the matter. Leadership like this rarely comes with a label of leadership, but more just living out your life as a human being with others.

    • That’s so true, Loren. If I approach someone and say, “I’m a leadership coach. I’m here to help solve your leadership issues, so let’s talk about them.” If I say something like that, it’s abrasive. Being more natural and organic, like you say, makes things a lot easier for everyone.

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