A good friend of mine recently sent me an email asking for advice: “Ryan, I am in the process of hiring a few management positions. I have eight candidates lined up. What questions do you ask to hire great leaders?”

Below are some of my thoughts on: 1) The art of the interview 2) Knowing what you’re looking for, and 3) Understanding why you’re asking every question that you do. Prior to running the leadership advisory practice at Brixey & Meyer, I worked with large international corporations for 12 years in a variety of leadership roles. I’ve interviewed 500+ candidates for many different positions. Additionally, on my podcast The Learning Leader Show, I’ve interviewed 250+ of the brightest leadership minds in the world to better understand how we all can sustain excellence over an extended period of time. My thoughts have been formulated based on my personal experiences and the conversations on my podcast.

What Are You Looking For?


First – What are you looking for? What questions should you ask based on that answer?You’ll need to create this for yourself and it should evolve as you learn, make mistakes, have success, etc… And like a great stand up comedian, have a purpose for every word that you utter in the interview. Don’t “just ask questions” because that’s what you do in an interview. Ask questions that tie back to the qualities you are looking for…

What I Look For In A Leader


  • Self-Aware – Most people do not have this. Do they really know themselves?Strengths, weaknesses, etc. Are they able to express this intelligently?
  • Intellectually Curious – Will the person continue to improve/grow/adapt/evolve?What questions do they ask on a daily basis? How do they try to solve problems?
  • Well-Read — In my experience, people “who don’t have time to read” typically aren’t as successful long term as those who make the time.
  • Optimistic – Do they have the right outlook on life? Or do they think “with their luck” it will rain every day? The leader sets the tone for everyone.
  • Humble – Do they use the word “I” a lot instead of we? Do they blame others when things go wrong and take credit when they go well?
  • Thoughtful – Do they actually think? Do they take time to pause, reflect, learn, and improve? “The learning comes in the moments of reflection.”
  • Great Communicator – As a manager you need to communicate effectively across many spectrums – speeches, emails, working with colleagues and clients…
  • High Energy/Likable – Ideally, the team will like their boss AND respect him/her (my Dad is very good at this). High energy and likability are a good thing. Remember, people don’t leave companies, they leave their manager. Also, it’s hard to be a good teammate (with colleagues) if people don’t like you and/or you bring no energy to the room.
  • Confident – Not cocky, but sure of oneself. I like someone who has put in the necessary work to confidently trust in themselves to make good decisions.
  • Courageous – Have they fought through tough moments in their life? Are they able to make tough decisions when there isn’t consensus? Being a manager is a hard…

Some Questions I Ask (notice each question is tied to the qualities I’m looking for)


  • What is your process to learn something new? I don’t care what they are learning about (an instrument, a second language, historical people). I want to ensure that they have some sort of a thought process towards learning. The best leaders in the world are constantly learning. They strive to improve on a daily basis. If there is no process in place (even as simple as, “I love to read fiction books to boost my creativity” is better than a candidate who has no process to improve). And always ask for examples.
  • What books have you gifted the most to others? OR What books have influenced you the most? Why? (“In my whole life, I have known no wise people who didn’t read all the time — none, zero.” – Charlie Munger)
  • (Start, Stop, Continue Exercise) What should you do more of (start), what should you stop doing (stop), and what is one thing that you’ve really figured out and should continue doing as a leader (continue)? This is a hard question and I don’t expect them to be perfect. Even great leaders will struggle doing this off the cuff… I actually like it when the candidate pauses and thinks for a little bit. It shows they have the confidence to really think and they don’t feel the need to instinctively say something. Hard questions will come up throughout the person’s life as a leader/manager/coach… I want to know how they will respond in those moments. I want someone measured, self-aware, thoughtful. It shows security in oneself. That’s good. If they rush it and say something like “I need to stop working 18 hours a day” then that is a red flag. Ask follow up questions to dig deeper and understand the implications of “their stop.” “What are the implications of you working 18 hours a day?” “Why do you do that?” — Asking why as a follow up typically helps the conversation go deeper. “Approach each conversation with genuine curiosity.”
  • What questions do you have for me? Sometimes I start the interview with this or do it in the middle. If they are intellectually curious, they won’t need to get out their binder and ask the pre scripted questions. They can ask the natural questions that should be in their mind. – Additionally, I love the candidates who ask me questions without any prompting (and this is something I always do when I’m being interviewed). I like the confidence and the curiosity of someone who is willing to ask questions whenever they come to mind. I want candidates who view this as a two way street. If the candidate is strong, they probably have options. They should be interviewing me just as much as I’m interviewing them… My best hires over the past 10 years have done this.
  • How would your closest friends describe you? How about your colleagues? I’m looking for some self-awareness… Every adjective named shouldn’t be positive. Does this person really know themselves? Great leaders have high levels of awareness (both self and situational awareness).
  • What are the commonalities of the greatest professionals you’ve worked with? – I want to know who they will be looking to hire… Hiring is the most important aspect of being a manager. Have they thought about this? I hope so…
  • What are the common traits of leaders you know who have sustained excellence? Why do you think those qualities make up a great leader? I’ve found that a lot of candidates start describing themselves because they assume they are a great leader. I hope that they are striving for something… That they realize “they haven’t arrived.” Additionally, ask for examples of the people they’re talking about. Maybe it’s a great boss, or someone from a book they’ve read. Ask why, why why…
  • How will you build a great culture? Can you define what a great culture is? I’m genuinely curious about this. Maybe they can help me learn… Primarily looking for someone who has thought about culture and how to build a great one.
  • Can you share an example of when you made a big mistake? What went in to that decision? Why did it go wrong? How did you respond? What was the result?Self-awareness, courage, humility – Looking for all of those qualities with this question… Also, if they start blaming other people during the course of this answer = red flag. As the leader, don’t blame others when things go bad, take ownership.
  • Can you share the process for the last big purchase you made? This question is to measure thoughtfulness and for me to learn how they make big decisions. Do they do a lot of research before buying a car? Do they negotiate with the sales person? As a manager, they will need to make big decisions. I want to learn about their process for doing that… Again, if they do not have a process for this = red flag.
  • Find ways to “simulate” experiences they will have on the job. Do micro role plays with them to see how they handle situations. (Conflict; tough decisions; personal vs. business tough decisions; etc).
  • Ask the candidate to share what they have done that validates they are an excellent communicator – public speaking; writings – this is one of the most important business skills. Sometimes I ask them to give me a 3 minute speech on a favorite topic of theirs – something they are passionate about (sports team, vacation, spouse, kids, etc.) – I want to actually hear them as if they are speaking to a group on a subject for which they have passion (as I will need them to do this every day in their job).
  • I need to get an understanding of what kind of teammate they will be for their colleagues – Seek real examples of the candidate being a great teammate (charity work, prior job, sports, church, etc.).

Additional Thoughts…

The greatest interviewers ask great follow up questions. They are active listeners. They do not “just wait to talk,” but they genuinely listen and if an answer sparks something in their mind, they dig deeper. Interviewing people on The Learning Leader Show every week has really helped me develop this skill. As an interviewer, this is something to think about.

Be okay with silence. Roger Dean Duncan shared a great anecdote that he learned from Jim Lehren: “He urged me to ask a good question, listen attentively to the answer, and then count silently to five before asking another question. At first that suggestion seemed silly. I argued that five seconds would seem like an eternity to wait after someone responds to a question. Then it occurred to me: Of course it would seem like an eternity, because our natural tendency is to fill a void with sound, usually that of our own voice.” Lehren explains: “If you resist the temptation to respond too quickly to the answer, you’ll discover something almost magical. The other person will either expand on what he’s already said or he’ll go in a different direction. Either way, he’s expanding his response, and you get a clear view into his head and heart.”

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Ryan Hawk runs the Leadership Advisory Services team at Brixey & Meyer. He works with clients all over the world to help them be more effective leaders, managers, and coaches. He’s learned the commonalities of sustaining excellence from interviewing 250+ of the most thoughtful leaders in the world on his hit podcast, The Learning Leader Show.