Why Asking Good Questions Can Help You Be a Better Leader

Guest Post by Melissa Dawn

At the end of a long workday, many of us feel drained and unfulfilled. This is because we spend our days sliding into problem-solving or Rescuer mode. That might sound… like a good thing? Like that’s what we’re supposed to do at work? Especially as leaders?

Sure, problem-solving is great, but there are two big problems with the Rescuer mindset:

  1. Constantly sliding into the role of Rescuer is exhausting and a path to burnout.
  2. As leaders, we may get things done in the short term this way, but we sacrifice the long term by missing countless opportunities to coach the people we lead to develop their own problem-solving muscles.

Instead of problem-solving mode, try question asking mode.

Why is Asking Questions Important for Leaders?

The benefits of leaders asking powerful questions are far-reaching. Essentially, questions empower people.

When your default is Rescuer mode, you sap your own energy, disempower yourself, and impede the empowerment of others. The growth of yourself and those you lead gets stalled. Everyone becomes disengaged from the bigger picture, and ends up feeling like they’re stuck in a hamster wheel, constantly running, but never getting anywhere. Burnout city.

In my post on the Triangle of Disempowerment, I talked about empowering yourself by shifting your narrative into a story of you as the Hero. Not a hero who saves everyone else, but the Hero who accepts circumstances for what they are in the moment, in order to create real, sustainable change moving forward.

A true Hero also believes in the capabilities of those around them, drawing out the brilliance, strength and courage of others by trusting that those qualities already exist and are just waiting for the opportunity to spring into action.

Asking questions is a huge part of this. The Hero is always curious. He or she always wonders, what else is possible? What can I create from this? How can this get even better? The Hero approaches every interaction from a heart of peace – a heart that is open and accepting, leaving judgement behind. The Hero sees a problem and confidently turns to the people around them to ask, “What do you think?” Because even when the Hero can see a solution, they know they gain more by hearing different perspectives, and that the growth of the people they lead is the higher priority with the bigger long-term payoff.

Questions From a Heart of Peace

Coworkers chatting As leaders, our role is to create a safe space for people to come and talk to us. They have to have trust that they will be heard and validated; that what they have to say will be met with openness, not judgement.

Of course, we can’t control how others feel or behave. What we can control is how we show up and the intention we bring to our roles. We have to trust that the people around us are naturally creative, resourceful and whole, and believe that their insight is both valid and valuable.

I’m often asked, “Why is questioning a good leadership skill?” The biggest part of my answer is that by asking questions, most of the time, people come up with the answers themselves and feel both empowered and that their contribution has value. And isn’t that our main goal as leaders? To empower others?

When our default communication approach is one of curiosity, the people we lead practice – on a daily basis – how to think and how to bring their truth forward with confidence, so that when you are not there, they will ask themselves the questions that bring out the answers and solutions for themselves.

In this way, you aren’t constantly rescuing people and situations. Instead, you are “teaching them to fish”; you are facilitating their shift into the Hero of their own story, driving their empowerment, which drives creativity, ingenuity, confidence, collaboration, engagement and so much more.

What is a Powerful Question?

rubber duckling

A client recently taught me about rubber duck theory in software programming, and it’s a great example of both the power of asking questions, and how the simplest questions can be the most powerful.

Rubber duck “debugging” (solving problems in software code) refers to a story of a programmer who would keep a rubber duck nearby and explain each scenario to the duck, bit by bit, as they were going through the code. You see, the solution was usually found within the problem itself, and simply by talking it through, the programmer was able to get the clarity needed to move forward.

By asking even the most basic questions – “What are you experiencing? Describe it to me, step by step.” – with genuine curiosity and not a hint of judgement, people not only get the opportunity to talk through problems, they also develop their own inner dialogue to begin asking themselves questions and creating solutions independently.

As a leader, you are the rubber duck. You are safe, curious, open, non-judgmental, and eager to listen. You are the most impactful type of Hero, guiding others to step into their own heroism.

Colorful paper planes

What Are Some Good Leadership Questions to Ask?

As a general model, aim to keep your questions specific and open-ended.

Why specific? It comes down to fear and habits. If you ask a question such as, “How is that project going?” most people will reply “Fine” out of habit. They may also feel intimidated giving their overall impression of something. It’s a lot easier to give an honest impression of a specific part of something. That may sound like, “There’s something interesting in the second phase of this project, right here. What are your thoughts on it?” From that more specific question, the conversation is far more likely to flow into more openness and honesty.

Why open-ended? You want to get people talking. That’s when creativity and problem solving really happen. A close-ended question is something like, “Are you happy with this outcome?” It’s closed because the answer can easily be yes or no, and that’s the end of the conversation. With open-ended questions like, “What are your thoughts on this outcome?” or “What opportunities do you see from this?” or “Where do you see us going from here?” you have a better chance of getting people talking.

Here are some examples of powerful questions to ask someone, that you can modify per your needs:

  • What do you really want?
  • What about this is important to you?
  • What does that look like?
  • How do you feel about this?
  • What’s next?
  • What else is possible?
  • What’s right about this?
  • What are your concerns?
  • What is standing in your way?
  • Tell me more?
  • What do you need most right now?
  • What is the worst-case scenario? And what if that happens?
  • If I knew nothing about this, how would you explain it to me?
  • What opportunities do you see?
  • What is the vision you want to create?
  • What are you choosing?
  • How are you experiencing this?
  • What are you aware of right now?
  • Imagine you say yes/no, what comes up?

How to Hold Safe Space for Great Questions (and Answers)

People need a safe space to unload and to explore. They don’t need, or really even want, someone to swoop in and save them. They simply need to be heard and to have a safe sounding board.

Here’s an example of what holding safe space could look like:

  • “You seem to be struggling. What’s up?”
  • “This client is asking for the impossible. I just can’t see how we can make this work!”
  • “Hmmm. That does sound challenging. What do you feel is most important here?” 
  • “I suppose that would be…”

This scenario has three key elements of impactful communication: curiosity, validation, and an “us together” mindset.

At no point are we offering solutions or downplaying the struggle. In this scenario, we are fully open, ready and willing to listen, reflect back and hold safe space.

Giving people advice from your perspective may not be the right path for them. Maybe, in certain situations with certain standards, you might have more experience. However, as a leader, your role is to guide people in coming up with the answers for themselves so that they can develop their level of experience.

If you have the answer, that’s great. Hold it in. It’s not going anywhere. Even if you open yourself up fully to other possibilities, that solution in your mind still exists. To truly hold safe space, hold yourself in the knowledge that you risk nothing by hearing someone else first. Your ideas are valid AND your priority is to create space for others to grow and explore their ideas.

Holding Safe Space Means Being a Safe Space

Guy walking with his dogThe real magic happens when we, as leaders, embrace the opportunities for our own growth alongside the growth of those we lead. This is part of why questions are a powerful tool for leaders. Being a safe space for others is no easy feat. It demands kindness towards yourself first and foremost. It demands caring for your whole self and establishing healthy habits that keep you grounded and connected.

I am a big believer in an intentional morning routine, as well as a strong connection with nature. Here’s why:

  • An intentional morning routine that’s focused on tuning into your leader within empowers you to decide how you will show up each day before anyone or anything else can influence you.
  • Regular contact with nature keeps you connected to your larger role in the Universe as well as the bigger picture in your life. It empowers you to practice certainty in even the most uncertain situations.

Remember, you can’t pour from an empty cup, and filling your cup isn’t just so you can serve others. Be intentional, purposeful and habitual in filling your own cup and in serving yourself first – i.e. treating yourself with kindness and curiosity – and you will be in a far stronger position to be of service to others. You will be empowered to lead from your best self, which will have a domino effect on those around you, influencing them towards greater self-leadership as well.


When You Feel Like Giving Advice…

The focus of asking questions is about getting people involved in decision-making and problem-solving. This gets people exercising their critical thinking muscles so that they are better equipped to self-lead. It makes people feel valued, heard and recognized when they are proactively brought into the fold. They feel that their contribution is meaningful, which makes them more engaged, creative and at ease in their role.

Essentially, questions are about the other person. It’s your opportunity to exercise your listening muscles.

When I was going through my coach training, one of my teachers told me, very firmly, “When you feel like giving advice, take a deep breath… shut the f*ck up and ask a question instead.”

Putting this into practice was hard. It was almost like learning a new language! When someone would open up to me or bring up a problem, it was an almost unconscious reflex to offer advice. I wanted to help! But advice, unless it is explicitly asked for, doesn’t help anyone. In fact, even when it’s explicitly asked for, I now start with a question first and see where that leads us.

What I’ve had to learn is that people don’t need solutions. They need safe space and they need to be heard. Even when the solution seems so simple to you, take a deep breath… well, you know the rest 😉

When you really want to give advice and truly feel it would help move things forward, ask first. Try, “I can give you some advice around this, would you like to hear it?” By you asking and them saying yes, they’ll be more open to hearing you. If they say no, listen.

Questions Create Better Conversations

Time and again, clients tell me they keep leaving business conversations without saying what really needed to be said, or without getting what they needed from the other person. As I’ve written about before, a lot of that comes down to fear. However, another big part of it is that too many of us listen to respond instead of listening to really hear.

You don’t need to be a coach to be a great listener. You just need to commit to asking better questions. Especially in leadership or mentorship roles, asking powerful questions is an invaluable tool for bringing out what needs to come to the surface. It opens up possibilities, strengthens relationships, and really gets people engaged with their full contribution within the organization.

Taking it Further

Asking questions is a communication tool, which really makes it a relationship tool. After practicing it as a coaching and leadership technique, I began bringing it into my personal life as well and I’ve experienced some wonderful shifts in the relationships that matter most to me, and in how I interact with people on an everyday basis.

I also use powerful questions with myself. Good leadership is about asking good questions, and that extends to self-leadership. Whenever I feel stuck, I ask myself, “What else is possible?”

If you would like guidance in developing your leadership skills – including asking great questions – I invite you to connect with me. If you are open to a bit of advice from me… I highly recommend this workshop from the Co-Active Training Institute.

And now I have to ask you… What’s next?

Good News from Bob: If you missed the one-hour Webinar with Dr. Michael Marquardt and myself, hosted by Becky Robinson, sharing “How Leaders Find POWERFUL ANSWERS BY KNOWING HOW AND WHAT TO ASK” from the just released 3rd Edition of “Leading With Questions” click HERE

Melissa Dawn


Melissa Dawn is a renowned speaker, author and coach certified by the International Coach Federation as a Certified Professional Co-Active Coach (CPCC), a Professional Certified Coach (PCC), a Certified Team Performance Coach (CTPC) and a Conscious Business Coach. She holds a Bachelor of Commerce (BComm), is a regular contributor to the Huffington Post, Thrive Global and Entrepreneur and is regularly featured on top podcasts, radio and television programs. She is the author of the bestselling book, I Attract What I Am – Transforming Failure Into An Orgasmically Joyful Life & Business, and was named one of Hubspot’s Best Coaching Services worldwide for 2019, 2020, 2021 and 2022.  You can connect with Melissa @ CEOofYourLife



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