The Duck and the Butterfly: Natalie Michael


If you’re trying to improve yourself or boost the value of a team meeting or energize a strategy session, you simply need to ask the right question. That’s Natalie’s super power. She asks leaders the right questions. For the last 15 years, Natalie Michael, author of The Duck and the Butterfly, has coached hundreds of executives all over the world with clients in Fortune 100 companies to entrepreneurial startups.

In this episode, Natalie shares her most powerful coaching questions to help you lead your life, lead others, lead organizations and create a positive difference in the world.

By the end of this episode, you’ll know what to ask to change people’s lives for the better.

Natalie Michael: I came into the coaching field after a career in the tech space. Specifically, I had what everyone would have thought was the dream job. I was the VP of HR for this fast growing tech company. We were changing the world, traveling the world, and on the outside, everyone would have thought, wow, what a success.

But on the inside, I wasn’t feeling very fulfilled.

So I was in a bit of a dilemma, because on the one hand, I knew that I was in this high flying career, but I also had a lot of stock options. I knew that one day, in this job, I had the potential to make millions.

The dilemma was, I wasn’t happy.

So I made a pact with myself that I was going to make a career change but I had to really make a move that was so deeply fulfilling that when I open the newspaper down the road and I saw that yes indeed, we achieved everything that we knew that we were capable of in this company, that I wouldn’t regret having left and not making millions as I knew my colleagues would.

That moment came a few years ago when this company went public, and I indeed had no regrets. I was very happy I went into coaching.

But the coaching field has not been an easy road. One of the toughest parts of being a coach is actually coming up with really good questions.

“You realize pretty quickly that when you have a good question, it can really change someone’s life. “

This book is really a toolkit for any new coach who wants to be transformational in their coaching, whether you’re a leader or you are an actual professional coach, it gives you a whole toolkit of questions that aren’t just good questions, they actually are transformational questions that can have the impact for changing lives or teams.

Learning to Ask Good Questions

Charlie Hoehn: Why is the book titled The Duck and the Butterfly?

Natalie Michael: The nuts and bolts of this is, when you ask a good question, you’ve got to remember to shut the duck up and really listen to the answer.

The butterfly is a reminder that every question, if it’s delivered in a certain way, has transformational potential.

Throughout the book, you have ducks (listening tips) and butterflies (tips for how to deliver a question). It actually opens up the person you’re talking to rather than hitting them like a sledge hammer.

Charlie Hoehn: Can you kind of guide us through some good questions that coaches can ask?

Natalie Michael: Yeah, well, first off, if you are a new coach, an executive coach specifically, a leader, or just somebody who wants to self-reflect, this is the book for you.

The idea is, if you’re a leader in a business, and you’re walking in to a one-on-one coaching session, a team session or a strategy session, you can flip open this book and come up with some great questions for the coaching session or the meeting. It will open up a new, more thought provoking conversation. Just want to set the stage there.

The idea of leading your life is that all of us want to be more intentional about how we’re living our lives, the value we’re living, what our purpose is, how we’re going to create more wellbeing and authenticity in our life.

“These are questions that all of us can whip open and journal.”

They’re questions that we can ask of others to really help them on that path of self-actualization and fulfillment.

When I was writing this book, I found that some of the questions just jumped off the page and really spoke to me. I was 45, going through the classic midlife transformation, and I was at a point where I was saying, once again as with the tech company years ago, what do I really want for this decade?

I’m really big into meditation and have been on that path for years, and I find that in this latter half of my life, I’m really curious about what I believe I’m being called to do.

One of the questions that really stood out for me in the book is what is spirit calling you to do? What goals do you have that feel like a mission or a calling?

I’m also a parent with a 10 year old child, and a question that was really important for me was what career opportunities are available? In line with who I want to be as a parent, that was really important.

Getting Clear on Purpose

Charlie Hoehn: What career opportunities did align? I take it was the coaching itself.

Natalie Michael: Yeah, for me, I wasn’t going through a career change, I was going through a kind of that delightful phase of “Wow, my career’s going really strong, what are the things I really want to say yes to?”

For me, based on the reflection I did with the book, I realized that part of my purpose is really coaching people who are interested in rising to the opportunities in front of them in their lives, but also using those opportunities as an opportunity for personal growth and transformation.

The ideal client for me, which is something that I got really clear about in writing this book, is someone who is really interested in going deep with themselves and reflecting not only all that they want to do but who they want to be as a person and how they want to grow as a result of whatever challenges are in front of them.

It’s really wonderful to be able to say that with clear language and a real heart resonance, and I believe that it’s hard to get there if you don’t ask yourself really good questions and take the time to reflect.

What is Happiness?

Charlie Hoehn: I like that you highlight, you really bookmark and highlight the ones that really seem to, I take that these are the ones that really help your clients the most.

Natalie Michael: Yeah, they pop out. Ironically, I do a lot of work with CEOs, and one of the parts of my portfolio is I run CEO peer groups. Just yesterday, in one of our peer group meetings, each of the CEOs was presenting their life vision.

The biggest theme was that when leaders really love their work and they love challenges, sometimes they have happiness in one quadrant at the expense of other quadrants like families and friendship and creativity and health.

“Have a more robust definition of happiness.”

Really saying, “Well first and foremost, I want to be healthy and happy, and that comes before work and more work.”

That’s a big mindset shift for a lot for these leaders. It’s not until you get a health scare or some tragedy happens that you wake up to that. It’s a very powerful question.

When Priorities Shift

Charlie Hoehn: I love this question. “If I told you this moment of your life was a turning point, what do you imagine you’d be happy to move away from or move toward?” That’s really interesting.

Natalie Michael: That was a big piece for me because I think so much about success is figuring out what you’re going to move away from or say no to or reorganize in your life.

What I have found is when people are going through big transitions, it’s not like our core values change, but they often reorder or reprioritize.

I don’t know about you, but when I first had my child, I found that all of a sudden, my relationship with parenting and family and how I wanted to relate to that as a human being all of a sudden became much more important.

“It wasn’t that work was no longer important, it just had a different relative importance.”

Understanding how our values may shift in terms of relative importance depending on what life stage we’re at is a big part of figuring out what we’re going to move towards or away from, I believe.

Charlie Hoehn: “To best achieve your biggest goal, what do you need to accept fully about your present reality?” Which is basically, what are you in denial about that’s holding you back from your goal?

Natalie Michael: Yup. I’m not even going to comment on what I had to face in looking at that but let me just tell you, it is a hard question to answer.

You know, it’s interesting that you say it’s fun to flip through because it’s also fun for dinner parties.

Part of what I will do with parties, I’m quite famous for this now, is at the dinner party, I write this questions on index cards and then with each meal at the table we’ll tackle them and talk about them.

It really does provide for a fun, thought provoking evening, and I learned that it’s best not to have all the deep ones. You’ve got to have some fun ones, otherwise your dinner party can get pretty heavy pretty quick.

Your Purpose in the World

Charlie Hoehn: What kind of results or what kind of transformations, to carry with the butterfly analogy, have you seen that you’re most proud of?

Natalie Michael: Right now, I’m doing a lot of work with executives who are defining their next chapter, and I have to share a moment with you.

Yesterday, in my CEO forum, I gave a copy of the book to CEOs. One of them came up to me and said, “Natalie,” I work with him as a client, he said, “The reason I chose you as my coach was because when we did the meet the coach day, you asked me questions that I absolutely had never thought of and could not answer.” He goes,

“That is what I believe is your purpose in the world.”

I almost started to cry. What I realized is, the transformational moment is the question. Sure, I have written a question book and I have a lot of them at the tip of my tongue, but my hope is that with this book we have an army of all of the listeners and people out there who are asking these questions of other people.

“The transformation fits in all of us, we just need to question. “

I added a bonus part of the book called, Making the World a Better Place, because, like you, I really want our world to continue to evolve in positive ways.

And one of my favorite questions in the book is in that section, and it’s, “If you can write a message that would get through to all of humanity, what would your message be?”

And I’ve used this at executive team retreats, at dinners, for myself. It’s a change the world question but it is a life purpose question. That is powerful.

Charlie Hoehn: What’s been your favorite answer to that question?

Natalie Michael: It’s the diversity in the answer, I think.

I’ve noticed in the older folks it’s around creating the next generation. I remember one executive retreat we ask this question over dinner. For some people it was about ethics, other people it was environment, others was their children, but all of it was around evolving society. So it was jaw dropping actually.

Generational Lessons

Charlie Hoehn: What question have you been asked that has had the biggest change or the biggest impact on your life?

Natalie Michael: As part of this midlife transition, I’ve been really looking at what conflict is like for me and how I respond in conflict.

One of the questions of the book that I really stopped to ponder and had a profound impact was, “If you saw a video of yourself in a conflict to situation, would you look or sound like one of your parents?”

And that was quite thought provoking. It definitely requires you to hold up the mirror.

Sometimes, you just got to go back to that family system and see what you’ve learned. At midlife you think, “Oh my gosh, do I really have to go back and think about that stuff?” And it’s like lo and behold, there is something.

Charlie Hoehn: You have a great question in here along those lines, “What have your kids taught you about leadership?” I am curious about what they’ve taught you.

Natalie Michael: I think right now what my daughter is teaching me about leadership is the art of quiet leadership.

“Sometimes we have this view of leaders who are these charismatic, big personalities. “

But what I see in my daughter is the power of quiet leadership and somebody who is able to really influence others, not from the volume of what they are saying but by choosing their words carefully and asserting their view in a more quiet way.

What’s Your Picasso?

Charlie Hoehn: So you have a question in here that I think I know the answer to which is, “What’s your Picasso?” The piece of work you’re motivated to make a work of art. And I believe and you can correct me if I am wrong is your Picasso is this book because this has been your work for a long time and now, it is a piece of art that is in the world to help people.

Natalie Michael: You got it, and I want to tell a quick story about that question because it is one of my favorites. I was in a coaching session with one of the CEOs in my forums.

She is out to change the world and she is a very inspiring woman and her schedule is crazy. It’s so full of activity and amazing things. And she said every week she looks at her calendar and she says, “What’s my Picasso?”

“She color codes her calendar so those Picassos are clear to her. “

Her mission in that week is to say, “What are the nuggets, those meetings where I am going to show up totally present and let all of my business melt away and just focus on being fully present with who’s in front of me?” I love that.

This book is definitely my Picasso. I actually try to get more tactical and say, “What’s my Picasso today?” This week, this month.

I find it’s a beautiful way to manage your time.

Questions and Conflict

Charlie Hoehn: How many questions are there in total? Did you ever count?

Natalie Michael: Over a thousand. I do want to point out that one of the things that I also do is team coaching. I just was working on a certification in this, and what I have found is that anyone who is charged with building a high performing team, you need to hold the mirror up for the team to really help the team figure out where they are being productive and where they are being unproductive.

And so there’s a whole list of questions that teams can ask themselves as well and I have found whenever I am facilitating team sessions, I go to this section. It’s hard—other than, “Who do we want to be as a team,” right? “Where are we working well? Where are we not working well?”

“If you ask things that are more thought-provoking it can really create an ‘aha moment’ for the team.”

One of the questions that I love with teams is simply asking, “So tell me about the most dysfunctional team you’ve ever been a part of?”

Everyone tells this wonderful story about all of this dysfunctional teams, and I say, “Okay great. Now, tell me how this team is behaving just like those dysfunctional teams.”

They kind of go, “Ah… oh I didn’t know you were going to go there with the question.” But questions like that that had team members just stop and really think.

Some other ones are things like, “Where has this team inadvertently dropped their standards,” “What is the unique value this great team brings to the world? What do you treasure about this team?” Again, things that you can bring for executive meetings.

“If this team conflict was an opportunity to invest in relationships, what would change in the team dynamic?”

I came up with that question because one of the CEOs that I was working with said, “I used to always think conflict meant we were about to break up. Whether they were going to quit or my girlfriend was going to leave me,” and he said, “Then I reframed me as, “Oh wow, if we are engaging in conflict, that means we are actually investing in each other.”

That was a powerful reframe for me, and I think it’s a powerful reframe for teams as well.

Asking Uncomfortable Questions

Charlie Hoehn: So the final question in the book is, “What are the questions that will take you out of your element and out of your personal comfort zone and hurl you into the mysterious unknown?” Why do you think that matters? Why do you think we need to be hurled into the mysterious unknown?

Natalie Michael: Well I don’t know that we need to, but one of the things I encourage people to do with this book is not just answer the questions that appeal to them. The questions that appeal to you are going to reinforce your current level of thinking and consciousness.

I encourage people to ask the questions where they go, “Oh, that’s kind of flakey,” or “Oh that’s a bit out there,” because those are the questions that are going to really hurl you into the unknown.

You don’t know what the answer is going to be, and I just believe that if we want to think more expansively, that there is power in that place.

Charlie Hoehn: Do you have a question that makes people squirm the most? The most uncomfortable question.

Natalie Michael: I don’t know if this makes people squirm but I do find that it’s a question that has people go, “Oh, hmm,” and that’s, “Where would you like to be more mature?”

I think we all have that little kid or that scrappy teenager in us. It just kind of evokes the wise adults and it usually has people stop and remember that, “Oh yeah, there is a choice here.”

A Challenge from Natalie Michael

Charlie Hoehn: Can you give our listeners a challenge, maybe one question or something they can do from your book that you really want them to do this week that can improve their life?

Natalie Michael: Well other than ask themselves a thousand questions, I think that getting the book and asking two questions from the personal section of the book is a very powerful exercise.

Barring that, I think that I will leave people with a question in the “change the world” section: “What is your role in making the world a better place?” Answer that question.

Charlie Hoehn: How can our listeners connect with you and follow you and tell you thanks for the episode?

Natalie Michael: Well, I think the best thing is to pop me an email. I’m just in the process of getting all of the social media set up, so keep your eyes open for Duck and Butterfly on Instagram and Twitter, which is going to be coming up in the next week.

In the meantime, just pop me an email. I would love to hear what resonates with you or what you do with this book. It’s [email protected].