Coaching Questions to Help You Make Breakthroughs at Work and in Life

I get a version of this question regularly: “What are the 3-4 coaching questions or exercises most likely to produce breakthroughs?”

I get where it comes from. What if you could boil coaching down to powerful questions anyone can ask themselves anytime they’re looking for a breakthrough? 

Coaching doesn’t work like that. Coaching is a dance between the client and the coach, with longevity as a key ingredient in producing breakthroughs that last. 

The key ingredient in these breakthroughs is not the questions that are asked (although they matter) or the desires of the client for that breakthrough (which also matters), but the space the coach holds for the transformation to happen. 

It’s the suspension of judgment. The radical acceptance. The openness to whatever the client has to say. To whatever might be at the root of the current blockage. And in nearly every case I’ve encountered so far, what’s at the root of any big blockage is an uncomfortable emotion left unacknowledged, unprocessed, and unintegrated. 

So let’s set out to do an impossible task: produce breakthroughs with questions in the course of a blog post. But let’s make our goal slightly more realistic: let’s open the door to the possibility of breakthroughs in the future. To do that, I want to give a canvas of what holds us back as entrepreneurs and an intro to the questions and exercises that drive breakthroughs. 

What Holds Us Back: The Six Categories of Emotional Blockers for Entrepreneurs

At first, many entrepreneurs believe they just need the right tactics or knowledge in order to make a breakthrough. And sometimes this is true — especially when you’re just getting started. 

But I see a consistent pattern in the entrepreneurs I’ve worked with. They have almost always consumed every book, article, podcast, or YouTube video they can find on how to make the breakthrough they’re looking for. Often they’ve tried almost every tactical approach they can come up with. Sometimes they’ve burned their teams out by initiating new project after new project to try to find the one that will work.

When they show up to our first call, they feel like they’ve tried everything, but they’re still not making the progress they want. Some are ready to give up or give in. Some are willing to try ANYTHING — even coaching! — to get over the hump. And sometimes they tell me they’re absolutely operating on all cylinders but there are just a couple things that need tweaking. 

In all of these cases, most entrepreneurs know what they should do to keep growing as leaders and as a business, but they struggle with the emotional cost of doing what they know needs to be done. Acknowledging, understanding, and integrating those difficult emotions are the crux of what creates breakthroughs. 

This is a framework around the six categories of emotional blockers I see entrepreneurs face. I’m certain I’m missing something — this can’t possibly be complete. But it is useful nonetheless. (Shout out to Brene Brown’s Atlas of the Heart for serving as an excellent reference and inspiration for this framework). 

In each category, I’ll share the emotions that make up the category, a quick anecdote to illustrate the point, and one or more coaching questions or exercise to help open the door to the deeper work to be done.

Challenges of Clarity

When I host workshops on this same topic, challenges of clarity are the most commonly shared experience amongst entrepreneurs in the room. Choosing a path forward given the infinite possible outcomes and the uncertainty of how something might feel once you get there is a serious challenge for folks in charge of their own destiny. 

Three core emotions:

1. Avoidance – this is so challenging that I choose not to make a choice rather than confront the uncertainty; being comfortable where I am is better than being vulnerable to an unknown outcome
2. Confusion – I’m getting conflicting signals and information, from inside of me and/or from external sources; I don’t know how to choose from the options available to me
3. Doubt – I think I know what to do, but I don’t trust myself to make the call; what if I’m wrong? What if I’m not qualified? What if people call me out for bring a fraud?

An example: One client spent seven years building a business with a well-recognized and respected brand in a very specific niche. It had margins any entrepreneur would dream of, good growth, a dedicated team, and the entrepreneur still enjoyed the work for the most part. They received an offer to sell the business for an amount that would  give them financial freedom for life. They experienced deep inner conflict over what to do – keep growing the business doing what they love or sell and move into the unknown?

Coaching exercise:

Writer’s note: I fully recognize how “woo-woo” this exercise may feel. All I can tell you is that it is the most effective exercise I have done to uncover my inner emotional landscape and I’ve seen it work repeatedly in 1:1 client work and in workshop settings.

If you’re experiencing inner conflict: close your eyes and take one or more deep breaths; clear your mind by focusing on your breath and take a moment to let your body feel fully supported by the chair you’re in. Imagine the emotion you’re feeling related to the decision in front of you. 

Now picture where in your body it lives — it might live in more than one place or part. Imagine traveling all the way to the root of the emotion(s) in your body. If there are multiple, start with one. 

See if you can envision what that emotion looks like inside of you. Describe it in detail. Now, say hello to the visual, welcome it, and ask what it wants you to know. Try your best to accept whatever it has to say without any strong reaction. You’re just making room for what’s going on for it. Ask if it has anything else it would like to share.

Repeat this process for any other places or parts that are feeling emotion related to the decision or situation that’s driving a lack of clarity.

Take a couple more deep breaths and then open your eyes. Make some notes about what you learned about your inner emotional state and what the different parts are telling you about the conflict you may be experiencing. 

Now, try to get centered in the adult, capable you. Knowing that the adult you is capable of handling new situations and the emotions that come with them, what is the path that seems most aligned with what you most authentically want? Are you willing to accept the emotions that come with that choice?

This exercise is loosely based on the Internal Family Systems framework created by Richard Schwartz and is commonly referred to as “parts work.” There’s a deep rabbit hole you can go down here if you find it useful. 

Challenges of Criticism

So many entrepreneurs have raging inner-critics. Those critics are exceptional at driving performance from a place of insecurity and judgment. And they’re also a sure path to emotional burnout.

Three core emotions

1. Shame – “the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love, belonging, and connection.” – Atlas of the Heart, pp 137; This can show up like “I failed; I’m a piece of shit; I knew it all along.” Or “If anyone knew this about me I’d be ruined.”
2. Guilt – what we feel when we have a standard or a set of values, we fail to meet it or live up to them, and we want to make it right
3. Self-criticism – the process we use to evaluate our own performance; sometimes tied to perfectionism or unrealistic expectations of ourselves; this can turn into a Sisyphean prison that requires us to work harder and harder with no end in sight

Two quick examples here to illustrate:

I have lived my whole adult life attempting to be morally perfect in the eyes of others. If anyone catches me slipping on my own standards or not living up to the values I say I hold AND says it to me before I can catch it myself, I slide straight into shame. My inner critic comes out swinging, with harsh evaluations of everything I did wrong to let someone else catch a mistake before I did.

Separately, a client has had challenges with staff turnover on their team. Each time a teammate leaves, they experience it as proof that they are unworthy of being loved and cared for. Two things happen as a result. The first is that it prevents them from accurately evaluating what is really causing employee turnover (lack of candidate-job fit; mismatched expectations; better pay in a new job; etc). The second is that they slowly but surely shy away from hiring anyone at all to avoid the pain.

Coaching questions and exercises

Exercise one: Think of a recent situation in which you felt shame or your inner critic was raging. 

Whose voice is represented in the shame or criticism? Is it yours or it someone else? Perhaps a parent or family member, former boss or colleague, a teacher or classmate? If you separate your adult self from that other voice, what do you see differently about the situation?

Exercise two: Think of a situation in which you felt guilty because you didn’t live up to your own standards. What value do you hold that you’ve compromised or fallen short of? 

What does this teach you about what matters to you? What were the underlying emotions or other contextual details that led to you falling short of what matters to you?

Challenges of Comparison

We’re all subject to comparing ourselves to others, but I find that entrepreneurs are particularly prone to this category of challenges. The very qualities that make entrepreneurs likely to start companies are the ones that make us sensitive to comparison. We’re different by nature and choice — it’s a feature, not a bug — and yet we still look around at who raised more money, who’s growing faster, who won the award or got the recognition.

Three core emotions

1. Jealousy – that person is a threat to me having what I want; I’m worried they might take something or someone away from me
2. Envy – that person has something I want and I wish I could have it too
3. Resentment – that person has something I want and they don’t deserve it as much as I do; the injustice of this reality pisses me off

An example here comes from a client of mine who has spent decades building deep expertise and pursuing professional certifications to become one of the best qualified people in their field. As they look around at other people running businesses in their industry, they see people who are less qualified but earning substantially more money. It sparks both envy and resentment — they want what the other entrepreneurs have, but it also feels unjust for a less qualified person to be more “successful.”

Coaching questions and exercises

Exercise one: Think about a person who sparks resentment for you and ask: what in me do I despise, reject, or feel embarrassment about that is reflected in this person?

Exercise two: Think about a person who sparks jealousy or envy and ask: What does this person have that I want but haven’t yet admitted to myself?

Challenges of Catastrophe

Sometimes things go wrong. Sometimes we are scared of things going wrong. Sometimes we convince ourselves things will definitely go wrong, even when that’s not likely. 

Three core emotions

1. Fear/dread – leaning on Atlas of the Heart again for a couple quick definitions: “Fear is a negative, short-lasting high-alert emotion in response to a perceived threat.” “Dread occurs frequently in response to high-probability negative events; its magnitude increases as the dreaded event draws nearer.” Fear is a response to immediate threat; dread is anticipation of a coming threat. 
2. Anxiety/Worry – I don’t know what might go wrong, but something might go wrong and I need to stay vigilant to try to avoid it; often feels like a version of: what if I fail, then my business falls apart, then I can’t support my family, then we end up homeless?
3. Despair – my fear or worries have come true and now I feel hopeless and sad in the face of the challenges ahead

Two examples are helpful here. In the first, a client is starting a new business. The beginnings are humble and it will take time for it to grow into something substantial and impressive. They worry about family finding out about the business. Will they think they are irresponsible, naive, and incapable of providing for their family? Will they be disowned or shunned from the family as a result?

In the second, a client had an underperforming teammate who was consistently causing issues with peers and customers. At the same time, the teammate was customer facing and had strong relationships with certain groups of customers. My client worried that by firing the teammate for lack of performance, they might make customers angry and somehow lose a huge chunk of revenue as a result. 

Coaching questions and exercises

Exercise one: What is really at stake here? 

Sometimes when we are feeling fear or worry, we don’t realize that we’re attaching a current situation to an unrelated outcome that we can compartmentalize with a different approach. What outcome are you attaching to your current decision or path that could be separated with a different approach or mental model? 

Returning to the example above, how could you both start a business and gain the support of your family member — is it actually true that starting a business will lead to disappointment, or are the two factually unrelated? 

Exercise two: Take a moment to consider the circumstances you fear or dread. Play the situation all the way out. “If I do x, what is the worst possible outcome?” Spell out every detail of what could go wrong. 

Now take a moment to get centered by closing your eyes and taking 10 deep breaths; you can even consider leaving the worst case outcome for a couple of hours to take a walk or do something that you enjoy. 

When you come back to it in a minute, an hour, or a day, ask yourself: from a place of confidence in my own ability to navigate the world and care for my own needs, what is the likelihood or probability that the worst case will come true? Given that likelihood, what are the other possible outcomes and how likely are they? 

You’ll often find that other, better outcomes are much more likely to occur than the worst case you have in your mind. Once you’ve outlined the possibles outcomes and their probabilities, ask yourself: am I willing to risk the negative outcome in order to have a much better chance of the good outcome?

Challenges of Conclusion

Sometimes things come to an end. In fact, all things eventually come to an end. A business needs to close. Your board removes you as CEO. You need to leave a job or you’re fired. A loved one passes away. You move cities.

All of these situations come with loss — even when they generate forward motion that turns out to be positive for our lives. Too often, endings go unprocessed and wreak quiet havoc on our bodies and minds.

Three core emotions

1. Sadness – the natural feeling in response to loss of something important to us or failure in something that matters to us
2. Grief – the deep challenge to our sense of meaning created by loss and the experience of trying to put our world (and our sense of meaning) back together in response (adapted from a definition by Robert Niemeyer found in Atlas of the Heart
3. Disappointment – the feeling we get when what actually happens falls short of what we hoped or expected to happen  

So much entrepreneurial advice comes down to some version of “keep going.” And in many cases I agree, you should keep going. But not without processing the hard shit that happens along the way. Sadness, grief, and disappointment are all vital aspects of living a fully human life. Repressing them in an effort to avoid suffering does nothing but prolong that suffering.

Transforming our negative perceptions of these feelings that every person will experience is a critical skill for building the resilience necessary to survive, grow, and thrive as an entrepreneur.

An example here comes from my own experience leaving my role as COO at ConvertKit. After five years at the company and playing a vital role in helping to create a strong culture and grow our revenue, I felt a loss of identity and meaning in my life. This is despite the fact that I had a beautiful wife, a young son, and a second son on the way. I was experiencing sadness over what I had lost, disappointment over all we had not achieved that I had hoped to achieve, and grief over my lack of direction and purpose. It took me over a year to begin to heal.

Coaching questions and exercises

Exercise one:If you rarely feel sad or have a hard time processing sadness, this is for you. 

Think of the last time you were sad. For many people, your initial reaction might be to say “I don’t remember a time that I was sad.” This is an excellent clue that challenges of conclusion are an important opportunity for growth. 

Consider taking a moment to sit somewhere outside. Take deep breaths until you can notice where in your body you are carrying tension or stress. Breathe into those spots. Now, from that place of centeredness, ask yourself again: when is the last time I felt sad? When has someone let me down? When did I lose something that mattered to me? When did the world reveal itself as broken in a way that hurt?

It’s possible you might end up with a long list of past events that sparked sadness. This is good. Now choose one. Take a deep breath. Now, out loud to no one but yourself, describe the situation as you experienced. When you’re done, say “When that happened, I was sad.” And then sit in silence for a full minute. 

Take time to notice how it feels in your body.

Exercise two: Using ritual to process endings, loss, and grief.

Think of a time when something that mattered to you came to an end. Describe the situation in detail out loud or in a journal. What specifically ended? What is every element of your life, personality, work, or relationships that came to a close?

For example: I am no longer the COO of ConvertKit. I no longer make a salary of $xx. I have no more decision making power over the future of the company. Etc etc. 

Now, reflecting on all that is ending, ask yourself:

• How does each ending make you feel? 
• How would continuing on in that role/business/relationship/city have kept you small?
• What am I ready to let go of as I move beyond this ending?

To take this one step further, consider incorporating a ritual involving fire, water, or earth. Choose which element most resonates with you. Build a fire, go to a body of water, or go into nature (your yard, the woods, a park, etc) and dig a hole. 

Write each ending on a slip of paper or other material that will naturally biodegrade in water or the earth. Take time to read each ending out loud and place it in the fire/water/earth. Give each ending the time it needs for you to process and then move on to the next.

When you are done with all of the endings, take time to write down or journal about any feelings that have come up for you. You may find a need to cry or yell or otherwise let out the emotion. Then put out the fire out, wash your hands with the water, or cover the hole with earth. 

Set a reminder to reflect on the experience in one week.

This ritual is adapted from my coach, Andy Crissinger, and from The Wild Edge of Sorrow by Francis Weller.

Challenges of Celebration

I leave this for last because it’s the most surprising on the surface. What challenges could possibly come when we have something to celebrate? 

But entrepreneurs spend their careers beating themselves up, comparing themselves to others, and finding any method possible to stay motivated to do the impossible. So when we finally achieve the thing we set out to achieve, it can often feel threatening, unfamiliar, and even depressing. 

Three core emotions

1. Joy – “an intense feeling of deep spiritual connection, pleasure, and appreciation” – Atlas of the Heart, pp 205
2. Gratitude – our ongoing ability to see, acknowledge, and celebrate the good things that have come our way in life, whether through luck, effort, or circumstance
3. Contentment – the sense that I have enough and the appreciation that comes with it; life is good and I feel a sense of wholeness

This quote from Robert Edmonds in Atlas of the Heart gets at why this category of emotion is hard for everyone, including entrepreneurs:

“Research on emotion shows that positive emotions wear off quickly. Our emotional systems like newness. They like novelty. They like change. We adapt to positive life circumstances so that before too long, the new car, the new spouse, the new house, they don’t feel so new and exciting anymore.”

In other words, after every good thing that happens to us we regress to the mean and take it for granted… unless we take time to pause, celebrate, and appreciate. That’s what this category is about. 

An example of how easy it is to struggle in the face of overwhelming positive outcomes is nearly every time I’ve seen an entrepreneur — whether client, friend, or otherwise — become a millionaire. Becoming a millionaire is a symbolic goal many entrepreneurs hold, even if not explicitly. 

Mark Manson shared his experience with me when I interviewed him about what it was like to sell millions of copies of his first book. By his mid-thirties he had achieved what had previously been lifelong goals. Now what? He became depressed and lost, that’s what. But then he recovered a sense of meaning and direction.

Coaching questions and exercises

Exercise one: Think about something you have achieved, gained, or own. This is especially powerful if you accomplishing that thing led to feelings of anxiety, worry, or fear. Now, ask yourself: What would it feel like to lose this thing? How would it change my life to have to live without it? Given how much I value it, in what ways can I consistently create a sense of appreciation for it? What habits can I build to celebrate it each day or week?

Exercise two: When in my life have I gained something beautiful that I then lost? How does that loss inform the way I feel about things I gain now? 

For example, if you were once married to someone you considered your soulmate, but then went on to be divorced. Or perhaps you built a successful business that later went bankrupt. Have you fully processed the sense of grief or loss? If not, how is that sense of grief or loss showing up to protect you from gaining what you truly want in order to prevent losing it again? 

From a centered place of wholeness, is the potential for loss worth the experience of joy you might gain if you really went after what you want?

—-

Most entrepreneurs know what they should do. They have the knowledge and understanding necessary to do the tasks and employ the tactics to get where they want to go. And yet, so many of us stay stuck.

What keeps us stuck is the emotional cost of what we know we need to do. The goal of this essay has been to open the door to future breakthroughs by highlighting the hidden emotions with a framework of challenges and then asking questions to help understand your inner emotional landscape. 

You have an immense potential — what you are capable of doing if everything lines up properly. No matter how much potential you have, what matters in building a business is performance — what you have actually done. 

I hope these questions and exercises help you translate your potential into performance from a place of wholeness, equanimity, and quiet confidence.

If you enjoyed this essay, it is based on a workshop that is much more powerful when done live and in community than it is in writing. If you host conferences, retreats, or mastermind events, please reach out if this workshop might be helpful for your group. 

Featured Photo by Chris Flexen on Unsplash