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Amy Kemp On An Inside Look at the Benefits and Impact Of Working With an Executive Coach

An Interview With Chad Silverstein

People are not problems that need solving. They are spiritual and emotional beings who need connection.

The competitive edge in business often comes down to a combination of strategy, foresight, and professional development. For executives looking to level up their skills, an executive coach can be their biggest asset. In this feature, we talk to business leaders who heavily invest in personal and professional development opportunities, coaching, and leadership programs. They’ll share why they invest so much and the impact it has on their life. Today, I had the privilege of speaking with Amy Kemp.

Amy Kemp is the owner and CEO of Amy Kemp, Inc. In her work within this growing company, Amy helps leaders and business professionals understand how deeply thought habits impact every part of their work and lives.

As a certified Habit Finder coach, Amy has led over 400 female business leaders through a four-month small group engagement called Encounter. This experience is designed to help clients replace subconscious thought habits that are no longer serving them with more healthy ones. She has also worked through the Habit Finder curriculum with hundreds of leaders in one-on-one settings and with leadership teams at small and large companies.

Thanks for being part of this series. Let’s jump in and focus on your early years. First off, can you give us a snapshot of your life before you started your career?

Of course! My first professional experience was teaching high school English. While teaching, I started a small business in direct sales that over twenty years, grew into an organization of over 1000 independent sales consultants across the United States that I led. About six years ago, I went through an extensive training process to become a certified Habit Finder coach and started a new company, Amy Kemp, Inc. While I still own the other business, this is now my full-time work.

What was it about personal and professional development that attracted you to start investing in yourself? Also, can you share when you started and what your first investment was?

Interestingly, my mom was my leader in the direct sales company in which we worked. We quickly realized that your mom can’t really “coach” you. With her encouragement, I hired my first coach about fifteen years ago. It was a transformational experience and throughout the past fifteen years, there have been few times when I haven’t worked with a coach in some capacity. I always say I’ve invested more time and money in personal development and coaching than anyone I know.

Can you think back and share one of the biggest blind spots you had that someone helped you see and something specific about what you learned and how it showed up in your life?

I often felt deeply responsible for the success or failure of the people I was leading, which led me to do things for them which they could have been doing themselves. In order to move from just being a producer to really being a leader and a developer of people, I had to learn to ask questions and listen rather than solving problems and fixing people.

How long have you had an executive coach and how would you describe your relationship?

I’ve been working with my current coach for about six years. Pam has been instrumental in guiding me through both the emotional and technical parts of a major professional transition as I started and have grown my new company. I think I could have figured out the strategic business parts on my own, but I never could have done it so quickly and I definitely could not have worked through the emotional challenges of leaving one space in which I was so well-known and respected and entering a new world where I knew so little and was starting something new.

If I was sitting down with your coach, and asked “what’s the one thing your client needs to work on more than anything else in the world” what would I hear them say about you?

She always tells me I have “the most sensitive integrity meter” of anyone she has ever met! While this is a good thing, it slows me down because I overthink decisions or want to unroll or move forward perfectly. Sometimes, you just have to move before things are perfect.

If you were questioned about your “ROI” (return on investment), is there anything you can point to that justifies how much you spend on being coached? If not, how do you justify it?

The most simple, measurable ROI is that I earn four times what I earned when I hired my first coach and I work fewer hours than I ever have before. My goal is to work like a teacher (8–3 Monday through Friday and off weekends, lighter schedule in summer and with school breaks off too) and get paid like a CEO. I’m proud to say that my work with coaches has created not only a great income but a great life.

Let’s dive into specifics. What are the top 5 things you’ve either gained or learned about yourself, where you specifically made changes, and have seen positive results. Be specific and feel free to give us either the background or story about each.

I deserve to be paid handsomely for doing the things that feel easy to me but astonish everyone else (my natural genius).

I’d love to illustrate this phenomenon with a story about a client I’ll call Nicole. Nicole took over running the finances of a fledgling family business about sixteen years ago. The company opened right before the recession of 2008 hit. With her brilliant, strategic business mind at the helm as the CFO, the company not only navigated the challenges of getting off the ground in the middle of an economic downturn, but it has become the largest independently owned company in its industry in the Midwestern United States.

We were at a business event together recently, and I over- heard her describing her role in the company to someone she had just met. She so vastly undersold herself in her description in this conversation, I would have thought her role was to balance the checkbook for a small mom and pop shop. To be clear: Nicole manages the finances of a growing multimillion- dollar company that is ten times larger than it was when she started! I was flabbergasted.

Here’s the problem. This work feels easy to Nicole because it is in an area of natural genius for her. Combine this with the cultural conditioning that teaches women to stay small and not “brag” about our accomplishments, and we consistently and vastly undersell ourselves in spaces where we would benefit from a more accurate description of our accomplishments. I later told her that she should hear how I describe her when I tell others about her work and professional successes. Some might think we were talking about two very different people! I’m afraid women everywhere are doing this same thing and missing important connections and opportunities as a result.

This is why I spend a significant amount of time with my clients helping them identify and leverage their areas of natural genius more fully. In other words, I want you to do a lot of the thing that feels easy to you but astonishes everyone else.

And I want you to get paid really well for doing it! Everyone has something they do that causes the people around them to exclaim, “How do you do that?!” And when people say that to you, inside, silently, you pause and think, “Uh . . . it’s not that hard. You just do it.” This is your natural genius.

You can increase your income, impact and influence without working more hours.

I am by most accounts a pretty straitlaced person. I don’t drink. I don’t smoke. Outside of an occasional Netflix binge, I don’t have many vices . . . but if I have one addiction, it would be to my work. Yes, work can be an addiction. My default when faced with most challenges is to simply put my head down and work more hours. I knew from years of experience in sales that under the pressure of a goal with a clear purpose and deadline, very few people would or could outwork me.

However, this default of working more comes at a cost. It requires a great deal of time and emotional energy. About six years ago, I realized that our family needed me to provide more income than I was with kids heading to college and added costs of teenage drivers and travel sports. I also knew that already I had increased the number of hours and the intensity of my work to maximum capacity. At home, my investment in my kids’ lives at this particular season felt more crucial and finite than it had at any other time. I wasn’t willing to miss games and family events or, more importantly, the conversations that happened in between all those daily experiences. Whatever changes I made to provide more could not require any more energy or time from me. There wasn’t any more to give.

As this realization settled in, a steady stream of questions filled my mind.

  • If I’m already exhausted by my work and life outside of work, where will I find the energy to create something new?
  • If my current leadership responsibilities already feel draining, why would I want to lead more people?
  • Is it even possible to increase my income without sacrificing the time and energy that I want to devote to my family and other priorities outside of work?
  • How much longer can I keep working at this pace?
  • What do I need to do to get to the next level of income, influence, and impact? And if it’s not something I need to do, how do I become more? What are the practical steps for that?
  • Most people already see me as exceedingly successful. What will they think of me if I achieve this new level of success? Will I be too much for them? Will this shift neg- atively impact important relationships in my life?

And perhaps most painful of all:

• What is wrong with me that I haven’t been able to figure this out? I’ve worked so hard and for so long and still haven’t produced enough.

Over the next few years, I grappled with these questions and all of the emotions that accompanied them. With the guidance and patient help of several important coaches and mentors, I discovered that any changes I made in my work or behavior would be fleeting if I didn’t get down to the roots of the thought habits driving my choices.

More than anything, I learned that I could not outwork my thought habits. Instead of just putting my head down and pushing harder like I always had before, I had to first uproot the unhealthy thought habits that were so deeply buried I hadn’t even realized they were there. After working with ambitious women for more than two decades, I know that these habits of thinking are not unique to my experience. Women everywhere of all ages, ethnicities, and levels of experience battle them.

My constant availability was the biggest impediment to the growth of my business.

When I was a brand-new leader with only a small number of people on my team, I often felt consumed by a deep responsibility to make sure every person I led was happy and that they all were successful. I felt like I needed to answer every text, every email, every phone call immediately because they needed me if they all were going to succeed. Evenings weren’t really time away from work but an extension of it. Even vacations were full of “urgent” calls and messages that needed my attention. Because my business was so new and small, I felt like this was necessary, especially if I was going to survive financially for those lean first years of entrepreneurship. However, this self-imposed expectation created a very fragile dynamic in my organization that looked like a bicycle tire with long thin spokes. I was at the center of the wheel, and all the spokes led to me.

In the middle of that stressful and exhausting season of almost nonstop availability, a wise mentor and coach overheard me on the phone handling a sticky customer situation that really wasn’t my responsibility. I didn’t trust the person on my team whose job it was to handle these situations as well as I thought I could. After I hung up from the call, this mentor asked me a life-changing question: “Can you do for one hundred people what you just did for that one?”

At first, I felt defensive. What was wrong with helping someone navigate a difficult conversation? After all, I had plenty of time in my day for these conversations because my business was still small. I needed every possible customer if we were going to survive. Pretty quickly, though, my mind started thinking through a few of the other things I had done that week for the people I led. I started filtering each situation through the question I’d just been asked.

Could I completely interrupt the workflow of my day to call corporate headquarters to find out whether our products have gluten in them for one hundred salespeople under my leadership like I just did for that one? Could I stop what I was doing to find the link to the product shade conversion chart for one hundred people like I just did for that one? Could I disrupt my work to find a phone number for one hundred team members when it was easily accessible on the company website?

My stomach sank with the realization that my constant availability was very likely the reason that my organization wasn’t growing. Yes, my constant availability was helping those I led immediately, but it was not creating independent problem-solvers who could figure out issues on their own.

Scheduled guilt-free play is the most important investment I can make in my business.

Scheduling free time and play into our lives makes sense given that we live in rhythms. Our physical world has seasons, and seasons are rhythms. Sometimes it’s freezing cold. Sometimes it’s steaming hot. Sometimes it’s mild and in the middle. Our lives have rhythms. The tyrannical tempo of toddlerhood slows to the moderate dance of adulthood and then on to the wandering waltz of old age. Our weeks have rhythms. There is a sputtering start, a crescendo in the middle, and a sweet, anticipated end. Our days have rhythms. There are mornings, afternoons, and then evenings — and then we sleep.

And of course, art that speaks to us deeply has rhythms. For example, music. Songs slow and speed up, they are soft and then they are loud, taking us on a journey through their rises and falls. We connect with rhythms because we are created to live in them. Expecting that every element of every day of your life will be structured is unrealistic, unhealthy, and ignores our need for rhythms. We can focus intently on our work, but then we need rest. Simply put, there is no way to sustain structure and focus over the long haul if you do not have a break from it.

While I used to feel guilty for taking time to “play,” I now recognize that my nights playing pickleball, card games with friends, long walks with my husband or even fun weekend get-aways are the most important investment I can make in my work and the people I lead. My brain needs a break, and it performs better when my life is full of play.

People are not problems that need solving. They are spiritual and emotional beings who need connection.

As I have developed as a leader, I have had to learn that there is only so much I can do alone to create the results I want. In order to take my businesses to the next level, I had to learn how to develop and coach people. I also had to accept that I am not responsible for the experiences or outcomes of those with whom I work. I can journey alongside them, and the action they take as a result of my coaching can have a significant impact on their progress, but I cannot carry the weight of their burdens or feel like their failures and struggles are my fault. This separation between me and the results of other people is an important boundary if I want to increase my influence, impact, and income. Many women especially sabotage their growth, even turn down potentially life-changing leadership opportunities, because they don’t have adequate boundaries here. The emotional weight of leading people is just too much to bear.

Maybe you can relate, and this is even why you’ve avoided pursuing the leadership roles within your company or chosen profession. Why would you want to apply for a leadership role where you would have to carry the feeling of more responsibility for others when just managing what you already have feels overwhelming? Even more, how can you really know and invest in people but not carry the pain of their challenges, failures, and choices? Can you sit back and watch someone struggle to succeed in a role that feels incredibly easy to you? How can you truly hold someone accountable to performing at a high level when you know what is happening in their life outside of work hours? Is it even possible to care but not carry the burdens of the people you have been entrusted to lead?

What advice would you give other entrepreneurs who don’t think it’s worth investing in a coach or spending money to join a leadership program?

I don’t want to follow any leader who doesn’t consistently make space in his or her schedule for personal development or coaching. Leaders face a myriad of challenges that require safe spaces where we can sort out emotions, work through our past unhealed pain and think strategically without the person listening having any stake in the game. Your spouse can’t do this. Your co-workers definitely can’t do this. You need a neutral party who is holding space just for you. It’s the most important investment you can make in your business.

Do you have any examples of how being coached had an impact on others who work around you? How has it spilled over to your team or your family?

We are who we are at work and at home so coaching always has an impact on not only me but on those people I care about most, my family. I see this same thing happen with my clients. Relationships are healed, families are healthier, and so are communities when leaders are healthy and cared for in the context of a coaching engagement.

There are so many executive coaches out there. How did you go about selecting the right one for you?

It sounds simple but mostly, I trust my gut. I can tell in one conversation whether this person really sees me. It’s a feeling. I would recommend people have an exploratory conversation with any coach before hiring them and then to trust their instincts. You’ll know when it’s a fit. And there are certain coaches that travel with you for a season and then it’s time for someone new. That’s totally okay too! I want my clients to do this, and I have done the same.

Lastly, where can our audience go to follow your journey and perhaps get inspired to make their own investment in coaching?

I’d invite anyone interested in my work to go to www.amykemp.com and take the Habit Finder assessment for free. You’ll get a 44-page snapshot of your current subconscious habits of thinking right after you finish taking it and the results may surprise you. You can also follow me on Instagram and Facebook at @amykempinc.

Thank you so much for joining us! We wish you only success.

About the Interviewer: Chad Silverstein, a seasoned entrepreneur with over two decades of experience as the Founder and CEO of multiple companies. He launched Choice Recovery, Inc., a healthcare collection agency, while going to The Ohio State University, His team earned national recognition, twice being ranked as the #1 business to work for in Central Ohio. In 2018, Chad launched [re]start, a career development platform connecting thousands of individuals in collections with meaningful employment opportunities, He sold Choice Recovery on his 25th anniversary and in 2023, sold the majority interest in [re]start so he can focus his transition to Built to Lead as an Executive Leadership Coach. Learn more at www.chadsilverstein.com


Amy Kemp On An Inside Look at the Benefits and Impact Of Working With an Executive Coach was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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