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A Conversation Between Coaches

with David Shechtman

Hey goal achievers, Kristin here. I recently interviewed a guest on the Elite Achievement podcast that I met a decade ago when an old employer hired him as a consultant. I coordinated many of his workshops and sessions, and as a result, invited myself to attend for my own growth and development. He is the person who taught me that you are either playing to win or playing not to lose.

I am thrilled to introduce you to David Shechtman. David is a Senior Partner at Evolution and a committed coach who works with CEOs, high potential leaders, and professionals on mastering deep change. He has an unparalleled ability to cut through the fog of complexity, confusion, and fear. David’s experience includes two decades of work in training and development, organizational consulting, and executive coaching. 

I start by welcoming David and asking what inspired him to begin coaching.

The Call to Coach

“I think I have a pretty unique background compared to a lot of coaches,” David begins. “I initially got into this line of work through the family business. When I was in middle school, my dad was coming out of a career in academia in Social Work Psychotherapy. He was inspired by that work with human potential and growth, but wasn’t excited about the environments in which he was working. So, he got involved in doing this in a professional setting, hung out his own shingle, and began working with a handful of local organizations like the police department, school district, etc. This was all in suburban Chicago. Over time, he built the business to include working with many different high-profile organizations, including Northwestern Mutual where the two of us met years ago. So that family business connection was the entrée for me into the world of coaching and many client systems that I continue to work with today. It was the first time that I thought that this kind of work would be possible. I feel grateful that my dad was a pioneer and did this sort of work very early on in the culture. I was able to see him as an example of somebody who could not only work in the growth and development space, but also had an entrepreneurial spirit. He was willing to just go start up a business and develop the field he wanted to work in. So that’s kind of the first part of the answer. The second is that when I was young, my parents separated and then ultimately divorced. I spent a lot of time as an only child from that marriage, feeling alone and unsure how to handle my situation. I had resources available to me, but not necessarily on a day-to-day basis. No siblings, and not a lot of other family that I was close to. And so, I had an experience where I did feel quite by myself. While I think I did a good job of finding what I needed and maintaining a sense of being grounded, I really feel a calling in the world to be a guide and a support to other people who are going through changes, transitions, and difficult experiences. I think many of us work in a world that we feel we are prepared for earlier in life, maybe through a challenge or a unique circumstance. So for me, the idea of taking on very difficult challenges, overcoming obstacles, and getting to a defined outcome was something I was doing pretty early in my life in a purely personal setting. I think a lot of those experiences helped shape me into the professional that I am today.”

David mentioned a calling to guide people going through difficult situations or changes, and I ask him to elaborate on how he recognized coaching as his true calling.

“You know, that’s an interesting question,” says David. “There are a couple of different answers to that. As I was describing some of my background experiences a moment ago, the first is a persistent challenge early on. And certainly, into my early adult years when I was getting started as a full-time professional. This also turned into a coaching mantra of mine to attract the right sorts of clients. For many of those experiences in my life, I felt like a great person trapped in a good person’s body. I felt like I’ve got all this talent, intelligence, social skills, big picture thinking, the ability to shift perspectives, intimacy building; these were all talents that in some cases came very naturally to me, and others that I developed. But I felt consistently that I couldn’t bring those talents out and manifest them in the ways that I wanted to in a personal and professional setting. So for me, as I did my own work and was able to more fully manifest those talents that not only I thought the world needed but I wanted to express, I started to identify myself first – some ability to connect those dots and create those sorts of trails that people could follow. It struck me that being in a helping role that way was a really good application of my own experiences that could show up in the world, and people would pay me. It would be a great mutual fit. So that’s kind of a narrative answer to it. What I would say goes along with that is when I was five years out of undergrad, and my dad and I talked about working together, I stepped into the role. After about six months of doing behind-the-scenes project work, I got a chance to work in person, and I got dropped into a meeting called a client builder. I know you know very well what those are. I didn’t know what a client builder was, and I wasn’t sure what I was doing. I didn’t get a whole lot of preparation as to what the meeting was even about. I sat there and made a few comments. And people liked what I had to say and then subsequently invited me back. So that felt like pretty good confirmation because I had very little idea what I was doing, and I was able to be effective in that environment, and people liked me. So, I felt like I got some pretty good market confirmation at that point. And I decided to listen to the audience and go forward with that.”

I connect with David’s example because I too got kind of thrown into coaching. I showed up in this role and was told I was going to be a coach. And I’m thinking, I’ve never coached before, what do you mean? What do I do? How does this work? And you figure it out. I know I was able to figure it out because it is what I am meant to do. I absolutely love helping people achieve the goals they want to achieve, maximize their potential, build their lives the way they want to build them. I am forever grateful for that opportunity to be put into that situation and get the chance to figure it out and grow that skillset. I ask David what he sees as some of the benefits of meeting with a coach. 

Being a Coach is About Making Ideas Work

“Great question,” David says. “By the way, I knew there was a reason I liked you from the time we met because apparently, we were on the same path in a number of ways. That’s a cool thing to even learn now about you all these years later! And your question is a great question, not just because of the obvious interest people have in coaching – I know it’s become a growth field. When I first began doing this work, I’d sit on an airplane and make small talk with the person next to me, and they would say, what do you do? I’d say, a coach. And they’d ask, like football, basketball? There was no conception that this could be a professional field and endeavor. Now when I say that people are like, oh that’s great, do you have your certification? It’s really accepted at this point and is not only a legitimate but also an important field. I believe that coaching is becoming the gateway to all meaningful growth, development, and change. And I say that because the world has transformed even since I began doing this work. I feel like an old person saying this, but when I started the idea of having access to best practices and good information still seemed rare, but it certainly seemed valuable. So, the idea when I’m first showing up, and I’m in that client meeting, telling you about the fact that I had some good ideas that maybe I’d picked up from somewhere else, whether it was another client or my own reading, seemed valuable. We’re in a world right now where everybody’s pretty much got access to all the information that’s available in the public sphere. There’s not really a question of what good thinking is out there or what good looks like. But as one of my mentors shared with me years ago, good ideas are overrated. It’s what you can do with them that counts. For me, coaching is fundamentally about doing something with good ideas. It is taking something from concept to application to result. And that is just simply not an easy process. But it’s not even possible in many cases, in my experience, without the direct support of a coach. I studied organization development; that’s what my master’s degree is in. Many colleagues and peers that I work with now have MBAs from top-flight universities, and everybody is walking around with an incredible amount of information and an endless supply of good ideas. But I think absent a meaningful coaching relationship, and it doesn’t have to be me – doesn’t have to be you. But absent some sort of meaningful coaching style relationship, the ability to actually make use of these ideas and derive meaningful personal benefit is nearly impossible. I think coaches make ideas work.”

I agree and believe that we’ve got the answers within us to do what it is that we need to do. And as a coach, it is my job to ask the questions to help pull those answers out of you and provide the accountability and the support to get you to take action, just like David shared. It’s taking a concept, moving to application, and then generating results. One of the reasons I believe people don’t take more action is fear, so I ask David to share his perception of fear and how he has seen it show up in the coaching process.

The Hero’s Journey: Working through Your Fear and Staying the Course

“I would agree with you that fear is the main, if not one of the main, blockers for just about everybody who is struggling with growth in their own situation,” begins David. “So, I’m trying to give an answer that is not just sort of a standard answer to that, because I think, again, a lot of people understand that fear tends to be about things that aren’t necessarily real. Or worst-case scenarios. There’s a grounding experience that coaches can offer, but you know, if I try to get to the question and what I think has been so useful for me in my work and the support I’ve offered with my clients, is this idea. This idea that growth comes when you can get lost with confidence. That’s a sort of developed or paraphrased quote from one of my favorite authors, Robert Quinn. He talks about the experience of working through deep change and how it’s a sometimes terrifying, always uncomfortable, experience. And that the ability to really work through those challenges and those fears allows a person to get lost with confidence moving forward. So, there’s this sense that I don’t know exactly what I’m doing. I am not sure where this is leading; there are no guarantees of an outcome. But I’m confident that I’ll figure it out along the way, and I’ve got trust in myself to be able to pull this off. Part of the reason I believe getting lost with confidence is a possibility is because of some of the work that I’ve done studying a particular author named Joseph Campbell, who wrote about a structure called the hero’s journey. Joseph was essentially an anthropologist. He was an academic, author, speaker, and ran a lot of workshops. He passed away in the late 1980s. But it’s very easy to find his lectures and materials online if you do a search for Joseph Campbell. Essentially, he identified a little bit of a complex concept. So, I’ll just try to be as brief about it as possible. But a format or well-worn path that everybody experiences – when they undergo meaningful change, deep change, transformational change, whatever adjective you want to use – looks like departing the familiar, leaving the known, and entering into a space with confusion, danger, and massive struggle. So essentially, where the individual proves him or herself by taking on a challenge or deal. If successful in overcoming that challenge, there’s learning and gains that are experienced. And then they return to the familiar with the application or use of that new gift, learning, or growth that was achieved. Many of your listeners have probably heard the hero’s journey; it is occasionally trendy. For example, the whole Star Wars franchise, the entire story, came from George Lucas reading Joseph Campbell’s material. So every once in a while, it kind of gets pulled back into the spotlight and discussed, and people, whether they’re in the entertainment world, the business world, or other worlds, find value in this. But for me, knowing that there is a pathway out there, allows me to get lost with confidence. Change can be such a lonely experience, right? I know in my own head, I get these messages that go off like – you’re not making it, this is not going well, you’re going too slow, this should be different. You should be farther ahead; you should be doing something different. I know that goes through my head. I know from the coaching work that I do, and I’m sure you experienced the same thing, people are thinking those thoughts all the time. We’re worried about those comparisons and challenges. So, it’s really easy to get into that space of believing that my situation is wrong, or it should be different. And for me, to really understand that there is a stepwise process to go through – it’s not always clean and perfect and linear, but it generally follows a particular direction – that allows me to rest in that certainty that a commitment to moving through a change cycle works. That is ultimately what leads to not only a short term, near term victory and wins, but a lifetime of abundance, reward, and success.”

As David shares the path for deep change on the hero’s journey, he explains departing from what’s familiar, entering a space of confusion and frustration, then moving on to learning. Then he comes back to the familiar with an element of massive growth that has happened. I’m curious as he talks about the stories, and I call these negative mental narratives – the shoulds and coulds, the overthinking, the worrying, the fear, the anxiety – if he thinks that head trash is showing up in the confusion stage of the hero’s journey. Is that part of the journey that we have to just work through?


“100%,” David confirms. “I know we have experience working with a lot of the same populations of people, folks who are in entrepreneurial settings and starting their own work or developing their own personal practice or business. And I believe that the main challenge of anybody that I work with is small thinking, fear, and the scarcity mindset. Most of us, I would say, think we have a pretty objective view of the world and that we see it as it is. But you have to check with people on a regular basis about truly how abundant the world is and how much is out there for everybody to experience. The main obstacle that you’re speaking to is this sort of negative messaging. The head trash really distorts that view of what the world truly has to offer. If the world were a place that had no opportunity, and only a couple of people were successful, and everybody else struggled, that does not reflect the life that you know or the majority of people live. Every coaching client I have lives in a world where there’s enough for everyone to go around. There’s enough success in the pie for everyone to achieve what they’re looking for. But the question becomes, how well are people going to move through the daunting, challenging tests that will bring out in them the greatness and abilities they have? Or how much are they going to stay in a safe, comfortable, but stuck space?”

I ask David to share some practices or strategies to move through that daunting space he spoke about. How does he suggest we move through this hero’s journey without giving up?

“That is a great question,” starts David. “And I was thinking about this in preparation for our conversation. I actually think I would answer this a little bit differently now than when you and I last worked together three or four years ago. I now believe that self-care is maybe one of the keys to making it through the ups and downs of growth and transformation as people go through it. I have shifted some of my opinions about muscling through overwhelming situations with force and intensity. I think that maintaining confidence, being optimistic, and holding situations lightly – as lightly as possible – is a very, very important path forward. Sometimes I think of it this way. I have one daughter, and I remember going through all the sleeping challenges and all those different phases when she was younger. I’m sure you have those memories seared into your consciousness as well. I remember that, at certain points, I would get so incredibly frustrated that I wanted something to happen that wasn’t. I wanted her to go to sleep now, or go to sleep a half an hour ago, or stop waking up, or stop asking for milk or water or whatever it was – whatever diversion was up. I remember at that time that I had two ways of handling that. One was just to accept the situation as it was and try to do my best in that situation. Being in full acceptance of it. Or, I could get irritable and angry and stomp my foot and growl at my daughter and talk to her through gritted teeth, and basically express my frustration in passive-aggressive ways. I did my fair share of both. So, you know, I’m not the perfect parent. But when I was able to accept the situation, be kind to myself, and go with the flow, I just found everything worked out better. And I had a better experience. My daughter had a better experience. And her maturation and development took care of all the challenges eventually. I think that to me, that’s a really good example of a lot of the challenges that people face in life when they’re dealing with something that they don’t like and don’t want. They are looking to have a different experience and are trying to force it into existence somehow, and then becoming not only frustrated at the lack of a different result, but frustrated that the effort was not paying off. I think what that does is take people almost out of a natural state, out of a healthy approach, and into one that feels exhausting, coercive, and even depressing. And for me, when I have helped people accept their situation, focus on what they can do and control, even find humor in the circumstance, there’s an energetic shift that feels incredibly potent to me. What I have found is that when people have that approach to their situation, they rise to the occasion and engage in appropriate change at the moment. But it doesn’t come from beating oneself up. It comes from rising, lifting oneself up. Especially these days, with so much disruption in the environment and chaos, news and pandemic, and everything else. A self-care forward approach is helping people not just manage the challenges of the environment, but move through the growth and development process in such a more productive way.”

In my own business, I know if I’m feeling frustrated and looking at things through a negative lens and feeling those negative mental narratives in my head, it is usually a sign I have deviated too far from my self-care practices. I’ve gone to a place of “I’m so busy,” and “I’m so overwhelmed.” I might bypass the things that I know are good for me, the simple yet powerful practices such as meditation, gratitude, reading. I will push those aside to go to work harder and to work more. And it actually does the opposite for me. I work with a lot of clients who are women in financial services. And many of them are saying, Kristin, I am constantly being told to work harder and do more. That the answer to every one of my business problems is to keep more meetings, make more phone calls, do more, do more. I heard David say that he went through a shift in his thinking, and is moving away from that thought process of everything being solved with more effort. I ask if he will tell us more about that shift and how he is working with leaders to help them embrace that thinking as well.

Not Everything Needs to Be Solved with More Effort

“Great question and phenomenal topic area,” says David. “So, I think it is fair to say that some of the aspects of what we’re talking about do involve massive amounts of effort. So, I don’t want to be too glib about that. Lots of people, especially in the early stages of launching a business or endeavor, they’re going to have to put in a lot of time. That is certainly a part of it. But for me, that’s not so much always a coaching situation or coaching opportunity. Because people don’t need to hire me to say work more, they can figure that out on their own. But there comes the point in most people’s situation, whether they’re in an expansion part of their business or a more advanced or more sophisticated level, where it becomes more about their presence than it does just simply about their effort. When it comes to doing high-level financial services work, or any high-level kind of work, people are going to respond not just to the volume of things that you’ve done or the number of hours that you’re putting in. They’re going to respond to the way you show up and the sense of energy that you bring. People in financial services are going to be remembered for the way they made their clients feel. Do their clients feel satisfied, excited, exuberant? And so, to deliver a presence or an experience that has a profound effect on people that doesn’t come just through hours at the office, or throwing pure time, sweat, and elbow grease at a situation. I think there’s actually a point where it flips and the harder you work, the less effective you become. Because it’s draining your energy, it is creating almost like a doom loop where the more you work, the less present you are, which means the more effort you have to make to compensate for the lack of presence. People can find themselves in what feels like quicksand, where the harder they work, the more they sink into the pit. The people I’m coaching, whether they’re in sales or leadership positions in organizations, are fundamentally wrestling with this. Because the majority of people in the knowledge economy now could literally work 24 hours a day. I mean, there’s just no limit to the things they could be doing at any given point in time. And most of those things would be meaningful and valuable for somebody to do. So, the challenge now that I see my clients experiencing is knowing how to prioritize. It’s knowing key things they need to be doing and what they can defer to somebody else by delegating, collaborating, or putting it off, or not dealing with it at the moment. Then also knowing how to show up in a way that has a profound impact and shifts people’s view of what’s possible, or creates a sense of intimacy and connection that drives the desire for a lifetime relationship. Those don’t come through effort. Those come through embodiment and connection. And embodiment and connection are, again, back to the self-care concept, cultivated from within. It’s a sense of knowing who I am, what my work in the world is, and how I can invite people into that experience. And that has to live on a platform of effort and a platform of movement, you know? There’s no doubt about it. People need folks to work with. But at some point, the greater investment of time and energy will be in the delivery of self in the engagement and the work that comes through that exchange. When that really becomes a powerful part of somebody’s presence in how they work with people, whether they’re their clients and prospects out in the marketplace or peers and reports within an organization. When that becomes a powerful part of their work, it actually requires less face time and less effort. Just showing up in a room has an impact on people.”

David talked about the importance of learning how to prioritize and how to delegate, so you can show up with the right amount of presence and make that impact. I ask him to share a couple of ideas that can help us figure out what to prioritize and make sure we’re delegating the right work.

Show Up with Presence through Prioritization and Delegation

“Let me answer the question this way,” says David. “I’ll try to keep it relatively short, but I’m a big inside-out type of thinker when it comes to these sorts of topics. There’s a belief behind the behavior. So, I really think that beliefs drive behaviors, and behaviors drive results. There’s a framework that I often use called be, do, have, which speaks to that. So, when I think about your question, asking for techniques to be able to delegate and prioritize, I think it fundamentally comes down to a belief about who I am as an individual in the world. And this is a pretty well-used phenomenon or condition right now. But I think imposter syndrome plagues a lot of people, and I would be willing to bet a lot of the people you were talking about, especially folks in the financial services industry, maybe don’t have as much of a history with that or building their business. So, there is this idea that I’m the worker. I need to be hustling every single moment. There is almost a badge of honor around exhaustion and burnout. I think that experiences caused by this imposter syndrome are going on, internally within people’s heads, thinking like, well, who am I to meet with that person? Who am I to ask somebody to support me with this work? Who am I to delegate a task to somebody else? I’ll do it. It’s quicker for me to do it. I should be doing this. I haven’t earned the right to be able to hand this off yet. And, I think that’s the majority of the battle. When people can see themselves as a successful professional, as somebody who’s focusing on connection with prospects and clients, not just putting in the effort behind the scenes, that’s the biggest shift. I think when that imposter syndrome gets addressed, brought into the open, named, and worked through, the behavior changes are pretty simple. You just find a resource or ask somebody to help or engage with a peer, whatever is practical at the moment. So, to me, the biggest challenge is in the belief about who I am. What experiences do I deserve to have? When can I actually be supported? When can I ask for support and come to expect that out of important relationships in my life?”

The framework David provides and the behavior results can be applied to so many different elements of growing a business, growing a career, growing yourself. It’s brilliant to understand who I am and ask how I am viewing myself so that we can continue to grow and experience the deep change David spoke about. He also shared a pathway for understanding how change happens when we depart the familiar, enter into a space of confusion, learn, and return to that familiar space. And we need to be mindful of those negative mental narratives that show up on that pathway for change in growth. I also loved hearing about the importance of self-care and how self-care is so much more than a post that we see on social media or a buzzword. And how self-care can really lead us to establish an abundance mentality, move through change, and understand how we can show up as our best selves. 

I thank David for his insights and ask him where people can go to learn more about his work. He suggests his website.

With that goal achievers, keep celebrating your weekly wins, learning from your lessons and identifying your priorities. So, you can consistently pursue progress in the direction of your goals.