When Leaders Become the Bottleneck | Jenn Lofgren, Managing Partner | Shed Talk Ep. #115

Kevin talks with Managing Partner, Incito Executive and Leadership Development Jenn Lofgren about imposter syndrome, ego, perfectionism, and the moment a leader becomes the bottleneck. She shares coaching stories about founders, executive teams, boundaries, trust, and why 'letting go' by even five percent can change how leaders show up at work and at home.

Guest: Jenn Lofgren - Managing Partner, Incognito Executive and Leadership Development

Jenn Lofgren is a professional coach focused on leadership development for individual leaders and teams. Her path included 11 years in network infrastructure, HR work, professional coaching training beginning 17 years ago, and board service that helped her understand the pressures leaders face.

In this episode:
- Recognizing internal friction as a leader
- The angry founder who needed a different way to lead
- Imposter syndrome and not feeling good enough
- Why imposter syndrome affects so many people
- Can you stop imposter syndrome?
- Ego, fear, and needing to be liked, right, or winning
- Asking the better question: what’s my part?

Chapters:
0:00 Welcome and the question that frames the episode
0:32 Recognizing internal friction as a leader
1:58 The angry founder who needed a different way to lead
3:09 Imposter syndrome and not feeling good enough
5:05 Why imposter syndrome affects so many people
7:06 Can you stop imposter syndrome?
9:08 Ego, fear, and needing to be liked, right, or winning
12:42 Asking the better question: what’s my part?
15:26 The crossing-the-line exercise
17:52 Letting go of perfection in presentations
21:21 Why leaders and executive teams seek coaching
24:34 The power of asking how things are really going
27:29 Jenn Lofgren’s path into leadership coaching
33:02 A mentor’s lesson on boundaries and people pleasing
36:10 When leadership work changes life at home
38:22 Building trust through executive team storytelling
40:58 Using coaching skills with family
42:14 Vacation, energy, and work-life equilibrium
45:29 Kevin asks what he needs to let go of
48:20 The inner security guard and small changes

What is Shed Talk with Kevin Halliday?

Shed Talk with Kevin Halliday is built on a simple belief: the right conversation can change the direction of your life.

From a shed in Calgary, Kevin sits down with entrepreneurs, experts, community builders, and people with hard-earned stories. Together, they move beyond titles and highlight reels to talk honestly about what worked, what failed, what changed them, and what others can learn from it.

Grounded in the three pillars of health, wealth, and mindset, Shed Talk explores the whole person behind success—the habits, relationships, pressures, choices, setbacks, and moments of reinvention that shape a meaningful life. It is not inspiration for a moment; it is practical wisdom you can carry into your business, your family, your health, and whatever you choose to build next.

Kevin believes life does not end at 50—it starts. Every episode is an invitation to stay curious, challenge what you think you know, and turn insight into action.

You don’t know what you don’t know—until you know.

Kevin] Well, welcome to Shed Talk, Jen. Thank you very much for coming on.
[Guest] Thank you. I'm so happy to be here.
[Kevin] Well, you know what? You and I have been in forum forever and a day. Was it 10 years?
[Guest] Oh, like two years.
[Kevin] Two years? I knew I would get it close. So I have to ask you a question,
[Kevin] okay? Because everything that we've done, how does a successful leader recognize
[Kevin] when the person who got them there is no longer the person that can take them forward?
[Kevin] You
[Guest] know, I think it has to do with recognizing some of the friction you're experiencing in your everyday life. And when I say friction, I mean the internal friction
[Guest] that happens, feeling like your stress is mounting.
[Guest] You used to feel confident about
[Guest] what you're doing and the decisions you're making, and you're feeling less confident in those decisions, and there feels like more churn in the decision -making or doing things the way that you did before.
[Guest] It feels like it's not giving you the results that you want, and you can't quite understand
[Guest] why. And you've missed that the context has changed. And then the first starting point is noticing what's that friction that I'm feeling inside and getting curious about that.
[Kevin] So, as young entrepreneurs, and we look at growing, we're excited about being entrepreneurs, we're 20 some odd years old, the young entrepreneurs, then you get to the old guys
[Kevin] like myself, 58 years old, been around the track a long time, and looking at this and then all of a sudden saying, how do I get out of my own way? And then, because sometimes we don't
[Kevin] even understand it. And like you had just said, well, you're not thinking about what you're doing or our past is, it was easier and now it's not.
[Kevin] your past.
[Kevin] So how does the older guys like myself all of a sudden create purpose and meaning as a leader and no more valuable?
[Guest] As you're talking, you triggered for me a leader that I worked with that there were three founders to accompany.
[Guest] And one of them was sat down by three other founders about five years into the business.
[Guest] And they sat him down and said, go home for 10 days.
[Guest] And when you come back, you need to work with a coach because you're angry all the time.
[Guest] And you're eroding our culture and people are leaving.
[Guest] You don't have to come back. We'll buy out if making changes isn't for you. And he went home and he thought about it for three days. And he called me on the phone and he said, I'm going to work with you. And I said, I'm going to be there on the third day. And I asked him, why'd you call? And he said, I
[Guest] think they did me a favor. I'm actually tired of being angry all the time, but I actually just don't know what else to do. Because by being forceful, by being aggressive has actually got us here and I'm tired of doing
[Guest] that. But it just, don't know how to keep creating the outcomes that I know I'm so great at creating
[Guest] and doing them in this new environment. And I need some help.
[Kevin] did you get them help?
[Guest] The help started with talking about the problems that we face. And that was really, really important to things that he was feeling uncomfortable with, that he was struggling with. One of them was
[Guest] this founder started with two other founders that had business degrees. He had a lot of imposter syndrome about not having an MBA, not having a degree at all, had been a helicopter
[Guest] pilot. And that was his first career and brought him into some entrepreneurial thinking and some startup companies that led him into a much larger organization and had never led an organization of
[Guest] So you
[Guest] this size before and compared himself against the other leaders and was trying to be like them and to lead through force. And it wasn't working for him and it was impacting him at home and at work
[Guest] and in his own self -confidence and well -being. And we started talking about what are some of the things that he was worried about and not talking about.
[Guest] With anyone and to give him an opportunity to have a sounding board to talk them through and then consider how he wanted to show up and change his way of thinking about himself as not
[Guest] being good enough to, okay, I might not know how to do that yet, but I can learn.
[Guest] And to
[Guest] work with his partners in the business and be honest about some of the things that he wanted to learn more about or that he wanted to do differently.
[Guest] And make some requests of them instead of keeping it all to himself and just trying to figure it all out all out on his own.
[Kevin] had mentioned, and I want to get into this, is that imposter syndrome, great
[Kevin] leaders, managers, we're all in to grow, okay, we haven't gone coaching,
[Kevin] How big
[Kevin] how big is imposter syndrome?
[Guest] There's research out there that started with looking at imposter syndrome they thought impacted women because it was the
[Guest] a PhD researcher in a university that was doing research on women in leadership and found 70 % of
[Guest] women are impacted by imposter syndrome and then expanded that research to, oh, what's it like in the general population of all people, not just leaders and not just women and found that actually
[Guest] 70 % of us experience imposter syndrome at some point in our life. And then there's Kristin Neff. she also has done a lot of research about self -compassion and we've gone away from this
[Guest] idea of self -esteem because self -esteem and imposter syndrome are closely linked because self -esteem relies
[Guest] on me believing that I'm better than average but then if we all need to believe that we're better than average well then the average bar moves up and
[Guest] that leads to imposter syndrome if I need to believe that I'm better than average. Self -compassion is the key or antidote to
[Guest] imposter syndrome of not comparing. Self -esteem relies on comparing to the average. Imposter syndrome relies on me comparing with those around me and I'm not good enough and what if I'm found
[Guest] out too. It's okay for me to be struggling and I'll figure out my way and trust that I have the skills and the resources to find my way through hard things, hard decisions as a leader stepping into ambiguity and complexity.
[Guest] as the market changes the business changes some things happen with our staff and our product
[Guest] and I trust that I'll find my way because I have the capacity to learn and to adapt as I go and not rely on being perfect from the beginning or better than the average that where I'm at is good
[Guest] enough and I can bring my best and I can learn better learn more and when I learn more I can do better you
[Kevin] How do stop imposter syndrome?
[Guest] can't
[Guest] can't because we're human and it happens but
[Kevin] but can't I just say, okay, I'm going to put myself
[Kevin] full force and I'm going to bulldoze my way through it.
[Guest] we're human and part of being human I think is about wanting to be better and in some ways I think it
[Guest] drives us to learn and drives us to pursue being better and there's a fine line between not believing we're worthy of belonging of our roles of
[Guest] relationships of the businesses that we're creating and being good enough as a person
[Guest] compared to imposter syndrome that it's just that little bit of imposter syndrome that drives us to it could be better and a little bit of hustle and to strive for continuous learning
[Guest] can drive
[Guest] and I believe that when we stop pursuing learning and trying to be better and having a little bit of could I be better it can drive us to actually be our best selves and we're always becoming the next
[Guest] best version of ourselves all the time but not because we're beating ourselves up but because there's a little bit of hunger and drive but what if I'm actually not good enough because I could be
[Guest] better tomorrow one percent better tomorrow and the next day I could be one percent better again
[Kevin] What about ego? So let's get into ego, so all of a sudden I have an imposter syndrome, okay, as an example, oh, okay, I can't believe I can do this.
[Guest] say more
[Kevin] But if I think in my head, I'm gonna wake up in the morning. I'm gonna do one of these things just to get me out and fixed. I'll fuck this shit over, do this because I'm going to bulldoze my way through it. Can an imposter syndrome actually turn and be ego? Too much ego and say, okay, I'm all this in a bag of chips.
[Kevin] Okay. Could it be the
[Guest] that's
[Kevin] a great
[Guest] reverse of it? That
[Guest] question I think my reaction to that is ego is fear driven and there's three
[Guest] fears that are underlying ego and they're who am I if I'm not liked who am I if I'm not right or who am I if I'm not winning
[Kevin] imposter syndrome now. So this is where it comes in to ask a better question and
[Guest] good question I haven't thought about that
[Kevin] okay I have so much ego I'm gonna
[Kevin] say, okay, if I have so much ego and I'm going to bulldoze my way through something, but at the same time, I'm scared because that next person, here's the imposter syndrome come in, that next
[Kevin] person besides me to say, oh, he's nothing but ego. No, I'm going to make this happen because
[Kevin] it's called a non -negotiable. I'm going to non -negotiable this all the way. Oh, do you have ego you bet I got ego I gotta make
[Kevin] ego? You bet I got ego. I got to make this happen. But do I have an imposter syndrome at the same time? Because we just explained three different ways. Am I being liked? Do I know what I'm going to be doing? For sure. Because we feel that.
[Kevin] So is there a balance between ego and imposter syndrome? And can you balance that?
[Guest] I
[Guest] as we're talking I think the imposter syndrome is more of that connection to who am I if I'm not enough if I'm not right liked or winning where if you step
[Guest] into more self -acceptance the ego settles down and that fear settles down and self -acceptance then drives you more towards a sense of purpose and there can be a lot of energy in that forceful
[Guest] drive behind it but a different kind of forceful drive because it's in service of creating a better
[Guest] So
[Guest] future and a new outcome not a scarcity mindset of what I'm trying to avoid and protect
[Kevin] think about it now. Let's take that and move it into leadership because now you're the head of your organization. You got to have, yes, your imposter syndrome is there. Okay. Am I good
[Kevin] enough to do this? If you're a female leader or a male leader.
[Kevin] Okay. And then now all of a sudden I can't fail and I can't show vulnerability to my team.
[Kevin] as
[Kevin] Okay. As a leader, because I have to go to the next level. Yes, I have to have ego because I've got to make sure that they're very confident where I'm going and what my vision stands for.
[Kevin] Now, throwing in the culture. Now we're all about culture because leaders sometimes fall apart in culture. Is that correct? And leadership.
[Kevin] Culture and leadership oh
[Guest] and leadership. Can that be different too? But can they be fallen apart as in, so ego?
[Guest] I think they're intimately linked culture and leadership
[Kevin] Okay. So, and then all of a sudden you have ego in there. Then we have imposter. syndrome in there. We'll have culture and it's kind of a different thing. Well, it's the same, but different, but it's going to, you're looking at each other as a leader trying to grow. And
[Kevin] then you have to balance your ego and your imposter syndrome at the same time and still lead this group of people. And then that came to the first question that I'd asked is about
[Kevin] way you want to lead the way you want to lead the way you want to lead the way
[Kevin] how do you recognize your gifts and abilities when you first started as a leader in your organization and your company, knowing that here you are today,
[Kevin] you are actually the bottleneck of your growth strategy today.
[Kevin] So how do you recognize that too?
[Guest] you often say ask a better question and I think that's part of that recognizing is pausing and asking yourself a better question when things are getting hard
[Guest] what's my part
[Guest] and often we're looking at
[Guest] what's external to us for what someone else's part and forget to look at once
[Guest] my part
[Guest] and
[Guest] asking myself seasoning I could be better
[Guest] fit a little bit different
[Guest] that I think it's really
[Guest] governments are creating a reflective practice in some way that gets you think you know what I could
[Guest] where I could be better than you know we do 360 assessment with leaders and those are really helpful in raising self -awareness but in debriefing
[Guest] thousands of them with leaders over the years and some leaders are transformational for some of them
[Guest] Do they
[Guest] it was an interesting hour and put it on the shelf and move on the real difference is those that ask the question themselves well what's my part and what I'm creating and what I want to
[Guest] create next
[Kevin] bring people along for the ride? So in what's my part, what are we going to create? And what's next as a leader? Because all the people that you've trained
[Kevin] around North America to bring into your systems as a coach, what has been the, one of the greatest challenges in that realm?
[Kevin] Where do they see themselves? How do they grow?
[Guest] you say that again
[Kevin] So with all the training that you do North America -wide, you base it, you have all these
[Kevin] yeah
[Kevin] people, they're talking about going to the next level. What do they bring as a leader? And because you described them, how can they move to the next level?
[Guest] and
[Kevin] And, or actually I'll make it even better because this will be, make it more fun. What is one of the experiences, okay, that you've had? Because you're teaching all these great leaders all over the world that really threw you for a loop. Like you can't believe that this is what you're doing. You can't believe that this is what you're
[Kevin] doing. This is what they thought, but it was actually something else.
[Kevin] A really interesting story that would tell about, because a lot of entrepreneurs and leaders out here, what we talk about is about how do we grow? How do people like us? Okay.
[Kevin] How do I move my people? Okay. Or my organization. And somebody is going to go in this direction, but all of a sudden they do something totally different that you go, it works for them, but I would never have coached you to do that.
[Kevin] Like what would be the most wildest thing you've ever seen in leaders? in leaders that
[Kevin] That kind of shocked you
[Kevin] talk about you.
[Guest] oh oh man I can't think of one right now I think one of the things that um always amazes me though is there's an exercise we do
[Guest] where we just do a crossing of the line and it's a simple exercise that unlocks
[Guest] unbelievable thinking for people and we get them thinking about these ideas of you know yourself best which one is your favorite being liked right or winning we get them to stand in that place on
[Guest] this model and just below the line we get them to think about where do you want to be a year from now
[Guest] as a business as an individual for your team paint the picture of that now
[Guest] think about
[Guest] what is it across the line that you would need to do a little bit differently with your strength what would you need to grow it a little bit more into
[Guest] in order to make that future happen that you're not doing today and then they step across the line and they talk all about all the things that they want to do and then I get them to turn around
[Guest] and look back it's like so tell me what are you willing to let go of to get you there they're like well I think I'm going to need to do I'm like no no no I didn't ask you what you need to do and well I think I should do like I don't know I don't know I don't know I don't know I don't know I don't
[Guest] know this isn't what you need to do or what you should do I asked you what are you willing to let go of and there's something really powerful about saying I'm willing to let go of a little
[Guest] What
[Guest] bit of pleasing people or I'm willing to let go of people being a little bit disappointed in me saying no to them or I'm willing to let go of things being a certain level of polish and being
[Guest] a little bit embarrassed in front of a client for the sake of learning of one of my team members man that's going to be really hard
[Guest] and I'm not sure how to do that yet but I'm willing to learn and that's where we get some real transformation for people and that's where all the crazy things that I've seen show up with leaders comes from is that owning and willingness to name what they're
[Guest] willing to let go of not that they need to not that they should that they're actually willing to commit to letting go of even just one percent
[Kevin] would be the craziest thing to let go of? Give me an example.
[Kevin] one
[Guest] leader it drove him crazy that board presentations would have errors in them and investor presentations going out to the
[Guest] investor community in New York and Toronto and he keep going back to his team and giving them feedback redoing their powerpoints spending all -nighters for a large organization and it
[Guest] just didn't make any sense but this perfection gremlin was just so strong and it still wasn't working because the leaders were still showing up even with him going through these investor decks and board decks
[Guest] and he realized that I need
[Guest] to allocate some time back to my team into myself he went back to his team and he said you know what I'm going to die a little bit inside every time internally I see your errors in our presentation decks in our meetings and I'm no longer going to say anything
[Guest] about it because it doesn't matter but what I want is all the time and energy that you put into all
[Guest] work. I want you to redirect towards board and investor deck presentations because those are the ones that are material and matter around our credibility and our fundraising for the
[Guest] organization. And that little change then rippled into some other changes. And when we first started working together, he was a 38 -year -old CEO of a fast -growing organization, had three young
[Guest] children at home, and he was working 16 -hour days.
[Guest] Within 12 months, he started taking similar approaches to other little things in his work, and he was going home at 4 .30. He was feeling a little bit of guilt going home at 4 .30 because he's like, surely there's something else I should
[Guest] be doing. In my days, I'm full filled with planning and strategy and conversations with board members and our executive team, and am I missing something?
[Guest] think because it feels like this should be my job but I feel like I should still be working the 16 hour days but it was little by little making those decisions of what to let go of that he realized
[Guest] he wasn't actually attending to his work as a CEO he was in the weeds doing everybody else's work and nobody was leading the company and that's what he started doing but it started with that
[Guest] shift of recognizing letting go of winning and being perfect in everything that his team did and got them to direct their attention on what mattered most how many leaders the third
[Kevin] leaders out there do you find are micromanagers?
[Kevin] Third. And what would be one of the things that they, so they hire your organization, okay, to come in there.
[Kevin] Is it the leader that's bringing you on or is it the board? Which, why would they hire you? How would they, why would they hire you? Like, how do you recognize that you're in trouble? Yes. Besides my financials
[Kevin] are really bad, but is it culture bad? Is it the leadership's bad? How do they recognize where, because if I'm a leader, I think everything's fine. You don't know what you don't know. So
[Kevin] I'm thinking, okay, here I am. When do you actually ask a better question that we need to bring coaching in? We need to bring a leadership team in here.
[Kevin] To understand what we need. What's that process of for organizations and companies?
[Guest] Well, a lot of people think that individual coaching starts with there's something wrong with the leader and it's an intervention. Most of the work that we do is probably 90 % or more is with leaders that are looking to become even better.
[Guest] There's not something off the rails. But I know I could be even better. There's not something wrong, and I just don't know how I could be better
[Guest] because lots of things are going really great, but I want to take things to a next level with my team, my role, I want to get a promotion, or I want to drive our business in a new, more powerful direction.
[Guest] And things are going really great, but that's
[Guest] the problem. I don't know what I need to learn next, and I want some help with that.
[Guest] That's the majority of the leaders that come to us. When we work with executive teams, often there's something that's going on with the executive team. That's when we get brought in to help them.
[Guest] And then there's often an economic crisis that's going on. There's a shift in the stakeholders and their expectations or with customers in the market.
[Guest] There's a new CEO or a new leader of the team. There's some significant change in the team. Yeah.
[Guest] There's some alignment issues, some going along to get along. There could be false harmony in the team, or there could be some active conflict in the team.
[Guest] Or it's a team that's struggling to create some great business results and advanced strategy.
[Guest] And on paper, they're all rock stars, but they're not operating as a team. I think they are. They're a group. Everybody's divide and conquer and do their own thing, and the strategy is not succeeding.
[Guest] And then that's when they'll ask us to come in and figure out, what could they do to unlock what's happening for the team and turning it into a high -performance team?
[Guest] But individual coaching, most of it is, I want to become even better. And then the 10 % that are sent to coaching, that there's something getting in the way,
[Guest] often there's conflict with the coworker, or there's some underperformance in their business area,
[Guest] or there's a culture problem in their team. Yeah.
[Guest] Or there's some turnover or something else going on in their team.
[Guest] And we can't coach them or can't help them unless they answer this question.
[Guest] How are things going for you?
[Guest] Is everything okay?
[Guest] If they're like, everything's fine, can't help.
[Guest] And if they're like, no, I think there's some things I want to be different.
[Guest] Yeah, I'd like some help.
[Guest] Then we can get somewhere. Because I use the example of, I can't coach someone to run a marathon if they don't want to run.
[Guest] If there's something you want to work on, and you have something you would like to be better, but you don't really know exactly what the vision is, I can help you paint the vision.
[Guest] If you have a vision, and you don't know how to get there, we can help you get there.
[Guest] But if you say, everything's fine, and I'm good, and I don't need some help, then let me know when you're not good.
[Guest] But right now, I can't help.
[Kevin] You just hit a chord there.
[Guest] You
[Kevin] We deal with men's, mental health. And we talk about, ask
[Kevin] me talk about,
[Kevin] a better question. We talk about how do we get men to
[Kevin] and women?
[Kevin] communicate? And you just said it right there. And it's that common thread that from leaders of coaching to men in therapy, and to ask that question is that first question that we always
[Kevin] ask is, so how are you feeling?
[Kevin] How can I help you? How can I make you successful?
[Kevin] And it has a pattern in business. It has a pattern in our personal lives. It has a pattern in everything that we touch and do. And then here it is in the leadership role of you going in there and asking
[Kevin] the executive team, I can't help you. And where can I take you to the next level?
[Guest] How powerful is that?
[Guest] Yeah, back to the leader. I said that, called and said, and I said, what made you call? He says, I'm tired of being angry all the time.
[Guest] But I don't know what else to do.
[Guest] Would you like some help with that?
[Guest] Yeah.
[Guest] I'm willing to do anything.
[Guest] I don't know what it would look like.
[Guest] If you can help, I'll take your help. And then,
[Kevin] you're booked in, you help them out. And how was the impact when you met him in person? I'm assuming this was a phone call conversation.
[Kevin] Very.
[Guest] This was a phone call conversation. And this was a local client that I did work with in person.
[Guest] And totally a different person than anybody described him as. We did a 360 assessment.
[Guest] And reading the feedback was not the person I had got to know.
[Guest] Oh, wow.
[Guest] How do we help everyone around you see the person that I've just got to know
[Guest] and have all those strengths shine through in a way that they can get the very best of? And so, that became some of our work together.
[Kevin] So it's interesting. I'm going to go back to this because it's really powerful.
[Kevin] And I always go back to ask a better question. You opened up and you asked him a better question of how I can help. Now, let's talk about that. How did you know that? How did you get started
[Guest] question.
[Kevin] into this? Because this is pretty powerful stuff. When you start thinking about this,
[Kevin] you're helping leaders, but you're helping men and women, leaders role,
[Kevin] The leader's role
[Kevin] that you can't help one without the other. You have to be intertwined in personal, and everything we're doing. How did you get started in understanding the personal,
[Kevin] to do it.
[Kevin] personally, the
[Kevin] like this whole effect of how to do this? You didn't just, we're born with it. Like, all of a sudden, what's your experience to doing this? Because that's pretty powerful.
[Guest] All these
[Guest] Yeah. I think I'll go back to one of my first jobs that got me really curious about this.
[Guest] And one of the core beliefs I have in coaching today is I worked for one of Calgary's most esteemed interior designers as his personal assistant for one of my first jobs.
[Guest] And some of the wealthiest people in Calgary and in the country would come by our office.
[Guest] people in Calgary and all waiting for Doug to be with,
[Guest] And while waiting for Doug, they would chitchat and talk with me about how their day was going.
[Guest] how they're doing, going through a lot of other families, hear
[Guest] But I hear a lot about their family.
[Guest] I'd be in their home babysitting a plumber. And I'd hear about how things are going with their kids or with their parents and all kinds of things about their lives.
[Guest] And I realized, oh, they're people that are just like me and just like other people in my life. Their context is just different. And, oh, they're just people, too.
[Guest] And why I offer you that is because today I'm often talking with our team about leaders are people first, leaders second.
[Guest] And helping people be their very best started from that very curious moment really early in my career.
[Guest] And I ended up going on a technical career for 11 years in network infrastructure
[Guest] and had a gift for developing culture and my team partnering with the business on strategy
[Guest] and developing out really great teams.
[Guest] And I got to a point where I wasn't satisfied in that career. And I'm like, what if I could take all those things and make it the core of what I did?
[Guest] And it took me back to school full time and getting my HR designation with an interest in leadership culture and teams. But I had no idea about professional coaching. In fact, at the time, professional coaching was a very early profession.
[Guest] And after a few years working in human resources on the other side of that degree,
[Guest] I sought to do more leadership development work and learned it was done by external consultants. And I thought, I should do a professional coaching course because it's a skill that would be helpful for me in organizational development. And leadership work.
[Guest] My goal was not to do professional coaching. And that was 17 years ago.
[Guest] And after getting my coaching designation, I set out as a solo entrepreneur, solo consultant,
[Guest] working with managers and directors and doing some leadership coaching and some HR consulting work. Within a year, I realized the impact that I'm meant to have is by helping leaders and being a thought partner.
[Guest] Alongside them, helping their development that I stopped any of the HR consulting work because that's work for somebody else to be deep in their expertise. And I want to be an expert in one thing and one thing only.
[Guest] And that is the journey of leadership development, whether it's for an individual leader or a team.
[Guest] And over 17 years of rigorous,
[Guest] ongoing professional coach training, I also believe you can't be just one and done and do your professional coach designation.
[Guest] But continuing to train in new methodologies as a coach every year,
[Guest] because my job is to help accelerate the leadership development of our clients, I need to be continuing to accelerate my own development as a professional coach and understanding new methodologies, but also just the journey of leadership
[Guest] that also put myself through serving on boards.
[Guest] So I wanted to understand what it was like to be in the seat of many of our clients in ways that I had never experienced.
[Guest] At that point in my career.
[Guest] And served on probably eight or nine boards to get a range of experience in partnering with other executives and making ambiguous decisions
[Guest] and hiring
[Guest] CEOs and parting ways with CEOs and developing new strategies
[Guest] be a leader, and maybe to be
[Guest] and working with one organization through a crisis in COVID where they almost shut the doors and financial restructuring. I had to experience myself, what the pressures are that our clients go through
[Guest] to go with the expertise and coaching that I've developed over the years.
[Kevin] So what was, throughout this whole year, all the years that you've been involved,
[Guest] coaching,
[Kevin] coaching, leadership, what was the most impactful time, that one moment in life, that all of a sudden you'll always remember? Everybody has something that they remember
[Kevin] everybody had something in that one moment going
[Kevin] from zero to hero, but that one moment that actually transformed your life, at that moment, as a coach, as a leader, that you knew, this is for you. And you talked about going on the board because you wanted to feel. What does it feel like to be on a board? What
[Kevin] does it feel like to do that? Not anybody can just do that.
[Kevin] There's no way. You have to be a special person. You have to be built. You have to be wired special to do that. And then where governance comes into play, where all that is, what would you say one of your greatest, and I
[Kevin] We're all at it.
[Kevin] wouldn't say strengths or superpower, but what was that one moment in time that just
[Kevin] next level? What was that one moment in time that just catapulted you to the next level? This is me,
[Kevin] as a hush goes over the crowd.
[Guest] I actually want to tell you something else first that's really transformed who I am. And it was actually an experience from someone that took a coaching approach with me that wasn't a professional coach. It was a mentor for me.
[Guest] And I was struggling early on in my consulting practice and with a colleague.
[Guest] And I went to talk to him and I told him the story of what was going on. And he says, uh -huh.
[Guest] And then what did you do?
[Guest] Well, and then I did this.
[Guest] And he's like, hmm, I see what's going on.
[Guest] Your colleague asked for a rock and you gave him a rock. And he said he didn't like that rock and so you gave him a blue rock.
[Guest] And then he said, I don't like that. And so you gave him a blue stripey rock. And he's like, oh, I want a red rock. And you gave him that too. At what point do you stop owning the other half of the relationship?
[Guest] Like, oh, because
[Guest] that's my edge is I want to be right, liked, or win.
[Guest] I wanted to be liked.
[Guest] And I'm like, oh, I got to work on letting go of that.
[Guest] So how do I do that and still build great relationships?
[Guest] And that was a pivotal moment for me in experiencing that myself where somebody challenged me on a pattern of thinking where I was
[Guest] how
[Guest] overusing a strength and getting in my own way. And the shadow side of that was coming out for me.
[Kevin] did you get out of it? Or recognize it?
[Guest] You know, I let that situation go with that colleague.
[Guest] And it came up a couple of months later on something different.
[Guest] And I noticed it in the moment.
[Guest] And I took a breath.
[Guest] And I swallowed. And I said, I don't think this is going to work. This is what I can do. This is what I can't do. And if that doesn't work for you, then I don't think this is going to be a fit for us to work together on projects anymore.
[Guest] And it actually ended up being the end of that relationship.
[Guest] And it was a relief for me.
[Guest] But I set a boundary. And there were consequences to the boundary.
[Guest] And it was actually one of the best decisions I could have made in hindsight in seeing some of that person's pattern afterwards that I could not have known at the time.
[Guest] But the sense of relief when I walked away that I don't have to do that in this relationship anymore was a real power for me that I could then carry into other relationships and setting boundaries.
[Guest] And that it's okay for it to turn out. In a way that I didn't expect it first.
[Guest] It's like, oh, I really want it to be harmonious all the time.
[Guest] It's one of
[Guest] And it wasn't. It actually ended the relationship.
[Guest] And it's one of the best things that I could have done.
[Guest] those
[Kevin] things, they say, you don't know you're in jail until you break out.
[Kevin] And then ask yourself a better question. How do you go to the next level? And not knowing, because that's the scary part. If it's a customer or where you're at is, how do you end it? And then all of a sudden, the fear mongering in your head is like, oh, I don't know what I'm going to do.
[Kevin] How am I going to do this? How does that work? So how do you know if it's right?
[Guest] Well, and I'll come back to your question about then some of those times. Yeah. There's a lot of times where this is what I meant to do.
[Guest] And they're often little moments.
[Guest] There's one chief commercial officer I worked with for a year.
[Guest] And at the end of the year, we're just doing a look back on the year of what's changed for him and what he was proud of and what he's going to look at learning next and what's next for him on the other side of coaching.
[Guest] And he said, you know, a
[Guest] lot has changed with my team, with my peers. With the strategy, with the business.
[Guest] But you will never know how much you changed my marriage.
[Guest] All the things that I've been working on at work have dramatically improved my life at home.
[Guest] And I'm like, wow.
[Guest] Leaders are people first, leaders second.
[Guest] And for him, that was the most impactful thing he took away from our coaching was the impact it was having on his life away from work. The reason why he's doing what he's doing in his career.
[Guest] To have the life that he wanted away from work had been so enriched through our coaching. Even though it wasn't the focus or goal of our coaching.
[Kevin] It's interesting. It's kind of like people talk about being life coaches, and all of a sudden, don't really. So here you are doing leadership, talking this, but all of a sudden, someone's hearing something else. It's kind of like, you get 100 people, and you're going to tell a story, and they're going to have 100 different stories.
[Kevin] But this guy, he was looking for that one story for him that impacted him the most as a leader.
[Kevin] And it was his wife. Well, maybe it's the communication. Or the guy that's 55, 56,
[Kevin] suicide, or wherever he's at, and asking that one question is, are you OK?
[Kevin] Well, why ask me if I'm OK at work? Why don't you ask me if I'm OK at home?
[Kevin] And it's kind of the same conversation. It's interesting how, again, I go back to how that all intertwines and how impactful. That was for him.
[Guest] And, you know, we work with teams around strategy and alignment.
[Guest] And some of the most tricky conversations and direction around business.
[Guest] But the most rewarding all the time come back to the things that they don't want to make time for.
[Guest] There was an executive team recently where we're at an off site. And we asked them a question to do some personal sharing with each other.
[Guest] And I turned to my right and the chief legal officer beside me gives me a look like, you've got to be kidding me. And I looked at him and I said, I'm not kidding. This is what we're doing.
[Guest] And one by one, they shared. And at the end, it was so powerful. It seems like this was so deceptively simple.
[Guest] And it was magical.
[Guest] We would have never done this on our own without you.
[Guest] And how it transformed the relationships in this team in getting to know each other and really understand where each other is coming from. Way beyond any personality assessment tool that we could use. And often we use those.
[Guest] And they can be interesting tools.
[Guest] But the simple act of telling stories that reveal who you are to the rest of the executive team, nobody wants to do that. Nobody makes time for it.
[Guest] And it's actually the core of being a high performing team is developing deep trust and understanding of each other so that you can confront each other. You can challenge each other because you trust that it comes from a good place and good intent.
[Guest] And that I know the person across from me.
[Guest] And I believe they have good intent in coming to challenge me and talk with me. Because I've heard a bit about their story. And they know mine. And they see who I am. And I see who they are.
[Kevin] it's interesting. Here it is again. We're talking about your
[Kevin] employees, your C -suite, everybody there. having that conversation. have that conversation. But how many people actually take that home and have that exact same conversation with their loved ones?
[Kevin] Fathers talking to their sons the same way as they would talk to their, as in the board meeting, to have that conversation about strategy.
[Kevin] Okay.
[Kevin] But before you do that, you had to have a conversation. Well, let's tell a story about what you're doing. How many father -sons out there in the executive community that actually have that same conversation with their son, realizing they can take that experience and have that conversation with their
[Kevin] what they learned here and take it home with them did
[Guest] Yeah. And there's a few.
[Guest] Almost every time we do a coaching skills for leaders program, we have one or two leaders in the session come
[Guest] and have a conversation and say, you know what?
[Guest] This has been helpful for my team, but I think I'm going to go and try this out with my teenager at home.
[Kevin] you ever see that coming
[Guest] No. No. First time it happened, it was like, oh, I hadn't thought about that.
[Guest] and
[Guest] Yes.
[Guest] Please do that.
[Guest] Let me know how it goes.
[Kevin] it's interesting because the more you start thinking about the more we communicate so we shed talk and we talk about men's mental health and health wealth and mindset it all flows together
[Kevin] you can't you can't fake it you can't you're you're a leader you're a team leader you're this you have to take the exact same home same thing home with you from business and this is where it
[Kevin] gets into another part is there a work -life balance and you were mentioning earlier about
[Kevin] Can you really be the gentleman that all of a sudden hey i don't have 14 hours i'm back i'm able to do that
[Kevin] was he able to go home and have a conversation with his wife or his kids now that he has that time that he's now not micromanaging the actual the board or the the slides that he's sending out
[Guest] That's exactly what he was doing. He was going home and spending time with his family. He was going on vacation with his family.
[Guest] And there's so many executives that I've worked with where, when we first start working together, they haven't taken all their vacation in years.
[Guest] One leader, I remember, he had nine weeks of crude vacation.
[Guest] On top of the six weeks he had. he needed to take that year he had 15 weeks of vacation and within two years he took it all
[Guest] because he started making some changes and one of the most important changes we made is it just got scheduled in he didn't know where he was going or what he was doing it just got scheduled in the year
[Guest] so that everything else could fit around it and work with the his EA to protect that time and
[Guest] that and resetting with his family about here's when we're going to take vacation time and then we'll decide what we're going to do with it so that I can actually go and do things with you and so we
[Guest] went from nine weeks bank vacation to using uh yeah probably four or five of them in that year and the other couple more the next year and had used it a lot within two years and then regularly
[Guest] took his six weeks vacation every year after that so
[Kevin] is there such a thing as work -life balance why
[Guest] because life goes up and down and work goes up and down there's times that are going to be uh really crazy busy at work or really crazy busy at home
[Guest] sometimes they collide but I'm looking for what's the equilibrium over time and how are you feeling about your energy and how's it working for you some people um go
[Guest] at a higher rate and they they crave being a little busier and putting it more energy into if they're not doing it work they're going to be putting it into hobbies or something else with their family but it's what's the the mix that's working for you over three
[Guest] months over the course of the year but there's also periods that are going to be really busy or crises happen and can't look at work -life balance every
[Guest] day and even this idea of balance has a sense of judgment in the word it's how is your life working for you how are you really feeling and something's not feeling like it's working well
[Guest] let's talk about that and look at what do you need to be different and how do we get you there
[Kevin] so here I am I'm
[Guest] that's
[Kevin] a great question always ask yourself a better question so i've got a one for you okay so here i am i'm 50 years old i'm over 50 i stopped stopped drinking i rebuilt my health i transformed my body
[Kevin] and i changed how i think about my life totally and you being an eo with me and see me how i've changed now i'm also trying to move from being the indispensable founder okay because i can't
[Kevin] be replaced okay uh who solves everything's and to
[Kevin] everything to
[Kevin] become a leader and developing others what from your observation in me okay because you you know me very well and everything that i do what is the deeper leadership transformation that i'm going
[Kevin] through and what do i still need to uh let go to reach my next level
[Guest] in
[Kevin] say like what strengths of mine help create my success but now limit me
[Kevin] this was like the first question so i wanted to bring it back to myself because you know that i'm a leader and i'm going to know who i am and everything that i do yeah
[Guest] a little bit about who you are I don't know everything you do
[Guest] true
[Guest] and I had an even better glimpse of that today um one of the things
[Guest] because you'd
[Guest] I know about you is your superpower is just how you are today you're really great at performing you're really great at taking the stage and sometimes it can show up as an armor and letting people get past that armor
[Guest] sometimes um but I think I would ask you the question of what's
[Guest] the thing that you're holding on to that if you were to let it go five percent would
[Guest] get you more of what you want as
[Kevin] mentioned that before and you just mentioned armor and it's like uh we talk about vulnerability and that if if i'm not performing you use the same thing as
[Kevin] performing am i not uh moving forward if i'm not okay if i can't create this and i'm doing this i've got these all these things happening if i stop just to take a break
[Kevin] this becomes the ego or is it the guy on my shoulder telling me that the imposter syndrome
[Kevin] impossible
[Kevin] saying that so which one where do they come into a fine balance because that's where i asked that before am i scared to open up so i have to be busy all the time or is it a time that you just
[Kevin] have to say okay time to relax and take a break because i found that i have to be always go go go
[Kevin] and i don't know if it's a good thing or a bad thing but i'm not scared to open up and i'm not scared to open up and i don't know if it's a bad thing but i'm i seem to have to be dialed in all the time plugged in and then it's not micromanaging or maybe i am
[Guest] now
[Kevin] because i said maybe i am that means i probably am so
[Guest] yeah
[Guest] say when we say maybe it's our soft tell on ourselves
[Guest] and
[Guest] are less conscious coming through and maybe I oh pay attention to that
[Guest] yeah but
[Guest] yeah but
[Kevin] i'm this and this and and it's not because with the men's mental health talking and where i was before sleep apnea gout and these are storytellings here i am and then here i am now things are
[Kevin] going great moving forward but there's still an armor there's there's there's still a barrier but what is that and it's trying to find and ask myself a better question what what am i not
[Kevin] moving forward with what am i not asking the question for myself and only i can answer it not everybody else can say well this is what your problem is or not so what is it to me what is that armor that i'm holding
[Guest] and there's something interesting our brains do you're talking about the little guy on your shoulder I call it your inner security guard and their job is to keep us safe but some sometimes so safe they keep us safe and they keep us safe and they keep us
[Guest] from what we want most coming next and they tell us a lie and the lie that they tell us is if I'm here
[Guest] and you say you want to let go and you maybe you want to come over here one step I'm going to tell you the lie that you're going to go all the way or really you're only intending to take a make a
[Guest] five percent change but that inner security guard or the little guy on your shoulder is going to say oh if you take one step it's going to go all the way to the other side of the street and you're
[Guest] spectrum not true and it's giving ourselves permission to change two percent five percent and often leaders I'm working with them like do not change a hundred percent because we won't know
[Guest] who you are but we will lose all your gifts and strengths so there is some wisdom in that inner
[Guest] so would
[Guest] security guard at the little guy on your shoulder telling you that is your superpower it's telling you that you have to use it at 120 percent all the time and challenging that is no there's some situations where I can let it go five percent and I can let it go five percent and I can let it go
[Guest] five percent and what's five percent look like that small shift and if I do that experiment what might I learn might work great might not work great but then it's learning in the process
[Guest] and then you can decide oh can I do I want to take another step or is that enough a step or
[Guest] maybe it was too big of a step and I can step back a little bit their inner security guards keep us from taking learning steps because they're fear -driven and they're worried that we'll go all the way to the other side of the spectrum and give up our strengths
[Kevin] you call that controlling the narrative
[Guest] hmm say more
[Kevin] so controlling the conversation we have in our heads that if i'm going to do this okay visualization we sit there and we visualize what we're going to do how we're going to do it for the
[Kevin] day and then yeah here's my storytelling because i visualize pictures then all of a sudden now the pictures are gone now i'm vocalizing really telling them
[Kevin] vocalizing my storytelling that it's this this oh now i'm talking in my head versus visualizing the picture in my head so two different things here's the picture i can see myself doing this
[Kevin] picking this up and doing it then when i start to talk it's the talking the voice and doing that but it's not pictures then that becomes okay now i'm going to control the narrative i have to keep
[Kevin] voice and doing it
[Kevin] him quiet by showing a picture of what i can do and it's all about the visualization and not the conversation
[Guest] sometimes I talk about it's like turning down the volume can't keep it quiet um but it's like turning down the volume on that inner security guard I can't have done it show me Scott a really
[Guest] important job it's a job to keep me safe but who's driving me or him if he's too loud it's the only narrative that I can hear so I need to turn his volume down sometimes it's even some self -talk of naming I'm going to control the narrative I'm going to control the narrative I'm going to control the narrative
[Guest] okay I hear you that could be a risk really realistically how big is that risk and is it a risk I'm willing to take having that kind of conversation with yourself and even naming it
[Guest] and saying this time I'm willing to risk it and I'm okay with it
[Guest] and that just naming it
[Guest] settles down that voice inside and turns the volume down by acknowledging because if you just ignore it it's like an alarm bell it gets louder and louder and louder and so you can make a change once or twice and it's like I'm going to control the narrative I'm going to control the narrative
[Guest] twice but to make a repeated ongoing change it's not sustainable because that inner security guard gets louder and louder over time but if you acknowledge it and you look at well what could
[Guest] really go wrong and what's the worst case scenario and am I okay with that and if I am like okay you know it might not work out and I'm choosing to and it's from a place of awareness and intention
[Guest] and choice then default and there's other times where it's no
[Guest] today's not the day I'm not willing to do that today but I'm now making the decision to do it and I'm not willing to do it and I'm not making an intentional choice rather than operating on on default and that's where then our ego drives is
[Guest] when we're operating on default as soon as you pause and you make an intentional choice from awareness then your wise sage starts driving instead of your inner security guard so
[Kevin] interesting so is there one thing that you tell our listeners
[Kevin] out there about what does it take
[Guest] to
[Kevin] be a leader
[Guest] it takes to be a leader is to relentlessly work on being a better human
[Guest] first so that you can become a better member of a team and when I say team I mean really a team and building strong relationships with those around you in service of driving whatever the
[Guest] purpose is a better business a better volunteer organization a better community whatever kind of leadership role that you're in but it starts with really developing yourself as a better person
[Guest] first and when you do that you'll become better
[Kevin] and it's interesting we're going back to the same thing that it keeps going back and falling back to being being a better leader being better human just be a better person and that it all flows together and
[Kevin] all folks together you know we get to talk about mental health
[Kevin] become one it's it's everything that we talk about in shed talk men's mental health and everything that we're going it's all about being a better person but leadership is one of the things
[Kevin] that everybody strives for but actually you just want to be a better human and then we come there
[Kevin] so how does anybody find you how do they get a hold of you spell
[Guest] I'm on LinkedIn and my website incito .ca
[Kevin] inside oh well that is awesome you know what jen thank you very much for being on shed talk with kevin halliday like share hashtag
[Guest] I -N -C -I -T -O means incite excite and inspire incito .ca
[Kevin] hammer that button we'll see you more thank you very much for being on here and sharing this great experience thank you