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From Isolation to Collaboration with Heather Bennett

  • Writer: Megan Robinson
    Megan Robinson
  • Jun 19
  • 17 min read

Updated: Jun 20

The decisions are yours and they are lonely decisions to make because no one can make them for you. But how those decisions get executed needs to have the support behind it.

The Loneliness of Leadership

Leadership can often be a lonely journey. As Heather points out, being at the top of an organization comes with the expectation to have all the answers and guide the ship. This pressure can lead to feelings of isolation. By seeking support early, leaders can mitigate these feelings and create a network of trusted advisors who can provide guidance and perspective.


Tease Key Insights

  • Having a diverse group of advisors allows leaders to gain insights from various perspectives, which can be invaluable when making tough decisions.

  • Consistent support helps leaders refine their decision-making processes.

  • Leaders who actively seek support are often more open to learning and growth. The best leaders are lifelong learners.

  • Recognizing the need for support can prevent burnout and ensure that leaders are equipped to handle challenges effectively.


Why this Matters?

Leaders may sometimes reject the idea of needing support, believing they can handle everything on their own. However, Heather points out that even those who claim they don't need support often seek it in different forms, such as through podcasts, books, or webinars. The key is to recognize when support is necessary and to be open to it.


Listen Now

Heather's insights underscored the importance of not going it alone as a leader. Whether through formal coaching, peer groups, or personal networks, having a robust support system is essential for navigating the complexities of leadership. For those interested in learning more, I highly recommend checking out the Growth + Exit podcast for further stories and advice from business leaders.



Heather Bennett

Managing Director and Partner


Heather H. Bennett is managing director and partner with Newport LLC (a national business advisory firm), board director, author of the book, Fun and Fulfilling Careers One Question at a Time and the host of the Growth + Exit Podcast. Her subject matter expertise includes social media, integrated marketing, personal branding, and entrepreneurship. With over 25 years’ experience as a career and business coach for executives and entrepreneurs, Heather specializes in C-suite advisory, revenue growth innovation, leadership development and marketing strategy.


Full Episode


Megan:

Hello and welcome to Culture Conversations, the podcast where we explore the people's side of work. I'm your host, Megan Robinson. For years, I've found myself deep in discussions about workplace engagement and industry action. Now I get to share this wisdom with all leaders, new and experienced. on their journeys. If you're looking to learn more about how to support your organization, we spend so much of our lives at work. Let's make it a place where our tierings can grow and succeed. Now get out there and contribute positively to your organization's culture with your Hello and welcome to Culture Conversations. I am Megan Robinson, your host, and I'm so excited for my conversation today with Heather Bennett. We are going to have such a good dialogue, talking about not doing it alone. Talking about what does good support look like? How do you get it? Because we all know that it is wildly lonely at the top. If you are a leader, if you identify as a leader, you feel that you're in some sort of leadership position, most likely you don't feel like you have a lot of support. You feel like you have to be the one doing everything. You feel like you have to be the one leading. And it is lonely, it is isolating, and it is not necessarily the best way to grow, to develop, to help others if you don't have that strong support system. I'm going to go ahead and introduce my guest. Heather Bennett is a managing director and partner with Newport LLC. It's a national advisory firm. She's a board of director. She's an author of the book, Fun and Fulfilling Careers, One Question at a Time. I have read it. It is fabulous. And she is also the host of the Growth Plus Exit podcast. Her subject matter expertise includes social media, integrated marketing, personal branding, and entrepreneurship. With over 25 years of experience as a career and business coach for executives and entrepreneurs, Heather specializes in C-suite advisory, revenue growth innovation, leadership development, of course, and marketing strategy. Welcome, Heather.



Heather:

Thank you so much for having me, Megan. I always love our conversations.



Megan:

Per usual, I always have someone jump on the call a little bit earlier if we still say call or Zoom or recording a little early and we just started diving into it. It's always one of those moments you're like, wait, stop. Let's go ahead and start recording. We said all the good things already. Just kidding, tons and tons of knowledge from Heather. I mean, even just looking at her expertise and we were talking about what it is that she's passionate about and what kind of information and wisdom she wanted to impart on everyone. This idea of support came to the top because as a coach, as a consultant, as an expert, you know exactly how to support people. You're almost this expert in support.



Heather:

You're very sweet. It's important. I think that's part of the job. As an advisor, as a consultant, one of the biggest parts is gaining the trust and giving as much support and really serving the people you're working with and helping them be the best they can be. That's a little corny, but that's really where it comes from.



Megan:

And it comes from such a genuine place when you put yourself in that, I'll say, servant leadership role in that aspect. So you are that expert in support. You've been doing this for a heck of a long time. You have a amazing roster of successful and happy clients. Kind of kicking us off on this topic of not doing things alone, identifying that support. Help me understand, what does good support really look like?



Heather:

To your point, being a CEO, being at the top of an organization is lonely because you're expected to guide the ship. You're expected to have the answers, know where things are going, understand the strategy. Good support means feeling comfortable enough with your leadership team. And even like maybe the next tier down, being comfortable enough with them to be honest and be able to say, I don't have all the answers. And it's OK to say that. Now, you still need to have a certain amount of confidence. And a good leadership quality is being able to say, I don't have all the answers, but let's work on this together. And I'm going to guide us there. It's being authentic, but at the same time, understanding that you're still shouldering the burden of helping people move forward.



Megan:

I don't know if you can really accept support or embrace support in any way, unless you have a little bit of that vulnerability. I'll use the V word for it. I'll be able to admit that.



Heather:

Yeah. So I think being vulnerable, that's what good support looks like from the standpoint of, the leader who's looking for support. From the viewpoint of the supporters, good support is being able to listen and being able to really sit with the information and not necessarily, you know, it's being able to weigh when do you offer advice and when do you have the role of just being that soundboard and taking it in. And that's a fine line when you're supporting a leader of when to do either of those.



Megan:

If you are receiving support, I'll put that in some air quotes, and someone's not listening, if they're not really matching it. I'll always say that leadership quality of meeting you where they're at, it's not good support. I love that vulnerability and listening are kind of those key components for, it sounds like even the support to be successful or effective. It makes me think of all the coaches and consultants out there that don't listen to clients, right? And we've all had someone in our life that didn't listen and they thought they were supportive. Doesn't always end up the case. I think for a leader as well, really understanding if they want to be supportive to others. Recognizing and saying, hey, that person has to be vulnerable in order to accept this, but also being comfortable in that listening space. Exactly. Okay, so we've identified what that good support looks like. I don't even wanna ask what bad support looks like because we know if there's no vulnerability. I will ask, what does bad, what does it look like when that's not working?



Heather:

I mean, really simplest answer is bad communication. It's really like, just think of all the things that make up good communication and do the exact opposite. So I'm just saying a few examples of when you have leadership teams and the CEO, and they were not communicating well. And if you could fix that one thing, create a place, create a method, create a comfort zone, a language, a way to communicate that works for both. Like you said, coming like halfway across the bridge. you know, meet each other in the middle when it comes to at least communication. You may not agree, you know, agree to disagree type, that's okay because it's always good to have people in your leadership team who don't agree with you and get you to think outside the box and get to like push the envelope of what your comfort zone is and get you to think, you know, more strategically. But being able to at least communicate in the same way and being able to understand each other. If you can fix, if that's not working, that's the biggest one for a bad support system.



Megan:

And I think everyone's thinking of those personal examples and like, oh yeah, we'll just chalk it up to bad communication. No, it feels so much more personal than just bad communication. and feel like all that bad communication you start to take on yourself. So we have good support, we have bad support. I'm gonna say, what if you're just like, I don't need support, I don't want it, I don't, and completely rejecting it, because that's your other option.



Heather:

So, you know, at that point, I find the best leaders are ones who are lifelong learners. So ones who may say that they don't want support, they may get it in another way. So it may not necessarily be through people, but they may be avid podcast listeners. They may be audible listeners. They may read a lot of books. They may attend a lot of webinars. There may be another way that they're filling that support role. I'm thinking positively. They may be finding another way to fill that support role. And that's OK, because there's lots of different ways to learn. There's lots of different ways to improve ourselves. And everyone has differentiated learning is an important thing to be aware of. So it may be that. However, if they fall into the category of saying that they don't need support, If you are theoretically their supporter, that's when you listen, step back and give them the space to let them recognize when they do and when they're ready. I know you and I have talked over the years about coaching and what makes a good coach. And part of that is understanding at that moment in time, how coachable is that individual? How ready are they for change? And if a leader says in a moment at that time that they don't need support, it's a moment, it's a specific time. So then you just have to be vigilant and watch to see when they do need that support and when they're ready.



Megan:

What do you see from a lot of your clients when they are ready? What does that mean or look like? Because I don't even know if I'd be able to identify it. It's hard to get over that hurdle of saying, raising your hand. Are there earlier warning signs than just, oh my gosh, I'm completely overwhelmed, I need support?



Heather:

Well, I think this is where leadership development comes in. is you as a coach or as an advisor, sometimes it's the chairman of the board is in that supportive role of the CEO or the leadership team or one of the leaders. Sometimes it's a coach, sometimes it's an advisor or a consultant. But once you realize that change needs to happen for that individual or the company is continually to be there to show up, and talking to them about what that change looks like, because they may not be ready for it now, but after three months of talking about it, maybe you encourage them to take a course, maybe you ask them to read a book, maybe you introduce them to people in your network who have gone through similar things. Like there's ways to just kind of nudge them in that direction, to expose them to the information so that then six months later, they say, you know what, I'm ready now, I'm ready for this.



Megan:

I love that you're looking at it from these different flavors and different versions of what support can be. Support can just be information, it can be a person, it can be a resource. Most likely it's probably people in the actions or behaviors or even just listening or advice that offers up that support piece, but there's almost what you're saying is it's all contingent on change. Yes. So change is kind of that catalyst of either you're preparing for a change, and so you're getting that support. And as you have that development piece for it, it's initiating change, right? We can't do it all on our own. We can't do it by ourselves. And finding what that support team, systems, resources are in order to support that change for success.



Heather:

I knew we'd enjoy this conversation. It's really, it's a lot, it is a lot. I like that you were centering around change because, you know, you talk about preparing for change, but it's also responding to change. You know, something dramatic happens in your industry. What do you do? You know, half of your workforce leaves. What do you do? You know, there's, at the top, that can be a very, those can be very lonely moments. and that you're expected to find the answer when things don't exactly go the way they're intended, or there's a trigger event or a shock of some sort.



Megan:

And I love the word that you used there, that lonely word. We were riffing beforehand, we were talking about that. It's lonely at the top. Can you elaborate more on loneliness and support and how those work together?



Heather:

Yeah, so the concept, and we've kind of talked about this, is that as that leader, you're expected to report to a board of directors. And you're expected to lead the people underneath you. Well, then who's talking to you? You may have your C-suite that you can rely on. But what I have often found is it can feel lonely because there's a lot of information you can't give all at once to any one person necessarily when you're trying to decide what to do, or there's proprietary information, or the numbers aren't being released yet. And it gets very lonely because I don't know who I can talk to. You know, one way I've heard that works very well is to have your own personal board of directors. So those people that you rely on that may have nothing to do with your industry, but that you've built over time. And this concept I learned through a talk I saw from Anissa Muthana, who's the CEO of not one, but two manufacturing companies. And she's a rock star to say the least. But her, you know, the way she was talking about this, I've really, I think I saw this talk like two years ago and I've really, I've kept up with me and I've shared it because the concept is you build your trusted advisors. you know, who do you rely on when you make the biggest decisions in your life? Well, as a business owner, and especially if you're a founder or an entrepreneur, that business is so much a part of you and so tied to you. One of the business owners I talked to today described, and this was like a person who you would normally not think mention emotions because it's a very emotional thing when you're that tied to your business. So who do you rely on to make those big decisions, both in your personal and professional life? And having that board of advisors, having that person you can go to when you're like, this is an issue, who do I talk to, I think is very important. And one way to combat that loneliness that may be a little bit easier to take up or to swallow than some of the other methods.



Megan:

I can only imagine the different flavors of what that loneliness takes on for people, the different versions of it. I know you have your own podcast, the Growth Plus Exit podcast, where you really have that opportunity to interview. business owners, interview those CEOs and sweet, sweet executives on talking about that experience in building their own businesses, in exiting them. I'm curious, do you have any like little teasers that you can share the stories of what that loneliness has looked like for them?



Heather:

What I find most inspirational about talking about that role is the transition that those leaders take on when they start the role. if they weren't the original founder, they were brought in and what that looks like. So you come in alone, you've been hired by the PE company or whatever, and you have to run or there's been an issue with the company and you're brought in. So that moment of loneliness and how it takes time. to win the trust of the company. And then, you know, also thinking about the moment of loneliness when you're making the decision on what to do with the company. Do you grow it? Do you sell it? Do you merge with another company? What I found interesting in that second example, so we're talking about like the beginning and the end of the leadership role, basically, I find that those are the two points that can be most lonely. What I found is the business owners and the exec CEOs that I've interviewed, that second one at the end, when it's worked well, is when they've been collaborative. that they've been collaborative with all the stakeholders involved with that decision moving forward. And that can be everyone from board of directors, PE company, the company that's acquiring them, the employees, the leadership team. They describe that decision-making process as collaborative. When they do that, it tends to be the successful stories. So they're not doing it alone. What I'm saying is like basically, like they may feel lonely at the onset of having to make that decision, but when they find success is when they don't do it alone.



Megan:

The decisions are yours and they are lonely decisions to make because no one can make them for you. But how those decisions get executed needs to have the support behind it and it needs to be collaborative in order for it to be successful. Absolutely. That's so powerful to be able to get those lessons from so many other people. Knowing that it is so painful to be in that place and so beneficial when you do find those resources and that support system, what do you see stopping most people from getting that?



Heather:

A lot of startups or entrepreneurs who are in the thick of it, it's very easy for them to work in their business instead of on their business. So it's having that, I'm constantly putting out fires, like you talked about early, everything is on their shoulders. It all comes, the buck stops here, all the decisions are theirs, everything. And if they haven't learned how to delegate, and that takes time, that's a hard lesson to learn, when to delegate, It definitely, that's the point where things can go wrong and when they need to reach out. So I think part of the problem is they're so intensely working in their business and dealing with those day-to-day fires. I think the best way to combat that or to make sure that doesn't happen is by having them have a long-term coach you know, having CEOs or leaders in general, make sure that they're doing those, you know, check-ins quarterly with someone that can help them combat, you know, getting into those bad places where you're so focused, heads down, that you're missing opportunities. And it's hard to take time for that, which is why I'm saying quarterly. Ideally you'd say, I would say, meet with your advisor weekly, have a half hour call, have an hour call, that will, you'll find that your business moves so much faster, you'll reach your goals faster. There's so many good things that happen when you have that continuous support, just that one person you can talk to and bounce ideas out at a minimum. However, realistically speaking, knowing the budgets, knowing like what their, their day-to-day struggles are, you know, trying to just keep, make payroll that month, whatever, when you're in a high growth company, it's so easy to keep heads down and not see what's around you. And by having the practice of doing that, it allows you to invest in yourself and in your company and forces you to step back. So it's more than just working on your leadership or helping you to not feel lonely. It's allowing you to take that deep breath and see from 30,000 feet what's going on. So that a lot of times that's when those big aha moments happen when you're like, oh my gosh, my industry is shifting this way and I'm not even recognizing it. Why am I not recognizing it? We need to do something about that. So it's those big aha moments that can prevent a lot of disruption later on. If you take the time and you make a regular practice to step back and look at the big picture. And I think it's the best way to do that is with a coach or an advisor.



Megan:

Right, I think that consistent reflection, pulling yourself out of it, having someone else, even I will say you have the great, you shared the insight on having your personal board of directors. And if you are getting into that practice, if you are able to be a little vulnerable, if you're able to think critically about it and reflect deeply, you're going to not just avoid it, avoid the landmines that come with it, but actually be more prepared and more supported through the change process because everything is change. Change is the only constant that we're having. Definitely, definitely. So Heather, we're just about wanting to wrap up here. Are there any other words of wisdom or advice or something that you want to share when it comes to building out that support and making sure that you're getting the right support for yourself and your business?



Heather:

sooner rather than later. Don't wait. Don't wait to get support. And a couple of other ways to get support that I forgot to mention, now that I'm thinking about it, is to find those business groups. I know there's a lot of local CEO groups or coffee groups or there's a lot of organizations and associations. They can also provide that. It's really nice to sit down with somebody who's in a similar situation to you. Good example, I'm going to an event later today that's hosted by three different incubators. One's a manufacturing incubator, one's a tech incubator, and then the other one is an innovation incubator. And the idea is being able to be in a room where people are in that high growth mode, are working with entrepreneurs, working with startups, are building their companies, are really doing a lot of that high intensity work. You're not alone because you can see them going through it as well. So surround yourself with a network that can support you in that way.



Megan:

Well, we will wrap it up there. So, so important to do this in one way, shape or form. You've given everyone a ton of different ideas and resources and solutions to make sure that they are getting the support themselves. They're not missing out on anything. And they're of course getting all the benefits of avoiding those landmines and the pain and the loneliness and the suffering that often happens without it. I do recommend reaching out to Heather if you do have questions about what that support could look like for you. especially if you are in that CEO spot, you are looking at that potential exit, if you are looking at that growth opportunities, or if you are looking for more of that and you are not seeing those pictures, that's exactly why you need to be reaching out to someone like Heather. But please do listen to her podcast. The Growth Plus Exit podcast is really going to give you some of those inside stories and continue this conversation, I'm sure, in a very different way.



Heather:

Thank you so much for joining me, Heather. Oh, thanks so much, Megan. Always a pleasure.



Megan:

Thank you so much for listening to this episode of Culture Conversations. I'm your host, Megan Robinson, founder of eLeader Experience, a professional leadership development company. Today, we shared actionable ideas to navigate the evolving workplace landscape, compete for talent, and build cultures that maximize potential. If you're looking to learn more about how to support your organization's leaders, you can learn more about our work at eLeaderExperience.com. Now get out there and contribute positively to your organization's culture with your own conversations.

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