When I was the CEO of DragonDev there was one role I never fully knew I needed and when I finally recognized it – I never managed to fill it.
Not a VP or C-Suite position. Not a board member. Not another consultant with a deck and a framework that is predicated on purchasing their ‘system’. I wanted someone at my level who’d tell me the truth instead of what I wanted to hear, hand me something useful instead of theory or hollow promises, and be fully in my corner no matter what.
If you’re a SMB leader, some version of the “need” list below will probably sound familiar:
- Someone to strategize with who isn’t guessing at what you’re facing because they’ve been there.
- Someone who mentors through actions, not just handed out advice from a book or compiled it from AI
- A confidant for the stuff you can’t say or ideate with anyone below your level
- Someone who builds and implements something real, not just gives you a slide deck, a book they authored, and then a pat on the back as they leave the room
- A coach who draws the answer out of you with thoughtful and direct questions instead of using questions generated by the “newest business fad of the day” angle
- A teacher who elevates your thinking through mindfulness and empathy, not just helps you organize and prioritize your task list
- A true peer, someone who has the experience through the hard knocks of failing often and fast — without the cost or premium of a full-time hire at your level
- An accountability partner – someone who will hold you to the plan when needed, yet has the skills to flex the accountability when the wind changes direction
I learned these “needs” were not separate. The problem was I couldn’t hire each role even in a fractional capacity. Trying to piecemeal a solution to fill these gaps became too costly, complex, and convoluted to manage.
Nearly two decades running my company and there was an obvious void the entire time. I began to think what if one person could fill these needs: a real peer, on demand, who isn’t afraid to tell the truth.
Recognizing the Isolation & Mindfulness
Seeing these needs while in my own state of isolation was eye-opening. I became mindful and took note.
The reality is most SMB leaders don’t see their own isolation, let alone dive into it with mindfulness. Isolation is not something that is tangible and recognizing it can often be tricky. Most leaders have never thought to identify it as an issue or have something in their toolkit to deal with it. Reality is that most leaders might think mindfulness belongs in a yoga studio and not a daily habit to leverage in business for sustained growth.
Mindfulness isn’t just a wellness trend; it’s a documented leadership skill and need where things like isolation can be identified and embraced. Merriam-Webster describes mindfulness as paying full, nonjudgmental attention to your own thoughts and experiences as they’re happening.
A systematic review of mindfulness research on leaders found that regular practice measurably improves attention focus, decision-making, and the ability to manage reactions and judgmental thinking under pressure — precisely the capacities that erode fastest when you’re running a company alone and feeling isolated.
Here’s the power of being mindful: identifying and making the connection to something like isolation beyond the crisis of the moment doesn’t stop with leadership. Research on leader mindfulness has found it is associated with better job performance, higher engagement, and greater job satisfaction among the people who report to a mindful leader, along with lower burnout across the team. A mindful leader changes the entire room, not just their own decisions at a desk. Being aware and dealing with the seemingly low-grade pain points – like isolation – sets you and your team up for success.
It’s Not Just You
The need to fill the void caused by isolation isn’t a soft want or complaint. It’s a documented pattern.
A Harvard Business Review piece on CEO loneliness points to research showing nearly half of CEOs report feeling isolated in the role, and a majority of those believe it actively impedes their performance (HBR, 2024). Separate survey data from RHR International found similar numbers, with most of those leaders saying the isolation gets in the way of doing the job well (Vistage).
The reason isn’t a lack of people around you. It’s structural.
Being the ultimate decision maker inherently sets you apart from everyone else in the organization. Because you have the ability to enact a nuclear option at any given time, people not only respect that, they also treat everything you say or do as different and as final.
As a SMB leader, things will always get filtered before they reach you because of your position. Your team can’t be fully objective about your decisions, and your board wants outcomes more than honesty. Ultimately, your team lacks the depth needed to discuss and ideate around the bigger picture, and your board isn’t privy to the day-to-day activities inside the organization. None of these people can fill the void caused by isolation.
One CEO peer group resource put it plainly: most business advice comes from people who’ve never carried your level of responsibility — consultants offer theory, your team offers operational insight, but neither can offer both distance and lived experience at once (Vistage).
That’s the gap. No one around you has been in your shoes.
It’s not that you lack advisors, coaches or consultants – they are a dime a dozen. It’s that most of these people have not actually stood where you’re standing with the depth you need -> all-in-one at the same time and place.
What I Discovered
I never found that person for myself. Instead, I had to piecemeal parts of it together. I had the executive coach, I joined Vistage hoping I would find peers I could bounce ideas off, and even my personal therapist had become a de facto confidant when faced with the emotional aspects of my business.
I called it “Team Keith”. I only met with each of these people an hour at a time once a month and none of them were connected to each other. Not being connected presented the issue of inconsistency, which meant “Team Keith” was siloed by virtue of their independent relationship to me.
I could never find that all-in-one counterpart I wanted for my company.
After moving on from being the CEO of DragonDev I realized the value of this sort of role for other SMB leaders. This kind of thinking was outside of the box. It didn’t involve a program from a consultant. It wasn’t a fixed twelve-week engagement with a graduation date for a system and a framed certificate of completion.
It was creating a collaborative relationship with a trusted peer-like strategist to build the scaffolding for change while the company did what it needed to do – unencumbered.
The concept I had was to step back once the company could stand on its own, and then with the help of a strategist move the scaffolding to the next part of the overall plan to elevate the business. Because that’s how growth actually works. It doesn’t happen in a silo – once and then it’s done. It requires applying agile principles to every small step along the way for positive change.
I knew I needed an all-in-one strategist, confidant, builder who hands you something real instead of a theory, a former CEO and mentor who’s made the mistakes already along with the accountability partner who checks in to make sure your vision is intact. This was not a clever idea for creating a quasi-business partner. I spent years piece-mealing those holes because they didn’t exist in a way I needed, which is exactly why it’s worth naming, and worth you looking for those resources.
If This Sounds Familiar
You may not need all of the things I outline on the list above. Most SMB leaders only need a few of them depending on their own situation.
That said, if you feel the absence of such a seat in your own organization, that’s worth naming, being mindful of it and exploring it. If nothing else, connecting to the need may lead you to fill the voids that don’t get the proper attention.
The point isn’t to convince you to hire someone who demonstrates only parts of those needs. It’s to convince you that your isolation is real, and as a SMB leader you should find ways to fill those voids, whether it is one person or a few key people.
Filling the voids caused by isolation will not only help with the chaos of running a SMB, it will also elevate you and those around you in ways that you had hoped for and never expected.
References
Harvard Business Review. “CEOs Often Feel Lonely. Here’s How They Can Cope.” (2024)
https://hbr.org/2024/12/ceos-often-feel-lonely-heres-how-they-can-cope
Vistage Research. “Why Many Leaders Feel Lonely at the Top.”
https://vistage.com/research-center/personal-development/wellness/20210308-lonely-at-the-top
Vistage. “Peer Advisory Groups: Our Approach.”
https://vistage.com/membership/our-approach
“From personal wellbeing to relationships: A systematic review on the impact of mindfulness interventions and practices on leaders.” ScienceDirect (2021).
https://www.sciencedirect.com/science/article/pii/S1053482221000164
“Mind the Silver Bullet Thinking: A Multilevel Study on the Impact of Manager Trait Mindfulness on Subordinate Objective Job Performance.” PMC.
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6764216
“The double-edged sword effect of leader mindfulness on employee taking charge.” PMC.
