What I Learned Working with a Board (After Years of Going It Alone)

When I returned to Management One in 2025, I came back to something I’d never really had before: a Board of Directors.

I’d built and run M1 for years making every major decision myself. That’s how most entrepreneurs operate – you figure it out, you trust your gut, you carry the weight. And for a long time, that worked. But one of the reasons I originally sold the business was the loneliness of it. The weight of every big decision sitting entirely on my shoulders. The isolation of being the only person who could make certain calls.

Coming back meant stepping into a different structure. I had a board now. And I’ll be honest – I didn’t know exactly how to use them or what to expect.

The First Few Months: Over-Communicating on Purpose

In those early months, I communicated constantly with the board. Every decision, every challenge, every piece of progress. At the time, I wondered if I was overdoing it. But looking back, it was exactly what needed to happen.

Those first months weren’t just about keeping them informed – they were about building trust during a recovery period. We were working through difficult decisions together. We were stabilizing things that needed stabilizing. And we were building a business plan that would become the foundation for fundraising.

That intensive communication period served multiple purposes:

• It got their buy-in on hard calls when I needed support
• It taught me where they wanted to be involved vs. where they didn’t
• It helped me understand each board member’s strengths and how to use them
• Most importantly, it built real trust, fast

What I Already Knew (And What I Had to Learn)

Being prepared came naturally to me. Having my numbers ready, thinking through scenarios, doing the work before the meeting – that’s just who I am. The board experience reinforced that strength rather than forcing me to operate against my grain.

But here’s what I learned that wasn’t already natural:

The weight can be shared. The loneliness I felt the first time around – that sense that every major decision was mine alone to carry – that’s not how it has to be. Having smart people who understand the business, who’ve helped shape the plan, and who can help you think through the hard calls? That changes everything. Collaboration on big decisions isn’t weakness. It’s sustainability.

The sounding board piece matters more than I expected. I thought a board was about governance, oversight, maybe strategic guidance. I didn’t expect how valuable it would be to simply have thought partners at my level – people I could go to when the decision was big and the stakes were high.

Their care and concern exceeded expectations. I expected professional engagement. I got people who genuinely care about me and M1 succeeding. That changes the relationship from transactional to genuinely supportive.

What Works Now

We’re past the intensive communication phase. The difficult decisions got made. The business plan exists and we’re executing against it. The board relationship has settled into something sustainable:

I know what to share. Anything that would surprise them if they found out later – strategic shifts, real problems, big wins, decisions that affect the plan we built together. No surprises means trust goes both ways.

I know their individual strengths. I’ve mapped who to go to for what – financial thinking, strategic pattern recognition, operational expertise, network access. Our 1:1 meetings are productive because I’m using them for what they’re actually good at.

They participate meaningfully. They join our quarterly and annual EOS meetings, which means they see how we actually operate and can give direct feedback on my performance and the team’s performance. That integration into the rhythm of the business makes them genuinely useful, not just governance overhead.

They teach, not just advise. They’re helping me develop as a leader. They know when to be tough and when to be compassionate. They’re problem solvers – they roll up their sleeves and help work through challenges rather than just pointing them out.

The Real Lesson

The loneliness at the top is real. For years I carried the weight of every major decision alone. I thought that’s what leadership meant.

But working with a board taught me that you can think more clearly when you’re not carrying everything by yourself. You make better decisions when you have smart people challenging your thinking. And you can execute with more confidence when you know others have looked at it and said “yes, this is the right move.”

I’m not just managing a board relationship now; I have people behind me. Steve and Matt have been thought partners, teachers, and problem-solvers throughout this journey. That’s the difference between leading alone and leading with the right support structure.

Being straightforward and honest, including sharing news that’s not always great  is critical to making this work. But when you build that foundation of trust, you don’t have to carry the weight alone anymore.

And that changes everything.

Marc Weiss is CEO and Cofounder of Management One, providing merchandise intelligence and planning expertise to independent retailers across North America.