Leadership coaching: stop being the bottleneck
After 19 years building my two MSPs, I’m hands-off. Both companies run under presidents. Here is what it took, and how you can get there faster.
My story
My name is Wim Kerkhoff. For nearly two decades, I’ve owned two MSPs: ImprovingIT and Crafty Penguins. For the last several years, I’ve been completely hands-off. Both companies run under their own presidents while I focus on TopLeft. It wasn’t always this way.
I didn’t hire my first coach until four years into the business. I thought if I just worked harder, the systems would eventually click. Instead, I was the bottleneck for everything: tech work, hiring, vendor payments and sales. I couldn’t even take a vacation without checking my BlackBerry every ten minutes.
I realized I didn’t have a true business until I had an effective manager to support me, real sales and marketing in place, and wasn’t the air traffic controller on every task. I stopped trying to be the hero. Over the last 15 years, I’ve worked with:
- Productivity coaches, to stop confusing busy with effective
- Traction EOS implementers (EOS is the Entrepreneurial Operating System from the book Traction), to document how decisions actually flow
- Marketing and sales coaches, to move out of reactive mode
- A psychologist (who I still see weekly), to remove limiting beliefs and habits
Today, my teams own their work. Managers make decisions instead of escalating them. Many leaders are stuck where I was: not having the right mindset, values, people, coaching skills or structures.
What I actually do
I don’t do regular coaching myself; I don’t have the time. I chat with people like you (MSP owners, service managers, project managers and team leads) about where they’re stuck. Then I connect you with the right coach, consultant or program for your situation.
Sometimes that’s one of the external coaches I’ve worked with or know well. Sometimes it’s one of TopLeft’s programs, like Accelerator group coaching, Agile ScrumMaster training, or a Rapid Implementation project. Sometimes it’s a combination.
This isn’t a revenue thing for me. I don’t get paid referral fees. I do this because I wasted four years trying to figure it out alone, and I know what the right coaching can do.
Meet some of my coaches
Over the years I’ve worked with coaches who specialize in different things. Here are three I’ve featured on my podcast. I know others who specialize in EOS, sales, marketing and more, and I’ll suggest some after our first call.
Francesco, mindset and leadership
Francesco helped me work through the mental blocks that keep leaders stuck, like control habits, limiting beliefs and the fear of letting go. Our podcast covers the invisible barriers that stop owners and leaders from stepping back.
Watch: podcast with Francesco (part 1) →
Nate, operations and scaling
Nate helps leaders build systems and teams that can scale. He’s worked with me on delegation frameworks, decision rights, and getting middle managers to actually manage instead of escalate.
Watch: podcast with Nate →
Melvyn, Agile and Lean methods
Melvyn is an Enterprise Agile Coach. He helps leaders build teams that improve flow, reduce waste and collaborate instead of working in silos, from a background in large service organizations (IBM, Accenture).
Watch: podcast with Melvyn →Who this is for
This doesn’t make sense if
- You think a new tool will fix prioritization or accountability
- You’re not willing to have hard conversations (about toxic people, broken processes, or your own control habits)
- You want a quick fix that lets you keep running things the same way
- You’re under $500K revenue and still figuring out basic service delivery (you probably need different help first)
This makes sense if
- You’re stuck approving things your team should own
- Your direct reports escalate instead of deciding
- You can’t take time off without everything falling apart
- You’ve got a talented but toxic person you keep making excuses for
- Your team’s priorities get distorted by whoever yells loudest
- You’re waiting for a superstar hire that never shows up
- You’re a service manager drowning in escalations your L2s should handle
- You’re a project manager who can’t get engineers to own their tasks
- You’re an owner who wants to step back but doesn’t trust the team yet
Types of coaches in our network
EOS implementers
For MSPs that need clear accountability charts, defined decision rights, and a framework for running the business with less chaos.
Marketing and sales coaches
For MSPs that need to stop reacting to inbound chaos and build predictable new business.
Productivity and time management coaches
For leaders who are busy but not productive, struggling with prioritization and focus.
What happens next
Book a virtual coffee with me
We’ll talk candidly about where you’re stuck, what you’ve already tried, and what success looks like for you.
I’ll recommend the right path
That might be:
Some tactical fixes you can make, from what I’ve learned
A warm intro to a suitable coach
One of our own TopLeft coaching programs
Or a combination
What about TopLeft?
You don’t need TopLeft to benefit from coaching. If you do use TopLeft, or decide to, here’s how it fits.
TopLeft makes work visible. You see where projects are stuck, which tickets are blocked, and who’s overloaded. That visibility surfaces the real issues: prioritization, ownership, decisions bottlenecking at the top. Coaching helps you resolve what visibility reveals.
Our Accelerator group coaching, ScrumMaster training and Rapid Implementation programs combine TopLeft’s workflow tools with the habits and culture changes that make them work. The coaching stands on its own, though: if you use a different PSA or workflow tool, we’ll help you with whatever you have.
The real reason I do this
I spent four years thinking I could figure it out alone. I was wrong. The coaches I worked with helped me step back from my MSPs and build companies that run without me. That let me focus on TopLeft.
Most MSP leaders spend their best years stuck in the weeds because they think coaching is for people who are failing. Coaching is for people who want to stop wasting time on things their team should own.
Whether you’re an owner trying to step back, a service manager buried in escalations, or a project manager who can’t get engineers to take ownership: if you’re the bottleneck, let’s talk.
Book a virtual coffee with Wim
You’ll speak directly with Wim to check fit and goals. If coaching is right for you, we tailor the engagement through focused coaching or workshops that strengthen your MSP’s leadership, speed up project delivery and create lasting change.