Improving your MSP leadership skills doesn’t have to be complicated.
In my early days as an entrepreneur, I thought leadership was about directing, not connecting. I focused on goals, metrics, and outcomes. The problem was that I missed the most important element: the humans who achieved them.
Leadership isn’t about steering the ship, it’s about making sure your crew is empowered, supported, and aligned with the mission. That realization changed everything for me and my team.
For MSP leaders, focusing on the tools and strategies you need to thrive in a competitive market is, of course, very important. But while technology is a game-changer, it’s leadership that sets businesses apart. You can have the best systems in the world, but without an engaged and empowered team, those systems fall flat. The leadership strategies in my book All In are about bridging that gap and investing in your people. When you do this, you develop an unstoppable team that can take your business wherever you dream.
Leadership Is Investing in People
When I started my most recent business, Kelsey was my administrative assistant. She was wonderful at her job. She was efficient, detail-oriented, and great at anticipating the needs of a guy like me who’s constantly chasing new ideas. (That’s a nice way of saying I’m a little chaotic.) But as time went on, I began to notice something more. Kelsey wasn’t just good at her tasks; she shared my values. She saw gaps I didn’t even realize were there and filled them with creative strategies.
When it came time to hire more staff, I put Kelsey in charge. She didn’t just look at resumes and job descriptions. She looked for people’s innate talents, their passions, and their alignment with our mission. Instead of trying to fit skills into boxes, she sought out individuals who cared about our business as much as we did.
That mindset changed everything. Today, Kelsey is our company president because, frankly, who better? Together, we’ve built a team that’s as dedicated and innovative as I am (and sometimes even more so). This kind of dynamic isn’t just rare, it’s replicable. But it requires one thing: going all in on your people.
Align Vision with Your Team
Leadership isn’t just about knowing where you’re going; it’s about making sure your team wants to go there too. If your vision doesn’t resonate with your team, it’s just a pipe dream. But when personal and professional goals align, you create a powerhouse team that’s ready to tackle anything.
All In explores the strategies I and other business leaders have used to make this alignment happen. It starts with understanding what drives your team members. What do they want to achieve, not just in their careers but in their lives? How does their “why” intersect with your business goals? When you align those two, you’re not just creating a job for someone, you’re creating purpose.
Purpose is a game-changer. It’s the difference between a team member who clocks in and out and one who shows up ready to give their best every day. When your team feels personally invested in your business’s success, they’re not just working for you, they’re working with you.
Understand the Human Connection
We talk a lot about technology, systems, and strategies in business. But at the end of the day, businesses are run by humans. And humans thrive on connection.
Empathy, communication, safety, and trust are the cornerstones of great leadership. Your team isn’t just a resource. They’re people with hopes, dreams, and challenges. When you lead with humanity, you create loyalty and drive that no “skill” can fulfill.
I’ve learned that being “all in” as a leader means showing up for your team, even when it’s inconvenient or uncomfortable. It means having honest conversations, listening more than you speak, and being willing to admit when you’re wrong. It also means celebrating their wins, big or small, and acknowledging their contributions.
When your team feels seen, heard, and valued, they’ll go above and beyond to help you succeed. And when things get tough, they’ll stick with you because they know you’ll do the same for them.
Start Here to Boost Your MSP Leadership Skills
Leadership might sound lofty, but it doesn’t have to be complicated. Here’s a simple question to ask yourself if you want to improve your MSP leadership skills:
How well do I know my team?
Do you know their strengths, their frustrations, their goals? If not, that’s your first step. Schedule one-on-one check-ins. Ask questions like:
- What’s one thing we could do differently to better support you?
- What’s something about your job that you find most fulfilling—or most frustrating?
Then, take action. Even small changes can have a big impact. When your team sees that you’re listening and responding, they’ll trust you more and engage more deeply with their work.
And if you missed the last Mike Drop, check out New Year, New You: Dial In A Marketing Strategy To Stand Out
