How to Manage Someone Who Has More Experience Than You

We hired our first VP of sales about a year after we dropped out of school to pursue our startup dreams. We’d raised $2 million in funding, hired a handful of our friends and classmates, and moved into a big house together to get to work. But while we had secured a few early customers, we were really struggling to figure out a repeatable sales model.

He would change that. We just knew it.

With more than a decade of experience, he’d be our first “adult hire.”

The anticipation of his first day built for weeks—every problem seemed just a little less significant because we knew they’d be solved by him soon. We were so ready to have all of our questions answered, all of our problems solved. We were so ready to drop everything we’d been doing and follow his every command. We were ready to be led wherever he wanted to take us.

And then, when we sat down for our first meeting, he began asking me for guidance—including on some of the very same questions I’d written down to ask him. He made it clear he was ready to be led wherever I wanted to take him.

I didn’t know what to do. So I decided to be honest: I told him I had no idea, and that it was his job to figure it out.

For nine months, I watched him confidently lead us with new plan after new plan, each one failing after the other. We followed his every command, blindly confident in whatever we were asked to do.

After nine months, he left. We hadn’t solved our sales problem, we didn’t feel any closer to solving it, yet we’d spent a lot of money and wasted a good amount of time.

What went wrong

Five years later, I’ve learned that the best manager-employee relationships are partnerships. They are 1 + 1 = 3 situations in which the two people’s strengths and weaknesses complement each other. They are collaborations.

One mistake I made with that first VP of sales, I’ve realized, was that I wasn’t confident in leading or managing him because I viewed him as the expert. What I failed to recognize was that yes, while he was the expert at sales, I was the expert at our company, and our product specifically. More importantly, I was the expert at all the nuanced challenges we’d faced while trying to sell our product.

Had I had more confidence in what I’d learned from attempting to sell our product for a year, and had I been more collaborative and proactive in sharing those learnings and working with him instead of blindly following him, things may have turned out differently.

Lessons learned

Today I manage a team of 50 employees, while still having never even had a manager myself.

I’m still constantly working to find the right balance, but here are some of the things I’m consciously thinking about and attempting to do:

First, I’m upfront with every new employee about having never had a manager. I push all of our employees, but especially the ones who have had managers before and have more experience than me, to directly give me critical feedback on how I’m managing the team.

Second, I’ve learned to have more confidence in the aspects of our business that I do know a lot about, even as I remain a follower in the areas I don’t. I’ve learned to ask a lot of questions around areas of the business that I’m not an expert in and try to put a lot of trust and faith in the decision-making of the members of our team who know much more than me about their particular domains. I’ve learned that challenging the team on decisions I clearly don’t have a lot of experience in is one of the fastest ways to lose their respect and confidence. At the same time, when it’s an area in which I have expertise based on years of running the business, I’m much more confident in providing clear direction.

It’s easy, especially as a first-time founder, to try to overcompensate for areas of insecurity or doubt, but I’ve found a strategy that works better than trying to be someone who I’m not—admitting where I don’t have expertise, and also, where I do.

Tom Coburn is the founder and CEO of Jebbit.