I've Led My Company for 30 Years. Here Are 5 Leadership Beliefs I Had to Unlearn

The CEO of Learnit on the deals he walks away from, the hires he no longer makes, and why he stopped treating his team like family.

About 10 years ago, one of the best people on my sales team walked into my office and told me she was leaving.

I was stunned. She'd been at Learnit for two years, and she was crushing it. I'd given her what I thought every high performer wants: autonomy, space, and nobody looking over her shoulder.

That was the problem.

Her exit was one of several moments that forced me to look hard at what I believed about leadership. I've run Learnit for more than 30 years, and I've changed my mind about a lot. Sometimes I made mistakes. Sometimes I missed what was right in front of me. Sometimes I just gained enough experience to see things differently.

Here's the pattern I keep running into. A belief that helped you become successful won't necessarily help you stay successful. The world changes. Your people change. You change. If you don't revisit your assumptions, they can hold you and your team back without you noticing.

Here are five beliefs I used to hold close, and what I believe now.

1. You don't have to win every deal

For years, I treated every prospect as a deal we had to close. I wanted to do right by everyone.

So we over-promised. Usually we delivered, but we lost money doing it. We over-committed resources and stretched ourselves too thin. Chase every deal long enough and you start losing clients, because you can't deliver at the level they need.

Now we decide which deals we want and walk away from the rest. Three kinds of opportunities get a no.

Work outside our core. Learnit focuses on human skills like leadership and the mindset around AI adoption. When a prospect asks for HR compliance or AWS training, we say no and point them to someone who can serve them better. That builds trust, and those clients come back.

Customers who've burned us. If a client nickel-and-dimed us or set us up to fail, we don't work with them again.

Great opportunities we can't deliver well. This is the hardest one. The timeline might be impossible, or the scope too big to scale. Staying inside your strengths protects your team and your margins.

And when you lose a deal you badly wanted, don't take it personally. Ask the prospect what you could have done differently.

Before you pursue your next opportunity, ask three questions.  

1. Is it in our core strengths?  
2. Is it best for our team?  
3. Are we excited about it?  

If you can't say yes to all three, consider passing.

2. Pedigree is not fit

I used to see Microsoft, Oracle, or Google on a resume and think, We have to hire this person. Same for anyone coming from a big-name competitor.

Then they'd arrive, and it was like going from the steam room to a cold plunge. Someone used to vast resources suddenly had far fewer.

Hiring from competitors went especially badly for us. The knowledge those hires brought often came with a know-it-all mentality, when what we needed was a learn-it-all mentality.

Now I hire for values, attitude, and aptitude. Success somewhere else doesn't mean someone fits here.

Start with the team you already have. Do they align on all three? Then look at the roles you're hiring for now. Which interview questions will show you whether a candidate's values match what your organization needs?

3. Your company is a team, not a family

I believed loyalty should run both ways. When employees left, I took it personally, as if they owed it to me to stay.

A longtime member of our team changed that for me. He was with Learnit for 15 years, and we treated each other like brothers. But he'd hit his capacity. He was exhausted, and he probably stayed five years longer than he should have. When we finally sat down and talked, he moved on. Today he's crushing it in his new role.

In Amp It Up, former Snowflake CEO Frank Slootman argues that you owe it to your organization to run it like an elite sports team, with the best players on the field at all times. A family can't operate that way. Uncle Joe is always invited to Thanksgiving dinner even if no one really wants him there.

The people who got you to one level may not be the people who get you to the next. Is someone on your team getting your loyalty when they'd honestly be better off somewhere else? Plan how to make that transition. It helps you, and it helps them.

4. Your stars need you most

Conventional wisdom says to give top performers autonomy, skip the micromanaging, and spend your time on the people who are struggling. That's exactly what I did with the salesperson who walked into my office.

When I asked what happened, she told me: "I didn't feel challenged. I didn't get any feedback. I didn't get any constructive criticism. I was left on my own to do my own thing, and I didn't feel like I was growing at Learnit."

That was a hard pill to swallow.

Now I spend real time with my top performers. I challenge them and stretch them, because that's what made them top performers in the first place. With underperformers, I work to get them to the middle or help them move on. With the middle, I look for ways to make them better.

Who on your team is crushing it right now? Are you still having difficult conversations with them about where they can improve? Ask them where they want to grow.

5. Stop paying the trust tax

I've been let down and cheated in business. For a long time, I carried that into every new relationship, guarded and cynical. I call it the trust tax.

We once paid $2,500 to send an employee to a conference. A week later, they quit and went to work for the company that ran it. The next time someone asked for training, my first thought was whether they'd leave right after.

That was the wrong question. You want your people to grow. If they leave, they leave. (That employee’s departure turned out to be the best thing for us.)

Now I go into relationships assuming people have good intentions. I'm not naive. I'll get let down sometimes. But staying cynical means missing out on what open relationships can give you. Trusting people strengthens the relationships you already have, and it makes you a happier person and a better leader.

So ask yourself honestly: Do you enter business relationships open-minded, or braced to be taken advantage of? If it's the second, take a step back.

The belief behind the behavior

Each of these beliefs made sense to me once. Some even worked for a while. That's what made them so hard to see.

When a team underperforms or a great person walks out the door, the first instinct is to examine what you did. Examine what you believed when you did it, too.

Pick one of these five.  

Is it shaping your decisions right now? And is there a belief not on this list that you're starting to question?

Thirty years in, I’m still unlearning. That’s the job of a leader.  

The beliefs that got me here won’t write my next chapter. I always have to be willing to rewrite what I know. And I hope you are too.  

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Damon Lembi is the CEO of Learnit, author of The Learn-It-All Leader, and host of the Learn-It-All™ podcast.