Every Boss Is a Mentor or a Lesson.

If you’ve ever watched Bar Rescue, you know Jon Taffer as the man who walks into a failing bar, looks at the sticky floor and the warm beer, and yells at the owner until a vein appears on his forehead.

He is not the first person I’d expect to quote on kindness at work. But back in 2015, in an interview with Entrepreneur, someone asked Taffer what makes a great leader. He didn’t yell at all. He said this:

The greatest gift of leadership is a boss who wants you to be successful.

Not a raise. Not a corner office. Not pizza on Fridays. A person. Someone who is genuinely, reliably on your side.

I’ve spent a lot of years studying organizations, and especially the people who lead them. If I’ve learned one thing, it’s this: the leader makes or breaks the company. Not the product. Not the marketing. Not the fancy espresso machine in the break room that nobody knows how to clean. The leader.

So this one is a little more personal than usual. I’m writing it from the heart.

Mentors and lessons

Every boss I’ve ever had has ended up in one of two folders in my head.

The first folder is mentors. These are the people I respected and trusted. They believed in me before I’d earned it, told me the truth when I needed it, and made me better at my job and as a person. I still hear their voices when I’m about to send an email I shouldn’t.

The second folder is lessons. These are the people who didn’t have my trust, or didn’t support me when it counted. And here’s the funny thing: they taught me just as much. Every lesson was simply what not to do. That folder is thick. I open it every time I’m tempted to cancel a one-on-one because I’m “slammed.”

For most of my career, I assumed people stayed in the folder I put them in. Then I learned that isn’t how it works.

When a mentor becomes a lesson

I worked for someone for years who showed me a tremendous amount of care. They checked in. They encouraged me. They said all the right things, and for a long time I believed every word. If you had asked me, I’d have put them in the mentor folder without a second thought.

Then came a moment when it really mattered. A moment when I needed them to stand beside me. And they didn’t. When the pressure was on, they stepped aside, and I was the one under the bus.

(Helpful tip: the bus does not slow down so you can process your feelings.)

I won’t get into the details. They don’t matter here. What matters is what it taught me, because it taught me a lot.

I’ve spent my career in HR. I’ve sat in the room for more of these moments than I can count, usually on the other side of the table, helping leaders through them. So I recognized what was happening right away. What surprised me was how much clearer it made everything I believe about leadership.

Years of respect, trust and care can build a great leader and mentor in your life. But the moment the authenticity behind it goes away, everything crumbles to the ground. All of it. And just like that, a mentor becomes a lesson.

Care builds trust over years. Integrity is what keeps it standing on the day it gets expensive.

Leadership isn’t a costume

We’ve all seen it. A manager comes back from a conference with a lanyard and a new vocabulary. Monday, we’re “circling back.” Tuesday, we’re “leaning in.” By Friday there’s a whiteboard in the lunchroom that says FAIL FAST!, and nobody on the team is allowed to fail at anything, ever.

I love leadership books. My bookshelf is starting to sag. But reading Radical Candor doesn’t make you candid, any more than reading a cookbook makes you a chef. Being a good leader isn’t putting on a show, or wearing a mask of whatever you read that week or that month. The book is a tool. It’s not a personality.

And people can tell. Your team can spot a mask the way Jon Taffer spots a dirty beer tap: instantly, from across the room, and with a strong opinion about it.

Here’s the formula I keep coming back to:

• Care without candour is the boss who’s too nice to tell you the truth. Lovely to work for, right up until you walk into the same wall for the third time.
• Candour without care is the boss who tells you the truth because they enjoy it. Accurate. Exhausting.
• Care and candour without integrity is the mask. It looks like leadership for years. Then one day it costs something to keep it on, and it comes off.

You need all three. Integrity is the one that holds the other two up.

Trust comes first. Everything else comes second.

The key to any team working together is trust. It’s the foundation that has to exist before good things can happen. Your people need to believe you when you say what you say. Every time. Not just when it’s convenient.

I’m always inspired listening to Simon Sinek talk about leadership, and I think he’s dead on. In Leaders Eat Last, he describes a “Circle of Safety.” When people feel safe with their leader, they stop spending energy protecting themselves and start spending it on the work and on each other. He puts it this way:

Leadership is not about being in charge. It is about taking care of those in your charge.

Taking care of people when it’s easy is nice. Taking care of them when it’s hard is leadership.

How to tell your leadership is slipping

When leaders aren’t being good leaders, the symptoms show up fast. You just have to know where to look.

• People talk. If the most productive meeting in your building is the one in the parking lot after the real meeting, that’s a symptom.
• People disengage. The ideas dry up. Cameras go off. “That’s not my job” starts showing up in conversations it never used to.
• Venting replaces building. This is the expensive one. Your best people spend their energy processing their boss with their coworkers, instead of putting it into growing your business.

In a business of ten or twenty people, none of that is a side effect. It’s a cost. Every hour spent venting is an hour of good energy that could have gone into something great.

Be the spotter

Photo by Shoham Avisrur on Unsplash

When I picture the leader I want to be, I picture a spotter at the gym. When someone is lifting something heavy, the spotter stands right behind them with their hands hovering just under the bar. Near it, not on it. They want you to lift more than you did last week. They tell you your form is off before you hurt yourself. If the bar starts coming down, they catch it. And when you finish the set, shaking, they say, “That was all you,” even when they helped a little.

Once you see leadership that way, you start noticing the bad spotters everywhere.

We’re all still students

Here’s the part I have to say to myself as much as to you. Nobody finishes learning how to lead. I haven’t. We are always students of leadership, and the moment we think we’ve graduated is usually the moment we start slipping.

That means being honest about where we need to improve, and not letting our egos get in the way. Ego is what turns “I was wrong” into “it was a communication issue.” It’s what makes a leader protect their own reputation when they should be protecting their people. In my experience, ego is behind more lessons than bad intentions ever are.

1. Stand close. Know what each person is lifting right now. Keep your one-on-ones, even when something “urgent” comes up.
2. Hands near the bar, not on it. Let them do the lift. Every time you grab the bar, you take away a chance for them to get stronger.
3. Tell them about their form. Early, privately, and kindly. Saying hard things for the sake of someone’s growth is one of the most caring things you can do.
4. Catch the bar, especially when it costs you something. Take the heat in public. Do the coaching in private. That’s the moment your people decide whether everything you said before was true.
5. Check your ego at the door. Ask your team where you could be better. Then listen, say thank you, and don’t explain.

P.S. Norman, my springer doodle, would make a terrible spotter. He’d lie down on your chest mid-set just to make sure you were okay. Loyal? Completely. Helpful? Not even a little. But he has never once walked away.

Someday, someone on your team is going to describe you as either a mentor or a lesson. Take off the mask, keep your word, and spot them well.

Think of a boss who ended up in your mentor folder. What’s one thing they did that you still carry with you? I’d love to hear it. If you want to be the boss your team calls a mentor, let’s talk. And if this one landed, subscribe below so the next one finds you.

Original writing for Work, Considered., the Work, Advised. blog. Photo from Unsplash, credited above. Personal stories draw on Daniel's own experiences; no confidential workplace examples are used.