What 20 Years in Sales Leadership Actually Teaches You

In Conversation with Jonathan Buckle, VP at Mitel

I've recently noticed something: the best advice from the smartest revenue leaders almost never makes it to LinkedIn. It happens in person, before a meeting, after a meeting, in the car to the airport. That guidance is honest and specific, maybe tough to hear but ultimately very powerful.

The problem is, you usually have to be in the room to get it.

I'm starting a series to change that. Conversations with revenue leaders I respect, customers and colleagues who've led large go-to-market organizations long enough to have real scars and real answers. I ask what I want to know. They tell me what they've actually learned.

I'm calling it In the Room.

Jonathan Buckle is a natural place to start. He's VP of Sales at Mitel, and he's been a customer of ours twice, which either says something good about us or something very patient about him. He trained as a lawyer, decided it was too boring, and got out. He moved from Europe to the US in 2014 and has spent close to two decades running large sales organizations. He also has a DJ background. More on that later.

He didn't hold back.

Jason: Thank you for being my first guest on In The Room! What do you love about your job? And what do you hate about it?

Jonathan: What I love is the variety. Every day is different. I trained as a lawyer and it was way too boring. I couldn't do it. In this role, no two days are the same. You're working with different people, different problems, different situations. That keeps you sharp.

What I hate is corporate PowerPoints. Let's just have a conversation! Use a good dashboard. Stop making people spend their lives building slides that nobody reads the day after the meeting.

Jason: You've spent a long time in complex sales organizations. What lesson took you the longest to learn?

Jonathan: Two things. Network and self-awareness. And they're connected.

Early in my career, I didn't really understand how important relationships were. I took some things for granted. Then I moved from the UK to the US in 2014, to the same company but in a completely different context, and suddenly I felt the difference. The people I had invested in over the previous four or five years, the ones I had stayed in touch with, made it easy to land. The ones I hadn't? Those were gaps that cost time.

The self-awareness piece came from a coach my VP got me when I first stepped into leadership. He ran me through psychometric testing, including an emotional intelligence assessment. My self-awareness score was, as I would call it, rubbish. It was a real moment. I was running through the motions, focused on tasks, not really tracking what was happening to the people around me. Self-awareness drives awareness of others. You can't lead well without both.

Jason: I had a similar moment later in my career. I was in a conversation explaining something that felt extremely obvious to me, practically Captain Obvious territory, and the people in the room said it was genuinely helpful. My team told me it kept them from making a pretty significant mistake. And I realized the thing I thought everyone knew was actually something I'd learned from 20 years of making mistakes. That's when I understood what experience is actually for.

Jason: What advice do you give someone stepping into their first big sales leadership role, about to have their first hard conversation?

Jonathan: Prepare for how the message will be received, not just for what you want to say.

Communication is not what you send. It's what lands. You can walk into a room with the right message and deliver it in a way that doesn't get heard. Or doesn't get acted on. Then you're having the same conversation three months later.

When you're new to leadership, you're used to telling yourself what to do. Or talking to peers who read things the same way you do. That changes when you're managing people. Everyone on your team processes information differently. You have to meet them where they are.

Jason: There are two conversations happening in every room. The one that's being said out loud, and the one going on in everybody's heads. A good leader tracks both. You're watching body language, hearing what gets said around the edges. That's where you find out whether your message actually landed.

Jason: Tell me about a call you made as a leader that you got wrong. What did you do when you realized it?

Jonathan: I've never made a bad call. [Laughs.] Okay, I make wrong calls all the time. Everyone does. The question is whether you recognize it fast enough to do something about it.

But here's what I've learned. Genuine collaboration, not the word on a slide but actual collaboration, where you bring people in with an open mind and you're seeking input, you get better decisions in the first place. That has reduced my failure rate significantly over the years. Different perspectives surface problems you would have missed. Sometimes consensus is hard to reach. But if you go in open, the outcome is usually better.

And when you get it wrong, you own it. Admitting you were wrong creates the conditions where people feel safe enough to tell you what they actually think. That's what prevents the next mistake.

Jason: That's the point most people miss. When you demonstrate you can be wrong, you're inviting the input that keeps you from being wrong. The answer doesn't have to be yours. It just has to be right.

Jason: "Caring about your team" gets said constantly. What does it actually look like in your week in a way most leaders miss?

Jonathan: I start with wanting good people. Good humans. That sounds simple, but most leaders don't actually think about it that way.

My job is to set my team up for success, because that's the math. If they succeed, I succeed. It's that straightforward.

I grew up hearing the golden rule. Treat people as you want to be treated. I threw that away. What replaced it is the platinum rule. Treat people as they want to be treated. That's harder. It requires you to pay attention to who someone actually is, what motivates them, how they process feedback. You can't apply the same approach to everyone on a team of 20.

And then there's the energy piece. We spend enormous amounts of time at work. I want the people on my team to go home at the end of the day and not be completely drained. Not bringing the weight of work home with them. In my view, work-life balance isn't really about hours or schedules. It's about your mental state when you walk out the door.

Jason: Has there been a point in your career where you almost walked away?

Jonathan: Yes. And I'll be honest about it.

I left a company I believed in. When I joined, I was fully bought in. The leaders, the direction, the mission. Over time, that changed. Not the end goal, but the path to get there. I stopped believing in the strategy. And you can't lead 200 people and fake it. You can't ask people to work hard and put themselves into something when you're not behind it. That's not leadership.

It took about three days to get through the final conversation. It was hard. But I left on good terms. I had to. Your network is your network. You don't know where paths cross again.

The harder part was thinking about the people I was leaving behind. You build a team. You hire good people. You develop them. And then you have to step back and ask, what am I leaving them with? That question stayed with me for weeks before I made the move.

Jason: How you exit says as much about who you are as anything else. There's a right way and a lot of wrong ways. And the fact that you were thinking about your team on the way out says something about the kind of leader you were while you were there.

Jason: What is something people who only know you at work would be surprised to learn?

Jonathan: I'm an open book, so most of my team already knows this. But for anyone who doesn't: I was a DJ in college.

I got through school by DJing. Vinyl records. House music, as it was just starting. It was the opposite of law school. It was everything law school wasn't. My marketing team somehow found out my college nickname and put it on a Christmas card. They've been trying to get me to DJ the Christmas party ever since. My fee is high and I'm not negotiating.

Jason: Last one. When the people who worked for you talk about you 10 years from now, what do you want them to say?

Jonathan: My team knows I never use the word "hope." Hope is not a strategy.

But here's what I'd want. Not that they remember the wins or the losses or the specific numbers. I want them to remember what the team felt like. The camaraderie. The culture of the group. And, if I'm lucky, that JB played some small part in helping them get to where they are.

That's what I think about when I think about legacy. Not the deals or the quarters. The people, and what they went on to do.

Jonathan is VP of Sales at Mitel and a two-time Backstory customer. We'll be continuing this series with other revenue leaders who have something real to say.

Connect with Jason Ambrose on LinkedIn.