How to grow a team of leaders (Exit Five Newsletter)

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🌱 Growing Your Team Into Leaders: What’s Actually Working?

Editor's Note: Hi. It’s me. Dave again. Obviously. This week we’re talking about leadership. What’s funny is that the skills that help you grow your career (marketing) are often LESS important as you grow. Because management and marketing are two different skill sets. I’ve been managing teams for 10 years now. First as a manager, then a VP of Marketing, then CMO and now at Exit Five. And I’ll be honest…sometimes the people part is the hardest. I am a better marketer than people manager, but here’s a newsletter edition this week on management.

I keep coming back to this…

The real job of a leader isn’t only shipping one more campaign, it’s building a team of people who can make things happen without you needing to tell them every time.

The hard part is…marketing skill and management skill are two different games.

How are you doing this on your team right now?

What’s one system or ritual that actually levels people up?

How do you keep quality high without hovering?

So I asked the Exit Five community: what's actually working for them? Not theory. Not what you read in a leadership book. What are you doing right now that's leveling people up?

The responses were good. Really good. So I'm sharing some of my favorites in today’s newsletter.

👥 The Senior vs. Junior Split (And Why It Matters)

One of the best responses came from a Partner at a VC firm who's built multiple marketing teams. His approach is dead simple but most people miss it: you have to manage senior people differently than junior people.

For senior folks, your job is three things:

1. Give them context. Not just what needs to happen, but why.
2. Keep them aligned. Make sure they're not operating in a silo.
3. Be a thought partner. You're not telling them what to do. You're there when they need to talk through a problem.

And here's the part that surprised me: he doesn't even hold regular 1:1s with senior people. It happens as needed. Because if you've hired right, they know when they need you.

For junior people? Totally different game.

Your job is to model what good work looks like. That means two things most managers avoid: honest feedback and public recognition.

You have to show them what great looks like when you see it. Share it at all-hands. Post it in Slack. Make a big deal about it. Junior people are watching everything you do to figure out what matters.

❌ The Biggest Mistake Managers Make

Here's what kills me: managers who fix bad work themselves instead of having the uncomfortable conversation.

I've done this. You probably have too.

Someone turns in work that's not quite right. And instead of coaching them through it, you just...redo it yourself. Because it's faster. Because you don't want the awkward conversation.

But that's how you burn out. And that's how your junior people never level up.

The uncomfortable conversation IS the job.

🧑‍💻 The Forced Delegation Strategy

Here's one I didn't expect: one of the best ways to get your team to take ownership is to literally remove yourself from the equation.

One senior marketer had been at their company for 8 years. Everyone came to them for everything. They were a people pleaser who liked saying yes and had done all the jobs themselves on the way up.

So they took a 2-week vacation. Fully unplugged. Didn't bring the computer. Went abroad with the family.

And their company moves fast. So in those two weeks, a lot had to happen without them.

The team stepped up. People started going to the right team members for answers because they couldn't get them from the leader.

Here's the interesting part: when they came back, people kept going to those team members. The new pattern stuck.

It's kind of brilliant, right? You can tell people all day long to go to someone else. But sometimes you have to force it by not being available.

Obviously, don't just disappear without setting your team up for success. But if you're a bottleneck, sometimes the best thing you can do is get out of the way.

💬 Share Everything (Yes, Everything)

This one might be controversial, but I'm with the leaders who say: share everything with your team.

Strategy docs. Financial information. KPIs. All of it.

Not just with senior people. With everyone.

Why? Because if people understand why you're making decisions, they make better decisions themselves.

And make sure your people are actually in the room. Get them in the right meetings. Give them access. Say their name in front of other leaders. You can't grow leaders if they're not seeing how leadership actually works.

🤝 A Simple Training Framework That Actually Works

Someone shared a training framework that I immediately stole:

1. You watch me do the thing
2. We do the thing together
3. I watch you do the thing
4. You do it on your own

It's better for smaller, repeatable tasks with clear outcomes. But what I love about it is how clear it is.

No ambiguity. Everyone knows exactly what's happening and where they're headed.

👤 When Someone Stalls Out

What do you do when someone just isn't cutting it?

The consensus from the community: don't drag it out.

Sometimes a scope change works if that's an option. Give them a different role that plays to their strengths.

But most of the time? A fast exit is the answer.

Long PIPs rarely work. If someone doesn't get what good work looks like or isn't rising to the bar, trying to force it usually fails. It's hard. But it's better for everyone.

⚙️ Systems That Actually Work

Here are a few tactical things that are working for people right now:

Separate 1:1s for operations vs. development. One for running the business, one for skill building. Monthly works well for the development conversations.

Quarterly investment reviews. Bring marketing, sales, and product together to discuss what you're focused on and what you're NOT focused on. Then do the same with creative and content teams. Gives everyone context and a chance to lead.

Weekly idea sessions. 30 minutes where problems can come from anywhere. You don't solve everything, but you spin up teams to tackle things together.

❗️ The Most Important Thing

If I had to boil all of this down to one thing, it's this: hire people with a high quality bar.

If they have high standards but struggle to hit them, you can remove blockers and develop skills together.

But if someone doesn't have that internal bar? You'll spend all your time trying to convince them their work isn't good enough. That's exhausting and rarely works.

🙅 Not All Failures Are Created Equal

You need to give your team room to fail. But not all failures are the same.

Someone sponsored a conference for $80k. Perfect for their ICP. Top 100 architects. Nailed the booth and materials.

Zero leads. Not one callback.

But their GM said: "We learned this organization isn't where our ICP is. Now we can shift that spend to smaller, targeted events."

That's good failure. Channel experiments. Testing new approaches.

Bad failure? Poor communication. Budget mismanagement. Overspending because you weren't paying attention.

Your team needs to know the difference. Give them permission to try things that might not work. But be clear about what actual screw-ups look like.

And here's a tip: bring your failures to leadership more often than your wins. It builds trust.

🫵 What This Means for You

Building leaders isn't about having the perfect system or the right framework.

It's about being honest. Sharing context. Getting out of the way when you should. Stepping in when you need to.

And most importantly: having the uncomfortable conversations instead of doing the work yourself.

Your job isn't to be the best marketer on your team forever.

Your job is to build a team of people who can make things happen without you.

That's it. That's the whole game.

– Dave

P.S. What’s something you’re doing right now to help your team get better? Tell me what I missed here. One thing we are doing at Exit Five is (and this is not ground breaking) but I’m encouraging everyone to PICK UP THE PHONE. We need to talk more. Collab more. Not always sitting in front of a camera on a Zoom call. Pick up the phone, have a conversation, let’s riff on an idea and THEN we can have the meeting.

And what’s one thing you’d be pumped about as the next newsletter topic? Maybe we’ll pick yours ;)

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