If Your Team Can't Function When You're on Vacation, You're Not a Leader—You're a Bottleneck

Let me hit you with an uncomfortable truth:

If your business falls apart the second you're not watching, you haven't built a company. You've built a dependency.

I sat down with Adam O'Connor—Chief Commercial Officer at Gear Inc who's spent over a decade building and scaling international teams—and he absolutely destroyed the command-and-control leadership model that most of you are still clinging to like it's going to save you.

Spoiler: It won't. It's killing your growth, burning out your team, and making you the weakest link in your own organization.

Adam's philosophy? "We manage outcomes rather than people. My number one driver is to make each person who I work with the best possible version of themselves."

Not "hit these KPIs or you're fired."

Not "follow my exact process or we can't work together."

Not "let me stand over your shoulder and tell you exactly how to do your job."

Make each person the best possible version of themselves.

And if that sounds soft or touchy-feely to you, you're exactly the kind of leader who's about to get left behind.

The Micromanagement Tax You Didn't Know You Were Paying

Here's what micromanagement actually costs you:

Time. You're spending hours doing other people's jobs because you don't trust them to do it themselves.

Talent. Your best people leave because being treated like children is insulting and exhausting.

Speed. Every decision has to go through you, which means your company moves at the pace of your calendar.

Innovation. Nobody brings you new ideas because you've trained them that there's only one "right way"—yours.

Scalability. You can't grow beyond what you personally can oversee, which means you've built yourself a very expensive job, not a business.

Adam put it beautifully: "If I turn around and micromanage them, the pressure, the growth within that person isn't there anymore."

You're not developing talent. You're suffocating it.

And then you wonder why your scaling client success teams never actually scale, why your sustainable business expansion plans keep stalling, and why your retention (both employee AND client) looks like a horror show.

The English Accent Story That Explains Everything

Adam told this story that perfectly captures the difference between servant leadership and micromanagement:

He told a sales rep to "pitch it as if you're talking to the customer."

The sales rep—taking this literally because English isn't his first language—did the entire pitch in an English accent.

Adam's initial reaction? Frustration. "That's not what I meant!"

But then he caught himself.

He realized this wasn't the rep's failure. This was HIS failure to communicate clearly.

So instead of berating the guy, he sat down with him. Explained the principles. Walked through the key points. Role-played it again—this time with clarity instead of vague instructions.

The rep closed the deal.

More importantly? The rep learned something. Adam learned something. The relationship got stronger instead of more strained.

This is what servant leadership looks like. Not barking orders and getting pissed when people don't read your mind. But asking yourself: "What tools can I give this person to succeed? What else do they need from me?"

Most leaders would've written that rep off. Adam trained him up. That's the difference between building a team and cycling through bodies.

"A Rising Tide Floats All Boats" vs. "Every Man for Himself"

Adam's team operates on a simple principle: "A rising tide floats all boats. Everybody's helping everybody, and everybody celebrates everybody's wins."

Contrast this with most sales organizations where it's cutthroat competition, hoarding of knowledge, and celebrating when your teammate fails because it makes you look better.

Which culture do you think creates high-retention client relationships? Which one creates relationship-driven revenue growth?

Hint: It's not the one where everyone's sabotaging each other.

When you embed a culture where:

• Everyone helps everyone

• People can ask for help without shame

• Wins are celebrated collectively

• Knowledge is shared openly

• Team success matters more than individual glory

You get a team that actually functions like a team.

Revolutionary concept, I know.

But most of you are still running your organizations like it's a zero-sum game where one person's success means another's failure. And you're shocked—shocked—when your culture is toxic, your turnover is high, and your best people bail for companies that actually give a shaet about them.

The Two-Week Vacation Test

Adam dropped this line that should haunt every micromanaging leader:

"Any team that I build can run fully functional if I go on holiday for two weeks."

Can yours?

Seriously. If you disappeared for two weeks right now—phone off, email off, completely unreachable—would your business:

A) Continue operating smoothly because your team knows what to do and has the authority to do it

B) Descend into chaos because nobody can make a decision without you

If you answered B, congratulations. You're not a leader. You're a single point of failure.

You've built a company that's entirely dependent on you being the smartest person in every room, the final decision-maker on every choice, and the only one who can "do it right."

This isn't leadership. This is ego masquerading as competence.

And it's capping your growth at exactly the size you can personally micromanage. Which, let me guess, isn't nearly as big as you want to be.

Servant Leadership ≠ Being Soft

Let me address the objection I know some of you are screaming at your screen:

"But Adam, servant leadership sounds great in theory, but we need RESULTS! We can't just let people do whatever they want and hope it works out!"

You're missing the entire farcking point.

Servant leadership isn't about lowering standards. It's about empowering people to exceed them.

Adam's job is to bring in revenue. That's the outcome that matters.

But he achieves it by making his people the best version of themselves—by giving them the tools, the training, the autonomy, and the support they need to succeed.

Some people want to stay salespeople forever. That's fine. Adam helps them be the best salespeople they can be.

Some people want to grow into leadership. That's fine too. Adam mentors them and creates paths for advancement.

The outcome is the same: better performance. The approach is just more humane, more sustainable, and more effective than treating people like replaceable cogs.

The Global Team Advantage You're Ignoring

Adam's been building international teams for over a decade. Not because it's trendy. Not because it's cheap (though cost savings are a bonus).

Because it's better.

Better for customers who get 24/7 support without anyone working shaet hours.

Better for employees who get good jobs in their local economies with reasonable working hours.

Better for companies who can access talent anywhere instead of limiting themselves to one geographic region.

Better for growth because you're not constrained by local hiring markets or cost structures.

But here's what most companies get wrong about global teams:

They treat offshore workers like second-class citizens. Lower pay, worse treatment, less investment in development.

Adam's approach? "Allow them to become part of that company in the front line."

Not "those offshore people we hired to save money."

Not "the support team we'll never meet in person."

Part of the team. Period.

When you actually invest in global talent the same way you invest in local talent—same training, same opportunities, same respect—you build authentic client connections and trusted advisor relationships that transcend geography.

The AI Question Everyone's Getting Wrong

Adam brought up something critical about AI that most leaders are fumbling:

Some people love AI. Some people are terrified of it. Some people want to build elaborate workflows with it. Some people just want to ask ChatGPT basic questions.

And all of that is okay.

The leader's job isn't to mandate: "Everyone must use AI in exactly this way to hit these metrics."

The leader's job is to provide tools and let people use what works for them to achieve outcomes.

Some of Adam's team members create complex AI workflows for prospecting. Some prefer manual LinkedIn outreach. Some use AI for research and writing. Some avoid it entirely.

As long as they're hitting outcomes, it doesn't matter.

This is servant leadership in action: Providing resources, respecting different working styles, and focusing on results instead of process uniformity.

Most of you are doing the opposite. You're mandating tools, enforcing processes, and wondering why people aren't innovating or taking ownership.

You Should Be Learning From Your Team (But You're Not)

Adam said something that will make a lot of leaders uncomfortable:

"I learn every day from my team as well. People have different world experiences. People understand customers better than you."

When was the last time you genuinely learned something from someone you manage?

When was the last time you admitted you were wrong about something and a team member was right?

When was the last time you changed your approach based on feedback from the people actually doing the work?

If you can't answer these questions, you're not leading. You're performing leadership while learning nothing.

The best leaders treat it like a two-way street: teaching AND learning.

Your team is on the front lines. They're talking to customers daily. They're seeing patterns you miss. They're experiencing friction points you never encounter.

If you're not tapping into that knowledge—if you're not creating a culture where people feel safe sharing what they're seeing—you're flying blind while pretending you have perfect vision.

The Industrial Era Is Over (Stop Managing Like It's Not)

Adam nailed the problem: "Servant leadership versus being a task leader and a micromanager."

Task leadership is industrial-era thinking. You're on the factory floor, telling people exactly what to do, how to do it, when to do it.

That worked when the job was predictable, when the process was the same every time, when thinking wasn't required.

That's not the world we live in anymore.

Your team needs to solve novel problems daily. They need to adapt to changing customer needs. They need to innovate, experiment, and make judgment calls in real-time.

You can't micromanage that. You can only empower it.

Give people:

• Clear outcomes to achieve

• Tools and training to succeed

• Autonomy to figure out how

• Support when they need it

• Trust that they'll do the right thing

Then get out of their way and let them work.

This is how you build sustainable business expansion strategies instead of constantly hitting growth ceilings because you're the bottleneck.

The Culture You Embed at the Foundation

Adam emphasized this: "When you start building a team and setting the foundations of the culture, you want to embed that everybody feels like they're inputting and everybody feels like they contribute."

Culture isn't what you say in the company handbook or on the "values" poster in the break room.

Culture is what you reinforce every single day through your actions, decisions, and leadership style.

If you embed micromanagement from day one, that's your culture. Forever.

If you embed servant leadership—empowerment, trust, shared success—from the beginning, that becomes self-reinforcing.

Your best people stay. They mentor others. They model the behavior. New hires see it and adapt to it. The culture scales.

But you can't bolt this on later. You can't micromanage for five years and then suddenly decide "we're doing servant leadership now!" and expect it to work.

You have to build it from the foundation.

Watch the Damn Episode

This conversation with Adam went deep into building international teams, the practicalities of servant leadership, and why the command-and-control model is actively destroying your ability to scale.

If you're a leader who's exhausted from micromanaging, frustrated that your team isn't stepping up, or stuck at a growth ceiling you can't seem to break through—this episode is your blueprint for a different approach.

Watch the full episode here because Adam's frameworks for building high-performance teams and empowering people instead of controlling them are the difference between being a bottleneck and being a leader.

P.S. If your immediate reaction to "manage outcomes, not people" is "but how will I make sure they do it right?"—that's the problem.

You hired these people. Presumably because you thought they were capable.

Now you're treating them like they're incapable of making basic decisions without your oversight.

That's not management. That's a control problem dressed up as quality assurance.

And it's costing you everything: Speed. Innovation. Morale. Retention. Growth.

Adam's teams function without him for two weeks at a time. Can yours function without you for two days?

If not, the problem isn't your team. It's you.

P.P.S. That story about the sales rep doing an English accent? That wasn't a failure of the rep. That was a failure of communication from leadership.

How many "failures" in your organization are actually your failure to provide clear direction, proper training, or adequate support?

How many times have you blamed your team for not reading your mind instead of taking responsibility for unclear expectations?

Servant leadership means asking: "What tools can I give this person to succeed? What else do they need from me?"

Not: "Why can't they just do what I obviously meant even though I didn't say it clearly?"

Go watch the episode. Learn from Adam. And for god's sake, take a two-week vacation and see if your business survives without you. If it doesn't, you've got work to do.

Karl Pontau hosts The Human Connection Podcast, where we talk about the stuff that actually matters in business: the humans running it. Because whether you're B2B or B2C, it's really H2H—human to human. Subscribe so you don't miss the next episode where we probably say something that'll make your HR department uncomfortable.