The Executive Team Trap: Why Size Could Be Your Biggest Problem

Simple Question: How Big is Your Executive Team?

Five people? Eight? Twelve? Here’s the thing—size matters. The bigger your team, the less effective it’s likely to be. The sweet spot? Around five. Big enough to bring diverse skills to the table, but small enough to actually get things done without endless debates.

Just this week, I spoke with a CEO prospect who hit me with a classic: “I need your help, Dom. My Executive Team has ballooned to twelve people.” No shocker there—it’s a story I’ve heard a dozen times. But here’s the hard truth: if your team has exciting plans for growth, that oversized squad will slow you down. Worse, it’ll frustrate your top performers.

The solution? Act now. Trim it down before it derails your momentum.

How Did You End Up Here?

Let’s face it—this isn’t exactly rare. Companies hit inflexion points as they grow, and things get messy. When you’re at around 30 employees, you start to see an “Executive Team” take shape. It’s not a formal C-suite yet—more like the HR person, the marketing lead, and maybe a few others who report directly to you, the CEO.

Then comes the 100-employee mark, and guess what? That management team gets bigger, too. The original crew might still be around, joined by a few new hires on big salaries. Now you’ve got a bloated team that feels more like a patchwork quilt than a well-oiled machine.

By the time we meet clients in the 100-to-300 staff range, it’s the same story: 12+ people on their Executive Teams. Every function head is sitting at the table. But here’s the rub—they’re often a mismatched bunch. The skills don’t align, and decision-making? It’s like wading through treacle. Slow, sticky, and frustrating.

Sound familiar? It’s time to rethink how you got here—and how to fix it.

Leadership by Committee: The Slow Death of Progress

When your Executive Team grows beyond 12 people, it stops being a leadership team and starts looking like the United Nations—or worse, your local council. It’s leadership by committee. Everyone gets their “turn,” but by the time the mic makes it to you, there’s no room to question or dive deeper. You just say your bit, and the cycle of surface-level advocacy rolls on.

This dynamic plays out all the time in the teams we coach. Strategy sessions turn into a parade of opinions, each more general than the last. The conversation broadens to the point of absurdity—everyone feels the need to chime in, but no one goes deep. You never hear, “Why do you think that?” or “Can you elaborate on this idea?” There’s no space for real inquiry.

Instead, meetings become a PowerPoint marathon. Twenty-minute presentations, followed by three or four hours of slow, soul-crushing drudgery. The room is half-asleep, and the team’s progress is at a standstill. Worse, this becomes normal. A habit. And breaking out of it feels impossible.

If this sounds familiar, it’s not just frustrating—it’s a red flag. It’s time to shake up the status quo before your team’s momentum grinds to a halt.

Cutting the Clutter: Fewer Direct Reports, More Impact

Here’s a game-changer: reduce the number of leaders reporting directly to you as CEO. Sounds obvious, right? But it’s not always easy, especially once you’ve hit the 100-employee mark. That’s when it’s time to start splitting senior managers into two distinct groups: an Executive Team and an Extended Leadership Team.

Why these terms? Because they reinforce the idea that everyone’s a leader. There’s no “elite club” or “second class.” It’s just about creating a core team that drives strategy and a broader team to execute on it.

Here’s how to make it happen: ask your current senior team to collaborate on a future org chart. Frame it in the context of growth—“We’re planning to grow 20% annually, which means doubling the business in three years. What’s our leadership structure going to look like when we get there?”

This conversation should be about roles, not people. Everyone in the room will naturally assume they’ll be on the Executive Team, but steer the focus toward structure. Ask, “How many people do we really need at the top table to stay effective? How do we group functions? Should Finance, HR, and Ops sit together? Do we need a Chief Revenue Officer to consolidate Marketing and Sales?”

The key is to keep it strategic, not personal. Gradually work toward this model, giving people time to adapt. The result? A leaner, more focused Executive Team that can actually make decisions—and the space for everyone else to shine in the roles that suit them best.

Who Should Really Be Doing Strategy? Spoiler: It’s Not Always the Executive Team

Let’s be real—most organisations struggle to manage strategy meetings properly. Either they’re not happening, or they’re filled with the wrong people.

First, let’s talk about who should be in these meetings. Just because someone is on your Executive Team doesn’t mean they’re cut out for strategy. And that’s okay! Some leaders are brilliant executors, which is just as valuable. To figure this out, we often use Patrick Lencioni’s ‘Working Genius’ framework with our clients. People who excel at strategy typically score high in “Wonder,” “Invention,” and “Discernment.” Not everyone will have that mix—and they shouldn’t have to.

If you’re trying to hash out strategy with a dozen people in the room, guess what happens? The planners get bogged down in details, while the big-picture thinkers silently fume (or check out entirely). It’s a recipe for stagnation, not innovation.

Here’s a better approach: create a separate strategy group. Pull in the people—whether from the Executive Team or the Extended Leadership Team—who genuinely thrive at strategic thinking. Limit it to four or five people, plus the CEO. Then, meet regularly, maybe monthly or biweekly. No rigid agenda, no PowerPoint decks. Just a space to think about the future and have exploratory conversations.

Not sure how to choose the group without stepping on toes? Flip the question to your team: “Who do you trust to handle strategy on behalf of all of us?” Limit their picks to 4–5 people. They’ll almost always land on the right mix, and you won’t have to make the call yourself.

Once your strategy group has defined the direction, hand it off to the larger team to build the road map and execute. That way, everyone gets to play to their strengths—and your business avoids the paralysis that comes from trying to do everything with one giant, unwieldy team.

DNA Transfer: Keeping Your Culture Intact as You Scale

When your Executive Team (ET) is small, people management naturally shifts to the Extended Leadership Team (XLT). That’s great in theory—but only if you’re deliberate about keeping everyone aligned. This is where many companies drop the ball.

One solution? A quarterly off-site between the ET and the XLT. Just one day every few months to work through the big stuff together. It’s not just about strategy or updates—it’s about transferring your company’s DNA. Your values, behaviours, and cultural norms need to flow consistently through the entire leadership structure. Without that, you’ll end up with a culture that evolves by accident—and probably not in the direction you’d hoped.

This is especially critical when you’re in growth mode. We’re talking 30% to 100% annual growth rates. At that pace, things can go sideways fast. Values and behaviours start slipping, and suddenly, you’re not the company you set out to build.

A quarterly off-site acts as a reset button. It keeps everyone—from the top execs to the broader leadership team—aligned on the kind of culture you want to scale. Don’t leave this to chance. The culture you get will always reflect the consistency—or inconsistency—of your leadership. Make sure it’s deliberate.

Facing Difficult Conversations with Your Executive Team: Grasp the Nettle

Let’s cut to the chase: avoiding hard conversations with your Executive Team is the fastest way to create a culture of dysfunction. When you tiptoe around egos, you’re not just delaying the inevitable—you’re setting the tone for the entire organisation. Before long, everyone knows the org chart is broken, but nobody’s fixing it. That’s the kind of culture that stalls growth and derails objectives.

As CEOs expand their larger teams, the stakes only get higher. Each new member brings priorities they’re desperate to push forward, and without strong leadership, those competing agendas can turn into visible conflict. And here’s the kicker: if your Executive Team isn’t collaborating, don’t expect the rest of the company to work well across functions either. Dysfunction at the top always trickles down.

This is why you can’t afford to dodge these conversations. The way your Executive Team operates defines your culture. Are you building a culture of accountability, clarity, and collaboration? Or are you unintentionally creating one of avoidance and siloed thinking?

Grasp the nettle. Fix the org chart. Have the tough conversations—quickly, directly, and with the bigger picture in mind. Leadership starts at the top, and it’s your responsibility to set the standard.

Written by business coach and CEO mentor Dominic Monkhouse. Read his new book, Mind Your F**king Business here.