Executive Team Coaching: When Individual Coaching Isn’t Enough

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Your executive team isn’t working the way it should.

You know it. They know it. Now you’re trying to figure out what to do about it. That’s probably why you’re reading this. Smart move.

The question most leaders ask at this point goes something like: “Should I get executive team coaching for the whole group, or should I just get individual coaching for the one or two people I think are the problem?”

It’s a reasonable question. It’s also the wrong question.

Because executive team coaching and individual coaching aren’t mutually exclusive options. In fact, they each solve different problems. Understanding the difference between them is the important step to helping you figure out what your team needs.

So that’s what we’re going to do now. Why? Because I want to help.

The Mistake: Thinking It’s One or the Other

The assumption I hear from a lot of leaders is the belief that if you just fix the individuals who are causing problems, the team will automatically get better.

Sometimes that’s true. But not always.

If you genuinely have one person who’s completely out-of-step with everyone else, individual coaching for that person (instead of executive team coaching) might be the right thing to do.

However, most of the time, that’s not what I see happening.

What may look like a problem with one or two individuals is actually a team dynamics problem in disguise. For instance, that conflict that exists between your CRO and your CTO isn’t really about those two people – it’s about the environment the team has built together. It’s most likely based on unclear decision systems, and unspoken tension that everyone turns their back on when it appears in the room.

You can coach those two individuals all you want – I guarantee that the dynamic will still be there when they’re back in a room together.

That’s the gap executive team coaching fills. And that’s why it’s a fundamentally different than coaching individuals.

What Executive Team Coaching Actually Focuses On

Individual coaching focuses on the person – their patterns, their blind spots, the behaviors they’ve developed that are limiting them and their team.

Executive team coaching focuses on the space between the people. It focuses on the dynamics between the team members and the patterns they’ve collectively reinforced by their behavior. Every executive team has created an identity that that they’ve built together – consciously or not. That identity may or may not be working in the favor of the team.

With executive team coaching, we start by understanding the environment the team has created. This means exploring the communication dynamics, the behaviors that are accepted and those that aren’t, and the patterns that keep showing up no matter who is in the room.

From there, we can look at what’s creating and sustaining that environment – whether that’s processes, decision-making structures, communication patterns, or the dynamics between specific individuals. Sometimes the fix starts with structure. Sometimes it starts with behavior. It all depends on your team’s specific dynamic.

What team coaching is not focused on, as it’s primary purpose, is individual identity. Individual work happens in 1:1 coaching sessions. with leadership team coaching, we’re working on group identity – how the team acts together, how they see themselves as a unit, and whether that collective concept is beneficial or limiting to the team (and the company’s) growth.

Signs You’re Dealing with a Team Problem, Not an Individual Problem

Before you decide whether or not executive team coaching can benefit your group, let’s talk a bit about the problems you’re having and if they are best addressed by team or individual coaching solutions. Sound good?  Great. Here’s how to tell.

The problems follow the team, not the individuals. If a specific person moves away from the team and the team problems move with them, that’s an individual issue. However, if the same friction keeps happening with different people and in different team configurations, that’s a team dynamics issue. Executive team coaching is the answer.

People act differently together than they do separately. If you’ve seen each of your leaders perform well when they are leading their own teams, but something feels wrong when they’re all in the room together – that’s not a coincidence. That is a big red flag that the group dynamic is creating a challenging environment that nobody is consciously creating on their own. In fact, Google’s research on team effectiveness found that who is on a team matters far less than how the team works together – and that dynamic is exactly what executive team coaching is designed to address.

The same conversations happen over and over. When you keep talking about the same tension, realigning on the same priorities, or having the same “we need better collaboration” conversation over and over, but nothing sticks – that’s bad.  It sounds like you’re treating symptoms, not the actual problem. Executive team coaching will reveal what’s underneath – and help fix it.

Individual coaching hasn’t moved the needle on team performance. You may have already invested in coaching for one or more of your executives. Hopefully they’ve gotten better individually – but you notice that the team dynamic hasn’t changed. It’s still bad. This is a pretty loud alarm that individual coaching isn’t enough.  Executive team coaching is the next step.

Why the Best Answer Is Usually Both

Here’s what I’ve seen work best: executive team coaching as the primary intervention, with individual coaching running alongside it for the leaders who need it.

Not either/or, but both – doing different jobs at the same time.

Team coaching works with the group. It addresses the shared environment, the collective patterns, the dynamics between the individuals. It’s the work that changes what happens when everyone’s in the room together.

Individual coaching works on the person. It focuses on their self-awareness, the specific behaviors they’re bringing to the team environment, the patterns that might be contributing to the group dynamic in ways they probably can’t even see on their own.

These two tracks support each other. The individual work helps each leader show up differently in the team sessions – more self-aware, and more able to see how their behavior impacts the team dynamic. The team work creates the context where that individual growth actually gets applied with the actual people it needs to work with.

Without the executive team coaching, individual coaching has it’s limits in the leadership team dynamic. Sure, it will improve the individual’s leadership behavior, but it won’t necessarily address how the entire team interacts. Similarly, without the individual work, team coaching maybe bring about issues that not everybody has the self-awareness to address.

Together, team coaching and individual coaching create a powerful solution that neither one can produce alone.

So When Does Individual Coaching Make Sense on Its Own?

There are situations where individual coaching is the right first move – or, sometimes, the only move you need.

If you have a leader who’s new to the team or new to their role, individual coaching can turn them into a productive executive team member faster than they can on their own.  In that case, the team dynamic isn’t the issue yet – they just need to get up to speed faster and with fewer costly mistakes.

If you have a leader who’s genuinely struggling with skills or behaviors that are specific to them and their subordinates (not a team dynamic, but something about how they operate individually), individual coaching is the best tactic for supporting them.

And if your team is actually functioning well and you’re investing in development for your strongest performers, individual coaching is the way to go. Most companies just get coaching for their lower performers, but high performers get a lot of benefit from coaching – expecially since they’re usually self-aware enough to use it and motivated enough to do the work.

But if the problem is how your team operates together – the dynamics, the communication breakdowns, the frustrating patterns that show up every time you’re all in a room – individual coaching alone won’t solve that challenge. You need to work on the system, not just the parts.

What This Actually Looks Like in Practice

Executive team coaching engagements typically start with a diagnosis phase. In this phase we have individual conversations with each leader to understand what’s actually happening on the team, from each of their perspectives. What each person says privately, compared to how the group acts collectively, is usually where the most useful and important information is derived.

From there, the coaching happens in the real work. Not in a workshop or an offsite exercise – we help with actual meetings, where actual decisions need to be made, and actual tension shows it’s ugly face. Because your executive team’s patterns aren’t going to show up in a laboratory – they show up when you’re in the environment that is causing the struggle.

At the same time, individual coaching sessions will happen for the leaders who need them. Sometimes that’s everyone on the team, but usually it’s not. Most times it’s a few people with specific leadership development needs.

Keep in mind, individual coaching isn’t a prerequisite to team coaching – it’s a complement to it.

Teams are complex systems. Changing how they operate takes weeks or months of consistent work, not a single meeting and – poof! – everything is solved.  The teams that get the most out of the process are the ones that are committed to change and are willing to be purposeful in making it happen.

If you want to talk through what’s happening on your team – and whether executive team coaching, individual coaching, or some combination of both makes the most sense for your situation – let’s have a conversation. I’ll give you my honest opinion either way.

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Jeff Matlow is a leadership coach and 3x entrepreneur who helps senior leaders spot the unconscious patterns keeping their teams dependent on them – then redesign the environment so everyone can actually perform. He’s spent 25+ years working with leaders at Disney, Porsche, Nestlé, and hundreds of high-growth companies. Think Ted Lasso meets Brené Brown meets a Navy SEAL. Learn more about working with Jeff or subscribe to The Best Leadership Newsletter Ever.