How to Build a Leadership Team That Actually Works as a Team

Knowing how to build a leadership team is one of the most underrated skills in a CEO's toolkit. Hiring domain experts is the easy part. Getting those experts to function as a genuinely collaborative, high performing leadership team is where most companies struggle, and where the gap between a company that scales and one that stalls is often found.

When Executive Team Dysfunction Becomes the Norm

On the phone with a prospective coaching client recently, I could tell the CEO in front of me wanted to “get it all out”.

It was clear a lot was weighing on him and that he had not had a trusted ear in some time for the team complexities he had been carrying:

My VP of Marketing is mad at my VP of Sales. My VP of Product thinks we should fire both of them. My VP of Engineering regrets that we ever hired a VP of Product. In short, the whole thing feels like a mess. And we are going to run out of cash in 12 months if we don't get our shit together.

I wish I could say his confession regarding his team dynamic was the exception.

Unfortunately, it is the norm.

Another client I have worked with for years built a very close, high-function early team. That team of 20 people stuck together through many of the ups and downs of navigating product-market fit. They were close friends. The company had a delightful culture. However, even for this tightly-knit group, the challenges came.

When the company found serious traction and raised a massive Series A, the pressure came to hire ‘rockstar senior leaders.’ Some of that pressure came from the board, some was self-imposed by the founders. Much of the pressure came from a wonderful place: wanting the company to effectively scale and live up to its potential.

But it quickly became clear a critical piece was missing.

We were signing up world-class leaders. Each individual was a domain expert in her or his respective role. But as the CEO and I unpacked the emerging team dynamic, two things became clear:

1. We were not hiring for aptitude in a team-setting
2. We were not setting an expectation that these executives were expected to work as a part of the leadership team ahead of their responsibilities in their individual roles

What High Performing Leadership Teams Actually Require

For a company to effectively navigate the perils of shifting from product-market-fit to scale, and later to innovate its way through stalls in growth, the leadership team must work as a team.

The product organization will fail to capture opportunities in the market if they are not hearing from sales and marketing what is being learned from prospective customers.

Engineering will fail to effectively weigh tradeoffs in tech debt if they do not have a grounded picture of the financial realities of the business.

To build a high performing leadership team, a CEO must create five conditions. Here is a summary, with detail on each below:

How to Build a Leadership Team: Five Foundations

1. An Invitation to Be a Team

I often suggest to clients they invite their leadership teams to hang their ‘domain’ hats at the door. What I mean by that is when we enter into the leadership meeting (or the quarterly planning meeting, etc.) we are here as an entrepreneurial team not as separate department heads.

We are here to build the business together.

We are not here as a startup congress, each representing our own department's interests.

Check your lanes and your egos at the door.

2. Clarity on Team-Level vs. Domain-Level Accountability

I am a big fan of writing down accountabilities.

There are certain accountabilities that are a part of the role of each leader; there are other accountabilities that are part of being on the leadership team.

A simple example:

• As VP of Sales: hire and train sales reps, hit revenue targets, manage the pipeline
• As a member of the leadership team: contribute to company culture, co-own cross-functional decisions, share market intelligence with product and engineering

Both sets of accountabilities should be written down, shared, and revisited regularly. You can read more about how to structure this kind of clarity in the context of one-on-one meetings and individual accountability.

3. Trust of One Another

Many of the CEOs I meet call their executive or leadership team a “team” but do not treat it as a team.

One way I like to explore this in a session is to ask the CEO to identify the best team that she or he has ever been a part of. Often, this will be a sports team, an academic team, or a team from a previous work experience.

I might ask the CEO to name the characteristics of this team. What made the team great?

Next, I will ask that she grade her current team against each of these characteristics. Some interesting insights tend to emerge.

One element that often jumps to the forefront is trust. To operate as a team, these individuals must trust one another.

To negate seemingly squishy elements of team-building such as emotional closeness, effective conflict-resolution, knowledge of one another’s backgrounds, etc., is to negate trust and short-circuit efficacy.

If executive team dysfunction is the presenting problem, trust is almost always the root cause. Addressing the symptoms without addressing trust rarely holds.

4. An Education in Company Building

To effectively innovate, problem-solve, and scale, we want this team to work as a team. We want them thinking beyond their role. We want them thinking as entrepreneurs and company-builders.

Many good leaders have the potential to be great. Often, what is missing, is an understanding of how to build a company.

Many CEOs I meet feel alone in their role in part because their leadership team does not share their full context of the task at hand. Often, in these cases, the only person with full context of the challenges at hand is the CEO herself.

We can change that by coaching the leaders on a fuller understanding of how to build a business; we can invite them in.

5. Full Context and Transparency

Part of inviting leaders in is providing context.

In my early years as a CEO, I thought I had to keep many details of the business close to my chest. I was reticent to give the team, or even the leadership team, access to financials, board decks, etc. As a result, I created a sense of aloneness in my role that caused me a lot of pain. I also left my leaders unable to really be the partners I desired.

To move from domain leads to company-builders, we must provide our leadership team with full context. Share the financials, and teach your team how to understand them. Share board feedback, and teach your team how boards functions and how investors think.

Invite and facilitate context.

This kind of radical transparency is one of the clearest paths from CEO loneliness to genuine leadership partnership. You can read more about that dynamic at how to build and lead high-performing leadership teams.

The Opportunity in Front of You

It is heartbreaking how many founders and CEOs feel deeply alone in their roles when the solution is often right in front of them.

There is an opportunity for every CEO to move from aloneness to connection and partnership.

If you have a leadership team, and if that team is not yet working together as a high-trust, high-efficacy group, that is a solvable problem.

If you would like some help thinking through how to get from where you are to where you want to be, reach out here.

Wishing you connection, ease, and a team that has your back.

-Matt

Frequently Asked Questions

How do you build a high performing leadership team?

Building a high performing leadership team requires more than hiring strong individual contributors. It means creating five conditions: a shared identity as a team rather than a collection of domain heads, explicit team-level accountabilities alongside functional ones, genuine trust built through time and honest conversation, a shared education in how to build a company, and full transparency on financials, board dynamics, and market realities. Most leadership team dysfunction stems from the absence of one or more of these conditions.

What causes executive team dysfunction?

Executive team dysfunction most commonly stems from a lack of trust, unclear accountability structures, or an absence of shared context. When VPs optimize exclusively for their own function rather than for the whole company, conflict and siloing follow. This is often less a hiring problem than a structural and cultural one. The team was never explicitly invited to be a team, so they default to competing for resources and credit instead of collaborating.

How do you align a leadership team around shared goals?

Alignment starts with shared context. When every leader understands the financials, the board's perspective, the competitive landscape, and the company's key risks, they are much better positioned to prioritize collaboratively. A quarterly OKR process where the leadership team collectively sets 2 to 3 company-level objectives, rather than negotiating departmental wish lists, is one of the most effective alignment mechanisms available to a CEO.

What is leadership team accountability and why does it matter?

Leadership team accountability refers to the explicit responsibilities each executive holds as a member of the leadership team, distinct from their functional role. A VP of Engineering who is also accountable for company culture, for example, will behave very differently in a leadership meeting than one who sees their only job as shipping software. Writing down team-level accountabilities and reviewing them regularly is one of the simplest and highest-leverage changes a CEO can make.