On Leadership Teams

A Guide for Creating Healthy, Effective Executive Leadership Teams



This guide pulls together my experiences, learnings from companies I've worked with, and the best thinkers that I could find. Much of the inspiration behind this guide began with reading Patrick Lencioni's thoughts on teams and then adding/refining from there (his books are in the suggested reading below). It's a living document so please send feedback and suggestions.

I hope it's helpful for you in building a healthy and effective executive leadership team.

Why Building a Healthy Leadership Team is Vital

Your leadership team sets the standard for how your company organizes around challenges and opportunities. It’s perhaps one of the highest leverage areas in startup, but too often ignored.

Let’s put an end to that, shall we?

Here’s the truth: A high-functioning leadership teams foster a high-functioning organization. A dysfunctional leadership team fosters dysfunction. Unfortunately there’s not a lot of middle ground between the two.

If you care about building a healthy organization the work starts within the leadership team.


So Who Should Be in the Room?

One of the biggest causes of problems on a leadership team is there’s just too many voices in the room.

When people fear they may only have a few chances to speak they’ll use those moments to advocate for their position. It’s critical that leadership teams explore and ask questions together to develop mutual understanding.

The more people in the room, the less understanding you get.

Patrick Lencioni in his excellent book The Advantage emphasizes this point and make a recommendation, saying "many teams I’ve encountered struggle simply because they’re too large…a leadership team should be somewhere between three and twelve people, though anything over eight or nine is usually problematic."

I sense Lencioni’s advice leans later stage. From my own experience, when our leadership team was eight it felt too large. Scaling back to five and the conversation instantly became richer and frankly, easier.

It’s the CEO’s job to decide who should be in the room - they need to be decisive in choosing and optimize for the team as a whole, not individual egos.

Diane Coutu, author of Senior Leadership Teams, captures the importance of this when she writes: ”Often the CEO is responsible for the fuzziness of team boundaries. Fearful of seeming exclusionary—or, on the other end of the spectrum, determined to put people on the team for purely political reasons—the chief executive frequently creates a dysfunctional team. In truth, putting together a team involves some ruthless decisions about membership; not everyone who wants to be on the team should be included, and some individuals should be forced off."

Within a leadership team the key functions of the business must be given voice. That does not mean that every department head needs to be included. Some situations may require one person to represent more than one key area and some functions may not be core to the business’ success. So make a best guess, leaning toward smaller. It’s easier to add a missing voice once you notice it than to remove someone who never should have been involved in the first place.

In brief: For leadership teams…smaller is better, some tough choices might need to be made, and the necessary voices need to be in the room.


Trust - The Foundation for Effective Leadership

Once the team is known, building trust becomes the foundation on which a health team executes.

With trust building the leader must always go first (figuratively and metaphorically). In leadership teams, the standard for vulnerability needs to be set and maintained by the CEO.

To build trust, people need to experience a repetition acceptance to their vulnerability. Put plainly, when an individual chooses to be vulnerable, afterwords they need affirmation that they are still accepted by the group.

While building trust takes time, but there are a few practices for creating momentum:

  • The Five Dysfunctions of Team offers a simple trust building practice called the Personal Histories Exercise. Here’s how you do it: Gather the team around a table (I think a dinner out can be a great time for this) and have each member answer three questions:
    • Where were you born and where did you grow up?
    • How many siblings do you have and in what order do you fall?
    • What was the hardest challenge that you faced growing up?
  • Creating and sharing owner’s manuals can also help develop understand and trust between leaders. For this, each member spends some time answering a handful of questions about what it’s like to be them and how they work best (link to resource coming soon). Once completed, the team gathers in a circle and each person takes 10 minutes to share about their owner’s manual followed by each other team member sharing either: one thing they learned or one thing they want to commit to doing in support of that person.

Fostering Healthy Conflict

”When there is trust, conflict becomes nothing but the pursuit of truth, an attempt to find the best possible answer.” - Patrick Lencioni

From a young age we’re taught that conflict is bad, making us and others feel emotions so strongly that we might be ostracized from the group. A sense of belonging being a basic human need we choose instead to swallow down our opinion in the name of safety.

Within leadership teams, our fear of conflict leaves dissenting opinions unvoiced, individuals feeling unheard, and the company unhealthier.

Fred Kofman does well at capturing how this unfolds within organizations:

”Many of us settle for pseudo-harmony rather than face the hard work of creating the real thing. The desire to keep the (semblance of) peace often leads us to avoid conflict, sweeping our differences under the carpet. Unaddressed, these disagreements turn into contempt, resentment, and mistrust.”

So what’s the alternative?

Teams that trust each other, knowing one another’s motives are good, can begin exploring healthy conflict together.

Doing so should be made explicit within the leadership team. It’s also worth noting that healthy conflict is in many ways a re-learning how we interact with one another. There are likely to be some tricky spots and the team should talk through those openly. Remember, the goal is to bring more information out into the open.

Here are a few practices to foster healthy conflict:

  • Start with everyone practicing listening more. Kim Scott’s wonderful Radical Candor model is all about fusing caring for people and being willing to also challenge them directly. If everyone is just waiting their turn to talk, then there’s little room for understanding or caring about other’s opinions. Instead part of the CEO’s role in meetings is to “give the quiet ones a voice” which might mean interrupting those sharing too much and prompting others to chime in.
  • Similarly, in meetings where you suspect a disagreement “gently demand that people come clean”1 This isn’t stirring the pot, its actually preventative from the disagreement lurking in the background and undermining other efforts.

Healthy conflict works wonders in an organization. More and better ideas are surfaced. Morale is actually boosted as everyone knows more that things aren’t being left unsaid and most importantly it creates a richer foundation on which to move into commitment on next actions.


Commitment, Not Consensus

I speak with far too many teams who rely on consensus decision making. They justify their approach as a way of building a sense of togetherness and harmony. But really it’s another form of conflict avoidance.

There can actually be more togetherness and harmony through healthy debate (and conflict). The key is that the debate must be followed by commitment.

Here’s why...

Consensus asks everyone to reach the same conclusion. With highly-intelligent people this isn’t always possible. In the worst case, you reach a ‘false consensus’ where individuals grow exhausted of the debate and choose to "agree” while actually disagreeing. This pattern runs the risk of team members remaining unengaged and secretly hoping the decision is proven wrong to justify their opinion.

You either build a team of “yes” people who don’t actually commit to “yes” or you build a team of tenacious leaders willing to engage in healthy debate and commit to the chosen plan.

To make commitment easier, use “Disagree & Commit” to conclude meetings. This simple framework is best described by Tom Tunguz (http://tomtunguz.com/disagree-and-commit/)

Disagree and commit is a management technique for handling conflict. There are two parts to it. First, expecting and demanding teammates to voice their disagreement. Second, no matter their point of view, once a decision has been made, everyone commits to its success.

In this model it will often fall on the CEO to make the final decision.

Then before leaving the room, everyone should look the team in the eye and verbally commit to the decision. There should be no doubt that you’re moving forward together.

To help nurture learning to commit, Fred Kofman in Conscious Business offers a series of questions leaders should ask and acceptable commitment responses.

Before committing to a decision, a leader should ask themselves these four questions:

  • Do I understand what is being asked of me?
  • Do I have the skills and resources to do this?
  • Am I convinced that those that I depend on will deliver?
  • Am I wiling to be held accountable for this?

When asked to commit, these are the acceptable responses:

  • Yes, I promise
  • I commit conditionally; if X happens then I commit. Would that work for you?
  • I need more information or clarification externally, but will respond by Y (a definite date).
  • I need more information or clarification now. (this will require more discussion)
  • No, I do not commit. (this will require more discussion)
  • I have a counteroffer. (this will require more discussion)

Accountability as an Operating System

With trust, healthy conflict, and a framework of commitment in place, a team can then move toward generating meaningful and sustainable results. Doing so begins with establishing accountability as a way of working.

Leadership teams are usually composed of functional leaders who also lead teams of their own. A chief marketing officer cannot care more about the company’s marketing than the company’s leadership. A dysfunctional leadership team won’t be overcome by even the greatest marketing execution of all time. The leadership team is everyone’s primary team.

Teams that trust one another, embrace healthy conflict, and commit are also willing to hold each other accountable. Importantly, this is done not to shame them but to bring out the very best in each other and the collective.

In the absence of real accountability there’s a “floating” that happens. Milestones are missed. Conversations on why don’t occur. And the entire organization will notice the standard (or lack of a standard) that has been set. Leadership teams with accountability woven into the way they work cascade effectiveness throughout the organization.

Practices to foster accountability:

  • Public sharing of objectives that are specific, measurable, and time-bound. A leadership team should be accountable at least to each other and ideally also to the people they lead. I’ve seen some masterful execution occur once objectives were published publicly. Not only did a light a fire under the entire team, but it also created more dynamic conversation around what matters.
  • Incentives throughout the leadership team should be aligned with overall team progress. Too often I see a sales leader’s compensation tied primarily to sales; a product leader’s comp tied to product performance. It cannot be understated how much this creates misalignment in a leadership team. If top-line revenue is a key metric then incentivize the entire team on that, and whatever other key metrics there are.

Symptoms of Problems in a Leadership Team

These are a few clear signs to watch out for. Things that signal something may be off within the leadership team:

  • Meeting too often.
  • The team is stuck in a reactionary mode. There’s always a new fire to be put out and little time for building toward the future.
  • Personal attacks - both in-person and behind people’s back are a problem. For ambitious organizations, there should be zero tolerance for allowing this pattern to continue. Surface the issue, get to the root cause, and recommit to one another. When that’s not possible, the team may need to change - either removing one or more members from the leadership team or letting a problematic employee go.
  • The company as a whole is underperforming - This is usually either a leadership or cultural issue (often both).

Want Help Improving Your Leadership Team?

If you're committed to leveling up your leadership team, we should talk. Often a short 30-minute conversation is often enough to help you see a new path forward.


Sources & Further Reading

  1. From The Advantage by Patrick Lencioni