Executive Team Performance: What Your Team Doesn’t Know About Each Other Is the Key to Strategy That Actually Works
The planning session went well. You could tell by the energy in the room – the conversation was lively, people engaged with the frameworks, and by the end of the day, you had something that looked like alignment, at least on the whiteboard. Your senior leaders left the retreat with clear priorities, a shared understanding of the direction, and action items with names attached.
Two weeks later, you’re watching the same old patterns reassert themselves, and you can’t quite put your finger on why. I have seen what emerges in that gap over and over again. The planning session was successful, but what it produced was neither leadership alignment nor strategy.
What Strategy Asks of a Team
Most of what leaders do to prepare for strategic planning is process-focused: the facilitation model, the data inputs, the goal-setting framework, the presentation templates. All of that matters, but the most important preparation for a strategy session has nothing to do with process. It has everything to do with connecting the people who will build the plan to each other.
Strategic planning, done well, asks a team to do several things that require genuine trust to pull off. It asks them to tell the truth about where the organization is, including each of their functions. Not the public version. Not the version that makes everyone look good. The real picture. It asks them to disagree productively about where to go next, to surface competing priorities without it becoming political, and to commit to a direction that not everyone would have chosen on their own. And then it asks them to hold each other accountable for what they said they’d do.
None of that is possible without real connection within the team, and recognition of the unique talents each of them brings to the table. And most leadership teams walk into a planning session without it. I have worked with teams that had been together for years yet had a shockingly low understanding of how their colleagues actually operated underneath the surface interactions. This work consistently unearths a new level of respect and candor that replaces misunderstanding and relationship blocks.
When It Looks Like Alignment but It’s Not
A 2023 Harvard Business Review analysis of more than 500 people – from frontline staff to executives – found that actual strategic alignment runs two to three times lower than what those same people believe it to be. They think everyone is on the same page; in reality, different people hold widely different understandings of the strategy.
That gap doesn’t come from carelessness or ill intent. It comes from what happens when the relational foundation isn’t strong enough to support honest conversation. People fill the ambiguity with their own assumptions. They hear the direction through the filter of their own functional priorities. They nod because challenging the direction would require a kind of honesty the team hasn’t built the trust to support.
The result is a strategy that looked agreed upon in the room but starts fracturing before the ink dries and execution even gets off the ground.
Designing Strategy from a Position of Strength
The way I approach strategic planning asks organizations to examine their purpose, growth, and evolution as interconnected realities – not just as boxes to check in a planning document. Those three dimensions are meant to be held in dynamic tension with each other, managed in equilibrium over time, not declared once and left to run on autopilot.
Holding productive tension requires a team that can say hard things to each other.
When my clients assess where the organization stands on growth – those things that are imperative both in and outside the organization to foster and sustain growth – I see the same outcome the Harvard analysis describes: individual answers that differ significantly from each other, each carrying different implications for strategy. Same for purpose. Same for evolution. Each person has been carrying their own private interpretation of the strategic reality and vision, and the planning process has been building on top of those unspoken divergences. The strategy, at that point, is not built on reality, but on what everyone was comfortable saying out loud.
Believe it or not, growth is often the easiest of the three questions for teams to navigate. Purpose asks a different kind of question, one that challenges a more emotional perspective: is what we say we’re here to do actually compelling to the people inside this organization, and equally valuable to those served? That question is uncomfortable because strategy has often already disconnected from purpose and vision, and now the team has to acknowledge it and figure out how to pull it back into relevance.
Evolution asks something harder still: what about the way we operate today is no longer adequate for where we need to go? Naming that requires disconnecting both ego and investment from things that no longer serve the good of the entity or those it supports and serves. These are not questions a planning facilitator can answer. They require the people in the room to offer their real assessments – of the organization, of each other, and sometimes of decisions they themselves made.
That’s where equilibrium becomes the connective tissue of the whole framework. Equilibrium is not balance in the static sense; it is the ongoing, active management of purpose, growth, and evolution in relationship to each other. When growth outpaces the organization’s capacity to sustain it, someone on the team has to be willing to say so. When purpose has drifted from reality into rhetoric, someone has to surface it. When evolution is being resisted because it threatens comfortable assumptions, someone has to name that too. None of that happens in a team merely pretending to be in alignment. The strategy that comes out of a room where those honest signals never get voiced fails not because the framework was wrong, but because the team was unable to cohere at the level needed for it to work.
What Team Connection Actually Enables for Executive Team Performance
When I have seen strategy creation work well, what made it work was almost always that the team knew each other. Not in the surface-level, shared-a-few-offsite-dinners way. They understood and respected how each other operates. They knew who tends to hold back in early discussion and needs space to land their thinking. They knew whose instinct to challenge early assumptions is a gift, not a threat. They knew which combinations of people produce the best debate and which produce avoidance.
That knowledge changes everything about what’s possible in the strategy room. The CFO doesn’t have to navigate the politics of challenging growth assumptions when the team already knows that’s her role and respects it. The operations leader doesn’t have to wonder if naming an execution constraint will read as resistance when the team has language for that kind of honest input. The conversation moves faster, goes deeper, and produces something the people in the room actually believe.
That is not a soft skill benefit. It is a direct return on strategic investment.
The Question Most Never Ask Before They Plan
Organizations spend considerable time choosing the right planning framework, preparing the right data, and securing the right facilitation. Very few spend equivalent time asking whether the team that will do the strategic work is actually ready to do it. Not competent, which most leadership teams are, but genuinely connected in the ways that honest strategic thinking requires.
Understanding how each person in that room thinks, decides, and engages isn’t a personality exercise you do at a team retreat and file away. It is strategic intelligence, the kind that determines whether your planning process produces a document or produces a direction the people responsible for it genuinely own.
That’s exactly where my partners at PrinciplesUs come in. The second half of this article is written by Patrick Reilly and covers how personality science gives teams a practical, observable path to the kind of connection that makes robust, executable strategy possible.
What Teams Need Before Strategy Can Really Work
From the Principles perspective, the problem is usually not that leadership teams lack intelligence, experience, or commitment. It is that they are trying to do extraordinarily demanding strategic work without enough shared understanding of how the people around the table actually think, communicate, and respond under pressure.
That matters more than most teams realize.
In nearly every strategy session, there are predictable dynamics running just beneath the surface. One leader is pressure-testing assumptions, but gets read as obstructive. Another sees execution risk early, but hesitates to voice it because they do not want to derail momentum. Someone else thinks out loud and is mistaken for certainty, while a quieter colleague is still processing and gets overlooked. None of this is about bad intent. It is about teams making consequential decisions without enough insight into how each person naturally engages.
That is where self-awareness and other-awareness become useful, not as labels, and not as shortcuts, but as practical tools for better teamwork.
When a team has a clearer understanding of each member’s tendencies, the conversation changes. Challenge feels less personal. Silence gets interpreted more accurately. Faster processors make more room. More deliberate thinkers enter earlier. Teams get better at distinguishing real misalignment from differences in style, pace, and communication. What looked like friction becomes information. What felt political becomes discussable.
This is one reason we believe this kind of insight belongs upstream of strategy execution, not downstream of it. It helps create the conditions that good strategy depends on in the first place: trust, candor, role clarity, productive conflict, and shared ownership. In our work, we often describe those conditions through the 5Cs: Connection, Candid Communication, Clarity, Collaboration, and Contribution. Together, they describe the environment that allows teams not just to agree in the room, but to stay aligned when real tradeoffs, pressure, and accountability show up.
Two of those conditions matter especially here. Connection is about trust and the sense that people can show up honestly with one another. Candid Communication is about psychological safety, healthy conflict, transparency, and the belief that the best idea should win on its merits. These are not side issues. They are part of what determines whether a team can actually do strategy well. In our research, Connection emerges as the strongest predictor of job satisfaction, while Candid Communication is the strongest predictor of performance.
That helps explain why so many strategic plans stall after the offsite. The issue is often not the framework. It is that the team never built the relational and conversational conditions required to use the framework well. A team can have smart people, strong data, and a polished planning process, and still fail if members are filtering reality through private assumptions about one another.
What teams need is not just more discussion. They need better visibility into how they work.
That is where Principles can help. By giving teams a practical way to understand differences in working style, motivation, communication preferences, and decision-making tendencies, it becomes easier to turn vague interpersonal friction into something teams can name and work with. That creates a foundation for more empathy, more precision, and more honest dialogue. Our own work consistently points to the value of helping teams better understand one another’s preferences, working styles, and motivations so they can build trust, strengthen support, and collaborate more effectively.
The point is not to create perfect harmony. Strategy rarely requires that. It requires a team that can surface different interpretations of reality, challenge each other without collapsing into defensiveness, and commit together once a decision is made. Better self-awareness and other-awareness do not remove tension from that process. They make the tension more productive.
And that may be the question leaders should ask before they ask a team to align on strategy: do we understand each other well enough to tell the truth, disagree well, and execute together?
