A Leadership Team’s ‘WHY’
The Value of Knowing Your Executive Team’s WHY.os: Unlocking Transformation Success
I have found that in today’s fast-paced business landscape, leading a successful transformation requires more than just a strong strategy or compelling vision—it demands deep alignment within the leadership team. Every leader brings their own unique values, strengths, motivations, and priorities to the table. However, without a clear understanding of how these individual drivers influence decisions, team dynamics, and strategic outcomes, it’s nearly impossible to achieve true alignment - which your people need to lean into change. This is where I have found the WHY.os framework becomes a game-changer.
The WHY.os system uncovers each leader’s WHY (what motivates them), HOW (the way they work), and WHAT (the results they seek to achieve). When leadership teams take the time to understand these elements, both individually and collectively, they unlock a new level of cohesion, commitment, and performance that drives transformational success.
Here’s why I believe a tool like this can be a critical advancement to delivering real, measurable results that add value to stakeholders:
Our ‘WHY’ is About our Values - Aligning Leadership Values with Transformation Goals Is Powerful
Every leader is motivated by different values, and those motivations influence how they make decisions and execute goals. Without clarity on what drives each leader, misalignment can slow progress. When we are able to gain clarity to each leader’s values - when we understand if they trying to ‘Make Sense’ of it all, find a ‘Better Way’, or ‘Simplify’ everything - and align them with the company’s objectives, increasing commitment and motivation, a new level of engagement and commitment emerges across the leadership team.
For example, a COO whose WHY is “to simplify” may focus on operational efficiency, while a CMO whose WHY is “to contribute” may prioritize customer relationships and loyalty. Left to their own work, they may create priorities that are misaligned. Yet understanding these differences enables collaboration and smoother execution of transformation efforts, where all are leaning in to the same priorities.
Reducing Resistance to Change
I once took over an initiative where an executive had been creating significant roadblocks for an international change moment. By understanding what motivated him, and pulling him into the work in a way that fulfilled his needs, he quickly became a powerful advocate and ally helping me achieve success.
We hear a lot about resistance to change because we really aren’t dealing with processes - we are dealing with humans - and humans are complicated. Resistance is a common barrier to successful transformation, because people feel disconnected from the transformation’s goals, or fear the impact on their personal identity. By using WHY.os, you can help your leadership team connect personally to the transformation journey. Leaders who see how their WHY aligns with the company’s vision are more likely to embrace change, reducing resistance and driving momentum. When people feel personally invested, they shift from resisting change to actively supporting it - that’s where magic happens.
Strengthening Team Collaboration and Accountability
A successful transformation requires a leadership team that works together with a shared understanding of the value and roles each contributes to the overall success. Leveraging something like the WHY.os framework with team coaching creates a shared language, allowing leaders to understand their peers' motivations and work styles. We’ve found it easier to remove competing goals and replace them with stronger collaboration and new levels of joint accountability. Talk about a team dynamics shift!
For instance, when a CIO motivated by “mastery” understood how their role complemented a CEO driven by “challenge,” collaboration became more effective, and transformation efforts became more aligned and efficient. Their new-found partnership created a trickle down effect on their directs, which affected the people in their organizations. The result was one for the ages, as partnerships flourished and real results started being delivered.
Fostering Trust and Buy-In
Another powerful value-add is the affect all of this can have on trust, and subsequently the culture of an organization. When leadership teams are misaligned, trust typically suffers and cultures can quickly become ‘silently toxic’. Employees sense when leaders aren’t on the same page, which can lead to competition, disengagement and poor performance. Aligning leadership motivations through what I like to call ‘Why unity’ can create a united front and foster a culture of trust. People partner, they bring new ideas to the table, and performance begins to elevate. Who wouldn’t want that?
The reason is simple: when leaders are aligned, they inspire confidence in the broader team, making it easier for employees to commit to the transformation. Adoption grows and the positive measurable outcomes show the difference for all stakeholders involved.
The Power of Creating a Roadmap for Success
Once we’ve aligned a leadership through their Why’s, it’s time to create a strategic roadmap that guides the transformation over time. Looking forward for two to three years and providing a clear vision, helps everyone gain clarity the priorities and value their organizations add to the bigger goals of transformation. One thing to note here is that roadmaps should be visionary - which means we must allow flexibility. Think of it as being “written in sand, not chiseled in stone”—the vision remains, but the tactics can adjust to changing circumstances. They should also be built on outcomes over activities. Too often we see people executing against activities that were committed 18+ months ago, yet are really no longer relative. The world changes. The technology changes. The stakeholders needs change - your roadmap should too!
We’ve all experienced the ‘but we’ve always done it this way…’ moment. Leveraging a neutral, outside expert can be invaluable in helping leadership teams create this roadmap. An external facilitator can challenge assumptions and limiting beliefs, prevent groupthink, and ensure the roadmap pushes the team toward innovation and success while maintaining alignment. This creates a strategy that the team can trust and rally around, advocate for, and lead through.
Final Thoughts
Knowing your team’s WHY.os doesn’t just provide insight into personal motivations—it unlocks an even stronger level of team dynamics and potential. When leaders understand their own WHY - and their peers WHY - and how they all fit into the bigger picture, they become more committed to transformation, inspiring others and ensuring that the results are not just meaningful but sustainable.
Ready to explore the WHY.os? You can self-purchase an assessment on the Learn Your Why page, or connect with us to plan a full team WHY.os session.
