“Strategy won’t land if people don’t trust the process—or each other.”
At Thriveworks, we often support organizations during critical planning moments—off-sites, leadership retreats, strategy cycles. Everyone is ready to roll up their sleeves and chart the path forward. Sometimes we notice the conversation gets stuck—not because people don’t care, but because something deeper is in the way.
A Smart Strategy, but No Traction
Let’s say your organization has developed a solid strategic plan. The goals are aligned, the roadmap is clear, and everyone agrees—on paper. But then:
- Team members don’t follow through on agreed actions
- Conversations loop without resolution
- Some voices dominate while others stay quiet
- People say “yes” in the meeting, but don’t act outside it
It may seem like signs of poor planning but these may actually be signs of a trust gap—and a culture that isn’t fully equipped to carry the strategy forward.
Strategy Doesn’t Work in a Vacuum
The assumption that strategy is purely technical—a set of goals, objectives and metrics—is outdated. In reality, strategy lives or dies in relationships.
When people don’t feel safe to speak up, disagree, or take risks, strategy becomes performative. When trust is low, compliance replaces commitment. And when culture is brittle, even good ideas can’t gain traction.
When this takes root, the organization appears to be making progress, but nothing truly changes. Momentum is lost and not because the strategy was wrong, but because the conditions for execution weren’t in place.
Make Trust a Strategic Enabler
We believe trust and culture are not the soft stuff—they are the infrastructure of effective leadership and execution. Whether you’re guiding a team, a board, or a whole organization, intentionally focusing on trust and culture are strategic assets. And like any asset, they require care, attention, and investment. Here are a few ways to start:
- Name What’s Unspoken
Before jumping into content or frameworks, take time to acknowledge what might be getting in the way of real dialogue. Are there unvoiced concerns? Past friction? Confusion about roles?
In a recent board/leadership retreat we facilitated, simply asking “What needs to be said before we begin?” opened the door to addressing long-standing board-management tensions. That honest five-minute check-in cleared the air and laid the groundwork for better decisions.
Why it matters: Unspoken dynamics often shape what gets said—and what doesn’t. Surfacing them early builds psychological safety, and invites courage into the room.
- Use Process to Build Culture and Strategy
The planning process itself is a message. It shows what’s valued, whose voices count, and how power is shared.
Before an off-site or planning session, we work with clients to explore:
- Are the right people involved in shaping the conversation?
- Have we gathered meaningful input—not just data—from across the organization?
- Are we designing space for divergent thinking, not just alignment?
- Are we setting up the stakeholders to collaborate, not compete?
In one nonprofit we worked with, the shift from “presentation mode” to “strategic inquiry” transformed board meetings from passive reviews into dynamic, future-focused discussions.
Why it matters: An inclusive, well-designed process builds ownership and momentum. People don’t resist plans they helped shape.
- Treat Trust Like a System
Trust doesn’t live in individuals—it lives in systems. It shows up in how decisions are made, how conflict is handled, and how feedback flows.
If you want to strengthen trust, look at your systems:
- Are expectations and roles clear between board and executive?
- Is there transparency around decisions and trade-offs?
- Do your norms encourage candor or caution?
For example, one leadership team we worked with created a standing “assumptions audit” at the start of planning cycles. That small structural change helped them spot blind spots and reduced defensiveness over time.
Why it matters: Systemic trust creates resilience. When the environment supports clarity and accountability, people focus less on protecting themselves and more on leading effectively.
- Invest in Repair When Needed
When trust has been broken—through unmet commitments, leadership transitions, or interpersonal missteps—organizations often try to move on without addressing it. But trust doesn’t rebuild itself with time; it rebuilds through action. We’ve seen teams regain alignment after years of drift—not by jumping into a new strategic plan, but by first naming what wasn’t working, clarifying expectations, and committing to a different way of working.
Why it matters: Rebuilding trust creates new energy for strategy. Without it, planning becomes hollow—people may show up, but they won’t lean in.
In Closing
Strategy doesn’t fail because people don’t care—it fails because the foundation for alignment and action isn’t fully there. Trust and culture may be invisible, but their impact is undeniable.
Whether you’re a leadership team preparing for change, or a board navigating complexity, taking time to build trust into your planning process is an intentional way to maximize your chances of success.
Want to Go Deeper?
We’ll be exploring the topic of broken trust in more depth at the CPHR BC & Yukon Conference on Wednesday, April 30, 2025, where we’re leading a session on Repairing Trust – Essential Skills for HR Professionals. If trust breakdowns are impacting your or your organization’s ability to lead through change or implement strategy, we invite you to join us.
And if you’re planning a strategic off-site or leadership session this year, we’d love to help you build the kind of trust and culture that ensures your strategy doesn’t just get written—it gets lived. Reach out to us at hello@thriveworks.ca to explore how we can support you.
