You’ve signed off on the strategy. The project team is mobilized. Change is in the air. But a few months in, momentum has stalled, again. Why does it feel like transformation always hits invisible roadblocks, no matter how well you plan?
For every ambitious transformation that delivers, there are dozens that drag, detour, or quietly dissolve into “business as usual.” Boards and executive teams set bold targets and project managers jump into delivery. But somewhere between the boardroom and the coalface, good intentions get lost in translation.
I’ve spent over two decades working at this intersection: guiding transformations, supporting project teams, and sitting alongside executives as they wrestle with change. If there’s one recurring theme, it’s this: Project managers see things executives don’t, and they rarely say it outright.
Here’s what they wish you knew.
1. Clarity Beats Certainty
It’s a myth that project teams need certainty before moving forward. In reality, what they crave is clarity, on direction, priorities, and non-negotiables. Executives sometimes wait until all the answers are clear before giving the go-ahead, but transformation is inherently ambiguous.
“Just tell us what matters most—even if the answer might change.”
Executives who frame the “why” and define what’s truly important empower project teams to act decisively, make smart trade-offs, and maintain momentum even when the path isn’t clear.
2. Shifting Goals = Wasted Effort
It’s normal for strategy to evolve as you learn. But when priorities pivot too often, or aren’t communicated clearly, project teams lose traction. Resources are reallocated. Work gets redone. Progress stalls.
“It’s not the change that hurts, it’s not knowing which change matters.”
When executives provide context for strategic shifts and acknowledge the impact on the delivery team, it builds trust. Even a short “here’s why we’re changing course” can make all the difference.
3. Culture Is the Project
Project managers will tell you: the technical plan is the easy part. The real challenge is shifting mindsets, habits, and daily behaviors across the organization. Yet, too often, cultural work is sidelined as “soft” or “somebody else’s job.”
“We can deliver the new process, but if the culture isn’t ready, it won’t stick.”
Executives who engage visibly in culture change, modeling new behaviors, rewarding experimentation, and calling out resistance, signal that transformation is everyone’s business, not just the project team’s.
4. Silence Isn’t Agreement
Early warning signs rarely show up in status dashboards. Project managers notice the first cracks; misaligned expectations, growing fatigue, or subtle stakeholder resistance, well before issues become “red.” But they often hesitate to escalate, fearing blame or that they’ll be seen as negative.
“If it’s not safe to speak up, we’ll keep quiet, until it’s too late.”
Executives who invite candid feedback, reward transparency, and treat risk as information (not failure) surface problems when they’re still manageable.
5. Recognition Drives Results
Transformation is hard work. Wins are often incremental and rarely celebrated. Yet nothing boosts morale like a genuine, public “thank you” from the top. Project teams want to know their work matters, that executives see and value their progress, not just the final outcome.
“It doesn’t have to be awards, just visible recognition that the work is seen.”
Regular, authentic recognition from executives is a force multiplier for energy, engagement, and resilience through the inevitable bumps of change.
How Executives Can Bridge the Gap
So, what does it look like to turn these truths into action? Here are four simple, high-impact moves any executive can make:
- Ask for clarity, not just progress: Regularly check in on what’s clear and what’s ambiguous. Don’t punish uncertainty, help resolve it.
- Create space for real talk: Go beyond status updates. Ask, “What’s not on the dashboard that should be?” and mean it.
- Sponsor the hard stuff: Show up for the difficult conversations—especially around culture, conflict, and ambiguity.
- Champion learning (and pivots): Celebrate smart course corrections, not just hitting the original target.
You can turn these into a quick checklist for your next project review:
- Have we defined what’s non-negotiable?
- Are shifts in strategy explained and acknowledged?
- Are we surfacing early warnings, not just managing by dashboard?
- Are cultural signals and behaviors getting executive attention?
- When did I last recognize and thank the delivery team—publicly?
Closing Reflection & Call to Action
If you’re an executive leading a transformation, try this simple experiment: Ask your project managers what they wish you understood about their world. Really listen. You’ll be surprised at what surfaces, not just risks and challenges, but practical solutions and new energy.
Transformation is a team sport. When leaders and delivery teams share the real conversation, not just the official version, change shifts from a grind to a game-changer.
Project managers, what would you add to this list? Executives, how do you keep the conversation real in your transformation journey?
No responses yet