Jesse Jacoby
In any organization, the success of a long-term strategic initiative depends not only on vision and execution, but also on communication. Particularly when the initiative spans a year or more—as major transformations, technology deployments, or organizational redesigns often do—leaders must embrace a proactive approach to keeping stakeholders informed. It’s not just a matter of courtesy. It’s a matter of alignment, trust, and momentum.
Strategic Initiatives Are Rarely Linear
Most long-term initiatives do not progress in a straight line. There are inevitable periods of pause—moments when leaders must evaluate early feedback, re-examine assumptions, recalibrate timelines, or pivot entirely based on new information. These inflection points are necessary and often beneficial, but they can feel like voids to those not involved in the daily decision-making.
If leaders remain silent during these recalibration periods, stakeholders begin to fill the void with their own interpretations—often shaped more by uncertainty than reality. Rumors start, confidence wanes, and resistance builds.
Don’t Wait for the Perfect Message
There is a natural instinct among well-meaning leaders to delay communication until every detail is locked down. But in the context of long-range initiatives, this instinct can backfire. Waiting “just one more week” to perfect a message can easily turn into a month of silence. In the meantime, engagement and clarity erode.
Instead, leaders should err on the side of early and honest communication. Share what you know when you know it. A brief but authentic update—“Here’s what we’re learning, here’s what’s changing, and here’s what we’ll update you on next”—can do more to maintain confidence than a polished memo sent weeks too late.
The Curse of Knowledge
Authors Chip and Dan Heath coined the term “the Curse of Knowledge” in their bestselling book Made to Stick. The concept is simple but powerful: once you know something, it becomes hard to imagine what it’s like not to know it. This blind spot can be especially problematic for leaders and program teams deep in the weeds of a strategic initiative. They may assume that certain decisions, tradeoffs, or changes are obvious to everyone—when in fact, they’re not.
Leaders must actively fight the Curse of Knowledge by stepping back and asking: What do our stakeholders actually know? What assumptions are we making about their understanding?
Communicate for the Age of Continuous Partial Attention
We live in a world of Slack pings, Teams messages, notifications, and constant distraction. It’s unrealistic to expect stakeholders to digest long emails, attend every town hall, or wade through dense decks.
The key is to communicate in bite-sized, intentional bursts. This might include:
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Weekly or biweekly “Quick Hits” emails: Focused on top takeaways in bullet form
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Short video updates from senior leaders: 2–3 minutes max, with a clear call to action or next step
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Single-slide visuals that show progress, decisions made, or upcoming milestones
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Pinned updates in collaboration platforms like SharePoint, Confluence, or Teams Channels
And always, end communications with an invitation: “Questions? Feedback? Here’s how to get in touch.”
Transparency Builds Trust
Strategic initiatives, especially those that last more than a year, will face challenges. Some plans will need to shift. Success will sometimes look different than what was originally envisioned. But stakeholders are far more likely to stay engaged and supportive when they feel included in the journey.
Transparency isn’t just about providing information—it’s about building credibility. It signals that you trust your stakeholders to understand the complexities of change. It shows that you value their input. And it reinforces that you are leading with integrity, even when the answers aren’t yet final.
In Summary
Long-term strategic initiatives require more than executional discipline—they require communicative discipline. Pauses and pivots are inevitable. When they occur, don’t wait for the perfect story. Share what you know, acknowledge what’s still in motion, and do it in ways that respect your audience’s limited attention span.
Leaders who master this approach earn something invaluable: the benefit of the doubt, even when plans change. And in the world of strategic transformation, that can make all the difference.
