Bridging the Gap: Aligning Leadership and Staff Around Strategy

Strategy isn’t just something written down or stored in software. It must be lived, discussed, and executed.

Leadership teams are deeply immersed in strategy, sure, integrating it into their decision-making processes, reviewing it in every meeting, and adjusting it based on business conditions. But for most employees, strategy is something they only hear about in the occasional brown bag session or during quarterly reports.

This gap creates a fundamental disconnect. Without meaningful engagement, staff members don’t feel connected to the strategy, leading to misalignment, lack of accountability, and ultimately, a failure to reach strategic goals. Leadership can close this gap and build trust by actively bringing strategy to life through collaboration—not just through software tools, but through everyday interactions where people already work.

The Leadership-Staff Strategy Gap

Leadership teams often assume that because they live and breathe strategy, their employees do too. In reality, most employees experience strategy only at a distance. While executives are immersed in strategic discussions, staff members may only see an annual strategic plan document or sit through an all-hands meeting sharing high-level goals. This lack of regular engagement creates a disconnect that can lead to misalignment, disengagement, and even resistance to strategic initiatives.

For an organization to succeed, every team member must understand how their work contributes to the broader strategy. This requires ongoing communication, not just occasional check-ins.

Building Trust Through Strategy Communication

Before the digital age, collaboration was defined by tangible interactions. Face-to-face meetings and telephone conversations were the cornerstone of effective collaboration—the wait, the intentional deliberation—created a depth of engagement that fostered trust and intimacy. In-person discussions allowed for the subtle nuances of body language, tone, and even silence, all of which contribute to a richer understanding between parties.

When I reflect on my early career, I recall the strategic sessions where my colleagues and I would huddle around a conference table, our ideas evolving organically through a mix of debate, humor, and occasional disagreements. That moment of pause to consider a colleague’s perspective often led to breakthrough moments.

This open communication is key to building trust and engaging employees in strategy. Many organizations make the mistake of treating strategy as something that is “done to” employees rather than something they actively participate in. When strategic discussions are “done with” employees, they’ll feel that their input matters, be more likely to buy into the vision, and take ownership of their role in execution.

In short, collaborating fosters transparency and alignment. Instead of limiting strategic discussions to leadership meetings, organizations should create opportunities for staff to engage in meaningful conversations about strategy. Leaders should share updates regularly, solicit feedback, and make strategic progress visible across the organization.

The Pillars of Strategic Collaboration

Over my career, I’ve come to identify several pillars of successful collaboration, grounded in years of real-world experience and hard-won insights.

1. ‍Human Connection: No matter how advanced our tools become, the value of a genuine, face-to-face conversation remains unmatched. Whether it’s a strategy meeting at ClearPoint or a client negotiation, investing time in personal interaction often pays dividends in clarity and trust.
2. ‍The Right Tools for the Right Jobs: Simple updates might be best handled through a quick chat message, but complex issues deserve a meeting—whether in person or via video—to fully explore nuances and build consensus. One emerging trend I find particularly exciting is the integration of AI in facilitating meeting dynamics. AI tools that provide real-time transcription and sentiment analysis can help us identify summaries, takeaways, and action items.
3. ‍A Culture of Respect: At ClearPoint Strategy, we emphasize clear communication protocols. We encourage our team to ask clarifying questions, to be candid about uncertainties, and to question our own assumptions. This culture not only allows us to arrive at better, well-thought-out solutions, but also fosters an environment where innovation thrives.

The Culture of Collaboration

The Psychological Element

Human beings are inherently social creatures, and our brains are wired to respond to subtle cues. In my early days as a consultant, I learned that the key to unlocking a team’s potential often lies in fostering a sense of safety—a space where individuals feel comfortable sharing bold ideas without fear of immediate dismissal.

At ClearPoint, we strive to create settings where every voice is heard. Whether we’re using state-of-the-art digital tools or simply gathering around a conference table, our goal is to nurture conversations that build trust and encourage vulnerability.

Company Culture

A company’s culture plays a pivotal role in how collaboration is leveraged. In some organizations, employees may report feeling isolated or overwhelmed by constant digital chatter, where personal connections are sacrificed for efficiency. Yet, you don’t want to over-communicate, either. Organizations that balance a quick ping versus high-touch interactions well tend to have more cohesive teams and stronger performance.

For business leaders, the key to thriving is adaptability. This observation has informed our strategy at ClearPoint, where we’re guided by the principle of continuously reassessing our processes to ensure our interactions enhance our conversations, rather than dilute them.

Encouraging Strategy Engagement

At ClearPoint, we recognized these challenges early on and built tools specifically designed to close the gap between leadership and staff when it comes to strategy. Tools that help enable strategy engagement for all:

• ‍Discussion Threads and @Mentions: Allow employees to engage directly with strategic elements such as KPIs, projects, and OKRs through comment threads. The ability to @mention colleagues ensures that the right people are pulled into relevant conversations.
• ‍Integrations: Seamless integration with familiar tools, like Microsoft Teams, allows users to discuss strategy in the platforms they already use without switching applications. Real-time discussions, quick questions about strategic initiatives, direct data retrieval, you name it.
• ‍Scheduling: Scheduling automated reporting cadences allows strategic insights to consistently be shared, keeping teams aligned without requiring manual updates or distribution efforts.

By embedding strategy discussions into existing, daily work processes, ClearPoint helps organizations make strategy execution a continuous process, rather than a periodic event.

Free eBook: Make Strategy Everyone’s Job (in 5 steps!)

Change Management and Strategy Execution

One of the most critical aspects of strategy execution is managing change effectively. Strategic initiatives evolve over time, and it’s essential to keep track of these changes to ensure alignment and accountability.

An approval process allows organizations to track updates to strategic elements, ensuring that leadership is aware of modifications and can provide oversight. By keeping a clear record of changes, organizations can maintain continuity and avoid confusion about which version of the strategy is being implemented.

Making Strategy a Daily Practice

Aligning leadership and staff around strategy requires fostering a culture of collaboration. Leaders must be proactive in integrating strategic discussions into daily workflows, ensuring that employees have clear visibility into their own role in the larger strategy.

Through open communication, transparency, and workflows that make strategy a daily practice, organizations can bridge the strategy gap between leadership and staff, ultimately driving better execution.

The first step? Start making strategy a part of everyday conversations—wherever your employees already work.

The first step to the first step? Demo ClearPoint Strategy’s collaboration tools here (for free—in just 30 minutes).