Navigating Executive Waters: Strategic Communications with Becky Sail

This month, Greenough was incredibly fortunate to host the renowned Becky Sail - communications extraordinaire and recreational kayaker - in our Boston office, where she shared invaluable insights on moving the needle with executives in a high-pressure, rapidly evolving landscape. Her expertise highlighted the significance of this core skill for communication professionals, and the team truly benefited from her thought-provoking perspectives. Drawing on her experiences and integrating the collaborative spirit of our engaging workshop, these key takeaways from Becky’s session outline critical lessons from this meeting-of-the-minds.  

Why Working with Executives Feels Like Kayaking in Whitewater

Navigating the world of executive communications can feel a bit like kayaking through unpredictable rapids—exciting, nerve-wracking, and not something you’d sign up for unless you can keep your cool. For communications professionals, the real challenge is being more than just the person writing the press release and securing the hits in the media. We need to be the strategic partner bringing both well-earned expertise and fresh perspectives to keep the whole team afloat. 

The Unique Pressures Leaders Face

With the massive AI transformation and fluctuating economy, executives are facing a unique set of challenges, and it’s more than just a full inbox. Accountability for the organization, pressure from a board or C-suite, and tough calls on layoffs or organizational changes are their daily backdrop. Trying to win attention with slide decks while leaders juggle these responsibilities takes sharp focus, clear strategy, and genuine understanding to break through their daily noise.

Understanding and Preparing for Your Audience

Success starts by knowing your audience, but not in a generic “I Googled their LinkedIn” kind of way. It means diving deep into how executives process information, and most importantly, what truly motivates them. Some respond to data-driven insights; others appreciate when you cut to the chase with a strong point of view. Showing up to a meeting prepared, with concise recommendations and zero “death by slides”—not only earns respect, but keeps conversations lively and productive.  

Real-World Examples of Strategic Partnership

You don’t have to look far for proof that strategic comms makes a difference. At top innovation summits, leaders repeatedly emphasize the benefits of internal-external collaboration in driving real results. We work with brands ranging from disruptive startups to public companies, but the road to success is always the same: alignment around a clear mission. As one executive noted in a recent planning meeting, “It’s about finding someone who wants to be on the mission with you.” The message: it’s not just what you know, but how you invest in shared purpose. 

Balancing Big Ideas With Pragmatic Execution

When executives have grand ideas—like launching an in-depth video campaign “by next week”—the best move isn’t just a reflexive “yes” or “no.” Instead, outline what successful execution would look like, propose a pilot, and back up your recommendations with data. In this case study: gently explaining the realities of producing professional content alone can help set new expectations and open minds to more innovative approaches, allowing the team to align on a strategy that really makes an impact.

The Importance of Transparency and Follow-Through

Consistency and transparency are essential ingredients for lasting trust. The most valued partnerships are built by those who consistently deliver, sometimes even ahead of schedule. That legendary “giant teddy bear moment” (when the toughest executive thanks you) might feel rare, but showing up with clarity, summaries, and next steps builds a reputation that endures. “Do what you say you’re going to do” isn’t just a catchphrase; it’s the secret handshake of high performers.

Building Enduring Partnerships with Humor and Expertise

Ultimately, working with executives isn’t just about strategic accuracy or polished presentations; it’s about creating genuine, lasting partnerships. Our consummate goal at Greenough is to focus on managing complex topics in a way that feels efficient and even enjoyable. By anticipating needs, providing clarity, and engaging in honest, authentic conversations, you earn the trust to be in the room and help guide the way. The key takeaway for communication professionals and companies alike:  

• Prioritize thoughtful preparation & know your audience.

• Invest in trust; do what you say you’re going to do.

• Recognize the value of showing up with authenticity.

Thank you, Becky, for joining us! We hope to have you back again soon!

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