Strategic Conversations: The Hidden Driver of Successful Transformation

Business transformation is never just about strategy, technology, or structure. It’s about people—and how we engage them in the process of strategic change. Communication during times of transformation isn’t a checkbox. It’s the core that builds trust, reduces resistance, ignites possibility thinking, and aligns people toward shared goals.

In a recent Forbes article, Kurt Allen draws on 25 years of experience in marketing and communications to highlight: “communication is the critical success factor in business transformation.” Whether you are launching a new product or service, rebranding, or realigning, the difference between success and failure often lies in how conversations are handled—or whether they happen at all especially with the employees closest to your customers.

This is where strategic conversations come in. Rooted in Conversations Worth Having: Using Appreciative Inquiry, these conversations invite leaders and teams into a different kind of dialogue—one that fosters clarity, connection, and momentum. Rather than delivering top-down messaging, leaders ask, listen, and learn through inquiry-based dialogue that leads to shared meaning-making. Appreciative Inquiry is a widely embraced, strengths-based approach to organizational change. Used by organizations such as the U.S. Navy, Green Mountain Coffee Roasters, Apple, Accenture, Google, Cleveland Clinic, the United Nations, and Verizon, it helps teams uncover what’s working, explore new possibilities, and co-create positive futures together.

The Conversations Worth Having framework has one technique and two appreciative practices:

Technique: Tune In to Others

The first move in a strategic conversation isn’t talking and telling. It’s tuning in.

When you pause, take a breath, and get curious (that’s tuning in), it creates space to notice what’s needed, both emotionally and strategically. Is your team clear or confused about the organization’s transformation? Are people feeling overwhelmed or energized? Are they going to engage or resist?

This awareness helps you open the door for a two-way communication exchange.

Allen emphasizes this in his article by sharing how regular feedback sessions and listening groups helped surface concerns and adjust communication in real time. Leaders who tune in signal that they value people, not just performance.

Practice 1: Ask Generative Questions

An organization’s leadership team that is planning or even going through a transformation might spark excitement and engagement or fear and resistance. If you want to spark excitement, then strategic conversations invite people to imagine what’s possible and how they might help.

This starts with generative questions—those that spark insight, creativity, and shared ownership.

Questions like:

• “What does a successful transformation look like for you?”
• “What do you need to feel confident moving forward?”
• “What strengths can we build on to navigate this change?”
• “What ideas do you have about what’s possible – what might be?”

Transformation begins not with answers, but with the questions that invite us to explore what’s possible together.

Practice 2: Frame the Conversation Topic/Challenge Positively

Positive framing isn’t about sugarcoating the transformation. It’s about helping people see the opportunity within the transformation. Strategic conversations frame challenges as invitations to grow, adapt, and evolve together.

Allen shares how aligning messaging with the organization’s mission and purpose during a transformation helps rebuild trust and boost engagement. When people see how change connects to purpose—and how they fit into the bigger picture—they are far more likely to commit and contribute.

Transformation Is a Conversation

At its core, business transformation is a conversation—a series of moments where people decide whether to resist, comply, or engage. When leaders use the strategic conversation framework—tune in; ask generative questions; and use positive framing—they invite people into the process, not just the outcome. 

As Allen writes, “When people understand the ‘why’ and ‘how’ of change, they’re more likely to embrace and drive it themselves.” Strategic conversations help make that understanding—and shared ownership—possible. 

Ready to Lead Transformational Conversations? 

For a quick start, check out our 30-minute CWH Foundations Course

For a deeper understanding of the power of Conversations Worth Having in everyday life and to lead strategic conversations, check out our Conversation Bootcamp and Strategic Conversations Bootcamp (both on-demand and virtual in-person). 

Whether you're navigating a transformation or simply want to have more meaningful conversations, our resources training programs equip you with the mindset and skills to make every interaction count. Learn more at: www.cwh.today

Shared by Jackie Stavros, DM
I believe the way forward in any transformation—organizational or personal—is through conversations that build trust, spark shared purpose, and ignite possibility. When we tune in, ask generative questions, and frame change with hope, we create the conditions for people to come together, contribute, and thrive. Most of us want to be heard, valued, and part of something bigger. Conversations Worth Having make that possible, which increases the likelihood of successful transformation.