I spent last night at a vinyl listening party—no screens, no distractions, just Erin Ivey on stage with her producer and fellow musician in an intimate room. We listened to her new album Souvenir the way it was meant to be heard: eyes closed, fully present, absorbing not just the songs but the stories behind them.

The warmth of vinyl revealed layers that digital streaming flattens. It struck me: This is exactly what’s missing in most business strategy right now.

The Pattern: Leaders Who Listen Win

Here’s what I’m watching play out with clients as we close out 2025:

New CEO Listening Tour

A new CEO—five months into her role—is spending her time on listening tours. Not quick virtual check-ins. Not surveys. Real conversations with customers and employees. She has her senior strategist doing the same, expanding her reach so they can come back together and synthesize what they’re hearing.

The result? They’re defining the company’s direction and initiatives for 2026 based on actual signal, not assumption.

Post-M&A Customer Conference

Another CEO just completed five M&A transactions and hosted the company’s first virtual customer conference with 400+ attendees and multiple breakout sessions. But here’s what made it strategic: He and his team weren’t just presenting—they were listening.

Every breakout session was designed to understand what each acquired company’s customer base cares about and how the combined entity will serve their needs.

Those insights are now shaping how they weave together a narrative that pulls the employee and customer base together. Not in some theoretical “synergies” way, but in concrete initiatives that matter to the people who actually use their products.

The AI Paradox: Why Human Connection Matters More Than Ever

AI tools are extraordinary. We use them. Our clients use them. They make us faster, sharper, more efficient.

But here’s what they can’t do:

• They can’t read the hesitation in a customer’s voice when you ask about contract renewal
• They can’t catch the energy shift in a room when you hit on something that truly matters to employees
• They can’t build the trust that comes from a CEO showing up in person and saying, “I want to understand your world”

 

The more automated our workflows become, the MORE valuable these irreplaceable human moments are. This isn’t nostalgia. It’s strategy.

What Makes a Listening Tour Actually Work

When a new CEO steps into a role, one of the first things they need to do is go on a listening tour. Not because it’s a nice gesture. Because it’s how you gather the intelligence you need to make smart decisions about where to take the company.

But most leaders get this wrong. They treat it like a PR tour—talking at people, explaining their vision, selling the future.

The ones who get it right do something different:

Expand reach strategically Like the CEO who has her senior strategist running parallel listening sessions. She’s not trying to do everything herself. She’s multiplying her capacity to hear signal.

Design for real conversation The CEO who used a 400-person virtual conference as a listening exercise didn’t just broadcast. He created breakout sessions that gave customers space to share what actually matters to them.

Synthesize before deciding Both of these leaders are taking what they hear and using it to shape strategy—not just checking a box and moving on.

When Listening Becomes Mission-Critical: The M&A Multiplier

If listening tours matter for new CEOs, they become absolutely essential during M&A.

When you’re bringing together multiple companies, each with their own customer base, culture, and way of doing things, you need more than a communications plan. You need intel:

• What are customers worried about?
• What do employees from the acquired company need to hear?
• Where are the unexpected synergies that only emerge when you ask the right questions?

The companies that navigate M&A successfully don’t just announce the deal and hope for the best. They build listening into the integration strategy from day one.

That’s how you get zero customer churn. That’s how you avoid the $8M mistake—the one where top customers learn about major news from an email instead of a conversation.

Build Your Foundation Before You Need It

Here’s the pattern that keeps showing up:

The companies that succeed through high-stakes moments—M&A, major funding rounds, leadership transitions—are the ones that invested in relationships and listening before they needed something.

They didn’t wait until the deal was closing to think about stakeholder communications. They didn’t treat customer relationships as transactional until they needed renewal signatures. They built a foundation of genuine connection that became a strategic asset when it mattered most.

As we head into 2026, this is more important than ever. If you’re planning a major move in Q1 or Q2—funding, M&A, restructuring, repositioning—now is when you should be thinking about your listening strategy.

Not in January when you need a press release. Not in March when the deal is closing. Now, before the structure is set, so what you learn from listening can actually shape your strategy.

Planning Your 2026 Listening Strategy

If you’re a CEO or leader heading into a high-stakes moment in 2026, here’s what to consider:

Who needs to be heard? Customers, employees, partners, investors—map out the stakeholders whose input should shape your strategy.

How will you expand your reach? You can’t do all the listening yourself. Who on your team can run parallel conversations so you can synthesize more signal?

What will you do with what you hear? Listening only matters if it shapes decisions. Build time into your planning process to integrate what you learn.

If you’re approaching a major funding round, M&A, or leadership transition and want to talk through your stakeholder strategy, let’s schedule time. This is the work that prevents the $8M mistakes and turns high-stakes moments into strategic wins.

Strategic Listening and Stakeholder Engagement: Key Questions

How long should a CEO listening tour take? For a new CEO, plan for the first 90-120 days to include substantial listening time. For M&A scenarios, build listening into the first 6-8 weeks post-announcement. The key is making it systematic, not just ad hoc conversations.

What’s the difference between a listening tour and regular stakeholder meetings? Intent and structure. Regular meetings have agendas and deliverables. Listening tours are designed to gather signal—you’re asking open-ended questions and creating space for stakeholders to tell you what matters to them, not just responding to your agenda.

Can listening tours work virtually, or do they need to be in-person? Both can work, but they serve different purposes. Virtual expands reach and works well for broad intelligence gathering (like the 400-person customer conference). In-person is irreplaceable for building deep trust and catching the nuance in how people respond. Strategic leaders use both.

What’s the biggest mistake leaders make on listening tours? Talking more than listening. The second biggest? Listening but not synthesizing—gathering input without creating a process to turn that intelligence into strategic decisions.

How does Red Fan help clients with stakeholder listening strategies? We help design the listening architecture before high-stakes moments—mapping who needs to be heard, what questions to ask, and how to synthesize insights into communications strategy. For M&A specifically, we integrate listening into our six-week stakeholder communications playbook so what you learn shapes how you position the transaction.

What should I ask on a listening tour? The most revealing question is often the simplest: “What should I know that I haven’t asked about?” Or “What concerns you most about [the transition/merger/change]?” Open-ended questions give people permission to share what’s actually on their minds.

Planning a high-stakes move in 2026? Let’s talk about your listening strategy before you need a press release.