#409 – June 22, 2025

Strategic Fit and Spicy Situations

Hello, fellow strategists!  In this issue we look at seven factors that influence strategic fit, negotiating tricky situations, tapping into your team’s experience, and pressures to adjust your online marketing. We also bring you some beautiful questions to ask and  other insights to help you succeed with strategy development. Enjoy!

 

Quick Takes

Drill on the Situation, Not Your Opponents

This week, while helping a client navigate a delicate, emotionally charged discussion with partners, we were reminded of a powerful principle: “the situation is the enemy, not those opposing you.”

This idea comes straight from former FBI hostage negotiator Christopher Voss and his instructive book, Never Split the Difference: Negotiate Like Your Life Depended on It.

When conflicting interests collide, it’s so easy for discussions to become personal and cloud judgment. Voss offers a perhaps counter-intuitive approach: focus relentlessly on the situation and the underlying interests, not the individuals involved.

Voss emphasizes what he calls “tactical empathy,” which isn’t about agreeing with the other side, but rather about genuinely seeking to understand their perspective, their motivations, their fears, and what’s truly driving their stance. By actively listening and using carefully calibrated questions (especially ones starting with “what” or “how”), you can begin to uncover the true dynamics of the problem at hand.

This shift in focus helps move the conversation away from accusations and personal attacks, creating a much safer space where both parties can really explore solutions. Voss teaches that once you can articulate the other person’s viewpoint so accurately that they respond with a heartfelt “That’s right!” – signifying genuine understanding – you’ve achieved a critical breakthrough.

 

Tap Into Your Team’s Experience

Leaders must take care to avoid being cut off from people and critical information. Edgar Schein, former MIT Sloan School expert and author of Humble Inquiry, has observed that poor upward communication plagues most organizations. “It’s a major pathology”, he says. Subordinates know lots of things that would make the place work better or safer, but they withhold them for various reasons.

You may resolve to walk around the workplace to connect and ask questions, but then get stuck on what to ask. In his Book of Beautiful Questions, Warren Berger suggests you start by asking yourself whether you want to focus on what’s broken, or what’s working well (an appreciative enquiry approach). Then, choose your question.

Berger recommends this one: “What are some of the biggest challenges you face in your role within this organization?”

(Or more specifically, “On this project, what’s the single toughest challenge you’re facing?”)

Follow up with “How can I help?”

 

Online Marketing Isn’t Broken, But It Is Different

If your go-to digital strategies aren’t working the same way they used to, online marketing expert and author Amy Porterfield says you’re not alone.

While email, webinars, and evergreen sales funnels still work, we need to evolve with them. Buyer behavior has changed, and that shift calls for better messaging and more personalized touchpoints.

“Cold audiences need clarity fast, and warm audiences need to feel reconnected,” she advises. “Revisit your visuals, refresh your messaging, and don’t assume your audience is the same as last year.”

When your online visitors are declining in number or not responding to your offers, Porterfield says, you’re getting signals to show up earlier, sell with clarity, and build trust over time.

 

8020Info Spotlight:

Seven Factors that Shape Strategic Fit

When we talk about “strategic fit” in planning, we’re really asking how well your organization’s plans align with your internal strengths and the world around you. That means ensuring your mission, programs, and daily work consistently connect with the real needs of those you serve, the expectations of key stakeholders (clients, staff, funders, partners, community members), and the skills and resources your team brings to the table.

For guidance, consider The Seven Essential Elements of Strategic Success, recently published by Harvard Business Review. These elements all influence one another and must work together, especially when conditions are unpredictable and ever-changing. They are:

• The Mental Model: We simplify complex realities with assumptions about people, purpose, and how the world works — just enough to guide daily decisions. Make sure your assumptions match reality.
• Purpose and Ambitions: Purpose involves why you exist and what you aim to achieve for others; ambition involves what goals you want to accomplish for your organization. Your true essence shows in your actions, not your words.
• Creating Value: Your strategy should enrich the lives of everyone connected to your organization — clients, employees, members, partners, funders, and community stakeholders. Everyone should benefit from supporting your goals.
• Macro Forces: Factors outside your organization — economic, social, technological, and political — can have a major impact. Your strategy must align with these larger forces.
• The Market for Your Products and Services: Whether you’re private, public, or nonprofit, you must regularly define the sector or market(s) where you’ll operate — and where you won’t.
• Comparative Advantages: Focus on your unique strengths and capabilities — the things that set you apart in your field. Build on them and adapt as circumstances change.
• The Operating Model: This is your organizational engine — structure, governance, leadership, culture, talent, processes, technology, and data — all working together to deliver results.

Strategic fit is never easy — and it’s never “done”. But when these seven elements work together, their combined impact can deliver a significant payoff.

 

For Your Reading List:  Beautiful Questions

The Book of Beautiful Questions by Warren Berger explores how asking the right questions can unlock creativity, improve decision-making, strengthen relationships, and lead to better leadership. Berger offers practical guidance and hundreds of example questions to help readers think more deeply and act more wisely in work and life. It’s a practical resource for curious leaders who want to sharpen their focus.

 

Closing Thought:  Perspective

“What you see and what you hear depends a great deal on where you are standing. It also depends on what sort of person you are.” — C.S. Lewis, The Magician’s Nephew.