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Five Conversation Starters for Leaders Steering Through Messy Change 

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Hello Friends, 

If there is one constant theme in our client work right now, it is change and adaptability: restructures bump into tariff shifts, budget cuts collide with new tech rollouts, and everyone is trying to keep up. Leaders tell us, “Our people seem worn thin, but we still have to move.”

Our gentle nudge back is always the same. Yes, we can move and honor the human curve at the same time. 

Below are five questions I rely on when I am coaching executives through complex change. They surface hidden fears, locate folks on the J-Curve, and turn compliance talk into partnership talk. Use them in one-on-ones, team huddles, or your next all-hands. If you are an HR pro, consider forwarding this to the leaders who need it most.

 

1. “What might this change cost you personally?”

Change is experienced first as loss—status, routines, or a sense of mastery. We cannot skip the grief. Ask early, and you invite honesty instead of hallway whispers. Listen for worries about relevance, workload, or team cohesion. Those clues tell you where trust needs extra care.

 

2. “Where do you feel we are on the journey—free-fall, learning, or climbing?”

This plain-language scale lets you map the J-Curve without a slide deck. When people name their spot and hear yours, the gap between leadership optimism and employee reality shrinks. Shared language does not equal shared emotion, yet it is a solid start.

 

3. “What don’t you know yet that would help you move forward?”

Leaders forget they have lived with the decision for months; everyone else got the memo yesterday. This question flushes out missing context, unclear goals, or opaque decision criteria. Every answer is a breadcrumb toward transparency.

 

4. “Where could we safely experiment together to test this change?”

Partnership beats persuasion. Co-design a pilot that feels low-risk but real—one shift, one client, one sprint. Small wins expand psychological capacity faster than another town hall pep talk ever will.

 

5. “After we act, how will we know we protected trust—both results and relationships?”

Trust erodes quietly unless we measure it. Invite the team to define signals: quicker turnaround times, fewer late-night pings, candid feedback loops. When the metrics include relational health, people see that you mean it. 

 

Putting the Questions to Work 

Choose one question and drop it into your next meeting agenda without fanfare, just genuine curiosity. Capture responses, circle the themes, and commit to one concrete action for each theme. Repeat every quarter; the questions stay the same, yet the conversation and culture will grow. 

If you are ready to go deeper, watch for our upcoming Leading Through Resistance online course, launching this fall on Leader Campus Plus. Early adopters will receive additional tools and live Q and A discussions with Teresa and I, perfect companions to the five-question playbook you just read. 

Changing with people, not at them—that is the work.

 

With you on the journey, 

Sarah Noll Wilson
Speaker, Coach, Persistent Question-Asker 😊 
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Sarah Noll Wilson is on a mission to help leaders build and rebuild teams. She aims to empower leaders to understand and honor the beautiful complexity of the humans they serve. Through her work as an Executive Coach, an in-demand Keynote Speaker, Researcher, Contributor to Harvard Business Review, and Bestselling Author of “Don’t Feed the Elephants”, Sarah helps leaders close the gap between what they intend to do and the actual impact they make. She hosts the podcast “Conversations on Conversations”, is certified in Co-Active Coaching and Conversational Intelligence, and is a frequent guest lecturer at universities. In addition to her work with organizations, Sarah is a passionate advocate for mental health.

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