Ways to Engage Skeptical or Unaware Executives

Jessica Guistolise and Keith Tanaka presented a talk at Agile 2025 entitled—I’m the SVP Who Didn’t Know I Needed Help—How to Reach Others Like Me.

In it, they went over eleven ideas for engaging executives in agile contexts. One of the KEY slides they presented was—

And, since the picture is a bit grainy, here are the eleven ways they presented—

1. Storytelling – Using narratives to create connection, build trust, and illustrate agility in action.

2. Coaching – Helping executives discover insights for themselves rather than being told what to do.

3. Fostering Alignment – Reframing agility in terms of leadership priorities and business outcomes.

4. Strategic Reframing - Shifting the conversation from Agile practices to risk reduction, efficiency, and growth.

5. Inviting Curiosity – Asking thought-provoking questions that encourage exploration rather than resistance. (see #2)

6. Leveraging Peers – Using executive advocates to influence others at their level.

7. Practical Immersion – Engaging executives in hands-on experiences that make agility tangible. (games)

8. Empathy Mapping – Understanding executives’ concerns, fears, and aspirations before engaging in conversations. (see #2)

9. Story-based Influence – Teaching attendees how to build and use success stories that resonate with leadership. (see #1)

10. Aligning with Their Incentives – Connecting agility to what leaders are measured on (e.g., revenue, risk mitigation) (see #3)

11. Small, Low-Risk Experiments – Demonstrating agiliti’s value through incremental, controlled changes.

While I found the presentation well-delivered and quite useful, it struck me that all their ideas were from the perspective of—

• A coach

• A teacher

• A facilitator

Instead of jumping on the field of play with the executives, they were primarily trying to show, influence, or have them discover their path…entirely on their own.

I guess what I’m saying is that ALL their suggestions are more “influence and hope” actions. I wanted to see more—get in the game with them—actions.

This slide has a heavy Professional Coaching flair. It's not bad; it's just narrower than I’d like.

I think some of the CRITICAL things they missed were being a—

1. Partner

2. Co-Owner

3. Consultant

4. Advisor

5. Co-Leader

As an agile change agent, I’ll call these more get-in-the-game actions for you. Sure, they’re a bit riskier, but from an executive’s perspective, they’re also more active, engaged, and directly helpful to them. They also fly in the face of Professional Coaching or most Agile Coaching teaching that wants you to be a more passive participant in your client’s (SVP) evolutionary journey.

I’ve written about this notion of a more well-rounded approach (see Agile Coaching Growth Wheel) many times before. But to me, it’s more of an attitude of direct and active engagement.

For example, asking yourself—Am I…In the Arena and In the Arena

Food for your reflective thought.

Stay agile, my friends,

Bob.

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