Using coaching questions to develop the plan for the change you seek

Post & pens output of a planning session driven by coaching questions

Here I will discuss how to leverage Coaching Questions to Shape Strategic and Tactical Planning and to help you through your change or transformation.

During a recent delivery consultancy engagement, I facilitated a planning session that made me realise something powerful: the most impactful tool I used wasn’t a framework or a methodology—it was coaching. Specifically, a series of open-ended questions that helped the team collaboratively develop both a long-term roadmap and a short-term delivery plan.

On reflection, it struck me that this ap

proach wasn’t limited to just business projects. These questions are versatile, applicable to any change initiative—whether guiding large teams or supporting individuals through change and transformation.

Here are the open questions we discussed. If you’re considering making a change, start by reflecting on these prompts — and feel free to share your thoughts once you’ve worked through them.

Step 1: Define a High-Level Roadmap

Begin by engaging those directly involved in or impacted by the change (even if that’s just you), and explore the following:

• What specific outcomes do you want to achieve — and by when?

• What will success look like, sound like, and feel like?

• How will you measure this success? Who can independently verify it?

• What is the minimum viable delivery that would still meet your goals? ie the least you can do to achieve your objectives

• What key milestones or stages lie between now and your end result?

• What else? And what else? And what else?  …. 

• What support, resources, or people will you need — and when?

• Who must you collaborate with to secure those inputs on time?

• What indicators will help you track whether you’re on course?

• What risks could derail progress — and how might you mitigate them?

• What else? And what else? And what else?  …. 

Step 2: Develop a Short-Term, Detailed Plan

Zoom in on a realistic timeframe — perhaps 2 weeks to a month. This takes the high-level roadmap and provides your actionable detail:

• What is the timeframe you’re planning for?

• Based on your roadmap, what daily or weekly actions are necessary to stay on track?

• What else? And what else? And what else?  

• Who is responsible for each activity?

• What are the prerequisites and dependencies for each task?

• In what sequence must these actions occur?

• At the end of the period, how will you evaluate progress?

• Who can confirm that progress has been made?

• Are there any new risks or obstacles — and how can you stay ahead of them?

By the end, you’ll have:

• A high-level roadmap

• A timeline with defined milestones

• Key dependencies

• Indicators to track progress

• Risks and mitigations

• A detailed near-term plan

• Roles and responsibilities

• Clear success criteria

Let me know if you’d like this turned into a template or visual framework — I’d be happy to help you refine it further. Or if you want to tailor this for a specific audience or change initiative, just say the word.