top of page

ChatGPT Asks Colin Iles About the Challenges Of Strategy Meetings

Interviewer - ChatGPT

(Details on how I created this article at the end)



In an enlightening conversation with Colin Iles, a visionary in strategic planning, we delve into the intricacies of conducting successful strategic meetings. Colin, with his rich experience in steering companies towards growth, shares his insights on transforming these critical sessions from mere formalities into powerful tools for organisational change.


ChatGPT: Colin, from your experience, what are the primary challenges companies face during strategic meetings?

Colin Iles: The core issue lies in the approach. Many firms either view strategic meetings as obligatory gatherings or run them as if they were. They therefore miss the opportunities for profound reflection and decision-making. These sessions should be where the company’s future is shaped, yet they often become bogged down in details, failing to address the bigger picture.


ChatGPT: What common mistakes do companies make in setting up these meetings?

Colin Iles: The biggest mistake happens at the planning stage, because the sponsoring executive (or executives) don't take the time to think about what outcomes they want and how they will stage manage the process. Getting the right executives, to have the right discussions, with the right mindsets is something that requires deep thought and careful orchestration at every level. Delegating the planning to junior staff, virtually guarantees sub-optimal outcomes, as they simply fill time-slots with presentations from other executives.

The focus becomes data and presentations rather than strategic thinking. Also, many companies confuse strategy with execution, failing to realise they require different mindsets.


ChatGPT: Could you elaborate on the importance of separating execution from strategy?

Colin Iles: Absolutely. Strategy is about deriving the vision and core objectives for the company. It requires a lot of visioning to think into the future about the problems your customers will have and how you can solve them at scale. It requires expansive thinking, no sacred cows and plenty of imagination. There can be no stupid questions, and the word "but" has to be replaced with "and", with a focus on exploring ideas, not killing them.

Execution, on the other hand, is more about turning these fantasies into reality, working practically on how to deliver.

These two different discussion types mix like oil and water. Just as oil always floats to the top, it's inevitable that without intervention, executives are always drawn towards execution-focused dialogues.

Failing to take active steps to ensure strategic thought is not subsumed by other matters always leads to narrowed thinking, short-term strategies and erosions of equity value.


ChatGPT: What recommendations would you give for improving these strategy sessions?

Colin Iles: Truckloads. Too many for this interview. But if I have to make one recommendation, I'd make this. Engage a skilled facilitator right off the bat who can help you orchestrate a session that counts. There are so many reasons why it just makes sense. Skilled strategic facilitators are vital sounding boards; they bring impartiality and independence, they help remove bias, they manage egos, and they introduce the right frameworks to ensure conversations have depth and relevance.


ChatGPT: How often should companies hold these strategy sessions?

Colin Iles: Great question and one that most companies answer wrongly. Most boards and executives have this cycle where strategy is reviewed on an annual cycle. But in a world where change is accelerating at exponential rates, I'd argue that this is not frequent enough. It's barmy when you think about it, that executives will review their operational metrics on a monthly, weekly or even daily basis to try to optimise delivery but look at strategy on set annual cycles. I believe that executives should allow themselves time to continually review and refine their strategies throughout the year. This means regularly challenging assumptions, bringing outside-in perspectives into their meetings and being comfortable updating their core objectives as circumstances change.

This should equate to at least three or four full/multi-day sessions each year, with regular mini-sessions throughout that provide spaces for conversations and ideas to continue developing.



Colin Iles' insights shed light on the transformative power of well-conceived strategic meetings. His emphasis on visionary thinking, clear objectives, and regular reassessment of strategies offers a roadmap for businesses to navigate the complexities of today’s ever-evolving landscape. By reimagining these sessions, organisations can unlock new pathways to growth and success.


About Colin Iles

Colin Iles is a strategist and thought leader known for his innovative approach to business planning and leadership. With a career spanning multiple industries, he brings a unique perspective on how companies can thrive in a fast-changing world.


This article aims to capture the essence of Colin Iles' perspectives and advice on strategic meetings, formatted as an interview by ChatGPT for a more engaging and informative read.


I started this article by sharing some ideas about how to run a decent strategy session by standing in the garden and interviewing myself.

I recorded the discussion and loaded it to Sonix to transcribe into text.

I then loaded it to ChatGPT 4 and asked it to create this interview-style article.

It took about an hour to edit it into something I was comfortable publishing.

Finally, I asked Chat to create a feature image that portrayed a robot interviewing me for this article.

If you want help structuring your next strategy session, dm me or email me at



bottom of page