Organisations and individuals strive to be seen as strategic. In the business world being strategic is seen as an indicator of future success. Yet I frequently witness conversations that are intended to be strategic that truly are not. I recount the number of coaching conversations aimed at helping individuals ‘become more strategic’ in their thinking, a typical development goal for many, and I think back on the number of executive sessions that I have facilitated where teams have struggled to entertain the challenge posed and have remained in their comfort zones discussing tactics.

Having recently observed a similar situation, I was prompted to write this post. I wanted to share a consolidation of my thoughts; things that I have observed as common elements of all inefficient strategic conversations and what makes for a great one.


A great strategic conversation is more likely to occur when the issue being discussed is not urgent. Now, one might argue that an urgent issue creates a ‘burning platform’; and, this in turn should mobilise energy, attention and commitment from those concerned to quickly resolve a strategic issue. However, I often observe the contrary. Urgent and very ripe issues very rarely attract the quality of thinking that they deserve. These conversations seem to foster a crisis mentality for those concerned and this results in stunted problem solving. Very often this leads to decisions around tactics and not strategy! Many leadership teams have become conditioned over time to rally around crisis situations rather than calmly and proactively steering their ships through the waters.

Addressing issues when they are important rather than in a negative spiral will stimulate creativity and give space to consider unconventional options.


This is a conundrum in itself. Adaptive challenges (typically those that benefit from a strategic conversation) are of such significance to the business that Exec teams by default assume that they need to get round the boardroom table and thrash it out to reach a decision. Another unhelpful trait that I observe is fake participation whether due to political correctness or disingenuous asks for input! What often gets overlooked in all these modes, however, is the value that genuine and wider involvement could bring in resolving the challenge. ‘Heads of’ and the ‘C-suiters’ might be the ones to own the ultimate decision, but a good and thorough strategic conversation won’t limit the discussion potential to those solely holding the decision rights. Equally, question involving those that on reflection won’t have the judgement, experience or intuition to contribute.

Convene your dream team of contributors; those that would think outside the box, those that would think in different boxes, and those that don’t even see the box – this might involve customers, suppliers, technical specialists…


What is the purpose of the conversation? Great strategic conversations have a clear purpose. Often a conversation is initiated without clarity on whether full understanding is present amongst those contributing. If the contributors have divergent views or inconsistent understanding then shaping the resolution becomes a difficult conversation. And if choices are not carefully evaluated on the basis of a common understanding then making a decision becomes near impossible.

Follow a logical process in your strategic conversation. Make sure that there is common understanding first, then shape the choices and then evaluate those to arrive at a decision.

Timing (again!)

Now in a different context, how much time should we devote to a strategic conversation? Naturally this depends on the topic at hand, however, all too often I observe these discussions being rushed into a tightly packed executive agenda and hence not allowing the space and consideration needed to get the clarity and resolution required. An efficient strategic conversation or meeting will strike a perfect balance between over analysing the issue and keeping momentum and energy in the debate.

There are many different ways to ensure an efficient strategic conversation – probably more than there are challenges to resolve in the first place! This is not about right or wrong, it is about how to make the best of the opportunity to truly generate some breakthrough insights. As Einstein once said, “If you do what you always did, you will get what you always got!” A strategic conversation deserves more than just your standard meeting.

Too little time will stunt creative discussion and limited participation, but too much might have an de-energising effect. Use a healthy dose of data, intuition and experience to move the conversation to a decision.