5 steps to a great strategic conversation

You want to have a deep and meaningful conversation about ‘where next’ and you pull together your leadership team and trusted advisors to do just that. But, you’ve found yourselves in the same, rather dull, cul-de-sac, talking about more of the same or variations on, all too familiar, themes.

Old habits die hard – you’re habitually talking to the same people about a suite of well-rehearsed risks and opportunities in the context of a deeply ingrained perception of the business model and the external environment it inhabits.

I know everyone’s incredibly busy, but if you tag a couple of additional hours at the end of a recurring operational management meeting, your odds of indulging in high-quality strategic debate are drastically shortened. The best strategic conversations are holistic, deep, challenging, and creative – they demand days rather than hours.

Put a monthly day (or half a day if you’re really struggling) into your diary and further strengthen this with a short quarterly retreat (1-2 days). It sounds like a lot of time, but I can assure you it will pay huge dividends in terms of challenging assumptions, identifying strategic options, imagining innovative solutions to contextual problems, and growing together as a team.

Human beings tend to find, and be drawn towards, data and opinion that substantiates their existing beliefs. Leaders and teams of leaders are no exception. Existing data sets are explored and extrapolated by familiar analysts and trusted advisors, further deepening the established belief system.

Dare to bring in new information, to seek unfamiliar perspectives and to add to your portfolio of advisors and facilitators. Each new ‘data point’ will carry the possibility of an innovative spark that might light up new paths and point to new destinations.

Strategic conversations often follow a well-defined (and well-trodden) path linked to the annual budgetary process – perhaps featuring a more substantive conversation on every third or fifth cycle. The questions are on repeat year on year and a game develops in how best to respond to achieve favourable budgetary outcomes and protect against perceived failure. This treadmill approach (where strategy is often secondary to budgetary concerns) forces people to ‘hold their tongue’ and totally stifles creativity.

Give people permission to think the unthinkable and say the unspeakable (in strategic terms). Encourage them to raise the spectre of a changing strategic context, to spot embryonic trends, to seek out alternative paths and to suggest creative ideas and experiments that may require a bit of courage. Create a set of questions that encourages open minds and makes it clear that nothing is taboo. Venture into the unknowable future and ask what if?! 

If you encourage curiosity and cultivate creativity, you’re likely to hear things you might not want to hear. The easy way out is to pay lip-service to the contribution and move on with your existing plans regardless. This will achieve two things – your strategy will continue to follow the existing trajectory (which may or may not be a good thing) and people will not expose themselves again by sharing information, opinions and ideas. Not listening is dangerous and refusing to hear is, frankly, irresponsible.

Some of the biggest risks to organisations are already understood and openly discussed by those that are closest to them. Those grumblings about a technical issue or a competitor’s behaviour or a badly designed product are  early warning signs from the engine room – ignore them at your peril. Make a point of listening to what’s really being talked about across the organisation, how people feel about it and why they feel that way. Make it your mission to listen, hear and understand, and always be mindful not to turn the volume down too much.

The truth of a situation varies according to the vantage point you’re viewing it from. Our perspectives are clouded by our experiences and, less consciously, by our beliefs and values. In any given situation, there are likely to be many truths that we are each unaware of; any one of which may have massive impacts or unforeseen consequences. By expanding the group of people involved in strategic dialogue beyond the usual suspects, we can naturally inject some broadening of group perspective and opening of individual minds. Uncomfortable as it may feel, a conversation of diverse, open minds is far more creative than a comfortable convening of ‘like-minds’. Group think is particularly dangerous when contemplating potential futures and the risks and opportunities they may present.

Go out of your way to widen your strategic conversation, to make it genuinely inclusive and to generate curiosity and engagement beyond typical participants. And invite this broader group to be part of the genuine strategic dialogue – not a sideshow put on in the name of engagement that runs parallel to the real event, while the actual thinking is done by the usual suspects behind closed doors!