Every leader should be asking the management team to ponder the future. Not about the next quarter or next year. You need to look far out and ask:

What would you do, if you knew you couldn’t fail?

The pressure of doing business today, of beating the last quarter and making the next, is too often an stagnation to deeper strategic conversations that your organization ought to be having. You need to see the big picture, and in too many organizations the big picture isn’t big enough.  To develop a much broader view, ask everyone within the business to write down their ideas about the following questions. Make it clear that responses may be shared (either anonymously or with personal attribution) to stimulate discussion about topics that should be addressed.

  1. What strategic issues are of most concern to you in your current position or more broadly for our organization as whole? Speaking truth to power is difficult, but when approached effectively gaining grass root insight can be the most invigorating and cathartic opportunity for business owners to really see the future capacity within their current framework.
  2. What is your typical time frame for strategic decisions and long-term planning? How many years out are you thinking and what is the business scope you normally consider, from local or regional to global? Leaders have to know since they need to think longer term and farther afield than the management team; if not the leaders, who will? When I was fortunate to work with the Executive board of a leading supermarket chain, I was always enamoured by the Chairman’s 13-year business forecast. Even though, strategically they only planned 3-5 years ahead.
  3. What would constitute some very bad external scenarios for the business, including social, political, economic, ecological, legal and regulatory forces or technologies that are beyond your control? It is only when we begin to expect the unexpected that we start to understand the flaws and frailties within out business and begin creating sustainability measures to fend off rival or hostile take over opportunities.
  4. Conversely, what especially good external scenarios could plausibly happen over the next five years, covering perhaps the same but also different topics, forces, themes or issues? Good news scenarios are psychologically easier to envision but can still easily be overlooked or misconstrued. It’s good to take risks in business, but measured risks are far more easy to enter into and adapt if rehearsed, than when we are caught in a storm we never anticipated.
  5. More fanciful yet, what would be the top three questions you would ask in order to help you better perform your current leadership responsibilities and/or help the company overall? What would you ask your future self that could aide you make the right decisions right now. And what would you future self reply!
  6. What are some current or upcoming strategic decisions for which some of the above scenarios and/or uncertainties are especially relevant, and why? Suppose your big upcoming decisions are about opening a new office, launching a new product, or entering a promising strategic partnership. You now need to examine how these possible moves play out under a good vs. bad scenario and some in-between cases as well. In short, try to stress test your choices. Think OUTSIDE your business, outside your geography, outside your industry.  What are the BIG things requiring attention right now, and what are YOU doing to address (or support those who ARE addressing them)
  7. Which external issues are the most important for you to track over the next 12 months, either for your own area or the organization more generally? What metrics would you ideally monitor? Forward-looking measures are clearly better than rear-view mirror ones. Your early warning dashboard should be tied to both your strategy and external scenarios.  If you want to track shifts in consumer preferences or service quality for instance, look at customers you lost and why. If you ask them, and know how to listen with a third ear, you can learn a great deal from them, your rivals and your own people.
  8. What significant external developments were spotted too late in the last five years by you or the organization; why do you think these blind spots occurred? Also, what important developments did you spot ahead of time; what helped you or the firm stay abreast of these undercurrents?

Once the right issues are surfaced, various approaches can then be followed to develop suitable responses, such as resolving pressing choices near term or developing a sharper strategic vision for the long term. The leader’s imperatives here are to start the strategic conversation from the outside-in, make room for diverse and even unpopular inputs, develop an inclusive process, and respect uncertainty by not trying to predict what is unknowable. Then, test the robustness of any decision or strategy against multiple scenarios of how major external uncertainties could play out.  The broader these uncertainties are, the more flexibility should be built into your strategy, say by using an options approach when making large investments. Relatedly, leaders need to reward alertness to external changes and foster organizational agility, so that quick actions can be taken when needed.

In essence, the game today is about being smarter, quicker, more agile than the competition and to set yourself such a Big Fat Hairy Audacious Goal as to concentrate the mind for every single employee for every day of the year, that makes such a huge difference to the world it would be scary NOT to achieve it!