
Over the last few weeks, we’ve been diving into the various layers of my strategic planning pyramid. So far, we’ve discussed the need for shared understanding [link] and the power of collective purpose [link]. In this post, we’re taking a closer look at the value of having diverse options.

The concept of optionality is one that is shared in great detail (and beautiful prose) by Dr Jason Fox in his book How to Lead a Quest [link]. In it, Jason cautions against leaning into the first option that presents itself. Instead, he advocates for having multiple options available – ready to draw upon as requirements and circumstances change. I believe this to be incredibly sage advice, though it runs counter to much of what’s traditionally taught in business schools.
The dominant perspective in many business schools is that the secret to success is based on specialisation and productivity. Find the one thing you can do better than your competitors, and then do that thing faster and cheaper than anyone else. And although this might be an avenue to maximising short-term profitability, it is always quite possibly also a shortcut to long-term irrelevance.
Why? Because in times of change and uncertainty, productivity and specialisation can be damaging. Consumer sentiments might change, market conditions might shift, new competitors might enter the market. There are lots of factors that can rock the boat when the conditions are uncertain.
Building on our analogy of the last few posts: if shared understanding is the map, organisational vision the destination, and collective purpose the compass – then diverse options are the alternate routes we might chart to get where we want to go.
When sailing, you rarely follow what is known as the rhumb line. The rhumb line is a direct line, or the shortest possible path between where you are now and where you want to go. Although you would think this is the best way to go, it generally isn’t. Quite often pesky things like islands and reefs get in the way, and tides can push you off course. More interestingly, the wind might favour a different direction entirely. Often, a longer route with better winds will get you to your destination faster.
Take, for example, this following map that shows the tracks of the three fastest boats to have ever sailed around the world (these boats all competed in the Trophée Jules Verne – a no-restrictions, global circumnavigation race with a current record of 40 days). As you can see, not one of them took the shortest course.

But, perhaps more important than just the course they took, is that at any one point the navigators on these boats would have had multiple possible options to pursue depending on how conditions might change. As options were eliminated because of the choices that were made, new options or courses needed to be created. You never want to be in a situation where you’re limited to a single course of action.
The same goes for any organisation operating in a dynamic and uncertain environment. At any one time you want to have multiple options at your disposal, and as options are eliminated, new options need to be identified.
One way to uncover these options is through processes like scenario planning. One of the most powerful stages in the process is the scenario workshop, where multiple possible future scenarios are presented back to stakeholders. Participants are then asked to capture the different strategic options that could be pursued in these various futures. The collective output becomes a suite of diverse, actionable paths. These options – though they may need further validation and refinement – are a far more robust starting point than simply copying competitors or repeating past strategies.
And, in case you missed it… I had a baby.

Well, not a real one – it’s a podcast. And instead of a christening, it has just been launched (which, of course, you shouldn’t do with babies).
The Future With Friends is where we dive into the futures that matter – work-life balance, death and dying, even the future of friendships themselves. Each episode, I invite a friend to imagine a world (scenario) at least five years from now, exploring their hopes, fears, and the wild possibilities ahead.
Listen now at thefuturewithfriends.com or find it on Spotify, Apple Podcasts, and YouTube.
Curious how this all came about? Click here – otherwise, just hit play and enjoy!

Simon