What is the toughest choice to make in Strategy? Well, it's a certain type of tough question - not one you draw a blank on, but one where too many answers come to mind. Is it about challenging the value-system? Or convincing an organization that it is not 'strategy-ready' yet? The 'toughest', finally, is a subjective one, and my pick may easily be different from yours. In my present frame of mind, I think one kind of the toughest choice is to pick options that don't 'look' good.
I'm sure you'll agree that at times the best choice is to do nothing. At times, it is to close down a business, or to wait out a storm, or to walk away from an opportunity - and so on, right? But now imagine actually sitting in one of these day-long workshops and when the time comes to condense choices, it is one of these. It'll take a brave CXO, or a group of leaders, to conclude that it is best to do one of these things (or nothings, to be precise). It is much easier to say you'll reinvent yourselves, or acquire some as-yet unidentified target or any other equally esoteric statement, but it's really tough to say, for instance, that you'll wait it out and do nothing for now; or that you seem to be in a good place and it won't be wise to rock the boat. Examples of such not-good-looking choices abound. I'm not hung up about the examples above, but you get the drift.... There's a huge stack on the other side, of words that may not mean much, like re-organization, reshuffling, re-prioritization, deep-diving, outside-in propositioning that may also not mean much more, but sound much better.
Another interesting insight is that it is easier to say we'll do nothing when times are bad, in the 'all hands on deck', belt-tightening, no-nonsense struggle to stay afloat. It gets tough when all this becomes 'business as usual', and there's enough time to ask what-else and what-if.
And then you see the plight in action. You get in and out of strategy workshops that are like, as someone said, a Chinese dinner that makes you feel quite full for an hour, but then you wonder if you have eaten at all. You'd often find leaders scrambling to avoid the plight of the non-good-sounding, for race to find the perfect words to say nothing.
Sad, isn't it?