Closing Your Own Strategic Bet
As senior leaders, you take strategic bets.
You make the case. You get the funding. You staff it with people who had other options.
Eighteen months in, it has not worked.
The most objective thing now appears to be calling it off.
However there are challenges:
Knowing it has really failed: A strategic bet is supposed to take time. “It has not worked yet” and “it will not work” look identical from the inside. Without criteria you are negotiating with your own hope. Who wins by arguing with hope?
Holding on Vs Letting go: The sunk cost is not just the money. At your level, the investment includes your judgment. Closing the bet means conceding something about the person who made it. You are protecting yourself, and it is why the arguments for one more quarter feel so reasonable.
How do you get past them?
Set the exit criteria in writing (if not already done):Write down what you would have to see, with a date. Not what you hope to see. The difference between those two sentences is the whole exercise.Then put the question to yourself the way you would put it to someone else: If this landed on your desk today, with this evidence and this cost, would you fund it?
Understanding what are you protecting: You have usually concluded this long before you act on it, so the gap is willingness rather than insight. What makes it bearable is changing the question you are answering: you are not announcing that you were wrong, you are deciding where next quarter’s money and people go. One of those is about your past. The other is the future.
How to do it well:
Sequence the share: Your executive first, your team next and others
Articulate the basis of your projections and what changed: “We expected enterprise buyers would move within two quarters considering buyer behaviour research. Across eleven accounts the median was nine months and the deal size halved.”
Separate the conviction from the execution: Usually one of them was more sound. Saying which is what makes you credible to bet again.
Skip “we learned a lot”: Name one thing you will do differently and stop.
Resolve the financial commitments.
Protect the people who banked on you: Place them deliberately and visibly. Tell their next manager/organisation what they actually did. Make sure the story that travels is about the bet and not about them.
Reflect
What are you still hoping for that you should let go ?
What would have to be true for you to close it, and have you written it down?
If someone else raised it first, what would that cost you?
Where did the people from your last failed bet end up?
