We co-hosted a dinner with London School of Economics, sponsored by Tide Bank, for 12 entrepreneurs who are scaling their businesses.
We introduced our End Game Studio ethos to the group and used conversation cards to stimulate conversations around each Founder’s end game intentions.
Here are some examples of the questions we posed…
Build with the end in mind
Goal: Shifting the perspective from daily firefighting to long-term intentionality.
"If your business was a finite, 10-year project rather than an infinite machine, how would that change the decisions you are making this week?"
"When you picture the day you finally step away from this business, what is the feeling you most want to experience in that first week?"
"We often build systems to survive us. What part of your business is currently too dependent on your identity and capabilities, and what's one step to untangle it?"
"Can you think of any businesses or founders you admire who have had a great exit that you would like to replicate?"
Compared to your original mission, to what extent have you accomplished your company's aims??"
"If you had to write the 'final chapter' of your company's story today, what would the title be?"
There’s no such thing as a good or bad ending
Goal: Embracing complexity, contradictions, and dismantling the "shame" narrative.
"What is a 'successful' outcome for your business that might actually feel like a personal loss—and vice versa?"
"In the startup world, 'pivoting' is celebrated but 'pausing' or 'closing' is feared. When have you seen a closure or exit done with immense dignity or grace?"
"What is a belief about leadership or success that you’ve had to completely let go of as you moved from startup to scale-up?"
"If you could unburden yourself from one expectation that investors, the market, or your team has of your 'final destination,' what would it be?"
Game (not) over
Goal: Reframing identity beyond the current venture and looking toward new beginnings.
"As a founder, your identity gets deeply fused with your company. Outside of being 'The Founder of [Company],' who are you becoming right now?"
"If you exited your business tomorrow with total financial freedom, what is the problem in the world you would want to tackle next—even if it’s entirely unrelated?"
"What skills or wisdom have you developed during this scale-up phase that you are most excited to 'seed' into your next chapter or into the wider ecosystem?"
"What is the one souvenir you would take from your business to remember it by?"
"How would you like your leadership to be remembered?
It is never too early to think about your end game, even when you are scaling up. Reflecting on the sort of legacy you want to leave behind can help you to make the decisions that will serve you well in the future.
Thank you LJ Silverman and Joanna Hamer for inviting us to bring our Game Not Over energy to LSE alumni!
