Can This Exercise Help You Strategize?

EXEBack in 2007, when I was figuring out how to (and if I could) become a tech entrepreneur, I consumed hours of video interviews with the stars of tech startups. These entrepreneurs were currently growing or previously built wildly successful startups. I wasn’t just interested in the story, but also the strategy. The interviewer would convince the founder to share their biggest hurdles, greatest epiphanies, and critical pivots on the journey to fame and fortune. It was very interesting to hear how they made decisions at key milestones or during tough times in the business:

What did you do after you won your first customer?

So you’re stuck at $5 million, what was the key thing that set you on the path to $500 million

In business, the most important move (read: key action or decision) is always the next move. When you string a series of strategic moves together, they eventually lead your business to an outcome. That outcome will plot itself on the spectrum between absolute failure and meteoric success. No matter the stage of your business, you’re going to constantly need to ensure that your decisions move your company’s trajectory in the right direction.

From personal experience, I can tell you this is way, way, way easier said than done. It’s hard to think strategically (the mountains) when you have so many tactical things (the trees) right in front of you. You can easily get caught up chopping down trees instead of preparing to climb mountains. If you don’t think strategically, you’ll eventually reach the base of the mountain unprepared and struggle to grow (there’s a reason they call it “scaling” your business).

Over the years I’ve developed a quirky technique to help me clear my mind and think strategically when needed: I pretend I’m being interviewed. Yep.

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