Back 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.

Here's how it works. Any time I feel I'm at a crossroads and I need to make a big decision, I pretended that I'm on stage with a famous journalist (Kara Swisher for some reason), in front of tons of people. Resumator is already wildly successful. The interviewer and I are revisiting this exact point in time of the business--right now--and I'm describing the challenges we faced.

The interviewer then asks, "So what did you do next?"

That's when my mental wheels start turning. Remember, this is an interview about how the business succeeded, so although at the time we may have "successfully re-launched our website," that's obviously not the reason we did well long term. In this fantasy/real thought exercise, the future audience and present business are both waiting for the strategic decision that put us on the path to winning.

What was/is it?

I then just start talking to myself (the shower is great for this). I keep throwing responses out there and try to see if one sounds like the right next move. I even make up the results. Eventually one idea is worth sharing with the broader executive team:

"We clearly defined who our customer was, and cut product initiatives that didn't meet their needs. Sales grew immediately.

"We opened a West coast office to tap into the Marketing talent there. We now have a great team."

"I decided to quit my job because I knew I was highly employable. Best decision I ever made."

I don't always make the right decision of course--but I know I've made a clear-headed decision with the long-term business goals in mind. Ultimately you need to leave this fantasy world and truly look at what's going on inside your company to make the right decisions. But any time I face an important decision, part of my thought process around what to do involves adding another segment to this fictitious interview. And yes, sometimes part of that interview includes a humble, "I was wrong." Luckily, I know what my interviewer is going to give me another chance:

"So what did you do next?"

One of these days I'll be able to answer, "Made a ton of money for me, our employees and investors. And yes--we changed our small corner of the world for the better."

Until then, the interview continues.

Published on: May 21, 2015