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Strategy is Hard for Productive People

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I’m a list maker, aspirational Inbox Zero’er and general organizer and tidier. My peers poke fun at me for always asking for an agenda or goals at the start of a meeting, and never leaving one without asking ‘what are the next steps?’. I’m not apologetic for this — I, unsurprisingly, think it’s the right way to make sure the least amount of time faffing around meetings is wasted — and I’m an introvert so I have pretty much no skills at water-cooler chat anyway.

So when my partner Lew Moorman kept repeatedly telling me during strategy meetings that trying to get an immediate result was not the right goal — I really struggled!

You have to wallow in it.

Try as I might — I think it’s extremely difficult to sit at your desk or go to a meeting and ‘figure out our strategy’. It’s not a case of starting at point A and working to point B. The answer has to be discovered. Discovery is a creative process — it takes time. Some sessions feel like a total waste and then towards the end you have a light bulb moment. Just when you start gravitating back to task-based discussions, someone in the group gets an “aha” or sparks an “aha” in someone else — and then the strategy flows quickly and freely.

I think most productive people have a natural aversion to anything that involves wallowing. We just want the answer! “Just tell me or lets decide now — I’ll go execute!”

In the past year, we’ve had strategic breakthroughs in a good number of our portfolio companies at Scaleworks. Now I’m a believer in ‘thoughtful wallowing’ in the discussion around strategy. I’m constantly amazed at how these breakthroughs emerge.

Strategy is the most important keystone of your business. Everything flows from it. Getting it “right” makes planning and decision making seem effortless — things become obviously right or clearly wrong in light of a clear strategy.

My goal with this short post is simply to suggest — give yourself permission to wallow in strategy discussions. Some sessions will point to glaring holes in your data and customer validation — that’s an easy “go-do” fix. Other sessions will come up with ideas that sound great and 24 hours later fall apart. And more sessions will be fruitless discussions that give more questions than answers.

But — I’m now confident that time is the defining factor — be patient and make strategy setting a top priority — dedicate time to it each week until you are happy you have a defendable, clear and easy to articulate, position in the world.

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