Today I am writing to entrepreneurs on behalf of their senior leadership teams… to give you a permission you may not think you have during strategic planning sessions.

Picture this…

A beautiful all-glass conference room overlooking the downtown and river area in Wilmington, Delaware. We are gathered there, about 11 of us, to do our quarterly strategic plan based on the Scaling Up methodology. This quarterly plan ties to our annual plan (developed in same space), that ties to our 3-5 year plan and our BHAG.

I am standing there, about 2pm on day one after hours of conversations… staring out at the river and in my mind BEGGING my team to come up with the next quarterly priority. The excitement about this day (because I love strategy) has completely worn off.

You see, I already know the priority. In fact, I knew all the priorities before we even walked in the room but fancied myself a “democratic leader” where we all collectively build “consensus” on the objectives. It was important to me that we all designed our strategy together, and not just me spouting it off.

Guess what? 

What I didn’t know was that the team actually DREADED these planning sessions because we belabored the strategy discussions for most of day one and then ran out of time to plan their execution. Every. Single. Time.

So it was torturing them and torturing me! 

Finally as I stood there wondering how hard it would take to head-butt and break the window I was staring through, I blurted out –

“Hey, I think X,Y, and Z are the last 3 priorities that should round out our quarter.” 

Then quickly apologized for not courting any discussion but we needed to move on… 

What happened next astonished me…

Sighs of relief! Someone said “thank god” and another “I totally agree!”

It turns out that trying to involve everyone in the strategic THINKING was outside of most of the teams’ skill set and not something they were interested in at all. Me trying to be inclusive was driving them crazy. They loved EXECUTION PLANNING!! How to take a strategy and make it reality…

This has been a long standing rant for me. Be a benevolent dictator when it comes to strategy. You are the CEO/Entrepreneur. You own it. It’s yours. That doesn’t mean you don’t take council (more on that in a future email) or that you don’t take input.It means you don’t drag out of your poor team what you already knew in the first place!! Who knows… if you do this right maybe you can even skip out on the EXECUTION PLANNING phase, because admit it, that bores most of your as entrepreneurs.

So, on behalf of me and your senior team, I am granting you permission to be the CSO, Chief Strategy Officer, while being the CEO! Come prepared with what you believe are the priorities ahead of time. Share them. Debate if need be but don’t waste time trying to get the team to see what you already see without guiding the discussion!

And lastly, and most importantly… please don’t take the “sticky note vote” approach. Assembling 9 or 10 collective ideas on a wall and having everyone voting by placing their post-its with your winners determined by summing up the votes.

That’s what I did… a half day or less on day one, lay out the vision and then get the heck out of the way so the team can execute.


Founder of the align5 Companies,  CEO of Scaling Up Coaches, and Serial Entrepreneur

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