The toughest question you will ever ask your team

Our leadership is embarking on one of those super snoozy, but seemingly required business necessities…Strategic Planning.

I hate that term. I used to work for a huge, diversified energy company and our team was responsible for assembling The Board Deck—an exercise in over-compensating a lack of insight with an avalanche of information. They called this Strategic Planning.

Earlier this week we dug in for a half-day meeting with one of our strategic advisors, a retired tech entrepreneur who has seen it all and whom I trust implicitly. We’ll call him Tom (that’s actually his name).

In the weeks leading up to the meeting, Tom peppered us with “homework” and we felt nothing short of obligated to come prepared for a rich, if not purpose-unclear, discussion. Of the many questions Tom asked us to contemplate, one stuck out and was by far the most difficult to address:

What truth does Nutshell see that others do not see?

Truth is a tough word. And how about trying to actually identify what you know that others don’t! Initially we were completely stuck.

We went around the room and weighed and counter-weighed each and everyone’s proposal. We were delighted and surprised by all we came up with and mostly we were very excited by what we eventually co-created.

Here is what Nutshell knows to be true:

Small businesses want to take advantage of the high-quality software solutions that the cloud provides. That means they need to be able to take individual systems that are really good at doing specific tasks and bring them together seamlessly. Nutshell provides this experience by allowing the entire company to collaborate on the sales effort. We’re sort of the Main Street for your company.

So, what truth do you know and how is your company solving it? It’s an absolutely insane question, but surprisingly cuts through it all so you quickly arrive at what matters most to you and your customers.

And by the way, your truth can and probably will change. In fact, I think Facebook nailed it in their Little Red Book:

“There is no point in having a 5-year plan in this industry. With each step forward, the landscape you’re walking on changes. So we have a pretty good idea of where we want to be in six months, and where we want to be in 30 years. And every six months, we take another look at where we want to be in 30 years to plan out the next six months.”

I like that.

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