Measure Twice, Cut Once: Join Momentum Day

“We will just squeeze quarterly planning in tomorrow afternoon,” said my boss.

I looked at him, trying not to show my astonishment. We were running the marketing for a fast-growing tech startup. We had millions of dollars in investor cash, but it was being spent faster than we were bringing in new customers.

There were strategic questions that hadn’t been answered about our product. Sales and marketing weren’t aligned on what to say about the product features. We had ad spend that wasn’t showing positive ROI, and we had new teammates just getting up to speed.

Our planning session amounted to a few hours of our boss asking us to sign up for various projects. There was little reflection on what had worked (or not worked) recently, and no questions about strategic level ideas. Our quarterly planning didn’t effectively map out what the next 12 weeks were going to look like, or what it was, exactly, that we wanted to accomplish.

You can imagine my frustration when “squeezing in” the quarterly planning was more of an afterthought than a dedicated time to really think about where we wanted to go.

Measure Twice, Cut Once

My stepdad was great at construction. He could build or rebuild anything, seemingly able to envision the way things fit together in his brain before he had them in his hands. Even so, every time I helped him build anything he would say, “measure twice, cut once.” I can still hear the click of the tape measure.

In my time as a founder, then freelancer, I always took a full day to do quarterly planning myself before working with my own team on their quarterly plan. Yes, it’s time-consuming. But it matters.

When I do my quarterly plan, I get clarity around where I want my revenue to come from, how I’m going to do it, and what resources I’m going to need. Plans rarely go the way I project them, but the act of reflection and study helps me react better when plans change.

That’s what our coming Momentum Day is all about: getting clarity around your upcoming quarter. Reflect on what happened over the previous quarter (or year), talk it through with some smart folks, and figure out what to do next.

I hope you’ll join us for Momentum Day on Saturday, May 15. If planning gives you anxiety or frustrates you, I want you to know that you’re not alone. Planning is the act of choosing to let things go and deciding where to put your attention. That means a certain amount of grief, big or small.

If you’re going to go through the process, you might as well do it with a group of business owners and leaders who will have your back and be supportive. We’d love to have you with us on May 15 as you design your next 12 weeks.