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126: How We Ran Our 2-Day Strategy Sprint (with Template)

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This week’s episode comes fresh off the heels of a two-day strategy sprint that my team and I ran to tackle our biggest business frogs. 

One commitment we made at the end was to “share truth while it's fresh” — with delightful specificity and crazy-smart systems — so that’s what I’m doing! This is a behind-the-scenes peek at what we're building (and how) during my “JB 3.0 Business Renaissance,” in as real-time as we can.

I also want to give a shout out to my she-probably-has-no-clue-I-exist-yet-but-hopefully-someday-friendtor Amy Porterfield, an online marketing pro and absolutely fantastic teacher. We haven't met yet, but I have been mega-binging on her podcasts, and I was inspired to do our strategy sprint by her recent episode #222 on creating a weekend immersion retreat.

The fix-it ideas from Amy’s podcast got my wheels turning, but for this round I pivoted our focus toward tackling the biggest, most strategic projects. In the episode, I share all the details on how we designed the sprint, how we prepared in the days and weeks leading up to it, the exact flow/schedule we followed, what worked best, and what we would do differently next time. 

If you want to run your own two-day strategy sprint, enter your information below to get the free template we created from our own planning docs — which will be helpful even if you decide do to this solo!

In This Episode:

  • [11:01] The goals of our 2-day strategy sprint: get the biggest frogs from zero to done in two days.

  • [12:26] The five questions Amy Porterfield asks before her weekend business immersion retreat: What's your number-one pain point in your business right now? What feels messy, broken, or painfully slow? What needs to be fixed before you can grow? Where are you losing money? What have you been putting off for way too long?

  • [13:32] Stephanie and Marisol were with me for the 2-day strategy sprint. We first had a couple of alignment calls to fill in the big picture, then five or six sprint windows spread out over the two days and smaller discrete projects for each sprint window. 

  • [15:05] Part of the J.B.E. 3.0, as I head into year nine of running my own business, is continuing to scale my streams of solopreneur income.

  • [15:48] Leading up to the strategy sprint, we spent time defining the Pivot environment of ideal community members. I also did a lot of work before the strategy session, since I knew it was coming up.

  • [16:36] The four types of Pivot community members: pivoters, solopreneurs, managers, HRBPs

  • [20:16] Breakdown of how we actually spent the two days (with a surprise at the end)

  • [27:38] I converted to an S Corp this year, and put myself on salary (along with paying 3-5 contractors on a regular basis). It really puts the "plus" in solopluspreneur.

  • [27:59] Costs of the strategy sprint, why I believe making a bet on ourselves does pay off. 

  • [28:35] I'm also taking a page from the Basecamp founders. The entire team gets a bonus if we have year-over-year growth in the business.

  • [30:20] I was so excited at the end of the day, I couldn't sleep. My brain was on fire it was unbelievable how energetic I felt when it was time to go to bed!

  • [33:03] How we conducted midpoint check-ins and end of day reflections

  • [33:36] With the template above, you also get the road map and the action item capture sheet and printing them was really helpful too.

  • [34:33] The sprint is about the big projects, but you need to note the dependencies that have to happen to get there.

  • [34:47] The INFJ friendly surprise at the end for us to retreat, recharge, and relax. 

  • [36:49] What we’ll do differently next time, and what we’ll build into our ongoing rotation moving forward

Have a question related to this episode? Ask away here, in a quick voice note. We look forward to rolling all of your questions together and creating a listener Q&A show soon :) Read the full transcript here.

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