Soul of Startups
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Soul of Startups

There retros, then there are the 10 levels of a DEEP RETRO.

Retrospectives or “retros” are commonplace on agile teams. You can hold a retro to look back on an important day, an event, a week, a month, a quarter, a year, and so on. Generally speaking, the longer the lookback, the longer it takes to do the retro, which makes sense, there’s more content to sift through. But there is another dimension to retros, and that’s DEPTH. Retros can be very quick and stay very surface, they can hit the highlights (as is often the case), or you can mine for deeper insights- figuratively wading into deeper waters in the hopes of finding richer insights.

The quickest retros can be purely verbal, they sound like a closing or a quick reflection. Most retros have something written- I like sticky notes- but the deepest retros can include all kinds of data, anything you want to include in the look back.

The deepest retrospective I was ever a part of was after the 2017 Techstars class. My colleagues and I took structured learning and experimentation as far as we could for that program. Before it started, we created three themes for experiments and ran 4–6 experiments in each theme. We tried new things, edgy things, things that made us feel deeply uncomfortable because we had no idea if they would work. We also wanted the program to incorporate the lean concepts we were teaching companies in the program, we wanted to “drink our own champagne” so to speak and live fully into the values we espoused to our portfolio companies.

We were so alive with our own boundary pushing during that program that when it ended, we needed time and space to dive deep into all the things that happened and how they related to the things we expected to have happen. That’s the learning gap, and we were voraciously learning.

The Deep Retro Completed

Here’s what we did when we committed to doing a Deep Retro:

1) We started with the Timeline Retro format we learned from Zach Nies. On a timeline, we visualize from the beginning of the program through to the end, about a nine month cycle with recruitment, selection and running the program. We then added the important moments and events that stood out.

2) Then we printed and added photos to the retro, taken over the timeline to help us remember and really ground ourselves in what happened. We also added artifacts that were created during the program, whatever was reasonable to bring into the room. Those objects carried a lot of meaning, so we included them in the room.

3) Then we added emotions in a separate color sticky note, as many as we needed to share our inner experience of those events.

4) Given all those moments, memories, artifacts and emotions, we used a different color sticky note to pull out the learnings and implications from the program.

It was a large enough body of work that we each worked independently to make our contributions to the retro. We came back to it over the course of a day or two until we felt pretty complete. We also returned over those couple days to digest what others had added to the retro, taking our time to take in the reflections of others.

Deep Retro Time Lapse, Video by Max Rehkopf

We could have stopped there, but we didn’t. Our coach, mentor and friend Ryan Martens who was supporting all that learning during the program facilitated a conversation that bubbled up the top things we wanted to get out of the retro. We spent about 90 minutes talking together about our reflections. These exercises took the retro to a whole other level.

5) We split the the program experience into 3 or 4 roughly equal time periods. Then we did a Four L’s retro on each time period after walking the wall to review it. The four Ls are Loved (or Liked), Learned, Lacked, and Longed For.

4Ls Retro on the Retro

6) Then we voted on the things in the 4Ls that were most important to carry forward. The voting was important for helping us focus on what mattered most for the next program.

We could have stopped there, but we wanted to go deeper into the learnings and implications we were unearthing in the retro process, and our facilitator led us deeper into the retro.

7) We divided all the implications into five buckets relevant to the program: Companies, Teams & Programs, Mentors, Techstars and Other as a catch-all. Looking back at the timeline retro and the 4Ls, we took some time to silently generate implications and then we shared them with the group. Then we voted, five dots per person on which implications we felt were most important.

Diverging on Possible Implications

8) Given those implications, we then generated a list of possible decisions. All of them were possible answers to the question, “This being so, so what?” It was the moment we moved out of a retro and into casting forward potential futures.

9) We did a little more work on mapping our top implications to the possible decisions we could make. We pulled the implication sticky notes onto a new page, taking only the ones we voted on. Then we pulled over our possible decisions and drew lines between them. It helped us recognize if we had any top implications that had no corresponding actions and vice versa. We allowed for some overlap, and we were confident that the decisions we wanted to make next were deeply linked to the most important implications from the work of the prior nine months.

Mapping Top Implications to Decisions

We could have stopped there, but there was one more exercise that squeezed the last hidden insights from the team.

10) We passed the talking stick (I think it was a dry erase marker) from person to person in a circle saying the most controversial thing you could think of until everyone passed. A couple of big truths or big possibilities were uncovered in that process. I remember feeling excited and terrified to do it, and this was a team with very high levels of trust. The window of tolerance for truth telling was wide.

Once the conversation was done, we took pictures and took everything down. We wrote up some of the things we took away from the timeline, the 4Ls, Implications, Decisions and the Pass the Pen and kept them with us as we thought about the following year. We also allowed ourselves some time to mull over everything we had talked about.

I’m so grateful looking back on the experience that we really dug into our own highest learning potential. It served us as leaders and investors not to mention the programs we ran in the future. It’s available to you too, there are so many kinds of retros, the Deep Retro takes the most time, but it is also the richest!




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Julie Penner

Julie Penner

Founder and author of Soul of Startups and #Ruleof5. Venture Partner at Frazier Group. EIR at Telluride Venture Network. Coach. Facilitator. Challenger.

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