Team Practices Group/Retrospective for playing to win strategy process 2015-2016

TPG's strategy effort from Sept 2015 - March 2016

2016-04-07

What went well
Almost everyone wanted to highlight or discuss (but not necessarily agree with) these points:
 * We understand ourselves and our challenges better
 * learned a lot in a lot of different directions.  deeper shared understanding of each other and the organization.
 * We are more confident in the status quo after bringing up alternatives and systematically shooting them down
 * reason to start process was assumption that what we were doing could be done better, but seem to have disproved that concern.
 * KS: question how systematic it was; we don't know what pieces we're going to pull in
 * We actually talked to our customers
 * We challenged the assumption that we inherently provide value, and came away with a better understanding of how our customers value us
 * GG: We can keep doing that
 * JA Primary source of new data during the strategy process.
 * GG Also CSAT
 * KS: the structure of the process caused us to think differently about what we already knew (a kind of new data)

Half the team wanted to highlight or discuss (but not necessarily agree with) these points: Mentioned but got no further votes for discussion:
 * We observed several angles of our existing status quo
 * We self-organized, like, whoa
 * Regular meetings when we needed them, good checkpoints, slide decks, spreadsheets
 * We built capacity in the team for doing these types of collaborative processes
 * we got feedback from customers
 * I think we uncovered most of the reasonable strategic possibilities
 * We can salvage some ideas from Bumblebees, Swarmers and Agile
 * Kristen (and later Grace) really kept us going and were great stewards
 * Many team members stepped up in many ways to support the process
 * We learned a lot
 * About ourselves, our role, and our customers (and almost about the unserved)
 * With Bumblebees, I feel that I was able to raise my painpoint that verticals still need to talk to infra and that infra needs to talk to each other….unique to me on TPG

What would we wish that we'd done differently (or would do differently in a second round)
Almost everyone wanted to highlight or discuss (but not necessarily agree with) these points:
 * "A strategy" may not have been what we actually needed (rather, maybe it was a revised operating model, a stronger team narrative,....?)
 * maybe we're not actually coming up with a strategy, just figuring out how to organize ourselves
 * in which case, what was/is our strategy?  KL: we focused more on our process/interactions than a strategic choice
 * never quite focused on strategy (vs vision, operations, etc, things adjacent to strategy)
 * Common agreement on what is the problem we are solving
 * AR: thought we had consensus on the strategic process
 * went off the rails on that
 * are we responsible for org maturity or not?
 * Never really had consensus on either one

A majority or half wanted to highlight or discuss (but not necessarily agree with) these points:
 * I was never confident that the WMF situation was stable enough to proceed with long-term strategic planning
 * is it a question of alignment?
 * GG: thought we were in the chaotic domain
 * AR: was thinking of strategy as a way to ground us in chaos
 * The overall person-hours spent felt excessive relative to value gained
 * We got hung up on perfection and semantics a lot
 * General strategy fatigue with strategy conversations happening all over the org but also not feeling a strong sense of alignment with any of them
 * [It might have been better to] Aim to complete the early steps in hours or days, not weeks
 * Agree in advance on the whole P2W structure (e.g. how testing would work)
 * I don't feel confident that we resolved our strategic problem
 * Decision rule was murky
 * We tried to follow the process faithfully rather than shu ha ri
 * (some disagreement to that)
 * We could have had the conversations [with stakeholders] sooner
 * Changing the strategic problem midstream was the right thing to do, but was frustrating
 * It was disappointing that status quo was "the answer" not because it is wrong but because there was a strong sentiment that we would find something better [does this mean something like, "and so picking status quo feels like settling"?]
 * There is a lingering feeling that there may yet be something better

Less than half wanted to highlight or discuss (but not necessarily agree with) these points:
 * IMHO the book was tone deaf to WMF values
 * The article/process was somewhat tone deaf, and the book was way more so
 * I would recommend learning P2W from the article and not even opening the book
 * FYI: Maggie wrote up a rephrasing of P2W in WMF-compatible language
 * Seemed like a predictive and linear (that is to say, waterfall) process designed for the simple domain
 * Strine explained that we made it even more waterfall
 * We didn’t iterate much on ideas
 * The overall calendar time spent felt excessive relative to value gained
 * It was fatiguing to always be in mind/on the calendar
 * Rarely felt like we got to celebrate incremental successes
 * External challenges caused us to have to delay and rework in some cases--just bad timing
 * We spent alot of time on it
 * Be more clear at what steps we could veto options for personal reasons
 * We didn't talk to people who aren't our customers (yet)