The Meeting Most Firms Skip After a Big Win
Sep 21, 2026
In past articles I talked about the virtues of celebrating your wins. Of stepping back and acknowledging that you did a thing, and taking pride in the quality of your work. I remember working at Apple, on the systems team for the iPhone … and all the hundreds of people, if not thousands of people, who worked on the development, stopped what they were doing to watch the announcement.
My team in particular (along with a couple others) would go down to the local Apple store on launch day before they opened. We’d gather outside the store and cheer the customers who waited in line to be the first ones to buy the new phone as they went in and came out. We would celebrate with them. Then we’d go out for breakfast and spend the afternoon celebrating at some company sponsored party.
And I was proud in a way I’d rarely ever been before. Proud of my work. Proud of the product. Proud of the company.
Celebrating wins is important. So is what happens after. The retrospective.
For most small firms, when they settle the case or finish a large project, they immediately turn to what’s next. The next task they’ve been putting off, the next fire that needs to be contained, the next case or project. There’s no time for celebrating, and there’s definitely no time to hold a retrospective.
But what is a retrospective, and why is it so important?
A retrospective is a 30–60-minute meeting where you go through the following basic agenda:
- What were we trying to do, or accomplish?
- What actually happened?
- What was the human cost?
- What went well?
- What went according to plan?
- What didn’t go well?
- Why not and what was in our control?
- What would have to be true to do the same thing again …
- Without the same human cost?
- To make it more ideal?
That question, “What would have to be true…” is such a versatile and powerful question. Looking at the whole though, hopefully you can see the fruit a meeting like this might bear. At Apple it flowed from the bottom up, where the findings of one group’s learnings fed into and supported the next, which all boiled up to the top where decisions and prioritization would flow back down.
To generalize this enough to be relevant to everyone here, most firms have support staff/teams, technical or practitioner staff/teams, and the partners. Support teams include paralegals and assistants in law firms, client service associates and operational staff in financial advisory firms. Practitioners include associate attorneys and senior associates on the law side, and associate and lead advisors on the financial side. And then finally partners are self-explanatory.
Support, practitioner, and partner.
The support teams would get together, go through a 30-minute meeting working through the agenda above, and either submit a report to the practitioner teams, or to the partners directly. Those findings would add context and specificity to the practitioner’s retrospective, which would also be presented to or shared with the partners. And ultimately, the partners would convene and have a comprehensive picture of how their business operated … in addition to their own retrospective findings.
You are the leaders, and this candid feedback is gold.
- Is there alignment and a shared understanding across all teams about what you were trying to accomplish?
- In order to answer whether something went according to plan, each team needs to have a clearly defined plan. If that doesn’t exist, the retrospective will make that clear.
- What held them back? What was within their control and what wasn’t?
- What was actually within your control, but not theirs?
- What do you own?
- What would have to be true for the next time to be better?
- Do they know what better looks like?
- Do they know what good/ideal looks like?
Foundational questions come out of this exercise. The feedback you get, along with your own personal findings, will inform how you identify and prioritize change in your firm.
This is what constant improvement and constant vigilance look like at the biggest companies in the world, and that doesn’t change for your firm or mine.
Do you hold retrospectives? What have you learned? Let me know. Reach out, reply, set up a 1:1 and let’s talk about it.
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