A while back, a lawyer named Mike sent me a question. Mike works at a nine-attorney business law firm, the kind of regional practice that helps local companies with whatever legal issues come their way. He’d been using Kanban in his own practice for a while and liked the results. His problem was getting anyone else on board. In his words, there was pushback “whenever the staff needs to have another account or learn some other piece of software.” He also mentioned that the firm doesn’t have much turnover, which is a good thing, and also means the team’s habits can run deep (including bad ones).
Mike’s problem is common. Many firms are adding tools and processes faster than their teams can absorb them, and it’s the staff who have to learn each new system.
The common instinct in a firm Mike’s size is for partners or management to pick the tool, decide how it will be used, and roll it out to the team. Many firms have always handled change, and it tends to produce the kind of pushback Mike described. Peter Senge, whose book The Fifth Discipline helped put organizational learning on the map for business leaders, put it this way: “People don’t resist change. They resist being changed.” Your team will be far more open to changes that fix problems they deal with every day, especially when they helped pick the fix.
That applies to the changes your firm is already in the middle of, too: the half-adopted tool, or the improvement idea someone floated six months ago that never went anywhere. Each of those needs a place where the team can talk honestly about how it’s going, and my favorite tool for that is the retrospective.
What a retrospective is
A retrospective is a meeting where your team sets the client work aside for a bit and looks at how the work gets done: your processes, your tools, the way you hand things off and communicate. The goal is to come away with a few concrete ideas for working better together, instead of critiquing individual pieces of work.
If you’ve ever debriefed with a colleague after a trial or a big closing, you already know the instinct. Better if that debrief was formal, but even the ones done over a drink can be useful. Other professions have made it standard practice, from sports teams reviewing game film to military after-action reviews to the morbidity and mortality conferences hospitals hold after a case goes badly. A retrospective takes that instinct and points it at your team and its systems.
It’s also a core practice of continuous improvement, and a practical way for a firm to become a learning organization.[^1]
Why it works
Retrospectives work for two reasons: they create a feedback loop, and they carve out time to work on the business instead of just in it.[^2]
In my experience, many legal teams run without much of a feedback loop. Work comes in, work goes out, and the only time anyone examines how it went is when something goes badly wrong. By then, the conversation tends to be about blame instead of improvement. A regular retrospective gives the team a scheduled, low-stakes moment to notice what’s working and what isn’t while the problems are still small enough to fix. It’s also where you fix your other meetings: the standup that runs long, the case review nobody prepares for.
The second reason is about time. Law practice runs on deadlines, and deadlines feed what Charles Hummel called the tyranny of the urgent.[^3] Important-but-not-urgent work (like fixing the process that keeps generating fire drills) gets pushed aside by whatever is burning today, which is how teams end up fighting fires instead of preventing them. A retrospective gives improvement work a protected slot on the calendar, so it doesn’t have to compete with the day’s emergencies.
Setting the right structure
Structure still matters, though. Without it, a retrospective can slide into a gripe session. My usual first retrospective asks three questions: what’s going well that we should keep, what isn’t working that we should stop or change, and what we should try. Here’s what I’d put in place around them.
Invite the whole team. Include more than the lawyers. Your paralegals and assistants are closest to the day-to-day execution of the work, and they often see problems the attorneys don’t.
Create the right space. A conference room with a whiteboard and a stack of sticky notes works, as does a shared online whiteboard if you’re remote. In person, I bring sticky notes and Sharpies on purpose: a three-inch square and a fat marker keep people out of the weeds. (Left to their own devices, lawyers will write a brief on anything.) Online whiteboards have digital sticky notes; keep them small for the same reason. More important than the physical setup is the feel of the room: people need to believe they can be candid without it coming back to bite them.
Designate a facilitator. Someone has to keep time, keep the conversation moving, and make sure every voice gets heard. More on why that’s harder than it sounds below.
Write first, talk second. For each question, everyone gets a couple of minutes to write their answers silently, one idea per sticky note, before anyone speaks. (In person, I like an old-fashioned hourglass for this. We have enough screens in our lives. Online, any shared timer will do.) If you go straight to open discussion, the first idea someone shouts out tends to become the topic, and the rest never get generated. Worse, once a partner weighs in, everyone else tends to fall in line. Silent writing puts every person on equal footing.
Start with what’s going well. It feels good, and it builds enough trust for people to be honest when you get to what isn’t.
Group the answers out loud. As people read their notes and put them on the wall, similar answers get clustered together. Watching those clusters form shows people that nobody is on an island, and it tends to surface problems people have been living with but haven’t felt comfortable raising.
Ask what to try. The last question invites ideas for change, including ideas already underway and ones people have been sitting on. I usually tell the room they have permission, but not a mandate, to share something they haven’t brought up before.
The format matters less than the habit
That’s keep, stop, try, but there are dozens of retrospective formats out there; most of them work well, and changing up the format can be refreshing. A few others:
- Start / Stop / Continue. A close cousin of keep, stop, try.
- Rose / Thorn / Bud. What’s blooming, what’s prickly, and what has potential.
- Mad / Sad / Glad. Leads with how people feel, which can help when morale is an issue or deep-seated problems are surfacing.
- 4Ls. What we Liked, Learned, Lacked, and Longed for.
- Starfish. Keep doing, do more of, do less of, start doing, stop doing. A bit finer-grained than the three-question versions.
- DAKI. Drop, Add, Keep, Improve.
Pick one that fits your team and start.
How often
In a perfect world, I’d have teams run a retrospective every month. Quarterly is acceptable, and six a year is a good compromise. But I don’t demand perfection, and neither should you. A team that holds retrospectives at any cadence is far better off than one that doesn’t hold them at all.
Frequency does change what you get out of them, though. Infrequent retrospectives tend to stay high-level, because there’s a lot of ground to cover. They also run longer, especially for bigger teams; I usually plan about 90 minutes for a team’s first one. More frequent retrospectives can be shorter (a nimble team that meets monthly can often finish in 30 to 45 minutes), and they tend to get more detailed, because the team can drill into specific problems and work on greater improvements.
Getting to takeaways
The point of all those sticky notes is to come away with a few things to actually do. I like dot voting for this (everyone gets a few votes to place on the ideas they think matter most), but sometimes a team reaches consensus on its own, and that’s fine too. The goal is good takeaways without getting overly prescriptive about how you arrive at them.
Ideally, each takeaway becomes an experiment with an owner and, if you’re using a system like GreenLine, a card on the board so it gets tracked like any other work. Don’t expect your team to be great at that follow-through right away. It’s part of what they’ll learn, and they’ll get better at it with practice. This is another argument for more frequent retros: when the next one is only a month out, good ideas have less time to stall.
The facilitation problem (and where GreenLine comes in)
Facilitating a retrospective is a skill, and it’s hard for a team to run one well on its own, especially at first. Every team carries history: relationships, roles, titles, and hierarchies that shape who feels free to say what. When the managing partner runs the meeting, the managing partner is still the boss.
An outside facilitator lets the leader participate as a member of the team instead of running the show, which is valuable for the team and, frankly, for the leader too. When I facilitate, I usually ask leaders to share their answers last or close to last, so they don’t steer everyone else’s.
If outside help isn’t available, here are some options to consider: borrow a facilitator from a peer firm, a bar group, or a coach (and offer to return the favor), or rotate the role among your own team so it doesn’t settle into one person’s agenda.
It’s also why we now include a facilitated retrospective as part of GreenLine onboarding. Once a team has finished its initial onboarding sessions and has been using the tool for a while (usually somewhere between 60 and 180 days in, depending on the team), one of our trained facilitators runs a remote retrospective with them. It’s geared toward how GreenLine adoption is going, but it isn’t limited to that; anything about how the team works is fair game. And it’s designed to model the structure so the team can keep running its own retrospectives on whatever cadence works for them.
We built GreenLine to help legal teams build healthier habits, and a regular retrospective is at the top of my list of healthy habits.
Do one, commit to the next
Back to Mike. My advice to him was to engage his team around the problems they were experiencing and let the improvements grow from there. A retrospective is a good place to start that conversation.
So here’s my ask. Start with keep, stop, try, and set aside time for your team to talk about how the work is going. Before everyone leaves the room, put the next one on the calendar. Then build from there.
