The Monday Morning Test: How to Make a Law Firm Retreat Actually Matter
Retreats are a funny thing in law firms. They’re often the only time in the year when attorneys and business professionals are expected to step away from deadlines, stop multitasking, and actually think together. Retreats are often the only meetings where the participants bill zero hours but still expect a return.
Over the past 10 years, our team has planned, led, and coached firms through retreats of every size and style; from leadership off-sites and partner retreats to marketing/BD team strategy sessions and practice group planning. And this week, we’re heading into our own team retreat, and even for the "experts," the discipline required to make this time valuable is immense.
Here’s the truth: a retreat isn’t successful because people felt energized, laughed at dinner, or said, “We need to do this more often.”
A retreat is successful when it passes what I call the Monday Morning Test:
When your colleagues walk back into the office, do they do anything differently?
If the answer is no, then the retreat was a (well-intentioned) break, not a strategic investment.
If you want to move your firm’s trajectory, you must stop treating your retreats as a vacation or a lecture series and start treating them as an intentional deployment of your most expensive assets: your people.
Part 1: Planning for a Retreat
1) Decide what the retreat is really for and pick one priority
The most expensive mistake a firm can make is a lack of focus. Many firms try to use retreats to do everything at once: strengthen culture, fix communication, identify growth strategies, align leadership, and launch a new initiative.
The outcome? A cloudy agenda, diluted conversations, and little to no follow-through.
Instead, decide on a single goal for the retreat in advance. For example,
Internal culture and cohesion (repairing issues, strengthening relationships, integrating new people)
Aligned processes and structures (billing, timekeeping, onboarding, skills training)
External growth strategy (targeting new industries, expanding practices, sharpening market position)
While all of these priorities matter, most firms can’t meaningfully tackle them in a single retreat without compromising clarity.
If your firm has recently onboarded laterals, hired a large associate class, or added senior business professionals, the best decision may be straightforward: use the retreat to build connections. Sometimes the best use of time together is simply time together.
If the firm is struggling with broken systems, inconsistent billing practices, or uneven training across teams, the retreat may be best spent documenting the operating structure the firm needs next, including repeatable processes, clear ownership, and a practical way to measure adoption.
And if the firm is truly in growth mode, then commit to that focus fully. Structure the retreat around decisions and planning that translate into action: target markets, practice priorities, cross-selling opportunities, key relationship mapping, and actionable next steps with owners and timelines.
2) Build accountability into the agenda, not into good intentions
Retreats create positive feelings. But positive feelings don’t create follow-through.
What creates follow-through is accountability built into the retreat structure:
Make ownership of tasks visible. Professionals will follow through when accountability is public.
Capture commitments in writing and circulate a 1-page recap within 48 hours.
Pre-schedule follow-up meetings to check in on commitments.
Provide simple progress checkpoints between meetings to keep everyone moving forward.
3) Invite the right people
Many retreats default to partner-only attendance, and that’s fine if the retreat's purpose is aligned with that. But firms miss a significant opportunity by excluding or underutilizing their professionals, who often drive execution, culture, and client experience. The firm’s C-suite and leadership, including the COO /Executive Director, CIO, CMBDO, CFO, practice managers, among others, shouldn’t just attend. They should be active participants and, in many cases, lead portions of the retreat with their role-specific data, adding expertise and clarity.
A retreat should never send the message that firm strategy is “attorney-only” while implementation is “someone else’s job.”
Part 2: About to Attend a Retreat
1) The retreat isn’t a spectator sport
You can feel the energy shift in a retreat room the minute people decide they’re going to be passive.
Those who get the most out of retreats aren’t necessarily the loudest voices; they’re the ones who show up prepared and curious.
If you want the retreat to matter, walk in with three things:
One thing your practice/team needs to stop doing
One opportunity you want to explore
One relationship you want to strengthen
That mindset alone changes how you listen and contribute. And will provide you with clear follow-up items regardless of your role in the firm.
2) Don’t worry about the “checked out partner.”
Let’s address the elephant in the room: there is almost always at least one attorney checking email under the table and broadcasting their skepticism through body language. A friend of mine says, “You can’t boil the ocean,” and retreat leaders should take this to heart and avoid obsessing over converting the most disengaged person in the room.
Instead, design for the majority and manage the outliers.:
Use competition as an engagement tool (yes, it works)
Structure shorter working sessions intermingled with time to network/socialize
Create variety in the format: discussion, debate, teams, exercises, and reporting out.
Provide people with meaningful roles for the retreat in advance so they can prepare properly.
Often, the social pressure of a high-energy, competitive environment will eventually pull in any disengaged individuals or at least neutralize their ability to stall the room’s momentum.
3) Swap lectures for workshops
If there’s one format that consistently generates insight, buy-in, and conversation, it’s this: Bring in the voice of the client.
That might include:
A client panel
Anonymized client feedback themes
Additional workshop suggestions include:
An exercise in identifying the most frequent friction points for the firm’s or team’s top 10 clients
An industry targeting map for practice growth
A session dedicated to redesigning the firm’s service-delivery non-negotiables
A strong retreat blends real-world input with “big thinking.” One great exercise is to allow groups to brainstorm marketing and business development-related ideas with an unlimited budget. “If we could do anything for this client/industry, what would it be?” and then have the teams pull the ideas back into realistic initiatives with clear timelines. This allows them to consider what might work with different audiences and then come up with practical ways to do something close to what they were imagining.
That’s when people leave with both inspiration and action.
Part 3: Just Returning from the Retreat
The biggest momentum killer isn’t lack of intelligence or effort.
Instead, people walk back into a mountain of work, and the "retreat goals" are immediately buried.
No intentional follow-up. No reconnecting with the people they bonded with. No time set aside to translate retreat insights into real-world behavior.
A best practice I recommend: block time on the first morning back in the office for retreat-related work. Even 60–90 minutes can change outcomes.
Use that time to:
Capture key commitments
Schedule follow-up meetings
Begin the first deliverable while energy is still high.
How to measure ROI six months later
Managing Partners often ask: “How do we measure whether the retreat worked?”
The right answer depends on what the retreat was designed to accomplish, which is why clarity on purpose matters from the beginning. And if the retreat outputs are not written as a checklist, workflow, or simple playbook, the firm will default to old habits within two weeks.
That said, here are practical ROI indicators:
If the retreat centered on culture/cohesion:
improved lateral integration
retention of key talent
increased cross-practice collaboration
increased participation in internal initiatives
If the retreat focused on processes/structures:
[x] number of processes redesigned and documented
Increase in adoption of the new process.
Improved clarity in roles (who owns, who approves) to reduce confusion and redundant efforts
If the retreat concentrated on growth/market opportunities:
number of new BD initiatives launched
progress on targeted industry/practice growth plans
increase in cross-selling activity
number of proactive client touchpoints completed
I also love measurable “movement” KPIs such as:
Did the follow-up meetings happen?
Did owners complete the tasks by the deadlines?
Did the group produce deliverables (plans, checklists, client maps, BD pipelines)?
Revenue is a lagging indicator, but execution is measurable much sooner.
The Bottom Line
Retreats are among the few moments when firms can step away from the day-to-day and make real decisions about the future, whether that be culture, process, strategy, or growth.
But the real value is what happens on Monday morning.
As my team and I head into our own retreat this week, we are practicing what we preach: we have an agenda, we have a clear focus for the coming year (ahem: client retention and growth), and we have already blocked our calendars for the day we return to our offices.
A retreat is a rare gift of time together. And it isn’t successful because people had fun, felt inspired, or nodded along to a strategy deck. It’s successful when the firm returns to the office and operates differently. That takes focus, honest conversation, clear decisions, and the discipline to assign ownership and follow through after the room clears. The firms that use retreats well don’t treat them like a break from work. They treat them like a blueprint. Monday morning is when the retreat either gains momentum or becomes a memory.
RETREAT CHECKLIST - What to Stop Doing:
To make your next gathering practical and productive, stop doing the following:
Stop letting the loudest or most negative voices take over the room.
If one or two people dominate with cynicism, the retreat turns into a gripe session. Strong facilitation matters as do clear rules of engagement.
Stop talking AT people.
Retreats should create space to think , not just consume information. And if you need four hours of slides for a presentation, what you really need is a different format.
Stop excluding business professionals with specific expertise.
COOs, CMBDOs, CFOs, practice leaders, managers — these individuals help drive implementation and build culture.
Stop designing activities for only one personality type.
A retreat centered on golf, late-night drinks, or physically demanding activities can instantly alienate people. Offer a variety of options for social activities.
Stop keeping the agenda a secret.
If attendees don’t know what’s coming, they can’t prepare. And no one provides their best thinking when they are surprised.