We just got back from our KSB summer retreat, and honestly? We're fired up. Every year we do this twice, once in the winter, once in the summer. And every year it reminds us why we started this firm in the first place.
We know what you might be thinking: a whole-office retreat, twice a year? Yes. Whole office. Every single person. Not just the attorneys while the administrative staff holds down the fort back home. Everyone. Because continuous improvement isn't a department at KSB, it's baked into who we are. Law firms that leave people behind for retreats, or skip them entirely to protect billable hours, are missing the point. You can't build a great team in pieces.
Here's how ours work: the winter retreat is our end-of-year after-action report. We pull the numbers, look hard at what worked and what didn't, and set the table for the year ahead. We plan for the fiscal year ahead. The summer retreat is our check-in — are we on track? What's changed? What do our clients need that we haven't figured out yet? We plan for the school year ahead. In this way, we’re a lot like boards and administrators who orient themselves in January and plan for the school year during the summer.
And here's the thing our retreats keep reminding us: growth isn't just about adding clients. It's about going deeper, not just wider.
For us, that means constantly asking what we can do for the schools we serve — before they even know they need it. Policy services. Webinars. Superintendent and building administrator evaluations. In-person workshops. The goal isn't to be a firm that schools call when something goes wrong (and hope it’s bad enough to make a living). It's to be a firm that helps schools build the kind of governance and policy infrastructure that keeps things from going wrong in the first place. The retreat is where we hold ourselves accountable to that vision. Some conversations are difficult. Some are celebrations. They’re all necessary.
Okay, But What About Your Board's Retreat?
All of this got us thinking about school board retreats — because the same tension exists there.
A board retreat can feel like a massive investment. You're pulling elected officials and administrators out of their regular lives, possibly paying for a facilitator. And if you're not careful, you walk out with nothing but a very long to-do list, a vague sense of optimism, and a blurry “vision” that fades by October.
So what makes a board retreat actually worth it?
The goal is a strategic plan everyone actually believes in. This sounds obvious, but it's the most common place things go sideways. A strategic plan that lives in a binder on a shelf isn't a strategic plan, it's a document. A real strategic plan is one that every board member and every administrator can speak to, in their own words, without looking it up. If you can't get there, the retreat is actually a great place to build that shared language. What are we here to do? What does success look like in three years? What would have to be true for us to get there? Those questions, asked together, are worth more than any consultant's slide deck. They all precede the written artifact, but that is where the magic happens.
Don't let the retreat become a complaint session. Every board has things that aren't working. A retreat is a good time to name them, but only if you're also naming the path forward. Facilitated well, a retreat surfaces the right issues and builds consensus around solutions. Facilitated poorly, it's a day of venting with a nice lunch.
Build in some reflection, not just planning. What did we do well this year? Where did we fall short, and why? Boards that skip the retrospective part and go straight to goals tend to repeat the same mistakes in fancier language.
Don't Leave Without Scheduling the Board Self-Evaluation
Here's something that often gets agreed to at a retreat and then quietly slips off the calendar: the board self-evaluation.
At this point in the year, most boards are wrapping up their fiscal year and heading into a new one. The retreat is a natural moment to commit — out loud, with a date on the calendar — to evaluating how the board is functioning as a governance body. Are we staying in our lane — policy and oversight — and letting the superintendent lead? Are we unified in public even when we disagree in the boardroom? Are we making decisions based on data, or based on whoever was loudest at the last community meeting?
Board self-evaluation doesn't have to be painful. Done right, it's actually energizing — because most board members want to be effective. They just don't always have a structured way to talk about it. The retreat is the right moment to agree that you'll create that structure, pick a date in the fall, and assign someone to own it.
Whether you use a formal instrument or a facilitated conversation, the questions are the same: What are we doing well? What do we want to do better? And how will we hold ourselves accountable?
The retreat plants the flag. The self-evaluation, done a few months later, tells you whether you are on track. It’s also a place to make sure fundamental governance responsibilities that aren’t listed on the strategic plan continue to improve or at least hold steady. Because a well-done plan can’t include everything. Maybe your board has always done a great job being present at school events. Did that continue even though your primary strategic initiatives are to increase staff retention and improve student attendance?
At KSB, we'll be back in the room together in the winter to answer those same questions for ourselves. We think that's what it takes to keep getting better — and we think your board is worth the same investment.
We can even check and see if Bobby’s mom can make it to give your team haircuts.
*Schedule a demo of the evaluation platform at https://www.ksbschoollaw.com/evaluation-platform or email ksb@ksbschoollaw.com.*