Your next staff retreat shouldn’t be a one-off event

When the entire staff at Literacy Pittsburgh came together for their semi-annual all-staff retreat, the agenda was no surprise to anyone. CEO Carey Harris and her leadership team had been preparing for it ever since the last staff retreat wrapped up six months before.

For anyone attending, the through-line was easy to see. Instead of a single moment in time, the retreat felt like part of an ongoing conversation: here’s where we were, here’s where we are today, and here’s where we’re going. It was a backstop for getting big things done, a chance to learn together about where the organization stands, and a look six months ahead to where the team wants to be when it meets again. The day even included time to start on some of the big milestones planned for the next six months.

The goals of that summer retreat were the same ones that guided the winter retreat: connect, learn, and align. That consistency made planning easier and helped people know what to expect and how to prepare. Even the staff preread, a summary of organizational progress based on consistent metrics, was familiar, because it was an updated version of the last one.

The retreat wasn’t perfect, and that’s part of the point. When a retreat is part of an ongoing process, it’s less about planning a perfect event and more about making progress together on the bigger journey.

Making retreats part of an ongoing process

It wasn’t always this way. Like many organizations, Literacy Pittsburgh had many of the right pieces in place. They had a clear vision and strategic direction. They did good goal setting at the department level, and they had planned productive staff retreats on their own.

But something was missing. The pieces weren’t working together as one connected process, and both leadership and all-staff retreats were often planned down to the wire, without confidence that the time was being used as well as it could be. Meanwhile, the organization had taken on a bold agenda that would require strong alignment, all while growing and adding to the team. Strengthening the process had become essential.

Tying the leadership and all-staff retreats together into one process changed that. Between the semi-annual staff retreats, the leadership team now holds three retreats of its own to make sure the big goals set with the whole team are moving. Those agendas are no mystery either: there is always time for trust and relationship building, always some shared learning, and always a dedicated work session on strategic priorities.

Together, these sessions form an ongoing process that helps the organization navigate and course-correct toward its big goals. It’s navigational leadership built into the calendar.

What a mature cycle looks like

Joyful Reading Co., which began as Zoobean, the company behind the Beanstack reading platform, has the most mature team alignment and performance cycle of any organization we’ve worked with. With many semi-annual cycles behind them, their progress metrics now tell a longitudinal story that makes it easier to see where attention is needed. Retreats create shared context for better decisions over the next six months. Over time, the team has folded in individual performance management and culture tools, like employee engagement surveys, all serving the same goal: helping the team align and perform together.

The elements of a team alignment and performance cycle

The specifics vary, but every cycle we build shares a few elements.

Semi-annual staff retreats

Every six months, the whole team comes together around three goals: connect with one another outside day-to-day tasks, learn about organizational progress, and align on goals for the next six months.

Interim checkpoints

Leadership checkpoints between retreats make space for problem solving and keep progress toward six-month goals on track, so there’s no last-minute race before the next retreat.

A metrics-focused preread

Before each retreat, a written summary of progress against agreed measures, often organized around our Success and Sustainability Framework. Over time it shows trends; early on it describes the current state.

Contextual priorities

Each six months brings its own priorities, like a major grant opportunity or a new management structure, woven into the retreats and checkpoints so everything connects.

What we learned from retreats that didn’t work

This approach grew out of a number of disconnected, one-off retreats that left us unsatisfied. Like many people, we had planned leadership and staff retreats that felt like separate events. Because each one had different goals and a different format, teams never learned what to expect, so they never quite knew how to prepare or how to make the most of the time. There were great sessions and big misses, and none seemed to build on the last. Every session was a moment in time.

Those experiences reinforced the value of placing staff and leadership retreats inside an ongoing cycle. A retreat works best as the culmination of a cycle: the moment the past months’ work gets reviewed, decisions get made, and the next cycle begins.

Connecting your next retreat to an ongoing process

Process is one of the four domains of team performance for a reason. Effective leaders map out a process for getting from where they are to where they want to be, and align the resources and capacity to carry it out.

So don’t let your next retreat be a one-off. It takes some work to design and stand up a purposeful cycle of retreats and checkpoints, but it gives your team something most retreats can’t: momentum that lasts beyond the day.