Kevin Keane, Co-Founder and Executive Director of Directed Action Inc.
A few weeks ago I attended a Board retreat for TASC, an organization that works with middle schoolers, high schoolers and administrators to develop moral leaders who positively impact the world. As you might expect, the Board members are passionate servant leaders themselves. I was surrounded by accomplished executives and administrators who care passionately about TASC’s mission and vision. As the tagline of the organization says, we all want to “Be the Change.”
As we hashed out marketing, partnerships, and operations, it was work, without a doubt. At the same time, it was energizing to know that the work was leading to a vision and mission we all share. Sharing those values provided a foundation that brought leaders with different skills and perspectives to trust and make space for each other.
Shared values alone do not translate to action or progress within an organization. The saying goes that, “The road to Hell is paved with good intentions.” I could just as easily say it is paved with people getting “buy in” from within an echo chamber. Who has not been in a meeting where everyone was saying the same thing at each other ad infinitum?
At TASC, however, with that foundation in place, we were then able to work through the agenda in such a way that leveraged our functions as Board members. One of the staff members said that in previous retreats, they left with the heavy feeling of all the tasks that awaited them afterward. At this meeting, in contrast, they felt energized and motivated.
I am fascinated by all the things that go into these meetings, the levers to turn and flips to switch that can make a meeting successful or unsuccessful, productive or deadly. For example, a room that is top heavy with senior leadership can result in a lot of talk and no action. A room without a decision maker can end up with every participant in their own personal weed garden.
Inspired by this experience, I wanted to make a note of different factors that go into maximizing the brilliance you get from your team.
Retreats vs. Meetings
Zoom Fatigue is real. Bringing the workforce online has very real benefits but also downsides. The digital connections that have allowed us to continue to work throughout a global pandemic have offered real rewards in terms of productivity. And they offer real downsides in terms of energy, and well, fun.
When considering ways to engage your team, your stakeholders or your executives think about what you want to get from your team, what you need to get from your team, and how best to get it.
Some reasons to have a retreat include:
Big idea, high level strategy discussions. This is not a longer weekly meeting to check in on tasks and deliverables. When you have major decisions, paths to take, new products to develop or a new path for your team or company, that’s when it’s time to think about a retreat.
Breaking down bottlenecks. This is an opportunity to create real connections in your team. A retreat should fortify the work your team members do together but should not be just getting work done. The idea here is that you want team members to rely on one another and, as a leader, not have everything go through you.
Introducing new team members who have not yet met in person (or haven’t spent a lot of time together). Some of your team members may never meet in person, which is OK. But bringing people together in person, to get to know each other can enhance their working synergies.
Building trust and camaraderie given the realities of the new workforce. This goes hand in hand with the second bullet. Because tone is hard to read in short written texts like emails, chats, or slacks, personality differences can cause division and tensions can run high. Seeing each other as people, as opposed to another box in a zoom can ease those tensions.
Recognizing great achievements and celebrating. As I mentioned before, while business leaders were able to figure out productivity online, we’ve had a lot harder time figuring out fun. You can celebrate major milestones – most sales, most new customers or simply getting through a difficult work time – most gregarious cat, best work pajamas. Fun can lead to a more productive work environment.
How often should we do this?
Retreats should be one or two times a year. They should be scheduled such that they allow for an actual retreat from, or release of, work. If they are too frequent, you can lose the engagement and innovation that comes from doing something “new.” If they never happen, some challenges will become too large to address at a retreat and may sabotage the endeavor before you get started.
Some ways to make sure that works for you:
Try to get everyone in person if possible. If you have team members that get energy from other people, then online meetings are not a substitute. At the same time, be mindful of schedules, caregiving, and the real challenges people are facing and try to be flexible when you can.
Be present. If you expect your team to leave their busy lives, families, friends, hobbies, and volunteer work for a day or more, as a leader you need to model being mindful and present. See below about scheduling the timing appropriately. There’s no point in having long structured days if everyone, including you, is going to be on their phones the whole time.
Reschedule regular meetings. Building on the point above, keep the entire schedule free of task oriented work and focus on the big picture. The idea is not to be filling time in between work but clearing schedules and freeing everyone’s mind to think broadly and bring new ideas.
Hmm, I’m not sure if we need a retreat – should this just be a meeting?
Maybe! But given the very real effect that zoom meetings or in person meetings are having on your team, do you need another meeting or can it be an email? Are meetings actually hindering productivity and you need to look harder at your processes? All this is part of a larger project of looking into your operational excellence and how your operations are driving or obstructing your goals.
A three-hour tour: The Gilligan’s Island Retreat
A friend of mine described a work retreat where one of the team members took the other team members sailing. The idea was that the team would spend a gorgeous day on the water with people working as a team on something very concrete. The team members could accomplish something small to lay the foundation for the trust and connectivity necessary to attack big goals.
It didn’t go that way.
The day was chillier than most people expected. Most of the small team were not sailors and did not account for the fact that it’s always a little colder in the wind on the water. The team lead immediately got seasick and spent the entire trip throwing up below deck. The sailor picked one of the team members with some sailing experience to help but failed to tell them to hold on to the line when they turned, or “tacked”. They let go of the line which immediately got caught in the propeller. Cold, tired, and utterly defeated, the team needed to be rescued by another boat and towed in.
Rather than being a way to build up the team, getting stranded and seasick left them with grudges more firmly entrenched.
How should I structure my retreat?
How do you avoid a similar fate? Once you’ve decided that a retreat is the way to go to accomplish your goals it’s important to consider the location, the format, and the attendees. Keep all those elements in focus while driving toward accomplishing your objectives.
When you’re considering a location for your retreat, consider the following:
Budget. Just because you cannot take your entire team on an all expenses paid trip to New Zealand doesn’t mean that a retreat can’t happen. Depending on the size of your team or your objectives, a day or even half day can be enough to achieve your objectives.
Time. You will investigate your budget for the cost of travel, food, and entertainment for your team. At the same time, be realistic about your time budget for your activities. You may feel that you want three days but be conscious of the opportunity cost for your employees. They may be client work, yes, but they may also be missing soccer games, birthdays, and anniversaries. One women’s business conference I’m familiar with consistently scheduled their dates to fall over Father’s Day. Even if you could estimate that not many of the women business owners are fathers, they all had fathers in their lives, not to mention the corporate sponsors and other stakeholders who had to make a hard choice around that time.
Team preference. Looking back to the story above, take into account what you want to accomplish and whether or not that fits in with your team. Don’t try to introduce people to an activity that is too challenging or far outside their comfort zones. At best, they disengage. At worst, it will only widen the divisions among the group.
Your agenda. Just as you don’t want work competing with the connections you are making on your retreat, you also don’t want to overstuff your agenda with team building or ideating. You want to strike a balance between developing your strategy, allowing your team to engage with it and each other, and unstructured activities.
It’s not all trust falls. We all know the cliche of the trust falls, the ice breakers and like the Gilligan’s island scenario described above, all the different ways that thinking “outside the box” when it comes to office engagement can go awry. You don’t have to go too far outside the box and feats of strength do not make a successful retreat. Know when less is more.
What does success look like?
Success will be different for groups where you’re bringing diverse leaders together but there are some elements that stand out in a great retreat, like the one I describe with TASC, and some elements that define a retreat that would be better skipped, like the three-hour tour. Not every element of your day has to go perfectly. In fact, keeping things a little fluid for spontaneity or bloopers can bring people closer together. As long as you keep an eye on your objectives in holding and structuring the retreat, you can be confident that you’ll meet them.
Some tips for measuring success:
Does everyone know why we held the retreat? Going back to your reasons for having the retreat, make sure everyone understands why they were there and why their contribution was important. Build in time to get real time feedback on this part.