I was talking with a colleague the other day who said that in her experience, management retreats usually ended up at one of two extremes: either they were stellar and everyone loved them, or they were a disaster and people ended up quitting at the end. That may be a bit of an exaggeration—I’m sure many management retreats are more middle of the road—but it reflects a general fear among senior managers that management retreats are inherently dangerous, because they could do more harm than good.

And that’s a legitimate fear. No matter what size your organization, if you take your most senior managers away from the office for an entire day (or more), that’s a significant investment in time/attention alone, not to mention the cost of an off-site facility and a facilitator. But despite these high stakes, many retreats fail, and I think I know the reason why: lazy design.

For some reason, leaders tend to fall back on standard agendas for their retreats, with a couple of strategic topics and probably something “fun” to check the teambuilding box. This is not good enough, folks. You wouldn’t spend $750,000 on a custom home and tell the homebuilder you just need a couple of bedrooms and a couple of baths. You’d be clear and intentional about your design, and you should do the same with your management retreats. Don’t schedule the retreat unless you’ve worked on the following areas:

Sharpen the purpose. Remember, form follows function. Management retreats should always start with a clear purpose, because that’s the only way to determine if you need a retreat in the first place. If all you want to do is cover a couple of strategic topics, then you could probably do that in a one or two extended meetings in the office. But if you really want to dream about the future—to explore ideas that haven’t been explored before—then it makes sense to allocate more time to the conversation, and to be away from the office where you tend to get drawn into the here and now more easily. Start by sharpening the goals and outcomes of your retreat, and then move to working on the process for getting there.

Prioritize action planning. One of the biggest complaints about retreats is that we do them, and then nothing changes. That’s often because we don’t spend enough time during the retreat focusing on what we are going to do differently when we get back. I use a rule I learned from my conflict resolution days—spend one-third of the time during a conflict workshop on “re-entry,” or what the parties will do once they get back into their communities. If you have one day for a retreat, that means you probably need 2 hours on what’s going to happen when you get back. And that means you have to be much more efficient and clear in your “what are the issues” conversation. If that ends up taking all day, then you’ve blown it.

Create a safe space. Retreats are designed to enable conversations you can’t have in the office, which means you need to create the right amount of psychological safety for those conversations to happen. This is one reason leaders have a facilitator—if the boss facilitates the retreat, you’re less likely to have people take risks or push envelopes in the conversation. But even without a facilitator, make sure you set clear expectations prior to the retreat, including adopting groundrules during the retreat that you are willing to enforce.

If you are disciplined about the design of your retreat, you will greatly improve its chances for success. If you want help with designing or facilitating a senior management retreat, just let me know!

Photo by Nathan Dumlao on Unsplash

Jamie Notter