Caravanning (and Other Leadership Adventures)

More than a few times in my life, I've been part of a caravan (a group all headed in the same direction in their automobiles to the same place and wanting to do that as a unit, at least in theory).

I willingly join in. It sounds so simple, one car leads, and everyone else follows while staying in sight of one another. There are shared playlists, group texts, pinky swears to not let anyone out of your sight. Sounds fun, right?

We put aside our niggling nervousness and decide this will turn out to be a really good time for all – just like in the movies. But will our road trip be Smokey and the Bandit or Cannonball Run or Mad Max: Fury Road? 

The point of those movies (and my own experience) is that traveling together is never simple (and inevitably full of life lessons). Cars get separated, people like to drive at different speeds, and our need for indulgent snacks, bio breaks, and scenic overlooks rarely align.

The lead driver forgets to signal or signals too soon, some (but not all) of you want to pass the driver going 45 mph on a 65 mph stretch of road, and someone invariably veers off for gas without telling anyone. By the first rest stop, half the group is typing “Where are you” in the group text.

Not surprisingly, every team I’ve worked with or been a part of runs into the same issues.

Staff teams and boards (which are teams, after all) operate like caravans – well-intentioned people (hopefully), all heading toward the same mission-centered goal (hopefully), and with very different ideas about pace, authority, and what traveling together means in practice (definitely).

Sometimes, staying in your lane helps the group stay together. Sometimes it leads to siloing and a “not my problem” mentality.

Sometimes, fanning out to fill all the lanes on the highway keeps the group together. Sometimes it confuses everyone about who is leading.

Intentionality is the key (oh … isn’t it always?). Before you start your engines, remember that no successful caravan begins with, “Just follow me. We’ll figure it out.” You try that approach once, promise me just once.

Leaders need to create alignment before the team starts their engines. They need to set a vision for where the group is going, which route is the most efficient way to get there, and what landmarks will keep us unified.

Leaders and social directors also need to include every driver in figuring all of that out. We won’t share the road unless we see ourselves invested in the journey. Healthy disagreement and compromise in the planning phase reduces confusion along the way.

Including every driver does not necessitate including every passenger in the decision-making, though. Some caravan members just need to be informed and make sure that ample snacks and Mad Libs are readily available once we hit the highway. Too many voices make for a blah trip for all.

The planning needs to be thorough, because the group organizer rarely ends up leading the caravan on the trip. They were good at picking the destination and route, but they may not be the right driver for the lead spot. They help identify who has the best knowledge of the route, won’t get too far out ahead of everyone, and has the stamina for the first leg or entire journey. They let that person lead with occasional check-in texts for support and counsel, if necessary.

Like multi-year strategies, some caravans are also long, and the road may change before the trip is over. You run into unexpected construction, detours, and bad weather. Good caravans and good teams rotate leadership to match the terrain.

The person who led the first leg can happily go back to the middle of the pack and exercise their followership skills.

Speaking of followership, it is just as critical to the success of the caravan as leadership. Once you’ve informed key decisions, you put aside disagreements, get in line, and help the group adjust if the need arises.

I sometimes wish in workplaces that we could see it as clearly as we do on the highway – when someone takes their own exit, hogs the passing lane, or keeps driving when the tank’s nearly empty. It’s so much more obvious than someone surreptitiously pursuing their own agenda, taking longer on tasks than they need to, or depleting themselves without asking to recharge.

We don’t get flashing lights on our organizational dashboard when someone’s weaving or tailgating. We have to communicate regularly about lanes: how to stay in them without losing a sense of where other drivers are and how to change them without causing skidding brakes and honking horns.

There’s comfort in lanes and no chance of success on a highway without them. The boundaries give us permission to focus on what’s right in front of us (which may be an “I’m texting while driving” erratic nightmare, ironically).

In organizations, lanes can become silos too. Siloed teams move efficiently but in isolation, impacting everyone’s momentum and visibility. Leaders must help everyone merge, signal, and adjust pace to make sure the caravan stays together and that no one is stretched too thin.

The best leaders know how to navigate lane changes and keep everyone together:

• They signal early. When it looks like a change might need to take place, they communicate it as soon as they know, so that others can see the course correction coming.

• They check for blind spots. Before making a move, they make sure they know where everyone is and that their move won’t cause collisions or near misses.

• They survey the landscape. After they make a move, they look in all directions to see if they caused any disruption in the caravan. If they have, they activate the group text to bring everyone back together.

• They maintain a healthy distance from others. Good leaders don’t suddenly pass everyone and take over the lead spot. They support the drivers from behind.

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The leader’s job changes along different stretches of road – it isn’t to drive every car (or understand the ins and outs of how every model of car operates), but to keep the caravan unified. Successful caravans rely on trust, built on solid communication that gives each driver autonomy.

Good leaders help their caravans stay aligned, even through detours (and even the best caravans drift apart now and then) and pit stops (we all need rest stops to refuel and recalibrate).

In leadership, as on the highway, be clear on your destination, accept that your pace may not be everyone’s pace, and stay in close touch with the people moving beside you. And remember to bring treats. No good caravan or team meeting was ever derailed by too many yummy snacks.

Before your team caravans, a small moment of clarity pays off. Ask yourself: Have we really agreed on the route? Who’s leading this stretch? And when is it time to switch drivers?

If your caravan could use clearer routes, smoother lane changes, and fewer fender benders, let’s talk. You can email me at gary@garybagley.com or DM me on LinkedIn.