“I used to think I understood my counterparts’ challenges, and now I think I need to ask more questions.”

“I used to think everyone had the same understanding of the differing roles/responsibilities in each function within our team, but now I think many leaders have developed their own expectations based on their own needs.”

“I used to think my own function was aligned, but now I think we are not.”

Those are a handful of reflections from a team Ei led through a one-day onsite last month.

The leaders of this team didn't come to us because they were struggling. Everyone on this team is smart, committed, and working hard. But some of their ways of working were leftover from previous iterations of this team and no longer serve who they've become. The world is changing rapidly around them, and they can't afford to hold onto habits that helped them thrive a few years ago but are holding them back today.

So they asked us to guide them through some "strategic disorientation." The goal: help each person lift their head up from the process, question the way things have always been done, and see the full system they're part of.

Before our one-day session together, we asked each individual to answer three questions:

There were 33 people in the room, and it might not surprise you to learn that each of them wrote different answers to the three questions. Some of the answers differed only slightly, but some differed so far as to be entirely opposite from each other. So… it was time for a truth tournament!

When we all got in the room, we had each person hold onto their answers and pair up with another person.

Partner A shared one of their answers.

Partner B’s job was to dispute that “truth:”

• "While that may be true in some cases..."

• "That assumption breaks down when..."

• "Here's where that may not be true…"

Then, Partner A piped up to defend their “truth:”

• "While I concede that..., it's still true that..."

• "The data I would turn to is..."

Then came the fun part.

We had them tear their names off their papers, swap papers, and repeat the exercise with a new partner.

So, now they had to defend a truth that wasn’t theirs to begin with.

After a few rounds of this, we started to see the effects of the strategic disorientation.

“Truth” and “fact” were downgraded to opinion and assumption.

Gaps and misalignments became more visible.

The exercise isn’t meant to stump or confuse the team members. It’s meant to encourage a habit of assumption hunting.

If everyone on this team starts to recognize when they or someone else is making an assumption, they’ll more quickly be able to challenge those assumptions and seek new possibilities. In meetings with each other, instead of drifting into familiar territory or repeating old decisions, they’ll start pausing and asking things like: “What if the opposite were true?” “Who might see this differently?” “What do we know for sure, and what are we inferring?” This line of questioning leads to new ways of seeing, and new answers to old conundrums.

To this end, a bit later in the morning we invited small groups to identify one assumption they heard in the answers that, if flipped, would change everything.

Here are some of the possibilities they opened:

You can see how each of these assumptions, when flipped, would lead to a radically different strategy for this team.

So, after a morning of strategic disorientation, we started the process of realignment. It would take another newsletter to describe the afternoon, but it included some 1:1 interviews, a gathering of requests and offers across functions, and drafting some strategic “even/overs” to guide choice-making for the next 6 weeks.

While this single session is only the start of a longer process, we were thrilled to see that 100% of participants committed to shift at least one way they work within this team, and 100% said they were leaving feeling catalyzed and hopeful.

Want to try this with your own team? Start where we did. Have everyone answer the three questions above on their own, then compare notes. The gaps you find are your starting line.

And, if a guided version of this kind of disorientation and realignment sounds like it could benefit your group, we’d love to connect.