helping organizations, teams, and individuals take their work to new levels of success by identifying, languaging, and leveraging their strengths


the fine art of f*cking up

I want to talk today about mistakes. Specifically, I’m thinking about two mistakes that Mariah and I made in working with a client several years ago. 

As part of a larger project, we needed to get Board members to identify the organization’s key strengths and envision a new future for the organization. Cool, right? We were excited. A retreat was scheduled for mere days after we were brought in, but this is the kind of thing we love to do, so we jumped in and said yes. 

The night before the Board retreat, we were invited to a casual meet and greet with staff and Board. The ED gathered his leadership team and us so that we could review plans for the next day, which he’d already reviewed and approved. The leaders were not pleased with what we presented. The leaders had many opinions about how the day should go. It was 10 p.m. and we were scheduled to begin at 9 a.m. the next day.

We ducked back to our tiny former-convent retreat room and scrapped our plan, constructing a new one, finding the closest Kinko’s and making a midnight run to print off the new handouts. 

The Board session was to be a half-day affair. We launched into it with high energy, high hopes, and full caffeination. The first hour or so was relatively successful. Then phones started coming out. Side conversations picked up. Discussion became stilted, sighs deepened, a few people suddenly had flights they had to catch. 

We kept on. We stuck to the midnight plan. We smiled, we referred to group agreements about phone usage, we got through. We took down our wall-size post-it notes, thanked our staff contact and bolted for the nearest door. 

What went wrong? We made two major missteps. 

Mistake #1: We ditched our good plan for bad reasons.

Because we agreed to the project at the last minute, we weren’t able to meet with leadership team until the night before the event, and we let their fear and worry outweigh what we knew needed to be done. We let our desire to please the client get in the way of accomplishing the goals of the project we were hired to do. 

Mistake #2: When the train went off the rails, we kept going.  

We were determined to get through that morning session on plan, on time, according to the agenda. What we now know to be true is that the magic of what we do -- holding groups, bringing forth ideas and information, reframing and visioning and strategizing -- requires flexibility just as much as it requires planning. 

Later in the same project, we had the opportunity to work with the full staff of the same organization, and we made two essential good moves using what we’d learned from our mistakes.

#1: We involved the leadership team in concepting the plan for the staff retreat well in advance, and were able to make clear the links between the activities and the desired outcomes for the project.

#2: When issues surfaced among the staff that made it unproductive if not impossible to continue with the plans we’d laid out for the day, we paused. We came up with a revised plan, checked in with the ED about the course-correction, and came back to the group with a new set of goals and activities in hand. 

Could it all have gone better? Sure. Could the leadership team have predicted that the staff was in no way ready or willing to pursue the goals they had for the retreat? Possibly. Would we have packed extra chocolate and pre-scheduled massages for the next day if we’d known we’d be uncapping months of compressed frustration? Definitely. 

But this is the thing: we have to be gentle with ourselves, and each other, in order to learn. And as important as the work this organization is doing in the world is, as important as all of our clients’ work is, what matters most is that we are growing, evolving, dynamic humans engaged with each other in meaningful ways. So we call that a win, or at least a lesson, and we go on.