We Know What Could Go Wrong. But What Could Go Right?

A few weeks ago, I joined a small group of people helping a fellow entrepreneur think through improvements to the way she implements a specific business system with clients.

I should mention that we are, collectively, a very process-minded bunch. I’m pretty sure all of us wouldn’t mind losing ourselves in the color-coding of a spreadsheet from time to time. Within our group, there are facilitators, project managers, trainers and people who genuinely enjoy a good framework. And in one of our weekly meetings, we generated more than 30 ideas for strengthening different parts of the system, from delivery and documentation to the overall client experience.

Then, earlier this week, I stepped in on short notice to facilitate our next conversation, where the goal was to narrow the idea list and figure out where to start.

It seemed simple enough.

Should we vote? Maybe. But first, should we sort the ideas by impact and effort? If we are going to identify “quick wins,” how quick does something need to be? Is the effort about time, complexity, cost or the number of people involved? Would high, medium and low be enough? Maybe “T-shirt sizes” would be a helpful prioritization structure?

None of us were being difficult. Quite the opposite. Everyone was trying to make sure we had enough shared context to make a thoughtful decision instead of having seven people rank things according to seven different sets of assumptions.

Thankfully, we eventually landed on a reasonable next step…but I kept thinking about that meeting afterward for another reason.

One of the ideas I had contributed to our original brainstorm was that the system’s implementation experience itself might benefit from incorporating more storytelling and visualization. How could clients more clearly see themselves on the other side of the work? Could we invite them to form a clearer picture of what successful implementation would actually look and feel like?

There was some irony in realizing that our own group had just spent quite a bit of time figuring out how to evaluate the path forward without spending nearly as much time picturing where we hoped that path would lead.

We have plenty of imagination. We just don't always aim it forward.

Visualization has been following me around lately, it seems.

I recently listened to a Mel Robbins podcast recommended to me by a client that explored imagination, storytelling and the ways we use mental pictures to make sense of difficult experiences and possible futures.

It stuck with me because many of us don’t exactly suffer from a lack of imagination (myself included).

Give me enough uncertainty and I can build a very respectable worst-case scenario all by myself. Thankfully, I’m not as accomplished at catastrophizing as I used to be.

Teams are pretty good at this, too.

We all huddle around the Keurig, waiting to pop in that pumpkin spice K-cup, and start asking what could go wrong with the upcoming change. Who might resist? Where is the process likely to break? What if people don’t use the new tool? What happens if this person leaves? What if we’re underestimating the workload? Who have we forgotten to involve?

And, naturally, what if we run out of K-cups?

Those are good questions, and teams shouldn’t stop asking them. After all, a part of managing change well is recognizing friction before you're standing in the middle of it wondering why nobody saw it coming.

Over the past years, I’ve increasingly appreciated the value of intentionally assigning someone on a team to act as a “challenger”: the person who tests assumptions, pokes holes in the plan and helps everyone prepare for problems.

Sounds like a useful role, huh? But lately I’ve been wondering why we aren’t just as intentional about naming that role’s counterpart. Who's asking what happens if this goes well, and what will it look, sound, and feel like?

“Success” can be surprisingly hard to picture

Organizations usually have language for the future they want. It’s their vision.

They want to experience better communication, stronger collaboration, a seamless client experience, greater efficiency, and/or better adoption.

Those are worthwhile aspirations; however, we just don’t always make them specific enough to be useful.

What does “better communication” look like at 10:15 on an ordinary Thursday in September?

At a nonprofit, it might mean the development and program teams can both see the latest donor or grant-related information without piecing together updates from email, a spreadsheet and someone’s memory.

At a small consulting firm, it might mean the person managing marketing or sales operations can open the CRM and trust that the pipeline reflects what is actually happening, without maintaining a separate tracking sheet on the side.

Or it might show up during onboarding, when a new employee gets through the first couple of weeks without having to guess where information lives, who owns what or which decisions they can make on their own.

That’s when a vague idea like “better communication” becomes more useful and actionable. You can see the day-to-day difference it’s supposed to make and, from there, start working backward into the processes, roles and systems that would have to change to make it real.

Make the future specific enough to design

Not surprisingly, once you start seeing a theme, it’s easy to see it everywhere. This idea has been showing up in my coaching work lately, too.

My own coach used a similar exercise with me recently, asking me to personify the version of myself I’m trying to grow into and contrast it with how I see myself showing up now. I found the exercise surprisingly useful, so when a similar tension surfaced in a conversation with one of my own coachees, I adapted the idea.

I asked her to describe the version of herself she was trying to become. We made that future state a little more concrete and gave it some personality, then contrasted it with how she felt she was showing up in the present and imagined what those two versions of herself might say to each other.

Once the future became easier to picture, we weren’t talking only about how she wanted to feel. We were talking about roles, delegation, boundaries and how she wanted to spend her time. The future started giving us clues about what needed to change in the present.

Teams can do the same thing. Instead of stopping at “Do we agree on the goal?”, we can get much more specific:

• What does an ordinary Thursday at 10:15 in September look like when this is working?

• What aren't people chasing down anymore?

• Which conversation has gotten easier?

• What information is easier to find?

• What does the team have more room to do because some recurring frustration has disappeared?

These may sound like coaching questions and, ding-ding-ding…they are. But they’re also useful systems questions.

The answers can surface things a project plan won’t. Maybe one person hears “more efficient workflow” and imagines more autonomy, while someone else assumes it means tighter standardization. Or, perhaps a leader is picturing technology removing a step that someone on the team sees as an important part of their role.

That’s useful to know before everyone starts building toward a future they thought they agreed on.

And there may be value in borrowing one more piece from the coaching exercise: once the team can picture that future version of itself, what would that team say to the one doing the work today? What would it tell them to stop tolerating, clarify sooner, or start practicing now?

Preparing for trouble and moving toward something

None of this means positive thinking should replace practical planning. The interesting part, to me, is the duality of the combination.

Research by Gabriele Oettingen on “mental contrasting” has explored the value of holding a desired future alongside the obstacles that could prevent us from reaching it, rather than relying on positive fantasy alone.

That feels pretty applicable to organizational change, too. I think we need someone asking:

Where might this break?

And, we also need someone asking:

What are we trying to make possible?

One question helps us prepare, and the other gives us somewhere to go.

I imagine I’ve been noticing this pairing more because another version of it is playing out at home. My son's high school marching band show this year centers on comedy and tragedy—the two theatrical masks, side by side, creating a fuller story together than either would on its own.

Risk and possibility feel a lot like that to me. Neither cancels out the other. The value is in holding both. So yes, keep asking what could get in the way, but give the future some airtime, too.

It doesn’t need to be a sweeping vision of transformation. Sometimes it’s simply a clearer picture of an ordinary Thursday in September where the information is where people expect it to be, the handoffs make sense and fewer things fall through the cracks.

What will your day look like when this is actually working?