Leaning into the Tough Stuff: How Uncomfortable Conversations Show Up in Our Client Work

A few years ago a small innovation group came to us with a problem. They were part of a large, complex healthcare company and were having trouble getting stakeholders within the larger organization to open up to them. They wanted us to teach them to be more effective interviewers. But we discovered that the real problem wasn’t rapport building or interviewing skills, it was how they were perceived throughout the rest of the organization. They had taken a lot of insights from talking with other teams, insights that didn’t make their colleagues look good, and there was a general feeling that talking to this group was essentially airing dirty laundry in front of the boss’s boss’s boss—that the worst aspects of your work were going to be sent up the chain of command, all the way to the top.

Relaying this finding was one of the hardest conversations I’ve had to have, because it meant starting to push back. It’s easy to talk about a tool, a tactic, or some relatively simple skill, but a conversation about, for instance, a client’s reputation within their own organization, and how they’re creating a feeling of insecurity even while trying to help, tends to turn uncomfortable pretty quick. In this case, our clients had to ask themselves, What do we really stand for? And are we helping or hurting more? And so did we.

The kind of innovation consulting we do often seems like therapy. Our most interesting projects rarely come from our first pass, or our client’s first pass, at what together we want to get to. It takes a few layers of depth to reach what’s truly important. That’s why uncomfortable conversations are so important—they’re part of the continuous digging we need to do until we get to the substantial issues below the surface.

So when these scenarios arise, we lean into the tough conversations instead of avoiding them:

A passion project with a grand objective. 

This often occurs when a client is first building an innovation group or tackling a tall order such as how to bring a greater sense of humanity to their work. They’re trying to figure out how to make that grand ambition as safe as possible—to ensure the initiative succeeds. 

We hear a lot of language from our clients to the tune of “This is a culture where we’re free to fail, and fail forward and fast.” But when it comes down to it, they realize that their company does not actually afford space for that. They feel like this is their one chance to nail this project and get more support. So they have an internal conflict between their desire to be bold and their assumption that they must water down the initiative in order to get it through.

An issue that feels introspective and deeply personal. 

In working with a social network with a very large teen user base, we brought school psychologists and guidance counselors into the room, and we asked people to swap their product manager hat for their Mom or Dad, or Aunt or Uncle, hat. That was a difficult conversation. You might feel comfortable with it in the context of, say, having drinks with friends after work, but when you’re sitting with your colleagues and everyone’s on the hook for creating kick-ass products, and you’re talking about whether those products are detrimental to a generation of kids—well, that is truly hard. 

In this case, the conversation took a lot of warming up. There were maybe three or five people in a full room of forty who were initially open to it and willing to raise their hands, but slowly and over time more people started to join in.

Misalignment on what success looks like. 

This happens often with visioning work with leadership teams. We might come into a room with a question that we’re supposed to be helping the team work through, but the premise of the question is incredibly loaded and there may be fundamental disagreement on whether it’s even the right question in the first place. So as we try to move into getting to solutions, we start to see an unhealthy debate in which one person tries to take ideas in one direction and someone else tries to take them in another direction—and they’re both upset that the other person’s premise is still on the table. 

As facilitators, in that moment, we wonder what to do: Do we allow this infighting, with its potential for an ugly public scene, to break the process for 25 people in a room? Or do we choose one direction or the other, leaving a fight to be had afterwards? And does that negate all the work we just spent two days doing? Figuring out how to step into the argument in a way that feels authentic and honest—and to convey the tension we’re feeling within the dynamic—allows us to model a behavior for stepping back off the ledge, breathing a little bit, and being direct about what’s creating so much tension and anxiety. Why is this such a fighting point?

Digging, uncovering and understanding clients’ needs and motivations. 

When we drill down into a client’s motivation, concerns, and questions, as well as into the sensitive organizational context, we get a deeper and richer take on a project. This leads to outcomes with much greater impact. 

The problem with digging below the surface to root causes? It’s not always what a client wants. The briefs and scopes of work we get tend to point to surface-level things—generic issues that everyone is aware of, that don’t make the client feel too vulnerable putting out there, and that seem relatively easy to solve. We tell ourselves we need to get a quick win—so why don’t we look at taking on this given challenge and all end up feeling successful? But this creates a culture in which people try to address only the easiest things and leave the difficult, ingrained issues to fester or grow. It also creates a place where people care less about that project, because they know they’re not solving anything that feels significant. 

Ultimately, the purpose of an uncomfortable conversation is to allow us to move through all the surface-level stuff that’s not going to make a difference, and to figure out how we actually get to the things that have significance. These don’t tend to be process problems, which are easier to take on. They tend to be people-oriented problems—the ones that are just easier to avoid. And avoiding them is what created the problem to begin with.

Engaging in uncomfortable conversations is as difficult for us as consultants as it is for our clients. We worry that digging into issues people would rather leave buried might cost us a valuable relationship. But we’ve found that when we balance our discomfort with empathy and openness, such conversations benefit both our clients and ourselves.

Jason Wisdom
[email protected]

Jason Wisdom is one of the co-founders and partners at The Design Gym, a strategy and innovation consultancy helping leaders to grow their business by fully unlocking the power of their most important advantage: their people. We work at the intersection of business strategy, experience design, and change management to engage the people that matter most to your work: your customers, your leaders, and your employees. See something that resonates with a project or challenge you're working on? Shoot him a note at [email protected].

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