Conversation at Scale: Curating the Enterprise Experience

Louis Rosenfeld
Rosenfeld Media

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This is the written version of a short speech I’m presenting to a group of past and present Enterprise Experience conference speakers in late August of 2020. Sometimes it helps to write these things out in advance…

Way back in the aughts, when I was an independent information architecture consultant (between my Argus and Rosenfeld Media careers), I worked with huge enterprises like Caterpillar, Ford, Paypal, the VA, and the CDC. I did my darndest to get those organizations to make their information more accessible — to customers, partners, and employees.

While I had some successes here and there, I mostly failed. I had great information integration skills, but I was shit at people integration. My professional toolkit was insufficient for helping people collaborate across a large organization’s silos.

I tried to up my game. I tried to learn what made people working in large organizations tick. I tried creating strategic roadmaps, working with mental models, triangulating storytelling and metrics, and doing all sorts of things to free people, as well as content, from their silos and get them to think and collaborate in new ways. I wondered how to dynamite those artificial divisions — as you’ll see if you look closely at the banner for my “Enterprise Information Architecture” workshop below:

Banner for my old workshop on Enterprise IA. I’m holding my EIA roadmap, looking forward to blowing up some corporate silos. The wonderful Kevin Cheng created this illustration. He later wrote Rosenfeld Media’s See What I Mean. I wonder how Kevin’s doing.

But it was excruciatingly difficult. The only way I felt that I brought my clients any value was by simply letting them vent. And boy, did they vent — about their teams, their bosses, their development partners, their product managers, and most of all, their senior leadership. It got so bad that I started saying that I wasn’t really an information architect anymore; “information therapist” was a much more appropriate term.

It got so bad that I had to find a new outlet where I could feel like I had some impact, actually see things through from concept to fruition. So I got the dumb idea of publishing UX books. As a hobby.

Eventually Rosenfeld Media generated enough momentum to liberate me from consulting. It’s a wonderful feeling to make real things that bring people together, though I often miss the freedom of not worrying. Not worrying about making sure my staff gets paid, our authors and speakers and instructors are productive and motivated, and that our tens of thousands of customers stay engaged with us in a variety of ways, including the ones that keep the Rosenfeld Media ship afloat.

That’s a lot of stakeholders. I also have to worry about things like distribution and warehousing, financial projections, customer service, contracts with hotels and caterers, and, increasingly, how to partner with hungry 800-ton gorillas like Amazon without getting completely obliterated.

In a way, running little old Rosenfeld Media has a lot in common with working at an enterprise: distributed customers, users, and partners, distributed decision-making and ownership, and complexity up the wazoo. Maybe we don’t groan under quite the same level of scale, but some days even that feels like a burden.

So, as you can see, I completely fooled myself: I thought that starting a small company that made physical products would free me from the insanity of working with enterprises. Instead, I ended up building my own enterprise!

My naiveté has helped me learn two valuable lessons. The first is about potholes.

In distributed, networked, technology-driven economies, complexity expands to fill all available space. There’s no nook or cranny in the Rosenfeld Media ecosystem that gets left unmuddled by some new idea, product, or service, and each of these new complexifications creates new nooks and crannies, and those gaps get filled with more complexity, and so on…

In other words, the crazy dysfunction that we’ve all associated with the enterprise is increasingly characteristic of every contemporary context, whether our local PTA, a doctor’s office, refinancing a mortgage… even a small publishing house.

A lovely image of a pothole, from the Town of Montville, Connecticut website.

What does this have to do with potholes? Well, as you know if you’ve tried, it’s incredibly complicated to get a pothole filled. And, somehow, the filling of a pothole, due to complexity and chaos theory, somehow leads to the creation of another gaping pothole somewhere else for someone else to deal with.

If you work in enterprise, you’re already familiar with this cruel game of whack-a-mole.

The second, more important lesson is this: there is a way forward, and it starts with conversation.

I failed at enterprise information architecture mostly because I couldn’t see what was right in front of my face: the way to get people to collaborate across silos and see beyond their own motives is to get them talking. To give them a vocabulary to discuss the common challenges they face, and a platform to enable those discussions. In effect, to get those famous blind men from the ancient parable to talk in order to achieve true insight — to identify that great big messy moody elephant.

My favorite parable. It really encapsulates so much of what user experience is about. Dave Gray, one of the most visionary people I’ve ever had the pleasure to know, illustrated it for our book Liminal Thinking.

My co-authors and I did this with the polar bear book. We got developers, usability engineers, graphic designers, writers, librarians, and other odd ducks who generally had little to do with each other talking about their shared information pain. We gave them a common language, set of concepts, and framework —just enough so they could talk among themselves and combine their respective abilities to solve information problems together.

Obligatory image of the polar bear book.

Really, if you can get people with disparate perspectives to get together to talk, that’s half the battle right there.

Since then, I’ve taken the same approach with Rosenfeld Media’s books, conference programs, and the communities that we host. To be successful, these need to both further and reflect back on the conversations that their broader communities are engaged in. Books and programs are simply polished, well-designed snapshots of those conversations. That’s why we make our speakers talk about their ideas together for months and months before they present; collectively iterating the conversation directly leads to the great presentations they give from our virtual stages.

My mistake when working with enterprises: rather than integrating information, I should have looked to integrate people across silos by curating their conversations. By surfacing, broadening, and facilitating the conversations they were already having within their teams, product groups, and silos. And by providing them with the necessary connective tissue of cross-silo conversations: language, concepts, and frameworks.

Rather than serving as a therapist for one frustrated stakeholder, I should have been connecting the different threads of conversations among multiple stakeholders. I should have been studying group facilitation and organizational dynamics, not to mention mediation and conflict resolution. I should have been identifying the boundary objects that live at the intersections of an enterprise’s silos and disciplines. Maybe I should have tried to create a Rosetta Stone to connect and translate among them.

Lots of “should haves”. But I know—from writing and publishing books, putting on conferences, and hosting communities—that enabling conversations to happen in your enterprises is your only shot at success. Once you get smart people with different perspectives talking, they’ll figure out how to move things forward on their own.

If you’re having success at anything within an enterprise setting, I’ll bet dollars to donuts that somewhere, sometime, somehow, you got a ragtag set of people talking who simply didn’t talk before. Think about how that conversation got going, how it went, and most importantly, how it was sustained. What vocabulary was necessary to fuel the conversation? Were there shared concepts, frameworks, boundary objects, or even simple problem statements that powered the conversation? And how did you get to be an enterprise conversationalist in the first place?

If you can answer any of these questions, you could give an absolutely fantastic presentation at one of our upcoming conferences. And that you might have a book inside you that’s dying to come out.

We’ll talk later.

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Louis Rosenfeld
Rosenfeld Media

Founder of Rosenfeld Media. I make things out of information.