Reflections: conversations, paradoxes, and change management
Keeping things lively!
Just wrapped up another busy yet insightful couple of weeks at work, with career planning sessions and cross-functional alignment — and meeting up with some colleagues for a lunch outing! As I’ve said in an earlier post, I truly take pleasure in meeting with my teammates in-person, to help break the Zoom/Slack monotony and enable memorable moments of human connection.
⚡️ Lively human conversation
In particular I miss that leisurely co-worker lunch, getting out of the confines of the office to discuss complex or thorny issues through the art of conversation. 💬 (and of course, with tasty food and drink!) It’s a communal space to acknowledge each other as real people — not a time-stamped thread of interspersed asynch comments and emoji reactions, or a time-boxed video call where “clarity - brevity - sincerity”1 prevails so as to achieve communication efficiency in 20-30 minutes. Actual live human conversation is rather messy, dynamic, engaging, personal, with free-flowing interruptions as part of the back and forth (not the awkward cross-talk and pauses of videos calls due to a single microphone — or feeling you’re “in the spotlight” on camera), enriched by hand gestures, body language, and…eye contact! 👀 The result is often a fuller sense of who everyone is, where they are coming from, and how we can support each other — yes, empathy! And perhaps some of those resulting “warm fuzzies” persist long after the lunch is over, carried over into the digital remote comms…humanizing them just a bit more. 🤗
🕸️ The paradox of design
I’m constantly delighted to see junior-mid designers or non-design peers suddenly realize that working on a solution actually helps illuminate the nature of the problem even more — that by trying to solve (via mockups, prototypes, etc.) you are clarifying unknown issues, subtle boundaries, hidden conditions, and other aspects of the problem — as well as refining any associated hypotheses. These shifts happen — and it’s fully expected! 🙌🏽 Therein lies the fundamental paradox of design. Designing is not about spitting out one good solution and building it. As Nobel laureate & design theorist Herb Simon says, there’s a “conception and planning of the artificial” — it’s an iterative journey of exploration, understanding, learning, and realizing what might be, via making. Per my experience, it’s really not premature or apologetic to enter into the solution space “early” — indeed it’s a way of navigating with a conceptual flashlight 🔦 and seeing more of the contours of the problem cave you’re trying to get out of. 🤓 It’s only premature when you get fixated on a solution without sufficient confidence or clarity via the initial sensemaking / exploratory activities!
Ultimately, by knowing the problem-space more deeply through making solutions, the right or appropriate kind of solution will emerge that fits the clarified problem.
☀️ Change management matters
It’s an incredible career opportunity to conceive, plan, and deliver a major re-design of an existing body of functionality. Then you’re moving customers from a prior version to a newer, modernized next-gen version — which is super exciting and yet can be a terribly fraught experience for customers, especially in enterprise / B2B SaaS world where significant labor & cost investments were made. Not to mention habituated usage of tools or features for critical in-flight projects. 😬💰 Thus, it’s vital to remember the change management aspects of migrating customers over; designers can play a valuable role in facilitating this process, by guiding Go-To-Market and Customer Success/Support teams accordingly.
Change is hard — nobody likes it, but it can be made easier.
This can involve helping shape a comms strategy with proper tone & voice that create psychological safety while extending your brand voice in an empathetic manner. Invest in materials to help inform, educate, train — with constant reinforcement. Apply service design lenses to help identify key touchpoints and set them up to be moments of high value interaction — as well as feedback loops to continuously monitor and react accordingly. Designers can help guide this process, providing necessary assets of course, but also framing the efforts as a coordinated, collaborative activity that everyone should prioritize to ensure successful adoption of a new design or feature set. After all, you can design and ship the most amazing “new version” of something, but if there aren’t effective, supportive pathways to ease customers into the new world, all that effort could be for nought. 😔
This is the so-called “CBS model” that rhetoric scholar Richard Lanham cites and critiques in his book of essays, The Electronic Word.

