Reflections & Intentions: 2018 > 2019

Looking back, for me 2018 — which felt like it lasted a decade! — was a year of transitions and connections, of not knowing and adapting to the unexpected, while seeking out those elusive moments of … discovery? achievement? fulfillment? Perhaps it’s simply the search for the most mundane thing of all…quite simply progress.

As Mad Men’s Don Draper said often, “move forward”. So I did.

I leaped from the relative safety of a full-time stable corporate job into the volatile, risky frontiers of UX consulting — again! As a much wiser friend said, as designers we’re never fully satisfied in our work, instead constantly shifting among various states of want and give, whether it’s projects or clients or companies or tools & skills. And so it was for me, this time trying to “do it all” in this crazy blend of engagements: advising & helping startups, contracting for a newly-found UX agency, my own indie consulting, continuing with UX conferences, and even flirting with a potential full-time teaching role. Throughout I was constantly proving myself, building credibility, developing trust, retelling “my narrative” — it’s a never-ending enterprise, this thing we do as designers. Rather painful, no? I concluded the year by re-affirming my design leadership position joining a startup as their head of UX whereby I’m shaping a new business strategy via design.

But what did I get out of all that activity in 2018? I’d like to share a few insights:

1 – You don’t always have to know what you want; sometimes you need to wander through the muck a bit to realize what you need and value. Relatedly, maybe (particularly if you’re stuck in a rut) the better way to know yourself IS actually to dive into something unknown — with eyes wide open, of course!

2 – Engaging with ambiguity while knowing that it might fail, that’s really hard and has a cost / risk factor that only you can reckon with. Everyone will try to pull & push you in different ways but only you should decide what’s right for you. And maybe, you need to be pressure tested a bit, to sense the edges of your comfort zones. Then, when it gets too much, simply walk away, knowing that you tried and hopefully learned, albeit the “learned lesson” may not present itself until much much later…

3 – You own your time. You always have the right to say “no” and walk away (professionally and gracefully). You are in charge of your narrative — both as a self-referential thing to affirm your value to yourself (indeed, in this business we’re often our own toughest critics!) and as a way to build relations with others who don’t know you, but willing to interact and understand what you stand for.

4 – That narrative is iterative and situational, necessarily so, given the context and personality and type of role or position held by that other person. (Note: your “narrative” is not some cynical “spin”, but more of a shaping of messages and how you project your self)

5 – Trust and credibility are multi-faceted concepts that evolve over time with different people, per contexts. Everyone has their own “way” of building that up with you (and vice versa). Getting a coffee or beer usually helps; truly get out of the office to help foster those ties into valuable relationships. And guess what — sometimes it just doesn’t work out; you’re both not seeing eye to eye no matter what. Keep moving forward!

6 – Explaining design and how / why you do what you do as a designer (and as a design leader) — that never stops. You will always be doing that! Keep iterating that narrative.

For me, looking ahead to 2019 (and perhaps beyond), I’m realizing that I’m moving even more away from traditional “UX” and much more into matters of leadership, strategy, even philosophy. So for my annual intentions (as opposed to resolutions, which sound so hard cut), I intend to do the following over time:

1 – Keep pushing on the notion of “meta-design” in my work: literally designing the conditions to enable good design to happen. This also extends the effects of design beyond “the screen” towards the organization and more.

2 – Keep evolving & refining my “playbook” as a design leader per insights from non-UX leaders, from Sales, Engineering, Product, Marketing, etc. What are their perspectives and how can they inform my approaches? There is a vital interdependency to our work that I deeply aim to foster more of.

3 – Keep advocating for a systemic, framework-level point of view to wicked problems, and really dig into that ambiguity in a cross-functional manner. So, this naturally requires helping others get comfortable with being uncomfortable ;-)

And ultimately I intend to keep testing and evolving my own “dynamic balance” (per the classic Eames diagram) of competing yet cooperative aims and situations and opportunities. It will be another interesting and fun year!

Disposability in design: feature not a bug

Building upon the previous post’s point about the need to “show the ugly” in design, not simply jumping to and showcasing your gorgeous Sketch mockups via templates and plug-ins…There’s another point about the value of disposability that’s worth mentioning briefly.

To be disposable in the design process is essential to the overall nature of design as a progressively iterative practice of moving from existing (meh) to preferred (yay!) with improvements upon the human condition or activity. This refers to quick pen sketches, drafty wireframes, hacked together prototypes, and even quick personas or experimental designs to see what feedback comes back. Each example speaks to how to be adaptive and improves with the tools and materials at hand, in order to create something that a) speaks to Product priorities for delivery to market and b) supports user goals and attitudes for actual usage.

Disposability is vital to reducing the cost of iterations, too, depending on how it’s built and shared. Via paper or quick smartphone photos stitched together, they afford rapidly facilitative discussions on the intent and outcomes, to ensure some kind of baseline direction with productive aims.

Disposability also ensures folks don’t fall in love with a design solution prematurely, by nature of the the rendering style (pen & paper) or the medium of the output (paper that’s torn and marked up), to ensure crucial conversations happen around the artifact itself, in service of product-driven strategies and ambitions.

That facility of easily and quickly throwing away a design keeps the team nimble, always thinking how to improve, and trying out crazy ideas. It encourages teams to be bold — after all, it’s only paper and pen or cardboard or whatever. So, yes… aim for the crazy North Star NOW and let’s discuss and get customer feedback, rather than holding things back out of fear and anxiety — which are the chief killers of innovation, and of memorable designs that enable customers to enjoy your brand, your product, your service within their lives.

Showing the ugly in design

Perhaps due to the ease & proliferation of Sketch templates for creating high-res mockups that look production-ready — dashboards to admin consoles to social feeds — there seems to be a strong bent towards going all realistic and photo-ready from the start of a project.

Please don’t do that.

I mean sure, why not make it look beautiful and well-formed, as if it’s already coded — indeed, modern tools make it so quick (time saving) and easy (just a few copy/paste/edit maneuvers). It seems to be a no-brainer, right? PMs, Devs, clients will love it — makes you look so awesome too. Capable of spitting out something that looks perfectly formed. Maybe so, but here’s something that’s lost — seeing the ugly, the disposability of doing rough pen/paper or whiteboard-based sketches that’s lower cost and reduce a team’s irresistible attachment to a finished-looking mockup. It also encourages the team to get involved in all the ugly iterations, the “wrong ones”, the “bad ones”, the “WTF are you thinking” ones…so everyone can understand/learn why they’re not good, how considerations or issues become clearer after subsequent attempts.

Creating a good design is not simply about spitting out that perfect gorgeous mockup for Devs to code up.

It’s more effectively about that elusive journey of exploration, discovery and understanding (or learning), an emergent revelation of what’s important (and conversely, not important), via a series of progressively iterative, increasingly higher fidelity creations that…

a) reveal levels of complexity and relationships among objects & actions — which non-design peers likely never knew or realized [spoiler: they’re often buried in tedious 100 page docs nobody reads, or across dozens of JIRA tickets in dozens of browser tabs]


b) getting non-design peers to participate on that journey, helping them recognize what’s important, and how design really happens, aside from pop cultural notions It helps (re)set expectations and disabuse others of false notions per media hype (the “magical genius designer with unicorn rainbows shooting from finger tips” — NOPE!).

It reveals the reality of design as a messy, ugly process of fits and starts, of zig zags and reversing course, of throwing away ideas quickly to make faster progress, of making (gasp) mistakes with a basket of crumpled stickies. It’s admittedly exposing the truth of the process, the essence of creation to those who likely are terrified of seeing the mess, the ugly before the beauty. After all, it just looks so risky and uncertain. Who wants that?? They have to guarantee 32.43% increase in revenue growth next quarter!!

But if you want to earn a team’s trust, and cultivate non-design peers as veritable partners in an ongoing process of generating & delivering long-term value (to customers and your own internal organization), then showing the ugly while holding their hand (metaphorically, of course), is so damn useful, and yes, so damn painful. By going through the visibility and honesty of traversing the ugly together, the collaboration is healthier, stronger, and has the caliber to withstand truly tough arguments when it comes to time to ship and make extremely hard trade-offs.

Showing the ugly helps.

Designer as interpreter & therapist

One essential truth of being a designer that I’ve realized over the past 15+ years of practice — with startups, large corps, and agencies — is that it’s not really about the the design itself. Of course, you are totally expected to deliver a well-crafted, thoroughly thought-out, and deeply empathetic or contextualized solution that speaks to business goals (i.e., metrics and OKRs). That’s simply a given, in terms of the deliverables and outcomes produced.

That’s the job.

But the implicit — and I’d argue greater — value of a human-centered designer on a cross-functional durable team is how that professional is striving to deliver against a deeply personal aspiration, which involves constant, patient, alert-in-the-moment collaboration with non-design peers — Engineers, Product Managers, Sales, Marketing, Support, etc.

Those collaborations inevitably involve sensitive, perplexing, and outright fraught conversations— i.e., conflict! Ugh.

But this is where the designer serves a profound complementary role. Not as some 11th hour savior with a “magical solution” (umm, that’s a fun myth) but instead as (a) an interpreter of various projected perspectives (borne out of organizational or personal agendas) and deeply felt values or beliefs (i.e., a “point of view”) via aptly communicative forms (sketches, diagrams, prototypes) for iterative deliberation of latent assumptions…and also as (b) a therapist (!) facilitating volatile dialogues that expose animosities, misunderstandings, contradicting beliefs, even bad (read: “counterproductive”) approaches per years of misguided habits.

The point in this case is deeply listening to the grievances exposed, while enabling the teammates to reflect a little bit themselves in a hospitable manner. Often they just need to air it all out in a group session, away from emails and Slack channels! Yes, it’s indeed a therapeutic activity, helping them see a better way, coaxing them along a messy journey, assuring them things will indeed work out (i.e., their goals will be achieved…if they work together for shared aims!) …And the designer can/should support them towards cultivating team trust or rapport, optimism and hope for a better way, and belief in the value of a humanistic approach that everyone can benefit.

The designer’s power

Over a late afternoon coffee, a fellow designer asked me “how can we have power as designers” — in the context of “those big decisions” being made by non-design leaders in an organization. Well, it’s a common question and I address it the following way, by sussing out the nuances of power, authority, and influence.


First of all — All designers have power. Our power comes from our ability to decode complexity & ambiguity, translate and interpret those issues, visualize (or somehow give form) them and stage productive dialogues that guide everyone towards an optimal solution that benefits the maximum set of overlapping concerns, as oriented towards the customer. That power is guided by an optimistic spirit of iteration and risk-taking and learning. That is our power and how we make use of that power is up to each of us. The question is whether that power has veritable impact for the causes we believe in — towards improving the human condition given various contexts.


But when I hear “why don’t designers have power”, what I really hear is “why don’t we have the authority” to make certain decisions (like stop an ugly and harmful interface going to market). Authority is contingent upon a variety of factors, given the organization — often dependent upon the power structure as codified by levels, titles, incentive models. Cultural factors apply too — is it a very hierarchical place or more egalitarian, large corp vs small startup, agency working a client, etc. But authority can also be developed via relationships with key figures in an organization and applying (consensually, of course) models of accountability like DACI / RASCI to clarify who “make the call” versus “who is contributing input”. Having been in multiple various corp design departments, I totally get the value of having a champion advocate for design at executive levels, truly empowered / authorized to make crucial “big decisions”, which is great for matters around culture, process, strategy, and especially vision-setting. But maybe not so much for why your PM didn’t like your dropdown menu design 😉 (unless it’s a massive systemwide UI component that will screw up core customer flows thus causing major support call headaches, etc.).


However, not all organizations or teams have the role of a Head of UX or similar, sadly. Or the issues being battled over are a bit too granular to bother the VP of Design (one should play that card carefully and use it in where it really matters — a whole other topic around assessing goals / risks / asks / benefits ). So what’s left is influence. This goes back to your power as a designer to shape and influence decisions by virtue of your talents around discovery, interpretation, visualization, and iteration — backed by compelling stories and rationale that speak to the goals of solving for customer problems.


Influence emerges through the designer’s ability to apply their power given a particular context, to achieve certain aims. It involves relationship-building, trust-building, active listening, humility and grace, with a touch of charisma, all backed by showing outputs and outcomes. Waging influence is an art, developed over time and with lots of practice, but it is essential to be an effective designer (and leader) who operates as a true partner with non-design stakeholders serving the needs of the customer & business overall.