Lessons from Leading UX at a Startup

Reflections for the future…

For the past year, I had led the re-invigoration of user experience (UX) at a Series C stage enterprise software startup, developing a cohesive, robust foundation with both company-wide & executive support. This included a mix of the following:

• A revitalized visual design language for style & communication
• Some visionary concepts to provoke & inspire what’s next
• Strategic advocacy of UX fundamentals to enhance the product’s value

Being my first startup leadership role, this certainly proved to be a valuable “high learning, high growth” opportunity filled with lessons, both small and large. I’d like to share a few that made the most definitive mark on me, shaping my design leadership model going forward. Hopefully this will help other design leaders in similar dynamic, small-team situations!


Say “no” to preserve your sanity (and your focus): It’s critical early on to set boundaries demarcating exactly what you’ll work on and what you’ll defer to others. As a former boss liked to say, “You can’t boil the ocean.” Be selective on where you’ll have design impact with immediate or significant results that you can parlay into your next design activity. Saying “No” also builds respect from others, informing colleagues that you have a direction and a purpose to deliver against.

Remove “like” from the discussion: Everyone has opinions about design — that’s simply natural and expected! One way to mitigate the “I like” (or “I don’t like”) is to remove that word and instead focus on “what works” or “doesn’t work” for a particular persona, context, or scenario. This forces the discussion to be about the functional nature of various design elements (yup, color has a function!) not subjective personal tastes, which tend to derail matters.

Role model good behavior from Day One: It’s only natural for a startup starved for design expertise to immediately ask for icons and buttons after the designer found the bathroom and got the computer set-up. After all, that’s what most folks see design as — the superficial “pretty-ing up” of things. (We won’t go into who to blame for that…yet ;-) So, as a designer in this context, it’s your opportunity to demonstrate the right behavior for engaging and creating, such as asking user-oriented questions, drafting a design brief, sketching on whiteboards, discussing with engineers, and so forth. Just go ahead and humor that first icon request, and use it to your advantage as a teachable moment for everyone. Be wary of setting up false expectations, but quickly build up a repertoire of good behaviors and teachings, minus the preaching!

Build relationships with Sales, your best friend: Yes, Sales! You gotta sell to customers and your sales leader will point you to the right folks to learn about customers, markets, and partners. Understanding the sales channel, that primary vehicle for delivering a great customer experience, is vital to your success as a design leader—particularly if designing for enterprise software, which thrives upon a solid sales channel. Build that rapport to actively insert yourself into the customer engagement process, which is a gold mine of learnings to convert into design decisions. If in a more traditional consumer situation, then your understanding of the sales, merchandising, and overall vendor model (with pricing too) is also useful.

Don’t get hung up on Agile or Lean: These are just process words and mechanisms for delivering code, each with their particular lexicon. They are not perfect. There is no ideal way to fit UX into either one. If the overall tenor is collaborative, transparent, and iterative, it will work out. The dynamic is complementary in spirit and should enable efficient learning-based outcomes to help iterate the product-market fit goals. The gritty, mundane details of JIRA, stories, estimations, and sprint reviews are simply part of that process. Advocate your design vision and figure out how to co-opt those mechanisms to get design ahead of the game, like filing “UX Stories” based upon your vision, rather than reacting to yet another tedious (and likely rare or trivial) “UI bug” that devours unnecessary time.

Think in terms of “goals, risks, asks” when managing up: Maybe as part of a large corporate design team it was acceptable to vent and rant about issues with close peers. However, in a design leadership role on par with CEO and VPs of Engineering or Sales, you need to be focused and deliberate in your communications with them, to amplify the respect and build trust & confidence in you. I learned it’s far more effective to discuss things in terms of your goals, the key risks affecting the accomplishment of said goals, and what actions are desired (or asks to made) to help achieve those goals. This is way more professional and valuable of a dialogue driver.

Finally, get comfortable with “good enough”: As Steve Jobs said, “Real artists ship,” meaning that you can’t sweat all the perfection-oriented details too much at the risk of delaying a product release. At some point you must let it go, knowing that there will be subsequent iterations and releases for improving imperfections — which is always ongoing! That’s part of the fun. Having fillers, stop-gaps, and temporary fixes are all expected.

Do your best and accept—if not wholly embrace— the notion of “satisficing” (per Herb Simon) of doing what’s necessary yet sufficient. This will protect you from going insane, or getting overwhelmed.

Design leadership is incredibly difficult, perhaps made more so because of the glare of the spotlight now that UX is “hot” and finally recognized by execs and boards as a key ingredient to company success. While you may be a “team of one,” or even just a few, the kinds of learnings itemized here will enable a productive, design-led path for the entire company. Good luck!

Originally published at interactions.acm.org , with more recent editorial updates.