You have the right ideas. But are you asking the right questions?

Emily Kellner
Dec 8, 2020 · 6 min read

5 ways to turn the well-timed interruption into your UX superpower

I’m a UX content strategist. And much like my peers in the biz, that means my responsibilities are wide-ranging — from high-level information hierarchy all the way down to nitty gritty choices about headlines and CTAs. I get deep in the technical weeds to understand how our tech stack works (well, to the extent that I need to understand how our tech stack works), I zoom out to make sure we’re aligned with business goals and brand values — and yes, I also write words.

But the more I do this job, the more it becomes clear that my most meaningful contributions aren’t messaging frameworks that dazzle stakeholders or snappy lines of copy that delight users. Instead, my biggest value-add is often something much less flashy: the way I show up in meetings and working sessions with my teams. As Kristina Halvorson says, the most important skill for this job is being able to ask smart questions.

So here are the top five questions (and…err…thought-provoking statements) you’ll find me asking my product design, product management, user experience research, and engineering partners:

1. “Can I play that back to make sure I’m following?”
Or: “I’d love to restate that to make sure we’re all on the same page.”

This one is all about translation. As UX content strategists, we’re plain language experts and natural empaths, which makes us uniquely suited to navigate cross-functional conversations.

Any time you’re in a room/Zoom with folks from different disciplines, keep your ears perked for technical jargon and your eyes peeled for confused faces. Maybe an engineer is talking about the complexities of an API or a designer is discussing the affordance of a component. Perhaps someone is sharing an idea that’s coming to them in realtime and the stream of consciousness is tough to follow.

The result is often false misalignment — or worse, false alignment — because folks are uncomfortable asking for clarification or unaware they need clarification in the first place.

In either case, a quick restatement can do wonders to reveal where your team is on the same page and where more discussion is needed.

2. “Can you talk me through a real-life scenario this would solve for?”
Or: “The only user scenario I can think of is _____, which seems like an edge case. Is there another scenario I’m not thinking of?”

You’ve probably been there too. A meeting starts out about one thing but quickly morphs into an impromptu propose-a-feature-palooza — and before you know it, there’s a new item on the roadmap.

Even when you are following the right order of operations and working off a spec with documented requirements and KPIs, we’ve all seen “As a user…”-user stories stripped of their humanity to the point where it’s tough to imagine a real person in the real world using the thing.

It happens even on the best of teams.

So whenever new functionality is discussed, make sure everyone has a picture in their mind of an actual human being who has a problem, pain point, or opportunity. Once you’re all imagining the same thing, you can make sure it checks a few boxes:

  • Is this a situation you expect your target audience to experience?
  • Is this a common situation for your target audience or more of an edge case?

Of course there are other boxes that need to be checked before work begins. But this line of questioning will at least get you to a place where you know whether the feature would serve the folks you’re trying to serve.

3. “It sounds like [optimal UX thing] is too expensive, but is there a way we can accomplish that same goal for less?”
Or: “Can you help me understand which aspect of this proposed design is the most expensive to build? If we only did [scaled back version of optimal UX thing], would it be meaningfully cheaper?”

One of the most common points of tension in product development is cost vs. benefit. UX pitches an awesome idea that we think will make users’ lives a lot easier. Then the engineers give an estimate, and the product manager says it’ll take way too long.

But that doesn’t have to be the end of the conversation.

Like in any negotiation, you probably led with something better than what you’d settle for — in this case, the most optimal version of the optimal UX thing. But there’s probably a way to get a similar job done with less scope. So in this line of questioning, defend the critical “nugget” — the core functionality that you’re advocating for — and look for places to compromise. Can you forgo a custom component and get an almost-as-good job done with an existing one? Can you tweak the messaging so you only need one version instead of unique variants for each user segment?

Thought partnership with your engineers and product managers makes a huge difference here. Seek to understand which aspect of the design is the most costly to build — and seek to gain buy-in about why the critical nugget is so important. With that mutual understanding in place, you can brainstorm together and find a happy medium.

4. “If the objective is to _____, then…”
Or: Can we take a minute to restate the problem we’re trying to solve?”

This one comes from a workshop our team participated in with Mia Blume of Design Dept.

Mia shared this technique in the context of giving critique in a design review. But the “If the objective is to ____, then…” phrasing also comes in handy when you’re weighing two possible design approaches with your design partner. Instead of devolving into a debate around subjective preferences for CTA placements, find common ground by aligning on the facts. What are you trying to accomplish (for the user or business) with this design? If you want users to take action, for example, then the design with the more prominent CTA is probably the most effective.

By grounding your argument in how well the design accomplishes your shared objective, things immediately feel less combative and you focus the conversation on what matters most. Plus, you’d be surprised how powerful it can be to simply say the obvious thing out loud: with the objective clearly resurfaced out in the open air, decisions often have a way of falling into place.

5. “Before we go too far down this path, can we pause to throw out a few other ideas?”
Or: “I know we’re excited about this approach, but I want to make sure we’ve explored all our options.”

Sometimes it pays to rain on your team’s parade.

When excitement is building around an idea, the temptation to get on board is strong (isn’t it nice when everyone agrees?). But if you have another idea, or you think someone else does, or you just feel like there are still some stones left unturned, it’s in the best interest of your product and your users that you speak up.

Choosing a moment to jump in can be awkward, but I try to time it when:

  • the conversation is shifting into the next level of fidelity (e.g. from a theoretical discussion of an idea to the technical details of building it or the timeline for shipping it)
  • multiple people have voiced their support and no one has expressed concern or suggested alternatives
  • the topic is about to change entirely

The key here is not to be a contrarian for contradiction’s sake, but rather to pick your battles strategically. If it’s a small decision and everyone’s on board with a path forward, nodding your head and moving along is typically the best move. But when you notice your team veering toward groupthink on a bigger decision, it’s worth pumping the brakes.


Posing thoughtful questions (and yes, sometimes even interjecting awkwardly) takes practice, just like anything else. But once you’ve got the core skills of the job on lock, learning to ask the right thing in the right way at the right time will take you even farther. And probably — for better or worse — get you invited to a few more meetings.

Want to be part of a team that writes about stuff like this? Check out open roles in Design + User Experience at NerdWallet.

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