Navigating the Awkward: A Framework for Design Conversations

We’ve all been there. A client or coworker shows us this amazing thing they (and maybe their entire team) have worked on for hours or weeks. They are so proud of it. It’s new or maybe it just looks new. They may or may not ask you what you think—but you’re there to experience it. And your brain quietly screams.

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As an experienced designer, you often have an intuitive reaction and can quickly spot bad designs; they may be visually incongruent, poorly structured, confusing, lack social awareness, or look like they are trying too hard.

If your initial response is so negative that it slips through into your expression or voice or body language, it can completely sabotage any possibility of buy-in. And, far more seriously, it can ruin the relationship of trust and collaboration you’re building with that person. 

Reflecting on my own successes and failures—and the experiences of others—I’ve put together a conversational framework for navigating these all-too-frequent design interactions, whether you’re an in-house designer, a consultant, or an agency employee. 

Be a relationship steward#section2

“Getting things done” is often accomplished at the expense of relationships and sustainable design solutions. As in, the “We need to manage this situation” approach (emphasis on the “manage”) quite often looks more immediately effective on paper than the “We need to be productive while stewarding this project for this partner” mindset.  

The thing is, a design stewardship mindset to working with clients/partners is a better bet; thinking beyond buy-in or proving your point or getting your own way pays off in both an immediate situation, and long-term, for both sides.

I’ve had plenty of those “design conversations gone wrong” over the years, and have noticed a common set of whys and hows behind the scenes. To help me consciously factor them in and stay focused, I’ve developed this simple conversational framework:

Element 1: Move from selling to helping.

Element 2: Question your triggers and explore the problem.

Element 3: Map the problem to the client’s values.

Element 4: Formulate questions for the client based on values.

Element 5: Listen and be prepared to challenge your assumptions.

Element 6: Reflect back on the problem and share recommendations with the client.

We’re going to explore all that below, but here’s a quick reference version of conversational frameworks you can look at as we go.

Healthy self-talk#section3

When confronted with a bad design, there are some common reactions a designer might have—what we often catch ourselves saying in our head (hopefully!) or directly to our clients. (I need to preface by saying I borrowed some of these from a viral “Hi, I’m a …you might know me from my greatest hits…” on Twitter.)

  • You are not your users!
  • Blindly following another organization’s best practices is not going to guarantee successful conversion for your business.
  • Have they ever heard there’s such a thing as Calls to Action?
  • Really, you couldn’t have bothered to tell the user ahead of time how many steps this process involves?
  • No, a chatbot won’t magically fix your horrible content!
  • Is this clipart?!!
  • Don’t use your org chart for navigation…not even on your intranet.
  • You can’t mix apples and oranges.
  • Views do not equal engagement metrics!
  • Stop celebrating outputs instead of outcomes!
  • Diversity is more than just white women.
  • You’re talking about implementation details, but I still don’t even know what problem we’re trying to solve.
  • Not another FAQ!
  • Does accessibility mean anything to these folks?
  • We don’t need 15 unique designs for this button. There is a style guide for that!
  • Good luck with your SEO efforts; keyword stuffing won’t get you ranking!
  • Can we start designing experiences instead of pages and features?

I am sure you can relate. While there’s nothing inherently wrong about these statements—and there are times when it is worth being upfront and saying them as-is—we also know they might be ineffective, or worse yet, perceived as confrontational. 

Someone worked hard on this. They put a lot of thought into it. They love it. They want this to be the solution. 

So, how can we avoid defensiveness? How do we engage the other person in a meaningful conversation that comes from a place of empathy instead of arrogant expertise? 

In describing “How Shifting Your Mindset Can Ignite Transformation,” Keith Yamashita points out that “each of us comes into the world curious, open, wanting to bond and wanting to have great connections with other people,” yet “our training, societal norms, school, and early jobs beat all of that out of us.” Self-awareness and inner reflection are essential to helping us reconnect with other humans. Practicing mindfulness is a great way to develop and enhance these skills.

It’s not me, it’s you (Element 1)#section4

First step to getting your message across is shifting your position from “How do I share my perspective” to “How can I help my (clients/partners/coworkers) improve their current product?” 

Make room for the needs of others and create some distance from your ego and. In particular, try to refrain from saying what you find so intuitive, as well as delay providing your opinion. 

Blair Enns, who writes about the importance of being a vulnerable expert, says it beautifully (emphasis is mine):

  • You can be slick or the client can be slick. It’s better if it’s the client.
  • You can fumble and be awkward in the conversation or the client can fumble and be awkward. It’s better you are the awkward one.
  • You can have all the answers to the client’s questions or the client can have all the answers to your questions. It’s better to ask the questions. (Nobody has all the answers.)
  • Those who are not trained in selling often think of the cliches and think they must be seen to be in control, to have the answers, to have the polish. The opposite however is better. You can still be the expert by showing vulnerability. You don’t need to manufacture answers you do not have. It’s okay to say “let me think about that.”

Allowing others to be in the spotlight may take some practice and requires you to be self-aware. When you find yourself triggered and itching to comment or to disagree with something, try the following exercise:

  1. Pause.
  2. Acknowledge that you are frustrated and want to jump in.
  3. Invite yourself to be curious about the trigger instead of judging yourself or others. 

The more you practice this kind of self-awareness, the more you’ll notice your triggers and change how you respond to them. This quick mental exercise gives you the space to make an intentional choice. For similar practical strategies, take a look at “How to Turn Empathy into Your Secret Strength.”

Winning the moment isn’t a win (Element 2)#section5

One potential trigger may be rooted in your mindset: are you more focused on trying to get “buy-in,” or on building positive, lasting relationships to support ongoing collaboration and stewardship?

To do this, you need to first ask yourself some questions to get to the bottom of what your impulse is trying to communicate. You then need to do some slow thinking and identify a question that will engage your partner in a conversation.

Here’s a hypothetical situation to explore what this might look like.

You’re shown a very clunky, centralized system designed so users can register for recreational activities around the city. The client wants your team to create a chatbot to support it. 

Your internal reaction: “Instead of pages and features, can we start designing experiences?”

Analyzing your reaction:#section6

Why?#section7

When we focus on pages and features like chatbot solutions, we typically aren’t seeing the whole picture.

Why?#section8

Organizations can get distracted by a shiny opportunity or single perceived problem in a product, but these can frequently overshadow where real impact can be made. 

Why?#section9

The 80/20 Pareto principle has a strong pull for many organizations.

Why?#section10

Organizations want solutions that take minimal perceived time and effort.

Why?#section11

Organizations want to save money/go with the cheaper option. 

So what?

As a result, organizations risk prioritizing what seems to be the easy thing at the expense of other, more user-friendly and profitable solutions. 

This example is simplistic, but notice that by asking a few sets of questions, we were able to move from a reactive statement to a reason why something may not be working—a reason that’s a lot less emotional and more factual. You could use a modified 5 Whys approach like this, or some other questioning method that suits the situation. 

If you dissect our example more closely, you’ll see that unlike the initial reaction, which speaks more to design elements like pages and features, we are now talking about more broadly relatable topics across business lines, such as cost savings or risk assessment. Structuring your conversation around topics most familiar to the other person and reflecting their core values can help us be more successful in improving their product.

Ask with values in mind, close with opportunities (Element 3)#section12

I recently attended an excellent event on “Speaking Truth to Power,” presented by the Canada School of Public Service. The keynote speaker, Taki Sarantakis, shared his strategies for how to be an effective expert and advisor, such as:

  • Be credible and build trust
  • Have humility and empathy
  • Make sure that the person you are advising understands that the advice they do not want to hear is for their benefit.

He also broke down a few concepts that could be a barrier to implementing this advice. If we see ourselves as “speaking truth to power” we are likely making a values judgement. We believe and project to others that we have all truth and no power, while the person on the other end has all the power, and no truth. It’s an arrogant position that weakens our ability to make any productive progress. Framing our interactions as a battle will likely result in a lose-lose situation.  

Sarantakis then presents an example conversation that is rooted in credibility and humility, and comes from a place of care. He underscores that any advice you choose to share has to absolutely come from a place of concern for the person making a final decision, and not from a desire to show off and say so on record. It roughly looks like this:

  • Here is what you need to know…
  • You know X, but you may not know Y and Z.
  • I know this is something you may not want to hear, but I need to say it because it is important that you know this.

As part of the panel discussion that followed the keynote, Kym Shumsky, who has lots of experience advising senior leaders, reinforced Sarantakis points by stating that valuing truth, knowledge, and accuracy over relationship-building can be detrimental. Thinking back on my personal experiences, I fully agree. 

So how do we build trust, credibility, and share from a place of care? Steve Bryant, Head of Content at Article Group, has some thought-provoking words on this in his article “Make relationships, not things”:

Relationships are based on trust. Trust takes time and honesty. You can’t just create a pile of content and be done with it. You can’t “thing” your way to people trusting you.

Which is to say: the question isn’t what content to create.

The question isn’t how to create that content.

The question is why do you care about the people you’re creating the content for? What makes them special? What kind of relationship do you want to have?

How do you want them to feel?

Translating core values into specific needs (Element 4)#section13

Going back to the exercises we just explored and what we think could be the source of the problem, it’s time to start moving backward from the core values to specific design characteristics that need to be addressed.  

You have to always start the conversation as a set of questions. Beginning with questions allows you to set aside the expert hat, be curious, and let the client share their experiences. It shows them you care and are there to listen generously

Build rapport, be present, and be there to listen (Element 5)#section14

Erika Hall offers timeless advice about the need to build rapport and understand our partners in her article “Everyday Empathy”:

And as social science shows, trying to bridge the gap with facts will never change anyone’s mind. The key is to value — truly value — and reflect the perspective of the people you want to influence. […] Attention is a gift beyond measure.

A great bit of advice on “being present” rather than “presenting” on a topic is offered by Blair Enns (author of The Win Without Pitching Manifesto) in the episode “Replacing Presentations with Conversations.” Being present also means being vulnerable and open to discovering something new that might change your initial reaction. 

And then be prepared to truly listen, not convince. Sarah Richards points out how important it is to understand the different mental models that partners bring to the table and work together to form new ones to accomplish common goals:

How many times have you said you are going to talk to someone who is blocking you? Now count how many times have you said you are going to listen to someone who is blocking you? When we have someone in our organisation who disagrees with us, we go to see if we can convince someone that our way of thinking, our way of doing things, is the best way of doing it.

Here is what a conversation relating to “Can we start designing experiences instead of pages and features?” might look like, if we follow this approach:

You: What do you hope to accomplish with a chatbot?

Partner: We want people to get answers to their questions as quickly as possible, so they can register and pay for local recreation activities of their choice faster. We live in a beautiful city and it’s a pity when residents and visitors can’t take advantage of everything it has to offer. 

You: What have you heard from the people who experienced barriers to quickly registering and paying?

Partner: They complain that they can’t easily find activities in community centers closest to them or that there is no way for them to see all current and upcoming classes around the city at a glance, or that additional information about different activities is not provided within the system and they often have to look up events or class instructors separately to find more information on other websites. They also are not able to browse all activities by type of recreation, like “nature” activities, which might include hiking, city tours, birdwatching, garden events, and festivals. They often do not know what terminology to use to search for events and activities, so they say it is difficult to find things they already do not know about.

You: How do you think this makes them feel?

Partner: They say this frustrates them, as information on other websites might differ from the information in our system and they end up wasting their time guessing which one is correct and up-to-date. They then end up having to call the community center or organization providing an event for more information, to figure out if it is a good fit, before registering and paying; which significantly delays the process. 

I think you see where this is going. 

Here are a few more follow-up questions:

  • Have you tried registering for an activity using the system? How did you feel/what did you experience? 
  • What would you like people using your system to feel/experience?
  • You’ve mentioned a number of barriers that people experience. How well do you think a chatbot will be able to remove these barriers now?
  • What are some of the risks you foresee in trying to solve these problems?

At this point, if you hear something that makes you pause and question your assumptions, ask further questions and consider going back to the drawing board. Maybe you need to ask yourself: What are my lenses?

Respond with care and invite collaboration (Element 6)#section15

If what you’ve heard confirms your assumptions, you could offer a few concise, summative statements and a recommendation. Whatever you say needs to integrate the vocabulary used by the client (mirroring), to show them that you were listening and critically reflecting on the situation. 

Let’s see how that might look:

“Based on what you’ve shared, it seems that you want to make it quick and easy for anyone in the city to discover, decide on, and pay for a local recreation activity. The experience of the people using the system is very important to you, as you want them to enjoy the city they live in, as well as support the vibrancy of the city economically by registering and paying for local activities.

If we want to help people enjoy and experience the city through events and activities, we need to make it simple and frictionless for them. The barriers they experience cannot be solved with a chatbot solution because the information people are looking for is often missing and not integrated into the current system in a meaningful way. So the chatbot would not give them the answers they need, creating further frustration. 

Adding a chatbot also creates an extra layer of complexity. It does not solve the underlying cause of frustration stemming from lack of relevant and integrated information. Instead, it leaves the current experience broken and creates yet another place people need to go to for possible answers.

It would also be a huge risk and time investment to design a chatbot, as your current content is not structured in a way that would allow us to have useful information extracted.

Given your time and resource constraints, I would suggest we explore some other solutions together.” 

Framing and reinforcing the conversation#section16

To recap, here are the six essential elements of the conversational framework:

Element 1: Mentally move from how you can share and sell your perspective to how you can help your partner.

Element 2: Ask yourself probing questions to better understand your reaction to the “bad design” trigger and what is at the core of the problem.

Element 3: Map the core of the problem to value(s) you can use to begin the conversation with a partner.

Element 4: Use value(s) identified to formulate and ask questions.

Element 5: Get ready to truly listen to your partner and be prepared to challenge your assumptions.

Element 6: Review your responses to probing questions and identify recommendations you can share back with the partner.

This conversational framework starts with us as individuals, forces us to critically deconstruct our own reactions, then asks us to reframe what we find from a perspective of what matters and is known to our clients. It reminds us that we should learn something in the process by having intentional yet open conversations.

Future of design leadership is stewardship#section17

The work we do in the web industry touches people—so we need to be people. We need to be human, build trust, and sustain relationships with our clients and partners. If we aren’t doing a good job there, can we really claim it’s not impinging on our designs and end users?

Our growth as web professionals can’t be limited to technical expertise; design leadership is stewardship. It’s rooted in listen, then respond, in learning how to pause, create space, and get to the root of the problem in a productive and respectful way. We need to learn how to intercept our reactions, so that we can shift how we approach triggering situations, stay still and listen, and open up conversations rife with possibilities, not progress suppressors. Guide clients toward better design choices by meeting them in the moment and partnering with them.

In design work, being a steward does not mean that you should push to get your way. Neither does it mean you should indulge clients and create broken or unethical products. Rather, it proposes an attuned way of approaching potentially contentious conversations to arrive at a solid, ethical design. It is about framing the conversation positively and ushering it as a steward, rather than stalling discussion by being the gatekeeper. 

About the Author

photo of Ksenia Cheinman

Ksenia Cheinman

Ksenia Cheinman is passionate about improving public services through content. She often ends up in roles with the words “architect” and “strategy,” which may explain her interest in systems thinking. When not building partnerships and learning by reflecting, Ksenia likes to knit, ponder in French, and design her next tattoo.

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