The Art of Asking Questions

In my past life as a design consultant, before anything else came strategy. While the following is written in the context of project work, these same techniques can easily be appied to product work.

As designers, our job is to understand problems and create appropriate solutions that can be quickly and clearly understood by others. But how exactly do we start to do that?

Kick off every project — no matter how big or small — with a Discovery session. Everyone involved in making decisions regarding the project is invited and we usually spend an hour or two together talking about anything and everything related to their organization, their customers or clients, products or services, and, most importantly, the project goals.

Getting people to give us the information we need — even when we don’t know what that might be — is partially about knowing when to stop talking and listen but mostly about asking the right questions. Here’s how we go about figuring out what those questions are.

The Process

While specific questions vary from project to project, we always follow the same arc of “zooming in:” starting off by asking general questions until we understand enough to come up with more specific ones.

We repeat this process with as many people as we can — both internally (others within our client’s organization) and externally (our client’s customer) — until we’re comfortable making a recommendation on how to proceed.

Depending on the type of project we’re doing, our recommendations could take many forms — how to structure content on a website or in a print piece, what the visual direction of an identity system should be, or what language a brand might use to talk to customers, to name a few.

We write up everything we learn along with our recommendations on how to proceed into a Findings and Recommendations document that we refer to throughout the project. It’s usually a little dry because we don’t want to start suggesting exact design solutions or copywriting yet, but it helps set everyone’s expectations and ensures that the rest of the project will go smoothly by clarifying that we heard everything correctly and making sure our client is comfortable with the direction we’re considering.

Getting Prepared

Before we do a Discovery session, we like to familiarize ourselves with the sector our client is in, review their competition, and research their organization as though we’re prospective customers.

We always take note of what we come across and jot down questions we have along the way because at the start of our research, we’re in the same beginner’s mindset as our client’s audience will be. If we have these questions now, it’s likely that someone coming to a website for the first time or picking up a brochure will have the same questions — and be searching for those answers. If we can provide them quickly and clearly, we’ll have a better chance of catching their attention and giving our client the opportunity to tell their story.

Understanding Our Client

As we go into a Discovery meeting, we know our job is to represent the audience. If we don’t think they would understand something, it’s our job during this process to clarify it so we can present it in a way that makes sense to them.

The first thing we make sure to understand before we dive too deep into our questioning is the goal of the project. Does our client want to sell more product? Raise brand awareness? Attract a certain type of customer or get funding?

Even more important is understanding why our client does what they do or, to put it bluntly: why do they exist? At this point, we’re trying to figure out what drives them because we want to capture their excitement and transmit that to their audience.

To do that, we try to suss out what their differentiator is — why would a prospective customer choose them over a competitor? If our client is asking for time or money from someone, what would make them pay attention or open their wallet?

It's also important to note that the type of project we’re working on — a logo, a website, a book, etc. — informs the questions we ask. We probably don't need to know how tech savvy our client's audience is if we’re designing a logo but that would be quite useful to know if we’re making an e-commerce website.

We don’t expect to become subject matter experts overnight however, with some research, we’re usually able to reach an advanced-beginner or intermediate level pretty quickly. We know we’re in good shape when we understand the common lingo in our client's industry and understand what excites people about the area we’re researching.

Interviewing the Audience

Whenever possible, we try to interview our clients' ideal customers or favorite clients. We like to set the stage for them by explaining who we are (a third party helping a client), what we’re hoping to achieve with the project (make more customers like them or build up a helpful support section, for instance), and make clear that the conversation is private. Not only does this lend a frame of reference for our questions, it helps whoever we’re talking to feel like they can speak freely without fear of offending anyone.

It’s also important to learn where our interviewees are coming from so we can understand the context of their answers, that way we’re able to tailor our questions to make the most of our sessions.

We always go into an interview with a list of questions informed by our research but we’re not concerned with checking them all off. At this point, we don’t know what we don’t know and by following the flow of a conversation, we may end up uncovering something more interesting than we anticipated. If we hear something that’s especially insightful or important to the task at hand, we try to pull on that thread. The most helpful information is usually a few layers deep in someone's mind — things an expert might write off as obvious might help a novice connect the dots — so we keep asking “why” until we find the central point of each thought.

As we’re talking to people, we make sure to give them the time and respect to complete their thoughts but we aren’t embarrassed to ask for clarification if there’s something we don’t understand. We also try to show our interviewee that we’re interested in the subject matter and are excited by what we’re learning. A conversation is a two-way street and the energy we put in is usually returned in the form of helpful insights.

Summing It Up

While we try to take detailed notes during Discovery meetings or interviews, they typically make for a poor reference so after every conversation, we write up a summary of our impressions, main takeaways, and any context that qualifies what we’ve learned.

The goal of this phase is to learn how to take the audience from introduction to understanding in a way that feels effortless to them. By the time we’ve completed all of our meetings, research, and interviews for a project, we’re usually able to recognize some trends which help us distill the themes that will inform the rest of the project including messaging, look and feel, and layout. Further, we’re pretty much able to anticipate what the audience will want to know and when.

When working on our recommendations or the end product, we like to keep in mind that the audience isn’t captive. We know we have to earn their attention and we do that in part by being respectful of them and their time — helping them accomplish something or solve a problem they have as quickly and easily as possible.

Practicing Our Art

We’re always trying to improve our own question-asking skills and one way we do this is by listening to great interviewers. They’re easy to identify because they can talk to almost anyone about anything and the conversation is captivating.

Some people we consider to be great interviewers are Rachel Maddow, Ezra Klein, and the duo of Jessica Helfand and Michael Bierut on the The Design of Business Podcast. If you get a chance to listen to any of their interviews, pay attention to how the questions are asked, the pauses for clarification, and how follow-up questions add important context to the information being shared.

Asking questions is truly an art and like anything, you get better at it with practice. If you have questions about asking questions, I’d be happy to answer.