December 6, 2019

How to Run a Website Design Discovery Interview

There’s an old saying attributed to famed inventor Charles Kettering, “a problem well-stated in half-solved.” In life and in marketing, there is often a surprising lack of well-stated problems, which results in organizations wandering the desert in search of a miracle solution.

When you’re working on designing a new website, either internally, as an agency, or as an independent consultant or freelancer, the first phase of the project is the discovery process — where you will define that problem and its elements. During this phase your job is to be part investigative reporter, part Hoover vacuum. You want to get to the bottom of the story and to absorb as much information as you can in the process.

We start every project with a kickoff discovery interview that includes internal client stakeholders. When most effective, this meeting includes our direct client contacts, as well as members of the organization up and down the food chain. To keep things flowing you don’t want more than 5–10 people in the room, but you do need to make sure that you include individuals who have unique customer insight as well as those who have approval authority on the final product. Involving those with veto power now will make for a better process and a better result.

Regardless if it is tourism, corporate, publishing, non-profit, or any other vertical, there are always four main areas we look to investigate during a website discovery interview: users, experience, organization, and process. We purposely order our conversation this way to keep the energy up and the focus in the right place: users come first.


In the first part of our discovery interview, we want to define what the buckets of users are on the site, and what are the priorities for each one. Most organizations will have 1–2 primary user groups, generally customers, students, voters, etc. that will be the focus of the website. However every organization serves more than just their core audience, and it is vital to consider secondary groups like prospective employees, media, regulators, or investors in the design as well.


Once we define the audiences, we’ll then begin to investigate the needs each group has from the website, and also how they are interacting with the site (what devices are they using, how are they finding the site, etc.). We also want to know what message the organization wants to sent to each of these groups, what actions we want these visitors to take, and what things “have to” be included on the site but are not part of the primary journey.


Now we begin to shift the focus inwards, and we want to know how this new website fits into the overall goals of the organization. What is the client looking to achieve and how could the website help them get there? Here, we also ask about “sacred cows and third rails,” things that need to be part of a new website design and things that should be nowhere near this project. Lastly, we ask who else we should speak to about this project.


We conclude with the process conversation, where we ask some of the more awkward questions: What could go wrong with this project? What are your hopes and worries? During this segment, we make sure to again ask who is giving final approval and who else needs to have input in this project. Extracting honest answers here helps everything go much, much smoother.

This interview is only the beginning of the discovery process. From your learnings here, you’ll likely have a list of individuals or groups that you now need to schedule follow-up conversations with. And while conversations are great, don’t stop there — you may want to do site visits, tours, shadowing, historical research, user tests, and other digging to help you build a more complete understanding as to who the users are and how they use this website. We’ve stood on the concourse at Grand Central Terminal flagging down tourists, interviewed elementary school aged musicians, and gone on boat tours around Manhattan in our pursuits to build the right site for our clients. To be honest, this is often the most fun part of the whole process.

The more relentless you are in pursuit of understanding the user, the better the end product will be. You’ll never truly be finished with discovery, but once you’ve reached a comfortable level of knowledge you can begin to synthesize it all into key insights and ultimately website specifications, designs, and a winning finished product.

About the Author

Ben Guttmann ran a marketing agency for a long time, now he teaches digital marketing at Baruch College, just wrote his first book (Simply Put), and works with cool folks on other projects in-between all of that. He writes about how we experience a world shaped by technology and humanity – and how we can build a better one.

Get my new book, it just came out.

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