Karen, an assistant to one of Side’s top-producing agents, rummaged through a pile of paperwork until she pulled out a checklist of tasks she put together for a home for sale. She paused for a moment, and crossed “property inspection” and “photographers” off the list. I asked, “How did you know those tasks were completed?” She simply smiled and pointed to her head.

We’ve seen this pattern repeat across many of our agent partners and their assistants. Agents’ lives and workplaces are organized chaos. They have physical or digital artifacts to alleviate some of the mental load, but the source of truth is all in their head. When working on two to five properties, each with over 10 tasks and dates to keep track of, transferring that much knowledge to other team members can be stressful and time consuming.

We learned this insight by conducting contextual inquiries, a research method that’s worked very well for us at Side.

What is a contextual inquiry?

According to UXPA’s Usability Body of Knowledge, a contextual inquiry is a semi-structured interview where you observe a user in their own environment, asking questions as they work to understand the motives behind their actions. The goal is to help companies see how users engage with their product and get insight into how they can develop products that fit into a user’s daily life.

Contextual inquiries rely on a master-apprentice model, where the user is the master, and the interviewer is the apprentice. The apprentice goes to the master’s place of work to learn about their tasks, and understand why they do things the way they do. It’s very important that the apprentice begins a contextual inquiry with no assumptions, so it’s essential to probe and ask questions during the observation phase.

Why a contextual inquiry?

The key benefit of a contextual inquiry is that it’s conducted at the user’s workplace where you’re able to collect much richer data than you would if the interview were performed at your office or a neutral location. You get a closer, more intimate view into how users interact with your product in their daily working environment, which then lets you pick out small nuances in their actions that might result in a new insight or seeing a gap you didn’t notice before.

Guiding principles

Keep these four principles in mind as you plan and run your own contextual inquiry:

Focus : Having a clear purpose with defined goals is important during the interview phase as you’ll need to steer the session to address the areas you want to focus on.

: Having a clear purpose with defined goals is important during the interview phase as you’ll need to steer the session to address the areas you want to focus on. Context: Visit your user’s workplace to observe and learn how they work.

Visit your user’s workplace to observe and learn how they work. Partnership: As you observe the user, asking questions when you don’t understand something will help you better grasp their motives and get clarity on hard-to-explain areas of their work.

As you observe the user, asking questions when you don’t understand something will help you better grasp their motives and get clarity on hard-to-explain areas of their work. Interpretation: The goal by the end of the session is to have a shared understanding with the user about their work.

How to get started

Before meeting with your users, doing some upfront planning will ensure you maximize the value you get from your contextual inquiry. These tips will help get you started:

Discuss with your team what you want to get out the contextual inquiry and create an agenda that includes topics you want to focus on to help you stay on track during the session. At Side, we also prepare interview questions to ask after the observation phase for extra clarification.

to help you stay on track during the session. At Side, we also prepare interview questions to ask after the observation phase for extra clarification. With your focus in mind, select a representative sample of your users for the study. A typical representative sample is four to six users. Run enough contextual inquiries so you can begin to see patterns develop.

for the study. A typical representative sample is four to six users. Run enough contextual inquiries so you can begin to see patterns develop. Practice makes perfect . Conducting a dry run of your contextual inquiry with a volunteer at your office will help you get a good flow for the real thing and give you an idea of how long the actual session will take.

. Conducting a dry run of your contextual inquiry with a volunteer at your office will help you get a good flow for the real thing and give you an idea of how long the actual session will take. Finally, when you’re actually in a contextual inquiry, let the user do most of the talking while you probe. Remember to guide the conversation to cover all of your focus points. Leave no stone unturned!

Interviews to insights

You’ve completed your contextual inquiries … now what? There are many different ways to distill your notes into actionable insights, but we’ve adopted the IDEO method (part 1, part 2) of synthesizing notes.

After each contextual inquiry, the interviewer and observers “download” their notes by taking 10 minutes to extract the most important points from the session and record them onto color-coded Post-Its: yellow for facts about the workflow, red for problems, purple for ideas. Once all the notes are converted to Post-Its, they’re read out loud and attached to a poster board full of notes for each “master.”

Our next step is to place all the poster boards side by side and start grouping relevant notes to help us identify common themes. We then organize the smaller groups into larger groups, making sure the bigger groups tell a coherent story across many users. Those larger groups of notes are what ultimately lead us to our final insights.

Delivering value

If you’re unsure about what to build next, take a step back and let your users answer that question for you. If you want to build a product that delivers value and solves your users’ problems, you need to talk to them. At Side, even with constraints on time and resources, getting to know our users is a top priority.

So get out there, talk to your users, and build something that matters.