Interviewing Leaders to Uncover Potential UX Problems

Organizations have lots of problems, and they hire smart people like you to help them solve those problems! Whether you are starting as a consultant or the newbie, or you’re a seasoned employee looking to take a fresh approach, one technique you can use is to interview leaders within the organization to gather insight into their objectives and opinions, and ultimately better understand the landscape of the business and its audience (e.g., customers, users, etc.).

Questions to Ask

As you interview leaders within an organization to better understand – at a high level – potential user experience-related problems to tackle, use this Interview Worksheet to list the questions you want to ask. Plus, you may think of more categories and questions to add!


A good place to start is to ask questions about the organization’s history. Warm up the conversation by asking about some of the organization’s recent “wins” – anything from the conclusion of a year-long project to a PR piece that attracted national attention. Be sure to ask about failures or specific areas for improvement that they’ve recently identified. Oftentimes, you’ll pick up clues that will help you transition to your next line of questioning – values.

Examples: In the last year, what are your organization’s biggest “wins”? In the last year, what areas for improvement have you identified?


Based on the “wins” that leadership shares with you, ask questions around the underlying values that cause the organization to consider them “wins.” For example, if the conclusion of a year-long project was cause for celebration, then why that particular event was important, and what kept everyone motivated to achieve it. Use this same technique to discuss areas for improvement as well. Another way approach to uncover an organization’s values is to ask questions in the context of its audience.

Examples: What are the values that keep you motivated? What are the key points you want to communicate to your audience? What kind of action do you want to inspire in people?


Now that you have an idea where organization has been – as well as the values that form the foundation – you can frame the conversation about where it is going and provides context for understand the organization’s goals. In your interviews, leaders may provide specific corporate OKRs (objectives and key results), or even S.M.A.R.T. (specific, measurable, achievable, results-focused, timely) goals, but your questions should dig deeper to uncover the vision for growth and success.

Examples: For this year, what are your top 3 organizational goals? What would a successful year look like for your organization? Which specific milestones would be achieved to consider this a great year?


In order to make good suggestions, you need an accurate assessment of the resources available to the organization. The solutions that you will later outline must be realistic within leadership’s means – budget, time, people, skill sets, technology, and even motivation. Asking leaders to think about what’s available and what’s lacking can also give you insight into which resources they covet and which they overlook, and could lead to uncovering untapped potential.

Examples: What kinds of skills and technology are available to your organization? What are your core strengths as an organization? What kinds of resources do you think you are lacking?


Ask questions about all users connected to the organization – direct customers and prospects, affiliates, internal stakeholders, and indirect influencers – to learn how the audiences are currently segmented and the methods used to communicate with them. There may be other personas or more granular segmentation that leadership has not considered, and those audiences could benefit from unique experiences.

Examples: What do you already know about your audience? What are the ways you communicate with your audience?


Soliciting good feedback is tricky, because people often a) tell you what you want to hear to be polite; or b) only speak up to complain. Focus your research on the ways that the organization obtains feedback, as well as the actual feedback received. Can you spot themes among the responses about different aspects of the products/services, or the methods and messages of communication? Consider the characteristics of the individuals providing the feedback. In which segment or stage of the funnel (prospect to long-time customer) are they? Is there a correlation between respondent characteristics and their feedback? What potential experience issues can you uncover?

Examples: What has your audience told you about the way you’ve engaged with them? What has your audience told you about the products/services your organization provides?


Move into uncovering leadership’s assumptions about their audience and products/services by asking what conclusions they inferred from the feedback they’ve received, and whether they took any action based on that information. Compare that to your interpretation of the feedback. Continue to probe into what they ‘know’ about their customers or prospects, and what evidence they have to support their assumptions.

Examples: How do you think people want to engage with you? What kind of information do you think people want to know?

Now go create some awesome experiences!

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