Key Questions to Ask During a Discovery Session

When you decide to undertake a new project, you have to start by discovering your client's ecosystem: context, activity, stakeholders, tools, their userbase, and their habits, etc.

Planning a discovery session with your client is a preliminary phase that involves researching and identifying their problems, clarifying their goals/priorities, and matching them around a shared vision of the proposed solution. It will allow you to effectively identify the universe you operate, which will help you define the userbase needs, aligning them to your client's goals.

The discovery phase's real purpose is to ask your client teams to bring their knowledge and aspirations to the table in asking the right questions: those who will lead to the exemplary information architecture, the right design, the right strategy, in few words, the right digital experience.

As designers, we will have to adopt a user-centric approach, which requires showing empathy then asking the right questions.


It is a legitimate question: why show empathy and put yourself in the userbase shoes when it is possible to directly create the solution you think is better for your client?

The answer is as follows: being empathetic not only allows you to free yourself from any bias (and therefore to be as objective as possible). It will enable you to collect as much useful information as possible to design a definitive solution meeting the userbase needs, and above all, ensuring that you and your client base your agreement on a mutual understanding of what must be achieved.

You cannot expect your clients or their userbase to lay everything out on the table for you. Even the most organized clients cannot possibly present a 100% crystal-clear picture of what they need. Our role as designers is to facilitate and guide this process, focus where necessary, and avoid unproductive traps. This doesn't happen magically; one must come prepared.

The ability to ask meaningful questions is a fundamental skill that designers often overlook. A clear correlation is established between the designer's number of questions throughout the project and the finished product quality. The answers you collect will constitute the essential keys to the successful completion of the project.

It's not just about creating; it's about understanding! The answers to the questions you ask will provide the solutions to the problems you will face every step of the way. When working with clients who have a userbase, you will have to make sure you put yourself in both of their shoes to resolve any problems. It also helps to get in touch with specialists in the sector to sharpen your knowledge.

Here is a (non-exhaustive) list of 100 questions to ask your clients to understand their project and create a better user experience. These questions will help guide the conversation and keep the team focused.


To align the different actors around the project, you need to ask general questions to understand your client's company's ecosystem. Ask your client to explain their activities in detail: what are their services, what makes them different from their competitors, etc.

Discovering their business environment is very important as it provides background information that's essential to the project. It is up to you to decide how deep you can lead your research. Useful information can include a brief history of the company, its size, the number of employees, turnover, the different services (described in detail), significant achievements, etc.

You can avoid jumping to solutions by focusing on the underlying issues and ideas that can give you or your team solid background knowledge to design the project. You can ask the following questions during the discovery session:

  1. What is the purpose of the website?

  2. Who are the primary decision-makers of this project?

  3. Who are the users or the customers?

  4. Why is this important to them?

  5. Why do they care?

  6. What are their weak points?

  7. What are the users trying to do?

  8. What is the problem or need that we are looking to solve?

  9. To better understand your users' pain points, do you have customers we can speak with regarding your product?

  10. What is your business model?

  11. What is the business opportunity? (lead acquisition, sales, referral, showcase, information, etc.)

  12. What are the key performance indicators (KPIs)?

  13. How does this website fit into the overall strategy?

  14. Are there any constraints (technological, commercial, etc.)?

  15. How are we better than our competitors?

  16. Are there any relevant sites we can review?

  17. Is there any documentation already (personas, user feeds, etc.)?

  18. Do brand guidelines exist?

  19. Does a style guide exist?

  20. Who are your biggest competitors, and what are your concerns?

  21. How do you hope to differentiate yourself?

  22. How do you see this site next year or in 5 years?

  23. What motivates you the most towards the users?

  24. What assumptions do you think you are making about the users?

  25. What do you know for sure about the users?

  26. What are the most common problems faced by the users?

  27. How will you, personally, define the success of this project?

The next step would be to identify the key audiences you need to appeal to in order to reach your objectives. Another useful thing to consider is the priority of these audiences. It would be best to discover what they want to do on your client's site alongside what your client wants them to do. Describing your client's ideal customers will help you understand who is your real target audience.


During large-scale projects or with a strong social impact (for example, government sites, non-profit organizations, etc.), it is common to forget about the stakeholders (the people or organizations with a vested interest in your client's business and the project). However, they are often key players, either directly involved in the conduct of operations, or impacted by the issue, the choice or the implementation of the digital solution to be designed. It is, therefore, necessary to identify these stakeholders (and their representatives) who will be affected by the strategic orientation of the project, as well as those who can bring exploitable insights on the table (data to be used, sectoral perspectives, etc.).

On this occasion, a more formal meeting of selected stakeholders can be organized at the start of the project to compare points of view and reach a shared conception of the strategic objectives. The discussion should then revolve around the vision of the project; its objectives, challenges and common criteria for success. And not potential solutions in terms of functionality or content, which are the prerogatives of your initial client.

To make this meeting as productive as possible, it is essential to involve stakeholders in the production process, in particular via UX ideation workshops (example: establishing an ecosystem of entities and interests) or iteration ( example: organize user tests of the existing digital solution). To begin this conversation and better understand your clients' market, you can ask the following questions :

  1. What is your interest in this project?

  2. What is its impact on you or your organization?

  3. What are you worried about in this project?

  4. Who could be affected? During the project? After the project?

  5. How have you been implied in the project before?

  6. Did it work or didn't work? What went wrong in this case?

  7. What is the reason why we should undertake this project?

  8. Who benefits the most?

  9. What is the role of this project in achieving your own success?

  10. How will you define the success of this project?


To avoid the risks and unnecessary expense of creating a project that users won't use, you must start by understanding their goals and weaknesses. The answers to these questions can give you the essential "why" behind a user's behavior. Observation results can supplement these, beware, what users say and do may be different. Analyzing their behavior can be much more revealing to build a better user experience. You can ask the following questions during the discovery session:

  1. What does a typical weekday look like?

  2. Tell me about your role in your business.

  3. What are your daily responsibilities?

  4. What are some of the apps and websites you use the most?

  5. How do you currently manage such and such a problem or task?

  6. With this project, are you looking for a solution/an alternative to a particular problem or task?

  7. Tell me about the last time you tried to solve this problem or that task

  8. How do you think our solution could help you?

  9. Can you tell me about your most notable experience/interaction with the existing solution?

  10. What do you like/dislike about the existing solution?

  11. How does this problem affect you?

  12. How did you solve/work around this problem?

  13. What is most difficult / most frustrating about the existing solution?

  14. If you had a magic wand, what would you change?

  15. Could you describe the ideal product/experience…?

  16. What would your friend/partner/colleague think about this?

  17. Is there anything you would like to add?

  18. Do you want to talk about a specific topic before we finish?

  19. Do you have any questions for me about the project?


This list of questions is just an introductory exercise for building a design thinking process. The whole design thinking toolbox is rich in UX methods. These techniques can help you learn more about the user at each stage of the project, and especially during the discovery phase. Understandably, your research must not be limited to an upstream investigation to lead to downstream deliverables. Your research is a permanent process to understand the users of your client's website. This process is enriched by all the data available or extracted throughout the life of the project. In a way, there is no end to user research. From this point of view, user research is anything but a closed "science," frozen in on itself.

Shapeshift is a remote and collaborative creative studio specialized in no-code digital solutions. If you have any questions or need additional guidance regarding the different UX activities & research methods to consider for a successful project, we’ll be more than happy to assist you.

Just drop us a line !

Vitika Green

Creative Director & User Experience Designer

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