7 Topics that Should be Covered During a Digital Discovery Workshop (including 70+ Specific Questions You Should Ask)

Discovery Workshops play an important role in the success of any development project. If a Discovery Workshop is not conducted the right manner, its value can be lost.

At the beginning of a project, Discovery Workshops are the part of the “Discovery Phase,” which can be considered as the courtship period, during which a strategic partner usually collaborates with his client to understand the project’s requirements and functional specifications, and to discuss content modelling, solution architecture and so on. The aim is to define the project’s business goals by fitting the pieces together.

This is the foundation of any project.

However, a successful Discovery Workshop is only achieved when the right set of questions are asked. Here is my list of questions that I consider are important to ask while you are onsite with client, discussing the details of his or her project.

For me, the right set of questions inspires the client to think about what he or she needs out of the whole engagement. It also ensures that there are no surprises and unwritten assumptions.

I’ve grouped my questions (more than 70 of them!) into seven topics.



  • What is the end goal of this engagement?
  • What is the client proposition around it?
  • How, as partners, shall we together actively evaluate the success of the project?
  • How will we ensure that the business goals are met at the end of engagement?
  • How does this whole engagement fit into the client’s vision and overall strategy?
  • How does this project stack up against competition?
  • What will this solution create a “unique selling proposition” for the client?


User Experience


  • Who is the target audience?
  • What is the demographic of audience the client is targeting?
  • What are the different needs of the users who will be coming to the project for a solution?
  • Is there any specific timing during which users will use the application?
  • Why will they want to come back, or refer it to others?
  • As a service provider, what does the client want the user of the solution to do?
  • What are the current challenges?
  • What is the expected “user journey?”
  • How can customer satisfaction be improved?
  • How can desired conversions be achieved?
  • How is the competition doing it differently?
  • What devices will the application be supporting?
  • What are the usability cases that the client is expecting?
  • What platform are we building the application for?
  • Is accessibility compliance a goal?




  • What is our primary content type?
  • Are we planning to migrate old content?
  • If so, what content should be moved, specifically?
  • How will the content, old and new, relate to each other?
  • What will be our user permissions and workflows?
  • Is content strategy part of the scope?
  • How frequently will different pages be updated?
  • Will there be personalization/localization of content? If yes, what are the APIs that the client has thought of?
  • Will the product be designed for different, specific markets? If yes, what differences will be expected?
  • Will the solution be multilingual? If so, what is the default language, and how will language-selector needs be changed with regard to the user journey?
  • Are there any specific requirements with regard to different markets?


Visual/User Experience/User Interface


  • What are the style guidelines?
  • How well are brand guidelines defined?
  • Do brand assets -- logos etc. -- exist?
  • How rigid is the existing style guide? As the solution partner, do we have some flexibility?
  • Are there any designs that are already in the client’s mind?
  • Any existing creative insights in the minds of stakeholders?
  • Are there emotional end states that the client wants to engender in customers?
  • Functionality


What functionality is expected?


  • Are there any expected integrations with social networks?
  • Are there any third-party integrations that the client is expecting?
  • Is the client expecting any of the solutions to be multilingual?
  • Most importantly, how are these functionalities supposed to help the client achieve the project’s business goals?
  • Is data capture required?
  • Are there any requirements for e-commerce, store locators, or any Google API integrations?




  • What level of security checks/compliances is the client expecting?
  • Is encryption required?
  • Does the client have a legacy system that needs to be integrated?
  • If change in an existing system is required, where are current databases located? Does the client want to change them? Do they have any preferences around this process?
  • Where will the solution be hosted?
  • What backup mechanism is expected?
  • Is client expecting CDNs, AWS, or Akamai to handle spikes in traffic?
  • Is there any development framework the client wants us to follow?
  • Does client expect a tracking mechanism? If yes, which tool: for example, Webtrends, Adobe Site Catalyst, or Google Analytics?


Project Management & Governance


  • What is the client’s expectation with regard to a Project Plan?
  • Who are the stakeholders? Who shall be the client Point of Contact for all communication during the project execution?
  • How comfortable is the client with agile methodology?
  • What is the preferred communication mode? What tools will be used to collaborate?
  • Who needs to be involved in day-to-day communication?
  • Who will manage the Project Management process?
  • What does the project’s RACI (Responsible, Accountable, Consulted, and Informed) look like?
  • What will be the change-management process?
  • What is the tentative live date? How are we arriving this live date via business goals? What would be the impact, if the “live” date is not met?
  • What are the potential risks associated with the “live” date?


When these questions are answered, a Discovery Report should be shared with the delivery team. This will not only help with the smooth execution of project, but it will also reduce surprises down the road.

Although these workshops are usually an added expense in the project’s budget, they are well worth it. As a strategic partner/consultant to the client, it makes sense to encourage these workshops -- to ensure better understanding and a smoother collaboration ahead.