Leading Successful Discovery Sessions: Set the Stage for Client Projects

discovery session

Have you ever drastically miscalculated a project deadline? Given an estimate to a client that wasn’t reflective of the actual work required? Forgotten to include key stakeholders from the beginning of a project?

If you have, you’re well aware of the frustration that unfolds when expectations aren’t met. Conflicts during a project stem from unforeseen circumstances but are often the result of poor communication at the start of a project.

Enter the discovery session.

What is a discovery session?

Discovery sessions are like the in-real-life version of a project brief. Generally, they consist of a series of meetings that uncover the needs of your client and allow team members to define the value and importance of a new project.

The value of a new project may be difficult to initially conceptualize if the success criteria for each stakeholder is different. For example, if you’re building a new private app, the success of this new app will vary by each team. A technical manager may be concerned with security and uptime, whereas the finance director may be concerned with the project cost.

Identifying the goals that need to be considered—and their order of priority—for your client’s project to be considered a success is the primary objective of a discovery session.

Learning to navigate the discovery process takes time, experience, and continuing refinement. In this article, we will explore the necessary steps (and complementary resources) to help you kick off your next project.

You might also like: A Web Designer’s Guide to Project Schedules.

How to structure your sessions

The final outcome of your discovery sessions should be to establish goals across departments, enabling you to create a high-level map of necessary steps for project success within the company as a whole. Marketing your project and creating sales leads may be equally important as implementing a quality project if one of your success criteria is defined by a certain amount of users, downloads, sign ups, etc. Likewise, if monetary value is a success criteria (it likely is), and a finance director is not consulted, your project expenses could be unrealistic and financially strain the company.

Establishing goals across departments will enable you to create a high-level map of necessary steps for project success within the company as a whole.

That can be a tall order, and so preparing for your discovery sessions deserves thoughtful consideration. What comes out of a discovery session is ultimately determined by what you put into it—structure, brainstorming exercises, potential constraints, and the right questions.

"What comes out of a discovery session is ultimately determined by what you put into it."

It should be made clear to your client how crucial these sessions are to the outcome of the project. As the facilitator for the discovery sessions, you’ll want to ensure that everyone gets a chance to speak as you navigate the process towards goals and success criteria. Essentially, your job is to help identify what department goals need to happen to help fulfill the larger organizational goals.

Below are the steps you should complete to ensure your discovery sessions are set up in the best way to come to these goals.

1. Before the first session, set the stage

At the start of a new project, discovery sessions are meant to build a solid foundation between you and your client for a successful marriage of goals and expectations. They involve research, interactive activities with your clients, and are focused on uncovering your clients’ needs, defining the goals and business drivers behind the initiative, and refining the scope of the project.

Before jumping into a discovery session with a client, ask yourself questions like:

  • What are the tangible outcomes we want to get out of the discovery sessions? How will we document and share these outcomes?
  • How many people will be involved (including project team members and client stakeholders)? How engaged and informed are the stakeholders?
  • How long will this project take to complete? How complex is the work? How well defined are the project scope and requirements?
  • Are there risks or unknowns that need further exploration?
  • How much effort is required for research, client sessions, and internal planning?

With these questions in mind, have a thorough discussion of the key aspects of the project with the client. These questions will help you identify and plan the discovery sessions in a way that suits the project and client. Only once you’ve discussed these should you take the first steps towards mapping out a discovery session.

General rule of thumb: The effort and time required to conduct a discovery session should be proportional to the length and complexity of the project.

You might also like: 5 Questions You Should Ask Your Clients Before Every Web Design Project.

2. Create a logical flow for every session

Make sure there is a logical flow to your sessions. It’s best to use structure that starts very broad (organizational goals and vision) and gradually gets more narrow (e.g., the features of the store).

Generally speaking, you should structure your sessions in the following order:

  • Organizational goals: the vision for the client organization
  • Departmental goals: the role played by each organizational branch or division
  • Individual goals: the personal drivers of each stakeholder

Laying out everyone’s goals in this way ensures that stakeholders are on the same page, and the scope of the project has been refined.

3. Include the right stakeholders

For the project to be successful, make sure the right people are included from the beginning. Before the initial discovery session, discuss with the project leads which key stakeholders are needed for successful roadmapping. Ideally, you want representation for each group of stakeholders.

"For the project to be successful, make sure the right people are included from the beginning."

To help your client identify stakeholders on their end, you can provide them with questions to help identify the right people.

For example, you will want to know:

  • Who is directly involved with the project?
  • Who is indirectly involved with the project?
  • Who may be affected by the project?
  • Who may be affected by the project’s outcome?
  • Who gains or loses from the project’s success?
  • Who wants to complete the project successfully and who doesn’t?
  • Who are the suppliers?
  • Who is the user of the end result of the project?
  • Who are the competitors?
  • Who are the shareholders?
  • Is any local community impacted by the project or its outcome?
  • Who has the authority to influence the project or its outcome?
  • Who has the authority to make the project succeed?
  • Who can make your project fail?

Next, create a short list of representatives that will speak for each stakeholder group that needs to be considered. Then decide if it makes sense to break the group up into separate sessions.

For example, a CEO is well-suited to discussing the overarching organizational goals and vision—but may not be able to discuss the technical specs. Yet, an IT lead is well-suited to discuss the technical specs—but may not be able to speak about the business objectives.

It doesn’t always make sense to include every stakeholder in each discovery session. It’s also important to keep the group small when possible. Having an intimate group allows for more vulnerability, transparency, and honesty about the project.

4. Account for mental breaks

Next, account for the cognitive effort required for your session attendees to be active participants. It’s best to structure the discovery sessions to account for mental breaks. This will maximize the engagement of team members and make your job easier.

Be very clear about the purpose, format, and desired outcomes of each session to help participants focus their contribution. As effective discovery sessions require active participation from clients, consider things like:

  • Two half-day sessions instead of a full day
  • Extended lunch and frequent breaks
  • Fuel for the mind: coffee, snacks, etc.

You might also like: How to Develop an Effective Creative Brainstorming Process.

Bring your best self forward

First impressions matter and your approach to discovery can help pave the way for a strong and collaborative relationship with your client. Here are some tips to keep in mind when approaching a new client project.

Be prepared

Being prepared instills confidence with your client. A few suggestions to get you started off on the right foot:

  • Make sure the agenda is drafted and reviewed in advance. Give the client a chance to tweak it if needed.
  • Explicitly ask the clients what they want to get out of the discovery sessions when planning so you can account for their needs.
  • Do your research: who is going to be in the room and what can you find out about them?
  • Build in a contingency plan. Allow for buffer time, breaks, and flexibility to ensure you can stay on track and reach the desired outcomes.

Be personable

When it comes to successful projects, human connection is equally as important as robust technology. With a concerted effort to connect with key stakeholders, you can ensure the best results.

  • When possible, hold the discovery session(s) in person.
  • Make time to get to know stakeholders on a personal level, whether it’s during breaks or over dinner.
  • Remember that people can make or break projects, so make every effort to build a personal connection.
  • Be inclusive. Make sure everyone involved in the sessions gets a voice and feels heard,

Be honest

Honesty feeds into trust—without it, your team members will likely lack confidence in your direction for the project.

  • Build the foundation for a strong working relationship by being upfront and transparent with your clients.
  • Flag risks and unknowns as they are uncovered during discovery.
  • When you’re asked questions, tell the truth if you don’t know the answer. Ensure to follow up with an informed answer as soon as you can.
  • Remember that being honest is a key part of setting and managing expectations.

Be adaptive

Most importantly, learn to be flexible. Every new client project will have different working dynamics, project considerations, and success criteria. Having a one size fits all approach simply won’t cut it.

  • If the technical aspects of the project are complex, you may want to dedicate time/budget for a technical deep-dive. This will mitigate risk.
  • If there is tension between different departments, you may want to run separate sessions. This will allow you to better understand their needs before bringing them together.
  • Keep in mind that there is no single "right way" to run a successful discovery session. Approach your clients with a flexible, personalized approach.

You might also like: 4 Quick Ways to Build Trust With a New Client.

Create a collaborative space

It’s important to note the likelihood of groupthink, that pesky psychological phenomenon that results in dysfunctional decision-making. When we collaborate, we want to do so harmoniously and without headaches.

This makes us human but can be dangerous in the ideation stage. Be sure to inform key contributors and have them do research and independently explore ideas for the project in advance. For example, if you’re redesigning a brand, have each contributor make a moodboard of ideas that they believe speaks to the look and feel of the company.

discovery session: groupthink
An example of groupthink from 42hire.

To mitigate any notion of groupthink during the discovery session, several tactics can be used to encourage participation and surface different perspectives. When leading a discovery session, your role as a moderator is to ensure each participant has room to speak, share ideas, or disagree.

"Your role as a moderator is to ensure each participant has room to speak, share ideas, or disagree."

Agile moderators will often leverage post-it notes during collaborative sessions to ensure each stakeholder can be heard. For example, all participants can write down what they think is the main project objective on a post-it note then have it shared with the group to find common themes. This tactic creates a safe space for all attendees—regardless of personal reservations, or organizational rank.

Finally, implement democratic voting systems where you can. Have several proposed solutions? Divvy up an equal amount of stickers; these will be used as a currency for voting. List your solutions on a whiteboard and have each person place a sticker on their personal preference for a plan of action.

Make it interactive

Explore ideas for how you can get the most out of your interaction with team members. Collaborative group exercises are a good way to break the ice and get those creative juices flowing.

A few exercises to replace traditional brainstorming activities:

Mind maps

Especially good for design-related brainstorm sessions, mind maps are diagrams used to visually organize information. A central concept or theme is drawn in the center, and ideas or words building off that theme branch off from the core. For visual learners, this is a great way to go, although it’s harder to consolidate in a group setting than sticky notes.


A quick exercise to get team members contributing is to create a storyboard. You can use paper, whiteboards, or sticky notes. Sticky notes—if given to all members—have the added value of getting a well-rounded group response. Each storyboard will vary depending on the type of project but as a rule of thumb, you can start by mapping the current process.

Six Thinking Hats

Often we default to the type of feedback style we are most comfortable with giving. For some, that may be sticking to facts, for others, it may be sharing gut reactions. The Six Thinking Hats is intended to break team members out of these tendencies. Assign different “hats” (a role to be precise) to stakeholders when discussing new topics or if you notice that there aren’t well-rounded considerations for each project idea.

discovery session: six thinking hats
Six Thinking Hats visual from Rapid Transformation

Tools and resources

We’ve compiled a list of resources that can help you facilitate your discovery sessions.

    Template Icon

    Know your limits: Discuss constraints

    Project goals are equally as important as project constraints. All necessary factors should be explicitly discussed: time, budget, scope, etc.

    Ask your client which of these criteria is least flexible, and why.

    For example, the store’s launch date is not flexible, because the website has to go live before a pop-up store event, but there is some flexibility in the budget and scope to ensure the launch date can be met.

    Next, discuss which of the constraints is most flexible, and why.

    For example, the scope of the project and list of proposed features is the most flexible because the client would prefer that the store launch within the deadline and budget.

    Moreover, it’s critical to understand that some constraints must be more flexible than others. Operating under multiple fixed constraints is setting the project up to fail.

    Document your findings

    As the facilitator, you can record the findings from the discovery sessions or you can assign a willing team member record-keeping duty. Focus on goals, key performance indicators (KPI), risks, and unknowns. Keep the documents well organized throughout the process. This will be an iterative process—inform team members that the project notes may change by the end of the session.

    After the discovery sessions are complete, take time to go through the recorded documents. You can arrange this into a proper project brief afterward. Confirm each goal and success criteria moving forward.

    After you have formalized the project brief, send out all the documents to the key stakeholders. This will ensure full transparency and a unified point of reference across the team.

    Putting it all together

    Successful discovery sessions are the necessary first step to any new client project. Effective discovery is more than just the summation of project goals; it helps drive decisions, refine scope, and align stakeholders at every subsequent project phase. Defining the value of a project as it relates to the company will allow you to navigate the process with realistic goals for success.

    "Effective discovery is more than just the summation of project goals; it helps drive decisions, refine scope, and align stakeholders at every subsequent project phase."

    Lastly, discovery sessions lay the foundation for a healthy working relationship with your clients and that close collaboration can help assure expectations are aligned and project goals are met. This approach maximizes the value of your work and encourages repeat business—and who doesn’t want more of that?

    Have you lead a discovery session before? What was your biggest insight? Share your experience in the comments below!

    Grow your business with the Shopify Partner Program

    Learn more