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Vol. 42 No. 4 — Jul/Aug 2025

NOTES ON DIGITAL TRANSFORMATION

Leaders may rush to start projects, but skipping these crucial questions can create future problems. A well-conducted discovery session improves clarity, serves as a risk management tool, and provides answers to common questions about the project’s complexity. But facilitating a discovery session is not easy, because it requires a mix of enthusiasm and brutal honesty. All concerns and challenges need to be considered, but this must be done in a way that’s constructive.

When I was working at a digital agency, discovery was undoubtedly the best value-add work we’d ever done for our clients. Even though the discovery outputs often reflected what our clients already knew, seeing these findings written down in black and white brought a sense of clarity to ideas that previously felt disjointed or embryonic. They translated what existed in people’s heads into a coherent, logical, and worthwhile plan. Time and time again, the discovery phase proved to be the most impactful step in a project timeline.

KEY STEPS OF A DISCOVERY PHASE

Stakeholder Interviews

Conducting individual meetings with all stakeholders—including project sponsors, subject matter experts, and developers—allows each person to share their perspective without feeling intimidated by other people’s views or priorities. A follow-up workshop with all stakeholders in the same room flows much more easily when everyone’s point of view has been carefully considered beforehand.

Options and Alternatives

What other options does the business have to achieve the project goals? Has anything already been done in this area—for example, are there market research stats or prototypes that could be used? If a similar project has been done before, what were the lessons learned? Is it possible to release a minimum viable product and then add more complex features later? What would happen if the business did nothing—is there a risk or a lost opportunity associated with this lack of action? The next step is considering different options and alternatives, which uncovers new insights. It also protects from any future questions about the rationale behind the chosen implementation approach.

Resource Allocation

Next, having the right people for the job is really important. What skills are necessary, and are they available within the organization? Will team members assigned to the project have other priorities? If so, how much juggling will be required of them? What is the optimal number of developers working on this project at the same time, and how will they collaborate with each other effectively? If hiring additional resources is needed, this may require approvals, additional budget, and time to recruit new team members. Knowing the project’s resource profile early gives the business more time to address gaps.

Story Mapping

The next step, story mapping, is a visualization technique that is structured around key customer journeys. The team considers different paths and the steps within them that customers complete when interacting with a digital product. Story mapping stimulates customer-centric conversations and reminds the team members of the different ways in which customers use the product. If designs are available, they can be added to this discussion, but if not, then sticky notes with descriptions of customer pathways will suffice. The result of the story mapping session is a more detailed breakdown of work, which can then be more easily prioritized and sequenced. It is the first step toward the creation of discrete tasks for each team member to complete.

Estimation

A high-level estimate is important for securing budget and resources. It’s not always easy to determine all of the necessary information early in the project, because a lot of details remain unknown. However, even with limited information, a rough estimate can be provided by comparing the new project to similar projects done in the past. More thorough estimates can be provided later, when more information becomes available. Projects that are particularly complex or have high levels of uncertainty require a higher contingency percentage.

CONCLUSION