Evaluating Opportunities and Leading Product Design with Jessica Hall | Episode #81

Jessica Hall did not expect to have a creative career. She first wanted to become a reporter at The Washington Post, but a summer at a news museum changed that plan. Graphic design showed her that creative work did not require drawing realistic objects. Her work expanded into exhibit and set design, animation, video, interactive exhibitions, websites, and mobile products before she joined CoStar Group in 2020.

At CoStar, Hall leads design for products that help commercial real estate professionals make decisions with data. The same information serves brokers, owners, lenders, appraisers, hotel operators, and other users across many countries. The product has also developed over more than 30 years and through acquisitions. That combination creates a demanding design problem: modernize connected experiences for distinct jobs without losing the detail each user needs.

What you'll learn

• How to combine interviews, metrics, sales feedback, and client testing when evaluating product opportunities

• Why specialized B2B prototypes need internal domain checks before customer research

• How a leader's intent gives teams room to adapt without losing the desired outcome

• Why design executives need to understand business goals and align multiple product groups

• How to use generative AI for ideas and writing while protecting information and checking every result

Evaluate the opportunity before testing the interface

Hall begins experimentation by asking what the team needs to learn. Before creating a prototype, the first question is often which opportunity deserves investment. She listens to customer feedback, speaks with sales colleagues, reviews available measures, and interviews people to understand both the problem and the possible upside of solving it. This prevents the existence of a design idea from becoming the reason to pursue it.

Once the team has a wireframe or mockup, it tests internally with researchers and salespeople. That step matters because commercial real estate examples are unusually specific. A prototype can look coherent while combining a deal type, square footage, rent structure, owner, or other detail in a way that makes no sense to an expert. Internal review helps the team make the scenario credible before asking clients to react to it.

Client testing follows. After release, the team introduces the new capability, explains how to use it, collects feedback, and looks for behavior it did not expect. When a feature produces an unanticipated result, the response is to talk with users and investigate rather than force the evidence into the original prediction. For product teams, the useful pattern is sequential: select the opportunity with evidence, validate the scenario with domain experts, test with customers, then continue learning in production.

Create alignment by communicating intent

Hall describes a vice president of design as a business leader whose impact must extend beyond design output. Her work includes connecting functionality across sister brands, coordinating product managers with different priorities, and helping business units converge on a consistent experience. Understanding the business is part of serving the customer because it clarifies the relationships and constraints behind daily decisions.

She also separates assigning work from explaining intent. A leader can prescribe every step, but that limits what product managers, designers, and engineers can contribute when the plan meets reality. Hall instead emphasizes the mission, why it matters, what success should look like, and the current plan. If the plan fails in practice, the team can still make decisions that support the intended result.

This approach gives listeners a practical test for leadership communication. Before handing work to a team, ask whether people know only what to do or also understand the outcome they are responsible for producing. Clear intent creates room for judgment while preserving alignment. Hall also notes that collaboration has a limit: some decisions ultimately belong to the leader, who must use the authority of the role so the organization can move forward.

Use AI for assistance, not authority

Hall views AI as broader and older than the recent attention around chatbots. In commercial real estate, narrow applications can analyze property photos, assess aspects of a building's condition, and relate a property to other properties. Newer tools widen access to experimentation and can support clients who need to track deals, communicate, maintain relationships, and find opportunities.

In her own work, Hall uses generative AI to develop ideas, draft performance reviews, write interface copy, and name things. She applies two firm controls. Proprietary company information does not go into public chatbot tools, and the person using the output remains responsible for checking it. Fluent, confident language is not proof that a result is accurate.

The same standard applies whether AI is proposing copy or supporting a product concept: define the question, protect sensitive information, and verify the answer. AI can speed exploration, but it does not remove accountability from the designer or leader using it.

Listen to the episode

Hear Jessica Hall's full discussion of opportunity evaluation, specialized product testing, organizational alignment, leadership intent, and responsible AI use. Listen to Episode #81.