PM Interviewing Tips to Get the Most Out of Discovery Sessions

PM Interviewing Tips

“Project failure rates hover around 70 percent,” says Think’s CEO, Tony Gruebl, in The Red Pill Executive. Written by Think executives, the book sheds light on management issues and helps companies avoid mistakes that cost money, time, and resources.

“Enough losses can threaten a company’s success and even existence,” Gruebl explains.

So how do you avoid failure and steer your project towards the 30% success range?

A successful project starts with a thorough discovery session, which sets the expectations for both the client and project managers.

These kick-off meetings are crucial to creating a space to ask questions, cover strategy, user experience, content, and go over any details that the client or project stakeholders want to define as an outcome of a project.

To ensure that everyone is on the same page, a rock-solid discovery session starts with asking the right questions. We asked some of our PMs at Think key strategies they include in these planning meetings.

Here are some of their expert tips and insights.

Define roles

To lay the road map for a project. Management consultant Ben Adrian first defines the client or stakeholder’s role in the organization.

“Separate the stakeholder from the project and examine their role in the broader organization,” he says. “Once you do this, it makes it easier to define their role in the project and continue to set and manage those expectations.” 


Management Consultant at Think

Lead with the right questions

Senior management consultant Katrina Kastendieck advises to never start with a “blank page.”

“You will get more input from people correcting your ‘incorrect’ statement than from starting at zero,” she says. 

In every discovery session, Kastendieck asks her clients, “What about this project keeps you up at night?” This helps her gather the project’s risks.

“People tend to conceptualize this better than simply asking, ‘What are the risks?’” she explains.


PMP, CSM, CSPO, SAFe® Practitioner
Senior Management Consultant at Think

Implement the ‘5 Whys Technique’

Senior management consultant Scott Sax and senior management consultant Jeffrey Berenholtz encourage facilitators to use the “5 Whys Technique” in discovery sessions.

The “5 Whys” technique was developed in the 1930s by Sakichi Toyoda, the Japanese industrialist, inventor, and founder of Toyota Industries.

The method is remarkably simple: when a problem occurs, you drill down to its root cause by asking “Why?” five times. When a countermeasure becomes apparent, you follow it through to prevent the issue from recurring.

“It’s easy to get stuck on the ‘how’ or solving the problem in discovery sessions,” says Sax. “This technique helps clients consider the ‘why’ of what they are trying to achieve or fix.”

Berenholtz explains that the technique “helps to get to the root of requirements and discovery and ensures you routinely get below the surface level input and dig-in to the core understanding of any issue.”

Scott Sax

Senior Management Consultant at Think

Jeffrey Berenholtz

Senior Management Consultant at Think

Visual Aids

Director of management consulting Erica McQuiston shows her clients what metrics she will be capturing throughout the project. During discovery sessions, she encourages PMs and facilitators to either write these out on a whiteboard or type into a document on a projected screen for clients to conceptualize visually.

“It is crucial to confirm each deliverable is understood by all of the individuals in the room so that there are no surprises or loose ends at the end of a project,” she says.

Successful discovery sessions are the necessary first step to any new client project and give the project a solid foundation for future success. These sessions increase the project’s chances for success by defining roles, setting expectations, gathering risks, driving decisions, refining scope, and aligning stakeholders. A thorough discovery session defines the value of a project in relation to a company and allows PMs and facilitators to navigate the process with realistic goals for success.