Making Discovery Sessions More Effective With Prep Time

As someone who’s led my fair share of discovery sessions, I’ve come to realize that the best conversations don’t happen on the spot. They happen when people have the time to think, reflect, and gather their thoughts.

Discovery sessions, especially when you’re working with Subject Matter Experts (SMEs) and key stakeholders, are critical for understanding the needs, challenges, and goals of a project. But let’s be honest, if you throw people into these sessions without giving them any heads-up, you’re likely going to get a lot of “I’m not sure” or “I need to think about it” responses. And that’s not the kind of insight that moves projects forward.

That’s why I make it a point to always share the agenda and interview questions in advance with the people involved. It’s a simple step, but it makes a huge difference.

Think about it: when you don’t have time to prepare for a meeting, you’re often caught off guard. You might not know exactly what’s expected of you, and it can be hard to articulate your thoughts clearly in the moment. But when people have the chance to review the agenda and the questions beforehand, they come into the session feeling more prepared and more confident. They’ve had time to think about things like:

• The challenges they face in the current system

• The processes that are working well, and the ones that aren’t

• Their vision for how things should work in the future

These aren’t small details. These are the insights that shape the course of a project. And when people have the time to reflect on these points, they can bring much deeper, more thoughtful responses to the table.

I’ve seen firsthand how this approach leads to more meaningful discovery sessions. Instead of having a basic Q&A where you’re just checking off boxes, you start to have a strategic discussion. People come to the session with real examples, personal stories, and concrete ideas that allow the conversation to move beyond surface level issues.

The best part?

You get to dig into those insights in a way that truly informs the decisions you’re making for the project. Instead of just reacting to questions in real-time, everyone gets to contribute to shaping the future of the system or product you’re building.

So what does all of this look like in practice?

Before each session, I send out a document with the agenda and a list of questions I plan to ask. I include a note that encourages participants to take some time to think through their answers and jot down any thoughts they might have. This way, when we meet, the conversation is more focused, the discussion is more strategic, and everyone is ready to dive in.

This doesn’t mean you won’t still have those moments where something unexpected comes up or someone needs more time to think. But by preparing people ahead of time, you create an environment where they can engage more deeply and provide richer input.

In the end, it’s all about fostering a collaborative atmosphere where everyone feels heard, valued, and prepared to contribute their insights. The small step of giving stakeholders time to think has a big impact, and it’s a simple change that can elevate the quality of any discovery session.

How do you prepare stakeholders for your discovery sessions? I’d love to hear your thoughts!

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