The Conversation You Shouldn’t Skip Before Every Big Project

Almost every team problem we can name traces back to a conversation that happened badly or never happened at all. And nowhere is this more true than at the very start, before a project begins, before someone steps into a bigger role, before a big ask lands on their plate.

This is the “enrollment conversation.” And most of us have never had one.

The enrollment conversation is about inviting someone into a cause. It opens differently than a typical handoff: “Here’s the problem we’re trying to solve for our customers. Here’s why it matters right now. And here’s why I believe you specifically are the right person for this.”

Then comes the part a lot of us skip: “What part of this actually energizes you? And what would help you do your best work here?”

That last question means the difference between managing someone toward an outcome and building something together.

Simon’s research into purpose-driven leadership consistently shows that when we lead with why, people stop asking “what do I have to do?” and start asking “what can I contribute?” Self-determination theory, developed by psychologists Edward Deci and Richard Ryan and now one of the most robust frameworks in organizational psychology, tells us that humans have three core needs at work: autonomy, competence, and the belief that their work means something beyond a paycheck. A proper enrollment conversation activates all three at once.

Gallup’s engagement research has found, year after year, that only about a third of employees feel genuinely engaged at work. The rest show up. They do the job. But they’re not bringing the part of themselves that would actually make a difference. And often, that gap opens in the very first conversation, the one where we handed them a task instead of extending an invitation.

Here’s what this looks like in practice: Before your next project kickoff, before you forward the brief and set the deadline, try something different. Sit down first. Explain the problem you’re actually trying to solve. Name why it matters to real people. And then say what you genuinely believe: “I think you’re the right person for this because…” and actually finish the sentence with something specific.

Then ask the question most leaders skip. Ask what energizes them about it. Ask what they’d need to do their best work. Then be quiet and actually listen.

You might be surprised by what you hear. And you’ll almost certainly get better work out of it.

That’s where the leadership lifestyle actually lives.