The Tech Leader's Guide to Difficult Talks That Actually Work

Leadership is publicly pushing hard on AI — and your team is feeling it differently. Some are vocal about it, others aren't saying what's really on their mind. Meanwhile the classic hard conversations haven't gone away: missed deadlines, underperforming teammates, stakeholders pushing too hard. You're probably avoiding at least one conversation right now — not because you don't know it needs to happen, but because the last time you tried something like it, logic didn't land the way you expected — and the situation got harder, not easier.

This session gives you a practical framework for debugging communication the same way you'd debug code — and the skill to manage what makes these talks hard in the first place. The anxiety before, the rumination after, the pull to over-explain or go silent. You'll work through real situations in the room — yours or someone else's — and leave with more than you expected from the people around you. You'll leave with the skills to walk into difficult conversations with steadier confidence — and walk out with more clarity and less conflict.

About Hunter Milligan

Technical leaders and developers are under more pressure than ever — tighter deadlines, shifting priorities, and now an AI landscape that's moving faster than anyone can fully keep up with. When the pressure is constant, even sharp, experienced people start reacting instead of leading. That's where Hunter comes in.

As a former developer and Fortune 500 consultant turned performance coach, Hunter works with technical leaders and developers who are done running on fumes. For 15+ years he's helped analytically-minded professionals stay clear-headed under pressure, lead with steadiness instead of adrenaline, and actually get more done — without the grind that burns people out.

When not traveling the states or the rest of the world, Hunter enjoys mountain biking, snowboarding, and practicing tai chi—often in unexpected places.

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