Project Failure Files: No Executive Rapport

In Episode 90 of the Project Failure Files weekly webcast, Sharon and I discuss “Stumbling in the Boardroom” and how this is the failure mode where you’re overprepared on content but underprepared for the audience. You walk in with a 25-slide project novella, and the executives basically want the trailer: impact, risk, ROI, and the decision you need them to make. The core mistake isn’t “not enough data” — it’s bringing the wrong detail, in the wrong format, at the wrong level.

The discussion breaks down what executives actually listen for: what changes for the business, what could go wrong, what it costs, what it returns, and what tradeoffs you’re asking them to approve. When you can’t answer those questions quickly (or you make them excavate the point themselves), credibility drops fast — and the penalty isn’t just an awkward meeting. You get fewer chances to be in that room, fewer chances to influence direction, and fewer “benefit of the doubt” moments when you need resources or time.

The solution is disciplined executive communication: lead with the headline, the ask, and the implications — then let questions pull you deeper. As we recommend, you should use a clear structure (the “four-blocker” mindset), keep presentation slides clean, and stash the detail as reference material and speaker notes. Practice under pressure, stay calm, be clinical, and translate complexity into actions leaders can approve — because clarity in the boardroom isn’t just good storytelling… it’s leverage.

Enjoy the episode!

 

Be sure to tune in next Monday, May 18th at 9am Pacific for the next PFF episode as we discuss how juggling multiple stakeholder requests for updates and metrics can eat up hours each week—time better spent actually managing projects. Hope you can join us on our NEW YouTube channel (please subscribe!) or find us on LinkedIn.

Christian Buckley

Christian is a Microsoft Regional Director and M365 MVP (focused on SharePoint, Teams, and Copilot), and an award-winning product marketer and technology evangelist, based in Dallas, Texas. He is a startup advisor and investor, and an independent consultant providing fractional marketing and channel development services for Microsoft partners. He hosts the #CollabTalk Podcast, #ProjectFailureFiles series, Guardians of M365 Governance (#GoM365gov) series, and the Microsoft 365 Ask-Me-Anything (#M365AMA) series.