323: Communicate With Courage with Dori Gilbert

August 31, 2025·41 min·3 clips

A CEO told Laura he didn't want middle managers worrying about strategy—and that's exactly why his projects were failing.

Host Laura Bernard interviews Dori Gilbert, an expert in project management and strategic communication, about her communication agility framework. They explore how project leaders can bridge the strategy-to-execution gap through more effective communication. Gilbert combines experience in project management, product strategy, change leadership, and marketing. Laura shares a story about a CEO who complained of "middle management problems" but admitted he didn't connect his team to the organizational strategy. Gilbert references a 2025 PMO Outlook report noting 41% of project priority decisions are now made by executive say-so, up from 23% the previous year. She describes common communication failures, like project managers avoiding yellow or red status reports for fear of appearing incompetent. Gilbert recounts witnessing a 20-minute team meeting derailed by a discussion about sourcing a specific cable, which she cites as a misaligned use of time and audience. Her framework focuses on developing clarity, adaptability, and strategic presence to land relevant messages with various audiences. The conversation centers on three core filters for communication agility: courage, context, and conflict. For courage, Gilbert advocates "empathetic action," using the example of how she successfully negotiated with a purchasing agent by explaining context and showing respect for their workflow. She suggests proactively meeting with stakeholders to understand their objectives and obstacles. Regarding context, Gilbert shares a story from her first project lead role, where an executive's question in a gate meeting revealed an unaddressed product specification, teaching her the importance of context awareness. She recommends project leaders dedicate an hour weekly to widen their lens, analyzing team purpose, organizational brand promises, and market positioning. Laura simplifies strategic alignment into three questions: what are we doing, why are we doing it, and what does success look like. On conflict, Gilbert shares a personal story of her life "falling apart," which led her to improve her communication and resume writing significantly. She connects unresolved internal conflict to external project issues like poor prioritization and unclear stakeholder communication. Gilbert has created a free assessment tool to help individuals identify their conflict management styles and patterns. The episode has an educational and conversational tone, blending personal anecdotes with practical frameworks and actionable advice. Listeners interested in practical strategies for influencing executives, managing stakeholder conversations, and improving their leadership presence will find value. Those seeking highly technical project management methodologies or disinterested in soft-skill development might find the focus less relevant.

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