Deciding between email and a face-to-face conversation for a tough message isn't about what's easiest for you. The choice should be a strategic one based on the desired relational outcome. Use email for transactional updates; use direct conversation to preserve relationships.

Tailor your message by understanding what motivates your audience. Technical teams are driven to solve problems, while sales and marketing teams are excited by new opportunities. The core idea can be identical, but the framing determines its reception and gets you more engagement.

Bupa's Head of Product Teresa Wang requires her team to explain their work and its value to non-technical people within three minutes. This forces clarity, brevity, and a focus on the 'why' and 'so what' rather than the technical 'how,' ensuring stakeholders immediately grasp the concept and its importance.

When people don't understand your point, it's often a sign that you are not meeting them where they are. Instead of pushing forward impatiently, you must go back to their starting point, re-establish shared assumptions, or reframe the message from their perspective.

When a big-picture leader communicates with a detail-oriented team, friction is inevitable. Recognizing this as a clash of communication styles—not a personal failing or lack of competence—is the first step. Adaptation, rather than frustration, becomes the solution.

Structure your final presentation by calling out specific problems you learned from individual contributors by name. Then, immediately pivot to show how solving their problem directly contributes to the high-level business objective owned by the executive decision-maker. This makes every stakeholder feel heard and demonstrates their strategic value.

True organizational buy-in isn't just a C-level activity. It's a "layer cake" where leaders at each level—from the CMO to ICs—have tailored conversations with their cross-functional partners to ensure shared understanding and commitment to the plan.

When meeting with senior leaders, shift the focus from your status updates to their priorities. Ask what's top of mind for them, what challenges they face, and how you can help. This reframes you from a direct report into a strategic ally, building trust and social capital.

When progress on a complex initiative stalls with middle management, don't hesitate to escalate to senior leadership. A brief, well-prepared C-level discussion can cut through uncertainty, validate importance, and accelerate alignment across teams or with external partners.