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.

Don't hang up immediately after booking a meeting. Invites from new contacts often require manual acceptance to appear on a calendar. To prevent no-shows caused by a missed invite, stay on the line and ask the prospect to confirm they've received and accepted it.

The person requesting the introduction is the 'pursuer,' not the 'prize.' Sending your Calendly link first subtly implies the target should conform to your schedule. Instead, propose specific times manually to demonstrate flexibility and respect for their time. Let them offer their own scheduling tool.

Even when dining with someone much wealthier who invited you, offering to pay is a key sign of respect. They will almost certainly decline, but the gesture reframes the interaction as one between equals rather than a hierarchical one.

Instead of open-ended agenda items like "let's do intros," propose specific time frames, such as "Let me give you 90 seconds on me, you can give me 90 seconds on you." This small framing tactic establishes you as a professional who respects time, prevents conversations from meandering, and maintains control of the meeting's flow.

Avoid vague commitments like "end of next week." Instead, insist on converting all follow-up plans into specific numeric dates and times (e.g., "Tuesday, November 4th, at 11 AM"). This micro-skill forces clarity, creates a firm commitment, and prevents follow-ups from falling through the cracks, holding both parties accountable.

If your natural communication style can be misconstrued (e.g., direct, quiet, transactional), preface interactions by explicitly stating it. For example, "I tend to go straight to action mode." This provides crucial context, manages others' perceptions, and gives you permission to be authentic.

The order of names in an email's "To" field carries a subtle social hierarchy. Placing someone first implies they are the primary intended recipient. Being listed fifth suggests you're less central to the conversation, influencing how much attention you pay.

To combat no-shows, don't end a call after booking a meeting. Ask the prospect to find and accept the calendar invitation while you are still on the line. This simple step ensures the event is actually on their calendar and bypasses issues where invites get lost in email.