Counterintuitively, highly formatted and image-heavy emails can feel corporate and impersonal, decreasing engagement. Shifting to a simpler, plain-text style mimics a personal message from a friend, which increases perceived authenticity and encourages more replies and genuine connection.

The Nonviolent Communication framework (Observations, Feelings, Needs, Request) provides a script for difficult conversations. It structures your communication to focus on objective facts and your personal emotional experience, rather than blaming the other person. This approach minimizes defensiveness and fosters empathy.

When a prospect's voicemail directs you to text, structure your message for reading, not listening. Start with relevance about them, not your name, because they will likely read a transcript. This optimizes the message for the medium they've chosen.

People engage in three types of conversations: practical (problem-solving), emotional (empathy), or social (identity). When participants are in different modes—like one offering solutions when the other wants validation—the connection fails. Recognizing and aligning these modes is key to effective communication.

The communication event doesn't end once you've delivered a message. You must also have the emotional and mental capacity to handle the subsequent dialogue, questions, and responses. If you lack the energy for the entire process, consider postponing.

Genuine rapport isn't built on small talk; it's built by recognizing and addressing the other person's immediate emotional state. To connect, you must first help them with what's on their mind before introducing your own agenda.

Taking the easy way out (e.g., sending a tough email) focuses on avoiding external messiness. Communicating with inner ease means you are emotionally prepared to handle any reaction because you've acted with consideration. The goal is inner calm, not avoiding external conflict.

Instead of trying to find the perfect words, preface difficult feedback by stating your own nervousness. Saying, "I'm nervous to share this because I value our relationship," humanizes the interaction, disarms defensiveness, and makes the other person more receptive to the message.

The key to a successful confrontation is to stop thinking about yourself—whether you need to be seen as tough or be liked. The singular goal is to communicate the unvarnished truth in a way the other person can hear and act upon, without their defensiveness being triggered by your own emotional agenda.