When I hear the phrase “how not to use email”, what immediately comes to mind is this: too many people are relying on what feels like a security blanket in email usage. They're avoiding direct engagement and, in the process, they’re missing out on an abundance of possibility that only comes from real conversation.
There’s a misconception that email is efficient. And in some logistical ways, sure—it can be. But what I’m seeing is people using email not to be productive, but to avoid discomfort. It’s easier. It's safer. It’s cleaner. But when the stakes are high—and negotiation is always a high-stakes game—easy and safe is not the path to results.
The Hidden Cost of Avoiding the Conversation
If your gut tells you, “This is a tense situation, and I really don’t want to talk to this person,” and you’re about to send an email to sidestep the interaction, let that be a red flag. When I do that, I’m being a lazy negotiator. Period.
Our best asset—whether you're in real estate, tech, or international trade—is the conversation. Your ability to listen, to calibrate, to read tone, to build trust in real-time. And you don’t get that from an email.
Emails don’t deliver tone. They don't deliver the subtlety of a pause, the pitch in a voice, the hesitance or openness behind a word. And they definitely don't deliver rapport.
That’s a huge loss.
Worse, if you’re emotional—frustrated, angry, or feeling misjudged—and you still hit send, that's when email becomes a weapon, not a tool. It's a digital vent session dressed up as communication. When you're charged up and feeling wronged, the worst thing you can do is let your keyboard speak for you. You might be right. You might have all the logic on your side. Your email is almost always going to be misinterpreted as sharp, clipped, or defensive. Congratulations, you've just made yourself the problem.
Instead, do the hard thing. Pause. Pick up the phone. Or at the very least, save that draft and revisit it later with a clear head. Better yet, ask yourself: Would it be ridiculous for us to just talk this through?
I’ve never once regretted waiting to send an email—but I’ve absolutely regretted sending one too fast.
Use Email as a Bridge
We’re not saying email is evil. It’s a necessary tool, especially to summarize conversations or to document agreements. But email should never replace the negotiation—it should support it. Use it to set the table for a deeper conversation.
One simple example: rather than opening with “Hope you’re well” and jumping straight into demands, try opening with an Accusation Audit™. Start with: “This is probably the last email you want to read today...”—then deliver the core message. And always close on a positive note. The last impression is the lasting impression.
And keep it short. Nobody’s reading your five-paragraph explanation of why you’re right. They’re scanning for tone. If it reads like an attack, it is an attack—no matter how right you think you are.
Missed Opportunities Are the Real Loss
One of the biggest hidden costs of overusing email is missed opportunity. The lost chance to Label, to Mirror, to dig for Black Swans. The intel you could have received from a slight hesitation in their voice, or a shift in energy, or something they didn’t say.
In real estate, I’ve seen this repeatedly. Two agents both make similar offers. One sends it over with no interaction beyond confirming receipt. The other picks up the phone, uses an Accusations Audit, builds rapport, creates a connection—and that connection becomes the differentiator. Who would you rather work with in a complex deal? The agent who treats you like a person, or the one who treats you like a transaction?
People want to work with people they like. And you can't be likable in a three-line email.
Practical Steps to Start Shifting
If you’re someone who lives in your inbox, the first step is awareness. Ask yourself: Where in my day could I improve outcomes just by having a conversation instead? Identify those moments. Don’t start with the million-dollar deal. Start small.
Practice tactical empathy at the grocery store. Use mirrors with your barista. Try a label on your neighbor. Get the reps in. Learn to speak the language of high-level negotiation in low-stakes environments. That’s how you build confidence and start using the Black Swan skills naturally.
Because if you wait to try this stuff only when everything’s on the line… you’re gonna choke. It’ll feel forced. But if it’s part of your rhythm, then when the real game starts, you’re already fluent.
Final Thought
If you're using email because it feels safe, stop and ask: Am I working against myself?
Every message you send is either opening doors or closing them. Choose the medium that brings connection, not just convenience.