Crucial Skills®

A Blog by Crucial Learning

Crucial Conversations for Mastering Dialogue

How do you hold a crucial conversation via e-mail?

Emily Hoffman

Emily Hoffman is a Master Trainer and Senior Director of Client Training and Employee Development at VitalSmarts.


How do you hold a crucial conversation via e-mail?

A crucial conversation is best handled face-to-face. No exceptions. The best among us use e-mail and voice mail to schedule and follow up on crucial conversations, not to hold them. The reality is, however, that we can’t always have an in person conversation. For example, I once trained a manger based in the United Kingdom who supervised a team based in India. They met together once a year. A face-to-face crucial conversation was typically not possible.

So, three quick thoughts on applying these concepts to e-mail:

  1. Make sure you refuse the sucker’s choice. Too often, we resort to e-mail rather than the telephone. We tell ourselves it is because we can’t get in touch with the other person, they don’t respond to our calls, etc. In reality, it may be that we would simply rather hold the conversation on our timeframe (something made possible through e-mail) than on the other person’s timeframe. Check to make sure you aren’t selling out and always choose to have a conversation over the phone rather than over e-mail.
  2. Make it safe. This is probably the most crucial thing to do during an e-mail conversation. What most often gets lost in e-mail is our intent. In a face-to-face conversation, people read our intent through our body language, even more than through our spoken words. Nodding, crossed arms, raised eyebrows all communicate intent. Because safety is a function of intent, you absolutely must find a way to clearly communicate your good intentions. Don’t rely on the other person to assume your good intentions and don’t think that adding an emoticon at the end of a paragraph will solve the problem.
    Contrasting is a great way to clarify your intentions. You also want to consider ways to communicate your intentions that are unique to e-mail. For example, one of our trainers in India related the following example to me: A participant in the course recognized that he needed to apologize to a colleague who worked in a city several hundred miles away. He was concerned that if he simply e-mailed an apology the colleague wouldn’t accept it as sincere. He wanted to do something to demonstrate his sincere intention to apologize and take responsibility for his bad actions. So, he e-mailed the colleague to apologize for his bad actions and copied both his boss and his colleague’s boss on the e-mail. By copying their superiors, he was able to not only state his sincerity but to demonstrate it.
  3. Don’t be funny. Never use humor over e-mail when having a crucial conversation. It will almost always backfire. Share your facts, tell your story, and ask for the other person’s path.

Develop Your Crucial Skills

Image for

What's Your Style Under Stress?

Discover your dialogue strengths and weaknesses with this short assessment.

Take Assessment

Image for

Subscribe Now

Subscribe to the newsletter and get our best insights and tips every Wednesday.


Image for

Ask a Question

From stubborn habits to difficult people to monumental changes, we can help.

Ask a Question

Leave a Reply

Get your copies
The ideas and insights expressed on Crucial Skills hail from five New York Times bestsellers.


Take advantage of our free, award-winning newsletter—delivered straight to your inbox