Mastery of startup communication: having a difficult conversation


As a startup founder, effective communication and negotiation skills are perhaps the most important skill for success. This short guide provides valuable insights and tips drawn from our professional experience and renowned works on the subject, such as Dale Carnegie’s “How to Win Friends and Influence People” and Chris Voss’s “Never Split The Difference”.


1. Preparation: discover the black swans

Active listening helps build relationships and provides opportunities to collect valuable information. Before entering into a difficult conversation with one of your startup’s stakeholders, it’s a good idea to seek genuine feedback from other relevant stakeholders relevant to the situation. It is likely that you will discover unexpected insights that may add to your understanding of the situation you are dealing with with the scheduled call. Actively listening to other parties and gaining a deeper understanding of your counterpart and their circumstances can also save valuable time by ensuring you don’t knock on the wrong door.

2. Emotional Defusion: Use mirroring and an accusation audit

Most difficult conversations are difficult because they carry an emotional charge for one or both parties for one reason or another. Passing on this emotional charge right at the beginning of the conversation is a prerequisite for having a productive and rational discussion.

To do that, you can use two techniques recommended by Chris Voss. First, you can use mirroring (rephrasing what the other person said and repeating it) to show that you understand the other party’s position and feelings.

Second, you can use an accusation check. You can “blame” yourself for the emotional charge in the conversation. This spreads tension and encourages the other person to offer support rather than blame.

3. Connection: Use active listening and tactical empathy

Active listening is essential for engaging in meaningful conversations. Avoid the usual habit of waiting your turn to speak. Instead, focus on understanding the other person’s point of view, needs, and desires. By really listening and empathizing, you can create a connection and drive action. Remember that it’s crucial to prioritize what the other person wants, rather than just focusing on your own goals.

Most decisions are driven by emotions. Having good rational arguments for what you’re doing or what you’re trying to get the other party to do is important, but it’s just as important (if not more important) that they feel comfortable and understood in your business.

4. Seriousness: Beware of a Fake “Yes”

Finally, after creating a healthy emotional climate for the conversation and a mutual sense of understanding and connection, it is important to steer the conversation toward the desired action afterwards.

That said, while it’s important to be assertive in what you’re trying to achieve, it’s also important not to be pushy and see if there’s a real desire (or lack thereof) for action on the part of the other party.

In negotiations, there are three types of “yes”: affirmation, commitment, and falsification. An affirmation “yes” simply confirms a statement, while a commitment “yes” indicates a willingness to take action. This is what you usually aim for.

However, many people use a false “yes” as a defense mechanism to avoid confrontation. This can lead to wrong expectations, which in turn hinders progress. Encourage honesty and sincere opinions from your counterparts, even if it means hearing a “no.”

In short, effective handle a difficult conversation is a skill you must acquire if you want to become a successful startup founder. Here’s a brief outline of how to do it:

  1. Prepare and discover unexpected bits of information
  2. Defuse emotional tension through mirroring and an impeachment audit
  3. Build trust with the other party – actively listen
  4. Move the conversation toward a commitment to action, but avoid a false commitment