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Tame the High Stakes Conversation

David Porter
The Startup
Published in
4 min readApr 12, 2018

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A CEO once asked me, “Is there anything you are afraid of?” My quick reply, “Not at work.” He just shook his head.

My response was an unintended exaggeration. The reality is that I’ve had my share of fears at work, but having difficult conversations isn’t one of them, and that was the context of his question.

I think it’s natural for us to enter higher stakes discussions with bosses, and even peers, with some trepidation. Most of the fear comes from feeling we aren’t enough for the situation. Smart enough. Strong enough. Competent enough. Skilled enough. Old enough. Young enough. Your personal not enough here__________.

It is likely that the other person in the discussion feels much like we do. They may mask it with a bit of bravado, but the fact remains that no matter what level of success they have reached, the inner voice continually butts into their thoughts. Just like it does in all of us. The skilled at this often choose only to notice the noise and move on without reacting to its unhelpful message.

The fact that we are more alike than different can empower us. When asked about being afraid, it was related to an objectively influential person in my orbit. In my view, I had a message to deliver to someone who also puts his pants on one leg at a time. I had prepared for questions and planned to convey the message because it was my job. I didn’t spend any time psyching myself out about failing. I expected to succeed in getting my message across. It was no more complicated than that, and the discussion went well.

As you think about holding a high stakes conversation, there are some helpful success strategies:

1. Give yourself clarity on the discussion outcome. What is it you want when it’s done? Is it an improved relationship? Is it higher pay? Is it a better job? Is it enhanced credibility? Whatever it is, write down the outcome before creating your message.

2. Know your topic cold. To be clear, this is not an exercise to anticipate the 100 questions that may be asked in a 5-question meeting. That type of preparation locks us up and leads to exhaustion and frustration. In the unlikely event that a question surprises you, it’s perfectly fine to say, “I don’t know. But I will find out.”

3. Prepare to listen to what’s said actively and, even more so, for what’s not. If your message is falling flat, it may be because the other person has something on his mind unrelated to the discussion. He may believe the chat should go a different way. When in doubt, ask for clarity. Is this discussion meeting your needs? Is there something else we should talk about first? Are we covering the things that you care about? Listen and adjust.

4. Simplify your message. Speaking for an hour about something is easier than speaking for one minute about it. Taking the time to boil your message down to its essence can be difficult, but it’s worth the investment.

5. Stay present along the way. Remember that non-verbal cues represent 60% of meaning in a conversation. It serves you to stay in the moment and notice changes in voice, facial expressions, and body language. These cues will guide you to adjust your approach as needed.

6. Use fear as a signal to step up. If you are fearful, nervous, or otherwise out of sorts, remember that these emotions aren’t a stop sign. Use emotions to motivate you into action. When emotions rise, ask yourself, “What else could this mean? How can I use this feeling to help me right now?” Practice your discussion with a respected friend, partner, or peer to work through the jitters.

7. Hit pause on your ego. The temptation to be right in a difficult discussion can be significant. Go back to your outcome and make sure you take the breaths required to keep you from going down a seemingly righteous path that ends with a damaged relationship.

Takeaway: Taking the time to prepare yourself for high stakes conversations expands your ability to hold them. Holding difficult discussions expands your leadership abilities. Developing your leadership abilities increases your influence. Increasing your impact helps build high-performing teams and companies. High-performing teams consistently deliver results.

Call to Action

You can learn more about David Porter Advisors by visiting our website here. I’m ready to have the right conversation when you are. We’ll both walk away with something learned.

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