Secrets to not suck at difficult conversations with people

Most people are significantly worse at crucial conversations than they think.

Improving your difficult conversations can unlock a year of progress.

👊 The Punch List:

  • 50% of managers cited difficult conversations as the biggest challenge they face in their roles.

  • 25% of managers have admitted to avoiding difficult conversations for over a year.

  • Most people are significantly worse at crucial conversations than they think.

  • With 3 secret keys you can easily master a majority of difficult convos.

3 Keys to Difficult Conversations with People

Choose the right channel

This simply means deciding on where on how to engage in your difficult conversation. The same conversations on different channels are not made equal. You need to have difficult convos on channels that promote safety, equality, and transparency.

In the real world you should take note of the modes of communication you engage well in. If you’re a great texter, try to have difficult convos there. If you need more energy and presence, choose to have your conversations in person.

Examples of choosing the right channel include, not breaking up with someone through text or writing a letter of dissatisfaction rather than confronting a retail employee.

Control what you focus on

This simply means making a point to stay focused in your difficult conversations. Because crucial convos include high stakes, differing opinions, and strong emotions, it’s easy to get distracted. You should write down the main goal to focus on, and every point or concern you want addressed in the convo.

In the real world always take a moment to write notes on the difficult conversation beforehand if possible. You should write down the number one goal you want to accomplish in the conversation. Sometimes you’ll have to break mid convo to write out thoughts and concerns rather than speak with no focus.

Examples of controlling what you focus on include sharing to a manager that you specifically want a refund for your undercooked food, or letting a friend know you specifically want to vent about an incident, and having all your points ready beforehand.

Focus on what you control

This simply means only putting energy into things you have control over. Rather than pointing fingers, play the one player blame game. Nine times out of ten difficult conversations need a resolution and the sooner you take action, the sooner you can resolve the issue.

In the real world you should share your point of view but put most of your focus on the things you can actually change. Don’t be afraid to be the bigger person and always choose to be the first to take action. This shows you are willing to “lose” for the greater good of all parties.

Examples of focusing on what you can control are being the one to initiate a difficult conversation, and taken time to understand what part you played in an unforeseen breakup.

Overall, if you want to build impactful businesses and reach your full potential you’ll have to deal with other humans. And sometimes humans disagree passionately. The better you get at engaging in difficult conversations, the better you get with all kinds of people. Nice, mean, sweet, or harsh.

As WIPs, we can use these skills to resolve issues with enemies, negotiate on our behalf, and stand up for others that are inspired by our progress.

So the next time you have a difficult convo, resist the urge to divide and instead choose to unify…

In progress,


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