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The Leadership Podcast

The Leadership Podcast

Why do we do this?

We interview great leaders, review the books they read, and speak with highly influential authors who study them.

How we do this?

#1 We interview great leaders.
#2 We review the books great leaders read and write.
#3 We have fun!

Nov 14, 2018

Difficult conversations are part of the leader’s job when it comes to creating a strong organization. In this episode,  Jim and Jan share the tools they recommend to make these unavoidable conversations a little easier. In this episode, they answer listener questions all based on the topic of difficult conversations: The pitfalls of avoiding them, how to plan for them, and how to prevent the need for them in the first place.


Key Takeaways

[2:20] We tend to try and avoid difficult conversations that may lead to conflict. Sweeping problems and conversations under the rug may lead to loss of money, time, and employee morale. Team members look for their leaders to be firm about upholding standards, and when they don’t see that occurring, they may leave for a place that does.

[4:41] When approaching a difficult conversation, we must know the questions we want to ask, and have clarity on how we want to frame them.

[4:53] Good leaders set expectations before emotions run high.

[5:51] Q: How can you have the difficult conversations to build the person up and turn them around without ticking them off? A: This gets at the heart of leadership - balancing both results and people. It is important to give encouragement frequently from the start, and earn people’s trust to accept constructive yet difficult dialog.

[11:16] You can coach or train people just about anything, but there’s a cost / value curve. It takes time, resources and effort.

[14:54] Q: What do you do when someone doesn’t follow your advice? A: Ask questions regarding what isn't working, and figure it out together. It shows you have an intent to solve the problem rather than just cast doubt or blame.

[18:14] Strong leaders take the time to gather facts and ask questions before jumping to conclusion.

[20:30] Q: How do you handle divas? A: It depends on the diva! Do they ascribe to the core values, and produce results? We may be able to provide flexibility and leverage their skills, but they don’t get a pass or special treatment on how they treat others.

[23:45] Leaders must take a look and see if they are creating divas from the inside out.

[26:38] Good leaders set crystal clear expectations on both the performance and behavior sides.

[27:23] Jim admits that even he has been a diva before, but Jim suggests an alternate way to look at it is a rule breaker. It’s important in the following three areas to look to see if maybe it’s the organization's responsibility that would benefit from a change : Relationships, Results, and Rules.

[30:46] Take a look at your calendar, and look at how much time you are spending developing relationships. There is a correlation between how much time you spend doing this, and the time you worry about having difficult conversations.


  • “So much pain and suffering can be avoided it we had these difficult conversations.”
  • “Have the difficult conversations before emotions run high.”
  • “Being nice is not enough, we have to produce results.
  • Brilliant Jerks are Energy Vampires
  • “Leaders need to make sure they set their employees up for success.”
  • “Good leaders set the stage for difficult conversations by catching people doing well.”



Netflix Values

Ep 027: Positivity & Performance

Ep 047: Insights on How Individual Self-Awareness Affects Team Performance



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