The Biggest Mistake Leaders Make When They Avoid Difficult Conversations

The Biggest Mistake Leaders Make When They Avoid Difficult Conversations

No one enjoys having difficult conversations, but as a leader you’ll have to have them. No way around it. As parents, siblings, friends, co-workers; we need to embrace having those difficult conversations instead of avoiding them.

Personally, I’m a no B.S. straight shooter and can come across as confrontational because I don’t like avoiding difficult conversations; it bothers me when other’s avoid them. This has served me both well and bad. I’ve never employed family members. But I have employed friends and started businesses with friends. Unfortunately, some of those friends are no longer my friends. Why? Because of difficult conversations. Either having them, or letting time pass until it all comes to a head.

Whenever I felt someone was avoiding me, I’d confront them. Which also created a problem because confrontation is not the right approach to having productive conversations with people; it’s something I’ve had to learn how to change.

On a recent conversation with a friend, I found out he fired his brother. Well, they kept him on a contract but took him off payroll. Not because they wanted to cut costs, but because he isn’t living up to expecations and being accountable. There were no conversations about his lack of accountability before the firing. They only told him they were “cutting costs” and would have to move him to a per hour contract.

What’s the problem here?

You inhibit people’s growth when you avoid having a difficult conversation with them

You are making a big mistake if you fire someone before giving them a chance to improve, or don’t point out areas of improvement before hand. Basically, you inhibit people’s growth when you avoid having a difficult conversation with them; in my eyes, you become less of a leader when you avoid them because it shows you don’t care about the person.

How can you best approach difficult conversations?

I’ve sinced learned to reframe difficult conversations as discovery conversations and approach them with curiosity to learn about another person’s perspective. This changes everything because we have to converse with people, and conversation is the foundation of relationships; conversations become easier when you approach them with an open mind and curiosity.

Also, this will help you in the long run because the ability to follow up and build a relationship after a hard conversation matters just as much as the skill of tackling that initial difficult conversation.

Leadership is about communication

Most people don’t learn, and don’t care to learn, how to have difficult conversations. But avoiding them is mistake leaders can’t afford to make. Trust is the foundation of leadership, and effective leadership is not possible without effective communication skills. And, being skilled at having difficult conversations should be a the top of your personal development list if you are to become a better leader. Remember, we need to get comfortable with being uncomfortable – that is how we grow and develop.


Bottom line: The biggest mistake leaders make when avoiding difficult conversations is inhibiting other people’s growth. Real leaders don’t avoid tough conversations, they embrace them. Why? Because they know they can learn so much more from another person, and themselves, when they have them; which then deepens relationships and opens the door to unleashing others.