🧭 What Great Leaders Do That Average Leaders Avoid

Jocko Willink on Hard Conversations

"The earlier you have a hard conversation the easier the conversation is...It's much easier for you to come up to me and say 'Hey Jocko, I noticed you didn't hit your numbers last week, is there any support you need from me? Is there any training that I can get for you?' It's much easier to have that conversation than 'Hey Jocko you've missed your numbers for six straight months and we're looking at demoting you or getting rid of you if you don't improve drastically. That's a much harder conversation to have, so have your hard conversations earlier - it will make your life a lot easier.'"

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How to Have Hard Conversations

Let’s get one thing straight…having hard conversations isn’t about being born a “tough talker.” It’s not a personality trait.

It’s a leadership skill. A communication skill. A life skill.
One that anyone can learn.

Because here’s the truth: The conversations you avoid are the ones that would change everything.

Why this matters: When you avoid difficult conversations, small problems become big problems. Teams break down and people lose trust in each other. Studies show this happens everywhere - from hospitals to offices to sports teams - and it kills performance when teams can't talk openly about what's wrong.

The research is clear:

• Google's Project Aristotle found that psychological safety, built through trust and open conversation, was the #1 driver of high-performing teams.

• A study by Bravely shows that 70% of employees avoid difficult conversations, while 53% handle "toxic" situations by ignoring them.

This is a universal leadership problem.
But it’s also a universal leadership skill if you’re willing to practice it.

The 4-Part Playbook for Hard Conversations

1: Connection Before Correction

Communication expert Jefferson Fisher calls this the secret opener to every hard conversation: "Thank you for making the time to talk with me...I need your help."

This immediately shifts the dynamic from confrontation to collaboration.

It's no longer me vs. you. It's us vs. the problem.

You become teammates in the process.

2: State Impact, Not Blame

Skip the accusations. Skip the assumptions. Lead with how the situation impacted you. Jocko Willink emphasizes that effective performance management starts with:

"I care about you as a person, I care about you as part of this team, and I care about your success in the future." 

This removes walls of defensiveness and invites real dialogue.

3: Move Early, Not Late

Hard conversations don't get easier with time. Just remember the initial Jocko quote from the beginning.

The longer you wait, the harder the conversation is. Be authentic and give real feedback in real time.

4: Ask + Listen + Embrace Silence

Conflict expert Adar Cohen's third rule: "Keep quiet. Don't panic in the few seconds it takes for people to respond; they just need time."

End with a question, then stop talking.

Let the silence do its job. Breakthroughs don't come from filling the air - they come from holding space.

➡️ Want to know the biggest mistake leaders make in difficult conversations? This week's Premium newsletter reveals the #1 mistake leaders make in difficult conversations (and how to avoid it). → Start your free trial today! 

🧠Questions to Ask Others You’re Leading

• If you're a manager or coach: Are you creating a culture where hard conversations are expected, not avoided? Do your players or staff know that feedback is a form of care, not criticism?

• If you're a parent or leader: Are you modeling the courage to say what needs to be said, even when it's uncomfortable? Do your kids or team see you prioritize truth over ease?

• If you're an athlete: Are you willing to speak up when something's off, even if it's not popular? How do you respond when a teammate holds you accountable?

Final Takeaway: Hard conversations are not a personality thing. They are a leadership thing. They are a skill set anyone can learn. And the truth is, the faster you run toward them, the faster everything gets better—your relationships, your teams, your life.

Sources:

1. Mastering Tough Conversations: Effective Strategies for Better Communication

2. Years of Mastering Hard Conversations in 20 Minutes | Jocko Willink | Dave Berke

3. Harvard Business School - How to Have Difficult Conversations with Employees

4. How to Lead Tough Conversations | Adar Cohen | TEDxKeene

Favorite Posts I Found This Week

Free Mental Fitness Links 👇

For coaches and leaders:

• 5 signs you are leading with high standards and compassion

• Brad Stevens on his non-negotiables in sports and life

• Thee story of how Jemal Singleton believed in Saquon Barkley more than himself

• The 8 attributes of connected teams

For athletes and performers:

• How to define success and the 4 costs of success

• John Wooden on being a great teammate

• What you need to know about motivation

• 6 steps to influencing your confidence

• Tom Brady defining greatness

What I am reading and listening to:

📚 Book: Trust and Inspire: How Truly Great Leaders Unleash Greatness in Others by Stephen Covey

🎥 Video: Ep. 002 - Overcoming Adversity, Interview with Drew Brees on The Jeff Fenster Show

🎧Podcast: Brad Stevens, Boston Celtics President and Former Head Coach | Transformational Coaching | Way of Champions Podcast
 

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