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difficult conversations

A guide to the best B2B podcast coverage of difficult conversations - the shows and 15 episodes that go deepest, ranked by substance, not downloads.

Leading teams requires having hard conversations - whether managing underperforming middle managers, addressing accountability gaps, or delegating without guilt. These episodes explore how to approach difficult moments with calm strategy, how leaders can accept that upsetting people is sometimes necessary, and frameworks like the Toltec Agreements that help reframe management conversations for better outcomes.

Best shows on difficult conversations

Best episodes on difficult conversations

  1. 173 - How to have a difficult conversation

    Your Business Hour · 2026-06-23

    80 / 100

    …And as you can imagine, that has a significant number of difficult conversations both with parents, social workers, schools, other key stakeholders in child protection plans.…

  2. Emotional intelligence in customer success with Jenelle Friday

    CS School · 2024-08-08

    78 / 100

    …Uh, so for our listeners, we're going to be talking about self awareness, differentiating between empathy and eq, difficult conversations, uh, and training and development and things like that.…

  3. How to manage the priorities between the executive team and the investor

    The Private Equity Podcast, by Raw Selection · 2026-05-19

    72 / 100

    …So difficult conversations are avoided by the team.…

  4. 175 | Setting Expectations That Remove Confusion (and Reduce Your Stress by 70%)

    Women of Faith in Leadership · 2026-08-03

    61 / 100

    …In the Difficult Conversation Script Pack, I'm going to share with you different angles of how you can approach different and, um, difficult conversations.…

  5. Why Do Leaders Avoid the Conversations That Would Actually Fix Everything? | Neuroscience in Leadership

    AI Cafe Conversations · 2026-06-10

    59 / 100

    …And here is what most leadership books get wrong about difficult conversations.…

  6. Episode 43: Trust the Process: How to succeed as a first-time manager with Stephanie Herre (Leadership Coach, Sales Leader at Remote.com, Ex-Cisco and SAP)

    Teams at Work by BUNCH · 2023-07-07

    55 / 100

    …No, how do you train your communication skills? How do you become a better active listener? Uh, how do you handle difficult conversations?…

  7. Middle Management Meltdown: Are They Breaking?

    The Digital Transformation Playbook · 2026-07-01

    54 / 100

    …176 00:07:52,480 - > 00:07:55,120 Difficult conversations are one of the biggest gaps, and they've 177 00:07:55,120 - > 00:07:57,920 been identified as one of the biggest gaps for managers.…

  8. Why Leaders Avoid Difficult Conversations - Episode 7

    Leadership & Management Reset Podcast · 2026-04-02

    50 / 100

    …It is all about avoiding difficult conversations.…

  9. Episode 5: Nice vs Kind Leadership: Why Being "Nice" Can Undermine Your Team

    Leadership & Management Reset Podcast · 2026-03-01

    49 / 100

    …And letting standards slide to avoid tension and ultimately delaying difficult conversations.…

  10. 181 | What to Do When Everything Feels Urgent

    Women of Faith in Leadership · 2026-09-14

    43 / 100

    …And actually, this is something I teach a lot when it comes to difficult conversations, too, because so much of our anxiety around those conversations come from feeling like we have to know exactly what to say in the moment.…

  11. 168 | Delegate Without Feeling Guilty

    Women of Faith in Leadership · 2026-06-08

    41 / 100

  12. How to Hold Your Team Accountable - Episode 9

    Leadership & Management Reset Podcast · 2026-04-29

    39 / 100

    …And if you're wanting some support and having difficult conversations, then please listen to episode 7 of this podcast where I've taught that through.…

  13. Why It's Okay to Upset People When You Lead | Joanna Howes

    The Courageous Leaders Podcast · 2026-06-25

    36 / 100

  14. 170 | Solving Problems Like Jesus - Calm, Wise, Strategic Leadership Under Pressure

    Women of Faith in Leadership · 2026-06-22

    30 / 100

  15. Episode 134: Your Team Isn't Burned Out. They're Exhausted by Bad Behavior.

    Leadership Sandbox · 2026-05-21

    …Continue building leaders capable of having difficult conversations.…