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A Guide to Difficult Conversations
& High-Trust Teams

Rachel Lockett
Executive coach; former HR leader at Pinterest and Stripe
NOV 23 2025
The Thesis

The Quality of Our Relationships
Determines the Quality of Our Life

LISTENASKUNDERSTAND
"The goal of any conflict is to create mutual understanding."
  • Professionals have feelings. Tech pretends work is purely logical, and it isn't.
  • People come into conflict ready to prove their point. That is the wrong goal.
  • If you cannot have conflict, you cannot have healthy relationships.
  • There is always something you are doing to contribute. Take one hundred percent responsibility for your part.
Framework

Two Skills for Leader Coaching

INTERNALFOCUSEDGLOBAL
  • Level 1, internal: your own inner dialogue is drowning theirs out
  • Level 2, focused: you can repeat their words back, the shape of a good one-on-one
  • Level 3, global: hearing tone, body language and context beneath the words
  • Powerful questions: the GROW model, Goal, Reality, Options, Way forward
Building High-Trust Teams

NVC: Four Steps for Hard Conversations

  • Observations: state what happened factually, a photo everyone would agree with
  • Feelings: name your emotions without blame, "I felt anxious," "I felt confused"
  • Needs: the universal human need of yours that isn't being met, clarity, collaboration, connection
  • Request: an olive branch, small enough that the other person can easily meet it
The goal of conflict

The goal of any conflict is to create mutual understanding, not to convince the other person that what they are doing is wrong.

The enthusiastic-rehire test

Stripe's question for talent: would you enthusiastically rehire this person for the same role? The gut answer is honest and clarifying.

Playbook

How to Coach, Not Advise

  • Ask before advising: "Do you want advice, or do you want some space to think about it? Can I help you think it through?"
  • Use "help me understand" when a report brings you an idea you would reject
  • Advise when the issue is urgent or the person lacks the skill. Otherwise, coach.
  • Aim for about fifteen percent more space in your one-on-ones for open-ended questions
The design-your-life connectionRachel's aim is that leaders spend eighty percent of their time in their gifts. The tool: two weeks of nightly reflection, five things that gave you energy today and five that depleted it.
Contrarian

Coaching & Conflict Myths

✗The goal of conflict is to convince themINSTEAD →✓ "The goal of any conflict is to create mutual understanding."
✗Great leaders always have the answerINSTEAD →✓ When you try to advise all the time, you train your team to bring you every hard problem.
✗Tech is purely logicalINSTEAD →✓ "Professionals have feelings." Ignore them and they bubble up, and you act unconsciously from them.
✗Avoid the conversation you're afraid ofINSTEAD →✓ What you avoid is where the learning is. You care, and something is at stake.
Based on Rachel Lockett's episode on Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTube
GO DEEPER IN THE EPISODE
04:58 The human side of business building09:00 Coaching vs. advising13:09 Skill 1: Active listening18:37 Skill 2: Powerful questions24:49 Real-life coaching example27:36 Live coaching example with Lenny41:55 Addressing burnout in tech51:03 Spending more time working toward your goals53:09 Discovering her passion for executive coaching57:36 It's your job to navigate your career58:44 Why Rachel says to start small01:00:49 Building strong co-founder relationships01:06:50 Handling co-founder conflicts01:12:35 Improving interpersonal skills with team members01:20:28 Reframing difficult conversations as growth opportunities01:31:47 The one-page plan for company alignment01:36:50 Leveraging AI in coaching and personal development01:42:04 Lightning round and final thoughts
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