A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett
Rachel Lockett, an executive coach and former HR leader at Pinterest and Stripe, discusses critical leadership skills like knowing when to coach versus advise, avoiding burnout by aligning with gifts, fostering healthy co-founder relationships, and improving interpersonal communication for more effective and fulfilling work.
Deep Dive Analysis
14 Topic Outline
The Human Side of Business Building
Knowing When to Coach Versus Advise
Developing Active Listening Skills
Utilizing Powerful Questions with the GROW Model
Live Coaching Demonstration: Addressing Work Overload
Strategies for Avoiding Burnout and Designing an Energizing Career
Building and Sustaining Healthy Co-Founder Relationships
Navigating and Resolving Co-Founder Conflict
Improving Interpersonal Communication with Nonviolent Communication
Reframing Difficult Conversations as Growth Opportunities
Applying the 'Enthusiastically Rehire' Test for Talent
Aligning Company Vision and Goals with a One-Page Plan
AI's Role in Enhancing Executive Coaching
Final Thoughts on Connection and Leadership
7 Key Concepts
Coaching vs. Advising
Leaders often default to advising, but coaching empowers teams to solve problems themselves, fostering ownership and motivation. Advising is best for urgent issues or when the team lacks necessary skills, but leaders often over-index on this approach.
Active Listening (Three Levels)
Active listening progresses from internal focus (Level One), to understanding spoken words (Level Two), to 'global listening' (Level Three). Level Three involves hearing beneath words, noticing body language, tone, and context, allowing for reflection of deeper insights.
Powerful Questions
These are questions designed to foster insight and lead to new solutions without guiding the individual to a specific answer. They help unlock a person's own understanding and potential paths forward.
Designing Your Life Around Gifts
This concept suggests individuals experience more energy and inspiration when they spend the majority of their time (ideally 80%) operating from their natural strengths and passions. It requires self-awareness and intentional career design to align with these gifts.
Goal of Conflict (Mutual Understanding)
The primary purpose of engaging in conflict is not to prove someone wrong, but to create shared understanding between parties. This approach allows for empathy and collaborative problem-solving rather than defensive reactions.
'Enthusiastically Rehire' Question
A rigorous talent assessment question, used at Stripe, that asks if a leader would enthusiastically rehire an individual for their current role. This provides a clear, binary indicator for making talent decisions and ensuring a high-performing team.
One-Page Plan
A simplified framework for leadership teams to align their vision, values, strategic intentions, KPIs, annual goals, and quarterly goals on a single page. It ensures clarity and coherence across the company, helping employees understand how their work ladders up to the big picture.
11 Questions Answered
Most leaders, especially technical ones, assume they must have all the answers, but great leaders know when to coach their team to solve problems themselves rather than always advising.
Advising is appropriate when there's an urgent issue, or the person coming for help lacks the necessary skills, and the leader has a specific answer they want to drive.
Leaders can practice 'Level three global listening,' which involves hearing beyond words, noticing body language and tone, understanding context, and reflecting deeper insights back to the speaker.
By intentionally designing their lives to spend 80% of their time in their natural gifts and strengths, identifying what gives and depletes energy, and communicating these insights to managers or co-founders.
For two weeks, every night, reflect on and write down five things that gave the most energy and five things that depleted energy that day, then look for patterns.
65% of startups fail due to co-founder conflict, often because founders don't make time to connect. Strengthening requires self-awareness of individual dynamics and conscious commitment to the relationship through regular check-ins and dedicated space for connection.
The goal is to create mutual understanding, not to convince the other person they are wrong, by sharing one's own observations, feelings, and needs without blame.
Reframe ambivalence and interpersonal challenges as growth opportunities, recognize one's own contribution to the conflict, and approach the conversation with humility and curiosity.
Ask the question, 'Would I enthusiastically rehire this person for the same role?' This provides a clear, binary answer that helps clarify talent decisions.
A one-page plan aligns vision, strategy, goals, and values, providing clarity for the entire company, ensuring everyone understands priorities, and how their work contributes to the bigger picture.
AI tools like Granola help coaches take notes, synthesize insights, and track client patterns. AI can also assist in planning retreats and is being explored for providing tactical support to clients between sessions.
10 Actionable Insights
1. Shift from Advising to Coaching
Equip your team to solve problems by coaching them instead of always providing answers, which fosters their brilliance and motivation. Reserve direct advice for urgent issues or when skills are genuinely lacking, but avoid making it a guessing game.
2. Master Global Active Listening
Practice “level three listening” by observing body language, tone, and context to understand underlying emotions and unspoken communications. This deep engagement fosters connection, motivates your team, and reveals deeper insights into situations.
3. Ask Powerful GROW Questions
When team members bring problems, use the GROW model (Goal, Reality, Options, Way Forward) to ask insightful questions that help them uncover their own solutions. This approach empowers them and clarifies their thinking, even if you initially disagree with their ideas.
4. Align Work with Your Gifts
Combat burnout by identifying your natural strengths and what energizes you, aiming to spend 80% of your time in these “gifts.” Track daily energy, seek feedback, and communicate your interests to your manager to align your role with your zone of genius.
5. Nurture Co-Founder Relationships
Build strong co-founder relationships through deep self-awareness and understanding each other’s strengths and weaknesses, using tools like the Enneagram. Consciously commit to the relationship with regular check-ins and “balcony time” to discuss alignment and address unspoken issues.
6. Navigate Conflict with NVC
Approach difficult conversations with the goal of mutual understanding, not proving your point, using the Nonviolent Communication (NVC) framework. State factual observations, express your feelings without blame, articulate your unmet needs, and make a small, achievable request to foster empathy and open dialogue.
7. Implement a One-Page Plan
Create a simple, one-page plan that clearly outlines your company’s vision, values, strategic intentions, KPIs, and goals from top to bottom. Combine this with a regular operating rhythm for reflection, discussion, and addressing “inconvenient truths” to foster clarity and alignment.
8. Apply “Enthusiastically Rehire” Test
When evaluating team members, ask if you would enthusiastically rehire them for the same role; a “no” indicates a need for action. This binary question provides clarity on talent fit, prompting necessary changes like re-evaluation, performance plans, or role adjustments to maintain a high-performing team.
9. Embrace Fear as Growth Compass
View things you fear or avoid, especially in interpersonal dynamics, as opportunities for growth and learning. Lean into these moments, acknowledge your feelings, and ask “What’s important here? What do I have to learn?” to build skills and foster deeper connections.
10. Actively Foster Team Connection
Recognize that business building is a human endeavor in an increasingly lonely world, and actively foster connection within your teams. Create environments where genuine human interaction is inevitable to build healthier teams, have more fun, and achieve better business outcomes.
8 Key Quotes
Most people aren't listening. They're just waiting for their turn to talk.
Rachel Lockett
The goal of any conflict is to create mutual understanding.
Rachel Lockett
When people are in their gifts and their strengths, firmly, most of the time, they have more energy.
Rachel Lockett
It's no one else's job to help you live in your gifts... it's your job to navigate your career.
Rachel Lockett
65% of startups fail because of co-founder conflict.
Rachel Lockett
The quality of our relationships determines the quality of our life.
Rachel Lockett
How are you complicit in creating the conditions you say I don't want?
Rachel Lockett
If you can see your path laid out in front of you, step by step, it's not your path. Your own path you make with every step you take. That's why it's your path.
Rachel Lockett
3 Protocols
Identifying Your Gifts and Energy Sources
Rachel Lockett- For two weeks, every night, reflect on and write down the five things that gave you the most energy that day.
- For two weeks, every night, reflect on and write down the five things that depleted your energy the most that day.
- Look for patterns in your reflections to understand your natural gifts and what activities are exhausting.
- (Optional) Ask 5-10 people in your life, 'When I walk in the room, what shows up? What are my strengths? What are my gifts?'
- (Optional) Review your calendar for the last month, noting activities you were excited to do versus those you dreaded, and identify common themes.
- Communicate your gifts and interests to your manager and team to align your role with your strengths and the business's needs.
- Take small, intentional steps to incorporate more energy-giving activities and reduce depleting ones, even if it's a simple change like reading 30 minutes before bed.
The GROW Model for Coaching
Rachel Lockett- **G (Goal)**: Ask questions about what success looks like or the desired outcome for the situation.
- **R (Reality)**: Ask questions about the current challenges, where the person is stuck, or what they have already tried.
- **O (Options)**: Ask questions to expand opportunities and explore various paths or choices available to the person.
- **W (Way Forward)**: Ask questions to help the person define concrete next steps they will take to move towards their goal.
Nonviolent Communication (NVC) Framework for Difficult Conversations
Rachel Lockett- **Observations**: State factual observations of what is happening, without judgment or interpretation (e.g., 'I noticed that in the last three sprint planning meetings, you didn't invite me').
- **Feelings**: Express your feelings without blame, focusing on an emotion word (e.g., 'I felt anxious,' not 'I feel like you're being a jerk').
- **Needs**: Articulate your universal human needs related to the topic that are not being met (e.g., 'I have a need for clarity' or 'I have a need for collaboration').
- **Request**: Make a specific, achievable request that helps the other person meet your needs and feel successful in connecting with you (e.g., 'I'd like to ask you next time you have a sprint planning meeting to include me as optional').