Coaching for Leaders

Oscar Trimboli: How to Listen

Oscar Trimboli is an author, host of the Apple award-winning podcast Deep Listening and a sought-after keynote speaker. He is passionate about using the gift of listening to bring positive change in homes, workplaces, and cultures around the world. Through his work with chairs, boards of directors, and executive teams, Oscar has experienced firsthand the transformational impact leaders and organizations can have when they listen beyond the words.

Oscar is a marketing and technology industry veteran with over 30 years experience across general management, sales, marketing, and operations for Microsoft, PeopleSoft, Polycom, Professional Advantage, and Vodafone. He is the author of the book, Deep Listening and now, his newest book, How to Listen: Discover the Hidden Key to Better Communication*.

In this conversation, Oscar and I explore several of the assumptions that tend to get in our way of listening well. Oscar highlights distinctions that will be useful mindsets for you in showing up better in future conversations. Plus, we discuss how listing goes far beyond simply asking questions.

Key Points

Before we begin listening, it is helpful to tune…much like as orchestra.

We can’t always give our full attention, but we can make the choice as to whether we are paying attention or giving attention.

As much as we intend otherwise, sometimes we listen less well in our closest relationships.

Aim to be curious instead of drawing conclusions.

Asking questions does not necessarily mean you are listening well. Aimless and arbitrary questions are everywhere.

Resources Mentioned

How to Listen: Discover the Hidden Key to Better Communication* by Oscar Trimboli

Interview Notes

Download my interview notes in PDF format (free membership required).

Related Episodes

The Way to Be More Coach-Like, with Michael Bungay Stanier (episode 458)

Four Habits That Derail Listening, with Oscar Trimboli (episode 500)

How to Genuinely Show Up for Others, with Marshall Goldsmith (episode 590)

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Megan Reitz: Speak Up

Megan Reitz is Professor of Leadership and Dialogue at Hult International Business School where she speaks, researches, consults and supervises on the intersection of leadership, change, dialogue and mindfulness. She is on the Thinkers50 ranking of global business thinkers and is ranked in HR Magazine’s Most Influential Thinkers listing. She has written Dialogue in Organizations and Mind Time.

She is a regular contributor to Harvard Business Review and her research has recently featured in Forbes, on the BBC, in TEDx talks, and in numerous academic and practice-based journals. Her latest research on employee activism was nominated for the Thinkers50 Breakthrough Idea Award. Her most recent book with John Higgins is titled Speak Up: Say What Needs to Be Said and Hear What Needs to Be Heard*.

Many leaders consider what they need to do in order to speak truth to others, but rarely focus on how to make it easier for people to speak to them. In this conversation, Megan and I explore what leaders can do in order to hear what needs to be heard. We share several tactics that will make it easier for others to surface what you need to hear.

Key Points

Speaking up and listening up go hand in hand. Power always affects what gets said and what gets heard.

A key checkpoint is whether or not you really value the opinion of others.

Where you have conversations can make a massive difference on how comfortable the other party is in surfacing an important message for you to hear.

Leaders who have margin in their daily schedules create space for the right moment to hear truth.

Proactively invite challenge and debate through specific invitations. One example: “What do you know that I need to know, but will never be told?”

Resources Mentioned

Speak Up: Say What Needs to Be Said and Hear What Needs to Be Heard* by Megan Reitz and John Higgins

Interview Notes

Download my interview notes in PDF format (free membership required).

Related Episodes

How to Ask Better Questions, with David Marquet (episode 454)

How to Speak Up, with Connson Locke (episode 546)

How to Use Power Responsibly, with Vanessa Bohns (episode 551)

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Bill George: True North

Bill George is executive fellow at Harvard Business School, where he has taught leadership since 2004. He is the author of four best-selling books: Authentic Leadership, True North, Discover Your True North, and 7 Lessons for Leading in Crisis.

He was chair and CEO of Medtronic, the world’s leading medical technology company. Under his leadership, Medtronic’s market capitalization grew from $1.1 billion to $60 billion, averaging 35 percent a year. Bill has served as a director of Goldman Sachs, ExxonMobil, Novartis, Target, the Mayo Clinic, and World Economic Forum USA. He has been named one of the Top 25 Business Leaders of the Past 25 Years by PBS, Executive of the Year by Academy of Management, and Director of the Year by National Association of Corporate Directors. He is the author with Zach Clayton of True North: Leading Authentically in Today's Workplace, Emerging Leader Edition*.

We’ve all seen leadership go badly and most of us struggle with tendencies to get pulled off course. In this conversation, Bill and I explore the five most common archetypes that tend to derail leaders and the antidote that prevents them. We also discuss how we can recognize these tendencies in ourselves so that we can do better for others.

Key Points

Five archetypes of leadership derailment:

Imposters: political animals who figure out who their competitors and then eliminate them.

Rationalizers: masters of denial who don’t take responsibility themselves.

Glory seekers: motivated by the acclaim of the world.

Loners: they believe they can make it on their own and reject feedback.

Shooting stars: they build shallow foundations and move on quickly to the next things, often avoiding commitment.

Antidotes to leadership derailment:

Write down the most difficult ethical dilemma you are currently facing and chronicle the “least generous” interpretation of your actions.

Project forward a decade and assume the worst: you have derailed in a major failure. Envision the situation in which you could lose your way.

Resources Mentioned

True North: Leading Authentically in Today's Workplace, Emerging Leader Edition* by Bill George and Zach Clayton

Interview Notes

Download my interview notes in PDF format (free membership required).

Related Episodes

Discover Your True North, with Bill George (episode 225)

Leadership Lies We Tell Ourselves, with Emily Leathers (episode 479)

How to Help Your Manager Shine, with David Gergen (episode 588)

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Amy Gallo: Getting Along

Amy Gallo is an expert in conflict, communication, and workplace dynamics. She combines the latest management research with practical advice to deliver evidence-based ideas on how to improve relationships and excel at work. In her role as a contributing editor at Harvard Business Review, Amy writes about interpersonal dynamics, communicating ideas, leading and influencing people, and building your career.

Amy is co-host of HBR's Women at Work podcast and author of both the HBR Guide to Dealing with Conflict and Getting Along: How to Work with Anyone (Even Difficult People)*.

In this conversation, Amy and I discuss one of the most common questions she receives from leaders: how do I handle a colleague who’s passive aggressive? We examine what causes this behavior, how to respond to it, and what to avoid that could worsen the relationship. Plus, we discuss the intention that leaders can bring in responding to passive-aggressive behavior that will help everybody move forward.

Key Points

Don’t use the “passive-aggressive behavior” to label someone. It rarely helps and often results in more defensiveness.

Focus on the other person’s underlying concern or question rather than how they are expressing it. Not everyone is able to discuss thoughts and feelings openly.

Consider doing hypothesis testing to determine what’s next. Language like, “Here’s the story I’m telling myself…” can help everyone move forward without assigning blame.

When making a direct request, stick to the facts. Review past behavior like you’re a referee vs. a fan.

Artificial harmony is a danger spot for teams and leaders. Setting norms can help to reduce passive-aggressive behavior.

Resources Mentioned

Getting Along: How to Work with Anyone (Even Difficult People)* by Amy Gallo

Interview Notes

Download my interview notes in PDF format (free membership required).

Related Episodes

The Way to Have Conversations That Matter, with Celeste Headlee (episode 344)

Four Habits That Derail Listening, with Oscar Trimboli (episode 500)

How to Prepare for Conflict, with Amy Gallo (episode 530)

The Way to Get People Talking, with Andrew Warner (episode 560)

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Kwame Christian: How to Have Difficult Conversations About Race

Kwame Christian is a best-selling author, lawyer, professor, and the Managing Director of the American Negotiation Institute. He has conducted countless specialized trainings worldwide and is a highly sought after keynote speaker. His best-selling book, Finding Confidence in Conflict has helped countless individuals overcome the fear, anxiety, and emotion associated with difficult conversations. The book was inspired by Kwame’s TED Talk with the same name that has over 250,000 views. He’s also host of the Negotiate Anything Podcast, the most popular negotiation podcast in the world.

Kwame was the recipient of the John Glenn College of Public Affairs Young Alumni Achievement Award in 2020 and the Moritz College of Law Outstanding Recent Alumnus Award 2021. Additionally, Kwame is a business lawyer at Carlile, Patchen & Murphy LLP and serves a professor for The Ohio State University’s Moritz College of Law in its top-ranked dispute resolution program and Otterbein University’s MBA program. He is also a Contributor for Forbes and his LinkedIn Learning course, How to Be Both Likable And Assertive, was the most popular course on the platform in July of 2021. He is the author of How to Have Difficult Conversations About Race: Practical Tools for Necessary Change in the Workplace and Beyond*.

In this conversation, Kwame and I discuss how to begin a difficult conversation about race. We explore the key questions that each of us should ask ourselves so that we can determine in advance what we want to gain from a tough conversation. Finally, we look at the three critical things to say in the first 30 seconds that will help you start an important conversation that helps everybody move forward.

Key Points

It's hard for someone else to appreciate how much of a person's identity affects every other area of their lives until you've lived it.

People explain away racism because they don’t like it and don’t want it to be true.

Whether you think a conversation is about race or not, if it’s about race for the other person then you’re having a conversation about race.

There questions to ask yourself before a conversation:

What do I hope to accomplish in this conversation?

Given what I know about them and the situation, what is likely to be their goal?

What are three questions I can ask them that will help me to understand their position?

Use situation, impact, and invitation as the starting point for a difficult conversation. Usually this is less than 30 seconds.

“Naked facts” reduce the likelihood that someone will dispute the premise of what you are addressing.

Resources Mentioned

How to Have Difficult Conversations About Race: Practical Tools for Necessary Change in the Workplace and Beyond* by Kwame Christian

Negotiate Anything podcast

Interview Notes

Download my interview notes in PDF format (free membership required).

Related Episodes

The Way Into Difficult Conversations, with Kwame Christian (episode 497)

How to Reduce Bias in Feedback, with Therese Huston (episode 510)

The Way Managers Can be Champions for Justice, with Minda Harts (episode 552)

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Lesson 4: How to Respond to Obstacles

How you respond when an employee hits obstacles will have huge implications for their growth. Several key questions will help you both move forward.

Key Points

Use the “see one, do one, teach one” framework when teaching a skill for the first time.

Questions like, “What do you think is the next step?” or “How can I help?” or “What do you want from me?” can help the employee move forward while still helping them keep ownership for the results.

Effective Delegation of Authority by Hassan Osman is a concise, useful read for even more support on delegation.

Academy Applications Close Friday, September 9th

The Academy is an intimate cohort of participant leaders who work personally with me to accelerate their leadership development and organizational results. Discover more and submit your application by Friday, September 9th.

Related Episodes

The Way to Stop Rescuing People From Their Problems, with Michael Bungay Stanier (episode 284)

Five Steps to Hold People Accountable, with Jonathan Raymond (episode 306)

Effective Delegation of Authority, with Hassan Osman (episode 413)

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Lesson 3: The Delegation Dialogue

Good delegation is an ongoing dialogue. Once you’ve defined what done looks like, they draft a plan, review it with you, and you both establish milestones.

Key Points

Once you’ve defined what done looks like, ask the employee to draft a plan for how they will meet the objectives.

When reviewing an employee’s plan, resist the temptation to coach them on minor issues that aren’t likely to affect the overall outcome.

Establish milestones upfront with an employee to prevent micromanagement. Decide together what the cadence of checkins should look like.

Academy Applications Close Friday, September 9th

The Academy is an intimate cohort of participant leaders who work personally with me to accelerate their leadership development and organizational results. Discover more and submit your application by Friday, September 9th.

Related Episodes

Effective Delegation of Authority, with Hassan Osman (episode 413)

The Way to Be More Coach-Like, with Michael Bungay Stanier (episode 458)

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Lesson 2: Defining Done

Before you ever start a delegation conversation with an employee, it’s essential to define what done looks like. Use time, cost, and quality to frame success.

Key Points

Defining done starts with the manager, before any conversation with an employee.

Healthy discussion, negotiation, and innovation comes after you define what done looks like.

Clarity on time, cost, and quality are essential when determining what done looks like.

Academy Applications Close Friday, September 9th

The Academy is an intimate cohort of participant leaders who work personally with me to accelerate their leadership development and organizational results. Discover more and submit your application by Friday, September 9th.

Related Episodes

Effective Delegation of Authority, with Hassan Osman (episode 413)

How to Define a Role, with Pat Griffin (episode 517)

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Lesson 1: The Key Realities of Effective Delegation

Delegation brings many benefits to others and you. Once you’re ready to begin delegating better, knowing these realities will help accelerate your results.

Key Points

Delegation is one of the best and most immediate ways to develop others.

When you start delegating more, things almost always get worse before they get better.

You’ll need to make peace with accepting some “B” work if you’re used to only getting “A+” work from others and yourself.

Academy Applications Close Friday, September 9th

The Academy is an intimate cohort of participant leaders who work personally with me to accelerate their leadership development and organizational results. Discover more and submit your application by Friday, September 9th.

Related Episodes

How to Succeed with Leadership and Management, with John Kotter (episode 249)

Effective Delegation of Authority, with Hassan Osman (episode 413)

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David Hutchens: Story Dash

David Hutchens helps leaders find and tell their stories. He works with leaders around the world to find, craft, and tell their most urgent stories for the purpose of creating shared meaning, preserving culture, disseminating learning, and speeding change in organizations.

He has taught the Storytelling Leader program at some of the most influential organizations — and he’s written many books, including the Circle of the 9 Muses and The Leadership Story Deck. He is the co-creator with longtime friend of the show Susan Gerke of the GO Team program. He's also the author of the new book, Story Dash: Find, Develop, and Activate Your Most Valuable Business Stories…In Just a Few Hours.

In this conversation, David and I discuss how to find stories that you can use in your organization. We reflect on the reality that we both hear many leaders say to us: “How do I find the right stories?” David then shares the key principles and steps that every leader can take to surface and curate the best stories.

Key Points

The “Us At Our Best” taxonomy is what it looks like when are are delivering with energy and excellence. A recent Southwest Airlines story is an example of this.

Find the area the area of your work where you need to influence the emotional system.

Trust stories about small moments. Don’t attempt to create an epic drama of huge importance. The best stories are individual incidents that send a bigger message.

Formal story mining can be done alone or as team building. Institutionalizing practices like story sharing can help this happen regularly and naturally.

When informally collecting stories, listen for time, place, and person as signals that a story is beginning.

Resources Mentioned

Download a free set of Story Deck cards or…

Reach out to David directly at [email protected] for more free resources

Purchase the full set of Leadership Story Deck by David Hutchens

Related Episodes

How to Create an Unstoppable Culture, with Ginger Hardage (episode 350)

Three Stories to Tell During Uncertainty, with David Hutchens (episode 486)

The Way to Earn Attention, with Raja Rajamannar (episode 521)

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