Make sure to schedule 1-on-1 coaching sessions at the same day and time every month. Meetings should occur indefinitely since new issues always emerge. Any topic should be fair game, from improving current performance to reaching career aspirations.

The number one leadership initiative in any organization today is improved coaching. Coaching empowers employees, empowerment drives engagement, and engagement drives performance. At its core, coaching is about transformation. Leading distributed teams requires transforming how we coach and changing our play calls and playbooks to get things done. As a part of our interview series called “Moving From Command & Control to Coaching & Collaboration; How Leaders and Managers Can Become Better Coaches,” we had the pleasure to interview Ryan Renteria.

Ryan is a CEO coach who helps C-suite executives, founders, and senior investment professionals maximize performance and growth through his firm Stretch Five. His approach derives from two decades of experience in studying and advising leaders as a hedge fund partner choosing CEOs to back, an advisor to Indiana Pacers’ executives, coaches, and players, and as a CEO coach. Ryan earned a BA in economics from Stanford University with awards of highest honors for academic excellence from Stanford’s Latino community.

Thank you for joining us to explore a critical inflection point in how we define leadership. Our readers would like to get to know you better. What was a defining moment that shaped who you are as a leader?

The defining moment that shaped me as a leader came from a very surprising place: a control battle with my son. It happened when he asked, “dad, why don’t you trust me?” I just want what’s best for my kids, like we all do. So, I had been imposing my strong views on what he was eating, when he would do his chores, and how he approached his homework. This micromanaging constantly led to control battles because he felt very little autonomy, ownership of his choices, and trust from his role model. Our relationship became increasingly strained. One day the absurd irony dawned on me. I spend the bulk of my days coaching CEOs, and leadership is a popular topic. Two decades of studying and advising leaders had shown me that trust and empower is a far superior leadership style to command and control. I’d been coaching CEOs to shift even further toward trust and empower leadership actions, and they were working. Yet, in the parenting arena I was ignoring my own counsel and experiencing the same poor results that command-and-control leaders see in the workplace.

So, I nervously started giving my son more autonomy over his choices. He responded to this trust by working even harder and surprising me with smart choices that he knew would make me proud. While this further cemented my belief in the merits of trust and inspire leadership, it stimulated another intriguing question that became a big focus of mine: what other business lessons could we apply more effectively to our personal lives that would make us better parents and partners to our significant others?

John C. Maxwell is credited with saying, “A leader is someone who knows the way, goes the way, and shows the way.” How do you embody that quote as a leader?

I spend most of my days coaching CEOs on how to do exactly what Maxwell is saying. One of the most effective ways to execute on this is to create extensive cultural bylaws for your organization or team. These bylaws convey the team’s specific purpose for existing (why), strategic vision (what), and core strengths and identity to achieve that vision (how). They’re much more effective than traditional values and mission statements for attracting talent, speeding up decisions, and achieving desired outcomes.

Going through the process of creating cultural bylaws forces you to establish a very clear purpose and vision (know the way), gives you specific action steps to model this behavior and demonstrate success (go the way), and gives you a tool for coaching others in your organization to achieve in a similar fashion (show the way).

How do you define the differences between a leader as a manager and a leader as a coach?

A leader as a manager is more dictatorial. They delegate tasks to each individual and are very direct in how they want those tasks completed. They’re laser-focused on metrics around those tasks such as when it needs to be done, how much it should cost, and what KPIs would dictate success. They stay on top of their employees throughout the process to ensure things are moving along as desired. While there are certainly situations where being a manager is needed, such as urgent crises with specific timelines, more situations are better suited to coaching.

A leader as a coach empowers teammates to achieve desired outcomes without dictating exactly how to do it. Coaches ask open-ended questions to gather information, raise awareness, and give their teammates a chance to reflect and arrive at their own answers. They listen empathetically without interrupting, aiming to make their teammates feel fully supported. It’s a more collaborative process where coaches can use their experience to provide teammates with alternative options, but with language that gives their teammates ownership of the decision. The goal is to develop and grow their teammates into strategic thinkers and top-tier performers over the long-term. This style of leadership also significantly boosts employee motivation.

We started our conversation by noting that improved coaching is the number one leadership initiative in any organization today. What are some essential skills and competencies that leaders must have now to be better coaches?

I’d highlight three key skills to becoming a better coach. First, have a voracious curiosity to learn. Ask a lot of open-ended questions, dispassionately seek the best scientific data, and adapt quickly and boldly to that changing evidence. In prioritizing intellectual honesty above all else, you’re coaching your team to overcome the emotional biases that ruin decision-making such as cognitive dissonance and confirmation bias. Second, demonstrate restraint. Avoid rushing to interrupt with your own views, which cuts off idea flow and healthy dialogue. It’s better to pause, listen actively, validate their points, and truly incorporate them into your own decision process. Finally, model the humility and integrity you want to see. If you don’t show vulnerability in owning your mistakes, or do the right thing for your most important constituents, how can you expect that of them?

We’re all familiar with the adage, “You catch more flies with honey than with vinegar.” How are you inspiring — rather than mandating — leaders to invest in upskilling and reskilling?

It’s easier to inspire investing in upskilling and reskilling when you highlight how it serves their interest, delivers a high return on investment, and solves one of their biggest problems. Labor shortages remain a top concern of leaders and could persist for a long time even with the hard landing and increase in layoffs we’ll see in 2023. Lower immigration, increased onshoring, demographic shifts from Baby Boomers retiring and population growth slowing, and the impact of COVID (deaths, long COVID, and early retirees) continue to reduce the availability of labor. Employers must become more creative and willing to invest to overcome these labor shortages, and upskilling/reskilling is just one of many ways. Fortunately, filling positions from within costs substantially less time and money than recruiting externally, so the ROI for upskilling and reskilling can be significant.

Let’s get more specific. How do you coach someone to do their best work? How can leaders coach for peak performance in our current context? What are your “Top 5 Ways That Leaders and Managers Can Be Effective Coaches?”

First, create a culture of two-way trust. This starts with you trusting them, which ultimately earns you their trust. Empower teammates with the autonomy to own projects and stop micromanaging them. Tell them the outcome you desire, entrust them with figuring out how to get there, and be willing to offer support if they want your opinion on tactics to get it done. If they make a mistake that leads to a bad outcome, avoid the urge to criticize or reduce their responsibility. Assume positive intent on their part, show that you still believe in them, and offer to help them make adjustments to their process. When a rising star NBA shooter misses several shots in a row, does a great NBA coach yank him out of the game and scream at him on his way to the bench, or tell him “I believe in you, keep shooting.”

Second, create a safe environment for high candor. Set the tone for meetings by saying we owe it to our employees, customers, and suppliers to have truthful feedback and open debate. Set up meetings specifically dedicated to employees challenging executives with their top concerns. If you interrupt those concerns with definitive statements, you’ll remove their motivation to speak up in the future. Instead, ask open-ended questions that model openness to learning and validate their views so they’ll keep wanting to share them. One example is “That’s a really good point. Can you expand on your perspective so we can learn more? What ideas do you have for attacking this concern?”

Third, model the candor you’re seeking from them. When you have concerning news or thoughts, be transparent in sharing them with the team. If you’ve played a role in contributing to that unfavorable news, admit the mistakes you’ve made, what action steps you’re taking to improve your process, and ask them to hold you accountable real-time and in your 360-degree feedback. This will encourage them to be more open in proactively sharing bad news without the positive spin that hinders swifter and smarter actions. They’ll also be more open about their own mistakes when they don’t fear rash retribution. Importantly, they’ll practice these principles of candor with their own team so it will trickle down throughout the organization.

Fourth, make sure to schedule 1-on-1 coaching sessions at the same day and time every month. Meetings should occur indefinitely since new issues always emerge. Any topic should be fair game, from improving current performance to reaching career aspirations. This is your opportunity to ask open-ended questions such as “what options are you considering, and what are the pros & cons of those?” You can listen empathetically and offer counsel while allowing them to maintain ownership of the decision. One example would be “In my experience, XYZ may prove helpful for you to consider.” Lastly, provide whatever support that could help them. Ask: “can I invest in a resource, outsource a portion to another, or do anything else to help with your issue?”

We’ll save the best for last: prioritize their mental health. Care deeply about them as individuals including learning about their personal dreams, goals, and challenges, and how you might be able to support them. Recognize their achievements with highly specific compliments that surprise and delight them. Thank them with the care of handwritten thank you notes and gifts customized to what they really like. If you’re the CEO, there are many creative, non-traditional mental health benefits you can provide and expand. If you’re not the CEO, you can ensure your teammates are fully aware of all the mental health benefits and how you take advantage of those, which models and normalizes it.

We’re leading and coaching in increasingly diverse organizations. And one aspect of workforce diversity on the rise is generational diversity. What advice would you offer about how to effectively coach a multi-generational workforce? And how do you activate the collective potential of a multi-generational workforce?

Interestingly, research shows the best traits for leading younger generations are quite similar to the best traits for leading any generation! Show a curiosity to learn, make swift decisions and adapt boldly, display humility in admitting mistakes, ensure integrity in prioritizing your most important constituents, and communicate clearly and directly. However, there are a few special priorities from younger generations to appreciate and reflect in your leadership to activate the collective potential of a multi-generational workforce. Work-life balance and flexible work arrangements can be as important as compensation in motivating many from younger generations. They want leaders who take interest in their careers by laying out a clear path for promotion, mentoring them, and advocating for them along the way. Working for a company with similar values to theirs and feeling like they’re making a difference through their work is of utmost importance. Lastly, they much prefer trust and empower leadership, and being spoken to in a calm and empathetic way, to the more forceful command and control environments of the past.

You’re referring to emotional intelligence, in a sense. What are two steps every leader can take to demonstrate a higher level of emotional intelligence?

The first major step is to study and master the emotional and cognitive biases that often ruin our own decision-making. Study mistakes you’ve made in the past from biases such as cognitive dissonance, confirmation bias, recency bias, and the illusion of control. The decisions you make highly impact your team so they’re counting on you to make good ones, and to help them improve their own decision-making process. The second step is to master the skills of empathetic listening and common ground so that you understand and relate to your teammates’ feelings and help them recover from mistakes so they return to peak mental performance quickly.

Words matter. And we’re collectively creating a new leadership language right now. What are the most important words for leaders to use now?

Here are 5 of my favorite sets of words leaders can use: 1) “I believe in you and your process,” 2) “I could be wrong here, so please tell me what you think,” 3) “How can I best support you on this?”, 4) “I have a lot of respect for your opinion, so let me show you how it influenced my decision process,” 5) “I see zero limit or ceiling to your potential growth and impact.”

I keep inspiring quotes on my desk. What’s your favorite “Life Lesson Quote,” and why does it mean so much to you?

“Winning isn’t anything you own. You just rent it, and then you have to pay the rent daily” ― Stan Moss. No matter how successful you’ve been in your professional or personal endeavors, you cannot become complacent or rest on your laurels. The best leaders in the world are constantly striving to find anything that can help them foster improved growth and performance.

Our readers often like to continue the conversation. What’s the best way for readers to connect with you and to stay current on what you’re discovering?

Readers can follow me on LinkedIn (

Thank you for a meaningful conversation. We wish you continued success with your mission.