Radicle Growth: Transform into an Unstoppable Leader through Mastering the Art of Questions

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Copyright © 2025 Dave Reynolds

All rights reserved.

First Edition

ISBN: 978-1-5445-4820-3

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This book is dedicated to my children, Oliver and Cooper, as a reminder that anything is possible.

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Contents

Acknowledgment

Introduction: Finding the Right Answer

1. The Difference between Managing and Coaching

2. Leadership Challenges

3. What Does the Current Conversation Look Like?

4. Discovery

5. Awareness

6. Focus and Commitment

7. Follow-Up

8. Systematization

9. Leading Up, Across, and Down

10. Bringing It All Together

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Acknowledgment

I’d like to thank Pablo, my mentor for over ten years who showed me the value of asking the right questions to find the right answers.

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Introduction

Finding the Right Answer

Bosses Don’t Need the Answers If They Know the Right Questions

You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions.

—Naguib Mahfouz

One of the first things we do in our workshops for newly promoted managers is to ask them to think of the toughest boss they have ever had. Think of the person who pushed you the most. They had high standards and expected you to meet them. They were never satisfied with simple or vague answers. When you asked them questions, they responded with their own questions. They forced you out of your comfort zone.

Six months later, after they complete our training, we ask these managers to think about the best boss they ever had. Who did you learn the most from? Who stretched you the most? Who paid attention to you and seemed to care the most about your improvement? Who spurred you to improve while instilling confidence that you would improve? Who saw something in you that you didn’t see in yourself and elevated you to that level by pushing you harder to get there? Who invested in you because they knew it was possible—even if you didn’t think it was.

It doesn’t take them long to identify that person. Virtually every one of our participants admits the toughest boss was also the best boss.

This realization comes to them because, over the last twenty-four weeks, they’ve learned that the best bosses are not the people who have the most experience or have the right answers. They aren’t the leaders who shower them with praise and congratulate them for every accomplishment, large or small. Instead, these bosses were great because they demanded more of their people. There was friction, sure, but that friction is what sparked the fire, the inspiration. These bosses supported them yet held them accountable.

These bosses invited their people to not just identify problems but to find solutions to those problems. These bosses didn’t have easy answers but instead compelled their team members to find answers and, through that process, grow and improve. These bosses didn’t tell you what you wanted to hear. They told you what you needed to hear. This didn’t always make you feel good, but it helped you grow and learn. These bosses used a care-and-candor approach; they cared enough about you to be direct with you, and in that way, you experienced transformational growth. They pushed you from the nest and told you to build your wings on the way down. It was tough sometimes, but ultimately, these were the bosses who made their team members feel like they were collaborating with their supervisor, co-creating and taking ownership in solving problems and making sure their solutions truly worked.

Asking the Right Questions

The central goal of our Radicle Growth coaching program is to help leaders—whether they were recently promoted or have been in the role for some time—acquire the skills they need to become great coaches. In our experience, becoming a great boss is not about always having the right answers. It’s about asking the right questions to get the best answers. Radicle Growth teaches leaders how to use questions to coach their team members to their own answers.

Most team members already have a solution in mind but will go to the boss’s office and ask for the answer anyway. Sometimes, they are just looking for an easy route. Sometimes, they just want confirmation. In a traditional, hierarchical environment, the boss gives them an answer. It’s a simple and quick one-way transaction.

And it’s also highly unproductive. The next day, the team member returns with another question, then another. Over time, the boss is doing little but solving problems for others. During training, we ask audiences all the time, How often does somebody ask you for a solution and you’re busy so you just quickly give them the answer? Everyone’s hands fly up. Okay, how many of you have found they keep coming back with the same problem, and you provide the same solution? Again, a forest of raised hands.

The whole idea behind Radicle Growth is to turn that transactional approach into a transformational one by using a two-way conversation that changes how leaders connect. The team member is no longer merely carrying out orders but instead is working with the manager on a solution. The result is that the team member is more committed because they are addressing a problem they helped solve, which increases their confidence and productivity. As their coach, you help your team members think more independently and become less dependent on you. Team members are challenged to grow. Better solutions emerge. Productivity soars. Honesty, trust, and continuous improvement become the cornerstones of a thriving workplace.

When you have a strong coaching culture like this, you get more from your teams and people. Coaching takes new knowledge and turns it into an implementation system with more accountability and urgency. One study found that training alone increases productivity by about 22 percent, but when you adopt a coaching mentality—where employees are taught to think more for themselves and work with managers on solutions—productivity increases by a staggering 88 percent.1 That 22 percent increase is a blip that disappears quickly from your productivity curve, but the 88 percent comes when you take that training and extend it out—by systematizing it and standardizing it. It becomes embedded in your mindset and your operation. Knowledge alone is not power, but the adoption and application of that knowledge certainly is. The reason that coaching is four times stronger than training is that a coach gets you to use the information you learn. Coaching takes something you know or learned and puts it into a system for your work and life. Blips of productivity are great but that increased productivity is not sustainable unless you can systematize it. Solutions are better and are effectively employed. Workers take ownership and are more accountable. It’s much like having a personal trainer. If you go to the gym alone, you might work out at 60 percent intensity. But if you go to the gym with your trainer, you’re likely to work at 90 percent intensity.

We call it Radicle Growth because, in botany, the radicle is the first part of a seedling to emerge from the seed during the process of germination. It is the embryonic root of the plant that grows down into the soil and eventually enables the seed to sprout above the earth. In the workplace—but also in life and relationships—Radicle Growth begins with purposeful questions from a coach to a coachee.

What You’ll Learn

This book is written for leaders who want to hone their coaching skills and better lead their teams to new heights. Some of you might be struggling with the unceasing questions that are part of management. You might feel caught in the middle, juggling the expectations of your own bosses while patiently nurturing your team. You may even think at times of returning to those good old days when you didn’t have to manage people at all!

This book will provide some fresh strategies for you. It covers the core principles we teach in our Radicle Growth coaching program, and while it will give you many ideas about how to improve as a coach and leader, it may also be the incentive you need to enroll in our coaching program and earn certification in the techniques we use.

In our training, we ask people whether they would choose a young plant to put in the ground or a seed they could bury and nurture into a young plant. Many choose a plant because they can see whether it is struggling and needs water or fertilizer. Likewise, they can be sure that it’s healthy and growing. On the other hand, when you plant a seed, its growth takes place underground. You can’t see it push out the radicle; you can’t see the root system spreading out. But eventually, the shoot pushes through the soil, and you have a strong healthy plant.

This is an analogy for coaching. If you want to transformatively change your behavior, you have to believe in the process. It will take some time to see the results—about ninety days to see the result of a new behavior. So, just as you must believe in the radicle process or growth—that foundational growth is occurring beneath the surface—you must commit to systematizing your coaching system. Only then will you see long-term growth.

Let’s define what we mean by coach and coachee. In many cases, the coach is the boss or a supervisor, and the coachee is an employee. Sometimes the coach is a peer and not a direct supervisor. My first coach—Pablo, the man to whom I’ve dedicated this book—was initially my direct supervisor’s boss. He’s had such a huge impact on my life, not only just teaching me how to ask the right questions, but forcing me into deep self-reflection by asking the right questions. But he also became a model and a mentor and someone I looked up to. A coach is also a motivator who’s not only giving coachees the recognition that they’re probably striving for but also in a lot of cases pushing them and challenging them to get the best of themselves. In sports, the best coaches in the world are not just there patting their players’ backs but pushing them to go as far as they possibly can.

The best version of a coach is someone who believes you can achieve more—possibly more than their coachees believe they can achieve. They see something in others that they might not even see in themselves. The coaching process is about how you transform the coachee into what the coach can see in them. It’s a transformative process, and being a coach is a big responsibility and investment. What’s more, having the opportunity to be a coachee for a great coach is a big opportunity. When certain players get selected by certain teams, they are excited because they get to work with that team’s particular coach.

Phil Jackson is a great example. When you got selected by the Chicago Bulls, it wasn’t about getting selected by the Chicago Bulls, it was about getting selected by Phil Jackson. You were going to get a chance to work with Phil Jackson. Good coaches can transform another person’s life. I’ve coached hundreds if not thousands of people, and I know that I’ve had a lasting effect because I’ve talked to them years later and saw that the things we talked about stuck with them.

This shows the transformation a coach can create. The first question we ask when we teach Radicle Growth is, Who benefits from you taking this course and becoming a better coach? The answer is all the people you’re going to work with over the next X number of years in your career. If you apply these skills as a good coach, think about how many lives you’re going to impact, helping people become better husbands, wives, or partners and/or become better bosses and leaders—potentially becoming CEOs.

A coachee is anyone who is receiving the coaching. They are receiving information, incorporating it, acting on it, and exhibiting the new behavior they’ve learned. In coaching, you create a relationship and invest in someone with the goal of helping them improve. You hold them accountable for following through on their commitment to the process and to the relationship. Your coaching is designed to convince the coachee to change how they think and act.

Being a coach is much like being a father. A coach must take on that level of accountability and responsibility. Being a coach is not a check-the-box job. You have to realize the responsibility and power that comes from being an impactful coach. By learning to be a great coach, you are taking on a superpower that’s going to help you accelerate your career because you’ve got people who support you.

Here’s an example. I just met with a huge car dealership owner who owns seventy or eighty dealerships. He said that if he buys a dealership in the US and the general manager leaves, almost everybody leaves with them. The GM has so much influence that they can almost