Mastering The Art Of Asking Questions With Dave Reynolds

What if the secret to unstoppable leadership lies in mastering the art of questions? In this episode of Career Sessions, Career Lessons, host JR Lowry sits down with Dave Reynolds, serial entrepreneur, founder of The Rumin8 Group, and author of Radicle Growth: Transform into an Unstoppable Leader Through Mastering the Art of Questions. Dave shares how asking the right questions—rather than giving answers—empowers individuals, strengthens organizations, and drives sustainable growth. From transforming team performance through strategic coaching to navigating the growing demand for fractional leadership, Dave reveals how leaders can cultivate self-awareness, foster accountability, and prepare for the opportunities of tomorrow.

If you’re ready to rethink leadership, embrace the power of inquiry, and discover what it truly takes to build a resilient, thriving organization, this conversation is for you. Tune in now and start asking the questions that will shape your future.

Check out the full series of “Career Sessions, Career Lessons” podcasts. Visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/dave-reynolds/.

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Mastering The Art Of Asking Questions With Dave Reynolds

Author Of Radicle Growth: A Guidebook To Growing A Vibrant Life

My guest is Dave Reynolds. Dave is a serial entrepreneur who has launched and developed a variety of new products and services for nearly two decades. In this episode, we’re going to be talking about his company the Rumin8 Group, his new book, Radicle Growth: Transform into an Unstoppable Leader through Mastering the Art of Questions and a bit about Dave’s career journey as well. Let’s get to it.

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Dave, welcome. Thank you for joining me on the show. I appreciate having you on. You’re the Founder and CEO of the Rumin8 Group. Tell us about your business.

Dave’s Career Journey And The Founding Of The Rumin8 Group

We started Ruminate Group many years ago and we had jumped into a lot of the executive coaching scene at that time and branched out through other services like succession planning and performance management. The Rumin8 Group is a growth consultancy and we’ve been able to be the industry agnostic. We’ve had fun to get into areas like architecture, engineering, fintech to biotech as well.

You’re up in Halifax, Nova Scotia as we talked about right before we started. Did you do most of your work in that part of Canada and Canada more broadly than that?

We got clients all over the world, but predominantly we started in Eastern Canada. We’ve been servicing clients nationally throughout Canada and several throughout to the States as well.

What was it in particular prompted to do to start the company? Was it the sense that coaching was taking off back then or was it something else?

I was predominantly always a serial entrepreneur, but I took a crack in telecommunications at the corporate life and amazing experience. A lot of good leadership development journeys. The thing that I kept picking up was the coaching side performance management. That became an area where I was helping redesign sales teams and elevate them into different levels of performance. It got to a point where I was like, I feel like I want to broaden my horizons and start looking at other fields.

I happen to have a friend of mine in one of the NHL games because we had the box. I was asking his wife who had a big real estate company, how she coached teams and what was some of the KPI she measured. She almost got the bar and she’s like, “Can you just come in and consult for me? I would rather grow the business then come, manage and coach the teams.” That was my first jump into consulting. It was so yes and figure it out.

What are the things you’re doing now for your client base?

To me, expanding beyond the executive coaching realm. We still do that as a real main focus for service but we’ve gotten deep into succession planning as we see that’s topic that people have identified as important. We don’t always execute on, so we’ve worked a lot in forestry, banking, and some of the other financial sectors. We also focus a lot on performance management and customized learning and development programs, where we can be a little bit of a fractional learning program for organizations as they’re growing and scaling.

There’s going to be a growing need for that. I feel like more companies are offloading their full-time staff and bringing people in on a contract basis when they want to execute some learning and development program rather than having somebody around full-time.

I agree, and they’re starting to see more people looking at what investments do we need to make in our teams to get them to that next level. They’re looking outside the typical realms. They’re getting into emotional intelligence, strategic communication, and negotiation. It’s exciting because that’s the next step to growing a developing.

It’s interesting that you bring up succession. To me, it’s a topic. I have an article in my head that, at some point, I want to write on this topic because it’s the ultimate asset test of succession. Whether you do replace the person who’s supposedly the successor. Often, people fill in a name and say, “Bob’s going to be the successor for Mary,” Mary leaves and Bob doesn’t get the job. It’s like, “Why was Bob’s name on the chart in the first place?”

It’s funny to say that. I remember being in telecommunications. This is where I first started falling in-love with succession planning. I had an amazing boss named Pablo, and I remember him setting up success criteria. If you do all these things, you have the chance to move into the next leadership role. I was always like, “How do I move up through the organization?”

I remember one day, I had everything checked off that I needed to move up. He was visiting from Ontario, and I said, “I’ve got all these pieces done.” It seems like an opportunity for me to move up. We’re having that conversation and he just goes, “You’re right.” For me, it was just too easy. The one thing he said to change, he goes, “Perfect. Who’s your replacement?”

It was easy for me to just come up with a name and his response was perfect. “Are they going to be able to take over that same level of performance that you established within your division?” My response was, “They’ll catch on.” You know that they’re not. Part of what we developed in succession was a program called Train your Replacement, which speaks to what you’re mentioning. It’s like, people moving up also have to mentor somebody in, so knowledge transfer and simulation. It doesn’t get done in organizations enough, but it’s critical to sustainability and scaling.

This is important. You’re in a growing firm. You’re constantly moving people up and bringing people to your level at. It’s harder when you’re not in a growing firm. You’ve got a bunch of people who are ready. and there’s not a role for them.

That’s a great point. It’s interesting. When we draw like, it’s called Succession Exits. You draw two lines that said, “For succession to happen, you need these two things intersect.” One is opportunity and one is preparation. A lot of times, you see organizations have opportunities but people aren’t prepared. There’s that level of frustration, but what we control is preparation. Not so much the opportunities in a lot of cases. We try and get organizations to lean into how do we prepare people for the future. when opportunities open up, it’s easier to put people in those roles.

Coming back to your firm, what’s the shape and size? How many of you are there full-time? You have a network of people you draw into.

It’s an amazing question. We’re a small but mighty firm. We only have a couple people inside of the organization but we leverage that fractional support. When we get into strategic plan like succession planning, we’ll tap into certain resources that we know specialize in those areas that we need to execute. For us, that’s been great because it allowed us to be agile and adaptive to the projects that are coming at us at all levels.

The world is moving toward a project economy, where people just come and go into a mix things. Call it whatever you want, gig economy or whatever. It feels like there’s mechanisms out there to connect, buyers, sellers, and services in ways that didn’t exists in the past, which is why you have more of fractional stuff going on and you did certainly at the beginning of my business career.

We see so much now that you didn’t see many years ago at the fractal CFOs, CROs, or CMOs. Especially as you’re going up to medium-sized organization. You don’t need that full roll, but you need that specialized support.

It’s great to see organizations leaning into that. What are your goals for your firm over the next few years?

We’re North American focus predominantly now. We’re expanding more deeply in the United States through of more our coaching programs, but more into succession planning. There’s a such a high interest, where when we test into organizations around how many people are retiring, what is the legacy look like of leadership continuity. We’re, expanding deeper in the United States for that and Western Canada, because more organizations are thinking about this because it’s not something that can happen overnight. We need to think of things in a proactive state. Our expansion plan are throughout North America.

The Concept Of Radicle Growth And Its Meaning

Let’s talk about your book, Radicle Growth: Transform into an Unstoppable Leader through Mastering the Art of Questions. A little bit of a tongue twister for me there, but I learned a new word, as I mentioned to you, before we started. I had not seen that use of the word radical with an LE as opposed AL. Help us understand why that word has meaning in the way that you used it as the book title?

I had thrown the book up the other day and I’d gotten a lot of messages from close friends. They reach out to me and wanted to save you from some embarrassment. I said, “This is happened from day one since we started creating this as a title.” Radicale is a term that they haven’t bought me where it’s the first stages of seed takes when it breaks through the shell.

Where this name originated from, is we used to take teams through performance management and leadership development. We used to draw a line down the board and say, “If you could have a plan, we could have a seed. Which is the one you typically invest in?” A lot of people don’t always go, “The plants because I can see when it’s dying and I’m going to water it.”

It’s interesting when we start getting to the seed analogy. I said, “Where does the seed grow?” A lot of people are like, “It grows under the surface.” It’s going to establish roots system. The reason why I love radicale is the fact that a lot of leaders plant seeds consistently, but they give up on them because they don’t see that immediate result at service level. In reality, the growth is happening under the surface. We like the idea of a radicale growth concept. If we’re going to plant the seed of a new idea, it’s about committing to and persevering. You’re giving it the discipline it needs to breakthrough the surface and show long-term results.

When I saw the title and looked it up to understand it better, I thought what a great way of describing it. It has meaning of the work that you’re doing and what you’re trying to describe in terms of growth. It also catches your eye because you ‘re like, “It’s spelled wrong.” You look at the book more carefully and at least it draws the person’s eye to the tide, which I’m sure was intentional.

We almost got fearful that we had to explain it on the cover but I said, “It’s something that they’ve get curious about,” and a lot of people have. It’s a good thing in some ways because platforms like this where we get a chance to explain it. I appreciate you asking.

You start the book with a quote, “You can tell other man is clever by his answers. You can tell other man is wise by his questions.” You’ve anchored your book around the art of questions. Why do you believe that that’s so important to success?

This question for me is something that goes back to my acknowledgment in the book to a leader that I had named Pablo. He was leader that changed my paradigm on the way I thought about leadership. An area that I thought about my personal learning growth is that he used to ask me this hard questions and in reality, it was easier for me to go, “I don’t know the answer.” You wait for somebody to give you the answer.

He would sit there in silence until you came up with something. He forced me to be vulnerable, be transparent, and come to those solutions by myself. He was always good at reframing, digging deeper, and asking more questions to get need to conceptualize my ideas. He showed me how to use questions to lead, influence, and grow the leaders around him. I was able to take that same concept and use that internally on my teams.

I could immediately see the difference between telling somebody what to do versus asking them what they should do. It empowered people to hold accountability and ownership by being ask versus told. We’ve been able to pull this into the book and share those concepts. It’s like an art and science from coaching and leveraging questions as your path forward.

Asking Questions: The difference between telling somebody what to do and asking them what they should do is that it empowers people to take accountability and ownership by being asked rather than told.

I have another article that I have thought about at times like forms of high praise. One of the forms of high praise that I’ve always felt strongly about is when somebody says, “That person asks great questions.”

That’s an amazing praise if you have that, because it shows your equipt to think.

To your point, what Pablo is doing with you, he’s drawing you out. He’s forcing you to think more deeply, to not just say I don’t know, and to not just look to him for the answer. He’s putting the burden on you and come up with your view. The best people do sit there in silence and they wait for you to answer, but it’s hard.

There’s an old saying. I think it was from Susan Scott. She wrote a book Fierce Conversations. She had a quote that said, “Let’s silence solve the puzzle.” I feel like that is such a skill that a lot of people should master. Sometimes think of it as, when we look at questions and we think about, where is it a parent organization?

We usually ask clients that work with and say, “We looked at your organization. How many people in the organization would you say are dependent or independent?” It’s interesting. We start getting the Xs and circles by them. I would say, in a lot of cases, when we break it down, the people that are dependent is because the leaders giving them the answers versus forcing the questions to get them to think independently. That was that area where questions became the keys that help people go from dependent to independent and the way that they thought, both strategically and elevated as a leader as well.

You mentioned that you came up in sales. There are a lot of sales examples in the book. Clearly, what’s here could be applied more broadly.

Big time. I would say that as we started the conversation, I would say Rumin8 is industry agnostic. Sometimes, it will come into our organization and the less we know, the more we can help because it forces us to be a little bit more Socratic and think about the way that we asked questions. We typically learn a lot from our customers.

One of our largest clients starting off was one of the biggest law firms in Canada. We started working with associates to get to partner. Some of them would have been new business development concepts. In reality, it was around process development and a lot of different areas where we could leverage questions to get them to self-realize where the answers were. It applies to a lot of different areas beyond sales. I had so much experience in sales. It was an easier to get these awesome easy problems.

You use a language of coaching/coachee in the book even though you aren’t necessarily talking about the specific job of being a professional coach. Clearly, you’re linking that much more into the role that a manager needs to play as a coach.

Exactly. We started thinking about how we link that relationship together with the leader that is connecting with the employee or the staff member. We didn’t want to say it had to be a staff member or subordinate because in part of the book, we talk about leading up, across and down. Being a coachee doesn’t mean it’s an inferior role. It’s just depending on how you’re creating that conversation. We want to be able to name the coach and coachee concept. We thought it was great because it shows that that relationship between those two parties that are connecting.

The Five-Part Radical Growth Framework

Let’s get to the heart of the book, the five parts to your radical growth framework. Can you give us a quick overview and maybe description on each of them and we’ll dive in a little more deeply.

We’ve got a couple of concepts that we share throughout the book. It’s the first part of the actual coaching process within Radicale Growth, which is discovery. I would always say the best way we talk about discovery is when we connect with each client. It’s like dumping out a puzzle. Half of those pieces aren’t flipped over. Part of discovery is about flipping those pieces over, so leveraging open-ended questions.

The next stage that we would move into would be self-awareness. It has self-aware. The people that the coaches working with are the challenges and the opportunities. We’ve seen so many moments where you can see a light switch click on and they become more self-aware of the opportunity or the gap that they need to address.

That leads into the next stage which is focus. With technology, it’s so easy to lose focus and focus on ten different things at once. We talk in the book about how we dial in on those one to two things that are the most important. Similar like the law of diminishing return. What we do as an important part of it because we leverage questions, is we get to the commitment phase where we say, “How do we get the coachee to own the next step?”

Every time that we take people through one of those coaching scenarios, it’s a matter of how do we get them to commit to something that will be connecting on? That follow-up stuff, which is our last one, is what we start the next session with. We always say when we’re coaching is, each session should be connected to the next one. The way that we connect them is that the follow-up is where we start the next session. It’s like chain link. What helps link us together is that relationship of accountability and ownership. We can work with organizations that usually take this much time to get something done and get it done in a short amount of time because being get that accelerated commitment level.

Questions are a key part of that discovery phase. You talk about five different types of question. I have never seen these list this way. I like that open-ended and close -ended. Most people probably know the difference between the those two. You also have probing, mirror and paraphrasing. Maybe you can talk a little bit about that mirror and paraphrase that might be a bit different that the once people would normally think about when they think about types of questions.

I’ll give you a cool example with the mirror one. This is one that I would say gets referenced in other books as well, but we’ve mastered a lot with the clients who work with. We had a client that was struggling on getting a project manager engaged in the conversation and delaying and pushing things off. Mirroring is about how do you structure a sentence that they respond to and you give the last three words?

The way it will work is where have you been struggling with team communication? Let me rephrase this. She asked in the conversation, like, “Tell me a little bit about how the project’s going.” They would say, “The project is going well.” The mirror is, it’s going well. What you’re doing is you’re mirroring the last part, then this is where what we talked about silence. She let seventeen seconds go by because they said, “Put a timer down and don’t be the first person to say anything.”

She just came back because it felt like an hour. The person leans back and said, “We had a couple of delays.” “You’ve had a couple delays?” The same thing here, and she said another fourteen seconds went by, then went back. “We rented this resource issue,” and the same thing. “You’ve had a resource issue?” She said she must have mirrored about 8 or 9 different statements. By the end of it, everything was on the table because it forces a deeper conversation. I like leaning into that. Not in just our one-on-one, but teaching that concept out to clients. It seemed so simple, but it’s something that transforms the conversation.

The Power Of Silence In Communication

It’s a way to set up the silence just listening to the way you described it. You talked about having one of your clients hold a stopwatch under his desk time to time the silence. You’re making it clear that you expect to hear something more, then you’re leaving dead air. They’re going to feel it eventually.

You put a good point. We get back that silence piece. I feel silence is very difficult for people to master, even though it seems so simple. Whether you’re in person, or in a boardroom or even online. Your body language, as you say, you’re waiting for a response but you don’t want to be that first person to say something. If you do, you’re guiding them to where you want them to go. She transformed that relationship just by that strategy alone.

I would say paraphrasing is a good way. It’s almost like a different way of thinking about recapping. In statements, what we would say is like, “What I’m hearing is that improving communication between departments is a top party. Is that right?” You’re taking something that’s been said by question you’ve asked and paraphrasing that back. It’s good because you leverage a confirming statement then because they’re saying, “Exactly.” They might expand or build on that as well.

Asking Questions: When you take something that’s been said, turn it into a question, and paraphrase it back, you leverage a confirming statement, prompting people to say, ‘Yes, exactly,’ which may lead them to expand or build on it further.

Related to the whole topic of asking these questions is the importance and you bring this up in the discovery part of the book as well around not shying away from the deeper difficult conversations. Why do people not dive into those things? Why do they not dive into those conversations when they do?

I’ve always wondered the same thing. It gets to the idea that we’re we do live, in a lot of cases, that are very surface level area. It’s easy to accept the first answer because it sounds okay. It’s like the idea, good is the enemy of great. We accept that easy answer, even though it’s so much easier to get deeper into it. I’m going to give you a good example. We work with a lot of sales organizations. If you walk on the floor and say, “How our sales going?” “Sales are good.” They’ll say, “Perfect.” They’ll keep going.

I remember stopping with one of the owners and I said, “Sales are good.” He said, “Perfect. Walk me through. Where are you guys at?” They said, “We’re X, Y, and Z amount of sales.” He said, “Perfect. What’s been your goal for the month?” They shared the goal. We always do trends, so I said, “What are you trending?” They were trending on their goal. I said, “Let’s go back to the original question. Sales are good?” They said, “It’s a challenge or struggling in some of these areas.” I said, “We accept good as that response that things are good. It’s about how can we peel back the layers to understand what is good mean to you.”

It’s also too create a relationship between those leaders and the team members as well that they are going to dig deeper. They’re going to look for the actual results. It doesn’t power the relationship. People like to be held accountable. The owner would always do that saying, when he heard good, dig deeper and keep going.

It is easy just to brush past it. It’s like, “How are you doing.” “Okay,” and that’s the end of the conversation. Often, there’s things that aren’t said there, but there’s a sense that they’re there. They’re just beneath the surface.

I would say that I probably gotten 4 or 5 questions in on surface level, real conversation. That’s why I lean into the idea of how do we dig deeper and so, we get to something that’s like a true statement. It’s almost like clarifying statements and understanding.

Expanding Self-Awareness

Getting into awareness, the second part of it. One of the things I took away from this part of the book is that it’s not just about having an awareness of the situation but also having an awareness of self. Clearly, if you’re in a coaching construct, you are trying to get people to have an awareness of self but I would imagine what you’re trying to get them to do is to have that awareness of self and when they’re out doing their thing.

I agree. I would say one of the topics we jump into when we do workshops is typically navigating difficult conversations. This is an area that we talk about the book like the charity window. They were so used to looking at that singular point of view. We’re not always like reflecting on some of those impacts of those things. Commonly and a simple example is, a lot of people say, “These people aren’t responding to my messages or I’m not getting the reaction we’re looking for.”

Even something as simple as, how do you think they’re receiving the message? You can tell that they haven’t thought about it. They’re more worried that they’re not getting the response they’re looking for but they’re not realizing that there’s two sides of the equation. The person that’s sending the message and the person that’s decoding it. What we’re trying to do with self-awareness is also to make people more self-aware. People that are around them are the people that they’re interacting with, which helps them change the way that they communicate and interact. It could be even self-aware around sales or process development. It’s about trying to get them to own the current reality.

It’s the idea of having self-awareness. I’m reading another book on organizational politics. The book is unbelievable in terms of the depth that goes into on all of these different aspects of politics. It makes you realize how much we do things that are self-sabotaging from an organizational politics standpoint in our lives.

It’s interesting around self-awareness where you’re probably dive in the most. It’s trying to get people to understand, was that an emotional decision or a logical decision? It’s almost one of those moments where they’re going, “Oh.” You can see that it hits differently because they’re like, “That was an emotional decision for sure.” It’s like, “How could we have made it logical?” They go, “I should taken that five second rule.” They took a step back.

Winning The Day: Prioritizing High-Impact Behaviors For Long-Term Success

Focus is the next part. It’s a distracted world. How do you practice focus? How do you make sure you’re staying focused on what you do?

It’s like I’ll saying the doctors are the worse patient. We always try and I’m always trying to hold myself accountable and team members accountable. Also, to work with clients, it’s always being aware of like the parade of principal like, 20% of what you do, gives you 80% results. We always ask what behavior do you do on a daily or weekly basis that gives you the highest level of return? I’m always keeping that in front of me.

I always consistently compounding that behavior. That’s what I try to do consistently on a daily basis because we use a mantra and a tactic called winning the day. We’re trying to dial in those behaviors into winning the day. They could be in part personal and professional and taking those elements and building those in. It becomes part of your foundation but like anybody, it’s so easy to get distracted with 4 or 5 emails and instant messaging.

What I try and do with some of those areas where I want to focus is work in sprints. I try and take my notifications down or put myself into an environment where I can focus because in a lot of cases, people are very stop-start, stop-start. They’re never getting the progress they’re looking for. When I try and create the right environment for clients and myself to focus, it’s a matter of asking the questions of, what do you find is your biggest distraction? Where are you doing the work where you feel most focused? Trying to get you to understand how can you focus and where should you focus. Make sure that you’re getting the return on this focus items that you need to.

Is that what you mean by winning the day, making sure that when the day is done you’ve done the most important thing that you needed to get done that day?

Very much so, if you self-reflective at the end of the day. I know I’ve been through a day before you feel like exhausted and you felt like you did everything back-to-back. Somebody asked you, “What did you do.” You can’t pinpoint anything you did that progressed the day. It’s a matter of going through and saying, “I did these key pieces consistently. That, for me, was what winning the day look like.”

For other teams, it’s something quantitatively and something qualitative potentially. It’s about winning the day consistently. The reason why we use that concept is, when the year by doing it in the last quarter, it’s about adding up winning the day to win the month, the quarter, or the year. We’re trying to reverse engineer those micro wins into that macro result.

It’s easy to fill your time with things that are comfortable or easy or maybe what feels like the right thing to do to appease somebody. You end up going home at the end of the day going, “I was busy, but I don’t feel like I got anything important done.” To me, that’s losing the day. You can have that happen every now and then but some days, it kicks your tail. If you have enough of those days, you’re loosing the here.

I agree. It’s like the opposite of the parade of the principal we shared in the book. A lot of times, people get stuck doing 80% that gives them 20% because they’re always putting out fires. They’re always in a reactive mode. They’re never dialing into a proactive area, so I had 100% agree.

Asking Questions: A lot of times, people get stuck spending 80% of their time on tasks that yield only 20% of the results because they’re always putting out fires, stuck in reactive mode, and never really dialing into a proactive area.

Commitment: Turning Words into Action

We wanted the commitment. It’s where you’re turning words into action. It’s important part of the process. What advice do you give the people that you work with on how to translate intent into execution?

This is something that I learned early on a leadership when I was in telecommunications. It was good and felt great to have an awesome conversation. I had a good coaching session, then we’d walk away. We come back and say, “Why isn’t anything changed? I thought we had a good conversation.” There was never a commitment. It’s almost like a loose end or a loose string. I found once we finished each session by asking the question. Based on what we’ve gone through, what’s that one or two things that you feel you need to do before we meet again?

Something as simple as that is easy for somebody to say, “I need to do this and this.” We’ll look for some clarifying questions and making sure that they’re elevating their execution and putting that into place. What we do is we get the time associated with it and we set the next cycle to say, “Here’s when the fall of going to happen.” The key is, it’s not me telling them what they need to do. It’s them telling me what they need to do. What it is, they’re the one that’s owning the solution. For me, that was transformative on getting people to take words into action and get the progress that they were looking for.

Deliberate Practice: Pushing Beyond Comfort for Meaningful Growth

I don’t know remember if you used these words exactly, but you talked about this idea of deliberate practice, versus practicing maybe a little less formally or with less structure. You used Tiger Woods as an example. You walk out of that session and you commit to something between practicing it and deliberately practicing what you’ve committed to.

I think we used the word intentional in the book, It’s like leaning into some of that intentionality. A lot of times, people will avoid certain commitments because it’s not a natural change for them. It’s a matter of going, how do you take some of those unnatural practices and put the intentional next steps to them? Sometimes, it’s about them getting outside of their comfort zone. Where we use the Tiger Woods examples, is when Tiger Woods change its swing, which for a guy that had mastered golf at that point. That said, “I can do it better.”

That, for him, would have been outside of his comfort zone, but he knew that he was going to lose a couple rounds to win more rounds long-term. We try to get our clients and customers, the people we work with, in that mindset to find the best practice, even if it’s not just inside their comfort zone. Anything that’s outside of that comfort zone is going to be the growth zone. That’s an area where we get people to think differently about how they want to grow. Once they break through it, they start seeing that as an opportunity to grow. They need to get outside of the comfort zone and continue to push himself to new levels.

I had a boss when I was working for Fidelity. A woman named Laura Cronin. She used to love to talk about Tiger Woods’s golf swing. She would talk about out, to your point, best player in the world. He certainly didn’t need to change anything, but every now and then, he would reinvent his swing. He decided he was doing a bad thing well. You go through a stage of doing the right thing badly, which is your point about loosing a few rounds or a few tournaments on the way to doing something even better well.

He’d go through that cycle periodically and that’s the part that gets hard. When you’re in this period of you’ve committed to do something and it’s not going great at the beginning because it’s uncomfortable. It’s not the way you’re used to doing it and getting yourself through that, doing the right thing badly stage is where a lot of people get stuck.

I couldn’t agree more. It’s because it’s like the whole idea of like Robert. With every decision, you can have that why on the road. It’s like, “I can choose the path of least resistance and do what I’ve done.” If you’re happy with the result, you might want to replicate that. I know when I look at the growth that we’ve had with clients and I said, “If you went back to that version who you were and you looked at who you are now. Would you even recognize yourself? A lot of them are saying, “No,” because they’re paradigms change because they done something differently to get themselves out of the old way that they’re thinking about the easy way. I love the commitment stage because it forces that sense of accountability that potentially people will avoid.

You bring up another framework somewhere at this point in the book, fit frequency intensity technique. It’s to apply if you’re an athlete in training, but how do you envision it applying to the average office worker?

I love this question. Frequency intensity and technique, anybody that’s ever worked with us through organizations, I always use sports analogies, but fit applies to anything that we do. If you think about frequency, it’s the cadence on how we do something. Intensity is like what we commit to the actual activity. Technique is that methodology you put in. I remember working with a good media call center. They were doing a bunch of outbound content development. The CEO at the time is like, “We’re tracking everything you mentioned. We’ve got the scoreboard and the frequency nail down. We can look at the call scripts and we can see that the technique is being followed.” It was interesting. As soon as we started listening to the calls, what do you think was missing?

Intensity.

Yes. They were doing what was being asked of them from the quantitative side and even following the methodology but they were not committing to the call. They were not elevating their tonality when we needed to. There aren’t leveraging the pause when they needed. If you looked at things in a Black and White perspective, it looked like they were falling what we asked them to do.

Once we elevated the level of intensity, they were in double digits or triple digit within a couple of months. Frequency, intensity and technique for us is a lot of ways. Almost like compliments the compounding effect. I think it’s Darren Hardy that talked about in his book. It’s about how often you do something and how much you put in, and that technique. We use this principle. More is more of an audit than anything.

You can apply to how often you coaching, what do you committing to the process, and what techniques are you using and evolving. Very much almost like the Tiger Woods concept. He could apply that to times on the driver range or in the putting range. It’s how we put into the process. I would say that the intensity is probably most people missed. You show up. We follow a technique we’ve been but we don’t lean into the process. Getting people to put the intensity in, it shows themselves that they’re capable of more. It’s a matter of, “Now that we saw, what’s next? What’s beyond where we’re at here?”

Leading Up, Down, And Across: The Power Of Peer-Level Coaching

You have a chapter at the end about leading up down and across. You may had mention to this earlier in our conversation. How does that connect to this Radicale Growth framework, the discovery, awareness, focus, commitment and follow-up?

That’s a great question. I find that we had to add this one in is because in a lot of cases, the reason why we must go back to the coach and coachee perspective. People think of leading or coaching as a top-down mentality. I said, “I can only apply this theory to the people I’m leading.” I’ve seen people fly this technique to people on their peer-to-peer group, where they’re not their direct supervisor. They’d be a counterpart or somebody that they could do cross collaboration with.

This has expanded the relationship. In a lot of cases, when we’re leading up, it’s a matter of, how are you asking questions to your boss to get deeper inside? How are you making people like even a boss more self-aware and saying, “Based on the last strategy that we just went through, is there anything that we could have changed or could have done differently to perform at a different level?” You’d be surprised by just asking some of those questions in an opera perspective to a boss or a leader.

The answers you get, because they’re used to just taking orders from that perspective. Those are the people that usually get elevated because they’re engaging their boss or leaders differently. It’s transformed a lot of relationships that we saw from a middle management to opera management layer. It gives them better communication pass by and having what I would call coaching culture inside of their organization. Not only does it influence growth, it truly influences the way that people communicate with each other.

I remember I was having one of those flag moments, where you hold them up because we’d sit in a lot of the team sessions, the strategic sessions. You see somebody wanting to tell somebody something and I would go, “I know where you’re going with that. How could we use a question to take that direction?” They’d pause and they would change it. It would change the direction of the conversation in a good way and still getting to the destination that they want to. That’s a little bit of the concept of the up, across, and down, but back to the coaching culture and influencing the way that people communicate.

If you can get comfortable asking those questions of your peers of people in other parts of the organization of your boss, and you do it from a perspective of good intent and curiosity as oppose to, why wouldn’t you do this or why are we doing it this way? Questions that are very leading and a little bit confrontational.

I love when people who work for me couple levels down the organization come and ask these very open-ended thoughtful questions that get me thinking because it gives me a sense of what’s on their mind. It also forces me to think and articulate where I’m thinking that may still just be in my head. It is very helpful. It is great when you can have those conversations with people who are comfortable enough to have with their boss or their boss’s boss.

You hit like the perfect word. It’s funny. If I had another title for the book, it would have been Curious Coach because I feel like curiosity is one of those areas that when you think about questions, you think of when you’re a kid or you run into kids. Those are always asking questions but they’re doing it in a way that they just wanted to know more information. Versus, sometimes when people do it intrusively or investigative, people get very protective. It’s the curious way of asking questions that gets you at the new information.

From Dragons’ Den To Radicle Growth: An Entrepreneur’s Career Journey

Before we wrap, let’s spend a little bit of time on your own career journey. What did you get your start doing? How did you pick that?

In my first business, I was in university and in patented a product that was in the foreign industry. It was a two-piece plastic clip that popped together and tighten your laces just in case it loosens your laces. I was on one of the TV shows called The Dragon’s Den, which is Canadian version of the Shark Tank. We got a great investment that year from a couple of great investors and get to scale it all over the world.

When I was in my early twenties, I got the chance to meet with some of the Fortune 500 companies and work on some great deals and get that experience then I sold that organization. I would say it was my first professional experience. I was diving into a company called Glentel. They were large third-party cell phone dealer at the time. I had no plans and ten years later, I was still there. I met some incredible leadership through that organization, but I got to appreciate the level of corporate structure, leadership, and what true leadership looked like. I’m felt very fortunate to be able to go through that experience, both through a business perspective and the entrepreneurial side as well.

When you’re on the entrepreneurial side, it’s very demure than being in a big and more established company that’s had to grow up, if you want to call it that. I’m sure for you and specially with what you’re doing now. It’s got to be a big benefit to have done both because you can understand that entrepreneurial side. You can also understand corporate structure, corporate organization, and corporate politics, and all of those things that are inherent in any size. If you’re going to come in and consult and coach leaders, you’ve got to have some awareness of how those things work in practice.

I was talking to one of the senior leaders from that organization when the book came out because I wanted to send them a copy. I honestly said, “I still believe very much so that I wouldn’t be where I’m at unless I had that corporate structure because it allowed me to have that rigidity to do what I do and transfer that over to organizations that we work with.”

What’s ahead for you?

I’m focused now on getting the book launch moving and driving that forward. Be able to share that experience with organizations, teams, and individuals. We’ve got a book launch coming up on March 25th, 2025, which we’re excited about in Halifax. We’re going to keep growing, expanding, and diving into that coaching and teaching the coaching program. We have a radical growth coaching program. We work with organizations to speak to that coaching culture I mentioned to equip them with the right methodology to influence organization’s growth path internally and externally. I’m excited what the future has in store.

Good luck with all of that. What’s any last advice that you want to offer to our audience?

I’m always a big believer of continuous improvement. Probably a statement that I’ve always used and I believe it’s in the book is well. It’s a quote, “Good, better, best. Never let it rest until you’re good is better and your better is best.” I love that idea that. I like the word potential. It’s an endless cycle. As long as we keep investing and keep learning in.

I’ve never heard that expression before but I like it.

I appreciate you having me on the show and amazing questions. Thank you very much.

Dave, good luck with the book launch and everything you’re doing with Rumin8 and Radicale Growth. It was great to get to know you in our conversation.

Thanks very much.

Take care.

—

Thanks for joining me to discuss his company, the Rumin8 Group, his book, Radicale Growth, and a little bit at the end about his career journey. As a reminder, this episode was brought to you by PathWise.io. If you’re ready to take control of your career, join the PathWise Community. Basic membership is free. You can also sign up on the website for the PathWise Newsletter. Follow us on LinkedIn, Facebook, YouTube, Instagram and TikTok. Thanks.

Important Links

• Dave Reynolds on LinkedIn
• Rumin8 Group
• Radicle Growth: Transform into an Unstoppable Leader through Mastering the Art of Questions
• Fierce Conversations
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About Dave Reynolds

Dave Reynolds is a serial entrepreneur who has launched and developed a variety of new products and services for nearly two decades. He is the founder and CEO of The Rumin8 Group, a Growth Consulting firm that helps clients think strategically, facilitate team growth, and navigate crucial conversations. With a background in sales leadership, performance management, and succession planning, Dave is passionate about growth acceleration and how asking the right questions yields the best answers. He lives in Halifax, Nova Scotia, Canada.