The art of asking better questions

In this episode, Lucy is joined by Dave Reynolds, founder of Ruminate Group and author of Radicle Growth: Transform into an Unstoppable Leader Through Mastering the Art of Questions. Dave shares his journey from sales leadership to global coaching, and why he believes the key to exceptional leadership lies in asking better, deeper questions. Drawing on the concept of “radicle” growth—the unseen but essential root stage of development—he encourages leaders to invest in meaningful conversations rather than chasing quick fixes.

They discuss the difference between mentoring and coaching, and why coaching creates greater ownership, accountability and long-term results. Dave explains how silence, often uncomfortable for leaders, can be a powerful tool to help people think for themselves and reach more thoughtful conclusions. He also highlights how surface-level conversations can limit real connection and performance.

Finally, Lucy and Dave explore the role HR can play in building coaching cultures. From helping leaders ask the right questions to observing how they run meetings, HR has a vital part to play in encouraging more thoughtful, human leadership. 

Contact Dave:

00:03 – Lucy Adams (Host)
Welcome to HR Disrupted with me, lucy Adams. Each episode will explore innovative approaches for leaders and HR professionals and challenge the status quo with inspiring but practical people strategies. So if you’re looking for fresh ideas, tips and our take on the latest HR trends, subscribe wherever you get your podcasts. So a major consulting firm was looking at which of their leaders delivered the best performance and results, and they studied how their best leaders interacted with their teams compared to the average, interacted with their teams compared to the average, and whilst there weren’t many differences between them in terms of leadership technique, there was one thing that really stood out the better leaders asked more and better questions, and my guest today is an expert on helping leaders to be better at coaching their teams through the use of great questions, and his name is Dave Reynolds, and he is the author of the bestselling book Radical Growth Transform into an Unstoppable Leader Through Mastering the Art of Questions. Welcome, dave.

01:19 – Dave Reynolds (Guest)
Thank you so much for having me on the show.

01:22 – Lucy Adams (Host)
Oh, it’s good to have you here and you’re in Nova Scotia in Canada, aren’t you Correct?

01:29 – Dave Reynolds (Guest)
Yeah, and it’s just starting to warm up now, which is great.

01:32 – Lucy Adams (Host)
Oh, fantastic, fantastic, Right. Well, look, we always start by asking our guests just to talk a little bit about your journey, find out a little bit more about you and what you’re doing now. So we’ll get onto the book in a little bit, but just talk about kind of your journey to what you do now. And I think you run a company called Ruminate, is that right?

01:52 – Dave Reynolds (Guest)
Correct. Yeah, we have an organization called the Ruminate Group and so our growth consulting firm where we support organizations all over the world from, you know, executive coaching to succession planning and you know also performance management in a lot of areas. So it’s been an exciting journey because we’re very industry agnostic, so we get to solve problems in all different types of industries.

02:14 – Lucy Adams (Host)
And that’s just one of the joys, isn’t it, when you move out of the corporate world and you go to actually work in more of a consulting capacity. Just it’s fascinating just seeing the many similarities, of course, between organizations and sectors, but also the different cultures and the different ways that they do things, and I think it is just one of the delights of actually the work that we do. And how did you get to do that? Was it were you kind of a career consultant or did you work in corporate life at all?

02:46 – Dave Reynolds (Guest)
You know that is an amazing question. It’s actually kind of a career consultant, or did you work in corporate life at all? You know that is an amazing question. It’s actually kind of a funny story because I was in telecommunications for years, growing and developing big sales teams, and I remember, you know, hosting an NHL game. We had a box and brought a couple of guests out and somebody that I knew quite well had brought his wife along and she had a big real estate company.

03:07 – Lucy Adams (Host)
You’re the ignorant UK person here. The NHL is what.

03:12 – Dave Reynolds (Guest)
The National Hockey League.

03:14 – Lucy Adams (Host)
All right, yeah, so you’re like your national sport, right. So that’s like the big thing that you do, huge, huge.

03:21 – Dave Reynolds (Guest)
We bring everybody out, we’re having this big event and you know I’m not a huge hockey fan. So I’m over there talking to her about her organization, I’m asking a lot of questions on how she runs the team meetings, what does accountability look like? And she kind of paused after a while and she was like why don’t you just come in and do some coaching for me? And without even thinking I said yes and jumped in and so, as kind of a side hustle, I started working with her as a consultant and coach. And her husband, which is in kind of a side style industry, said hey, would you come do it for me as well? And I ran into somebody for coffee and she was at a big law firm. I kind of explained what I was up to and she said we really need that law firm as well. And so one thing led to another and then I actually ended up leaving the telecommunications job just to pursue, you know, diving deeper into consulting, and never looked back since, and it’s been eight years.

04:20 – Lucy Adams (Host)
Oh, that’s amazing, and I think you know it’s a really interesting lesson, isn’t it? You know, if somebody’s got a real passion for something and they’re pursuing it as a side hustle, keep going, because chances are it’s what you really love and ultimately, to be paid for what? And it’s spelt slightly differently, isn’t it In that? It’s not spelt R-A-D-I-C-A-L, it’s R-A-D-I-C-L-E Radical Growth, so you’re going to have to explain that, but also give us a snapshot of what’s in it.

05:00 – Dave Reynolds (Guest)
Yeah, and so just going to the name, it was interesting. I was working with one of our other consultants on developing what we have, a radical growth coaching program, and she always saw me go up to the class and I would show them a plant and I’d show them a seed and I’d say, well, you know which one would you rather, have a plant or a seed? A lot of people are like well, we want the plant because we can see when it’s dying, we can throw some water on it and we throw some water on it. And so I kind of always use the analogy of you know, you’ve got to water the seed, you’ve got to nurture the seed, it grows roots.

05:27
You really don’t really see the growth right away. So we start getting this term called radical, which is actually the first stage that a seed takes when it breaks through the shell and establishes a root. And why this works so well for our book is that we just find so many people try new ideas and they give up on them right away because they don’t see that immediate surface level growth. But radical is about establishing roots. You know structure, perseverance, commitment and that’s a really big part of coaching as a whole, because you’re really making a major investment in a team or an individual. So radical for us, really stuck, because it’s really that commitment to realizing that growth is happening, sometimes when you just can’t see it.

06:11 – Lucy Adams (Host)
That’s really interesting. And I think HR you know my profession we’re probably a little bit guilty of that. It’s like right put on a training program, see immediate changes in behavior. But of course all of these behaviors they’ve been embedded over years, haven’t they? So of course you’re not going to see something transform immediately. So I love that concept. So talk to us about what the book is. I suppose the main kind of thrust of the book, the main ideas in there, just to give our listeners an idea, Absolutely no.

06:43 – Dave Reynolds (Guest)
It actually came from actually talking with a client, as we worked a lot with organizations on coaching culture.

06:50
So really going in and coaching one-to-one on executives and one of the CEOs at one point said you really need to develop a program that allows us to take this program on.

07:01
So we have some internal facilitators. And I immediately said like yes, just like I jumped into consulting. But I started thinking about this would be a really good opportunity to start putting this into a book where people could really go through start to finish on how we see coaching, consulting, the way we approach questions, our structure, and we do it in a very simplified fashion. So we try and make things so they’re not overly complex. But it gives you a paradigm shift on how you think about approaching coaching and you do coaching with somebody instead of for somebody, and it really changes their perspective on their relationship, on how they have coached versus how we show people, how we’ve, you know, done coaching for years and the organizations we work with and the people that have read the book the feedback’s been incredible so you take a slightly different approach, albeit it’s one based on kind of you know, ancient philosophies of, I think, greek the Socratic approach, and in your view, this works far more effectively.

08:10 – Lucy Adams (Host)
So, rather than the kind of traditional top-down leadership methods, you talk about a collaborative, socratic approach to coaching. Can you just share a little bit about how these approaches differ from what people might understand as typical coaching?

08:26 – Dave Reynolds (Guest)
yeah, and I would even say like one area that’s really good to kind of look at is like kind of the difference between mentorship and coaching.

08:32
And I’ve been in a lot of industries where you have these really strong mentors and they’re using their own experience to tell you what you should do, um, and there’s a lot of times that works really well, but what they’re doing is they kind of have an internal bias of what they believe works because they’ve been really successful, but that doesn’t work for everybody.

08:51
The beauty with coaching on asking somebody what they already know and helping them structure it into a system by asking questions is more effective, because when you ask somebody a question, they have to be the one that owns the response and it just totally changes the level of ownership and accountability. When you’re asking questions in a coaching environment, you really get people to lean into a conversation where they’re used to being talked to versus talked with. And we always say the difference between mentorship and coaching is sometimes mentorship feels like a one-way conversation versus coaching is a two-way conversation and people feel more heard, they feel more connected with and they walk away with a sense of ownership of the conversation versus a directive. So that’s probably the best way that we look at it.

09:38 – Lucy Adams (Host)
And in the book you sort of talk about that. You know leaders need to master the art of these kind of questions. Can you get really practical now and give master the art of these kind of questions? Can you get really practical now and give us the kind of kinds of questions that you see would be typically most effective in that kind of coach coachy relationship?

09:56 – Dave Reynolds (Guest)
yeah, and you know I would. I would say questions are like anything. It’s kind of the law of 10 000. You have to master it along the way because it seems very simple and straightforward to just ask questions, but it’s about timing and design. But I would say, just looking at open-ended questions, confirming questions, mirroring questions there’s all types of different questions, but anywhere you can start broadly and then break it down to be more specific so you can get sequences into the questions.

10:26
A common one we see in sales all the time that gets missed is you know, I walked with a CEO and he asked one of the leaders, you know, how are sales going? And he said sales are good. And he kept walking. We just paused and I said, oh, perfect, tell me how your month’s going. And he said, oh, right here, hey, what did you set for a goal? So we’re trying to sequence there. Perfect, what are you trending right now? And so he starts kind of saying okay. So I said the trend sounds like it’s under your goal. We’ll go back. How are sales going for the month? And he said, wow, we’re struggling here.

11:05
And it was interesting because it changed the dynamic of the conversation, because we were willing to go deeper by asking more questions. So some people are really good at asking surface level questions and getting surface level responses. What we try and teach in the book is how do you go deeper with the idea of where you wanted to start? If you want to know how sales are, you need to go a little bit farther into what’s the current reality. How self-aware are they? How focused are they on making change? And those are really transformative ways of connecting more with a client. And so the CEO saw this and it was interesting. When I came into the office the next week, I saw him and I didn’t even have to ask him. He said hey, we made some changes and we’re seeing a really good uplift. So it was like he felt there was a sense of accountability because we were willing to go a little bit deeper into that conversation. And that’s ultimately. What we want is that we want to kind of both people to lean into the process.

11:52 – Lucy Adams (Host)
And why do you think leaders struggle with this then? Is it just that they’re too busy, or they’re not thoughtful enough, or that they perhaps lack some kind of empathy gene? You know what is it? Why do leaders do that classic thing which you know, I’ve had a million times from my bosses? How are things, in fact? I remember one time not a coaching question, but my boss asked me how my weekend had gone, and I kind of went into the detail of how my weekend had gone and I realized at the end he actually really didn’t want to hear how my weekend had gone. He just wanted me to know. He’s asked a question, he’s got an answer, it’s all done and he can move on to the next thing, which is giving me a task to do. So what is it that stops leaders from being great at asking the right questions?

12:44 – Dave Reynolds (Guest)
Yeah, so we love this question. Reason being is we’ll go back to the surface level. If you stay at surface level, you’re never going to run into resistance, you’re never going to run into friction. It can be very transactional and you can move on and you feel like you’ve made that check the box or the connection point right. But it’s like a common saying is like everybody communicates but few connect.

13:06
So when you think about that is that most executives or leaders, they miss the opportunity to have that real conversation and the real conversation being find those friction points, because that is really where you’re going to be able to open up a bigger conversation. And I would say more relationships have ended by what wasn’t said than what was said. And so I think you have to have the willingness to get into a tougher conversation. And I would say the next area that most people struggle with is that if they get to silence or they get to a set of resistance, they don’t know how to overcome that in a logical way, because most people will respond emotionally and they don’t want to get into a reactive style conversation and coaching is really about how do we create a friction point that we can address it logically but in a proactive way, and we do that through questions and that really gives people space and time to respond in a way that they walk away going. Oh, that feels really good.

14:06 – Lucy Adams (Host)
Now you mentioned about silence there and you talk in the book about how silence can be a really effective communication method in coaching. What do you mean by that and why do you think that is?

14:19 – Dave Reynolds (Guest)
yeah, I experienced this early on in my career with what I would say probably my most influential mentor and his name is Pablo and he used to ask these, really I would say tough questions, not complex but straightforward, and I would quickly respond with, again, surface level. Surface level. You know, things are good, this is an area we’re going, this is a strategy, and he would be okay, perfect and what else. And he would be really good at digging deeper and I could easily say, well, I’m not sure. And he’d say, well, okay, why don’t you take some time to think about it? And let’s say that he would have no problem sitting there for a minute and letting me struggle.

14:59 – Lucy Adams (Host)
It feels like an hour, doesn’t it, when you know a minute silence in a conversation, particularly if you’re an extrovert, is just a killer.

15:07 – Dave Reynolds (Guest)
I felt like a fish just plucked out of the water and you’re just flopping on the ground because you’re waiting for somebody to save you and you’re looking around. There’s nobody there. And so the moment made me lean into saying and you would go a little bit farther. He reinforced that we’re moving in the right direction, so he’s helping guide me. And it got to the point where I’m like okay, I see the methodology, I see the science behind it, because he wasn’t going to stop, because he knew the benefit it was for me to become a more independent thinker when, again, again, dependency is you’re going to check the box, you’re going to do something transactional. So I started using that with my teams and I started seeing the major change where they’re used to saying, well, I don’t know. It’s saying okay, if you did, what would you say? You know, or you know what’s something you thought about that you haven’t tested. You know what have you been working on that. You know what’s something you’ve thought about that you haven’t tested. You know what have you been working on that you know is outside of your comfort zone.

16:03
And just like getting people to table new ideas in a way that they feel comfortable so they can be, you know, transparent about how they feel, or they can be vulnerable. Something that silence really did, was it allowed people to think about their own ideas without somebody jumping into that silence and telling them what they should be saying. And I think that is the biggest challenge, and I think Susan Scott, who has a great book called Fierce Conversations she I don’t know the exact quote, but I think it’s really let silence solve the puzzle. And I love that, because a lot of times you’re asking a question to put pieces on the table. Silence allows them to put the pieces together instead of you forcing the pieces together on your own, and that allows them to feel like, again, they own the response and you can always ask for clarity and keep going. And I find this is just such a pivotal part of communication as a whole.

17:01 – Lucy Adams (Host)
I’m just reflecting as we speak, dave, about what a terrible leader I am. I’m just going to go back to basics and really think about bringing in some of these practices into my leadership style. Because it’s so easy, isn’t it? When you’re a busy leader, shit start. Because it’s so easy, isn’t it when you’re, when you’re a busy leader, to just go for the quick response to tell them, rather than, um, get them to get to the answer themselves. And um, and of course you know, having been in both situations, as a boss and as an employee um, if you know that your boss is going to jump in and solve it all for you, you just stop thinking, don’t you? You stop thinking for yourself, which is the last thing we need.

17:46 – Dave Reynolds (Guest)
Well, I agree, and one thing I would just add is that I find that people don’t allow space to have those real conversations. So they’re having a conversation. They’re like oh, I have 15 minutes to have this conversation, or I have five minutes to have this conversation. I have two minutes to have this conversation. I have five minutes to have this conversation, I have two minutes to have this conversation. So I don’t want to get deep enough into the conversation that actually becomes a real conversation. I just want to just confirm something, and so we always call those like drive-by conversations, and people are swinging by having a conversation and then they’re exiting and it’s.

18:15 – Lucy Adams (Host)
It feels like you’re patting somebody on the head with a conversation, versus really important to signal which of the conversations it is you’re about to go into as a leader, because actually sometimes you just want confirmation, don’t you? And you know I mean I, I’m terrible, I have to kind of start emails again with you. Know, did you have a good weekend, you know, because my, my instinct is to go straight into progress, chasing or asking a direct question about something. So actually, that that kind of signaling which kind of conversation this is might also be helpful. Because you’re right, you know, if you start to kind of open stuff up and somebody is starting to engage with it and you literally don’t have the time that you don’t want to shut them down, do you?

19:03 – Dave Reynolds (Guest)
no, and I think setting like that’s a really good point is around setting parameters around having a conversation. Uh, and also, too, so people feel prepared for the conversation. So some people feel uncomfortable sometimes having a conversation they’re not prepared for. So a lot of times when we’re setting coaches or teams up, it’s a matter of how do you want to proactively prepare them for this conversation? But to your point of your kind of have five minutes, you know it can’t be a bigger conversation saying hey, I heard something really interesting. Do you have time later for us to sit down and maybe have that conversation around sales, operations, marketing, whatever it might’ve been, and allows them to say, hey, is there anything I could prepare for that conversation? And it’s a transaction of having something more formalized, and I think that’s really important because it respects each person’s boundaries, but also, too, that it’s a priority.

19:54
I think that’s the biggest challenge sometimes that when employees are being communicated with, they don’t feel like a priority, and I think we can turn that over. Don’t feel like a priority, and I think we can turn that over. That they feel like a priority. They feel like that conversation was an investment. Um, that’s when we really truly start. Measuring success in organizations is where they can see that really transformative investment in each other and a prioritization of having those conversations so in the book as well.

20:20 – Lucy Adams (Host)
You talk about. Some of the biggest problems around coaching programs is it’s not that people perhaps don’t have the answers, it’s that they don’t then act on those answers. So what are your suggestions for creating that action?

20:36 – Dave Reynolds (Guest)
Yeah, and so this is really built into our program and built into the book is that you know, we’ve observed a lot of really good coaching programs or really a lot of transformative organizations that have conversations where they pull a lot of amazing answers out, whether workshops or they’re one-to-ones, but there’s no defined next steps or commitment or focus. So sometimes you pull 10 ideas out. The law of diminishing return is you’re probably not going to do any of them. You would be better off to say let’s pick one idea and execute on it. Where we see really strong ROI is commitment. Okay, perfect. We just reviewed all these.

21:15
What is our next steps and when should we follow up on that? And so what we see in the coaching programs that we’ve implemented is not only are we getting more commitment to the action, but the person’s picking the action themselves and they’re making a commitment and ownership over it and we’re setting up the next meeting to follow up on it. So commitment and follow-up it’s kind of like we always think of, like chain link. It’s that link that really pulls that meeting or conversation to the next one, and there should be that sense of connection. So instead of jumping into the newest idea or how was the weekend, it was more.

21:49
Hey, I knew we met last week and I really valued that conversation. I know you made a commitment. How did that go? And they’re able to say, okay, I’m being held accountable, they’re falling off and they are invested in my commitment and they’re able to either say they executed or they didn’t. And it creates a two-way conversation to say, okay, how do we reinforce to get that back on track and commit this week? Or you give them that sense of recognition that they deserve to reinforce commitment and consistency to execute and to me, that’s where the program really grabs legs and evolves is when we find commitment, execution and then follow-up systems and that really starts building a culture for accountability so obviously this is a typically a podcast that’s listened to by h professionals and you know we may have some people listening who love the ideas and we’re going to get the book.

22:44 – Lucy Adams (Host)
But obviously HR is that kind of intermediary between leaders and their employees in that it’s, you know, helping leaders to take these tools and to coach their people better. How would you say HR professionals can take your suggestions and help their leaders?

23:06 – Dave Reynolds (Guest)
We’ve been really fortunate to be right in the middle between leaders in HR and sales in HR in a lot of different divisions, and I’ve actually sat down with a lot of leaders and you know we work a lot on, you know, the actual human capital management side. And they’ll say, hey, you know, you’re looking at our teams and we need to get rid of these two people on our team and we need to recruit and place new people. I said, okay, perfect, I understand that quantitatively, the metrics are down, they’re not performing. Can you tell me a little bit about the investment you’ve made in, uh, those people? I know they’ve been here for less than a year. They were hired for the right reasons. Uh, can you walk me through what the coaching looks like? You know, can you walk me through their former views? And I would say in almost all cases, no investment was made. So they just anticipated that because of their history, their track record, they were going to come in and it was just going to be fluid. And a lot of cases that’s the biggest challenge that most organizations face is that they expect something from that employee that they’re not giving. So as in. It’s not a two-way street again, giving so, as in, it’s not a two-way street again.

24:20
So I would say, from an HR perspective is looking at execution on performance reviews, coaching that leader’s investment in those employees.

24:25
And I would say the best way to link that back would be formal and informal touch points and how they’re tracking those throughout, Because we always look at coaching kind of like they talk about the emotional bank account that every time you’re meeting with somebody, you’re making an investment and at some point you need to make a withdrawal if there’s a challenge or there’s an area that needs to be addressed. But if you haven’t made an investment, I know what it’s like trying to take money out of an account. There’s none there. It’s pretty challenging. So I would say HR could really look at the idea of you know, when we look at leaders, how are they investing in their teams and how are they showing year over year growth with those team members? And if there’s somebody that’s new to the team, how are they investing so they have traction, they get momentum and they start moving forward. Those are the areas that I see to be most transformative. That, I think, is probably one of the bigger gaps that we see in the market.

25:15 – Lucy Adams (Host)
And I think also just sometimes giving leaders some great questions to ask. You know I think you know it can be very, very practical and I think you know sometimes leaders like the idea of trying this but just giving them two or three questions that they you know they might not have thought about, to help open up those conversations. I mean, I think that kind of short, quick, helpful advice that HR can give, rather than perhaps the big training programs around coaching.

25:46 – Dave Reynolds (Guest)
And even something simple that I would probably throw in is that you know we’ve sat with organizations and done this and said we grabbed some from HR because we work with them on succession planning. I said why don’t we sit in on some of the meetings and just see how the meetings are operated? And so it’s interesting, when you see a leader run a meeting, our immediate check is are they engaging team members? Are they doing it in a servant style leadership? Are they including everybody else?

26:11
Who owns the meeting and also, too, what’s the structure for the meeting. And we found that had such a transformative way of are the team members lenient? Do they feel like they’re part of the strategy or do they feel like they’re being facilitated? The strategy and that was a really eye-opening experience where HR and the leaders could work together on a better structure for just overall team meetings, on how they prepare for them, how they execute them and then how they have kind of a post-meeting structure. That, for us, is a huge ROI on both sides.

26:43 – Lucy Adams (Host)
Absolutely. I couldn’t agree more. Okay, let’s wrap up A couple of questions. First of all, someone’s just finished reading the book Radical Growth another plug and they’re excited to put it into practice. Where should they start? What’s the first thing you’d tell them to do?

27:02 – Dave Reynolds (Guest)
yeah, I would reach out to us at ruminategroupcom so it’s r-u-m-i-n number eight groupcom, uh, or through, uh, through email at info at ruminategroupcom. But I would really, you know, take what is, what are the key ideas, because there’s activities on each chapter that you really want to implement and reach out to us, jump on a discovery call or, if your organization’s saying, hey, we really want to lean in and embrace this philosophy and build our coaching culture. We have a full program called radical growth coaching program where we take people through six modules dedicated, like the book, to really certify each of those leaders through the program so you can have a consistent methodology in your organization. Or, if you’re an individual coach and you’re trying to, you know, maybe even set up your own business, we could work one-on-one with those organizations as well or those individuals to really kind of help them. You, you know, escalate and scale that opportunity.

27:59 – Lucy Adams (Host)
So you’ve probably answered this question as well, but where can people reach you?

28:03 – Dave Reynolds (Guest)
Yeah, no, perfect, great, I’m probably jumping the gun on that one. But yeah, it would really be LinkedIn. If you look for Dave Reynolds on LinkedIn under Ruminate Group and also to info at ruminategroupcom. Would be the best way to reach out to us.

28:18 – Lucy Adams (Host)
We’ll put those links your LinkedIn link and the email into the show notes so people can get in contact and also you can check out Dave’s book. Dave, thank you so much for joining us today. It has been great chatting to you, giving me plenty to think about. I’m going to think about how I prep for my team meeting tomorrow in a slightly different way now, so thank you very much for your time and thanks everybody for listening as ever.

28:49
If you liked it, then do let us know, and if you want to keep making sure you don’t miss an episode, make sure you subscribe and you can reach us at DisruptiveHRcom. Thanks everybody. Bye for now.

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