Turning tough conversations into better conversations

Episode 105: David Wood joins the podcast to discuss his four-step process for mastering tough conversations.
June 2020

David Wood

Business and Life Coach, Play For Real


Turning tough conversations into better conversations

Having a tough conversation can feel like a daunting task for everyone involved. However, there are strategies you can employ to ensure a better outcome from these conversations.

David Wood joins the podcast to discuss his four-step process for mastering tough conversations. Plus, David and Ben walk through an example of a tough conversation that you may come across as a financial advisor.

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In this episode:

  • The four steps to the CARE model
  • An example of the CARE model in action
  • What happens if the conversation still doesn’t go well?
  • The power of positivity and transparency through these conversations

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Emily Larsen – 2020 has been brought many new conversations into our lives and our work. Some of these topics of conversation can be tough, emotionally charged or even awkward. Even though we use a benign example in this episode we feel that the techniques, tools and wisdom David provides will be invaluable for you as you navigate the remainder of 2020 and beyond.   

David Wood – When you have tough conversations you can lose things. But ultimately, in the long run, they’re probably things you can stand to lose and would be good for you to lose. Speak your truth 30% more than you currently are, and your life and your business will go better.  

Ben Jones – Welcome to Better Conversations. Better Outcomes. presented by BMO Global Asset Management. I’m Ben Jones. 

Emily Larsen – And I’m Emily Larsen. On this show, we explore the world of wealth advising from every angle, providing actionable ideas designed to improve outcomes for advisors and their clients.  

Disclosure – The views expressed here are those of the participants, and not those of BMO Global Asset Management, its affiliates or subsidiaries.  

Emily Larsen – At the top of the show, you heard from our guest, David Wood, about creating space to have tough conversations. Tough conversations might be with clients or team members, family or friends, anyone really. And the strategies we’ll be exploring in today’s episode are designed specifically to aid you in making those tough conversations into better conversations. After all that’s the name of our show!

Ben Jones – David Wood is a business and life coach with Play for Real. He works with high performing teams, companies and individuals to help them create amazing results and deeper connections. Later in the show, David’s going to share his four-step process for mastering tough conversations; but first, David is quite a character with a surprising back story. So let me introduce you. If you could David, like, how did this come to be your life’s work? Like maybe you could just tell me a little bit of your story, and how this came to be.

David Wood – Sure, well I grew up as an actuary, believe it or not. I was really good at math and thought I’d be an accountant and then I found out that an actuary seemed to be really hard to qualify and got paid more. And so I’m like all right, let me try that. So I became an actuary, and I was hugely left-brain. I was good with systems. I actually have some small personality, so I was able to work for a consulting firm, as an actuary, and ended up getting a transfer to New York. My clients were Sony Music, and Ford, and Exxon and Chanel. It was amazing at the age of 24. But I wasn’t really happy, and someone suggested I do a personal growth workshop, a self-help seminar. And even though they all smiled way too much and they all wore nametags and it looked totally culty,, I thought let me check it out. And it changed my life. They actually cracked my cynicism. I discovered that I didn’t know anything about vulnerability and deep connection, and really influencing people and emotional intelligence so I say at the age of 26 I embarked on a journey of discovery, and I’ve spent the last 20 to 25 years kind of catching up on what I think it means to be human. So now, the clients who come to me don’t just want business coaching and they don’t just want life coaching where we talk about how’s your relationship with your kids, and with your partner, and what really makes you happy. And how’s your integrity and your authenticity? They want both. And I found the two intertwine very nicely when we work on career and we work on life, each feeds the other.  

Ben Jones – You know, I got to ask. Did you pass all the actuarial exams?

David Wood – I did.

Ben Jones – Wow, I’m incredibly impressed.

David Wood – I’m beaming, because it’s rare that anybody actually knows what an actuary is. Your audience would be different but for someone to know what it is and appreciate — I sweat blood and tears. I‘d like to say it was easy for me to qualify, but I was top of my school and then when I discovered the actuarial science I was not top anymore, in my class. And it took me — I think it look me eight years from start to finish to qualify and that’s apparently in the scheme of things that’s actually not too bad. But it was brutal and I don’t recommend it to anyone unless you’re way smarter than me. Because it was just harder than I thought and had I known how hard it was going in I probably would not have attempted it.  

Ben Jones – I know how hard those exams are, and I have friends who have spent, like you, many years trying to get through them, so very impressed on my side of the mic here.

David Wood – Thank you! And then, Ben, once I qualified, I worked for another year and then I quit. So that’s the bizarre thing. After eight years of studying and then I made it and then presumably I was on a partner track, and I quit. Then a year later, after playing guitar in pubs and for parties and even on national TV, I actually resigned from the Institute of Actuaries of Australia. That felt like stepping off a cliff.  

Emily Larsen – To start, we asked David about his secret for coaching high performing teams and he told us that he tends to focus on enabling tough conversations. For you, this might be a conversation with an employee or colleague, or even one of those tricky emotional encounters with clients.

David Wood – I was raised in a country town in Australia, and I wasn’t taught how to be with strong emotion. And I imagine that a lot of advisors would at some time have a client cry. Would that be right?

Ben Jones – Yeah I think that’s right.

David Wood – Yeah. People are going to cry. Some people get frustrated. Some people might get angry, some clients are going to have really awkward conversations about their will and what they’re going to do with their kids and can they not send their kid to college and Matt Halloran, who I think you know, he said to me he’ll have a room full of advisors. And he’ll say, all right, how many people have had a client cry? And then all the hands go up. He said how many people know what to do when that happens and all the hands go down. So I think one thing that we’d have an advisor be even more in the direction of superhero is being able to be with strong emotion and know what to do when that happens. If you can go to those tough areas with your clients and you have the space — if you can hold the space so that they can feel whatever they’re going to feel, then I imagine they’re going to be more attractive to their clients. I want an advisor who can hold space for all my emotion, that’s one thing, and then I also want an advisor who’s going to have the tough conversations with me. They’re not going to tell me what I want to hear. They’re going to be able to bring up issues that are hard to talk about and they’ll go there. Because then I’ll say to other people, oh my advisor will kick your butt, if necessary. They’re willing to have the hard conversations.

Ben Jones – You talk about this idea of tough conversations but like, what makes a conversation tougher or awkward? How do you define that?  

David Wood – A tough conversation is one you don’t want to have. And the reason we don’t want to have it is threefold. There are three big reasons why we want to avoid tough conversations. The main one is fear of loss. I could lose something. If I have a tough conversation with my client my client might fire me. And if I tell my boss, or my business partner, that I screwed up there could be real consequences of that. So fear of loss is a really powerful motivator to not want to have the conversation. Another reason we might not have it is awkwardness. We do not like discomfort. Humans will run from it. Ask any audience how many people take a regular cold shower. If my cup of tea is not hot enough, I’ve got to stop what I’m doing, go to the microwave, and handle this. So it’s a bit sad, but we’ve become creatures of such comfort and a tough conversation is one we can’t control. We don’t actually know how it’s going to go and we can’t control the emotions of the other person, what they’re going to say or whether they’re going to attack us. So there could be a lot of discomfort and now I’m coming to the third reason which is vulnerability. When we can’t control it it’s vulnerable. Here’s the other reason. We weren’t taught how to have a tough conversation. There are so many ways to do it incorrectly. Here’s one: Hey, Bill, we need to talk. If Bill’s anything like me, Bill’s not going to assume positive intent. Bill’s going to have flashbacks to childhood, and now Bill’s in trouble. So the fact that we haven’t been taught how to have a tough conversation is another good reason to avoid them because it might go off the rails. You might make it worse.

Ben Jones – I want to dive into that a little bit more. But before we get into that I’m curious, for our audience, like why do you think an advisor should care about this topic?  

David Wood – Firstly let’s start with humans and then talk about advisors. I think humans should care about this topic because if we avoid tough conversations, whatever issue we have can fester. I had a client who just talked so much I felt like I didn’t need to be there. That’s a tough conversation. You ever say to the client, you know, do I have your permission to interrupt you, if I think I can take the conversation in a direction that’ll give you more value? If I don’t say anything there’s a distance now between me and the client. I like them less. But if I could share it and we could come up with some kind of agreement, then I’m going to feel closer to that person and I’ll like them more. Then I’m more attractive to them because I’m liking them more. So I think humans in general should care about tough conversations because we have more influence over people and we can get great external results, like get that celebrity to endorse us or get that new business relationship or that affiliate partnership. Or that new client will sign up with us. We get those results for so many good reasons to have tough conversations as an advisor you get not only those results but you get to be more attractive to your clients.

Ben Jones – Tough conversations should matter to you as a human, and as a professional advisor. If you think about the best relationships that you have in every area of your life many of them have space for emotional discussion with both candor and mutual respect. That trust is what makes them special and it’s no different for your relationships with your clients.

Emily Larsen – Next, David broke down his signature four step process on mastering tough conversations. You don’t need to take notes for this section; we linked to a free worksheet from David about using his care model in the show notes. Make sure you check it out.  

David Wood – This is the CARE model: CARE. So the C stands for Clarifying the Issue, and you do this with yourself using the worksheet that comes in the download. You want to get clear on things like what’s your hope from this conversation? What are you afraid could go wrong? And do you have a request? It’s really great. You may decide not to have the conversation after you got clarity, or you may decide to go forward. But definitely fill in this worksheet any time there’s any issue with someone and you’re not sure how to address it. The A stands for Ask Permission. We’re not going to say we need to talk. We’re going to ask permission and set context for the conversation so that they might even look forward to it. The R stands for Reveal and Request. You’re going to share the issue and how you’re feeling about it, and if you have a request this is the time to make it. And the E is so important. Ben, I forget this so often. The E is Enquire. You want to ask about how it landed for them, how they’re feeling about it. Do they have any ideas that are better than your ideas, and you work it out together. You don’t want to have a tough monologue. You want to have a tough conversation. So this step is crucial.  

Ben Jones – If you’re scratching your head a bit at the last part David is using the more traditionally British spelling of “enquire”, with an E, rather than “inquire”, with an I. In this case, they mean the same thing. You just want to ask your clients how the conversation felt for them to make sure that they’re on the same page. To illustrate the model in action David asked me for an example of a tough conversation a financial advisor might expect to encounter.
I think for advisors there’s a number of tough conversations that come up, but I think one in particular is when you have a couple and you’re talking about potentially some estate issues, and mortality, and one spouse is doing a lot of the talking, and you can tell that maybe the other spouse has a different opinion, but isn’t speaking up.

David Wood – Oh yeah, yeah that’s really good. That one might be a simple one. I don’t know we’d need to use the four steps on that one. I imagine it’d be something like hey, Jenny, you sound like you got some really good ideas on this and you’ve thought it through. So great, I’m writing this down and I want to give Bill some stage time to have some input. Bill, do you like to generally follow Jenny’s lead, or do you guys worked out those decisions together? How do you guys work this stuff out? I might actually enquire from curiosity to find out, maybe they want to talk about the dynamic. That might be a simple one. But let’s suppose it happens a lot and your subtle questioning is not actually working out and you’re trying to give one of the partners some stage time. So you decide you know I think I actually need to have a separate conversation with someone – let’s say Jenny. I think this would be a really good one to use the model. So I clarify the issue. I go through the worksheet. It asks me what’s my hope. Well, my hope is that I can find out more about what Bill’s thinking. That’s my hope so both parties are really served. I want confidence that both people are served. I write that down. Then what’s my fear? Well my concern is that Jenny might feel offended. Jenny might get defensive. Maybe Jenny decides to go and find someone else who isn’t going to broach things like this so that’s my fear. I don’t know that I’d have a request in this. I think I’m more curious. I’d be coming from curiosity to enquire what is the dynamic and would it make sense for Bill to get a bit more stage time. And could Jenny even ask Bill some questions? That might be an idea, but I don’t think I’d go as far as a request in this one. So that’s the worksheet done. There’s one more question on that worksheet, that’s very important. How might that look from their point of view if I step into their shoes, so I might try and imagine — if you try and imagine, Ben, being Jenny for a moment what might it look like from her point of view?

Ben Jones – She might feel that you value Bill’s opinion more than hers. She might have thought that she talked to Bill about this and she was just speaking because Bill’s more quiet or reserved.

David Wood – Yeah!

Ben Jones – She may also feel like you’re dismissive of her opinion.

David Wood – Yeah, this is good. You’re starting to get some ideas of how it might look from Jenny’s point of view and we can assume positive intent. So let’s jump in now. On the worksheet there’s a box to check that says I’m willing to accept the possible consequences. I tend to be biased towards rolling the dice. I take good bets and I’d be like all right, I’m willing to risk the chance of her feeling a little offended. I’ll speak with her while she fills it, if that happens. So I checked the box. I’m willing to have the conversation. So let’s go into it and would you be willing to be Jenny? I’ll be an advisor.

Ben Jones – You got it.

David Wood – All right, great. So, ring ring. Hey Jenny, this is Ben. How you doing?

Ben Jones – You know what I’m doing good, thanks for the call. I’m actually surprised to hear from you, because we just met a couple weeks ago.

David Wood – Yeah, yeah we did. Well you know I realize that there was something I wasn’t saying and I’m hesitant to bring it up, and I think the reason is I thought it might be awkward to talk about and you might even feel a little bit defensive or awkward about it. And so I was like I don’t want to talk about this and then I thought hey I do want to bring it up because I’m so committed to serving you and Bill. And I think this might have me do a better job of serving you guys so I wonder if you got maybe five minutes to talk about something I think might help.  

Ben Jones – I got five minutes, yeah, sure. Anything you need David.

David Wood – Okay, great. Thanks! So I’m going to move onto step three, which is reveal and request. So I notice that when we have our sessions you seem to do most of the talking and Bill’s fairly quiet, and I wanted to raise that. Because if that works for you and Bill, if that’s the best way for it to work, then great, I’m on board. But I just wanted to check in, do you think it might work if Bill got a bit more stage time and maybe got to talk more, or do you guys already have a separate deal that you set up. I don’t want to be — I don’t want to offend you, and I don’t want this to be awkward so I just want to check in how is it for you that I’m even asking you, and bringing it up? Is it easy? Is it offensive? Is it something in the middle? I really want to know.  

Ben Jones – Well I’m not offended. I can see how you might think that. I mean part of it is Bill’s just not a talker and so I just feel like I need to speak on our behalf to make sure we get our wishes met.

David Wood – Yeah. That makes sense. Yeah. My guess is you have a dynamic that works for the two of you. Do you have any ideas about how I could elicit just a little more from Bill? It’s fine, maybe it’s going to be 70/30 or 60/40 but is there a way to bring him out a little bit more and engage him, if you even think that’s a good idea. And if you don’t we can drop it.

Ben Jones – What is it you want to hear from Bill?

David Wood – Well I just — sometimes I want to know his desires and I want to know if he has concerns. I’d like to know those too. I want all my clients. I want to know what their desires are and what their fears are so I can best serve you guys and make sure you get the best financial plan.  

Ben Jones – I mean, do you think he disagrees with me?

David Wood – I don’t know. I think that’s really the question. I don’t know.

Ben Jones – I think we’re really aligned but you know maybe actually the best thing, David, is why don’t you just call and have a discussion with Bill?  

David Wood – Okay, that’s a good idea. Yeah, I will! And I’ll say again I don’t want to force a square peg into a round hole. If you guys totally have a set-up that works for you let’s go with that. I just wanted to ask because I find if someone is not speaking then I’m in mystery. And I’m like I wonder what’s going on. So like great. I’ll talk to Bill and my guess is Bill is going to say you know what, Jenny and I talk about this stuff and she’s better at speaking, and so she speaks for both of us. That’s my guess.  

Ben Jones – Okay, well good luck with that conversation David and look forward to seeing you next time we get together.

David Wood – Yeah, and thanks for being so open in this conversation and talking about it. This is one of those areas that I think it’s tempting to just leave and gloss over. I don’t want to step over anything that might add value so thanks for listening.

Ben Jones – Okay have a good day!

David Wood – Alright, great. Let’s stop it there All right, great. Let’s stop it there. So we went through four steps. Clarify, Ask, Reveal and then we Enquired to find out how it landed. How was that for you, Ben, and what did you notice?

Ben Jones – I purposely tried to be a little bit put off or difficult.

David Wood – Good job!

Ben Jones – The one thing that I would say is I’m curious your perspective but when you reveal the request is it fair to say that you have other clients who when one partner is silent, sometimes that means there’s disagreement. And you’re just trying to make sure that you’re serving everyone’s desires? Sometimes it just makes people feel more comfortable that it’s not the first time you’ve had this issue.

David Wood – That’s a good point. Say hey it’s quite common that one person will speak more than the other, and sometimes it’s perfect that the other person, the quiet person feels fully served, and sometimes if we dig in a little bit we might find that maybe they got some ideas, or they got some desires that they aren’t saying. And so I’d like to give them a little bit more stage time. It can work either way. One of the principles in this is to welcome everything. There’s nothing wrong. Everything is good and everything is possible and we’re really just enquiring to make sure they get the best service possible.  

Emily Larsen – Ben tried his best to complicate this roleplay, but clearly David has navigated far tougher conversations. So what happens when emotions really start to run hot, and things don’t go according to plan?

Ben Jones – I’m curious as to what happens when you go through the worksheet, you’re prepared, you have the conversation and it goes just horribly. Doesn’t go well.

David Wood – Yeah you know what, sometimes it’ll go off the rails. This is the thing. When we have a tough conversation we are rolling the dice. We’re taking a good bet. The odds are in our favor because we got clarity but it may go off the rails. Maybe the person gets so defensive they can’t even listen to what you’ve got to say. So in that situation, I will often switch gears and I will be in the role of listener. I might say wow all right looks like a lot’s coming out for you. Say more about that. I want to hear everything you’ve got to say and then maybe I can finish what I was going to say. So you got to switch and let them get all the charge out and then I might ask, is there more? And when they’re done, say okay and I’ll reflect it back to them. This is what I’m hearing. Do I have it right? And once they feel heard, then they might be open to could I share my side now? Would you be open to that? So that’s one way it could go off the rails. And the other thing I want to say about that is just because they have a reaction and then maybe you had a reaction, and maybe it ends up being an argument, that doesn’t mean it was wrong to bring it up. I say rip off the band aid and get in there and find out what’s going on. Maybe you take some time to cool down and they take some time to cool down. You do the worksheet again and you go back in and you have a Round Two. Just because it doesn’t go well the first time does not mean it was a failure. That’s bringing up issues and that gives you information and then round two, maybe that’ll resolve it. Maybe it needs a Round Three. Maybe you end up agreeing to disagree. All right, seems like we don’t agree on this, but at least we know that now, and we’ve both got a lot of charge.  

Ben Jones – Let’s say that there is a lot of emotions. The example you gave me where you listened and then reflected back what you heard requires someone to be in the right mental state and it requires someone to not get really worked up themselves. What if you’re so worked up you can’t go there?

David Wood – Yeah great question. So firstly, you need to run off the charge before you go and have the conversation. The worksheet can help you with that. Talking it over with a friend can help you with that. Roleplaying with a coach can help you run off the charge. Say like oh this is what’s going on with me. This is why I’m worked up, okay. It’s less likely.  Then when you go in that you’re going to be triggered and I say it’s the responsibility of the most aware person in the room to lead the way so if I can see what’s happening, I got a little bit of charge. They got a lot of charge. I’m the one that will say, okay why don’t we switch gears here. I want to listen to this. Tell me what you got. There are times when I said to someone, wow, you know what? I brought so much charge on this I can’t actually hear you right now. I’m so angry, or upset or triggered that I just can’t even listen, so would you be able to listen to me first, and if not, I’m going to need some time. Let me go and cool down and come back to you when I’m feeling calmer. Someone gave me a great analogy. It’s like you’ve got walkie-talkies. You can’t both talk on a walkie-talkie at the same time. It does not work. You have to take turns so if only one person has charge in the interaction, you’re fine. Because the other person hopefully will have the space to listen and navigate through it. But if both of you have so much charge then you have to agree to take turns. And if you can’t, then you’re going to have to go and run off that charge and come back.

Ben Jones – We hope this framework helps you take a fresh look at the way you approach tough conversations. Keep in mind these discussions are often just as daunting for the person on the other side of the table, and as such, preparation goes a long way in creating a better outcome. Check out the CARE model worksheet by visiting our show notes page, where you’ll be able to find a link to David’s website, as well. Now we’re going to let David wrap things up by reiterating the power of positive intent and transparency in the process.  

David Wood – The tough conversation seems like a murky fog. All you know is you don’t feel good about what happened. But when you do the worksheet, it will start to clarify everything. How could the conversation go well? That’s something the mind won’t often produce for you, without someone asking you the question, even a worksheet. You now have to now generate a positive outcome. Oh we could be on the same page. I could do a better job for you. I could feel more connected with you. We’re creating a positive intent that the other person can hear and go oh, all right, you’re on my side. And then what am I afraid of? How could it go wrong? That’s really important to bring that into the light. I’m afraid that this person will call me oversensitive. Or I’m afraid Jenny’s going to get defensive. That’s good. Once you know all that that’s wonderful information that you can bring into the conversation. Hey I noticed that was a big concern about bringing it up because I’m afraid of X happening. But I decided to bring it up with you, because my hope is that this will happen. That is a ninja formula. There’s something I haven’t been saying because and you insert your fear, but I’ve decided to bring it up because you insert your hope. That does about six powerful things within the space of 20 seconds. And then you end it with do you have 10 minutes.  

Ben Jones – Thank you for listening to Better conversations. Better outcomes. This podcast is presented by BMO Global Asset Management. To access the resources discussed in today’s show, please visit us at www.bmogam.com/betterconversations. 

Emily Larsen – We love feedback and would love to hear what you thought about today’s episode. You can send an e-mail to [email protected] 

Ben Jones – We really respond. 

Emily Larsen – We do! 

Ben Jones – If you thought of someone during today’s episode, we would be flattered if you would take a moment and share this podcast with them.  You can listen and subscribe to our show on Apple Podcasts, or whatever your favorite podcast platform is, and of course, we would greatly appreciate it if you would take a moment to review us on that app.  Our podcasts and resources are supported by a very talented team of dedicated professionals at BMO including Pat Bordak, and Derek Devereaux.  The show is edited and produced by Jonah Geil-Neufeld and Sam Peers Nitzberg of Puddle Creative.  These are the real people that make the show happen, so thank you, and until next time, I’m Ben Jones.

Emily Larsen – And I’m Emily Larsen. From all of us at BMO Global Asset Management, hoping you have a productive and wonderful week. 

Disclosure – The views expressed here are those of the participants, and not those of BMO Global Asset Management, its affiliates, or subsidiaries. This is not intended to serve as a complete analysis of every material fact regarding any company, industry, strategy or security. This presentation may contain forward looking statements. Investors are cautioned to not place undue reliance on such statements as actual results could vary. This presentation is for general information purposes only, and does not constitute investment, legal, or tax advice and is not intended as an endorsement of any specific investment product, security or service. Individual investors are to consult with an investment, legal, and/or tax professional about their personal situation. Past performance is not indicative of future results. BMO Global Asset Management is the brand name for various affiliated entities of BMO Financial Group that provide investment management and trust and custody services. BMO Financial Group is a service mark of Bank of Montreal. Further information can be found at www.bmogam.com.

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