516: Making Difficult Conversations Easier with David Wood

Pete Mockaitis
David, thanks for joining us here on How to be Awesome at Your Job.

David Wood
Hey, my pleasure.

Pete Mockaitis
Well, I’d love to kick it off if you could share an interesting story about some of your work with people in prison.

David Wood
Well, I’m moved by their stories, and I’m particularly moved by some of the tough conversations that they need to have. There’s one inmate who we interviewed. We took in a film crew and we interviewed her, and she was part of a robbery. She didn’t actually do the robbery but she conspired to plan the robbery, and they didn’t follow the plan. They did something else, and someone got shot and killed. So, she got sentenced to 25 years in prison for planning a robbery whose plan wasn’t followed.

And one of the toughest conversations of her life that was coming up when I spoke to her, and I haven’t spoken to her since she had it, was she said, “How do you explain to the widow of your victim how sorry you are? How do you say ‘I understand that your kids are now suicidal, and you’ve lost your husband, and it was all because of something that I set in motion’? How do you explain how sorry you are?” And I didn’t really have any answer for that. So, that’s one story I’m moved by. I’m moved by many of the inmates and what they’re facing on a daily basis.

Pete Mockaitis
I’m intrigued. And so, in terms of your life’s work and expertise, what is it that you think that causes you to return this population again and again?

David Wood
I keep wondering why I go back into prison. I think, initially, it was a fascination with confronting my own freedom because I think that we take so many things for granted, and I wanted to see what was it like to go in and serve this underprivileged population. And then when I got in there, I found out how grateful they were. They were really humble, and they were really listening. They wanted to learn, “How am I going to communicate with a potential employer? How am I going to handle tough conversations with my family while I’m in prison and then when I get out since they’re blaming me for everything that’s gone wrong?”

So, they’re listening, and they want to know. And when we leave there, they’re just so grateful. They said, “A lot of people won’t come and spend the time with us. Thank you so much.” So, it gives me a chance. A lot in my life is going really well and it gives me a chance to do some service.

Pete Mockaitis
Oh, can you zoom out a little bit? I want to hear a little bit about your philosophy and organization, play for real, what does it mean?

David Wood
Well, I believe we’re playing a game. I know not everybody has that viewpoint but I think life is the greatest game there is and the stakes are very high. Literally, we can die. So, the stakes don’t get much higher than that. But if you don’t know that you’re playing a game, what can happen, let’s say in your job, you can get tense, you can start to feel overwhelmed, you can start to get a bit crabby and snap at people because, now, you’re stressed and you’ve forgotten that you’re playing a game. So, I’d like everybody to be able to tap into the flow of life by remembering this is a very high-stakes game.

But I don’t mean we’re being frivolous about it and we’re just, say, dancing through the daisies with butterflies floating around our hair and not a care in the world. I’m saying, let’s play the game but let’s play it like we mean it. Let’s play it as if we may not get another chance to be reincarnated and live a second life. Let’s play but let’s play for real. So, to me, that means let’s try and live so that on our deathbed we will have zero regrets and say we absolutely gave our job and our relationships and our life everything that we possibly could.

Pete Mockaitis
That’s powerful. And so, we’re going to spend most of our time talking about how real conversations are difficult conversations play into it. But just to get oriented to the broad picture, you lay out four particular obstacles or enemies of playing for real. So what are those if you can give us the quick version for how we overcome those?

David Wood
Yeah. So, one thing that people are missing is real goals. They’re going through life but they haven’t actually set goals to light them up. So, that’d be the first thing that’s missing. The second thing, suppose you have goals, you know where you’re heading, but not everybody sits down and creates a strategic plan, and says, “This is exactly what needs to happen for me to achieve those goals.” So, we’re just talking about a lack of a strategic plan.

The third one is there’s no real action. It’s one thing to have a plan, it’s another thing to implement the damn plan. So many of us get distracted by Facebook messages and text messages and people coming and knocking on the door that we don’t actually take action on the things that we say matter. So, lack of real action is the third one.

And then the fourth one is lack of real growth. And I’ve identified three values that I found critical to up-leveling in life and business, and that’s increasing your truth, increasing your levels of daring, and increasing your levels of caring. So, by addressing these four, we can actually create real goals, we can create a real plan, we can get in real action. And by increasing levels of truth, daring, and caring, we can actually have real growth in our life. And if you follow all four of those, then I say that leads to a regret-free life.

Pete Mockaitis
And I think that makes a lot of sense to me in terms of, yeah, I can see those four things need to be in place to move toward really cool stuff that matters. And if we increase the truth and daring, that’s going to certainly help you out there. Now, I guess I have a bit of a picture or assumption on how daring and caring apply and how they’re special. But could you expand upon increasing truth? What does that mean and how is it done?

David Wood
Right. Well, let’s say, this is about being awesome at your job, right? So, if you want to be awesome at your job, let’s look at how you can increase your levels of truth. Now, if you’re not speaking up and talking about something that doesn’t work for you, then you’re hurting yourself and you’re hurting the team. So, let’s say Bill, over in accounting, is doing something that’s actually slowing down your job, and you stay silent. Well, that doesn’t really help anybody. So, by increasing our levels of truth, we can start to speak up about what I need, about what the team needs, and about what the company needs. It might be that you need a pay raise, and so while you’re sharing that with your boss, you’re increasing your level of truth.

And I actually have a secret mission. I want everybody in the world to increase their levels of personal responsibility, increase their levels of agency so that we’re speaking up and we’re causing the matter instead of just being passive or, even worse, complaining or gossiping. So, that’s an example of how we might increase truth.

Now, to increase daring, I think you can start to see how it goes hand in hand. For you to speak up and be the squeaky wheel at work, it might take some courage to go to your boss and say, “May I have more money?” or, “Can I get a transfer to this environment?” or, “Hey, I think I’m being discriminated against sexually in the workplace.” All of these things take daring to speak up. Also, it’s daring to say, “Can I have that Japanese account?” or to say to a prospective customer, “How about you sign up for a year instead of one month?” So, those are just some examples of the daring.

And then caring, you can care for your fellow workmates and actually care that they do a good job, and that they’re doing well, and that they’re feeling appreciated. You can care for your direct reports. You can care for the relationships between you and your customers. You can care for your personal relationships and nurture your relationship with your kids, with your parents, with your spouse, and you can also practice self-care, because burnout’s becoming a bigger and bigger problem in the workplace. And if we’re not taking care of our nutrition, and our rest, and our exercise, then, eventually, we are going to burn out and it’s going to whack us with a big stick.

So, does that answer your question of, “How do we increase levels of truth, caring, and caring?”

Pete Mockaitis
Yes, so I’ve got a broad picture for how that unfolds there. So, now, yeah, let’s just talk, when it comes to pulling all that and you’ve got some conversations that are tricky, I mean, for starters… I made this more philosophical. Let’s see how it goes. What makes a difficult conversation difficult in the first place?

David Wood
Fear of loss. We’re usually worried about losing something. So, a difficult conversation at work would be, again, “May I have a pay raise?” We might be worried about annoying our boss and getting cut out of the next project, or maybe the boss says, “You know, we really don’t have the budget to support your salary, and you’ve just reminded me. You’re fired.” Or, let’s suppose, with our partner, a really tough conversation can be a confession, “Hey, I kissed someone and broke an agreement three years ago, and I want to come clean about it.” We could lose that relationship. So, fear of loss is one of the biggest things that make something a tough conversation.

The other thing, which I think is linked to this, is vulnerability. We can’t control a tough conversation. We can’t control the other person’s reaction if they get upset, if they get defensive, we can’t control what they do. We can’t even control how the conversation goes so we’re stepping into vulnerability to have a tough conversation. And I can understand why a lot of people might want to just sweep that under the carpet.

Pete Mockaitis
Okay, so that’s why it’s sort of tricky. So, then how do we go about having these conversations effectively?

David Wood
Well, I have a four-step blueprint. And, by the way, tough conversations, I’ve been interested in those for 10 years in helping my clients, but I only recently, but I realized how well they fit into truth, daring, and caring because it’s all about telling the truth. It takes a lot of daring to have a tough conversation, and it takes a lot of caring to do it right. So, I’ve been very excited when I realized, “Oh, this is a way I can express truth, daring, and caring in the world and one the ways that we can play for real.”

So, how we do it, as I have a four-step blueprint, and if you like, we can give listeners a download at the end of this so that they don’t have write down a whole bunch of notes.

Pete Mockaitis
Oh, sure. Let’s do that too. So, okay, four steps.

David Wood
Yeah, four steps. And if you like, we can use an example with an authority figure. So, it could be something that you want to say to your boss, or we had an example with one of the prison inmates, and she was saying, “When the guard was late to his shift, that meant that I couldn’t be where I needed to be in the prison, and I got chewed up by another guard, and it really impacted my life.” And she said, “How do I have that tough conversation with an authority figure who has the ability to make my life hell?” And anyone with a job knows that their boss has a lot of power over them financially, their work hours, a whole bunch of things. So, we can use that as an example perhaps.

Step one is you ask permission for the conversation. Don’t just launch into it. So, with this prison inmate, for example, she could say to the guard, “Excuse me, Mr. Smith, do you have just a few minutes for a quick conversation?” And this is a good point to share your hope for the conversation, and we’ll give listeners a worksheet as well. When they download the four-step worksheet blueprint as a worksheet so you can prepare for this, and that’s where you work out your hope.

Now, her hope was, “My hope is you can understand a little more about what it’s like to be an inmate and that, hopefully, that might influence some of your decisions in the future,” something like that. Or, “My hope is that my life might be a little bit easier if you understand a bit more what it’s like.”

And then, step two, this is where you can share your fear or concern. Now, I guarantee there’s a fear or concern or you wouldn’t be calling it a tough conversation. So, in her example, “I’m hesitant to bring this up because I don’t want to offend you. You might feel offended or defensive and you might not want to listen to me, and I might get in trouble.”

And then, step three, this is where you share the issue. And if you have a request from your worksheet, this is where you put it in the request. So, in her example, again, it might be something like, “When you were late, I got in a lot of trouble. I got chewed out and I couldn’t pick up my property, and it really had an impact. And my request is, to whatever extent you’re able to, if you could try and be on time, then I’d be really grateful.”

And then, step four, the last one, I think can be the most important. This is where you get curious and you listen and negotiate. We don’t want to have tough monologues. We want to have tough conversations. And this is also where caring comes in. So, it might look, in this example, something like, “I’m wondering how is it for you to hear that? Does that make sense? Does that sound workable? Do you have a better idea? I’d love to hear anything you’ve got to say,” because you don’t want to just dump this and then run. And you may find out, she may find that this corrections officer may have a better idea than she had. The corrections officer may be like, “Look, I’ll speak to the other CO and I’ll smooth things over for you,” or, “I can’t guarantee I’ll be on time but I’ll help you out if you get in trouble because of it.” We don’t know. But that’s the plan.

Step four is get curious, and then we listen and negotiate.

Pete Mockaitis
Okay, yes. I like that. It makes sense. It’s handy when you sort of have, I don’t know, a preamble but you share those bits in advance. And I think it makes them more kind of sympathetic or appreciative that you’re a human being and you have some sensitivities and vulnerabilities and you’re not trying to attack them.

David Wood
Yes, that’s right. It’s relational and it’s vulnerable. It’s like, “Here’s my hope out of this, here’s my fear or concern out of this, I’m a real person. I’m kind of at my edge here.” It changes the whole space. And people are more, I find, they’re more likely to listen when you show a bit of vulnerability and let them know the context of what’s going on instead of just you working it out in your head, and then launching into a tough monologue trying to get what you want.

Pete Mockaitis
Okay. Well, let’s do another scenario here and I think this happens a lot at workplaces. Okay. Let’s say you are responsible for your project to get done and that has any number of dependencies from other departments which you don’t have really control or authority over those folks who need to provide key stuff or inputs for you to get the job done. And so you’ve got to do some of those prompts, like, “Hey, you didn’t give me your stuff when I needed it.” But I always found that tricky in environments, in terms of, “How do I do an appropriate follow-up and what are the prompts I should be using to get what I need without being sort of offensive or pestering?” Because I don’t want them to think like, “Who’s this guy and why is he always in my business pestering me non-stop?” So, yeah, there’s the scenario. Let’s walk through how’d you approach such conversations.

David Wood
Perfect example and very similar to this inmate who wanted something from someone else who had some authority, she couldn’t control it so it was really a request. And in giving that preamble, I think you’ve given all the answers we need. So, first step would be asking permission, right? We’re not going to dump it on someone. We’re going to say, “Hey, if you’ve got a few minutes to talk about this project,” and this is where you’ll sweep in your hope, “My hope is we can be more in sync as a team and to be honest that I’m going to look even better with my boss,” for example, right? I’m making that up, “But I probably want to look good with my boss. So, that’s my hope.”

“And then my fear, or my concern about bringing it up is I know you don’t report to me, I know it’s not your job to make me look good, and I don’t want to be too obnoxious. I don’t want to be stepping on your toes, and I don’t want to put you offside, so I’m a little hesitant to bring it up, but I think it’s worth talking about.” So, now, we’ve been real, we’ve shared a hope, we’ve shared a concern.

And then, step three, share the issue and include a request if you have one, “So, the issue is I would share the impact. When I get the material later than you said it’s coming, there’s a whole pipeline that gets messed up, and it ends up taking us longer, and then sometimes I get in trouble for it. That’s the impact. And so, my request is that if we can be more rigorous around our deadlines, and if you don’t think you can get it to me by Thursday, give me a firmer deadline of Monday. But if you say Thursday at 5:00 o’clock, my request is that we be a bit more rigorous with it. Do you think that would work?”

And now I’m already going to slip straight into number four, “What do you think about this? Have you got any other ideas? Because this isn’t quite working and I’d really like to find something that does work.”

Pete Mockaitis
And so, defensiveness pops during the course of the conversation. Do you have some pro tips for navigating that?

David Wood
Yeah. And I like what you said, like, “I don’t want to be obnoxious. I don’t want to be nagging all the time.” So, I’ll share that concern and I’ll say, “How do I request things from you without being a nag? How do I do it? Do you have a suggestion for language? I’d really like your ideas on this because I’m a little bit stumped.” And then you work it out together.

Pete Mockaitis
Okay, sure. Now, can we talk about going first. I’ve got Stephen Covey in my head here now. You know, “Seek first to understand then be understood.” How do you think about that sequencing or timing of who’s going first, and when is it optimal?

David Wood
Yeah, yeah, great. I love that. So, in the download, you’ll get some pro tips. And one of the tips is if you find that the other person is not really listening, they’re just jumping in, so you say something like, “You know, if I get the things later than we said, then I said, ‘Oh, well, my boss was doing this, and blah, blah, blah,’” they’re not listening, then you could try some words like this, “Hey, I want to hear that, and I want to try and get this out in one go. Do you think you could give me just two minutes? And I think I can cover all the bases. And then I’d love to hear everything you’ve got to say. So, we’ll just take turns then. Is it okay if I go first?”

And if it’s not, “Okay, maybe you go first and I’ll listen first. I’m okay with that.” The main thing is that you take turns and that there’s actually a two-way communication instead of someone just getting triggered and kind of running the show. If that happens, make the request, “Can I go first? And if not, you go first.”

Can you say the question again about the sequence of timing?

Pete Mockaitis
Oh, sure. So, we talked about, “Can I go first?” and I’m thinking about Stephen Covey with one of those seven habits of seek first to understand then be understood. So how do you think about the timing, sequencing of who goes first, talking versus listening. And are there particular circumstances in which you recommend listening first or just how do you think about that?

David Wood
Well, I think it’s sometimes a matter of charge, like, “Who has the charge?” So, if you’re the one that has some emotional charge on something, and you’re a bit at your edge, you might just want to request permission, “Can we talk about this? Can I share this issue?” And if you a yes, go for it. And then find out their reaction. So, I think it makes total sense for you to go first.

If you think that they might have a bit of charge, let’s say that you think they’re really upset with you about something, then you might say to them, “Look, I want to have a conversation about this and I can go first if you like, or if you like, you go first and I’ll listen, and then we’ll switch.” So, you’d still ask permission for the conversation, then you might throw it up in the air. Because if they’ve got a lot of charge, then the chances are higher they’re going to get triggered, angry, defensive, upset, something like that, and I might want to preempt it and let them, just hear their issue first.

But sometimes you’re taking something to someone where you don’t even know if they’ve got an issue, so I don’t think we have to artificially try and get their side first. I think it’s fine to just lead in and see if there’s permission for you to share your side.

Pete Mockaitis
I got you. Thank you. And then in terms of sort of managing in your own head and the emotions in the midst of these conversations, anything you recommend on how you can do that well? So if you’re starting to freak out, do you have some tips? Or if you’re feeling a little scared, nervous, anxious, and some things show up that you weren’t expecting… What do you do?

David Wood
I can see why you’ve got so many reviews on your podcast. You ask really good questions.

Pete Mockaitis
Well, thank you.

David Wood
So, yeah, we’re talking about some emotional regulation now. If you know that you’re going to have an issue, for example, I had a podcast host say, “How do I share with my mother who’s got Alzheimer’s and who’s dying? How do I share with her all the things that I’ve been disappointed about in my life? I want to have no secrets between my mother.” Now, that’s a tough conversation.

And one of the tips that I gave her was to talk it out first with a friend or even journal it. Like, get it out. Don’t take all your charge about your disappointment about how your mother raised you and dump it on your mother. Better to go through your worksheet, work out your hope, work out your fears, you might write down all your disappointments, talk them out with a friend, in this way you can release a lot of that emotional charge so that when you go into the live conversation, you can be more matter of fact and deal with the facts, say, “Yeah, I was disappointed about a few things. Here are a couple of the key ones. And now that I’ve talked it out with a friend, I’ve realized that you’re actually doing the best you could.”

Those kinds of insights can come out of doing this. And I’ve also, I had one client who’s a manager in a tech company, and she said, “I’m worried about this tough conversation with my staff. They’re going to give me feedback on my management style. What if I get triggered? What if I get defensive and shut down?” Which is a super smart thing to be aware of. So, I said, “Great. We’re going to practice it. I’m going to be your employee, and I’m going to give you feedback, and I’m not going to go very easy on you, and we’re going to see how you go.” So, she got to roleplay it. And I started easy, just with a few things, and she handled it really well. And then, finally, I said, “You know, basically, you’re just clueless.” And that was too much.

So, we found her edge and she shut down, and then we slowed down, and we worked through it, found out why she would shut down, and she learned a new language. She learned how to say, “Ouch! That hurt,” instead of pretending and covering it up. So, long answer to a short powerful question, you can roleplay it, and you can talk it out with your friends first to release a lot of that charge so that you’ll be more settled when you actually have it.

Pete Mockaitis
Oh, that is good. And while we’re talking about feedback and being on the other end of some of this, are there other perspectives in terms of, how can we be open to the feedback and encourage and receive it and put it to use all the more often?

David Wood
Well, one way, this might seem flippant, but one way that we can get good feedback more often is to listen to the feedback we get. Now, I’ll put myself up and confess straight away that this isn’t automatic for me. If someone says something that I receive as critical, my first thought might be to defend, “Well, the reason that happened was blah, blah, blah.” I’m not listening. I’m not listening to their experience. So, if you can catch yourself, you go, “Oh, wait a minute. I just reacted to that. Let me slow down and listen to this. All right, you’re saying when I deliver this late, it has an impact on you and you get in trouble with your boss. All right. So, what I need to do is to be better about managing my deadlines.”

Now, if I’m willing to actually listen to someone’s woe instead of just defending myself, they’re more likely to come to me next time and say, “Hey, you know that conversation went well. How about this one? Would you be willing to try this?” But how many people do you know at work who just, historically, have not been open to requests, or criticism, or feedback that’s less than glowing. I know people that I’m not going to give them any feedback because they’re bumpy and they’re just not open to it so I stop giving it to them.

Pete Mockaitis
Totally, yeah.

David Wood
Yeah, I’ve got this manager I was just talking about, she wants feedback. She wants to be a great manager and she knows to be a great manager she’s got to know if there’s a problem so she’s gone to each of the team members and said, “Would you be willing to tell me if there’s something I’m doing that’s not the best?” And she told them a story about her boss. She told her boss, “What could I do better?” The boss said, “Oh, everything is good. Everything is good. No, you’re doing great.”

Pete Mockaitis
What happens?

David Wood
And then when it came to review time, the boss said, “Well, here are five things you could’ve done better.” And she was naturally pissed. She’s like, “I wanted that feedback. I could’ve been better already.” So, she told that story to her staff to let them know that she really does value feedback, and to model for them what it’s like to actually request for feedback so that some of them could go, “Oh, same here. Let me know if I can do something better.” A real ninja move to cause some of that.

Pete Mockaitis
Excellent. Well, David, tell me, anything else you want to make sure to mention before we shift gears and hear about your favorite things?

David Wood
Well, I like talking about my favorite things, so let’s shift gears.

Pete Mockaitis
All right, let’s do it. How about a favorite quote or something you find inspiring?

David Wood
Well, I’m going to quote myself because I said something a couple months ago and it stuck with me, and it feels so core to the work I’m doing. And what I said was, “The tough conversations we haven’t had form the boundaries of our world.” They literally form the boundaries of our reality. But the tough conversations we do have become the defining moments of our relationships, our career, and our lives.

Pete Mockaitis
And how about a favorite study, or experiment, or bit of research?

David Wood
A favorite bit of research? Well, there’s an assistant professor on the East Coast of the U.S. who surveyed, I think, it was 150 hospice nurses to find out what people actually regret on their deathbed. You hear so much talk about, “Oh, on your deathbed, people wished they hadn’t spent so much time at the office, blah, blah, blah.” But where’s the research? Well, I’m telling you, there isn’t any. This guy has got the closest piece of research, it’s very hard to get to the actual people dying due to privacy laws and permissions at the hospital and family and all these things. I’ve tried. But he actually researched the nurses and found, say, the top five regrets of the dying. So, that’s one of my favorite pieces of research just because it’s the closest that exists to what I really want to see which is actually asking those who are dying.

Pete Mockaitis
And for those who haven’t seen the study, could you share a couple of them?

David Wood
Oh, being true to one’s self, that’s one. And I may not have the words right but being true to one’s self, speaking up for you instead of living other people’s dreams, that’s one. And I think an example of that would be telling people how much you love them.

And I can relate to that. When I imagine being on my deathbed, there’s a scan, and I’ve been near death. I’ve been sitting on a plane with the engine caught on fire, I’ve had my parachute collapse and head plummets towards the ground, and I’ve scanned, “Is there anything left? Is there anything left unsaid?” In fact, I turned to my partner, with the engine on fire, and said, “Well, good, Ray. Is there anything we haven’t said?” And we agreed we were solid. I want that experience for everybody, that you don’t die with anything left unsaid.

Pete Mockaitis
And how about a favorite book?

David Wood
I’m a fan of The Work of Byron Katie. And so, I’m going to mention Loving What Is because it was my first introduction. I didn’t get a grasp for The Work from that book but it was what led me to go further with Katie and finally get a grasp on The Work. So, Loving What Is by Byron Katie will start to introduce you. This reminds me of a quote of hers which is one of my favorites, which is, “The worst thing that can happen to you is a thought.” Yeah, a whole gamechanger to start to realize that circumstances don’t give us our experiences of our life. It’s what we’re believing that gives us our experience of life. And Katie gives us a way to hack those painful thoughts to get to peace.

Pete Mockaitis
And is there a favorite tool you’d recommend to people to be more awesome at their jobs?

David Wood
Yeah, I recommend the four-step blueprint for tough conversations which we’ll give your listeners in a few minutes.

Pete Mockaitis
And a favorite habit?

David Wood
Ooh, I like something called somatic sequencing. It’s new. This is new for me. I’ve been running from a lot of the sensations in my body for years and years, and I believe this is what people pick up with cigarette, or they smoke, or they have a glass of wine. Or you take some medication to kind of numb ourselves, or watch TV. But I’ve been experimenting with a therapist in feeling the feelings. Like, I’ll go and lay down a special place in the house and I’ll be like, “What is happening in my body?” I’ll just feel it and I will try and welcome everything that’s happening. And that’s been a bit of a game changer for me. So, that’ll be my new favorite tool or practice.

Pete Mockaitis
And if folks want to learn more or get in touch, where would you point them?

David Wood
You can go to PlayForReal.life. At PlayForReal.life you can download the blueprint. If you are serious about up-leveling in career and life at the same time, then see if you qualify for a discovery session with me. If you do, I don’t charge for those sessions. And I have joined the ranks of the podcasters in the last week, Pete. And if you’d like to listen to me as well as Pete, then Tough Conversations with David Wood is a new podcast you can subscribe to, again, at PlayForReal.life.

Pete Mockaitis
Oh, cool. Well, David, it’s been a whole lot of fun. I wish you all the best and keep on doing the great work as you’re playing for real.

David Wood
Thanks, Pete. I appreciate you.