Episode 206

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There are people who are considered leaders because their title says they are and then there are people who lead, no matter where in the org chart they may be. Agency owners can’t afford to be leaders in title only. We have to step into true leadership if we want our agency to thrive and grow.

David Wood, founder of Play For Real, is my guest on this episode of Build a Better Agency. David is a pro at spotting what it takes to be a strong leader in the workplace.

David was a former consulting actuary to Fortune 100 companies like Sony Music and Procter & Gamble. When he left his Park Avenue job, he began to explore the world in a different way in terms of helping high-performing entrepreneurs, executives and leaders play the game of personal development as well as it can be played.

In this episode of the Build a Better Agency podcast, David and I talk about what it means to show up as a leader who is not afraid to be daring, authentic, and vulnerable. We talk shop on how to encourage employees to be better leaders, how to build an environment of trust, and how true leadership can make all the difference.

A big thank you to our podcast’s presenting sponsor, White Label IQ. They’re an amazing resource for agencies who want to outsource their design, dev or PPC work at wholesale prices. Check out their special offer (10 free hours!) for podcast listeners here: https://www.whitelabeliq.com/ami/

What You Will Learn in this Episode:

  • Ideal traits and practices for leading people
  • The differences between relational and posturing leadership
  • How to recognize leadership flaws and train employees to keep you accountable
  • The importance of incentivizing employee contributions and collaboration
  • What being an authentic and daring leader looks like
  • How your leadership skills translate directly to running a more profitable agency
  • The power of listening to people’s problems rather than giving advice or trying to fix them
  • Action steps for becoming a more vulnerable leader

The Golden Nuggets:

“The best leaders now are the ones that have the right questions.” - David Wood Share on X “If I, as a leader, am willing to embrace more discomfort, then my team is going to be willing to embrace more discomfort.” - David Wood Share on X “As your team works better and produces more, your company will grow and make more money.” - David Wood Share on X “It takes incredible courage to be an authentic and daring leader.” - David Wood Share on X “Companies are wanting everybody to be a leader. Don't wait for me. You create what's happening now.” - David Wood Share on X

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Announcer:

If you’re going to take the risk of running an agency, shouldn’t you get the benefits too? Welcome to Agency Management Institute’s Build a Better Agency Podcast presented by White Label IQ. Tune in every week for insights on how small to midsize agencies are surviving and thriving in today’s market. We’ll show you how to make more money and keep more of what you make. We want to help you build an agency that is sustainable, scalable, and if you want down the road sellable. With 25-plus years of experience as both an agency owner and agency consultant, please welcome your host, Drew McLellan.

Drew McLellan:

Hey there everybody, Drew McLellan here with another episode of Build a Better Agency. Today’s topic is one that is pretty near and dear to my heart, the whole idea of us becoming better leaders, us learning more about our own style, our own weaknesses our own strengths and the way other people do it. Other best practices around how agency owners and leaders step into that role. I think we take for granted how often we lead. I think we lead multiple times every single day. I think we lead in small ways, in subtle ways.

Obviously, there are times when we have to storm in and lead in big ways and lead everybody out through a storm. But I honestly think it’s the deposits that you make in the ordinary moments. What I would call sort of tiny little moments of leadership, where when you do those well, then when everything hits the fan and you need everyone to follow you without any discussion, debate, argument, heel-digging, any of that, when you’ve put a lot in the bank, I think that’s when your team just steps in line and follows because you’ve earned their trust, you’ve earned their confidence. They know if you are taking charge in that way, it’s something important and it’s their job to support the team and support you.

So, I don’t care if you’ve been doing this for a day or a few decades. I think we all have a little room to grow. I know I certainly do. And that’s why I invited this week’s guest to be on the show. So let me tell you a little bit about David Wood. So, David has an interesting background. He was a former consulting actuary to Fortune 100 companies like Sony Music and Procter & Gamble. And he left his Park Avenue job and he began to explore the world in a different way in terms of helping people who are high performers and typically high performing entrepreneurs, executives and leaders play the game as well as it can be played.

So, to really live a regret-free life, to lead with boldness and with daring, but also with understanding who you are and being willing to be vulnerable in all of that. So, he has coached thousands of hours in dozens of countries all around the globe, and he is the author of a book called Get Paid For Who You Are. And Jack Canfield from the Chicken Soup fame actually wrote the foreword to that book. So anyway, David’s a fascinating guy, really believes in that all of us have the opportunity to what he says play for real. And I think that’s something we should all aspire to. So, I’m going to pick his brain on our behalf. Let’s do it. David, welcome to the podcast. Thanks for joining us.

David Wood:

Thanks, Drew.

Drew McLellan:

So, give the listeners a little background on how you came to be an authority on real leadership.

David Wood:

I looked into this word leadership over the past year and I’ve been really looking at myself like, “Do I know leadership? Do I understand it? Because I haven’t led 1,000 people. I haven’t led men or women into battle.” So, I was looking at, and I realized that we all have the opportunity to lead or not every day in our life. So, I realized that I lead myself. I lead my clients every time we have a coaching session. I lead people when I have an audience say of 1,000 people, I lead them in an experience. And I’ve been studying for 20 years, the principles of what I like to call inside out leadership. So, if you’re looking for someone who can help you lead 20,000 people and affect organizational change at that level, that’s not my thing. But if you’re looking for someone who can help you realize where you’re not willing to be vulnerable, where you’re not willing to be daring with people, where you’re not appreciating and acknowledging yourself and your team, then that’s what I’ve been studying for 20 years.

Drew McLellan:

So, let’s talk a little bit about, so in a lot of your writings and a lot of your teachings, I know in your coaching and the things that you’ve written, you use a lot of words like truth, daring, vulnerability. Talk a little bit about, because I think for a lot of people listening and I don’t think anybody listening is leading a pack of 20,000 people into battle. I think a lot of people are leading 10 people, 20 people, 100 people-sized teams and also teaching other people how to lead, because when you own an agency, most people who own an agency grew up in some aspect of the agency. So they were either on the creative side or the account service side. So they’re probably better suited to lead in that world because it’s kind of their sweet spot. But one of the reality is one of the, I guess, things you have to accept as an agency and I know I did a long time ago is that in many cases, I’m leading people who are doing things that I don’t know how to do it.

So, I can lead them in terms of the organization, but I can’t sit down at their computer and replicate their talent or skills because I don’t have it, right?

David Wood:

Yeah.

Drew McLellan:

So, let’s talk a little bit about this whole idea of truth and daring and caring and vulnerability and how all of that plays into leadership?

David Wood:

Great question. And I want to touch on something that you said and speak to it. Leading people and things that you don’t know how to do, I think there’s a shift that’s happening in corporations generally where it used to be, “I know how to do it and I’m going to show you how to do it. I’m going to have the answer.” “I am successful. Look at me, I’m a king, not a kingmaker.”

Drew McLellan:

Right.

David Wood:

And the shift seems to be towards the best leaders now are the ones that have the right questions. They’re the ones that have curiosity and to speak your question, they’re the ones that have the vulnerability to say, “I don’t know, you’re better at this than I am. You showing me how to do it.”

Drew McLellan:

Yeah. Well, and I think that ties brilliantly into what makes us good agency people. The best agency people may or may not have the answer, but they always have great questions.

David Wood:

Yeah. Yeah. And where truth comes into it, there’s one example. Truth could come into it with, I don’t know how to do this or even better, I think I know how to do this better than everybody else and I realize that’s probably not accurate.

Drew McLellan:

Right.

David Wood:

Oh, let me try some humility. Where truth also comes into leadership is let’s go back now. I learned to hide a lot of myself. I learned to hide if I don’t know how to do it. I learned to hide if I’m feeling scared. I learned to hide if I’m feeling lonely. This was just natural for me. No one actually taught me this is how you do it, other people role-modeled it and I got to hide that. So, the idea of truth, the idea of firstly, me realizing what’s happening in me, me realizing, “Oh my belly’s tense,” as you speak. I notice I’m tensing up. That was alien to me. So, if we start to explore truth, we can start to notice firstly, what’s happening in ourselves and how this affects leadership as an example, let’s suppose you’re running a meeting and you don’t know what’s next, but you keep talking. I call that posturing.

Drew McLellan:

Right.

David Wood:

You’re overriding what’s happening and I say people are going to feel it. And it’s going to impact your credibility and trust. Whereas if you bring in truth and reveal your own experience to yourself, you discover, “Wait a minute. I just realized I don’t know what’s next. So I’m going to put it out to the room. What do you guys think would be the next step here?” Now that’s truth. I just felt like some energy running through my arms as I said that. That’s truth and now you’re related. So now we’re starting to talk about relational leadership where you reveal your experience to yourself and then perhaps to others using discernment. And then that creates an environment where they can reveal their own experience to you and truth starts to be pinging back and forth. And now you’ve got relational leadership instead of some kind of posturing leadership. “Look at me, I beat my chest. I’ve got it. I’m going to take us all to success.”

Drew McLellan:

Well, I also think that falls into alignment. So, I’m in my mid-fifties and so when I think about some of my early bosses, they were more of what you were describing, which is they sort of just told you what to do and you did it. And then you’d sort of learned on the side and I even think about parenting styles and how that’s changed. And it used to be kids were seen and never heard, and now there’s a whole different dynamic in parenting. But I also think about the workforce that we have today. And I think about that sort of more dictatorial style of leadership. And I can’t imagine that would go well, but if you are my age and you’re running an agency, and so you grew up with that model of leadership, how do you learn how to be willing and what vulnerability looks like, for example. How do you learn how to be a different kind of leader than the leader examples that you grew up with in your career?

David Wood:

Yeah. Well, what comes to me as I hear the question is you got to catch yourself. I’m trying to do it myself. These things are easier to teach than to practice sometimes. And I found my assistant sent me a message yesterday. I said, “Rebook the call under any Friday, Thursday or Monday.” That seemed pretty clear to me. And she sent back a question, “Okay, you’ve got space next Monday. I just want to check that this time works for you.” And I’m thinking, “Why are you slowing me down?”

Drew McLellan:

Right, right.

David Wood:

What was not clear about that? Why do we have to go through another cycle? I got frustrated. And I sent her the question, I said, “I’m really in mystery as to why you would do that, but I wasn’t actually asking.”

Drew McLellan:

Right.

David Wood:

The subtext was, “You’re stupid. Don’t do that again.” And I was expressing frustration. Turned out she had a really good reason. I’ve got an extra calendar that she’s not sure that she’s seen. So Monday could have been full. So, I felt a little embarrassed and I realized, “I really need to practice curiosity and catch myself when I’m being arrogant. I’m so directive. I think I’m so smart.” I’m telling you, I’m not role-playing here. I really think I’m smarter than almost everybody on me. And that holds me back because when I’m creating a new system, like right now, I’m creating a system for social media management. An interview like this, I want my assistant to chop it up into really golden nuggets and create articles for it and image quotes, and put it out on social media.

Drew McLellan:

Right.

David Wood:

That’s a complex system. And I want to like, “All right, I think this is the best way to do it. Let’s do it.” I’m catching myself. As I’m thinking it, I catch it and I go, “All right, this is what I’m thinking. I want some pushback here.” I am… Oh, okay, I just realized, as I got this insight, I realized I can share it with her. Let her know I am directive. I will often say, “Let’s do it this way.” I need you to push back and say, “Hey, can I push back?” So, that’s how I catch myself.

Drew McLellan:

In the example you gave with the calendar, when you realized that the way you asked the question, which is, “Why are we going through another round? I told you it was okay to book on any Monday, Thursday, or Friday.” When you caught yourself doing that and you realized that you were kind of subtly saying, “Because you’re stupid.” Right? How do you fix that? Because I’m sure as we’re listening to this, I’m sure we’re all going. “Oh, okay. I kind of see myself in that description. Oh, yeah, I do that.” How do we fix it when we do it wrong?

David Wood:

Wow. So many things came to me at once. When you said it. The first thing, I think what I said to her was, “That makes total sense, my bad.” Something like that. That simple. But what I’m seeing right now is if I’m really committed to curiosity, “Oh, this stings a bit. I feel like I got a scrunchy face.” Because I’m like, “Oh, I don’t want to do this.” Which tells me, this is a good thing to do. I can come clean and be transparent and practice truth. And so I commit now to doing this after this call and sharing this conversation with her and saying, “You know what? I just assumed that was a dumb move. Why would you do that? I was frustrated. I wasn’t curious. And I want to practice curiosity. If you notice me not practicing curiosity and being arrogant, I’m inviting you to call me out on it.” That’s how I can transform this old habit for myself is practicing truth, bringing it into the light of the day. And I’m blaming you for this ninja move that I’m about to do with my assistant.

Drew McLellan:

Sorry.

David Wood:

Thank you.

Drew McLellan:

I have to think though, there are a lot of employees who we say, “You know what, when I do this thing, I want you to call me out on it.” And the employee nods their head and inside their head, they’re going, “Oh, no. No, no, no, no, no. I am not going to call you out on that. I’m going to pretend that I will, but I don’t feel safe doing that.” How do you make someone feel safe too? When you’re in a leadership role, when you control someone’s job or professional career path, I get that it’s tenuous to ask them to critique you. How do you actually make that safe?

David Wood:

So, I just realize it’s tempting for me to give an answer. Like this is the answer. This is how to do it. And I’m not going to speak that way because I’m acknowledging there are 1,000 answers. The answer that I have right now, and that I’m going to use with my assistant is to give her the language she can use. These words are what will probably get my attention. It’ll probably be something like, “Remember when you asked me to mention… To inquire if you’re practicing curiosity? Is this one of those times?” Something like that is something I can hear. So, I’ll give her the words that she can use. Otherwise, it might be hard for someone to come up with a way to challenge their boss even though they’ve been invited, it’s like, “[inaudible 00:16:18].” You’re not listening right now. That might not work, right? So, there’s one idea is give them the language to create that safe space.

And I love that you brought that up. She might have said, “Yeah, yeah. I know you’re saying that. I don’t want to poke the bear.”

Drew McLellan:

Right. Right. It’s interesting because many years ago… I’m super fortunate. So, not only do I own the Agency Management Institute, but I still own my own agency. And my, my tenure of staffers, they’ve been with me forever. So 17, 18 years on average.

David Wood:

Oh, wow.

Drew McLellan:

So, many years ago, one of the more braver of my team members said to me, “when we have bad news for you, you probably don’t realize it, but you have an expression on your face that says… No matter what’s coming out of your mouth, the expression on your face says, ‘I don’t want to hear those bad news, and I’m a little annoyed.’” And I was like, “Really?” And she was like, “Yeah, every time, which means that people don’t want to come and tell you stuff that you need to know.”

So, I pulled everybody together and I said, “Hey, here’s what I’ve been told.” And they all nodded their head at me and I was like, “Okay. So, it sounds like I need to get a better poker face, but I don’t always know when I’m supposed to have the poker face. So, what I would love for you to do is if you have bad news or something you think I’m going to react badly to, and you want me to just sort of catch my breath and not react. It would be awesome if you would walk into my office and say, ‘Hey, do you have time to have a difficult conversation?’ And the words difficult conversation will trigger me to put on my best poker face and know that I need to be slow to react and just hear you out so that it’s a safe place for you to talk to me.”

And so, we came to that agreement that they would try that. And I will tell you, it’s probably been over a decade since that happened. There are many times when they now stroll into my office and go, “Difficult conversation time?” And based on the frequency that it happens, I’m assuming that I’m getting better at it. So, to your point, giving somebody some language, a common language, like just a word that I get exactly what’s about to happen next so I can be prepared for it-

David Wood:

Yeah.

Drew McLellan:

… Makes sense. Yeah.

David Wood:

Well, I think you’re speaking now to a really powerful leadership move that everybody can use in their life and their business, which is setting context.

Drew McLellan:

Right.

David Wood:

And then what you did is you kind of went meta and you set context for them to set context with you, but let’s pause on that for a moment. You’ve got a difficult conversation with someone, you can just come in and dump it on them, right? Any kind of conversation with charge, or you can kind of prep them. Safeport is an amazing word. You can safeport them, let them know what’s coming. “Hey, I got something that might be a little edgy to talk about it. You got 10 minutes to sit and talk about it?” The language that Brené Brown is using in her book, Dare to Lead is rumble. Let’s rumble with some vulnerability. And so, people are starting to learn in some cultures, rumble means what you said, slowing down, giving each other space. There’re going to be feelings, that might be uncomfortable, we’re going to do that. We’re going to rumble.

So, let’s all set context for those conversations in our life, which can be a game-changer as you probably experienced. And then what you did is a ninja black belt move showing them how they can set context for you.

Drew McLellan:

Right.

David Wood:

“If I’m not going to all listen, here’s what you can say, so you can put me in a space of listening.” So you kind of lead them into their own leadership move? I like how you did that.

Drew McLellan:

Yeah. They lead on a regular basis, which is great for me and for our clients, absolutely.

David Wood:

Well, that’s another shift that’s happening. I talked about the shift from, I know to I want to know. And then this other shift is this idea that companies are wanting everybody to be a leader. “Don’t wait for me. You create what’s happening now.” And I love personal agency, so I’m all on board with that.

Drew McLellan:

Well, and that’s a necessity in today’s agency. When you’ve got account people who are sitti