GROWTH PILLAR: Leadership & Ops
WHO THIS IS FOR: SMB owners / Solopreneurs / Team leaders / Anyone managing people or driving change
WHAT THEY'LL GAIN: A clear framework for identifying avoided conversations, practical tools for resetting stuck dialogue, and the confidence to have the hard talk before it becomes a bigger problem.
Most teams don't fail because of strategy. They fail because of conversations nobody had.
Steffan Surdek is a leadership coach and culture change expert who helps organizations close the gap between what leaders intend and what actually happens. In this East Trade Winds session, he introduces conversational debt, the accumulation of avoided conversations that quietly erode trust, accountability, and team performance over time.
Steffan breaks down why people avoid hard conversations, what stories they tell themselves to justify the delay, and why the right time is almost always right now. He walks through real examples, the employee who always arrives late, the kickoff event everyone forgets by Tuesday, the leadership meeting that goes in circles, and shows how each one is a symptom of unaddressed conversational debt.
He also shares a simple reset technique he has used with his own spouse for years: stopping a stuck conversation mid-stream, naming where both people are, and starting again from a cleaner place. It works in marriages. It works in boardrooms.
Key topics covered:
Connect with Steffan Surdek:
Free resource from Steffan — Five Key Skills of a Co-Creative Leader Handbook — a 10-page PDF with principles and a self-assessment. Worth grabbing.
Co-hosts: Percy Barr and Wayne Pratt
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Next Steps
Steffan (00:05)
I'm gonna talk about a topic here that I like to talk about called conversational debt and and conversations and organizations. And last time I did this was in April at an entrepreneur event in Montreal. I was speaking for them and the organizer was struggling that day with getting the projector working.
So I went to see him and I said, you know, if you can't get it to work, don't worry about it. I can wing the whole thing. No problem. And lo and behold, what do you think happened? He just couldn't get the projector to work. And when he introduced me, he said, Well, Steph said he could wing this. Let's see. So I went off for 30 minutes.
one of the big things I like to talk about inside with my clients is this notion of the missing conversations. I find that often inside organizations, we don't talk. There's a lot of things we don't talk about. They're either taboo topics, topics that we've spoken about so often, they've never led to anything. so we just stop having those conversations.
Sometimes we don't know the conversation is even possible. and this thing, this missing conversation that I like to talk about, I like to call conversational debt. So, conversational debt is all the conversations that you really should be having in s in your lives, whether it be your professional life, your personal life, and that you're just not having right now. So let me give you a very basic example, right?
Who here has has a spouse, a significant other? Raise your hand.
Who has at least one conversation with your spouse that you know you need to have, that you know you need to talk about, something you don't like, something they do that bothers you, something important that you need to bring up, and that you just never bring up. Are any of you here, or am I the only one? Right? We we all know this. We all know this. And you can have this with your kids, you can have this with anyone in your life, with with friends, etc. And I like
This notion of conversational debt, because when you think about it, when you don't talk about it, there's an impact. There's an impact to that debt. Right. And the next time that you're kind of close to the topic, you realize, I still can't talk about this. Your frustration goes up. There's something that happens where you feel as if, okay, it's getting, it's getting worse. Inside companies, how this looks is imagine
The person that always arrives late to the meeting. Have you have you had the one of those in your lives at one point? That person that they arrive late, five minutes late, every single time. And when you when you see them come in, everyone just groans. Right? You can see it. If even if you don't hear it, you can see it. Everyone goes, Darn, there's Sharon, right? And and what happens eventually? I'm picking on Sharon, I'll pick on the one.
On any of you at any given point here. But you know, essentially what happens is that the more that Sharon arrives late and no one brings it up, the more it becomes okay, maybe for someone else to start doing it. Right. And then all of a sudden, Bernie, who's supposed to run this call, just doesn't show up on time. And he's five minutes late for his, you know, East Trade Winds call. And it's like everyone's like, But but Bernie, you run this thing, right? And then it goes on and on. People.
You know, pe there's no accountability. So people feel, you know, okay to do the same thing and it promotes bad behaviors. And inside leadership teams, what happens is these accumulate over time. And you have a lot of them over time, these conversations that you haven't had, that you haven't that you don't know that you could have. Now the the question is why aren't we having these conversations? Any ideas?
Any ideas as to why we have this conversational debt going on?
I don't know how to have this conversation.
It's just a debt of conversations. It's these this bunch of conversations that have accumulated over time and that because you haven't had them, bad things are happening around you on your team, or bad things are happening with your spouse versus you know, I don't know if you've ever experienced this. I've seen this with with my spouse over time, where you know, there's conversations that I didn't know were possible.
And we're having an argument, and all of a sudden she takes a chance and she brings up a topic. And I'm like, wait, this this could be a conversation? Okay, cool. Let's talk about this, right? But I didn't have the con the courage to bring it up myself. So sometimes you know, we don't want rejection. We have a fear of of how the other person is going to react. And it's all stories that we tell ourselves to give ourselves permission not to do this.
That's what it is. We're looking for good excuses, right? So I have clients sometimes that will tell me they know they have a problem with an employee. And as they tell me the the the issue, I go, Well, have you spoken to them about it? I haven't found the right time yet.
When is the right time?
go and do it and figure it out. Right. And it's how you show up inside that conversation that allows things to happen or not happen. So what I do inside companies is I help them lead change. And when you're trying to create change, there's a lot of conversations that need to happen around change. there's conversations that you may have with your leadership team.
There's conversations you may need to have with the leaders inside the organization, people that aren't necessarily that don't necessarily have a leadership title, but they're the influencers on the floor. They're the people that can make a difference, that can influence others. And we avoid, you know, bringing these people in, getting them involved in the early stages of the conversation around what we want to do, what we want to bring in. And then we wonder why aren't people buying in?
Why aren't people doing what we need contributing to what we need to do? Doesn't anyone know what the goal is here? The classic example inside companies. I'm sure some of you have seen this one too. How many times have in your career have you seen the big kickoff event? You know, the big kickoff where we introduce the transformation and we go, This is what we're gonna do this year. It's gonna be great, it's gonna be amazing. It's a big raw-raw event.
People walk out, what happens? Everyone forgets. And a year after we wonder why are we still exactly where we're at? Ever seen that? Or is that just me?
So the reason for that is we're not having ongoing conversations. We just have a first convers. We just have this thing where we go, okay, I'm gonna put it out there what we wanna do, and then I'm gonna cross my fingers and I'm gonna hope it it works out.
With leaders, what I often do is I often have some sort of transformation meeting, right? And the transformation meeting is more or less a transformation meeting. It's an excuse to talk. It's an excuse to say, this is what we wanted to do, you know, in in the past month. Did we do it? No. Okay. why didn't we do it?
What needs to happen so that we can do it this month.
Those kinds of conversations are what keep change alive. The other piece, you may have seen this one too. This is another classic. The leader that wants to create change inside their team. Let's say, for example, you have a a daily meeting with your team, half an hour or 15 minutes, let's say, and your team isn't taking ownership of it. And you know, when you're not there as the boss, nothing happens. The meeting just doesn't happen, right?
Because Percy isn't there. And if Percy isn't there, you know, we're doing this for Percy. We're not doing this for us, type of thing. Right? I see a lot of leaders get frustrated because they they'd like to miss that meeting every once in a while. They have a more important meeting to attend sometimes at that specific time. And they'd like things to just keep going. So one of the conversations there is just being clear on your intention as a leader. In the next three months, what I'd like to see is I'd like you to.
learn how to take ownership of this meeting. And I'd like this meeting to be productive for everyone, not for me. I I I can be here or not. Right. But I need you all to take ownership of it. And once you start putting those things out there, people kind of know what to do. And then you know in a few weeks, look, I can see everyone's been running the meeting, which is really, really cool. But you know what parts are still broken? What parts would you like to see different?
What should we do to give more value to this meeting? The more you have those conversations, the more people are able to embrace change, and the more people are able to say, Look, this is for real. I mean, Frances wasn't kidding. She really, she really wanted this to happen. Right? So when you start being clear on your intention, instead of you know trying to use the force, that's
the the the joke I I use with my clients. It's like you expect people to mind read you and to to know what you're what you want from them. Can't expect that. Be clear on what you expect. Be clear on what you want as a leader if you actually want it to happen. And then talk about it regularly. Right? When it comes to change, the other thing that's important is to realize that sometimes some things are are just a conversation.
It's not about things being perfect. It's not about us solving a problem always the first time around. Sometimes it's just about practicing can we even have this conversation?
So sometimes, you know, let's say I want to tackle a taboo topic with a client. Well, sometimes I'll I'll tell them, look, you know, I I've been watching you for the past month. I realize every time it comes to this topic, everyone skirts around it. No one takes accountability, or you all start going around in circles. Can you all see that too? yeah, yeah, yeah. We can see it too. Okay, okay, why is that? And then we s we try to talk about that a little bit.
And sometimes we hear we hear like Trevor say, Well, you know, I I'm just uncomfortable giving this this feedback to Thea because I I I don't know how she's gonna react. Okay, well, Thea, how are you gonna react if Trevor says this? Well, it'll be fun. Okay, now you see you have permission, Trevor. Right. So we kind of engage in a way where I try to normalize things. I try to bring things that are that they know about.
But I I try to make it like safer for them to talk about these things. And sometimes we'll have a conversation and it'll fail. It'll be like an absolute mess. And what we do sometimes when we reach those is we laugh together and go, okay, so that's why we're not having this conversation. I see it now. Let's say we want it to be more successful next time. What would we do?
And we stop, we come back a week later and we agree that we're trying again. Right. And because we're trying again, there's not this frustration of, you know, this never works. Because we kind of put it out there that we're just, we're just trying right now. When it comes to conversations, too, you can always do a reset. One of the tricks I've learned, I shared this with with Bernie on on his podcast. I I've been doing this with my spouse for the past couple of years.
I've been with my spouse for 35 years. So when you have 35 years of history, there's a lot of conversational debt, right? Because we've appeased, we've put things aside, right? But what we've learned is when we're having a conversation and we're getting into a place where it's getting more heated, sometimes what I'll do is I'll say, okay, this is not a productive conversation right now. This is not going the way that we want. If we keep going.
You're gonna say this, I'm gonna say that, you're gonna say this, I'm gonna say that, back and forth. this is not gonna be productive. Do you want to try again? Let's start this whole conversation a different way. And the first times I did it, my spouse would look at me and she was like, You're crazy. But one time she said, Okay, let's try it out. And when we tried it out, we just said, Okay, so here's where we're at. I've been saying ABC, you've been saying
XYZ, are we clear on what we've said? Yeah. Okay. Now let's start from here at this point. This is where we're starting. And usually that second go is much more productive than the first one. Because it's kind of you just let go of all the stuff that's preventing you from talking in the first place. Does this all make sense or do am I talking in the clouds?
There's leaders that I work with that when we talk about the art of of having a conversation or having a difficult conversation, what people will tell me is, I can't have that. That's gonna be that that's gonna be a difficult conversation. That's gonna blow up. Let me tell you the biggest secret that you'll ever hear about difficult conversations. It will be as difficult as you choose to make it.
If you choose that it'll just be a conversation, we'll just have a talk and I will be responsible for making sure that the conversation stays in a healthy place.
You can do wonders with any conversation. Any of them. Right? And they become a lot easier. So I was telling you about conversations with the leaders around you, conversations with your leadership team. There's another set of conversations that's that's very important too. And you know, it's the conversations you have with yourself. Ever pay attention to those?
Sometimes there's conversations that we have with ourselves where we're not productive. We're not helping each other. Well, we're not helping ourselves in the conversation that we're in in the inner dialogue that we're having. And then what happens, one of the distinctions I like to teach people is this notion of powerless versus powerful. And you can tell yourself stories that are going to make you powerless, that are going to take all your personal power away.
That are give you going to give you all the reasons not to do something that you want that you're looking for. Or you can have conversations that give you power. Or you can tell yourself stories that'll give you courage. Or you can tell yourself stories that will, you know, and what if I wanted to do this? What would I do?
And that's that's a very important notion too, as as a leader, you know, as as entrepreneurs, we it this isn't an easy time, at least not not in my part. I I s business has been harder in the past in the past year, year and a half. And you know, I've I've had to notice a lot the conversations I'm having with myself. Why aren't people answering when I send an email? I I had a very good relationship with this person. Well, you know, maybe that other person, it's not that they hate you.
Maybe they're just overwhelmed. Maybe they're just stuck in their world. They have their circumstances. And maybe they didn't even see your message. Right? So, what stories do you tell yourself? What conversations do you have with you that give you power to keep going? That give you courage to keep going, that give you a reason to try something. I find that is.
is is so important that that dialogue that you can have with yourself as a leader.