Episode 312: Want Better Collaboration? Embrace Active Listening (with Stephen Shedletzky)
In this interview, host Ritika Chhikara talks with leadership expert Stephen Shedletzky about the core attributes of effective leaders, the difference between a driver and a true leader, and why the term "servant leadership" is insufficient. They explore how innate attributes such as empathy, authenticity, decisiveness, selflessness and accountability differ from teachable skills, and how these can be developed through deliberate experiences. Shedletzky introduces Robin Dunbar’s social‑relationship limit (≈150 stable connections) to illustrate why leaders must be mindful of their influence and why layered management structures are essential for scaling. The conversation then shifts to building a "speak‑up" culture: the role of fear, eustress, psychological safety, and the "speak‑up spectrum" that ranges from sycophancy to harmful authenticity. He explains the concept of "candor with care" as a learned skill that balances honesty with empathy. Organizational change is framed as three interlocking gears—mindset, actions, and systems—illustrated by the mantra “act your way to new thinking.” Practical advice includes limiting direct reports (8‑25), using open‑ended questions to foster empathy, and aligning incentives with desired behaviors. Personal influences on Shedletzky (parents, a Holocaust‑survivor grandfather, a mentor from Simon Sinek’s team) and his friendship with Mitch Freed are shared, as is a book recommendation (Good Awkward by Hannah Pryor). The interview closes with a teaser for Shedletzky’s upcoming appearance at SKEW Camp in Nashville, promising a small, intimate, and interactive experience.
Chapters
Shed, it is so good to see you.
Thank you. It's great to be here with you, Bobby, and with your listeners.
You bet. You have a connection to this industry, which we will get into toward the end of our chat. But this whole book of yours and this idea around Speak up culture is such a timely topic. In the book you cite retired Navy SEAL commander who talks about five attributes that make the best leaders. Empathy, selflessness, Authenticity, decisiveness, accountability. I was curious of these traits, which have we had this overabundance of training and insight on. And which do you think is the most overlooked?
Yeah, so this, I referenced the work from my dear friend Rich Devini, who's a retired SEAL and wrote the book the Attributes. The interesting word I'll first highlight is train, because skills. So a skill is something that we can learn or teach. An attribute is something that is far more innate, like empathy. Some of us are born with greater empathy than others. It doesn't mean though that we're doomed or have a cap on our empathy. Empathy isn't something we can train or teach though. Empathy is something that we can develop. And in order to develop, we need to have awareness that we might be lower on these attributes so that it's worthwhile to develop them. Um, and then go on a deliberate path to actually go do it through our experiences.
I see.
So go out and volunteer. Go do something that will increase any of these attributes. Um, so that's one distinction. I mean, my, my short answer is yes, all of them. I, I think we have a leadership deficit and I think we have a leadership deficit because we haven't adequately defined what we mean by leader. Leader doesn't mean that you're the one in charge. Leader means that you're the one who takes care of those in your charge, takes care of those in your span of care. And I, I think that we select leaders, but we don't necessarily do it based on identifying if folks are high on these attributes. So it's a bit of a cop out answer. But I, I think all of them. No, it's actually we underdevelop.
Yeah, it's actually not because I think we end up taking on a leadership role sometimes just as a result of success that we've had in whatever we're endeavoring to do. And therefore we kind of assume that leadership is a trait that are something that's going to come somewhat naturally, even though we know in our guts that it's not very natural to do so.
I mean, it's very hard. I mean, you, you Perfectly pointed out that oftentimes this is the way how promotions work. Who's the best at the job? Who's most driven? Oftentimes, who's the most charismatic? Even if charisma isn't a requisite attribute for the leadership role, who do we like most? You know, and we just promote that person. Who's the most responsible, who's the best at the job. But performance in the job doesn't necessarily indicate what will they be a great leader. It's a different set of skills and attributes to be a leader than it is to perform in the job. So I think we need to define what we mean by leadership and our attributes and behaviors, select leaders against those criteria, and then help leaders lead. The best time to learn leadership is on the job. So how do we actually support those in those roles? Even before they're in those roles, should they have some of those attributes?
Oh, that's a great point. Most leaders I know really struggle with the role. I mean, when we read a book like yours or we listen to a podcast like we're doing today, we sort of begin to tweak the dials and levers. We hear one thing and we sort of adjust and to what we've learned. And if you had to sum up your book or help a busy leader focus on like one sole attribute or skill, would you encourage them to zero? I know you just mentioned all of these were really important, but is this just a personal assessment that each leader has to do themselves?
I mean, the, the work of being a better leader and dare I say human being is, is never ending. I mean, that's, I think it's one of the most daunting yet inspiring ideas there is. I mean, we can learn, evolve, and grow in our deathbed. That's what it means to be human. When I think about, you know, what's the one thing that I would want to impart to a leader of, hey, if you're stepping into this role, this is one thing I would say look out for and listen. And it's kind of a two pronged and one theme. So the subtitle for the book is When Leaders Truly Listen. People step up. And when I put that forth to my, to my editor Kendra, she said, you don't need that word from a grammatical point of view. Truly, it's a superfluous word. Like, it doesn't add anything. And I'm like, no, it does, because listening is a skill. You can be an exceptional listener, but then take the data that you get and use it to Manipulate. You use it to make others right or wrong. You can actually weaponize listening if it isn't combined with compassion, empathy, and so that word truly listen. And then I think another thing within that that leaders really need to try on, and I think we need a lot more of this in society, not just business, is it's not that the goal is night is not to be right. The goal is to be better. And as a leader, the opportunity is to listen and to show up with a posture of progress and better, not right or wrong. I think we need a lot more spectrum and less binary in the way that we operate as human beings and as leaders politically as well as in business and in all of our relationships.
Such a great thought. Such a great thought just all around, especially heading into election season here in the US that's such a really good thought.
I'm very comfortable up here north of the border for the time being. Bobby.
So, yeah, for those that aren't sure, Shed is in Canada. So, you know, so he's. He's a little bit of safe zone. As I touched on that topic just gently and then got off it real quick.
Yeah.
Back to leadership. Some terms to sort of demystify Shed.
Yeah.
Like what's the main difference between a driver and a leader? And I think we get the negative inference of a driver. And then I have a sub question. Why don't you like the term servant leadership?
Yeah. So this distinction, driver and leader, also comes from my dear friend Rich Devini, the retired CEO who wrote the book the Attributes. And I love how he outlines this. So a driver views people on a team or an organization as cogs in a wheel to push, to drive, to manipulate that. That people are an expendable resource. And I think we get so many of the issues that we get at work today when. When those who are in positions of leadership show up with a driver mentality.
Like people are buttons and levers.
Exactly. And it's essentially like putting a snowmobile in sand. It'll work, but you have to replace the parts. Right. And those parts, those, those parts happen to be human beings with heart, heartbeats and emotions who are complex and who are wonderful and who are capable of doing wonky math. Like 1 plus 1 equals 17. When you get the conditions right, when a team can synergize. This is the value of leadership. Because what a leader does, it doesn't team or organization as a machine to operate levers to push or pull. It views an organization or team as what it is, a living and breathing organism that should be fed and maintained and given rest and given attention. And so I, you know, so much of why I do this work is in 10, 15, 20 years when my kids go and get their first job. Sheesh. My daughter's turning 8 now. So in 15 years when my daughter go gets her her first job. Actually far less. Sheesh. I'm aging my here. Whenever she goes and gets her first job, I want her to work with a leader, not for a driver. And just. Your second question, the reason I don't love the term servant leadership. I'm a fan of the concept, Robert Greenleaf's concept of servant leadership. I just think that if you have to put the word servant in front of leader, it means that, that we've inadequately defined what it means to be a leader. Because leaders serve. That's the skin in the game. That's the bare minimum.
Yeah. It's harder for leaders today, isn't it, than any time before. Would you say that?
I mean, maybe. I think one of the challenges is there's so much information and so much distraction and pressure. You know, like one of the challenges I have as a human today is, is the world in a worse or better off place than it was X number of years ago? And I don't know the answer, but I do know that we know more because of media. We. We can learn and see so much suffering, whether it's climate, whether it's war, whether it's famine, whether it's in just like. It's just. It's front page everywhere all the time. I don't know if. I don't know ostensibly Bobby, if the world is worse off or better off. But the challenges of so much information, so much negative information coming our way, just makes it hard.
Yeah. We have a lot of salespeople who become CEOs in our industry. And maybe this is indifferent with a lot of organizations that you train and teach and those personality traits in that sales role. Even when you worked with high touch clients on a very sophisticated team, they worked very well in sales. But the shift to become a leader requires such a different skill set. We even see a lot of companies, as they grow, evolve to something like eos or some systemized way to help them learn how to lead. Because. Because they don't have the tool set for that. They've got a tool set for sales, and that's completely different. Do dynamic personalities sort of influence a false image of what we think of as a leader?
Yeah. And. And it can get us into trouble when we promote charisma. Because there's, because often this isn't, this isn't a blanket statement. But oftentimes those who are more charismatic can also have more narcissism. And I mean narcissism is important. When narcissism derails, it becomes a narcissistic personality disorder, which is destructive. Narcissism, which is a healthy view of oneself, can be an important leadership attribute. I don't think charisma is a leadership attribute though. You know, if, if you're in a sales role, charisma can be not always, but can be valuable and it can help woo and build relationship very quickly. But when you step into a leadership role, I mean, charisma and warmth aren't requisites of leadership. Especially if you're authentically not that way. If you know, one of my best leaders, people leaders ever, Bobby was consistently cold and grumpy. But I never had a doubt that she had my back. She cared about me so much. It was an intense care. But she wasn't a warmer, charismatic human being. It didn't make her a worse leader. She was consistent. So I think, yeah, we need to look at what role are you stepping into and what are the requisite attributes and skills needed to thrive in that role. If you're naturally charismatic, great. But know that there might be other attributes that you need to develop and work on to thrive in that new role.
I think it's so crucial because I think we end up, we'll really frustrate ourselves if we think we have to become an entirely different personality or bend toward a personality traitor type. There's a quote in your book, the best leaders develop leaders. How does. I was intrigued by this. How does Dunbar's number help us understand how we shape others and how they shape us?
So Robin Dunbar is a social psychologist. He's theorized that we can maintain as human beings about 150 stable social relationships. And what this means. When you get your email in the morning from Facebook saying it's so and so's birthday and you're like who? And you click on the profile and you're like, who the heck is that? That's the definition of a. A relationship that is not a stable social, social relationship. Even if Facebook tells you that you're friends. Because we're not biologically wired to have 5784 friends. We are a community based species. Our origins is that we lived in groups of 100 to 150. As soon as we reach that number, if we grew more, we would typically split off into two groups or two tribes. And the value of this is, you know, we, we know the cliche, Bobby, that you are the average of the five people you spend the most time with. Well, it's actually true because you spend 60% of your time with five people. Wow. So, you know, there's only so much relationship we can develop with so many people. As a leader, you need to be mindful of your influence because people might have a relationship with you even if you don't have a relationship with them.
Yeah.
If you're the CEO of a large organization or you're a leader in an industry, people look up to you and know that as a leader, your whisper is a shout and your tiptoes are stomps. So even though you can maintain 150 or 250, which is sort of the top, if you are in a role of leadership, there's a parasocial relationship where more folks know you and you're under the microscope. So you ought to behave in a way that is worth following.
That's really relevant to this industry too, because as businesses grow and evolve, they have to end up bringing in layers of management structure. Knowing that they can only impact a certain number of people helps also add more fuel to the idea that they do need to build in leadership layers to help lead the team going forward.
Totally, totally. Because. And that's the only way to scale. Culture is one team and leader at a time. And if you're a leader, you know, you, you can't expect to be successful with 25 direct reports. Maybe, maybe eight, you know. Yeah. I don't think we should have too many more than that.
Yeah. It's funny you say that, because I think the number one mistake I made building an agency in this business was not building enough layers of management structure in the business because of that very reason, what you said, you almost just nailed the number of 20 to 30 direct reports, and it just wasn't something that you could scale at all. Speaking of culture, why don't we speak up more generally? Or rather maybe, maybe a way of asking this is why do some of us speak up frequently and others rarely?
So I think there's a couple of things happening here. So one is personality and the other is environment. More important than personality when it comes to a speak up. Culture is the environment that if the environment is one where people are not encouraged and rewarded, in fact, they're discouraged or punished, whether directly or indirectly, for speaking up. I don't care what your personality is. I equate culture to A, to a pickle jar. You put a cucumber in a pickle jar, the brine within that jar determines the pickle that you become. So you can take a wonderfully hardworking, ethical, talented, trustworthy person, put them in not a great environment where speaking up is not encouraged and rewarded. They're not going to speak up. Speaking up is always a risk. And there's more benefit sort of to the organization than to the individual to stick one's neck out and share vulnerably an idea or feedback to help a colleague grow, or a concern or disagree, especially with someone more senior than you, or admit a mistake. I mean, it isn't about fearlessness. Fear is actually vital. Fear is data. And so the goal is not to create. You know, when anyone says, here's our fearless leader, I'm like, no, no, no, that's not the goal. Because if you come across a leader who's truly fearless, they're dangerous. That's a destructive leader. Fear is biological. And so fear is data which guides us whether to fight, fighter, fighter or freeze. And so we need to, as leaders create less fear in our culture. And to make the fear worth walking into that, on the other side of that fear, it's worth it. It's, it's a reward. So the, the. Yeah, go, go, go.
Well, I was going to say on the, on that topic then can you unpack this fear a little more? Because I think businesses, by default, we create an environment unintentionally of fear as a baseline. It sometimes feels like because you, you're dealing with people's incomes and their livelihood and everything's tied to big decisions. There are no small decisions when it comes to making those big choices like that. Is, is there a way to create a hard driven culture without fear of any kind? Or are we misunderstanding fear as a positive force?
So, so there is such a thing as eustress, which is a healthy level of stress. When, when folks show up to work and they don't know if they're going to make it through the day and get a paycheck, that's not a healthy environment. Fear baseline levels of fear are normal. It's a human emotion. The goal should not be to eradicate fear. The goal should be to assess fear and then assess is it worth pursuing or is it, is it worth actually not, not pursuing? But I think one of the misnomers that we get with, with a speak up culture is I talk about a speak up culture including psychological safety and a perception of impact that my speaking up will actually lead to some sort of positive outcome, but that does not abdicate accountability. A part of a healthy culture is both psychological safety and accountability and. And boundaries and goals and realization that we're still operating a business here and need to serve our end use. So I don't think we should purposefully or even unintentionally use fear as a driver or a motivator. That isn't healthy. But I think we need to realize fear is a natural human emotion. You know, anytime I used to utter the word feedback for folks on my team, the next thought is, am I getting fired? Right. I needed to train them to go, no, no, no. This is part of our culture and how we give feedback to each other to help one another grow. Yeah. I can't say you can't feel fear. That would be gaslighting.
Yeah.
I want to create an environment where they say, wow, when we have these conversations, I need you to know my initial reaction is fear. Now I know how I need to flex as a leader to try to limit that or lower that.
Yeah. Fear is a positive attribute or a positive leverage for accountability is actually a really great way to frame fear in a new way. It's almost like with being a creative person, um, it. It took me forever to realize that anxiety was actually a healthy part of the creative process. That the right kind of anxiety was. Was the right. It was helpful in that. And it was. It was all about tension, but it was kind of the right kind of tension that leads to a more productive environment.
Sure, Totally. I mean, there's some interesting new work coming out about procrastination, that there's actually benefits for your creativity to. To procrastinate. Because oftentimes we'll say I'm procrastinating. But you're still thinking about it.
Yeah, exactly.
So that. That anxiety or that eustress, I don't know if it's fear, but that anxiety and eustress can actually be a spark and a positive tension for action and for creativity.
For those that might be wondering, obviously Shed is going to be joining us Skew camp in Nashville in the fall. We cannot wait to actually go through a whole lot more of this. So we're going to get more of Shed and his thoughts about this because we're unpacking a lot really, really quick. One of the things that I wanted to talk about was a phrase that you use called candor with care. Because speaking with candor is. Is. It's a learned skill, is it not?
Yes. I would say it's a Learned skill as well as there are some attributes around vulnerability and courage that will help with speaking with candor, with care.
Okay, can you talk a little bit about the speak up spectrum? What is that?
Yeah. And speaking to sort of our previous conversation around some folks speak up all the time and some folks don't and the environment that we're in. So I've learned a nuance, which is, you know, speak up is a culture, not an instruction. I can't just say speak up. I can't just order you to. I, as a leader in a relationship, have to create the condition that you're speaking up feel safe and worth it. Now, as it turns out, not all speaking up is created equal. I would call a speak up culture one where there is emotional intelligence and situational awareness and tact and decency and respect. Now, the spectrum is outside of that sweet spot. On one end, there's sucking up, which is, boss says it's good to speak up. I'll just do it all the time. That's not a speak up culture. That's hogging air. And you're speaking up to be seen. Right. You're the feedback and coaching there is. I'm glad you feel comfortable to speak up. The test of your leadership is how much you're helping others and elevate and being an ally to hear others voices. Because we hear from you too much. Right. Let's hear from others on the other end of the spectrum. It isn't a hall pass to be a jerk. It's one of the sort of shadows of authenticity, which is. It's not like, yes, we want to show up as our authentic selves, but if your authentic self is an a hole, you got to work on that. Right?
Right.
And so a speak up culture is not a. Is not a hall pass to be a jerk. There are some challenges sometimes with folks who lack self awareness or there might be challenges to overcome with neurodiversity as an example, where they don't know they're being a jerk. It's our opportunity to reward the intent, but provide coaching on the behavior and the. And the impact, which I think we can do with candor, with. With. With care. By the way, Bobby, that's a really
good reward the intent and then coach everything else. I think it's fantastic.
Yeah.
There's a phrase. There's a phrase you use in your book that I love, and this may get us off of our particular topic right now, but it said, act your way. Act your way to new thinking. Mm. That's a Great phrase.
Yeah, it is.
How do we, how do we, how does that look in leadership roles? Because something you said earlier in the conversation was you really can't work on leadership until you're really in, in the kind of role. It's an on the job type function.
Yeah. So there's. When it comes to organizational change or change in any behavior, I've learned there are three gears that all have to work and the three gears are mindset, actions and systems. So mindset, good old quote from Kinky Boots on Broadway is you can change your world when you change your mind. That if you have some sort of experience where your point of view shifts, that can change everything. When you view something differently, when you view your responsibility of what it means to lead.
Huh.
It like shifts everything.
Yeah.
Now if you have a shift in mindset but you successfully do squat about it, any shift in mindset isn't going to lead to anything unless you bring on new actions. And then the, the systems piece is when a good person meets a bad system, the system prevails every time. If, if you're like, hey, we're all about collaboration and all of our sales folks are compensated 100% on commission.
Right.
How's that going to work out when the, when the going gets tough. Right. You actually need to build an incentive system that matches the type of behavior you want to see. The act your way to new thinking piece is, let's say, you know, you want to create more care, more empathy. I can't say, hey, Bobby, more empathy this afternoon, please, like, okay, but I can actually have you act your way into new thinking. I can equip you in your role with a set of questions and I say you can ask these open ended questions with the people that you work with, of the clients that you serve, and then you need to zip it. And the questions are so good around like, how are you really doing today? What do you need most for this to be a success? Right. And then zip it and then listen. And then all of a sudden you're like, wow, this care, connection and empathy stuff is really powerful. Right. You can actually act your way into the mindset shift of these are worthwhile pursuits. And I now have the action that I can lean into to make it happen and do.
Thank you for clarifying that. That's fantastic. I also want to, I would be remiss if I didn't mention this because we create a system that helps companies and sales teams collaborate better together. And you are so right sense that a leader can be really banging Their head against the wall trying to create a more collaborative team. But if their system doesn't allow them to work better together, it's going to sound like a self serving statement, but it's just a light bulb went on with me. It's like you could be working on the wrong thing as a leader. You could actually be focusing on something more systematic, systemic, to use it in a positive term, systemic through your organization first and then layer these other things
on top of it and it can be a yes. And I think to, to that point of, of how can the systems work for us, not against us. How can we be salmon swimming downstream as opposed to upstream?
Right.
That we stop swimming and all of a sudden we're, we're a bunch of lengths back.
Yeah. About you, let's talk a little bit about you Shed. Who developed you as a help?
Do we have to.
I love this, I love this part. Who helped you develop as leader?
Definitely my parents. I think inadvertently, you know, my dad is not someone who likes to be in the spotlight. I'm comfortable with it. But he, he and you know, my mom as well, just instilled values of what it means to be a good, respectful human being. I think my grandfather hugely, who's a holocaust survivor and led seven people in hiding to survive that, that war, he and I were, he's, he's passed, but we're very similar. And then one of my bosses, I work for, for someone on Simon Sinek's team for gosh, close to 10 years and she was the consistently cold and grumpy leader who had my back. She was amazing. And she, she had a strength of understanding what makes people tick and having an ability to communicate in a way that they could hear around how they can grow and their opportunity to grow as well. So she really, I think if there's one person who helped me grow the most in my life, it was, it was her.
That's phenomenal. You have a great friend in this industry. Here's the little connection I promise at the beginning of our conversation. A great friend of ours, Mitch Freed, CEO at GenU. Mark, what have you learned from Mitch? What is his friendship gifted you?
Oh, I love Mitch so much. He's such a wonderful guy. And you know one of the phrases that I love and strive to live my life by, Bobby, is nice guys finish last, meaning that they have longevity or nice people finish last, meaning that they have longevity. And I think Mitch and his family are just wonderful examples of this, that you can do things the right way and be successful. I just look of their values of integrity and honesty and kindness and generosity. So yeah, both Mitch and his. His dad as well and their family. Just how you can do right and
do well, that's phenomenal. For those that maybe aren't familiar with Genu Mark, they're one of the top 20, 30 distributors in the industry and very successful. So always so great to hear that when you hear a company so successful, led by folks that are just such good people. All right, Shed, what have you read? You're processing things all the time. What have you read, watched, heard lately that's had a really profound impact on changing the way you think? Maybe it has nothing to do with leadership or maybe it does.
There's one. One of my favorite new books is Good Awkward by written by my friend Hannah Prior, and she built some research that I heard Adam Grant quote around. Authenticity and connection aren't necessarily about being perfect. It's actually about embracing who you are. And so we can actually build trust with Oz and we can build trust by just being who we are. And so, yeah, good. Awkward is a. Is a great one in terms of how just being who you are, warts and all, actually ends up building more trust as opposed to putting on some sort of filtered appearance of who you are. You know, as human beings, we are sort of authenticity sniffing machines. Like, we just know and it'll catch up to you. So yeah, I would recommend Good Awkward, written by Hannah Pryor. I love that.
I'm gonna love the title. The title. I wrote it down immediately. I was like, I have to read that. All right, Shed, so what can we expect at SKEW camp in Nashville in September?
We can expect things to be like this, I would hope. Fun, light, but with depth and engaging. I mean, when I come and do events, I'm not scripted. I want to do everything in my power to share just enough meaningful content that participants ask questions and engage in ways that are meaningful to them and engage in ways that will help them grow and be better leaders when they leave the conference and go back to their day to day.
It's such a great connection with us and you because that's a perfect format because it's a small, intimate event with some of the most progressive thinkers and leaders who really lean forward and want to change. So it's going to be a fantastic time to have you there and to know that you're already connected with this industry and already know a lot about it is. Is fun too. So, Shed, thank you so much. You and your team and Al and everyone have been wonderful to work with, so thank you for that, and we'll see you this fall in Nashville.
Can't wait for it. I'll get my cowboy boots and hat ready.
All right. See you there.
See ya.
