The Unsure Entrepreneur

Stephen Shedletzky
Episode 34

KEYWORDS
Leadership coaching, psychological safety, speak up culture, entrepreneurship, organizational culture, feedback, team dynamics, self-awareness, delegation, innovation, trust building, leadership behavior, employee engagement, business growth, leadership development.

SPEAKERS
Stephen Shedletzky, Roger Pierce

Stephen Shedletzky 00:00
We can't ask people to perform at their best, to share their best ideas, if we haven't created an environment in which they feel that it's psychologically safe to do so.

Speaker 1 00:09
You're listening to the Unsure Entrepreneur podcast with Roger Pierce, whether you're scribbling business ideas on a napkin or wrestling with the should I shouldn't I question, get ready to explore the realities, the risks and the rewards of entrepreneurship as we share the stories, scars and successes of small business owners.

Roger Pierce 00:31
Hey, aspiring entrepreneurs, welcome back to the Unsure Entrepreneur podcast. I'm your host. Roger Pierce, my guest today believes that true leaders know they're both part of the problem and part of the solution. He's passionate about helping leaders create environments where people feel safe and encouraged to speak up. Stephen Shedletzky is the author of speak up culture, a keynote speaker and a leadership coach. Early in his career, he was the fourth person to join Simon Sinek's team, a well known author, where he co hosted the Start With Why Podcast and led leadership development programs for organizations around the world today through his firm, shed inspires. I love that name. Founded shed inspires.com he helps leaders put people and purpose first, something we can all learn about. So in this episode, we're going to talk about what entrepreneurs need to know about leadership before they hire their first employee, or maybe just as they're hiring their first team members, how to build workplace culture from day one and lessons from his new book. Speak up culture. Stephen, welcome.

Stephen Shedletzky 01:39
Thank you so much, Roger. It's a joy to be with you and your listeners.

Roger Pierce 01:43
It's good to have you here, and we're going to get into all kinds of good stuff here and talk about your book. So tell me a bit of the backstory. How did you get into leadership coaching and training in the first place?

Stephen Shedletzky 01:53
So yeah, and you make me think of the the E Myth from from Gerber, right with that? You know, I haven't read the book, but I know the pyramid so often entrepreneurs are like, I like fixing cars. That's a hobby. I'll open a auto mechanic shop. But there's a difference between being good at the hobby versus operating a business, versus being a visionary for where the business ought to go. And when you're an entrepreneur, I think you need to know where you sit on that and where you have business playing in any of those respective areas, and where you need help, because none of us can do it all. My journey, I studied business at Ivy, down the road in London, Ontario, and sort of stumbled into business. I followed a great lecturer from a second year biz class, and he said, go check out Ivy. And I did and that lecture named guy by the name of Anuj chandrana, who works at Google is still a friend to this day. And I stumbled into business work. I did a short stint at Knightsbridge, which was a leadership solutions consultancy, which I loved. Started in corporate my first day on my first job ever, 1000 people were let go post merger. So I was, you know, the young kid walking in as many more were walking out.

And that was really a front row seat organizational culture and organizational behavior and leadership behavior. Not even 101, it was least a 200 or three level series. Course, it was really interesting to see. And I became fascinated with, how do leaders behave, especially when under stress, when in crisis, when it matters most, and how do the choices, the behaviors, the communications of leaders either make things better or worse for people and their results. Stumbled across Simon sineks work, which I love, and then started my company, kind of by accident. You know, I was working for Simon and his team for many years, and loved working on that team, and thought I'd be on that team forever. Was always sort of intrapreneurial, even if not outwardly an entrepreneur yet. And I was often asked because I would go and speak and give talks on Simon's work was start with why in the infinite game. And I would often be asked, Roger, you know, when are you going to write a book of your own? And my response was always well, if and when I ever come across something worth writing about, because we've all read books for the sole purpose of having something to sound the back of the room or be invited into a room, I never wanted to write one of those. And so i i came across psychological safety, and I came across this phenomenon of a speak up culture, and so devoted myself to that work, and sort of became an accidental intrapreneur turned entrepreneur.

Roger Pierce 04:31
That's quite the story. And I think if I wrote correctly, you were like the fourth hire on Simon's team, so you were there early stage.

Stephen Shedletzky 04:38
Yeah, which was great to have a front row seat to how to build and scale an organization. Yeah, I got to learn, learn from that experience for sure as well, which has helped hugely in my own and building my own company and practice.

Roger Pierce 04:53
It's on my recommended reading list for new entrepreneurs. Start With Why and now your new book Startup Culture. We'll get to that in a minute. That the reading list keeps getting longer and longer, and books are such an important part of the journey for entrepreneurs, it's a chance to really dig in and learn something new. Yeah, so you often say true leaders know they're both part of the problem and part of the solution. What does that mean for new entrepreneurs?

Stephen Shedletzky 05:18
I think it can mean anything. You know, it's a it's something that's just a human fact. And I think those among us who are effective leaders and effective entrepreneurs have the self awareness and humility. We have strengths. We have genius. There are things in our zone of control and influence that we are masters and wonderful at, and there are areas where we are limited, and there are areas where we are weaker, or we have areas that are blind spots, especially for entrepreneurs who are trying to build something, to build great awareness of what are my strengths, what am I going to be great at, and what am I going to get in my own way with? And how am I going to trip others up as well, even if it's inadvertent, and to religiously build relationship with that as you you know like there's a lifestyle business where you can be a an entrepreneur, but it's really only you and maybe a couple vendors here and there are contractors. But if you're growing something that really like its scale and its growth depends upon a a team and more people and hiring more, you really got to be clear on where are you going to create momentum, and where are you going to create dissonance, and as much as you can hire for, solve for where you're going to get in your own way, in the way of of others, of which we all have these things.

Roger Pierce 06:39
You raise a good point. You know, play to your strengths, delegate your weaknesses. Learn, learn, learn. That's a good work around too. I'm terrible at accounting and numbers. I'll hopefully admit that, so I delegate the heck out of that to the accountant. What are you good at? What are you not so good at? What do you delegate?

Stephen Shedletzky 06:56
I definitely delegate numbers. So yes, I have a great accounting for him, and I have someone on my team part time who does financial management for me as well budgets and what can we afford to do, and targets and all these fun things. I'm also not great at admin and organization. I can be detail oriented when it comes to words and design and some really nitpicky stuff, and then I can be totally not detail oriented when it comes to admin, contracts, invoices, things of that nature. So I love building relationships. I love speaking and facilitating and training and coaching. I don't love the organizational execution part behind it. So that's where I get I get help and form accountability on certain tasks that only I can do as it relates to as it relates to content.

Roger Pierce 07:47
And thank you for sharing that so openly. It's important that new entrepreneurs understand this. You don't have to be good at everything. You're not going to be good at everything. Like Michael Gerber says, figure out whether you're the entrepreneur, the manager or the technician, and partner up, hire delegate, take training. You are not going to be good everything as an entrepreneur. And people get nervous about this, they go, Oh my god, I'm gonna have to do a lot of selling. Okay, that's important for a new entrepreneur, but there are workarounds. You can partner with a person who's maybe strong in sales. You can develop marketing systems or bring in the leads. You shouldn't sweat it, right? You're not in this alone, are you Stephen?

Stephen Shedletzky 08:23
No, no. And I also think this is a huge piece of where a speak up culture comes in, which is when you are forming a team. To get really clear on, hey, team, this is what I know that I believe that I'm good at, or at least have a track record of saying I'm good at, or I've done these assessments and I'm good at these pieces, and I'm really not great at these pieces, and so because I care greatly about this business, because I'm an owner, because of all these things, I might try to spend time in areas where I have no business spending time in, and I'll slip into micromanagement, or I'll slip into over controlling. And this is where a speak up culture really plays benefit. When you design an accountability with your team. I need help, or I invite you to share with me when I'm outside of my lane. And then when people point out, hey, stop trying to do accounting. You're not, you're not an accountant, that's the time to take it, take a deep breath and say you're right and thank you. And go after what you're trying to go after. But, you know, stick in your lane, because we all wait. We all have lanes.

Roger Pierce 09:26
Well, that's a natural segue. I want you to dig a little deeper for me and explain what is speak up culture in simple terms, and why is it so important for entrepreneurs?

Stephen Shedletzky 09:37
Yeah, so a speak up culture is an environment in which it both feel psychologically safe and that it's worth it to use our voice, to use our voice to share what we see, feel know, to share our ideas, whether they're our best ideas or half baked ideas, to provide feedback to one another. Feedback is a source of growth, of improvement, to share concerns, the proverbial smoke before it becomes Fair. Prior disagreements and debates. I think the biggest myth of psychological safety in a speak up culture is that everyone gets along and agrees about all the things absolutely not. The true test of a healthy, thriving speak up culture is, do we have meaningful, productive, generative disagreements and debates where we can disagree, align and then commit. And finally, inside of a speak up culture, we can raise our hand and admit mistakes, knowing that on the other side is improvement and not punishment. So that's what a speak up culture is, safe and worth it.

Roger Pierce 10:33
What do you think of the expression ‘speak truth to power?’ Is that part of it for entrepreneurs and their teams?

Stephen Shedletzky 10:38
It certainly can be. And I think, inside of an of a team or an organization where there is psychological safety in a speak of culture, speaking truth to power doesn't need to be such a big deal if it's such a big deal, and we spend so much energy and effort and coaching and time in rehearsal, you might not have as as healthy of a speak up culture as possible, when you do have a healthy speak up culture, speaking truth to power isn't this overwhelming, huge, big idea. It's just what we do here. Of course, I'm going to challenge someone on my team, or the leader or the entrepreneur or whatever it might be. If I have a contrarian point of view, I'll still do it with respect and tact and empathy and curiosity, but why wouldn't I, if I believe it's going to make things better, and it's the responsibility of entrepreneurs, of the leaders to both encourage folks to use their voice and then reward them when they do, if you punish people or ignore them for speaking up, especially if it's the type of things that you do want to hear, good luck. And if someone speaks up with something that is inconvenient to hear, though likely true, you should pay attention.

As my friend Tim McClure says that, you know, the biggest concern for any organization is when the most passionate people become silent. And I've been there, I've been on a team where I've been the most passionate and I've become silent because I've been burned for sharing hard truths.

Roger Pierce 12:04
Burned for sharing hard truths, punished for speaking up.

Stephen Shedletzky 12:08
Yep, and then you learn very quickly it's better to just zip it, keep your head down, do your J, O, B, and probably get the heck out.

Roger Pierce 12:16
I gotta ask you what and what, what the risks are when leaders fail to create this culture. But I read something online before we talk about that, employees and speak up cultures are 92% more likely to want to stay with the company and contribute to their full potential.

Stephen Shedletzky 12:32
Yep, the correlation between a speak up culture and a culture of mattering, and my friend Zach Mercurio has some great work on mattering, that when we when we speak up, and our opinion is valued, and we're speaking up in the right lane, in the right context, absolutely, you know, we want to give of our discretionary effort. We feel as though we matter, and that our work, our words, met. That's good for business.

Roger Pierce 12:59
That is good for business. What are some other risks if an entrepreneur doesn't heed this advice?

Stephen Shedletzky 13:03
Yeah, I mean, you will get people who check out, or you will get people who will do the bare minimum. They'll do their job, B and no more. I mean, the thesis of the book, is a two by two matrix. Or you want it to be safe and you want it to be worth it, right now, there's three other quadrants where it's safe but it's not worth it. This is providing feedback to a dear friend who implements none of it repeatedly. It feels, still feels safe, but it feels not worth it. You know, apathy or futility sets in. There are circumstances where it isn't safe but it is worth it. This is whistle blowing. This is Ed Pierce and at Boeing, who was on the front line seeing that the planes being built weren't being built safely and smartly and well, let alone the the engineering. But when it's neither safe nor worth it, right? I've been in an environment where someone was telling me, speak up. Speak up. You're the Speak Up guy. And I'm like, It's not safe and it's not worth it. Like, why would I put myself in more psychological danger and expose myself to greater futility and apathy, right? It's an unhappy marriage when it's psychologically dangerous and not worth it. That's what you get when folks go, you know, they put up their hands. It's not going to make a difference. I'll just put in my work, put in my hours, and wait until something better comes along. That's the risk.

Roger Pierce 14:22
You. Reminded me of one of my favorite movies, the insider with Russell Crowe Al Pacino. Russell Crowe was blowing the whistle on the tobacco industry, and the world comes crashing down on him, but he sticks to his mission. Despite losing his job and his family and all these pressures, it's quite the drama. I think it was back in the 90s. Yeah, rings, rings a bell. And this is a good segue. You touched a little bit about what the book has got to offer. Can you give us a bit of a preview about what's inside the book and how it will help entrepreneurs?

Stephen Shedletzky 14:51
This is a book all about culture and psychological safety. It's also a book about leadership. What does it mean to be a leader and behave as a leader? And leadership is not about title. Leadership is about behavior. In the book, I define what a speak up culture is and share some interesting case studies and stories. I talk about how it needs to be safe and worth it. Talk about the encourage and reward cycle. But I also set a vision for how we ought to identify, select, hire and promote leaders based on their behavior, and not anything else. I talk about feedback. What good feedback looks like. I make a great comparison to culture as a pickle jar, that you can put a perfectly good cucumber in some bad brine, you get a bad a bad pickle, but you can't blame the cucumber. You have to examine the brine that it's in. I also spent some time working with Navy SEALs, and in particular one former seal, a retired commander, rich Divini, and he's actually shown me that there's a great correlation between entrepreneurship and becoming a Navy SEAL. And there's one attribute that all Navy Seals and all entrepreneurs have, and it's this word called cunning. Cunning is the ability to look at a scenario, look at a situation, a context, and go, all right, what are the rules? Are they real, or are they perceived? And what's the cost of breaking that rule, and am I willing to suffer that potential consequence?

And I think all entrepreneurs and seals work that way, because I often think, especially when you're an innovative entrepreneur and you're trying to chart into new territory, you have to look at all right, what are the preconceived notions and are they actually true? Or can I challenge it? Look at Uber that defines itself as a communications and technology company, not a transportation or delivery company, but it's undoubtedly disrupted that industry. Again, I think there's a difference between I just want to run my coaching practice business. That's a form of entrepreneurship, but you're not creating a startup. Scale up, scale, you know. So there's different contexts. I think we use the word entrepreneurship, but what does it mean? You know, is it just working for yourself, or is it building a company that can scale?

Roger Pierce 17:09
You raise a very good distinction. Very good distinction, one I am writing about and a book I'm plugging away at. There is a difference between, you know, a tech startup that someone wants to scale, build the big company, lots of rounds of investment, and a small business owner who just wants to maybe start a local carpet cleaning business or a plumber, they're not looking to scale. They just want to make a decent living. Have freedom, make some profit, have a good life, right?

Stephen Shedletzky 17:37
Yeah, there's a very good friend of mine who just went through an exit. And he prompted me with a question that I think is brilliant for listeners out there who are grappling with what's this definition of entrepreneurship and which version of it do I wish to practice? So he said to me, tomorrow, there could be a 100% chance that there will be a million dollars in your bank account. That's option a scenario A. Scenario B is there's a 10% chance you'll have $10 million in some time. And option C is there's a 1% chance you'll have 100 million. What do you take? And I went, I go with a and he goes, perfect. You're running the type of business that you should be running. I'm running a lifestyle business. Sure, I'm looking to scale a little bit with an online course here and a partnership here, but like I'm looking to do the work of speaking, facilitating, training, coaching, like I'm not looking to retire at 45 I intend to keep doing this work for as long as I'm physically and mentally able to do so, and I'm very happy to have some passive income, but that's my approach, and that's what I'm comfortable with. So I think it's a good sort of risk appetite question, because if you choose anything other than C, you're probably not cut out to enter into the sort of tech startup. Let's gamble and win big because, like, the odds aren't in your favor. So I think it's a good exercise, mental exercise, to go through those sets of questions.

Roger Pierce 19:07
It's so true, self assessment is key, and there are lots of ways to do that online. There's some quizzes and things. I've got some on Unsure Entrepreneur.com but it's also asking other people, what do you think I'm good at helping to define those strengths and weaknesses you touched upon earlier. But entrepreneurship doesn't have to be like you said, this big. You don't have to be Bill Gates or Zuckerberg. You can also just be quite happy with a small, small business. I remember my father in law, he had a nice little, nice little business, nice little graphic design agency up in Peterborough, my hometown, showed out to Larry chestnut, and he loved it. He worked hard. He had a small team, nice little building, and he went golfing every afternoon with his buddies, right? That was his reason for being, was to get out there and play some golf in the afternoons. That was designed as a lifestyle business. Yeah, it's a chance. Design the business the way you want it. And I'm a firm believer that your business should serve you and not the other way around.

Stephen Shedletzky 20:05
Yep, Absolutely.

Roger Pierce 20:07
I want to just touch upon a little bit about psychological safety and performance, because that's a very nuanced topic. I mean, what do you mean by that? How do I how do I make that happen for my small team?

Stephen Shedletzky 20:19
Yes, so psychological safety, a big body of work, and Amy Edmondson has done some brilliant work in that area the way she defines team psychological safety. It's an environment in which it feels safe to take interpersonal risk. This could be trying a new thing. This could be taking a risk. This could be innovating. This could be taking a different approach. This could be sharing feedback. This could be going to your boss and saying, I think the way that we're doing things isn't as smart as if we did it this way, right? And so psychological safety is a key, one of the key pieces of a speak up culture. I highlight that, yes, it's psychological safety as well as a perception of impact, that the choice to speak up, to share my opinion and to take this risk is worth it, that I make up a story, that there will be a positive outcome, a positive change, or that I'll feel as though I matter, not diminished, right? So it's those two pieces that I think when it's psychologically safe and when we feel that the risk to speak up and use our voice to our opinion be vulnerable, that it will lead to a positive outcome, then we're more likely to have better results as well. We can't ask people to perform at their best, to share their best ideas, if we haven't created an environment in which they feel that it's psychologically safe to do so.

Roger Pierce 21:38
I get it. I get it. So can you give me an example of how I can do that on a tactical level, like, do I give them a reward? Do I have a round table? Do I follow up?

Stephen Shedletzky 21:48
It's all of those things and more. So I think it is asking open ended questions and remaining silent. It's Hey team, this is the opportunity, or this is the issue. I need everyone's ideas. I have some preconceived notions, but I'm going to suspend sharing my ideas, because as soon as the leader shares their ideas, guess what happens? Sounds good, boss. Let's do that, right, but you miss out on everyone's ideas. So you say this is the issue as I see it. Does anyone see the issue differently than me? Zip it right, build some relationship to the issue. Okay, cool. You know, what is it? Einstein who said, If I have 60 minutes to solve a problem, I spend the first 55 on identifying the problem right. Like, let's get on the same page of what's the issue, what are we going after here? Or what's the opportunity, and then zip it. The number of times I've heard very senior leaders go, I need everyone's best ideas. Here's what I think we should do. No no, no, no, no. Like, I need everyone's best ideas. Zip it and allow yourself to be surprised. And as you do that, people will feel encouraged and rewarded more on the intrinsic side, thank you. That must have taken courage. We didn't implement your idea. But here's why I'm not yet seeing what you're sharing. Can you share more? Where did you come to that conclusion? These are all forms of intrinsic rewards that makes it safe and worth it to keep speaking up.

Roger Pierce 23:10
Over time, if I'm raising my hand and offering all these great ideas and speaking up, what if none of them gel? What if none of them are action, do I start to get resentful?

Stephen Shedletzky 23:19
I mean, potentially. But here's the thing, if you're speaking up, it's not about you speak up and everything you say is implemented, or everything that you put forth is right. I mean, listen, if someone's speaking up and it continues to be like, what like, are we working for the same cut like, what like? Where are you getting that from? And if it's just whacking out of left field and doesn't gel with the reality that everyone else is seeing, I think that's a different conversation. But there's definitely a scenario where you speak up and it doesn't go exactly your way, but you can still feel at the end of it that it was worth it to raise your your opinion, and maybe because something else is going on that you didn't know, or maybe there are constraints, or whatever it might be, yeah. I mean, I don't think a speak up culture is about, oh, let's just implement what everyone says. Now, that's chaos. If someone's repeatedly speaking up and nothing's happening, you know, it may not be the right fit for them, but it's not about everything being implemented all the time. It's about making people feel that they matter,

Roger Pierce 24:25
Good to know. And these are some of the nuances and things you're going to help your clients with in your workshops and your training. Before we get to my final question, can you tell us what that looks like, what your services, how your service is offered and packaged up, Stephen?

Stephen Shedletzky 24:39
So my practice is based upon answering the questions, what does it mean to be a leader? How do we build trust? And what is trust, and where does it come from? We know culture matters, but what is it? What are its building blocks? And how do we build thriving and healthy cultures? So that's what I really focus on in my work, and it's keen. Out speaking, fireside chats, workshops, team coaching and some one on one coaching, and always working to build some tools as it relates to online courses and partnerships in that area, as well as working on a podcast right now called shed some light to help folks build upon their leadership development practice at their pace and in their way.

Roger Pierce 25:20
We talked about that briefly. You are working on your own podcast. You've been on tons of podcasts, but you're, you've got your own coming out. Is there a timeline for that, or is it a big secret?

Stephen Shedletzky 25:28
The goal is to launch Q1, of 2026 so hopefully not too long after this, this airs, that's, that's what we're working toward.

Roger Pierce 25:36
Start off the new year. On the positive note,

Stephen Shedletzky 25:39
Yes, New Year, same you, lead better.

Roger Pierce 25:43
I love it. Okay, well, we're getting close to the wrap here, but I do want to ask, you know, what advice do you give entrepreneurs stepping into leadership for the first time?

Stephen Shedletzky 25:54
You know, Leadership isn't easy. It's not about perfection. It's about progress and that we never arrive. We're always arriving. I have a definition of leadership, and I think if you take this definition to heart and strive to practice it, I think you'll do more good than harm. And to me, the definition of leadership is the attempt to leave the people and world around you better than when you found them. And that doesn't mean that you have to have lifetime employment. You know, sometimes people grow apart, that's okay, but can you leave people better than when you found them? And I think that's with every micro interaction as well as a macro interaction.
So it's the attempt, because you never get it perfect all the time. And do you leave people in the world around you better because they knew you or you led them.

Roger Pierce 26:40
And by maybe signing up for one of your workshops or reading your book, we can do that and leave people a little bit better. Stephen Shedletzky, thank you so much. You've shown us that Leadership isn't about having all the answers. It's about creating an environment where people feel safe to speak and contribute for entrepreneurs that starts on day one, as we talked about, and when you make your first hire and begin to set the tone for how your business will run. So Stephen, thank you so much for joining us.

Stephen Shedletzky 27:09
My pleasure. Thank you, Roger for having me, and thanks for tuning in.

Roger Pierce 27:13
If listeners want to connect, where can they do that and what is the best way to get a copy of your book? Speak Up Culture.

Stephen Shedletzky 27:21
Yes, I believe, for the time being, I'm the only stevensky in the entire human race. So all you handfuls of should, let's use there. Please name your children wisely. But if you Google me, you will find me. I'm most active on LinkedIn for the time being, and you can find my book speak up culture at some very fine and not so fine book retailers, Amazon is is an easy one to find it, but you can also go to my website: Shedinspires.com/book.

Roger Pierce 27:48
Perfect. Shedinspires.com. Fantastic. Okay, and to our listeners, thanks for spending time with me here on the Unsure Entrepreneur podcast. If you enjoyed the episode, leave us a review, share it with someone who's building a business. And remember, you don't have to leap, but you can lean bye for now.

Speaker 1 28:05
That's it for this episode of The Unsure Entrepreneur podcast. Thanks for listening. Be sure to subscribe so you don't miss other candid conversations with small business owners, and be sure to check us out at Unsure Entrepreneur.com.