Unlock Higher Performance With This Leadership Shift
16 Jun 2025 · 32 min
Podcast episode of The Enlightened Executive (host Susan Drumm) featuring Sherry Jacobs discussing how clearly defined boundaries combined with psychological safety enable innovation. Jacobs cites ~16 years of research across 300+ organizations (~½ million people, ~1M data points) and offers practical tools: define the 'what' and fences, give everyone a voice, and run many small experiments ('take more shots').
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Hi, I'm Susan Drum and welcome to the Enlightened Executive where your personal evolution sparks your leadership evolution. Each episode we feature groundbreaking techniques and strategies to help you get the edge in personal and leadership effectiveness. Are you curious about your own development path to enlightened leadership? Take our free 5 minute quiz@susandrum.com to discover your superpower and the roadblocks that could get in the way of effective leadership. Today I'm excited because we are focusing on the unexpected power of boundaries. And I would love to introduce my guest, Sherry Jacobs. Sheri is the founder of the consulting and research firm Avenue M Group. She's also a seasoned keynote speaker with over 300 speeches and workshops to date, a highly sought after leader and a three time best selling author and award winning wildlife photographer. By blending her business acumen with the keen eye of her photographer, she offers a fresh perspective on problem solving and innovation. And her work challenges people to see possibilities where others see obstacles. So welcome, Sheri.
Thanks, Susan. It's such a pleasure to be here.
So you have a fascinating background as a wildlife photographer. How does that play into what you do?
Such a great question. And it's funny because it's something that was naturally that fit in naturally. But only recently did I start thinking about the strengths that it brought. As a photographer, especially as a wildlife photographer, you need to be very observant and you need to know as much as you can about what you're photographing so that you're prepared when the moment happens. Because everything in photography is about the moment. Anybody could take a camera or their phone and snap a photo and we call that a record shot. But to get something that's different, that moves people, that show something that they would never see, you have to be very observant. And that means being a little bit quieter and looking at the environment around you. And those skills that I have honed out in the field in Africa and Antarctica and the Arctic and everywhere I've been, I think are important skills to bring back to organizations as they try to think about how they can innovate, how they could create something that is meaningful and relevant to whomever they're serving.
Yeah. So let's make that link more distinct between how does this type of skill set help someone needing to innovate?
So when somebody wants to innovate, it's rarely done on their own. Right. It usually happens within a team, within a culture, within an organization. And you have different people who are different roles. So you have individuals who are early in their career, you have people who may be more highly experienced, but they're frontline staff. You might have middle managers, you may have the CEO, and so you all are filling in different roles that are there. What I truly believe is that in order to innovate, in order to have a team that's innovative, you need to have two things in place first. And people talk about this all the time. You need to feel safe in order to experiment. They talk about that as psychological safety so that you can experiment and know that if you fail, that's okay, because as long as you learn from it, you could take those kinds of calculated risks. But that alone is not going to get your team to innovate. I call that the wandering zone. That's where people kind of wander around. They may look at a couple experiments and ideas and then go back to revert back to what they know. Where I think that there's true power is when you combine that with high clarity around boundaries, around what boundaries are there. When you have very clearly defined boundaries and high psychological safety, that gives people the freedom to innovate, to explore, to observe what's going on around them, to look where there might be problems that could actually simply be solved. And that kind of innovation happens at every level.
So you have a fascinating research study behind this that we talked about that was the basis of some of this work. Can you share what that is?
Sure. It's actually about 16 years of research that I've conducted with more than 300 organizations collectively. That makes up more than half a million people and about a million data points. All that research over the years was with organizations around their workforce, around their members, around individuals, across a whole bunch of different professions from the American Institute of Architects, American Academy of Pediatrics, and many other industries in between. What my company did, Avenue M, is we would conduct these membership workforce studies, and we would ask people what are the challenges that they face, what are the ways that they overcome the challenges? What is it that they need? What are the workforce things that they're seeing that's changing the work that they need to do, and what do they need to solve those problems? And. And over the years, I have analyzed that data along with my team, and from that, I've pulled out three key things that I think that if most individuals or organizations looked at, regardless of your industry, regardless of the size of your company, that these are the three things that are going to help you navigate the future of work and really innovate in the future. The first thing is to really to know where the fences Are to define the fences, to know where the boundaries, the constraints are, because otherwise people are going to wander. The second is to give everyone a voice, and I can share a quick story with that in a moment. The third is to take more shots. Once you know where the boundaries are, and once you are giving everyone a voice, then you can experiment. Then you could take more shots, and that's where you'll see innovation happen.
Interesting. Okay, so the first thing around boundaries, there was. There was also some study, like, related to a playground, right? Yeah, absolutely.
Yeah. So there was a landscape architect named Tatiana, and she was curious about the physical impact that boundaries have on how kids play. So she asked a group of preschool teachers to take their kids to a playground in her. A park in her neighborhood. And the park had the typical swings and slides and playground equipment. Big grassy area, but no fence around it. When they got to the park, the teacher said just one thing to the kids. Listen for the bell, and that's when it's time to go. No other rules. You know what happened? The kids stayed on the playground. Not one kid moved into the park and played, and they all stayed close. Well, the following week, Tatiana had the same group of teachers. Same group of kids go to a different park in town. And this park had the playground, the play equipment, and a big grassy area, but it was enclosed with the fence. And you know what happened this time? The kids ran. They ran all the way to the fences. They were so much more creative in their play. They were more innovative in the things that they did just by knowing where the boundaries are. And most of us are the same, so when we know how far we can go, we'll reach out to those fences. When we don't, we play it safe. We stay in our playground. And that's why I call it like the. The idea is, how big is your playground? Because we may be having. Defining our playground so much smaller than they need to be, because nobody's defined how far we can go, Whether that's individually in our personal lives, or even on our teams. And we all have stories where we put things off because we think we have unlimited time or we don't push it as far at work because we don't know if we fail, what could happen? How can we come back? And so we just. We don't do the things that are on our list.
Yeah, because at some point, you know, it's.
It's.
We don't know how far we can go, so we don't necessarily take the risk. Right. We're not Going to overextend ourselves and leave ourselves exposed. We're hardwired to create safety in our lives. So what you're saying makes so much sense in knowing how far people can take things. Now, I imagine for many leaders, that's pretty hard to define. Can you give some good examples where a leader defined the edges of the playground?
Absolutely. One of my favorite stories is actually about bank of America. Now, bank of America wanted to come up with a new way to, to help people save money. They didn't come up with. They didn't say a new app or a new program or a new program that they would offer. They just wanted to help people save money. So they defined the what. The what is how can we help people save money? Then they built in fences around that. So they worked with a consulting firm, and they said to them, here are three things that you have three fences, three constraints that you have to work within. The first is you have to use our existing debit card and technology. No new technology. Now, Susan, I love that because most companies, most organizations, they can't invest in a whole new technology or new infrastructure. The infrastructure had to stay the same. The second thing that they said, and again, I love this so much, is we're not going to change people's behavior in this new savings idea. We're not going to expect people to change their spending habits, which is huge because so many companies and organizations come up with something, but they're expecting somebody to change for them. And then the third thing they said was it has to be automatic and invisible. Now, the idea that they came up with never would have happened had they not had those constraints, but using those constraints and making sure every voice was heard. So they talked to people that were the potential customers for this. They found out something interesting, that when people made a purchase on their debit card, they naturally rounded up in their mind to the nearest dollar. So what they came up with was the Keep the Change program. And if you enroll in it every time you make a purchase on your debit card, bank of America will transfer, will round up and transfer it from your checking to your savings. No new technology, no change in the spending habits. Automatic, seamless. My colleague Nick is actually in this program, and when I told him this story, he's like, I, I have saved over $5,000 from pennies because of that program. So it's a really simple framework which is define the what, what you want to have done, but don't define the how. Leave that play unscripted, just like the what in the playground with the kids, they have it very defined. The slides, the swings, this is how you play. But when they opened up the boundaries and said, this is where the fence is, do whatever you want, the kids are more imaginative. So you define the what, not the how. You leave the how unscripted.
Yeah, yeah. That is a fascinating story. And so that second piece then, defining the boundaries, do you have suggestions for how people need to figure that out? Like what those. Because I can imagine a leader would be sitting there saying, okay, I think I know some of the boundaries, but other ones I'm not so sure myself, like what I can push. And I'm afraid to put this boundary out there because I'm afraid it will stifle innovation. What if my boundaries are too rigid and they're too small and I'm making the playground really small? What do you suggest there?
Yes, such a great question. And that's going to be on the minds of most people. Absolutely. So what I've developed is something called a risk capacity assessment. Most people talk about risk tolerance, right? That's the psychological how hungry you feel about taking a risk, but that doesn't take into account your capacity to fail, your capacity to take a risk. So I developed this questionnaire, really simple 10 questions, where it asks questions such as it could be financial questions. So if you were to do something and it didn't succeed, how would that impact you financially? It asks questions about your brand, your reputation, the quality of what you offer. You know, it has a whole variety of different questions in there. And so the first step that I recommend is to, rather than think about what you think are one way doors or two way doors, can we do this? Can we not do this? But instead is to evaluate your capacity for risk. You may have low, medium or high capacity for risk. Obviously the Amazons out there have very high capacity for risk, right? They, they can Sink, you know, $120 million into something and then not succeed. But that's not the same as most people who are running a business. So that you have to assess where's our capacity for risk. And then once you've defined it, you say, okay, we actually have a lot of money in reserves. We could actually experiment in these new ways. Then you can invest and define the fences as what are the two way doors where people can experiment to try things and if it doesn't work, will you be fine? That's the answer to it. Now, every company, every organization, including the very small coffee shop that's around the corner from my house, can innovate and one of the best ways that I think that you can innovate as a leader is to empower your entire team, including your frontline staff. So a couple weeks ago, I was looking for a new coffee shop in my town, and I went to both of them. There's two in my area. And one of them, when I went in there, I asked for what I always asked for, which is Americana with room for cream, medium temperature, not too hot. And when she gave me, when I got the cup of coffee, it was scalding hot. And the barista could tell when I took the sip how hot it was. And she was so apologetic, and she said, this happens all the time. I have this idea. She goes, I'm going to write as soon as you give the order what temp you want on it. I'm going to put it just an M or an H onto it. And so I thought that was a great idea. Well, a week later, I go back into the coffee shop. She's not there, but there's this little sign by the cash register, and it says, tell us the temp that you want for the coffee so that we can make the perfect cup for you right when you give the order. And a different barista wrote on the cup. It was actually a W that she wrote on there. And I got the perfect cup of coffee. And I thought about, like, she didn't have to go through a bureaucracy. She didn't have to, like, submit this idea. She's a frontline staff person that saw a problem and immediately thought of a solution and then told her team and just made the sign. And I think you could scale that at any type of organization. She knew was the boundaries were fine for what she could do. She cannot give something free. You know, there was. There are different ways that you can set boundaries, but this was an easy one. Now, I've worked at an organization where I set a boundary of a dollar amount to my frontline staff when I managed a team and I said, you could do anything to make the customer happy within this dollar amount. That was what was acceptable within our frame to keep this.
Yeah.
But I think that there are ways that leaders can empower the team to make change happen and then report back and if it works, then think about expanding it.
This is so important as you scale an organization, because what I've seen. So as you scale, of course, you have to create more systems and processes and. And have one division doing something entirely different. There needs to be some centralization. Right. But what happens, and I've seen it so many times in organizations that start growing is that they lose their innovative, entrepreneurial feel of when they were small. And what happens is these systems and processes become rigid without the flexibility to allow some decision making to still happen. I just saw this with an organization where they had an issue with IT and IT spend and people just going off and getting their own software and then having all this, like, software that they're paying for that they don't need. There needs, of course, to be some standardization like, and balances and checks, like, is this something we're going to use? What's the need for it? And yet when they did that across the board, that stifled everything. People were frustrated. They couldn't, you know, they're like, this is, you know, this is under $5,000 and I'm having to fill out this long form. You know, and so that's. And that got people really frustrated. So what was missing there was just like, hey, just as simple, like, what's the dollar amount I can play with without having to go through this bureaucracy? Like, it makes sense for $100,000 spends. It doesn't make sense for $5,000 spends. So why would you layer that on everything? And so just something that simple, I think, allows people to still feel innovative while you're scaling.
Absolutely. You know, one of my favorite stories is actually a company I helped start 25 years ago. And I interviewed the CEO of it for the book I'm writing, which is called How Big Is yous Playground. And so I interviewed Troy Henikoff, and he reminded me of something that happened way back when we were starting the company, and the company made it became the largest in its vertical before it got acquired. So we had started, 25 years ago an online payroll company. Now, and anybody who remembers 25 years ago on the Internet, there was no banking. That wasn't a thing. There was a little bit of shopping. It was mostly used for email and checking your sports scores. And so we launched this online payroll company, and we had an idea about how we could sell payroll. So we tested it. We had the perfect test. We tested it with Citibank within these things called buckslifts, where we put in our logo and their logo. We made an offer. And because it went in bank statements, we knew every single person at the time. Because they didn't get the email bank statements, every person would open it. It was the perfect test. We thought it went to 300,000 people. And we had all these people, the Amanda phones and get ready for the calls, and we got Three calls, and we turned one into a customer. And so it was so clear that direct mail was not going to be the way that we were going to sell the payroll. So immediately shut it down. And Troy shifted everything to sales, and he brought in a sales team. What he knew about, though, from experimenting with different companies, he set very clear boundaries. It wasn't dollar amount. What Troy did was he said, we are best for 10 or fewer employees. We are best for companies that don't have, like, restaurants with tips or other types of complicated tax structures. And for companies are businesses that have been around for a long time. And so what he knew as he looked around his neighborhood, what had been around the longest in the neighborhood were the insurance, the state farms, the Allstate. Right. You always see it at the corner. It's never changed. It's never moved. So he brings in a sales staff, and he says, has to be 10 or fewer employees. It has to have this kind of tax structure with tips or whatever it might be. Can't have that. And here are the audiences where, you know, yes, there are millions and millions of small businesses, but we're not going to. We're going to sharpen our pencil to break through into the small business market. By going after this one little vertical, he created very, very strong fences. The sales team was so successful in selling because they had these very clear boundaries. Now the sales team could sell any way they wanted. They had. Did not have scripts. They could sell any way they wanted. They could just to close the sale. So that was where the freedom was to explore and to test different things that worked for them. But they also had very clear boundaries. Ultimately, the company we started with, sure, payroll, and it got acquired by Paychex, and it became the. The largest online payroll company in the world. It is all attributed to Troy's and Michael Alter, the two founders, their philosophy around having a sharp pencil to break into the market rather than to go wide there.
Yeah, yeah. There's a phrase I love that I heard is like, insert like a needle, expand like a sale.
Yeah.
So when you're inserting like it like that is the power of, you know, going after a particular market and really owning that market, because you also get that ability to understand that market in so much more depth and have the expertise in doing that. But, yes, it's all about what is. What are the boundaries by which we're going to go forward. And that's why I often see leaders overwhelm people with priorities. I mean, I ask people, when I'm speaking, like, does it feel like you have so many priorities that you can't even prioritize? Like you are doing yourself such a disservice when that occurs because you can't. Again, it's about that. Those boundaries, what are you not going to do so that you can do the other things? And you don't get to, like, choose. Like, time is our finite resource. So what is that priority? And how are you going to set boundaries to maintain that priority for people? But then what I also love what you're saying is then where can you highlight where they have freedom? And I think that's a step that a lot of times leaders don't give. So maybe they're going to now set the boundaries, but now, like, really emphasize. And here's where I want to see creativity. Here's what I want to see, freedom. Here's how you can do it any way you want. I think you have to have, like, both in that. In that conversation.
Yeah, absolutely. You know, a lot of new CEOs, whether they're at a nonprofit, an association they're starting, they're at a startup, or they're a Fortune 500 company, they go on their listening tour. But when they go on their listening tour, they don't set the priorities. Just like you said, Susan. Right. So they'll say, I'm listening, but what if instead they said, these are the three things that I'm going to focus on in this year within those three things, Now I'm listening. What works, what doesn't work, what do we need to start paying attention to within it? I don't actually believe that there is survey fatigue, whether it is of your employees or getting that feedback, I really believe that there's inaction fatigue. So if you have a huge number of priorities and you ask for or you have listed all these priorities and then you ask for feedback, which a lot of executives do. But they don't do anything on half of them because they know what their priorities are. They may know them, they haven't communicated them. So to be more effective is to actually identify, communicate what those priorities are. Then ask everyone, every employee, what works, what doesn't work, where are their opportunities. Here there's a great story that everybody knows, the Stanley Quencher. Most people do. Right, the Stanley Quencher. And if you know much about the story, you know that there were these mommy bloggers in Utah who helped, you know, pick up the market and change things, but they don't know the whole story behind it. And Terence Riley, who's the CEO of Stanley. He had just come from Crocs where he had turned around things there. And he walks into Stanley. And at the time, Stanley is known for that green thermos that we have three of them in my house. You know, my husband keeps one in his workshop, you know, one in his camping bag. And. And they are 100-year-old company, 75 million in annual sales, and thinking the best days may have been behind them. And he asked the question, said, these are my priorities. And he asked the question, they had a true open door policy. And someone named Lauren Solomon, who was really, really young sales executive on the staff, came to him and said, I've been trying to get the execs here, Stanley, and to listen that I think there's this opportunity with the quencher, which they were about to like discontinue. So. So Taran said, well, let's do an experiment. Let's send them 5,000. Not a huge number. I mean, it'd be a huge number to me if I took those in, but not a huge number for Stanley. And they sold out like in an hour. And so they said 50,000. And then eventually 5 million. And now five years later, there are $750 million company. And when Terrence talks about this, he says it's because he didn't just have an open door policy. He set priorities. And then he asked what's working, what's not, and he made sure every voice was heard. So he even listened to Lauren Solomon, really young person on the team at the time.
Yeah. So I'm getting that the second step is do some deep listening of everyone involved, but set the boundaries and the priorities ahead of time and make sure that those are communicated because as you said, they're often not communicated. What if a leader says, but I'm afraid I might miss. If I just say these are the priorities, I might miss some really out of the box ideas that get cut off. How do you approach that?
Yeah, such a good question. Well, I think that, and I believe there's been a lot of research that backs this up and is that the people that are closest to the end user, the customer, the patient, the member, whatever industry you're in, they're often three people away, three levels away from the leader. And so while you can set these boundaries, while you can make sure these different voices are heard, there's a certain amount of trust that you need to give and empowerment to frontline employees. So to me, if you want to make sure that you're. You are staying on top of what is really happening out there? Those ideas are going to come from the front line. They're going to come from the nurses who work with the patients, from the barista at the coffee house, from the customer service rep that answers the phone. They are not going to come in the brainstorming session with the executives on the top floor. And so if you really want to make sure that you stay on top of those things, you've set your priorities, you have a focused team, you give some freedom within those priorities. But at the frontline level, you empower people to test and experiment with small ideas because they're seeing the emerging, they're seeing the patterns and the trends and the problems that aren't being solved and the customers that are leaving and not coming back and they're hearing, they're getting the earful from the people. If you can create, not only empower their frontline team, but have a system in place where people are allowed to experiment, they can repeat it, then they share it back with the team, and that gets shared up with you, then you can make sure that you're paying attention to some of the new things that are happening that are just a few levels removed from your role.
Yeah, yeah. And I do agree with you. When we see a leader who asks for feedback and they get all the feedback but nothing changes, that's where people get frustrated and they're like, well, why did you even ask for that feedback? So make sure that's why I do like this. Like, set the priority of the feedback that you really want to hear, because otherwise, you know, you get the feedback. You don't do anything people like, well, I told you, but you didn't care. So why should I tell you again.
And actually have a phrase for this? I call it, you said we did. So if you create a you said we did program, then back it up. You know, so if you're going to ask for feedback, you said this, we did this, or we these are the actions we took, or if we didn't, we didn't. Because right now these are the priorities. But we do think this matters, and we're going to be watching that to see where that. And that may impact the priorities in the future. But make sure that you said we did program at your. At your company or organization.
Yeah, great, great. So this last piece, take more shots, maybe just briefly describe what you mean by that. And then let's get into just one thing you would ask leaders to do tomorrow that impact their ability to be more innovative by setting boundaries.
Sure. Well, take More shots comes initially from my experience as a wildlife photographer. So first I tell the story that I started using film back in the day and I shot sports with manual focus camera. And one of my assignments was to shoot Michael Jordan when he played for the Chicago Bulls in the Eastern Conference finals. And, and you don't even know if you got the shot because it's not digital. So you have to take as many shots as you can. But years later, when I decided to become a wildlife photographer, I wanted to shoot one of the hardest things to shoot, which is a hummingbird. But while it's hard for other people, I figured this is not gonna be hard for me. I shot manual focus of Michael Jordan playing for the Bulls. I shot hockey, like, how hard can this be? But I would go out time and time again and I kept missing the shot. Like I shot thousands and thousands and I would completely miss the bird. In fact, I jokingly show this photo, this empty field and I'm like, this is my first photo of a hummingbird and it's not there, it just flew off, right. And so I started realizing that as a wildlife photographer you have to take more shots. It's easier today, right? Digital camera, my camera takes 30 frames a second. That's easy. But how does that translate back into the business world? As I started thinking about that, I was thinking, most companies, organizations, even a solo entrepreneur doesn't have 10,000 shots that they can take, but they can think about what are very small little experiments that I can do every day or that I could try, that I could learn rather than put everything into one basket. How can I iterate around this? And if you're a medium sized company, one of the great things that one of the companies I worked at, that we created was called the Best New Mistake Award. And there were awards at the end of the year where they gave out different awards. The top customer service person and, and you know, they had a variety of different awards. But the Best New Mistake Award, the value, the dollar amount was four times the amount of all the other awards. And you could self nominate and it's where you made a mistake but learned something from it and change things afterwards. That created that culture of taking more shots, of creating the culture where it's okay to experiment more often because just like me, I'm not going to get that hummingbird on that first shot. No matter what my experience is, no matter how skilled or how, you know the brand that you have that is beloved, you know that the idea that if you're going to launch something new. It rarely happens on the first shot. So it's going to take multiple shots and you have to bake them in. You have to build that into the culture.
Yeah, yeah, yeah. Great, great. So each of these steps together really make a difference. I love the concept. Where can people find out more about you and your work?
Oh, well, thank you. They can go to sherryjacobs.com which is my website. I also have my company website which is avenueandgroup.com but@sherryjacobs.com you could see some of the photos that I've shot, the award winning photo photos, the books that I've written, and a lot of this thought leadership that I've put on there as well.
Oh, that's great. And I definitely want to check out. I'm assuming you eventually got the hummingbird shot, right?
I did get the shot and yes, it's. It's still one of my favorites.
That's great. Well, thank you for coming today. And if you like this episode, you're not going to want to miss my interview with Jane Marvello, an entrepreneur and founder of Sarah Sacred Changemakers, a global community that focuses on human consciousness and helping people become authentic and human centered leaders. Let's lead the way. Hope you enjoyed today's episode and I'd like to point you to the next important step. Hit the subscribe button to get notified when we release new content. I'll see you on the next episode of the Enlightened Executive.
SA.
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