Jun 13, 2024 | 31 min read

Don't Pursue a Bad Idea to the End: Leadership and OKRs with Christine Sandman Stone

By: Patrick Emmons


OKRs are easy to set up badly. Christine Sandman Stone, CEO and founder of Deliver at Scale, focuses on this key element for success based on her years leading agile transformations. Beginning with her journey, Christine shares her path to leadership and the critical lessons she’s learned—and shared—along the way.

In this episode, Christine provides a glimpse into her world guiding teams to hone in on their goals. First, she offers her perspective on setting the objective and determining the quantitative measurement of that goal. Then, Christine shares the critical element of measurement periods (90 days!) and how to maintain the right outlook on pursuing these goals.

Christine offers key lessons from her book The Parent Track: Work-Life Balance Hacks to Elevate Your Career and Raise Good Humans on how to continue advancing your career during parenthood. She offers tips (ex. the word “conflict” is your friend) and her experiences that led her to share those lessons. Christine dives into her most recent book that set out to provide tangible resources for new managers: The Modern Management Mentor: Next-Level Tools for New Managers, inspired by the questions she fielded during her own daughter’s promotion.

Later in the conversation, Christine discusses the state of leadership and management training. She endorses the advancement of individual contributors that does not necessarily require managing people and discusses a multi-track approach. 

  • (1:38) – Introducing Christine Sandman Stone
  • (6:18) – OKRs
  • (9:35) – Narrowing in on the objective
  • (13:14) – 90-day measurements
  • (17:45) – The Parent Track
  • (23:20) – The Modern Management Mentor
  • (27:04) – Leadership development
  • (33:31) – Individual contributor growth opportunities

About Our Guest

Christine Sandman Stone is the CEO and founder of Deliver at Scale and former Global Head of Product & Engineering, Operations & Strategy at Groupon. She has previously worked with Dell, McDonald’s, and Volkswagen. Christine is the author of The Parent Track and The Modern Management Mentor. She earned her bachelor’s degree in philosophy from Miami University and a master’s in management and organizational behavior from Benedictine University.

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Podcast episode production by Dante32.

Full Show Transcript 


Patrick Emmons: Hello, fellow innovators. This is Patrick Emmons.

Shelli Nelson: And this is Shelli Nelson.

Patrick Emmons: Welcome to the Innovation and the Digital Enterprise Podcast, where we interview successful visionaries and leaders giving you an insight into how they drive and support innovation within their organizations.

Shelli Nelson: Today we're welcoming Christine Sandman Stone, a trailblazer in the world of business and technology. As a CEO and Founder of Deliver at Scale, Christine brings a wealth of experience in leadership and innovation. Prior to her, excuse me, start that over. Prior to her entrepreneurial journey, she served as the Global Head of Product and Engineering Operations and Strategy at Groupon, showcasing her wealth of experience and driving growth and strategic initiatives in a dynamic marketplace.

Christine's academic journey is equally inspiring, with a Bachelor's degree in Philosophy from Miami University and a Master of Science and Management and Organizational Behavior from Benedictine University. She is also a dedicated member of the Women's Mentoring Co-Op mentor and speaker program through Chicago Innovation, demonstrating her commitment to empowering and supporting aspiring professionals.

Join us as we explore Christine's insights on leadership, entrepreneurship, and fostering diversity and inclusion in the tech industry. Welcome to the show, Christine.

Christine Sandman Stone: Thank you. How fun to have a conversation with the two of you. Thanks for having me.

Patrick Emmons: Thanks for joining. So Christine, do you mind, share with our listeners a little bit more about Deliver at Scale, your role there, how it started, all it?

Christine Sandman Stone: Sure. 35 years in tech, I have worked for Fortune 500s, for smaller companies, and I realized that a consistent theme had been that I would get matched up with a leader who was in a new space, either significant growth or significant change. And I'm great at chaos and I'm great at bringing results out of chaos. So I've mastered things like OKRs, agile transformations. I love the work, and now I do it independently for leaders and for teams. I speak at conferences, I speak inside of corporations, and I love my work.

Patrick Emmons: Awesome. I understand you've got a big background of that. Tell us how it all started. How did that get kicked off?

Christine Sandman Stone: It started with a waitressing job, believe it or not. So I came out of college, I thought I would go to law school, and I started waiting tables until I figured out for certain what my path would be. And a fellow who came in with some frequency learned that I had a writing minor and he said, "Would you be willing to write sales proposals for me?" I had no idea what he did, I just said, "Sure." It was more stable than waiting tables. And it turns out that he was writing sales proposals for the very first Intel-based networks that were in existence, so things that no longer exist like Novell NetWare and Compaq SystemPro, these things that were at the very forefront of replacing mid-range and mini computers.

And my first day when I started, a fellow handed me a memory chip about the size of a piece of bread, and I was holding it on my hand and he was like, "Don't bend the prongs." Like, "Okay." It was a 16 Meg chip and it was $22,000 at the time. And I started writing this guy's sales proposals, and I'd be writing them and I'd be like, "That's not right. That's not going to work." So I'd go to him and say, "I don't think you're going to make the distance run from the office to the manufacturing facility. I don't think you have enough capacity. Have you thought about changing the bus structure and the server to get more out of it?"

And so, I became known for just having innate logical architectural skills, and I started doing architecture work to design data center projects. And pretty quickly I started to just run those projects. You how it goes, Patrick, right? You run the projects, and you're great at it. And they're like, "Terrific. Now we're going to give you all the big ugly ones." You're like, "Cool, fun." Then they say, Uh, could you rescue this one over here that someone else is doing that's in bad shape?"

So I went through that whole progression and started teaching others. And every step in my career, I went to Volkswagen, they had this remarkable management training program, and then I went to Dell and used every tool they taught me at Volkswagen to turn around to team at Dell. You get hired, and you think you talked about everything in the interview. And all of a sudden, you're week or two into the job and you realize there are 33 teams like yours in the US and yours is 33rd. And you're like, "Darn it. How did we miss that?"

But I turned that team around. We got them from... That was the first place that I really got to apply things in the center of chaos, so quarterly goals, unique goals and work alignment for every single person on my team, building deep relationships with technologists and customers. And by 18 months we'd moved up halfway to 17th, and three months later we hit the number one spot. And that team was ranked in the top couple of spots for years after I had left.

So the other part of Dell for me was learning do it right and it sticks, and it lasts after you. So everywhere I've been, the things that I've accomplished and done have stayed after me. So I've led agile transformations at McDonald's and Brookfield and most recently at Groupon. And I've also done expansive work in OKRs, which I just love, which has helped technology teams really figure out what dead weight to drop so we can ferociously focus on the things are going to drive revenue. Sorry, I'm getting nerdy about this stuff. I love it.

Patrick Emmons: No, it's all good. Well, I just want to make sure, I know what OKR stands for.

Christine Sandman Stone: Oh.

Patrick Emmons: But could you explain that a little bit for our audience?

Christine Sandman Stone: Absolutely.

Patrick Emmons: And to be totally honest, for me.

Christine Sandman Stone: Yeah, sure. So OKRs really came into prominence first with Intel when Intel used to be one of many chip manufacturers, and they set as their target to be the world's leading chip manufacturer. So with that goal in mind, they started setting measurements about how they wanted to break into markets, how they wanted to improve speed, things like that. And what they were able to do is by checking every bit of work against that goal and its measurement, the measurement is the most important part, they were able to achieve where they are today.

So the O is the objective or the goal, and the KR is the, and this is critical, the quantitative measurement of that goal. So if your goal in a current situation is to drive conversion on your mobile app, you set a target for what conversions are now and what you want them to get to. And as product owners work through their backlog and figure out what to prioritize, they're looking for things that are going to change conversion inside of the app.

Google used OKRs to grow to the mammoth organization that they are today, and a lot of people use them wrong and they set many multiple measurements, and then they end up in a twisted spaghetti of goal despair. But the ones that use them well have simple goals and then they're ferociously disciplined. And they're on time, we were talking about timeliness earlier, they're on time about checking measurements every month and then after a quarter of resetting. And that then lines up so well to your product backlog. So as you're starting to look at sprint backlogs, it's so easy when you use this pattern to start to look at features and say, "This one is definitely going to drive the number. We need to push it up to the top. And this one has a tenuous connection to driving the result. Let's bump that out of this quarter's priorities." It's a ferociously powerful way to manage engineers around the world. When I did it with, we have 1,500 product and engineering folks globally, and I could tell you what every squad was doing. It was pretty cool.

Patrick Emmons: Wow.

Shelli Nelson: Wow.

Patrick Emmons: And you mentioned that, forgive me if I misquote.

Christine Sandman Stone: Oh, go ahead.

Patrick Emmons: You said that quite often they're not done correctly, right?

Christine Sandman Stone: Correct. Yep.

Patrick Emmons: Why is that? What is the symptoms? Why do you think people do that? Is it lack of experience? Looks like I'm going to get a great answer out of that.

Christine Sandman Stone: Yeah. I would that running OKRs is like parenting; it's easy to do it badly, and it's really hard to do it well. Before we started, you talked about coaching and what you see when you can tell that parents are kind of loose at home, what you see with your athletes on the field. I would say that the hardest thing that a CEO and a leader has to do is they have to choose the target or maybe the two targets, and then they've got to knock it off. You can't have 19 top goals that everybody's working toward, that the dilution of focus and then the overwhelming bureaucracy of measuring all of that means you're going to fail. So I think the hardest thing for CEOs to do is be courageous, and founders to do this: be courageous, narrow it tightly, choose something you can measure, and then live it. It's hard work, but it's effective. The seven or six quarters that we ran it at Groupon, we were in the black during the pandemic. If that's not a reason to do it, I don't know what is.

Patrick Emmons: You talk about simplification. I'm with that, the idea of, "Hey, keep it simple. What's the most..." But it would seem to me, and my experience is that you've got to find the thing, that really root cause. What is that behavior? What is that? And that's not easy, right? Finding that, like, "Here's the thing that's going to make the difference," especially in a world where there's a lot of people who are going to say, "Hey, this is the important behavior."

Christine Sandman Stone: Right. Right.

Patrick Emmons: That we're saying, "Hey, we've got to have a hundred of these each week."

Christine Sandman Stone: I love that you're asking that question, because a critical part of objectives and key results is that you reset every 90 days. So if somebody's come up with an idea and they say, "I think this idea is going to drive a result," you check it 90 days. If it stinks, you drop it. But you don't pursue a bad idea to the multi-millions, multi-year end, because you're checking it so frequently during. It's why it's such a terrific pair to agile development, right? If something doesn't show viability at an MVP stage, it's gone. Don't waste more time on it. Does that help?

Patrick Emmons: Yeah, it totally does. I still think, to your point, there's an art and science of this type of stuff.

Christine Sandman Stone: Yes. Yes.

Patrick Emmons: There's also got to be humility.

Christine Sandman Stone: Yes.

Patrick Emmons: And sometimes that's missing.

Christine Sandman Stone: Right.

Patrick Emmons: Of admitting that they had the wrong call, right?

Christine Sandman Stone: Right.

Patrick Emmons: And they're still counting the wrong thing.

Christine Sandman Stone: Yes. But it's easier to be humble when your big idea doesn't work after 45 or 90 days. It's harder to be humble when your big idea fails when you release it to the market after 18 months of software development. So I would say that it gets easier for people to accept and maybe even celebrate quick identification of bad ideas when it comes fast. Otherwise, your professional career is wrapped up in the fact that you talked the company into doing something that was millions of dollars and a year or two long, and now it's not working.

Patrick Emmons: And it happens a lot.

Christine Sandman Stone: That it does.

Patrick Emmons: It does.

Christine Sandman Stone: It does.

Patrick Emmons: But to your point, I do think it's the culture as well that, "Hey, do we have a culture that really does do retros? And we are real honest with ourselves."

Christine Sandman Stone: Correct.

Patrick Emmons: And it's not a political landscape like many large organizations.

Christine Sandman Stone: Right.

Patrick Emmons: I've worked at many large organizations that, Six Sigma, these kinds of concepts. Right? I'm not saying which company, but I think everybody can guess, where it's like did they actually analyze whether it was working or not? Nope. Because the right VP said it's working, by golly, it's working. Right? But to your point, it will be transformative if these tools are used the right way.

Christine Sandman Stone: I agree.

Patrick Emmons: So again, I'm not saying they don't work, but I think that's the challenges when it comes to implementation is just without some of those key elements of humility and honesty and ability to pivot. So Sheli, I'm sorry, I interrupted you.

Christine Sandman Stone: Shelly had an idea, and then I have another thing that I'm going to add onto that. Shelli, what was your thought?

Shelli Nelson: I was just curious who came up with the 90 days? Was that measured? Is there data behind saying 90 days is when you should be able to determine?

Christine Sandman Stone: That's just the best practice of this process inside of technology organizations is that you just go 90 days.

Shelli Nelson: Got it.

Christine Sandman Stone: And the beauty of that is, is that when you're only going 90 days, you could only take something so far. So then everybody's getting really scrappy. They're like, "What is something that we can put in the app that could let us test this out quickly and determine if we should pursue it?" And then the idea gets beat up hard early on when you're trying to figure out how to do something in a small way.

Shelli, I know you're a student of human behavior as much as I am. The other thing too is 90 days is kind of a magical period for a human to make change. We know this from all of the data that if you've told someone, "I want you to improve your relationship with a particular team, and that's a goal for the year," probably they might not work on it until November. But if you said, "I really want you to improve your relationship with somebody and we've got 90 days," then you say, "Christine, how are you going to do that?" I'm like, "Uh. Maybe it's I need more updates. Maybe I need less updates and more space. Maybe I need to seek out other people and learn from them." But 90 days is not scary, right? You try something out and then at the end of the 90 days you say, "Did this help you build your relationship with the architecture group? Yes or no?" And if it didn't, you try something else. But 90 days isn't scary. It goes quickly. You get something done and you build on it.

Patrick Emmons: We've been following a similar approach that we do, and that's why people do quarterly planning, right?

Christine Sandman Stone: Right.

Patrick Emmons: It's also oddly the appropriate amount of time that the diffusion of attention happens, that you need to bring it back at that three months of, "Okay, we all launched month zero," and at about three months it's like, "Wait, are we still on track?"

Christine Sandman Stone: Yes.

Patrick Emmons: It's time to rethink, "Are we still on track?"

Christine Sandman Stone: Right.

Patrick Emmons: "Are we really looking at the right things again?"

Christine Sandman Stone: It's so healthy. Yeah.

Patrick Emmons: And it really does follow, and I think about it from a college standpoint, this is why we have quarters. This is why things are...

Christine Sandman Stone: Right.

Patrick Emmons: There's just a rhythm to human attention that if you go longer... And as a guy who's built a lot of software, those death marches-

Christine Sandman Stone: I know.

Patrick Emmons: "Hey, we're going to go get busy for six months."

Christine Sandman Stone: Right.

Patrick Emmons: And it's like by month four or five, nobody even knows what the hell we were supposed to build in the first place.

Christine Sandman Stone: Right. Right.

Patrick Emmons: Right?

Christine Sandman Stone: And the focus on... And since nobody's been measuring, everybody's still going on faith or you're going on, God forbid, personality, right?

Shelli Nelson: Yeah.

Christine Sandman Stone: There's one person in the organization who feels strongly and they're pressing. And so, everybody death marches. Patrick, you asked earlier the difference between people who do it well and people who do it poorly. My experience has been, it's like changing people from waterfall to agile. You've got to have a coach that's involved with the teams that's basically reinforcing behavior. So in OKRs, one of my responsibilities was to go through the drafts of everyone's OKRs, and no public shaming, right? You don't get in a big room and then tell people what the problems are. You go to them one-on-one and say, "Wait, walk me through this. I don't understand how this feature is going to drive this outcome." And it becomes just a supportive place to help somebody refine and build their muscle about doing this repeatedly. And without a coach, I think it's impossible, just like an agile transformation without a coach, it's impossible.

Patrick Emmons: Specifically, I do think analyzing what is that critical behavior, right?

Christine Sandman Stone: Yep. Yep.

Patrick Emmons: Because you've got to be not attached emotionally to the outcomes, right?

Christine Sandman Stone: Yep.

Patrick Emmons: And the public shaming, so I should stop doing that. That's your suggestion.

Christine Sandman Stone: Probably.

Patrick Emmons: But they're so fun.

Christine Sandman Stone: If the person being shamed thinks it's a great time, fine, fine.

Patrick Emmons: Well, if they felt that way, I'd stop. Then what's the value? Right? No, I'm just kidding. We do.

Christine Sandman Stone: You're funny.

Patrick Emmons: But it's funny how that still does occur. So I did want to ask about, you've got a couple of books as well. They're very different. Do you mind sharing with our audience the two books that you've developed?

Christine Sandman Stone: The first book is The Parent Track. I would speak in really big audiences about agile transformations, career progression in tech, especially to women in tech. And I put pictures of my family up or whatever. I would get to the Q&A, and the fourth question in someone would always go like, "I'm sorry. Could you go back? How the hell did you do it with four kids?"

And so, I started just sharing stuff that my mom would be so embarrassed if I was saying out loud. Oh my gosh, I'd put my kids to bed in their school clothes, so that way in the morning when we got up, nobody had to take off pajamas and get cold. In Chicago, this is a go-to strategy for parents of young children. I'm not kidding. We called it free-range feeding. We basically let them eat whenever they wanted if they were hungry. And it turned dinnertime cook prep, from an hour of hell into a really peaceful thing. Our rule was you've got to come and have conversation, but you don't have to necessarily eat. Eat when you're hungry. And our kids have grown up healthy and making good decisions about food. Little things, I would tell people, "Never, ever explain why you can't make a meeting if it's personal. Don't say, 'I can't make 3:00 because I'm in car line, I've got a pediatrician's appointment.' The thing to say is, 'I have a conflict.' Short. Short, neutral, and then everybody immediately moves on to the next thing."

Patrick Emmons: Before we move off of that, I'm curious because I'm just going to be real honest. 

Christine Sandman Stone: Yeah.

Patrick Emmons: I don't understand that it... So why is that important to not say?

Christine Sandman Stone: Well, especially for women, if we say a number of times, "I can't make that because I need to go to car line or whatever," we might find ourselves in the situation that I was in at one point where my boss, I was awarded a big project inside of the company and my boss actually declined it on my behalf. It was a career building project that I wanted desperately. He declined it on my behalf because he knew that my husband had been traveling a lot because I talked to him a lot about what was going on. I overshared. And so he told them, "Oh, let's give this to someone else."

I went to talk to him about it. I was like, "You know that project?" He's like, "Yeah, yeah, you got it." And I was like, "No, I didn't get it." He said, "No. You got it, and I gave it to someone else." And I was like... He saw my face. He's like, "Oh, crap. You wanted that?" And I said, "Yes." And he said, "But Christine, I know how busy you are. How would you ever fit that in?" I said, "I was going to finish this early. I was going to delegate this." He got the project back for me, and it was a career builder.

Patrick Emmons: Nice.

Christine Sandman Stone: And I kicked ass at it and it went really well. But later I realized, "Darn it, he did that out of a good spot in his heart."

Patrick Emmons: Sure.

Shelli Nelson: Yeah.

Christine Sandman Stone: "He was trying to protect me from..." He even told me, he said, "I don't want you to fail here. I want you to succeed. I believe in you." So he did it from a good spot in his heart, but it pulled me out of the running for something that helped me get a promotion later.

Shelli Nelson: Sure.

Christine Sandman Stone: So when we share details, people can start kind of factoring that into whether we're really ready to lead a team, like, "I don't know. She has to leave a lot at 3:00. Could she really lead a team if they need something and they need it at 3:00?" So why even give people data to doubt you?

Patrick Emmons: Yeah. No, I hear you. And I think that's good advice for everybody. You mentioned the oversharing.

Christine Sandman Stone: I think I did.

Patrick Emmons: Right?

Christine Sandman Stone: Yeah.

Patrick Emmons: Of like, "Hey, there's self-control of your own life and there's..." Right?

Christine Sandman Stone: Right.

Patrick Emmons: But I think that's really great advice.

Christine Sandman Stone: Absolutely.

Patrick Emmons: Because I do think especially with engineers, right? Engineers, they overshare a lot. They're awesome. They're very clear, they're very honest, and they sometimes do damage to themselves like that.

Christine Sandman Stone: Well, yeah, it's really helpful too to figure out who you're talking to on the other side. Because if you're talking to somebody who really wants the headline up front, you hit them with the headline and then you wait and you see if they need more data. I find a lot of engineers are wired to provide the history of the entire world that leads up to where we are right now. And sometimes that works.

Patrick Emmons: Yeah.

Christine Sandman Stone: I'm a headline person, too.

Patrick Emmons: Right. Just give me the headline. "Are we on fire?" "No." "Good. Let's move on." Right? "Is it on fire currently?" "No. We'll be on fire soon." "No, fine."

Christine Sandman Stone: The other part about the oversharing, when you've got to move something is it's not a good use of anybody's time. "I have a conflict" is three seconds long and we all move on to rescheduling.

Shelli Nelson: Yeah, great advice.

Patrick Emmons: Awesome. I'm sorry to interrupt on that process. I just wanted to make sure I understood.

Christine Sandman Stone: Yeah. So Parent Track. Parent Track, it's a mix of career, work/life balance hacks to elevate your career and raise good humans. I know it can be done. It is possible to do both. And honestly, we need the acceleration of one generation sharing their shortcuts with another generation so that we can pull it off. So it's really written for dual working households.

The second book happened when my oldest child reached out to me and said, "Hey, I got a job leading a team for the first time. I have four weeks to learn how to be a manager. What do I read?" And the books that I was thinking of were things like Dare to Lead, inspiration or Kouzes and Posner, this leadership tone that has all sorts of theory in it. But a 29-year-old does not need inspiration or theory; they just need to know how to get shit done, quite frankly.

So she and I started talking. She asked me to coach her and I'd start sending her things. I would send her things like, "Hey, here's a really quick way to get your first objectives figured out as a manager. Here are questions that you should ask your sponsor. When you meet your first sponsor, here's five questions you should ask them, eight questions to ask your boss before you start." And the book is called The Modern Management Mentor. It's winning awards, which is super cool. And because of my helpful Millennial, who was my collaborator on this, it is a paperback and it goes in your backpack. And it has some brilliant design work from my interior designer where tools are flagged in different colors. So that way there are 50 or more tools in here and you can just find them fast when you need them.

Patrick Emmons: Awesome.

Christine Sandman Stone: So I'm really proud of it. Thank you for asking.

Patrick Emmons: And can they find that on Amazon, I'm guessing?

Christine Sandman Stone: Amazon has both of them, yep.

Patrick Emmons: Okay.

Christine Sandman Stone: And then, sometimes when I work with corporate clients, they just buy them directly off my site, because then we can figure out discounts and delivery and line them up with workshops and things like that.

Patrick Emmons: That's fantastic.

Shelli Nelson: Congrats.

Christine Sandman Stone: Thanks.

Patrick Emmons: So how is your daughter doing?

Christine Sandman Stone: Oh my God, she's amazing. She's terrific. She's really terrific. And I think the thing that I learned from working with her is that a lot of Millennials want to be managers because they like human beings. And I would say that in my career experience, I've met a lot of people. I work mostly in tech, so I know a lot of Millennials in tech, but I know a lot of folks, my generation and the generations in between. And I think a lot of managers wanted to be managers because they wanted to make more money, and they weren't necessarily interested in developing people or making certain that everybody was delivering results and doing their best. So there's a fascinating opportunity emerging with these young folks who really have values at their heart, and they see leading teams as a way to live their values and make people's lives better and make the company stronger. It's pretty cool.

Patrick Emmons: I agree. I think the prestige, money reason. Lencioni, I'm sure that's one of the authors you probably thought about sending to your daughter.

Christine Sandman Stone: Right. Yep.

Patrick Emmons: And again, a lot of theory, a lot of good brain thinky. Right?

Christine Sandman Stone: A lot of theory. Right.

Patrick Emmons: But, "Okay, so what do I do on Monday?" Not a lot there, right?

Christine Sandman Stone: Right. Correct.

Patrick Emmons: But he talks about that, I think the title of the book is The Purpose, and it's about why people lead and why do people choose to lead.

Christine Sandman Stone: Right.

Patrick Emmons: Because leading is hard, right?

Christine Sandman Stone: It is hard.

Patrick Emmons: You get blamed for everything. You don't get credit, right?

Christine Sandman Stone: Right.

Patrick Emmons: If you're doing it right, you're really a glorified punching bag. And you've got to love the idea that you're developing a team and knowing that you'll get none of the praise. You will get all of the blame. But the other part, and I'd love to get your take on the concept of the gap of over the last 20+ years, how many organizations actually have leadership development programs?

Christine Sandman Stone: God.

Patrick Emmons: Right? So these younger people who do have a passion for service to others and wanting to be that glue, where do they turn? How do they learn how to be good leaders?

Christine Sandman Stone: Really good question. And I want to ask Shelli something as a follow-up to this. What I've observed is that budget cuts have impacted a lot of leadership development programs, and so they've really been paired back and shut down. And people expect you to find what you need on LinkedIn Learning, which is solid, but I don't think it's enough. I've been really surprised at the strong response by young first time managers and weirdly, very senior managers who are 25, 30 years into their career who like the book just because it's an easy refresher. You don't have to sit for three hours in a class. You find something that you need. Shelli, you work a lot with HR leaders across different organizations. What do you see in terms of leadership development inside of companies now?

Shelli Nelson: It's interesting, because I feel like a lot of the folks in our organization came through these great development programs early in their career at places like GE, right?

Christine Sandman Stone: Like GE. Yep, yep.

Shelli Nelson: And I don't see as many of those as I've seen in the past. And I can't think of a better playground to make mistakes and fail fast and move quickly, have mentors.

Christine Sandman Stone: Yep.

Shelli Nelson: It's such a great learning ground to touch all aspects of a business. And to me, at least the folks that I've hired, the folks I've talked to, that's been probably the best way that they got the experience they got outside of the classroom or outside of any books that they could read. And so, we're actually creating some of those programs now for general managers, so a GM acceleration program, things like that. So I see some companies kind of starting their own leadership programs, but I think you're spot on. I think over the past five+ years, the L&D budgets have been cut tremendously, and it's usually the first thing to go, which is truly unfortunate.

Christine Sandman Stone: I think it's bad business, honestly. If you look at an organization and you're trying to get results out of every single person and you want efficiency to be as high as possible and productivity to be up, it's the manager who does it, right? They translate the strategy in a meaningful way down to their team so their team can deliver results. But then, they're also working to make sure that we're getting the best out of each person. I think the managers are the layer that can be not just impactful to our profitability, but then create a pipeline for us as other dynamic leaders who had the gift of the leadership programs that I did, as they move out of organizations.

Shelli Nelson: Yeah. And I think the strongest companies too, they want to promote and develop their people. They're not afraid to let them go. 

Christine Sandman Stone: I agree.

Shelli Nelson: ... and move on within the organization; whereas other leaders might try to wrap their hands around their best talent and not want them to grow and develop. So the old saying, "People leave their boss, they don't leave their company."

Christine Sandman Stone: Right.

Shelli Nelson: So the amount of money it costs an organization for turnover, if anyone saw those numbers, they would be very happy to reengage their L&D budgets in my personal opinion.

Christine Sandman Stone: Patrick too, I know you focus so much on innovation. And the best companies that I've seen that innovate, actually the leaders, their hands are off. The phrase I love is, "Let the rabbits run." You tell the rabbits, "You've got this long and this much money," or "This is my problem, solve it." And that people who are closest to the code and the customer and the work that's going on, that's where the great ideas come from. They rarely come from the executive level. So there's such a cool opportunity here.

Patrick Emmons: My organization, one of our strategic focuses is leadership at every level. And I think tech changes every 18 to 24 months.

Christine Sandman Stone: It does.

Patrick Emmons: Leadership hasn't changed in 50, 60 years. Which one's a better investment? Right?

Christine Sandman Stone: And I would tell you, you know what hasn't changed in the last 40 years? Management training, and we've got to change it.

Patrick Emmons: Right. I agree.

Christine Sandman Stone: We've got to change it.

Patrick Emmons: I hear you.

Christine Sandman Stone: Because our strategies now, our targets change every quarter or two. Our people are global and hybrid and all these generations, and yet management is still pretty vanilla. There's an opportunity.

Patrick Emmons: Well, and the funny part is you see this again, I'll bring it back to sports because I think it's where's the highest stakes, Where is the highest investment? And you look at the NFL and you look at the new head coaches, the head coaches who are really having a huge impact in taking over.

Christine Sandman Stone: They're all young.

Patrick Emmons: It's not the Bill Belichicks. They're younger.

Christine Sandman Stone: Yep.

Patrick Emmons: They're known for their collaboration, not their command and control.

Shelli Nelson: Yeah.

Christine Sandman Stone: Right.

Patrick Emmons: Right?

Christine Sandman Stone: Yep.

Patrick Emmons: So they're able to bring in other coaches who can augment them. They're not insecure about it. And I think that's really where we see, even to your point of how we have to change leadership training. It's not about pointing and yelling and command and control, but collaboration.

And the one thing you've touched on, public service announcement, from my perspective, I see things on LinkedIn like, "Hire smart people and then get out of their way." It's like, "Then what's your job, leader?" Right?

Christine Sandman Stone: Right.

Patrick Emmons: "Your job is to set the goals, right? What is the strategy?"

Christine Sandman Stone: Right.

Patrick Emmons: To your point of we've got to figure out, "What's the meaningful OKRs?" We've got to dissect, "What is the tactics to achieve this objective?" And then have people go execute on those tactics and modify and evolve and all those things.

Christine Sandman Stone: Right.

Patrick Emmons: And I think that's where a lot of people, I see that like, "Oh yeah, hire smart people and get out of the way." And it's like, "That's not good leadership. You've got a job. And it's really important. It's really important."

Christine Sandman Stone: I agree.

Patrick Emmons: But the other part, and I think we see this a lot as people are developing as leaders. I was speaking with a CTO earlier today who had come up through the ranks as an engineer, and she's struggling with being an individual contributor and then moving to the executive leadership side and letting go a little bit. And she said, "I sometimes get pulled into it too often." And that's a natural process for high performers of you were great as individual or a manager level leader.

Christine Sandman Stone: Yep. Exactly.

Patrick Emmons: And then, getting the executive, it's like first rule is if you put your hands on the tools, you're not the executive leader anymore.

Christine Sandman Stone: Right.

Patrick Emmons: The second you've got to pick up the hammer, you've lost the role.

Christine Sandman Stone: It's hard, right?

Patrick Emmons: Sure.

Christine Sandman Stone: Because what gets you promoted is being exceptional at your role.

Patrick Emmons: Totally.

Christine Sandman Stone: And we walk into these new roles with confidence that can even drift into arrogance, that because we were so good at it that we know the ways things should be done. And the pivot to become a developer of other humans and to really be open to the best ideas coming from other people, it's really hard for an exceptional individual contributor to make.

Patrick Emmons: Well, and to that point, Shelli and I just had a conversation with Gene Kim, who's very big in the DevOps space, and one of the things he talked about in his study of great leaders is that one, they have a very high bar, right? So when we talk about the CTO we mentioned before, she's exceptional at everything and she's pushed herself and she just executes so well. And she's brought in, and I love the beginning of this conversation, where it's like, "Hey, you did a great group job. Your reward is a worst project."

Christine Sandman Stone: Ha ha. Right?

Patrick Emmons: "You get a worse team."

Christine Sandman Stone: Uh-huh.

Patrick Emmons: "Wait. Why don't I get a better team?" "No, and if you do well with this one, we're going to find an even worse one."

Christine Sandman Stone: Right.

Patrick Emmons: Right? "This is the prize, right? You get more pain." But one of the things that he brought up that I think is an important concept is one that they called that great at the big and great at the small. And it's like that you've got to be able to balance those two worlds of having high standards, being able to see the big picture from an executive strategic standpoint, but you still can sink down into coaching at that very tactical level. This is, to your point on the OKRs, what are those leading indicators that are going to feed into that OKR? And how do we, I think you used the word ruthless.

Christine Sandman Stone: Yeah, ruthless is a good word. I probably used it.

Patrick Emmons: Right. Executing on those leading indicators to achieve those OKRs.

Christine Sandman Stone: Right. Right.

Patrick Emmons: And it's a really difficult task, right?

Christine Sandman Stone:
It is.

Patrick Emmons: And just because you're great at doing the leading indicators doesn't mean that you're really ready for that kind of balancing the two worlds.

Christine Sandman Stone: Right.

Patrick Emmons: So it's definitely very interesting stuff. I think it's...

Christine Sandman Stone: I enjoy it, too.

Patrick Emmons: Yeah. Shelli, this is the best part about the podcast is having to have these conversations to talk about leadership and people development. And that's really when we talk about innovation or any kind of transformation, it's absolutely leadership, all of it.

Christine Sandman Stone: Yep.

Shelli Nelson: Yep. I think it's interesting. And Christine, I love your take. A lot of times we assume if people are really great at their jobs, there are going to be great people managers. And not everybody is cut out for that, and not everybody wants to be a manager. So I think the companies that do it well really assess whether or not that person is capable and wants to be in that space, or if they just want to continue to excel as an individual contributor.

Christine Sandman Stone: Something that gives me hope is I've seen a lot of technology organizations evolve and realize that it's okay for an exceptional technologist to not want to lead people. And so, they've built out these parallel career tracks, which didn't exist early on. Early on, you had to become a manager of things. And you were talking about the skills. I think if you think about a Venn Diagram, being a great software developer and being a great software development manager, they have a little overlap, but not a lot. It's like being a great salesperson and then being a great sales leader, really different skill sets.

And it's interesting, sometimes you can find the best leaders actually aren't your top individual performers because they're wired a little bit differently and they're deeply interested in bringing others along with them. So it's a fun space. I'm glad that tech progression has changed. I do still see, at least in the technology space, too often strong engineers get promoted and don't thrive as managers.

Patrick Emmons: Not given any training at all, just thrown into it.

Christine Sandman Stone: Right. Right.

Patrick Emmons: Like, "You were responsible for writing code. Now you're responsible for five people."

Christine Sandman Stone: Right.

Patrick Emmons: No training, no support.

Christine Sandman Stone: Right.

Patrick Emmons: 
How does this not work great? You've got people who chose a career that involves not talking to people for extended periods of time during the day, and they just don't naturally become garrulous.

Christine Sandman Stone: I was at a dinner the other night with a group of female CEOs, and we were talking about being a manager for the first time. And the conversation kind of went like this. One woman was saying, "I worked for the worst manager in the world, and I learned exactly what I didn't want to do. And I made mistakes anyways." And another said, "I worked for the best leader in the world and I was still tripping over myself." And we all agreed. The first year as a manager for all of us was generally ineffective, and we wished we would've had better support, because you don't want to lose a year.

Shelli Nelson: Yeah.

Christine Sandman Stone: No organization wants to lose a year.

Shelli Nelson: Yeah.

Christine Sandman Stone: And we all wanted to be good managers, and we still struggled.

Shelli Nelson: Yeah.

Patrick Emmons: It's awesome stuff.

Shelli Nelson: Which is why your book is so important.

Christine Sandman Stone: Thank you.

Patrick Emmons: Well, Christine, this has been a blast, obviously.

Christine Sandman Stone: Thank you.

Patrick Emmons: We really appreciate you coming on. I hope everybody else stayed on for the whole episode because this is just full of good stuff.

Shelli Nelson: Yeah.

Patrick Emmons: Christine, I just want to say thank you for taking the time. I really appreciate it.

Christine Sandman Stone: I really enjoyed the conversation with you both. I love the perspectives that you bring to this space, and I'm grateful for the time. Thanks.

Shelli Nelson: Thank you.

Patrick Emmons: We also want to thank our listeners. We really appreciate everyone taking the time to join us.

Shelli Nelson: And if you'd like to receive new episodes as they're published, you can subscribe by visiting our website at dragonsspears.com/podcast or find us on iTunes, Spotify, or wherever you get your podcasts.

Patrick Emmons: This episode was sponsored by DragonSpears and produced by Dante32.

About Patrick Emmons

If you can’t appreciate a good sports analogy, movie quote, or military reference, you may not want to work with him, but if you value honesty, integrity, and commitment to improvement, Patrick can certainly help take your business or your career to the next level. “Good enough,” is simply not in his vernacular. Pat’s passion is for relentlessly pushing himself and others to achieve full potential. Patrick Emmons is a graduate of St. Norbert College with a Bachelor of Science degree in Computer Science and Mathematics. Patrick co-founded Adage Technologies in 2001 and in 2015, founded DragonSpears as a spin-off dedicated to developing custom applications that improve speed, compliance and scalability of clients’ internal and customer-facing workflow processes. When he is not learning about new technology, running a better business, or becoming a stronger leader, he can be found coaching his kids’ (FIVE of them) baseball and lacrosse teams and praising his ever-so-patient wife for all her support.

Recent Episodes

We interview leaders from early-stage start-ups to billion-dollar enterprises who distill their lessons from their victories and their failures. Learn how these high-performing leaders organize their teams, establish a growth-minded culture, and leverage new technologies such as DevOps and Cloud.