- (00:00) Introduction to Leadership Insights
- (02:10) Christine Sandman Stone on Leadership vs. Development
- (03:18) Arne Saupe on Leadership Culture and Talent
- (04:54) Jorie Sax on Empowering Creativity and Innovation
- (06:19) Thulasi Kethini on Fostering Curiosity
- (08:26) Tony Newcome on Connecting and Supporting Your Team
- (10:43) Christine Sandman Stone on Setting Meaningful Goals
- (11:16) Arne Saupe on Vision
- (11:55) Tony Newcome on Mentorship
- (14:03) Christine Sandman Stone on Being a First-Time Leader
- (14:45) Conclusion: Reflecting on Effective Leadership
About Our Guests
Christine Sandman Stone is the former Global Head of Product & Engineering Operations & Strategy at Groupon. Arne Saupe is the former CTO at Farmer’s Fridge and newly appointed CTO at Wellfound Foods. Jorie Sax heads United Airlines’ Innovation Lab. Thulasi Kethini is the Executive Director and Head of Data Engineering at JPMorgan, Tony Newcome is CTO at ActiveCampaign.
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Full Show Transcript
Patrick Emmons: Hello fellow innovators, Patrick Emmons here. Over the years we've had remarkable conversations with brilliant leaders who've shared profound insight on what it takes to be a successful leader, whether in a startup or a global enterprise. Today we're bringing you some of the best moments, nuggets of wisdom from innovative executives on leadership.
We'll start with Christine Sandman Stone, former Global Head of Product and Engineering Operations and Strategy at Groupon. She reminds us that great development leaders and great developers aren't always the same thing. Leadership requires a different mindset and a different skillset.
Next, we'll explore the relationship between leadership and talent with insights from Arne Saupe, former CTO at Farmer's Fridge and newly appointed CTO at Wellfound Foods on how leadership culture can inspire and motivate talent.
Jorie Sax, Head of United Airlines' Innovation Lab will share how leaders can empower creativity and innovation.
Thulasi Kethini, Executive Director and Head of Data Engineering at JPMorgan will share how dev leaders can foster culture and encourage curiosity.
Tony Newcome, CTO at Active Campaign is going to talk about the importance of making time to connect and offer support.
Later in the episode we'll share some actionable leadership tips, including Christine Sandman Stone on why setting meaningful goals takes courage and decisiveness, Tony Newcome on how to reframe problems to unlock new solutions, and Arne on the value of building complementary partnerships in the C-suite. And finally, we'll wrap up with a simple truth from Christine Sandman Stone: leading this is hard. I think we all realize that one. So let's dive in.
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 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 skillsets. 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.
Arne Saupe: We are still at a space where what you do can actually be measured in percentages of company performance and other things. So tying it back to what it means to the company, and we're also small enough that you can actually see the people that use the tools that you're using or see the customer feedback and notice it, right? And so there's that. So we have a strong tie to what's happening, and we have difficult work to do, which means people feel challenged, we have ability to move people around, give them new experiences, stay in touch with where they want to go, and give them individual attention. That gets harder, I think, as the organization gets larger. But we're still small enough that we can know all of our people, know where they want to go, use our one-on-ones and make sure that they get experiences and challenges.
And I like to think of, as a leader of a team, you take on some of your team's personality, but they also take on some of yours, right? And if I at the top shoot for visibility, I screw it up, I'm going to raise my hand and say, "I made a mistake and this is what the impact was." And if somebody makes a mistake, I'm like, "All right, that's all right. You admitted it, we took care of it. Don't let it happen again, but we're okay." So giving people that's base to make mistakes, so even when the pressure is high they aren't constantly feeling like, "If I make one little thing wrong, the world's going to collapse," right? I have to make sure that I exemplify those things. And then I also provide them the space to make mistakes so when the pressure is high, they will perform and they will continue to push things out.
Jorie Sax: There's many ways to innovate, but everyone has the capacity to do it. I think sometimes it can be very intimidating. I know myself, I never saw myself as a creative or an innovator or a visionary. There are many days where I still don't. But it really depends on the context of it. And in the end, when you have the philosophy that we all have the capacity to innovate within our own respective roles and teams, you make the organization that much stronger and the future that much brighter.
And our Chief Customer Officer has a quote, "Inclusion propels innovation." And that's really important for us. That's how I've lived my career, to be honest. And I think the more ideas, the more perspectives, the better. And you can talk about frameworks for more of the traditional corporate innovation and what that means to be in a corporate innovation role versus a corporate strategy role versus corporate development or insert other team title or moniker here. But at the end of the day, if you're approaching things, multiple perspectives, you're thinking about it differently, you're throwing the rules out the window and just trying something new, taking risks, then you're innovating in your own way and you will likely land on some pretty surprising outcomes. And from that, you take it as far as you want or need or can go.
Thulasi Kethini:The way I look at it in assessment for my own team, or even when I'm hiring or performance review, any of these activities, or when I'm focusing on chatting with the engineer in a one-on-one, there's three things primarily. One is of course the technical competency. Are you continuously learning, growing? Do you know what pattern to use when? Are you producing good quality work?
And two is some level of leadership, which doesn't mean leading people, but are you a good team player? Do you have a sense of ownership? That's all leadership, right? And do you have the respect of the team? Are you able to respect different viewpoints on the team?
And the third thing is domain, which I refer to as business domain. Some engineers are very interested, some engineers are not that interested and that's fine. But there's a baseline of information you need to be curious about and know.When you're fresh out of college, it's different that, they don't know that they don't necessarily appreciate it and you're coaching them. But if you're to become a manager, you are the glue or you are the liaison between the business and your teams. And if you can't appreciate the challenges of your internal business folks, let alone external customers, if you're not able to ask the right questions, or asking questions is easy, asking the right questions is harder, and if it just doesn't happen, you need to have enough context to be able to ask the right question, and that comes with curiosity. And from there, if you can't do that, your team does not see you do that, they're not learning from you in that particular aspect, right?
So it becomes important for the team to appreciate or know what the business is to have a very efficient team. Pay less attention to story point velocity, pay more attention to what your business is about, what your customers are about, whether it's internal customers or external customers.
Tony Newcome: We would always walk away with a lesson and ask ourselves, "What went wrong? What can we take away from this? What could we have done differently to have a better outcome?" And I think that that just kind of relentless pursuit of, "No, we can achieve better than what we just did, this performance does not mean we are losers, it just means we happened to lose today." And I think that you've got to find that resilience somewhere. I mean, we certainly don't punish folks for making a mistake. I think that it's easier for me to convey that with the folks I work directly with. I've found as you're a senior leader, it gets really hard because you just don't have the trust when you're across 300, 500 people, you don't get that ability to invest as much time with each other to have that foundation.
And so I try my best to spend time with folks because I think those are real relationships you're building. And not spend time with them like solving a problem or expecting their work, but just talking with them so that then when there is something that I'm curious about or that they're struggling with, I can pick up the phone and they know that I'm really showing up to offer advice or offer support and not show up to hold them accountable, which when you're a senior leader, I think people always just assume you're the boss and so there's some kind of a problem when you're showing up and things need filtered before you hear it and that sort of thing. But I think you've really got to work hard to invest in those relationships with your team so that they will open up to you and that they will feel comfortable sharing.
And over time, for me at least, I see more and more and more people willing to open up and share their thoughts or reaching out to me and saying, "Hey, I just want to make you aware of this." I appreciate that so much because there's a finite amount of time in a day and if there's a fire somewhere in the organization, I will miss it if I don't have folks that are willing to raise their hand and say, "Hey, I noticed something doesn't seem right, I need help." And I generally try to open my questions up either in our one-on-ones with, "How's it going, what's on your mind?" And then my favorite question to ask is, "What can I do to support you?" And I think that a lot of times leaders are not, I think, offering that support and really should.
Christine Sandman Stone: 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 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 to be courageous and founders to do this, be courageous, narrow it slightly, choose something you can measure and then live it. It's hard work, but it's effective.
Arne Saupe: If the CEO provides a good strong vision of what they want that company to be and gets everybody to march to that, and then you've got your COO making sure that that concept is going to be profitable and we don't do ridiculous things that are going to blow tons of money, if you've got a good partnership there between those two, I think that is really a significant thing. So the strong visionary CEOs there that give a strong vision of what they want the company to do and where they want it to go, and then you have the responsible party on the other side, those two partners I think are very significant to have, and then it makes the rest of the people working in that organization able to execute on what they need to do to make those things happen.
Tony Newcome: The best advice I had from this, I'll credit my dad, he was an executive as well, and I was just very fortunate to have him as a mentor. I still have him as a mentor, but when I was younger, he would always tell me, "Tony," I'd say, "Well, this can't be done right?" I'm struggling with something, whether it was schoolwork or whatever, I said, "This can't be done." And he'd say, "Well, do you mean it can't be done or do you mean you're not quite sure how to do it? And those are very distinctly different concepts." And he said, "I actually think anything can be done, it's just a matter of whether or not you can currently see the path to do it." And he said, "In those moments, think of somebody who you believe could do the job. So you might be sitting there saying, "Well, I can't do this, but I'm sure so-and-so would be able to do this if only they were here," and then ask yourself, well, what would they do if they were here and then go try it, right?"
So a definitive bias to action I think is necessary to just go try something. You always hear about the cliches of, well, half of success is trying and you just get stuck in analysis paralysis. In a lot of ways it's true because you'll make that attempt and all of a sudden you'll learn something or learn why that's maybe not the right way to go.
The other thing that I've done many times, and probably some of the folks listening will recognize this, I will call people that I think would maybe know the answer and I'll just say, "Hey, sorry to bother you," and this is where I've invested time in them so they pick up the phone and I don't just use them to get answers, I invest time as just humans to be there for them too. And I'll just ask them straight up, "What would you do in a situation like this?" And I won't share necessarily details of what I'm dealing with, but enough to give them context to help me form my plan. And I think that call that a mentor, whatever you want to call it, I don't really go around saying, "Hey, will you mentor me?" I find that to be an awkward exchange, but I think that just the circle you keep should be filled with folks that you want to invest time with them, and then in turn, know that they'll be there for you as well. I think that's really important.
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. No organization wants to lose a year. And we all wanted to be good managers, and we still struggled.
Patrick Emmons: So much insight in these leaders' words. It was inspiring to revisit these conversations and reflect what makes a truly effective leader. I hope you found these takeaways just as valuable as I do. Thanks for listening, and we'll see you next time.
