Interview with Kate O’Neil, Co-founder & Head of Marketing at Teaming

Teja: Kate, so tell us a little bit about Teaming.

Kate: Sure. Well, I appreciate the opportunity. We recognize the need and the impact of great leadership on teams and being part of, you know, high-growth SaaS companies.

You know, the ones that really stick out are the ones that have had great leadership and being part of a great team. It’s such a rare thing.

When I think back on my career, there are a few teams that really stand out. We don’t think that should be the norm, right. If we’re all spending all this time together, we should make it a really effective use of our time and a meaningful one. So that’s really what the start of Teaming was.

We want to be good leaders. We want to work for good leaders and we want to have a really high-impact team experience. It’s grown from there, but for people who want that, that’s who we’re working with.

Teja: Yeah, that’s interesting. So the organizing principle of a team is a goal, a shared goal, or a shared vision. Right?

How does Teaming sort of help facilitate, you know, the creation and I don’t know, execution of a goal?

Kate: Good question. I think most people start with that. Right?

We’ve got all these ways to measure goals, and it’s important, right? It’s important to measure, our goals, and the impact our goals have, but we look at goals at a later stage.

An attribute of a really healthy high-performing team and the way that we’ve structured it is, you know, an effective team starts with psychological safety. From psychological safety, they’re able to have productive conflict, out of productive conflict, they’re able to drive shared commitment, from shared commitment, they’re able to hold each other and themselves accountable for a shared goal.

And that’s where you get to the goal piece of it, and then out of goals, right? What’s the point of having measurable goals? It’s to have a positive impact. So you want to measure whether or not you’re having a positive impact, not just am I getting these things done? You know, what are the trailing indicators of my work?

And then the last thing is, looking at, do the individuals of a team have personal purpose and meaning, those could be different, right? It doesn’t have to be shared. It could be, you know, “I’m providing for my family and that’s my purpose and meaning”. It could be, you know, the mission and values of the company that drives you. It could be all different things, but, we strive for, team members to have personal purpose and meaning in their work.

Teja: Hmm. That’s interesting. So, why did you guys choose OKRs as the unifying goal-setting framework?

Kate: Yeah. Good question.

Well, I think OKRs do a phenomenal job of making sure that you take something that is, meaningful. A mission and you make it measurable, and that’s so important, having those measures in place. Because it’s the only way to know whether or not you had a positive impact.

So that’s really what we’re getting towards, is being able to show that you’ve had a positive impact because that’s such an important part of being able to have purpose and meaning in our work. So that’s really why we drove the OKR model, but I do think there are other models. SMART goals, they could do a good job of that as well. It’s not to say that OKRs are the end all be all goal-setting model, but we did choose it because it’s simple and it’s measurable.

Teja: Yeah. I mean, I can tell you that we used to use this framework called the Traction framework and it’s similar to Rockefeller habits, If you’re familiar with that.

And the choke point we ran into was like, you set a goal that’s you know, in our business it’d be, let’s say like get X amount of people hired in a month from the network. You know, you sort of have to be prescriptive about how that’s done. And there’s no way to measure until the end of the quarter or If that’s done or not, there are no sub-indicators that give people direction and it became very hard as the organization scaled to give more tactical folks was guidance on whether or not they were doing the right thing.

Kate: Then they can’t find purpose. Right? And then they can’t find meaning and then they become disengaged.

Yeah, that’s tough.

We’ve had similar feedback from folks using traction, and yeah, Rockefeller was super successful, but, you know, I also think it’s part of finding your way.

The fact that you chose something, to begin with, means you’re working on the business rather than in the business. I think that’s step one of, you know, every leader’s journey is to say, you know, I need to dedicate a lot of time to working on the business. Something is better than nothing, I guess that is the point there.

Teja: Yeah. A hundred percent agree.

So then, you know, what’s sort of like the driving mission, for teams, is it like, I think the starting point was psychological safety so is that the end goal or is it that the business or the team will accomplish the goal with a higher degree of success?

Kate: Yeah. I think the end goal is that people are engaged in their team and that they find, what is a shared experience? That’s valuable for them.

So if it is the goal, that’s it. If it’s, you know, enjoyment of work, that’s it.

So yeah, vague answer, but I think if we were to say what’s the overall end goal? Yeah. I mean, we haven’t architected a deal this large yet, but we look at our customer base, any team can pick up Teaming. It doesn’t have to be an org-wide implementation of a large piece of software.

We see healthy high-performing organizations. A grouping of smaller, healthy, high-performing teams. And so, yeah, the ultimate promise of Teaming, and Teaming is a concept too, by the way, not just, the company, but, you know, companies can “team” really well.

In the past, we’ve looked at employee engagement as this individual measurement. Is Joe happy at work? Is Kate happy at work? You know? Is it fulfilling sustainability over time?

And we look at it differently, right? We look at, team engagement. If people are engaged in their teams, then employee engagement in the traditional sense goes up.

Teja: Hmm. That’s interesting. So the focus seems to be on measuring the engagement of a team through a series of goals, rather than the accomplishing of one particular goal over a finite period of time?

Kate: Yes, because the goal changes right? And it can change dramatically.

Also, I mentioned the concept of Teaming.

Our traditional sense and I think this is still changing today, but you know, I’m a marketer. I work in a marketing department.

Back in the day, I only worked in the marketing department. I didn’t work with any other departments now, you know, that’s changed quite a bit. I work with sales. I work with product management. I work with customer success, but I’m still in my department.

We see the future of work being, where teams are a conglomerate of people with different skill sets, working towards solving different business problems. Marketing might not be my number one team in the future. It might be, you know, enabling sales in the UK, and as a marketer, I contribute to that the customer success person contributes to that and we’re sort of centered around the business problem or the business goal and we bring different skillsets to the table.

Teja: How do you guys measure team engagement? And is that something that you guys measure as a function of your team?

Kate: Yeah, and I think anyone can measure team engagement. You don’t have to use the tool. Obviously, we try to make it easier for you, but we measure the attributes that I just mentioned.

For a single team, we measure psychological safety, productivity, conflict, commitment, accountability, et cetera, et cetera. It’s a simple anonymous survey tool that we recommend teams send every 60 days and they talk about them. They understand why these attributes are important to measure and then they come out with actionable ways to make each attribute better and then they set goals.

Ours is what we’re using for this model too, right. You know, how do I improve my norms and practices to be able to have more psychological safety, have better productive conflict, et cetera?

Teja: Can we go, as far as to say that goals are better accomplished if the first three things exist?

Kate: Yes. It’s been proven. There’s a lot of studies.

One person, in particular, who’s amazing, she’d be awesome to have on this podcast, Is Amy Edmond.

She sort of coined the psychological safety term, and she’s written a bunch of books on it. She’s done studies to understand the impact of psychological safety on teams, and their outcomes.

Teja: Okay. That’s super interesting.

You know, I’m curious, like how do you reconcile teams, let’s say at big organizations that are sort of notorious for like a lack of psychological safety, you know, that are high-performance organizations, with teams that have a high degree of psychological safety that are probably good places to work.

And I’m thinking like in particular about, let’s say traditional finance, or maybe at big tech, you know, Amazon is a great example, right. I don’t know if they index high on psychological safety, but they sure as hell index high on compensation and growth.

So, I would love to have a framework of how you think about that. Or if there are trade-offs there with growth versus safety?

Kate: Yeah, good question.

So I think of cultures, company cultures, as performance-based and learning-based and I think the ultimate answer right, is that every company has both in their culture. It’s just whether or not they prioritize one over the other that you feel.

Amazon’s a performance-based culture, Google might be a learning-based culture, although they’re probably a good example of a performance-based culture too.

you know, performance-based cultures aren’t bad, right? It is important to understand that, we’re all here to do something together and to measure that. Where I think the examples you used really get it right, is that they look at learning as a way to facilitate performance rather than in opposition of performance.

So, you know, in marketing, I use this example a lot, we do lots of things and we do it for the purposes of learning so that we can perform better later, not necessarily to perform to the highest standard right now.

So these are the examples you mentioned, high-performance teams that have low psychological safety, those teams can be really effective for a very short amount of time. They don’t have long-standing performance, it’s birdie performance, for lack of a better term.

If you look at all of those teams, and this is the work of Amy Edmondson, she particularly looked at surgical teams.

Surgeons, you know, run the show in the surgical room, teams that have low psychological safety in that group in a surgical room, they make more mistakes than those who do. You can have the best heart surgeon doing your work, but if they’re not able to facilitate a psychologically safe environment with the nurse and the PA and the resident, you know, everyone in the room helping to operate on your heart, you might be lucky to have a perfectly done heart surgery. If you look at all of those surgeries over time, there are more mistakes than in groups that might not have the A-class surgeon, but they do have psychological safety.

Teja: That that makes a ton of sense. And, you know, as I’m thinking about it, I may have even phrased the question wrong because psychological safety, it may be a function, not only of leadership but of recruiting and of getting the right people who are excited to work in an environment where comp is clearly a function of performance and there’s, you know, what is that Jack Welsh?

I forgot what they call it, but there’s like a thing where they would let go of the bottom performing 10%.

Some people may like that. They may want to work in an environment like that and they may feel safe. Like, “Hey, if I perform, I’ll still be here.” You know, it’s a different era.

One thing that I think about is, a lot of the traditional management books and learnings. If you go into like some big-name business school, they come from manufacturing or like, the organizations were very sort of hierarchical and the ability was concentrated at the top and they viewed the process as the main driver of value creation. People were interchangeable. They were, you know, the famous Adam Smith example of like a pin factory or whatever.

And today, the competitive advantage of any company is talent. How you actualize them and get them engaged, and it’s just a different world. Like everybody in the company is really smart and knows what the hell the company is doing.

So, that’s our background.

Kate: It’s so funny that you brought that up.

Our founding team worked for a company called LeanKit in Nashville. Steven Franklin is one of our co-founders, and then our former head of engineering and our former co-CEO, and me.

We basically, left that experience feeling like we had doctorates in lean process management and what was really unique is that you’re right, lean and lean manufacturing came about in terms of physical manufacturing.

What we were trying to do was help knowledge, work teams create processes and what we figured out was, lean has these two pillars, continuous improvement and respect for people.

And in, the manufacturing environment, respect for people meant safety standards and, labor working hours, you know, making sure that we are alright. Physically making sure that workers were okay.

But when you translate that to knowledge work, right. What does respect for people mean? Yes, obviously it means a safe environment, but I’m not worried about my hand getting cut off by a machine, you know, my computer.

We think, having seen teams that have really knowledgeable process management folks, the most knowledgeable process management folks, and comparing them to teams that might not be as mature in their process management, but they have really high psychological safety in our experience with our tens of thousands of customers at LeanKit the team that had high, psychological safety and a little bit of secret sauce, process improvement works better and more effective than the teams who really only focused on processing.

Teja: Yeah, that makes so much sense.

I mean, it makes so much sense because it’s not human beings doing the work, it’s robots that human beings make, you know? And so, for the robots to be built the people have to feel good.

That’s so interesting. I mean, as you know, we spoke to, I don’t know how many software companies in this podcast and that’s the one thing you can see is like, it’s no longer like, here’s our policy, everybody do this. It’s so much more collaborative these days.

Kate: Yeah and we think, we haven’t built this part of the app yet, but we’re looking forward to it is, so much of psychological safety and productive conflict is how teams make decisions. If you think about it, do you always make decisions with a decision-making model in mind?

Probably not. Right? Most people don’t, most groups don’t, most leaders don’t know to do that.

The speed with which groups can make decisions, to me, that’s the bottleneck to performance. You can perform better if you can make faster decisions, but you can’t necessarily perform better if you don’t take the time to figure out how to make good decisions, and how to have an environment where people feel safe to bring up a different opinion and have a voice in the decision-making arena, if you will. Otherwise, you’d just make bad decisions faster.

Teja: Totally, what’s your framework around decision-making?

Kate: I don’t know that there is one that’s better. It’s really being aware of the situation that you’re in. As a leader, helping to guide how a decision is being made, being aware of what’s happening on the team, and correcting as you go for the situation. That’s really vague, and hard, but I think, yeah.

Teja: Totally.

So, I’ll ask it differently. Jeff Bezos has a regret minimization framework that he famously articulated, which, you know, I can’t remember the exact phrasing, but he was like, “make a decision that minimizes your regrets. 20 years later.” So it’s a very risk-on approach, right?

It’s like when you can swing a big swing, bigger. Take the job, make the move, whatever you want to do, take the leap. I think that that’s a really powerful decision-making strategy for me.

I’m curious to hear, do you have something like that that you think about personally, not even as like what you put in the product, but you as Kate?

Kate: It’s funny that you bring that up. I wasn’t aware of Bezo’s model, but I mean, it obviously makes sense given.

For me, I think about a lot of decisions being a trade-off decision between your narrative, self, and your experiential self.

Like, what is the narrative that I want my life to be? I often think about which is probably not good, but, I often think about, you know, on my desk, Hmm, what would be my regrets? and what would I value most? So, yeah, regrets. but also, you know, did I live the life that I chose, or worked towards the life that I wanted for those years.

Then, your experiential self, sometimes those things are in conflict and then that’s what makes decision-making hard, but you just don’t realize that those things are in conflict, right? Like, I want to eat four tacos, but I also want to be a healthy person. So yeah, being aware of making that trade-off decision is probably my personal guide.

Do you have one I’m curious?

Teja: So, you know, it’s funny, a lot of the people that I admire for their business savvy seem to have some sort of method or process by which they measure data and they come to a decision, you know, and some, they like to go away to a cabin or something for a month and think about it. Some, make it fast if it’s reversible, like, I think that’s Bill Gates, his decision framework helped make, like irreversible decisions and reversible decisions quickly, which I think makes sense.

If you ask my team, they’re probably the better people to articulate this. I honestly think I try to minimize the amount of decisions I make every day, that’s what I really try to go for and I tried to never make the same decision twice. So my team will tell you that, like, if I have to repeat something, I’m not very happy about it because I expect if we make the decision, it should be this way. If reality changes, you know, we’ve got to readjust, but that’s the closest thing to my decision-making framework.

It’s probably something like, make every decision once, unless you’re wrong, then adjust. But if it’s right, just keep doing it, you know?

So, is your regret minimization, is that what kind of precipitated you to launch Teaming? Like, being in a high function of multiple companies prior and you kind of wanted to take the learnings from LeanKit and move in the direction against maybe instituting that process in a company?

Kate: good question. I sometimes think, why am I here? You know?

Teja: Well, we all go through that. Yeah. That doesn’t change.

Kate: Yeah, entrepreneurship is definitely the time in my life where I have questioned more than ever.

So I don’t know if you feel that way, but that’s been my experience. I felt like for my whole career, I wanted to be a marketing leader of a high-growth SaaS company or a technology company. I wanted to build brands that are unforgettable, that drive really amazing experiences for customers. I love the service part of it.

Marketing was my path for my whole career and LeanKit was probably the pivotal moment of like, this is such an amazing experience was such a great team. I just was fulfilled with where I wanted to go and I felt like we did all the amazing things that I personally set out to do.

So I was in this moment, I remember, my now co-founder, my former co CEO saying, “okay, you’re fulfilled in these things now, what, like, what’s your next step?”

And I’m like, “well, let me enjoy this for a minute here.” Like, I want to live. It was a moment where you’re like, oh my gosh, I do need to decide what’s next and that was probably two years before we founded Teaming.

so, I was drawn to this, because one, the team that I’m working with is great and we want others to experience that. So of course it would be a motivation for us.

And then, a challenge, right? Being a marketing person, I’ve always stepped into a company that had a product-market fit and there’s no place, I feel more comfortable. Then being able to drive demand from that point.

But from a marketing perspective, I’ve really learned to love finding product-market fit. And I have so much more appreciation for the startups that I’ve stepped into, where they struggled to find it and to get to the point where they were at to go drive demand. It’s been a really unique and challenging experience to get to this point and I love it. I look at everything from a marketing perspective and some so glad I’ve had the opportunity to be able to start something from nothing.

Teja: That’s so cool.

So you basically worked for the CEO and now he’s your co-founder, how’s the relationship changed? Is there like, are there vestiges of that old hierarchy or not? You know, I’m just so curious about how that works.

Kate: Yeah.

Well, so he’s our CEO now, too. So, there are four of us as co-founders, but yes. I mean, I don’t know if this is something that would resonate with you, but, you know, in the beginning, you’re all a team trying to figure things out and it is a more equal, dynamic, but you go through these things together and there’s a natural leader that comes out. He is that person for us. I think it’s been really good for our team dynamic to have that. It’s sort of like we added the team members dynamic to it, but also we have a natural leader, which, I think a lot of, I’ve heard this anyway, that a lot of founding teams struggle to find who becomes the natural leader out of the group and we kind of already had that going in.

Teja: Yeah. That’s so interesting.

In our case, I can even back up and draw it through-line to this notion of like, questioning entrepreneurship. So I will say that in our case, I’ve become more certain that I enjoy it over time, which is usually a good indicator.

When you first get started, you’re kind of like, what am I doing really? Like, was I put on this earth to make a website? Is that the highest and best use of my talents as a human being?

Then, I think over time, as the meaning becomes reinforcing because you build the team, they motivate you, they encourage you. You have to protect them. You have to grow them. You add more, you want to create and foster a great workplace culture. And so I think the meeting becomes self-reinforcing.

I started this company out of my old bedroom, in my mom’s house. I was like, yeah, I was like 24, you know? So it is what it is.

Kate: Have you read Julie Zoe’s, A Making Of A Manager?

Teja: No, I need to read that,

Kate: It’s really good. She was an intern at Facebook, she was a Stanford grad, she interned while she was there when she graduated, she joined full time, and she ended up being there, I think she just left recently, but she wrote about exactly that.

[She] started as a kid in this company as their first design hire, and then she grew to find so much meaning in creating a great workplace environment. The book itself is such a good, resource for people learning for the very first time, how to lead a team.

There are so many good management books out there that describe how they did it, and Making Of A Manager helps to provide a framework for you to create your own leadership style.

I don’t know if that makes any sense.

Teja: It does. That’s really interesting.

So, what’s on the 20, 21 roadmap for Teaming, as far as product goes?

Kate: So right now, I think we’re really good at helping managers run good team meetings, good one-on-ones to set goals, and to get into that cadence of measurable goals, and of course, to measure team health.

We also do, are you familiar with the disc assessment? You can take an assessment in Teaming, and learn a little bit about your style and the style of your teammates, and that’s in an effort to help build psychological safety. Communication is such a foundation of that and the disc really helps you be a better communicator.

So, those are the things that the app does really well.

We have this goal to be everything you need to lead a healthy high performing team. We hope that this year we’ll be able to add in some more fundamental parts of that. So one would be, feedback and recognition. How can we help people to learn how to give really effective feedback? How to receive effective feedback?

Then, recognition. How can people learn how to recognize others in the way that they prefer to receive recognition? We talked before we started recording about being somewhat introverted. I would rather die than have someone recognize me in front of a group.

We just don’t realize that sometimes. So that’d be one big functional area that we want to build out in the app.

and then, yeah, another one we kind of alluded to it, but it’s decision-making models. We definitely want more robust, intentional ways of people understanding how to make better decisions as a group.

And then, this is more technical, but I think it’s important, you have to log into Teaming to use Teaming. We never saw ourselves building an app where it was closed. We want to be truly integrated into the tools that teams already use; project management tools, chat tools, even browsers, to make it easier to do these things.

We have grand plans. My head of product management is probably gonna kill me for this, but we have grand plans to be into the voice space too. You know, we’re having this meeting right now. How can we analyze the conversation in a way that helps us to have a better one? Even just taking meeting notes.

Teja: Totally! And record the bottom line, just like, what do I need to do? Or what do I need to know? That’s really cool.

So the vision of Teaming is to basically be everything that a team needs to execute and work together.

What’s the world that you guys would create? Let’s say when you guys achieve like JIRA scale, like ubiquity, you guys are in every company, what’s that vision look like?

Kate: Yeah. Good question.

I think we would want to be a, you know, mission-critical part of someone’s fulfillment in work. We spend so much time working, If we can be an enabler of being able to find more fulfillment, more joy, and more effectiveness, and more growth for individuals, that would be huge.

If we can be associated with the idea of: we’re building better leaders, that would be huge.

Teja: That’s so cool. So, everybody can learn how to be a leader through the use of Teaming.

Kate: We’re starting, I’m so excited about this, the response has been unbelievable.

We’re starting a community of leaders, basically. Like I would foresee our content being people sharing real-life leadership experiences, real-life failures, real-life questions about not knowing what to do so that we can learn from each other in real-world practical application.

No fancy titles or, you know, research projects behind it necessarily. I mean, maybe we’ll get into it down the line, but, I think we’ll find some more approachable ways to learn leadership and the community aspect of it.

Leadership is lonely, so being able to connect with people like you in similar situations, and being able to ask questions that we often can’t ask in our own environments.

We are expected to know the answers from our managers. We can’t ask our teams because. You know, w how we’re trying to get better and they don’t have, you know, they haven’t learned the skills yet. And perhaps we don’t have peers that we can talk to in an organization.

Teja: Why is leadership lonely?

Kate: Good question.

When you first become a manager or your very first time leading a team, it’s naturally alienating. The power dynamic changes where you are, the person that people look to decide things, to set the example, and it’s this unique set of people.

Everyone has a different set of people that they’re leading. So, you can talk about some shared experiences, but ultimately you’re leading this group of people there in your charge, you’re taking care of them, you’re reliant on them, you’re supportive of them.

No other person has that specific experience of leading.

Teja: Yeah, that’s so true.

I definitely agree. It’s lonely, but I haven’t been able to pinpoint why. You can’t talk about it to any of your friends. You can’t talk about it to your significant other. You can’t really talk about it to like your investors.

Kate: How important is that though, right?

You spend how many hours a day in that lonely position. How important is it to find some outlet for or at least being around people who have a shared experience? It makes me a better leader, I don’t know if you’ve found that, too.

Teja: Yeah, it does because it helps me just be like, “Hey, this is normal, you know, it’s not abnormal to feel this way.”

And I think, especially because entrepreneurship and leadership are so lonely, I need level-setting conversations to be able to contextualize my own experience.

Kate: I call it, I’m getting wrapped around the axle.

Teja: Yeah, exactly.

So since you run a business, you probably, even after dinner, you’re thinking about work. How do you disconnect and say, “Hey, okay, it’s time for bed, we’re going to pick it back up in the morning”?

Kate: There have been lots of sleepless nights, so I’m not sure I’m good at this ao take that with a grain of salt.

I think putting the phone and the computer down when 10 o’clock comes. If I haven’t put my phone down by like nine forty-five, I’m not sleeping. It’s just not gonna happen. I need consistency in my schedule.

Sleep for me is a big one. I have to be asleep by 10 30, otherwise, it’s just going to be a bad day the next day.

Teja: Yeah!

Well, Kate, I really enjoyed it. It’s awesome getting to know Teaming and get to know you, and you should come back. I would love to do a demo of it on air. That’d be really fun, so.

Kate: Oh my gosh. I would love that.

And same. I’m so glad we’re connected, Nashville tech is so hard to come by these days.