Building Teams That Challenge Ideas | Karan Yadav

[00:00:00] For me, I know that no amount of experience is a validation of the person's probability to succeed, right? I am evaluating that person in an interview for their behavior, not for their experience. I'm validating experience, but I'm evaluating on behavior. I'm Felicia Shakiba, and this is LeaderbookAI, where we solve a business challenge in every episode.

[00:00:28] Karan, thank you so much for joining us today. Of course. Thanks for having me. We're excited to chat about this because I think that this is a subject that we can never get 100% correct. And it's something that comes up over and over again. But before we jump into it, I want to talk a little bit about your work and your history. You were at Workday and Apple, and you are scaling teams at Orbit Shift today.

[00:00:58] Right. We're going to talk about friction and how to make better decisions, something that nobody really can nail, I think, from a leadership perspective. Yeah. You learn all the time with that, right? So the hope is that you keep getting better every time you do it all over again. Yeah. So how do you just stack up your learnings over and over again and hope to be a better leader as part of that process? Absolutely.

[00:01:25] What about this subject is important for you? Why is this important to you? So I've built and led teams in Fortune 500 companies, post-IPO scale companies like Workday, and very, very large companies like Apple. And there are some consistent problems or challenges, if you will, with scaling, right, with building teams.

[00:01:52] And I think we all could get better in the way we do it. So now I am at a seed stage startup, and the problem is very similar in some ways that you would have at a Fortune 500 company. So it transcends what size, what scale, what maturity of an organization you are a part of, and you have to solve this problem regardless. Yeah. I think that's a really good point.

[00:02:16] I think some people think that friction is heavier in, you know, bigger corporations because of the red tape, because of the hierarchies. Right. But really, friction is a part of humans, and it doesn't matter the size. I think maybe the friction differs slightly. Different flavors, you're right. Right, different flavors.

[00:02:38] What would you say is the, you know, the biggest differentiator between a Fortune 500 or a large organization versus a startup? How does the friction show up differently? Yeah. So for a large organization, you've done a couple of things, right? Right. Your product has delivered, and, you know, you have a size of an organization where you have a large set of accompanying resources to help you. You have a full-fledged recruiting organization.

[00:03:06] You are a brand that's well-known. You attract a great amount of talent because people want to work for a great brand. That part is taken care of, but now the challenge is how do you work through the complexity of an organization to hire fast? Still be creative, yet, you know, trying to stay within a description. And the problem is, you know, the other flavor, if you will, of friction on a startup side is very few people know who you are.

[00:03:36] They're trying to figure out, you know, if this is a company worth joining. Is the product market fit there yet? You know, of course, there is also the element in a startup where, you know, the founder culture drives a lot of how you are experienced might end up being. So you are always taking a risk and a gamble at that standpoint. So different elements, right?

[00:04:01] You get freedom to operate in a startup, and if you join, you get great experience because you're now part of so much bigger than in terms of just your job description. And, of course, in a smaller organization, it's a different flavor of that piece where you have a job description and executing against it. So I'd say, you know, both as an individual, if you're joining an organization and as a leader, if you're hiring, you just have to focus on what's valuable for the person you're recruiting. Right?

[00:04:30] And if you can connect that value for them in a way that makes sense, you've probably, you know, taken the first step, right? And then it's all about how do you then nurture them and make sure they feel part of something that's bigger than themselves. Yeah, 100%. Tell me more about your role at Orbit Shift and how friction shows up within the work that you do as a leader. Yeah. So I am the chief operating officer and head of Americas at Orbit Shift.

[00:05:00] And really quickly on Orbit Shift, we are a sales intelligence and a sales orchestration platform working with global 2,000 companies across the technology industry. And we started about four years ago. And I just recently joined the organization about six months ago. And my dream, it really clearly is, of course, scaling the business here in North America amongst other COO responsibilities.

[00:05:30] So really, if you think about an organization that's literally four years old, and of course, we are backed by some well-known VCs that we all know, the idea is my job, number one, is to scale up the marketing function and the sales function. And on the sales side, you really need very specific kind of behavior that you need to hire for, for them to be successful in such a young organization.

[00:06:01] One, we don't have a well-prepared playbook yet. We are still in an early stage. We know we have a great product. We know we are solving large problems for our customers. But do we have a repeatable playbook that we think we can hand over to a salesperson and say, go execute? We're not there yet. Do we have a well-orchestrated marketing engine to actually bring in leads so that we can start executing on those leads? We don't have that yet either.

[00:06:30] But do we have the opportunity to scale significantly and keep growing at 3, 4x multiple that we're growing at? Yes, we absolutely do. So you need someone who's entrepreneurial, is kind of ready to grind, if you will, to kind of really work through the challenges, figure things out.

[00:06:53] Because my biggest, you know, and I tell that in almost every interview I do, I said, my expectation of you is to keep trying. And the moment we stop trying, we fail, right? And as soon as we figure out something that works, let's take that and repeat that multiple times because that's what sales do. Now, marketing problem is exactly the opposite or a little different on the other side.

[00:07:18] Because for marketing, you're trying to figure, okay, how do I get to my persona, my ideal customer profile, repeatedly and more effectively with a statement that will resonate with them? Right? Right? Identifying those cohorts of people, getting the message right, getting the machinery working from demand generation to thought leadership to product marketing. All those pieces, they're all frictions of both growth and learning at the same time.

[00:07:47] So you need someone who actually comes in with just almost the passionate zeal to solve for these problems. No matter who you are, whether you're marketing or partnerships or forward deployed engineer or a salesperson, as long as you have that, you'll not only be successful, you'll just be adding to some, you know, adding amazing value to a startup. At least for the startup of our size. Yeah.

[00:08:14] When you talk about, like, these are the most important characteristics for maybe a startup, maybe at Orbit Shift, why not knowledge, experience, you know, be at the forefront? Or is that? Or is it equally important when you're recruiting? Tell me more about knowledge and experience. In what context you're kind of referring to?

[00:08:37] So if you're, I mean, if you're recruiting and you're recruiting for people that kind of fit the culture, that can continue to try, that has grit, I might say. Yeah. Dealing with ambiguity is kind of a big one, right? Yeah, 100%. Would you say that those are more important or equally as important as, for example, hiring for someone with nine years of experience versus one years of experience?

[00:09:01] Because if you think about AI and how quickly we're able to catch up with skill sets and knowledge, depending on how well you know how to use AI.

[00:09:14] Do you pick the person with grit and passion and ambition that maybe only has one or two years of sales experience or even no sales experience versus someone that doesn't know how to use AI with nine, 10 years experience? That is such a good point. And I have to say I haven't cracked this yet. And I'll tell you why I haven't cracked it. Or maybe I'll give you my excuse if I haven't cracked it.

[00:09:42] So why do we hire, when you hire for a salesperson or a marketing person, why do we look for certain patterns in their resume? Yes. Why? Because we want to risk mitigate, right? Right. Hey, have you been in a part of a startup that you've grown from, you know, 5 million to 50 million? Oh, great. Then you'll be a great fit. You know, of course, assuming everything else fits in. So I believe our resume is a risk mitigation strategy for almost everything we do from a hiring standpoint, right?

[00:10:11] So we are trying to pattern match their experience to what we expect. And that's why we look for certain, shall I say, profile, right? Five to 10 years of experience and ability to have worked in a startup selling to enterprise customers, this size of deals, speaking with CXOs and such.

[00:10:31] I would love for AI to get to a point where I can abstract all that and can really evaluate an individual on their characteristics rather than their resume. Yeah. Funny story, I'm speaking with one, currently we are rapidly hiring.

[00:10:50] I'm speaking with one gentleman who's been a car salesman for 10 years and then kind of joined a software sales organization for the last four years. Great guy, right? And if he had not done the last four years, I think he still would have been a wonderful guy to join, you know, software sales. But somebody had to give him the opportunity to make that transition. Yeah. And I don't think those opportunities happen often enough.

[00:11:20] So I honestly don't have an answer to what you're asking, but I think it's such an existential problem. One, because I think what's happening with AI is the on-ramp for young graduates to join the workforce is getting harder and harder. Oh, yeah. So if we can solve for that in a meaningful way, that'll take care of a lot of things.

[00:11:42] And of course, for me, I know that no amount of experience is a validation of the person's probability to succeed, right? I am evaluating that person in an interview for their behavior, not for their experience. I'm validating experience, but I'm evaluating on behavior. But what am I letting go of if I'm pre-selecting a certain criteria, you know, from an experience standpoint? Yeah.

[00:12:08] And that's the part that I have not been able to crack because then it becomes a scale problem, right? Now, instead of getting 100 resumes, we get 1,000 resumes. Yeah. And then how does our team really work through that? So if there is a better way of doing it, I'd love to know because I know we are missing a great amount of talent because of that self-selection into certain segment of experienced candidates, if you will. Yeah. Yeah.

[00:12:32] I do think that talent acquisition definitely has their work cut out for them for the next few years. I mean, AI is definitely leveling the playing field in regards to knowledge. But I do think that experience and being able to make decisions in a moment's notice or, you know, adjust more quickly or how we use AI to, you know, what questions are we asking it, those things.

[00:13:00] I mean, I think that those are the types of things that are going to maybe start to surface more in interviews and understanding like, well, what would you do in this situation? Yeah. And more so than what have you done in the past, which is interesting in the conversation of its own.

[00:13:19] But with that being said, a lot of new people, new perspectives, new experiences come into the organization and they may not always align with the vision or mission or how you do things. So if we took someone that's new and came into the organization and they were kind of going against the grain, what's your approach to that?

[00:13:48] So I'm a big believer in dissenting voices and having a different viewpoint on how to do things. Because I think if we are, you know, cultivating everybody agrees idea kind of our culture, then we are completely missing on different ways of doing things. So first of all, I want my team to dissent, disagree, propose new ideas, think of new ideas.

[00:14:15] But as long as the fact that once we agree on something to do, we all go in the same direction together. I also think there is a way of disagreeing that not a lot of people kind of understand, right? So you have to really navigate how you disagree, right? In the sense that it's an art that you build over time, right? And I think that comes with experience.

[00:14:41] But if there is something that especially younger generation can understand is how exactly do you present your case and present your disagreement and how do you want to go about it is as important as disagreeing itself because sometimes it doesn't come across as they intend it to be. And the third part, really, especially from a startup perspective, Felicia, is you have so little time, right?

[00:15:08] You are fighting for existence every week, every month, every quarter. You have the great opportunity, but you also have, you know, we all know what the success rate for startups typically is, right? So you do not also want to get to a point where someone has a completely orthogonal way of doing things because, you know, in a startup, you can only figure out a couple of ways of doing things and then you have to make sure that scales.

[00:15:39] So, and at that point, you probably realize you probably not made, you know, the right hire because the idea is the startup is not going to change strategy because someone has joined and then we go in a completely different direction because we have only those many resources. So I guess there is almost a sliding scale of that descent, right?

[00:16:02] So I'd say, you know, anything that helps the organization be a better version of itself and drive the outcomes that it needs to drive in a, you know, somewhat of a short duration, because again, as I said, you don't have, you don't have much time and the way you descend, right? I think that's, that's really kind of could actually be easier in a way that you could descend more by being, by descending better. But beyond a point, it doesn't make sense.

[00:16:28] Then it's like, okay, you have some other ideas that doesn't align with what the organization wants to do. And at that point, you have to part ways. Yeah. Yeah. There was something that you had said to me called rock tumbling, which I actually know very well because I have a rock tumbler. But I want to know what, where does this phrase come from? And if you could explain it a little bit better. Yeah. So I got introduced to rock tumbling while I was at Apple.

[00:16:58] And the simple idea at Apple, Apple culturally is probably the most unique organization you can ever work at. And the couple of things that are relevant from an Apple standpoint in terms of when you're evaluating an idea. There is, you know, when you get onboarded, you get, you get shown this video that of course came from Steve Jobs' school of thought, which was a thousand no's for every yes. Right.

[00:17:26] And, and the idea is it takes, it's harder to say no than it is to say yes. So how do you get to that 1%, 0.1% yes, if that is indeed has to be an yes, you, you, you rock tumble the heck of that idea. Right. You continuously pressure test it internally as a team, then collectively with your, with the teams that you're going to work with, with your partners, with your customers and see if there is a validity in that idea.

[00:17:55] And on, even when there is a validity in that idea, imagine Apple is such a large organization. It has a hundred other priorities to think about. So where does its tank rank in terms of your, the other priorities that you might have to compete with? So, so the idea of rock tumbling is you having an idea is just the beginning of what you could be working on. Continuously working through it and, and refining it and then pressure testing it and working across your ecosystem to make that work.

[00:18:26] You, it makes you, it makes you so much effective and kind of really not about having an idea, but actually thinking 10 steps ahead as to what that would mean is really what rock tumbling is all about. So you, you tumble the rock to a point where it just, you know, the edges are taken care of and it's, and it's, you know, in the shape you would want.

[00:18:46] And, and the interesting part of that rock tumbling Felicia is it makes you such a better student of how to really take an idea, you know, from its inception to execution. And what you also realize is if your idea doesn't go forward, it's not the end of the world because you will eventually see your ideas show up in different versions of a different idea. And you realize, ah, it didn't happen the way I expected it to, but it did happen.

[00:19:14] And, and, and of course that takes years of, uh, patience and, and, and, you know, and kind of really understanding how a company like Apple works. But I think a rock tumbling shows up in almost all organizations in different kinds of ways. But, uh, of course I think having a front row seat at Apple and really seeing that happen was quite fascinating. So you've sold me on rock tumbling. I'm, I'm, I'm there. I'm with you.

[00:19:42] I'm going to play a little devil's advocate because there are some people that are not super excited about AI maybe taking their job one day. Right. So these new ideas that come into play around leveraging the technology, um, knowing how to use it and maybe even using it more efficiently could take someone's livelihood.

[00:20:09] So people are not so bought in on these new ideas around AI, I think is the biggest challenge today around dissent. How do you handle something like that in an organization? I mean, we, we obviously want the new ideas, but when it comes at a potential cost. Yeah.

[00:20:32] It's such a, it's such a hard topic to discuss because a couple of ways to, you know, to, to process it. So one is the organizational way of processing it, right? So as if you are working for an organization, you are working for a for-profit entity that's trying to maximize, you know, its outcomes as much as possible. Be more efficient, you know, be more productive. And they will use any tool in the toolkit to be able to get themselves there.

[00:21:01] I know it's gut wrenching to see kind of the, on the other side where, you know, you're not able to hold as many employees as it's possible. But that's, this idea of technology driven productivity is, is as old as, you know, organizations themselves, right? We had the same situation with the printing press and assembly lines and telephones. Right.

[00:21:24] But of course, AI is fundamentally more transformative than, than all the technologies that we've, we've spoken about. I think, and I'm, I'm going to give you this perspective from an organization that is AI native, that is of course, you know, selling tools to help salespeople be more productive and more effective.

[00:21:49] And I'm, I'm going to abstract that in a, in a way that hopefully addresses almost all different AI tools. I have a feeling that AI is going to create an air pocket of, you know, labor reshuffling or labor realignment, which will be painful.

[00:22:11] But if we truly believe in the fact of human ingenuity and then our ability to actually think ahead and think forward with AI, and that might create more opportunities than we are actually thinking it would. Right. So of course there is, there is the doomsday say of camp, which says you will not have any jobs and AI will run everything. I don't think I believe in that, to be very honest, because I haven't seen that yet.

[00:22:39] And maybe that is just around the corner, but we'll see. But I really, truly believe that if you are a young professional or about to graduate, you have to think about how you are going to be the most effective employee with AI agents as your coworkers. Right. How can you harness the power of AI to, to, to deliver that outcome?

[00:23:06] It might sound corny and you probably, you know, it's been said so many times, but I really believe that because I can see that on a day-to-day basis with my team as well. Right. You can clearly differentiate one who's using it effectively to who's not using it at all. And through three, who's, who's completely just given up and only using it. Right. So the AI slop part is also very real. So I really put all the, all my team members in those three buckets.

[00:23:32] And, and I think the first bucket, the person who's actually using it super effectively, still keeping their original intent on. And, you know, everybody can write a thousand paid essay right now. Right. With the same single prompt. But how can you write that thousand, a thousand word essay with your core thesis in mind? Right. I see this on, on LinkedIn, for example. Right. There's just so much AI slop. Right. Every, everything being written sounds so similar.

[00:24:03] Yeah. The, the originality is gone. Yeah. How can we, how can we still use AI and not lose our originality? Right. Not use, not lose the intent of what we wanted to communicate. So, so I think that piece, Felicia is still missing, but I think someone who can actually be that best of both the worlds is really going to be the future leader in our far times. Well, we'll see. We'll see who it is.

[00:24:30] But I, I do think that dissension is a big part of that. It's around authenticity, originality, bringing new ideas, creativity, you know, do we need more of that? How do you get more of that from a leadership perspective? I mean, a lot of companies are so used to, um, this is the way we do things.

[00:24:56] This is our culture where it's very difficult to, to do a 180 on culture. But how do you, how do you get an organization that doesn't know how to get more creative and original ideas in the past to, uh, an organization that breeds continuous learning and, uh, and originality or creativity? Yeah. It's hard. It's super hard. The larger the organization, the harder it gets, right?

[00:25:23] Because you have, you have that legacy of culture built in, whatever that culture is, right? Um, and, uh, and if you haven't embodied creativity and, and disagreement right at the outset, it gets harder, exponentially harder as you grow.

[00:25:43] So, so, so if you are a startup founder today, um, you know, one thing I'd say is make sure you are hiring people with, with originality and creativity in their, in their core DNA, because you would need that more than ever, um, going forward. And, and, and the, the, the more you hire folks who tend to very quickly agree with you is going to, you know, is going to be actually very costly later down the road.

[00:26:12] If you are a large organization and who's going through this transition, I can feel, I can truly understand how hard it can be, right? Because turning around a big, big ship is extremely hard. So it has to start from the top again. Um, no surprises there, but, but how do you, how do you get yourself?

[00:26:35] And I, and it's, it's the same thing by the way, when you, when you look at a company that's as a legacy product and now trying to, you know, make itself more relevant in the world of AI, right? And essentially what it's doing, it's, it's layering, putting another layer on top of its legacy. Culture is much like that, right? You want to, you want to put another layer of disagreement and dissent, but that, that won't work because in at its core, it is so hard to uproot the core set of principles that you've built yourself on.

[00:27:04] But regardless, I think back to your point on dissent and creativity, those are timeless principles, right? No matter where you are. So if you, if you, even if you're building an organization 50 years ago and you weren't focused on that, you probably built something that you didn't want to build in the first place. So my hope is that, you know, even a hundred years from now, or, you know, if you do not bring the best in people and allow them the space to be creative.

[00:27:33] And if you're, if you're giving them space to be creative, they naturally will disagree with you. And if you, if you can get those two pieces going, you'll probably have the most innovative organization that can be built in that space. Yeah. I think you touched on it, which is we're creating more innovative organizations this way. So could you provide a more concrete example around execution? Like how does this work get done? How do leaders actually start? What's step one?

[00:28:02] What do they need to say or do or how they need to behave or what's the action item in order to start with, you know, getting, getting people to be more creative and thoughtful? Yeah. You, you have to lead by example. And by that is you have to show, you have to appreciate and incentivize the behavior you want to be, you want seeing in your, in your team.

[00:28:27] So, so what, what, what I do typically when I start in an organization and I'll tell you how we started at Orbit Shift is, you know, right now our motion for really building pipeline is very outbound driven, right? We have SDRs calling out, trying to have conversation with C-suite and, and a level below to really start to talk about what our product is.

[00:28:53] And, and you realize the ones that are most successful are not the ones making most calls. So, so, so quantity does not equal quality, right? And the ones who are most successful are doing the very different, unique, creative things you could imagine, right? So, so. Wait, wait, wait, like what? Wait, you have to tell me. Yeah.

[00:29:20] So, so there's so many, so many, so many examples that I can, I can, we can talk about. You know, one of my, one of our SDRs actually wrote to, there are so many times they've written to a CEO and gotten a response. And we typically say, try not doing that because they don't have time. There's so many times we've actually, they've actually called them and said, do you have five minutes? Can I actually, you know, take, take time and discuss?

[00:29:50] There are times they've said, hey, this person is going to that event. Let's go meet him that event. And, and they basically track their time in motion study, if you will. So basically they're spies. They're Sherlock Holmes of the, of the, of the best quality. Right. So, so, but you, you, you as a leader really have to see which ones are, are the ones that are actually making sense. Which ones are really important and creative and most effective.

[00:30:19] And how do you, how do you make sure everybody understands that? I also see the more you try to look over their shoulders, less effect, less effective and less productive they are. And that's true of, of course, any role. So you want to give them the space to say, hey, listen, here's your patch, right? You have a pipeline problem. You need to move, change it. Now, of course you have, you have channels with which you can figure things out.

[00:30:48] You can do outbound, you can do emails, you can have marketing teams figure out a campaign for you. We can go to events. But, but how do you put everything together in today's world to make sure you get the best possible outcome in that way? And if you look at our, you know, top 15, 20 deals that we've done this year, they've all had a funny story. They've not happened in a, in a direct linear path.

[00:31:13] So, so I'd say when you, you encourage that behavior, right? As long as it aligns with your values, right? You're not doing anything that's, that's, that's misaligned with your values. And, and give them space to think about it because I don't think any human works well under pressure, right? The more pressure you put on them, of course, salespeople are always under pressure because of, because of the 90 day, 90 day treadmill they're on.

[00:31:43] But the more you give them the space to think creatively, build pipeline and then help them. So if they're stuck, that's not their problem. That's your problem, right? So how do you spend time one-on-one with them to make sure you understand their territory? You understand how they're reaching out? You understand what they're calling scripters? I've, I actually spend time on the, on our dialer listening to each of my salespeople, how they position so that we train them and say, okay, this is, you might want to think about these options.

[00:32:10] So, so you really have to get to the brass tacks, right? To, to create that culture of creativity and, and descend and, and then talk about, okay, why would you do things differently? And if, if you are doing things differently, you have to be able to justify it. And, and that's kind of my more recent example, but, but ultimately, you know, this can show up in product. You can, this can show up in marketing. This can show up in customer success. It just, it just transcends almost every part of the organization.

[00:32:39] Leading by example is absolutely the first step. I think sometimes it's difficult when you're a leader that hasn't done that in the past and then all of a sudden you have switched. Mm-hmm. Um, so you might even come off a little bit inauthentic, um, because you're like, oh, this person, you know, our, our leadership team is doing something completely different. This is not how they are. You know, um, what are they up to? You know, that, that type of suspicious questioning.

[00:33:07] So if, if a leader wanted to truly ingrain this in the culture for the long term, and I think you touched on it, you know, we talked about values. You know, how do you integrate this value of innovation and creativity and, um, getting that big turnaround, you know, turning around the entire ship, not just for the day. Yeah.

[00:33:31] Yeah, so you, you beta test it first, right? Uh, you start in small pods because ultimately turning out a big ship, especially as it relates to large organization, as you cannot disrupt the entire working of a, of a large company. Yeah. So, so let's say you are, uh, you are, you are building software for enterprises. Let's say you're building HR software just for, just for the, just for as an, as an illustration.

[00:33:59] You want to think about if you are innovating on top of a very, should I say, legacy product, how would you do that? Right. And take that example and really try to separate, completely isolate that team and see how, how would they operate differently? Right. What would an unconstrained thinking look like for that team? And, and once you go through that unconstrained process, now, how do you put some guardrails back into that unconstrained thinking to put it back in kind of the mainstream things?

[00:34:29] Because, you know, if you are, if you're a large company, let's say you are public or, you know, you are employing thousands of people, you know, your heart has to understand that a lot of people's livelihoods depend on this organization. Mm-hmm. And so any, any, any change cannot be drastic. And if it is drastic, you have to be prepared for the consequences, right?

[00:34:55] The perfect one we've seen, of course, is Twitter, which of course went through 80% of the team being laid off. And that's totally fine, right? That's, that's, that's one way of doing things. But if you really want, don't want, you want to create some stability in terms of serving your existing customers and, and making sure your product delivers for millions of users that it currently has, how can you, how can you manage that process?

[00:35:22] So I would say, create small teams, let them innovate in the, in isolation or, or in a, in a small group, bring them back in to see how that can be incorporated back and, and then drive that change through that process of osmosis, right? Can you create four, can you create 10, can you create 15? And then ultimately, if you create that, you know, that tree of, of change, I think that might happen. It's very hard to do that wholesale change. Mm-hmm.

[00:35:50] And the other piece that, of course, I, I never enjoyed when I was a young professional was when, you know, executives come on a call and talk about values and, and culture, it doesn't land, right? I think it's more so now with the current generation, because your values and cultures are how you, how you behave or how you act in real life, right? And in, in front of them. So I'd say you have to embody your culture and values, not, not put slides on it. Right.

[00:36:20] So, so as long as you can actually do that, and again, if you're, if you're an organization of thousands of people, you have to enable the next layer and the next layer after that to, to operate the way you want them to operate so that it transcends. But it's not easy, right?

[00:36:37] So I'd say I might, um, given this massive shift that we're seeing in the world of technology, we get definitely seeing that impacting cultures, impacting people, simply because some are handling it better than others. And, and if you don't have the culture, you probably are not ready for that AI transformation either. Yeah. What are some of the behaviors that you've witnessed or that you've shared with your teams?

[00:37:05] Maybe a technique that you brought from Apple or something that really allows people to say, oh, that, that leader really wants me to think outside the box or do something different. Yeah. So first of all, you got to spend significant amount of time with your team. You have to understand and learn from them before you actually start, start taking action. Good advice. Shocking. I know, right? You'll be shocked at how many leaders don't do that, but yeah.

[00:37:35] Second, when you have your team calls and team reviews, you have to be very mindful of what you are advising, what you're listening, what you're celebrating, what you're not celebrating, right? And celebration does not equal outcome. Celebration equals progress, right? Right. Right. Right.

[00:38:26] And celebration equals right behavior. Yeah. So I have a follow-up review with them. What went wrong. What went right. What didn't go right. What could we have done better? Feedback for them, if I have any, and their feedback for me, right? If, and the whole process of doing that is, can I make them 1%, 2%, 3% better for the next conversation, right? And that's my only goal.

[00:38:48] So every time we have an external call with a partner or prospect or a customer or, you know, or an investor, we always go through that process just to make sure they understand what's important to me. But more importantly, what's important for the company.

[00:39:08] And so if you keep that as almost a non-negotiable early on, and then hopefully you're enabling them to do the same thing with their teams over time, really is what will drive the change that you want to be driven. And so ultimately you have to roll up your sleeves. You have to be in conversations. You have to see how they operate. You have to deliver, give them, you know, your feedback.

[00:39:35] And sometimes, you know, sometimes you have to hold back on feedback as well because you don't know what they said and what they did is going to work or not, right? So you have to be curious with the fact, I mean, it's interesting you said that. I'm not sure if it's going to pan out, but let's see, right? So giving that space to really have some open ideas that may or may not work. But if you don't experiment, you don't find out, right? So those are the things I think are absolutely crucial.

[00:40:05] And again, you know, just embodying the behavior that you want to be seen and then keeping it bidirectional, right? Feedback doesn't flow one way. It has to flow both ways. So if I don't have the courage to hear from them, why should they hear from me, right? So if we can all learn together, I think that's the best place you can be. Yeah. I think you said something really important, which was giving them space to make mistakes and experiment.

[00:40:34] I think that experimentation is really like the core of how people should be operating if they want a more creative organization, more innovative organization. I mean, obviously there's guardrails, but I think what you also said in there was it was a lot about alignment. It was a lot about making sure that they understand and that the North Star is very clear.

[00:41:00] And it's saying as long as we get, you know, in this direction, you know, as long as we get to this star, then, you know, here's everything else is kind of up for grabs. Yeah. Navigate your way through it. Yeah. Yeah. One hundred percent. Because if you're giving them a pedantic recipe to execute, you will not find the most creative people. Right. Then you're finding doers, which is, again, nothing wrong with doers.

[00:41:25] But you would, I think a company can always do with creative people all around and creative people have the tendency to color outside the lines. Yeah. Yeah. So if you give, if you're giving them clear, you know, you give them the space, the bread box, but let them do whatever they want to do within that, within that bread box or sandbox and paint it on canvas. Yeah.

[00:41:47] And I think what we're talking about, what we're leading towards is high stakes decision making, you know, and betting on the things that are different. And what can we make, what can we do to make better bets? I think ultimately what we're trying to accomplish, what would you say the ROI looks like on an organization that encourages dissent? What's the, what's the payoff?

[00:42:17] Is it immediate? Is it long term? How would you measure success? Yeah. Great question. I think it's, it starts with the fact that, you know, you, you miss a hundred percent of the shorts you don't take. Oh my gosh. My husband says that to me all the time. Right. So, so that's, that's kind of point number one.

[00:42:39] Um, so it's almost like the, the, you, you have to maintain the fact that you're running an organization and you want results delivered on a consistent basis, right? You want to see progress, uh, daily, weekly, monthly, quarterly. Yet at the same time, you won't need to have room to figure things out, right?

[00:43:03] Because you, you, everything is not perfectly lined up for you, especially now where almost everything is up for grabs from marketing to sales to, you know, to product. Everything, the way you do things is, is, you know, remarkably different than what it was a couple of years ago. So, so if, if today you cannot create, give room to innovate, right?

[00:43:28] Uh, for your teams, the consequences are they're, they're working in a fashion that is far less productive than it could be, right? Which is, which hurts the organization. The consequences are you probably killed their creative spirit or you've, you haven't hired someone with the creative spirit, right? Because you just, you just get the like-minded people that your organization culture, you know. Right, your talent acquisition process is messed up. Yeah, exactly.

[00:43:55] And then, and you put those two things together, you probably now kind of not in the right trajectory as far as your growth is concerned, right? It may not show up in, in the first quarter or the second quarter, but it eventually will show up as you, as you get to the next product update, as you get to, you know, the next big website refresh, because you've missed a whole bunch of things and, and, and your, and your message doesn't line up as well as you, as you want it to.

[00:44:26] So, so I'd say this is such a constant piece of working together and working well. And, and, and I think once, one thing that you also realize is the cost of rehiring is so high, right? So, so if I, if I hire someone today and I have to let them go and, and that happens all the time, it happens with such a heavy heart.

[00:44:50] One, and two, the fact that, you know, you've kind of now at, you know, square one starting to think. So, so if you can figure things out in terms of really, you're, you're hiring for a curious mind, you're hiring for someone who's, who wants to experiment and figure, figure ways out of doing things.

[00:45:13] You, and, or someone who's actually ready for feedback and is able to share feedback either ways, you probably realize you're hiring for a leader, right? And if you can hire leaders in every position, you are in a very, very good spot. Now, the piece that I need to figure out, at least for myself is, is how do I find that one year experience person in sales or zero years of experience in sales who I know could be as effective as a person who's had 10 years of experience in sales?

[00:45:42] That part, I wish I can crack sometimes. All right. I think we are all thinking the same thing. And I, I don't think we know yet until we need more time to pass, you know, especially with the models coming out after another. And you just don't know what they're capable of until they come out. So you've said too much executive gut feel can be problematic.

[00:46:12] Mm-hmm. Where does intuition take its place from a leader's perspective? Every single day. But you have to be able to explain and walk through your gut feeling at times. And what that means is, okay, I've, I've been in, you know, in the tech world for 25 years, of course, lots of different worlds that I've lived in.

[00:46:38] And as a result, I've built my patent recognition for lack of a better term, right? If I see these kind of behaviors or these kind of activities, I know if it's on above the line or below the line. Right. There are a couple of things happening. One, if I can walk through why my gut feel is right or wrong, I am, I'm kind of pulling out that deep held belief in me as to why I think it's going to be right or wrong.

[00:47:08] So, so of course, there are times when you don't have, you don't have time to think through things. You'll take a gut decision and you move on. But, but too much of a gut decision making means you're not institutionalizing that approach inside your organization. Right. And then everything you are now at the single point of failure for every gut feel check that needs to come through. So, so if I can, if I can manage to take 75% off of my plate or more than 75% off my plate, now the team knows how to make that decision. Right.

[00:47:36] So I've now empowered them to make that decision themselves so that I am not the bottleneck anymore. And this is, this is the number one criteria for where scale fails in, in startups simply because the, the founders and the executive team have not taken them out of the equation. Right. So the more you can do that, more that happens because ultimately my goal, and I, and I always say this to my team.

[00:48:05] I said, my goal is to make sure that all of you are future COOs and CROs and CEOs of a company. And for me to be able to do that, I need you to at least share with me how I think. And the more I can do that, the better it is. But there's sometimes, of course, in the spirit of time and expediency, you just have to make that call. Yeah. And, and of course, you know, you don't have time to debate, discuss.

[00:48:30] Those are all, those are all, you know, should I say par for the course in the, in the way you operate. But, but if it becomes a norm, you need to make sure you, you avoid that. Mm-hmm. I, I think sometimes leaders gravitate towards certain people in the organization, whether they have like a more powerful relationship or, or they're the loudest people in the room. Mm-hmm.

[00:49:00] Mm-hmm. How do we level the playing field so there isn't mediocrity or sway or bias around decision making when people are actually finally speaking up? Yeah.

[00:49:13] And that's, that's so important simply because I, I do think the quietest person in the room needs to be heard because the amount you speak is, has no correlation to the quality of your ideas, your creativity, your, your ability to execute. So, so you have to make sure you are, you are at least giving everybody space to talk and discuss, right?

[00:49:42] First of all, you need to, of course, make sure the person who's talking a lot needs to kind of understand the fact that, you know, they need to give space to other folks to speak. But, but I think that is also more in one-on-one conversations, right? To encourage them to speak, to say, I know you're not comfortable speaking in a larger team. What would be the best way to actually, for you to share your ideas?

[00:50:08] And, and if you can start encouraging them slowly but surely to be able to do that, I think that's, that's a, that's one way of solving that problem. But, but I think creating, getting, creating meritocracy in ideas is, is what needs to be thought through. And again, very much easier said than done.

[00:50:33] How do you take list of ideas from everybody and, and then focus on what could be the best way of executing? Is whether you are higher up in the organization or you're a big talker or you're a squeaky wheel or you're not talker at all. How do you take the, take the human element away and the hierarchical element away and evaluate those ideas is, is, is how I think you should, one should think about it. But I'd say this also is very culture dependent in the organization, right?

[00:51:03] So giving people room, focusing on ideas and not because someone has a seat in their abbreviated title shouldn't be the reason things get swayed. Right. Right. Um, I think it's more important in larger organization than in startups because again, startups are pressed for time. So of course they also need to do that because in no time you become a large organization and you realize, oh, oh damn, I created a culture I didn't want to. Right.

[00:51:32] But, but, but I think, you know, um, if you, if you, if I go through my list of companies that I've worked at, SAP Workday, Apple, um, and then, and then at Triforque, very, very different companies, two European companies, two American companies. Um, and, uh, and I think there is just a natural sense of culture that gets built out through the nucleus of where it exists.

[00:52:00] Uh, all you're trying to do is how can you create your own world that you, you believe will be the best possible for you to drive outcomes. Yeah. Right. So, so you as a leader, of course, have wherever in the organization you are, you are taking cues from what the culture of the organization is, but there's nothing stopping from you from building your own culture. If you think it's, it needs to be different, right? As long as it doesn't go at cross purposes with, with let's say the HR function of the organization.

[00:52:30] But, but you, you have to have your own North Star. Uh, the hope is your North Star aligns with your organization's North Star from a value standpoint and principle standpoint. And if it's, there's a bit of a misalignment, uh, I think you're okay for a little while. Try to see how you can keep yours going as much as possible. And if there's a much of a misalignment, of course you have, you have other options to consider. Yes. And you touched on something that I was thinking about, which was around global teams, right?

[00:52:58] So that brings in an entirely new element to the situation. I think sometimes wherever leadership resides is where most people feel the main culture or behaviors of what the expectation is from a leader. Mm-hmm. How do you, how do you work on bringing in new creative ideas, helping people from other cultures?

[00:53:26] Not just, not just culturally different, but logistically, you know, do they have the time and space to actually speak up as much as people that you might be in the office with? You know, how do you manage all of that? Yeah. And it gets compounded, Felicia, when you are a fully remote organization. Right. No doubt.

[00:53:47] Yeah. So it's, it's really, really hard. And my last two roles, including the current one, we are, we are fully remote, right? We are, and of course, that's, that's just the situation you are dealt with, right? Of course, over time you make, make that change and that transition because I truly believe in the power of in-person, right? I think, I think one, younger people, young professionals need their time and space to actually interact consistently, right?

[00:54:16] And, and I think you learn a lot more by, by just being in person. So, so that's why I travel because I need to go see my team, my customers, my prospects, because I can do, you can do tons of Teams calls or Zoom calls. I don't think it comes even close. So, so that's point number one, right? So, so this problem is, you know, exacerbated by the fact that you are, you are a remote organization.

[00:54:41] And, and then of course, where the center of gravity of the organization is, right? So my last company was, was, it was, it was Europe. And at Orbit Shift, we are, we are India-based, of course, with a lot of presence here in the US. And that balance is, you know, with a lot of people, right? And that balance is, is difference where you are coordinating against, you know, multiple age groups, right? From Gen Z all the way to, you know, boomers, if you will.

[00:55:06] And you're multiple time zones, multiple cultures, multiple roles, it doesn't get easy. And, and the all, all you can, the only way you fix this is, or you try to manage this is make sure you are connecting with them as often and as early as possible, because it is very isolating working remotely. 100%.

[00:55:31] Right? So, so the, the overcompensation has to be done. And the overcompensation has to be done in terms of how often you meet them in person by traveling, how often do you really spend one-on-one time with them to understand what they're going through, you know, what, what their week was like, is, is, is, is productive or not. Now you only have those many hours in the day, right? So, so, as I said, my day started at five in the morning today, just for that purpose.

[00:55:59] And, and, and see how you can best stitch that culture together of knowing people a little better than you would if you were hanging around the water cooler, having coffee with them almost every, you know, every, at least once or twice a week.

[00:56:15] That overcompensation has to be done, but it is super, super hard. So, I'd say you, you just have to lead by example, right? Just to create that, that understanding of culture and values and principles. You have to lead by example, you have to make sure you have to make sure you spend time. There is no, there is no, there is no panacea for it, if you will, right? Especially you have global teams, it gets even harder because, you know, culturally things are different in different parts of the world.

[00:56:45] But, but the hope is that they're, everybody's North Star and everybody's values align regardless of what they, you know, you know, what their background has been. Yeah. What is the cost of not having an organization that's comfortable dissenting? Hmm. Yeah, well, you know, you create a me too culture or, you know, yes, yes, sir, yes, ma'am culture.

[00:57:15] Um, and, and ultimately, you know, you, the ownership of making core decisions sits with very few, right? And, and you expect that you have a large part of the organization just executing on those orders.

[00:57:34] I, I think you have, you have significantly shrunk the, the mental capabilities of an organization that could be working on so many different great creative brains. So I'd say the outcome is, um, you don't create a sense of belonging, the decay, right?

[00:57:54] So the sense of belonging doesn't, doesn't exist because if I'm, I can tell you if I'm, if I'm a individual contributor in an organization where things are handed to me in, in a, you know, in a binder say, go do it. I probably the most, not the most excited person. And that's true of any creative individual. Um, you don't get that sense of purpose and belonging as a result. Um, you, you will go through very high attrition. You will lose your best people.

[00:58:23] And, uh, and I think you will go through a natural decaying process over time. Now you could exist for far longer than you, than one would imagine, right? Because, um, you have a great product and, you know, customers are using it. You could keep existing, but you've lost. What is the opportunity cost of where you are today versus where you could have been as, is the part that, that's very hard to fathom. And I think creating those cultures is, is in my opinion, the most consequential thing.

[00:58:53] Yeah. Um, because you are just relying on your horsepower of intellectual capacity is much smaller compared to what your entire organization could deliver. 100%. Well, Karan, thank you so much for being here. This has been incredibly insightful and your experiences have been amazing to listen to. Thank you. No, I've really, really enjoyed the conversation. Thank you.