Dave: Hey everyone, Dave here with another episode of the Philly Tech Connect podcast. Today I’m speaking with Payal Maheswari, an early member of our PT Community, a certified executive coach with experience working with dozens of leaders across the startup and Tech Community. Prior to coaching, Pile led people and culture at an autonomous vehicle startup in the Bay Area. She served as a key adviser, a coach, and has worked with organizations ranging from as few as 30 people to as many as 75,000. Always focusing on exploring the question of what does it mean to create environments, cultures, and spaces to allow employees to bring their full selves to work and perform at a high level. So, very happy to talk with you, Pile. How are you doing?
Payal: Awesome, yeah, I’m super excited.
Dave: Great. This is, you know, I’ve had people in various domains, but you’re sort of the first kind of culture domain expert that I’ve had. I’ve always been a big culture person myself, trying to foster a high performing and engaged culture both in PT and in my businesses. Let’s start by talking about Executive coaching. Tell me a little bit about what that is, I guess for those who may not be aware, if it at all differs from what we think of as like business coaching or life coaching, and why one should invest in it.
Payal: Yeah, I mean, I think coaching is such an invogue term and it means so much to so many different people. The way that I think about Executive coaching is often as leaders and organizations, we know where we’re going, right? We’re like these are my goals, this is what I want to get, and this is how I want to get there. And that’s sort of this foot that you put on the gas pedal. There’s this invisible foot for most people on the break pad, and that’s the one that’s talking about the self-limiting beliefs or that’s the one that has certain behaviors that keep perpetuating, and you’re like, “Ah, why am I doing this?” or “How?” in moments of stress or whatever it might be. And so a lot of the work I do is saying, “Hey, like the hard part is not knowing where you want to go, the harder part is saying hey, these behaviors that my brain has put into place to keep me safe, how do I lift that foot from the break pad, whatever that might be?” And so, I think, you know, coaching, the way that I think about it, it bleeds into the business realm, the life realm. It’s more of a holistic look of who are you and who do you want to be, and how do we get you there? And so, I coach people across a wide spectrum of problems and thoughts and, you know, I think at the end of the day, the best way to summarize coaching is helping you unlock the best version of yourself.
Dave: Yeah, I like that. So, it’s sort of an easy way to kind of think about it. So, it’s certainly not, at least in your case, not exclusive to people Talent culture, etc. When we talk about coaching, it’s a wider domain of issues that people need help with. But, you know, the fact that it’s executive, is it fair to say, is typically geared towards somebody who is at an executive level in their career or maybe like a business owner or something like that? Is that still the right kind of avatar to be talking about in your case?
Payal: You know, that’s a great question. I think the thing about coaching is it’s hard to scale. It’s me sitting here with you for an hour talking through things. And so often, the price point can be a little bit high. And I think that’s important for like the PT community and in general to learn about this stuff because you’ll find coaches at a wide range of price points and things like that. And so, I say that to say, Executive coaching, I think coaching is super important. I’ve gone to therapy and self-help groups and all of these other ways to become the best leader that I can be in the workplace, and it really wasn’t until I met a coach that just helped me unlock so much more of my leadership potential. And so, you know, anybody who wants to invest in themselves should invest in coaching. Now, there’s many formats to that, there’s many price points, there’s many types of coaches, which is why I think one of the things that I’ve always said to anyone in PT is, if you want one spot coaching session, I will 100% give that to help the Philly Tech ecosystem. And then, sort of talking about the longer-term play, there, you know, I’m stumbling on this question only to say in my actual true belief, every single person deserves a coach in a similar way where like most people have a therapist because it’s someone in your corner helping you get to the best version of yourself. And so, I will always say, an investment in yourself, no matter what level of leadership that you’re at, is important.
Dave: I don’t think you’re stumbling at all, by the way. If anything, I think stumbling is a sign of someone actually really trying to think through a question and give a genuine answer. Like to see stumbling, you know? The thing about coaching from my perspective, you mentioned, you know, more or less it’s usually at a higher price point that maybe the average kind of person starting out may not be able to afford themselves yet. Additionally, many of us don’t have a lot of experience with coaching in general. It’s not like, you know, everyone has a bank account different things that you’ve kind of, you have expectations and you have ways to compare and contrast. So, when you start working with a new coach, you may be kind of struggling like, how do I know this is the right fit? Like, how do I know this is going to be the person for me? And what should I kind of expect, and if it’s, or, you know, does it need more time? Like, how should one go evaluate a coach and understand whether or not is the right person for them and what are the right expectations kind of going into it?
Payal: That is a phenomenal question. And what I might not have the best answer for, but my personal philosophy is this. I always give people the time they need to decide whether or not I am the right coach for them. And it comes in the conversation, right? So, if you’re finding a coach that says, “Hey, I need you to sign on the dotted line and before I even coach you,” I wouldn’t go that way. I would say, “Hey, listen, I need to make sure there’s a chemistry here between me and you. Can that person communicate with you in a way that, leaving the call or leaving the coaching session, you’re thinking about new ways of operating or you’re thinking about, ‘Wow, hey, this is a fundamental shift I want to make in my life,’ or the way that I think about things? Every session isn’t going to have that, right? Every single week you’re not going to have like seismic changes in your life. But I think it’s walking away from a conversation saying, ‘That was an hour well spent on my own personal development.’ And then, over the course, the week or the two weeks between your coaching sessions, you’re starting to want to do things differently.”
Dave: That’s a good way to, I guess, determine, you know, what’s the right fit. And I don’t want to speak about, you know, everyone has their own sales process and the way they kind of go about it, to each their own. But sometimes, you do get on a call with someone and it’s much like, “Hey, we’re going to chat for a little bit and then just try to get you hooked on some sort of contract or long-term commitment or something like that.” And I always feel that, you know, the coaches also should want to make sure that there’s a fit both ways, you know? And that’s why I feel, as you mentioned, that kind of having a couple of conversations or whatever it is, is a good way for both parties to feel like they have determined that this is going to work for them. And the last little thing I’ll say is that sometimes, I don’t know if this is the case in yours, but certain coaches maybe have content that they put out in general like a podcast or maybe a course or something like that. Those can sometimes be like a way to get a feel for the person, their style, maybe a lower-priced entry into kind of learning about them before kind of committing to something more substantial.
Let’s talk about the people culture talent side of you as well. So, because I know, yes, you do Executive coaching, but you also have helped us out, and by us, I mean Shortlist, which is my marketing agency, with some HR issues that we’ve had, and have been helpful to other people as well. You know, culture is such an interesting concept because there’s not, you know, it’s hard to kind of put a metric around it. So sometimes, people don’t really know what it means. How do you kind of think about the people culture talent issue at small organizations? And when is it the right time to be thinking about it? You know, things like that. It’s a general question.
Payal: Yeah, no, and I have so many different threads I want to change B on that, but I think the question you ended with, which when is the right time to start thinking about people and culture within your organization, it’s immediately right? Because any organization that is going to bring on their first employee or going to bring on a co-founder, those are critical decisions of how do you want to operate in this world, in this world that, regardless if you’re a tech entrepreneur, the world is human, right? And the people you’re interacting with and building something with are going to be the makers or breakers of success for your organization. And so, you know, I think one of the things I always ask really early-stage Founders is, as you grow in scale, what’s gonna what do you really need and what really matters to you? Because it’s easy to throw out there like, “Oh, I care about employee experience and I care about high performance and I care about everybody getting rest and being rejuvenated,” you know? There’s a whole slew of things to care about. And so, the way that I would define culture in an organization is how do the people that work here interact with one another? How do they treat each other? How do we communicate as an organization? How do we make decisions? And how do we ensure that when we have tradeoffs, we’re being really clear about why and how we’re making those tradeoffs?
Dave: You know, you mentioned that you’ve worked with organizations from 30 people to 75,000, and I feel like, you know, please correct me if I’m wrong, but there is a lot of association of culture and like the size of the company, right? Like those two things often are kind of like related that companies have a certain size tend to kind of maybe air towards these type of cultural aspects whereas a smaller company maybe things are a little more agile, etc. I don’t know, but it sounds like if culture is done right, like it should be independent of the number of people at the organization. Like it should be something more rock hard that kind of goes with the organization as it grows. I mean, is that am I thinking correct like and how have you seen culture evolve or break down as companies get bigger?
Payal: I mean, I think 100% what you just said. It doesn’t matter the size of the organization. You’re working with one other person, there’s a culture there, right? There’s an operating model that you’re working in, a construct you’re working within, and scaling that when it works is really, really important. And when it’s not working, having the really hard conversations around why isn’t this working and what do we want here so that when you do scale, you don’t have factions within an organization, right? And that’s a lot of why that co-founder relationship is super important. If you have a co-founder, which is, if two people are not on the same page and then you start to grow or hire, it doesn’t matter if you’re five people or 500 people, the organization, the employees that work for you, you are going to see that disconnect and are going to be confused by it. Right? I don’t know if that, does that answer your question? Like, culture is independent of how many people you have working.
Dave: No, I think that’s the way to be thinking about it. But so often, I think there’s certain stereotypes of businesses of various sizes and what the culture maybe is or isn’t or should be. Let’s say you have a bad culture, you know, how do we go about fixing that? You know, how often is the answer like certain people got to go? Or is it, you know, what are the other ways in which companies can kind of correct, you know, bad culture? Like, how do we do it?
Payal: I think the first question is like, how did we get to this culture? Right? Figuring out the root cause of what happened to get us there because I don’t think people inherently like leaders or Founders go into organizations being like, “Yeah, I’m going to build a bad culture,” like that sort of doesn’t happen. And so is it a byproduct like what what is a bad culture a byproduct of? Is it a byproduct of lack of prioritization, lack of good decision making, lack of transparency? Like, where is it that things are breaking down or is it, you know, not as much rigor in the hiring process? And so, the first thing that I do in organizations or in situations like that as an external party is get to the bottom of that answer which means talking to people, really understanding like what are the things they’re not saying out loud? If you’re at an organization and you’re trying to figure this out for yourself as a leader, I would ask those questions to say, “Hey, I’m and with vulnerability, if like, I’m noticing that there are some behaviors that our organization has adopted over time that actually aren’t the intention of the way that I want people to work here, and I’m trying to get to the bottom of that in a very genuine way.” And you have to mean it, right? You can’t just go out and do a campaign and not mean it and ask people that same question of, “Well, tell me what’s working, tell me what’s not, and then tell me, you know, as I think about scaling or as I think about course correcting, what are the must-haves, what are the things that we absolutely cannot drop the ball on?” People will tell you, and it’s a matter of can you actually listen and interpret that in a neutral way because very often, well, I won’t say very often, I will say 100% of the time, culture is set at the top. And so, I’m always apprehensive in organizations where they’re like, “Oh yeah, the people and culture team handles that,” or that the HR team handles that because that’s not true, right? Culture is more than the coffee machine that you have or the employee perks or the wellness days or the whatever else it is, like, that whole Disneyland concept. That’s not people and culture. And I think I’ve said the same words over and over, but those words really matter, right? Priorities, decision-making, transparency. That is culture.
Dave: Yeah, it’s interesting because, you know, when I think about culture, as the sort of the leader in my organization, I like to think we have a good culture. You know, it obviously makes me feel good about myself and what I do. And I think in general, we really do. But there is so much more to culture that isn’t like the obvious kind of like, well, people aren’t mean to each other, they’re not like condescending, like there’s, you know, one thing I’ve noticed, for example, that Shortlist is, you know, people in general are on the quieter side, they’re more quieter about maybe voicing opinions or jumping into a conversation or things like that. And I think for a while, you know, I kind of thought it was cultural, like almost more like geographical or nationality because our team tends to be largely in Macedonia. And, you know, it’s like, you know, maybe that as part of their culture, they’re just not used to speaking up in different things. But now, I’m starting to think, well, but maybe there’s things within the organization we can do to start to try to encourage more dialogue and get people speaking up. So it’s not to say that there a bad culture but that there are aspects of the culture that I would like to kind of improve, so this is very much on my mind in 2024, which is why I was happy to have this conversation.
Payal: No, and you wrote about it. I saw that you wrote about this specific thing on LinkedIn, and one of your takeaways was like you have to open to feedback. So, don’t ask a question if you don’t want the answer.
Dave: True, yeah, very true. Um, criticism is hard to deal with, right? But we all need to live with that. So, um, this was awesome just to chat a little bit about Executive coaching, culture, um, for people that want to learn more about yourself, um, your services, get in touch, where should they go?
Payal: Yeah, I mean, for the folks that are in the Philly Tech Entrepreneur group, I’m active on the Slack channel. So, shoot me a note. I have a pretty open calendar policy. And so, I’ll send you, you know, a calendar link. We can always get on the phone. Um, of course, I’m on LinkedIn and other things like that. Um, I think what I would say as folks here either think about something like coaching for them specifically or for people within their organization or just thinking about people and culture as a concept, um, it’s never too early to invest in yourself and into your organization because when you set a really clear Foundation of what you care about and how you want to act and operate, it will pay dividends forever. And having done this for many, many years, one of the things that people I see in the entrepreneurial community is like, “Oh yeah, yeah, we’ll deal with it when it’s a problem.” And when you do that, you’ve one lost a lot of goodwill along the way, um, and you’ve lost a lot of opportunity to really unlock potential and performance because people aren’t feeling connected to the mission and the company. Um, and so, yeah, don’t think of this as a future you problem. Like, even a conversation with me or anyone else in your network about people culture, coaching, they’re important things to think about as a holistic leader.
Dave: Yeah, um, you know, don’t be reactive, right? Be proactive. Um, as is great because we’re, you know, relatively early in the year. Even when this episode comes out, it will be kind of like, you know, earlyish in the year. So, it’s a good time for people who are thinking about investing themselves, investing in their organization. Maybe now is time for a coach, um, or someone to evaluate, you know, the organization, things like that. So, if you’re out there, you’re listening to this and that makes sense to you, get in touch with Pile and our Slack Channel. Um, and thank you so much for, uh, chatting with us today.
Pile: Yeah, thank you so much. This is awesome.