
Daniel Robbins sits down with Deepali Vyas to unpack why “performance problems” are often fit problems, and why the most dangerous leader is the “almost right” one. Deepali breaks down talent market fit as the alignment between a person’s wiring and a company’s stage, pressure, and reality, not the résumé or big brand logo. They also go deep on the future of work, from portfolio careers and fractional leadership to why most companies are skipping the ROI layer of AI adoption and will likely overhire after they overcut.
Loading summary
Commercial Announcer 1
There's nothing like your first Mac. Here's what people online are sharing, rhain says. Everything is just so smooth and fast. I still can't get over it. Syncing stuff between my phone and this is just chef's kiss. Rincredible488 says Apple Silicon basically cures low battery trauma. That's how they felt with their first Mac. How will you introducing the all new MacBook Neo, an amazing Mac at a surprising price. Find out more on apple.com Mac hiring isn't just filling a role. It's about finding people who can drive results Indeed Sponsored Jobs helps you match with the right candidates faster. Target candidates by skills, certifications or location. Join the 3.3 million employers worldwide that use Indeed to connect with quality talent that fits their needs. And listeners of this show will get a $75 sponsored job credit to help get your job the premium status it deserves@ Indeed.com podcast. Terms and conditions apply. Hiring do it the right way with Indeed
Commercial Announcer 2
Pros Just because something on the job runs out doesn't mean you have to order it on the Lowes app Myloes Pro Rewards members get free same day delivery on eligible orders over $25. Get the fasteners, hardware or tools you need to keep the job Moving. Order by 2pm and get eligible in stock items delivered right to your job site by 8pm members get more at Lowe's Loyalty programs subject to terms and conditions Subject to availability restrictions and terms@lowe's.com shipping terms subject to change.
Dan (Host)
So depali when I was in my corporate environment what I noticed was people were getting fired and many times it was because they were not the right fit for the position. But the corporation is like put them on a performance improvement plan, the, the, the amazing pipe. Put them on that and then basically get them out like whatever. Hire slow fire fast, right? That was like, you know, do these things and I what I always found is as a leader as I continued to move up, that people were just not in the right position and they're forced to doing a job that did not fit for them. How do you see this?
Depali Vias (Guest Expert)
First of all, I think this happens more often than you think and that seems to be the age old problem around organizational design, right? When you see people on pips, it's not because they were incapable, it's because they were misaligned, right? It was the wrong role, wrong stage, wrong manager, wrong pressure profile. But I think the uncomfortable truth is that, you know, it's sometimes it's not fire fast. It's diagnosed correctly. So I think the corporate mistake here is corporations assume if someone isn't performing in this role, they're under performing as a person person. And that's flawed thinking, right? Performance is contextual. And so if a person has high potential but they're in the wrong function, that's a problem. If they're strategic in an execution heavy role, also a problem. If they're executional in a strategic role, also a problem. So they're never going to win. So I think the leadership question here is why are they failing and where would this person win? And that's fundamentally different leadership posture. And I think that there's a diagnostic for this right before you pip someone, figure out what is their capability? Like do they actually have a skill set that's required, not, not from before, but like what are they really, really good at? And then where's the energy fit? Where, where does this work drain them versus what energizes them? If someone would have asked me that early on in my career, Dan, it would have been super obvious where I thrive versus where I am. I suck at details, period. Full stop. I suck at it. But I am really good at empowering people, setting big vision, energizing people towards a really big goal. And if they would have seen that earlier on, they wouldn't have put me in, you know, spreadsheet land, right? Because that's not where I thrive. And then the last part is, you know, the. Well I talked about autonomy fit, but like the stage fit, right? Like is the company in a phase that matches it matches their wiring, right? Because sometimes you can be in a high growth company and you're the kind of person that's like, look, I want to be really pragmatic and methodical and whatever. You don't fit there because they want to move fast and break things, right? And so that's where all of these things kind of go wrong and the wires get super crossed.
Dan (Host)
Which leads me to this thought around most founders are obsessing over product market fit. You argue about talent market fit. How do you recognize this before you even put someone in a position? So if you're going to interview someone and you're going to match them to a position, and then what do you do the moment they're in there, if you're realizing it might not be that fit?
Depali Vias (Guest Expert)
So founders do obsess with product market fit, which is fair, right? But, but most of them don't think about the talent market fit. And that's why a lot of these great hires fail so what is talent market fit? Right? It's not the impressive resume, the big brand logo, the years of experience, the raw intelligence. It's really the alignment between a person's wiring and the company's current stage and the pressure and the market reality. That's talent market fit to be really, really clear, right? So here's where founders I feel go wrong. They will hire the quote, unquote best candidate, the most experienced operator, the person who crushed it at a bigger company. But they forget that the environment changed the outcome, right? So I always say this a lot. You can come from a really big branded logo. You really have to ask yourself as, as a founder, hiring that person, does did that person, you know, make the logo or did the logo make the person? Right. That's a really big difference. Because could they stand up on their own without the logo? And does that matter for you now? Right, so like a VP who thrived in a 3,000 person infrastructure, they had a deep bench, they had clear process, they had brand gravity. Those people will typically fail in a 40 person chaos, right? Ambiguous strategy, founder led decision making, capital constraints. Like that VP is smart, they're different. There's different results that they have in that organization, not in this organization.
Dan (Host)
So we had a guest on before Frances Fry, a Harvard professor and she helped the transformation through Uber when it was the founder to the, to the new CEO. And, and I was fascinated to hear about this whole like founder, CEO, when the company scales, you now need a new CEO because of the fits of the company. What do you see around C suite fit as the company scales over time.
Depali Vias (Guest Expert)
So I have a confession. My team and I, my team actually worked on the Uber CEO search. So life has come full circle. To talk about was really difficult and where Uber was at the time because it was founder led. If you think about where they were going at the inflection point that they were and you know, Francis probably can, can know, go more deeply into this. They needed institutional gravity, they needed institutional process. And Dara was one of the few people that had built several companies to a stage that had these institutional processes that could really build world class frameworks and process and get everybody organized to row in, in a, in, in one direction. Right? And, and he had done that over and over again. He also had a bit of gray hair and he also had the maturity and he also had the longer term vision because he had been a visionary previously. Right. Not to take anything away from, from Travis, but I would say that there is an inflection point that happens and by the way, like, not even just Uber, you know, you. I'm sure you've watched shows like Silicon Valley, right? And so when those things do ring true in real life, right, the CEO profile has to evolve based on the stage that the company is at, right? And so I just gave you the sort of microcosm version of a VP that thrives in these types of environments, won't really thrive in that. The reverse is also true, right? If you have just played sort of quote unquote, small ball, and you really need to go to this level, what does all of that infrastructure need in order to get to that level? And you need the right CEO profile. So that's what we're really talking about.
Dan (Host)
It's fascinating. I mean, it's very fascinating around what happens with your company as you continue to grow. And also, like, where. Where would I want my company to even go and what do I need to sacrifice? As a founder, I know many that were kicked out of their company or the board or whoever, investors remove them and put somebody else in. It's very interesting around what happens with the people as a company grows. But let's say there's a organization, maybe less than 20 people, they're not thinking about people so much because they're still thinking about growing and scaling the organization. Is there a simple audit or something that they can do to look at their organization to see if the people they do have are correct?
Depali Vias (Guest Expert)
The audit, I would say, like, if you think about it from like a board level, because that's typically why these things, you know, come about. What stage are we actually in, right? Like not what stage we're aspiring to be, but what stage are we actually in? What problems dominate this stage? Is it innovation, scale, governance, turnaround? What is it? Right? And then do the leaders in our organization, right, Whether it's, you know, at this small stage, but they're all basically leaders, right? Does that pattern history match that pressure? Right? So does past patterns predict future behavior and can they handle it? That's the diagnostic. And the hard truth is like, you know, sometimes the most dangerous CEO is not a weak one. It's the almost right one, right? And so that's where, you know, boards and the leadership teams really have to take audit or take stock of where they are. By the way, like you mentioned something earlier, I'm literally working with a founder right now that got pushed out by a board, even though they had had multiple exits, you know, had had 300 million in revenue in their previous companies. But she got replaced by and A man. And there was a whole dynamic there as well. And there was a reason for that because when they were raising the next level of capital, they needed the face that was going to represent what that next face, what that next phase was going to be. So there's a lot of dynamics that get played out in the boardroom.
Dan (Host)
We just had another guest on who is talking about this issue around. Many times women founders seem to be removed from their company without them. And, and I've, I've talked to some really well known companies before. Not on the show, just privately. Who, if I said their names, people would know them like household names. They were all removed from their companies. It's great. There's a whole group of women that meet up, I guess, who have all been removed to talk about like what you can do in the future and why do you think this is happening and is it related to what you were just saying around the, the future of the company? Is it only. Is it because there's not a lot of women who are founding, you know, larger companies? What do you think it is?
Depali Vias (Guest Expert)
So I think that there's a, it's, it's. First of all, I don't think it's random, right. High profile founder removals have happened to men and women, but the pattern feels different for women. And there's actually sort of structural reasons that I believe. Right. One is the capital dynamic. Venture capital is still overwhelmingly male. That's a fact. Boards are still overwhelmingly male. Also a fact. And power networks are still relationship based. So the tension kind of arises where, you know, there's founder vision board pressure and growth expectations and the person with less embedded power losses. That's where the conversation takes place. And women founders statistically raise less capital, have fewer deeply embedded board allies and they get scrutinized earlier for leadership maturity. And that compounds under stress.
Dan (Host)
My mind, I'm blown. My mind is blown. Like I never. The power dynamic, I never, I've never even heard of this, to be honest. Like the power dynamics of what's going. This is why I never. Liberty Mutual customizes your car and home insurance. And now we're customizing this rush hour ad to keep you calm, which could help your driving. And science says therapy is great for a healthy mindset. So enjoy this 14 second session on us. I think you've done everything right and absolutely nothing wrong. In fact, anything that hasn't gone your way could probably be blamed on your father not being emotionally available because his father wasn't emotionally available and so on. And now that you're calm and healing. You're probably driving better too.
Commercial Announcer 1
Liberty Liberty Liberty Liberty Hiring isn't just filling a role. It's about finding people who can drive Results Indeed Sponsored Jobs helps you match with the right candidates faster. Target candidates by skills, certifications or location. Join the 3.3 million employers worldwide that use Indeed to connect with quality talent that fits their needs. And listeners of this show will get a $75 sponsored job credit to help get your job the premium status it deserves@ Indeed.com podcast. Terms and conditions apply. Hiring do it the right way with Indeed.
Commercial Announcer 2
Just because something on the job runs out doesn't mean you have to order it on the Lowe's app. MyLoes Pro Rewards members get free same day delivery on eligible orders over $25. Get the fasteners, hardware or tools you need to keep the job Moving. Order by 2pm and get eligible in stock items delivered right to your job site by 8pm members get more at Lowe's loyalty program subject to terms and conditions Subject to availability restrictions and terms@lowe's.com shippingterms subject to change the Jack Welch
Commercial Announcer 3
Management Institute at Strayer University helps you go from I know the way to I've arrived with our top 10 ranked online MBA. Gain skills you can learn today and apply tomorrow. Get ready to go from make it happen to made it happen and keep striving. Visit strayer.edu Jack WelchMBA to learn more. Strayer University is certified to operate in Virginia by Chevin as many campuses including at 2121 15th Street north in Arlington,
Dan (Host)
Virginia is money because I was too afraid of of the power, giving up the power.
Depali Vias (Guest Expert)
And I'm a three time founder and I have raised money and it is a slog in the mud. And I do realize I'm a female founder right by the way in my seat raising money and I raised over a million dollars for my last for my last venture. Even just that. By the way the zero to million is the hardest. I would say I was scrutinized like a series a company versus a seed company as a female founder. That's firsthand experience.
Dan (Host)
Hope it changes because I know the the amount of money going to women is very small. We just had the previous founder of Task Rabbit who who started her own VC firm now to hopefully you know, try and solve this but obviously it's it's something huge when you look at the the future of of what the workplace will be. A couple years ago this was like the topic everywhere. Will people go back to the office hybrid Then all of a sudden it became a topic again and there was a, you know, a company recently just laid off 4,000 people and said it was because of AI. I'm sure it wasn't because of just AI. But this is really becoming a thing, right? Like a lot of jobs are being lost to AI and I, I have a family member who has always never had a problem getting a job. It just took her like two years to get a job and she's like in a very specific niche job that normally she never has a time without a job. So how do you see the future of how this is going to play out? With obviously AI and robotics just advancing so fast.
Depali Vias (Guest Expert)
So I live in the world of data and AI from a search, executive search perspective. So you know, a lot of times even I get a lot of pushback saying, you know, you're the reason why all of this stuff is happening. You're putting these AI officers in these seats and all of the stuff. I think first of all, I know the company that you're talking about. When companies say that they laid off 4,000 people because of AI, it's almost never purely AI. But let me tell you what's happening in this market because I did a video about this recently and kind of connecting the dots here, there's a few things. At the leadership level, AI is being discussed ad nauseam. I also think a lot of people don't understand AI in depth. There's a lot of low hanging fruit which, you know, most CEOs and boards want to take advantage of but they don't know how. So I call this sort of level one, level two, Level three thinking. Level one is have your employees experiment with, with this stuff. Whether it's chat, whether it's, you know, Gemini, whether it's Claude, whatever it is, when you're doing it individually, you are now maybe 20, 30% more productive because you're using these things with, with that amount of utility. Level two is when you think about the workflows in your organization of hey, my team has to deliver this. So there's a lot of different people in a lot of different places in these workflows that really need to connect the dots via AI enablement. To actually get that thing in a place where it is saves 30, 40% more time or cost savings or whatever it is. That is the layer that really needs to be built out in corporate America, right? And the third layer is the whole system redesign. What companies are making a mistake right now is there's level one and then there's level three. But the missing middle is where the ROI is really at. And that's why there's frustration and that's why you're seeing this overcutting, right? You're, you're seeing all these layoffs saying, well we're every EA is going to solve everything, but they haven't done layer two, so they think they're just going to redesign stuff. And I guarantee you the people that overcut now will over hire again in the next sort of pendulum swing. So I think that there's a bit of a, somewhat of a misinformation and myths out there. And then, you know, MIT came out with a study saying, you know, 95% of companies are not getting the ROI on AI. But when you dig in a layer deeper, it's because there's 12 power users of Microsoft Copilot and nobody else in that organization because they haven't really been taught how to do all of these things right. So that's the reality and that's why I did that video on like, these things will only move as fast as, as budgets can approve, right? Or you know, road maps can be approved and that's going to be a longer cycle. Now Block did this, you know, layoff and I think that it's, it wasn't purely about it, but they're taking advantage of the time where, you know, they, there's sort of cheap capital that's disappearing, there's margin pressure, whatever it is, but they want to signal that they are AI accelerating.
Dan (Host)
I thought of a funny show. We, we as humans give all of everything, all our jobs to AI and robots. Then the robots become human, they unionize, then they want days off, they only want to work 20 hours a week. And then humans have to take back over. I think, I think that might be what's going to happen when you. Which leads me into. I'm seeing a lot of younger people, let's say in their 20s, taking on jobs at like Claude, for example, who just gave out like billions or hundreds of millions of dollars in stock options to their employees. Private options. You could work out like SpaceX and get private options and then it goes public. I wonder how in the next two or three years they will become multi, multimillionaires. Some of these companies I'm seeing like if you're getting stock like this and it goes public or even it already is public, or they're getting paid $500,000 to work at Meta, I wonder if they're only going to work for a few years and then stop working.
Depali Vias (Guest Expert)
So that's a great point. And a lot of the stuff that I talk about, you know, on my sort of elite recruiter platform when I'm out there, is the rise of the portfolio career. I think the traditional career, staying at one company for a very long time is over. And I think the future of work is going to be everyone is sort of stacking skills, skills within these organizations, getting a lot of, you know, compensation for it. But I think that they are going to learn and do all of these things and then say, hey, if I can do it here, I can do it across the board. And so they will stand up multiple income streams based on their expertise, and that's what a portfolio career looks like, where they will eventually become independent consultants. But now the rise of independent consultants and being able to advise or do Sprint work or do advisory work or do advice, you know, fractional work with multiple companies, because those companies need that expertise from these very few people. I think you're going to see a rise in the ultimate portfolio career. So it's sort of like single consulting houses, solopreneurs, or they will get their friends together and build this whole consulting collective that goes against all of the big professional services companies that we see today and break those models in half.
Dan (Host)
The big firms need to watch out. It makes sense. I'm also wondering, like, because we've been talking with other guests around the wealth transfer. I keep thinking about this. There's like $80 trillion in wealth in the US that's transferring from baby boomers to Gen Z and Millennial in the next few years, as they age out, they're getting these jobs that could be making a. Potentially a lot of money if they can take a few hundred thousand dollars home in dividends. I don't know if they want to work because I, you know, like, they. It seems like they're. They want to work for. They want to be passionate workers, they want to travel, they want to dance on TikTok, or they want to be content creators. I don't know if they want to hustle and grind. Like, I'd say like older millennials and up we were, you know, you and I, like, we got to hustle, we got to grind. But If I'm making $200,000 a year and just from dividends or 250, I'm not sure if I'm one of them, if I'm going to work anymore, which I wonder what happens to that. That base of probably highly educated, skilled workers. They are just gone. What do you Think, first of all,
Depali Vias (Guest Expert)
you are kind to lump me into older millennial, because I'm definitely not that. I am much older. I appreciate that. You know, Dan, that's such an honest question. And it's layered, right? Because what you're really asking is, if people don't have to work, will they still choose to work? And that happens to a talent and. And what happens to that sort of talent base? Like you said, highly educated. So let's kind of break this down. I think the dividend illusion, right? First, the number of people truly living off of 200,000 passive income is still relatively small. And I know that those numbers are, like, really highlighted. It's still relatively small when you, when you think about, like, the distribution of it. So here's what social media sort of amplifies. They amplify, the crypto wins, the exit liquidity, the creator revenue spikes, the dividend screenshots, all that. But statistically, I think most people do not have permanent sustainable passive income at that level. Right? There's a loud minority effect that's happening there. Let's be really real. And I think that work motivation is shifting. It's not disappearing. So, like older millennials and Gen X, right? We work from the point of view of, like, we need to survive, we need security, we need status, right? The younger cohorts work is sort of optional identity expression, right? It's economic context. So if you grew up during 08 and you were watching layoffs and you see loyalty unrewarded, you're going to equate optionality with safety. Meaning I'm not going to work for that one employer that can lay me off one day or go under. Right? And I think if someone truly has $200,000 in passive income, here's the interesting part. I think those people will build that passive income. They do have ambition, they understand leverage, they enjoy building. They. They like status, they like influence, right? None of that stuff is going to disappear. They're going to pivot and they're going to become angel investors, they're going to become fractional advisors, they're going to become creators, they're going to become portfolio operators, they're going to become board members, consultants, whatever. They may not grind 80 hours, but they're not going to vanish from productivity. And I think this is where I feel, look at me, right? I don't need to work if I don't really want to. I'm doing it out of the sheer sort of passion that I have for it. So I think even this younger audience, this younger Sort of cohort that's coming up. They're going to want to do meaningful work and that might not yield like the comp that we might be used to, but they're okay with that because they have this passive, you know, income back there and that's where it's going to, that's where it's going to win. The new, the new equation I'm going to say is income is really leverage plus skill plus distribution. I think that's the equation.
Dan (Host)
I've never, I think I've talked to over 1400 people in six years. I've never heard this before. So I, I like to have a guest on who's telling me something I've never heard before. And really my mind is suddenly expanded. Like that is very interesting. I, I could see this whole, like, it's like the rise of the gig economy, like the fractional type. Like I don't want to work full time for one job, which I don't blame anyone. I remember the last job that I had and I was miserable and they would never really allow me even though I kept, they kept promoting me. But every time they promoted me I was even more miserable than the previous time. And it was like the, the only option I had, like I wanted to move somewhere so I had to get into a different, like I would rather like, okay, I work here for a few months, I work there for a few months, I do this, I work five different places for like three hours a week.
Depali Vias (Guest Expert)
But Dan, that's a structural thing, right? Because corporations are not allowing that type of flow.
Dan (Host)
Exactly.
Depali Vias (Guest Expert)
If they were to allow that type of flow in and out and not be burdened by, you know, if, again, if you, let's zoom out 30,000ft for that to happen, for your lifestyle that you just described to happen, you need to make sure that, you know, you have some benefits in the background. You have, you know, something that you have sort of a savings account, et cetera, et cetera, but you have freedom to move through the system. And until we get there, that's a structural problem. However, I think we as the employee base or the solopreneur base or whatever it is when we start disrupting the system this way, that like, hey, we're not going to do this, we're going to do this on a 1099, we're going to do it on a three month contract and we're going to be in and out and you know, I will find a way, a marketplace that's going to have all my benefits and help me with My quote unquote 401k or an equivalent thereof. I feel very good about being in and out. Most people feel stuck because they don't have the understanding of what optionality looks like.
Dan (Host)
I feel like people and corporations need your help.
Depali Vias (Guest Expert)
Yeah, but that's right.
Dan (Host)
It seems like to me. So if they want to get in touch with you because they all need to, how can they do so so
Depali Vias (Guest Expert)
they can reach me. I have my website depolivias.com I'm on Instagram and TikTok and LinkedIn and all of things. But hello@depauz.com they can reach me there.
Dan (Host)
And then your book will come out. Eventually we'll have to read that. The fact that you're you're wearing Vias media sweater. Like I need to get a sweater. This has been great. I I appreciate it. I I've learned a lot. I learned a lot. Thank you. I learned a lot today and a lot of sound bites. So I can't wait to share this with everyone. So thank you for joining us.
Depali Vias (Guest Expert)
Appreciate it.
Dan (Host)
Spring starts at the Home Depot and we are bringing the heat to your backyard this season. Fire up the flavor with our wide variety of grills for under $300 like the next grill 4 burner gas grill that's perfect for hosting your spring cookout. Then set the scene and turn your outdoor space into the go to spot the patio sets for every budget. Bring it this season with grills that deliver flavor and patios that set the vibe from the Home Depot. Start your spring with low prices guaranteed at the Home Depot exclusion supply. See homedepot.com Pricematch for details.
Commercial Announcer 1
Hiring isn't just filling a role. It's about finding people who can drive results. Indeed Sponsor Jobs helps you match with the candidates faster. Target candidates by skills, certifications or location. Join the 3.3 million employers worldwide that use Indeed to connect with quality talent that fits their needs. And listeners of this show will get a $75 sponsored job credit to help get your job the premium status it deserves@ Indeed.com podcast terms and conditions apply. Hiring do it the Right Way with Indeed Bob Evans.
Commercial Announcer 2
Creamy Mac and cheese and buttery mashed potatoes are made for the moments you can't plan, like last minute school costumes, glitter explosions or when little Liam brings three friends for dinner. No plan, no problem. Say hello to Plan B O B from Bob Evans because when you bring out the Bob, you can take comfort in knowing you'll always have something delicious on the table no matter what the day brings. When you need comfort, bring out the Bob. Available now in your refrigerated section.
Commercial Announcer 3
You do it all, so why not get all the electrolytes hydrate better than water with new Gatorade Lower sugar Now with no artificial flavors, sweeteners or colors and 75% less sugar than regular Gatorade. New to the fridge. All the Gatorade electrolytes you love. Gatorade lowers sugar. Is it in you? Now available nationwide. At Strayer University, we help students like you go from Is it possible? To anything is possible by offering access to up to 10 no cost gen Ed courses so you can reach your goals affordably and fast. Visit strayer. Edu to learn more. No cost gen EDS provided by Strayer University Affiliate Sophia. Eligibility rules apply. Connect with us for details. Strayer University is certified to operate in Virginia by Chef and has many campuses, including at 2121 15th Street north in Arlington, Virginia.
Why Great Hires Fail and How to Fix Talent Market Fit
Host: Dan (IBH Media)
Guest: Deepali Vyas, Founder & CEO, Vyas Media & 'The Elite Recruiter'
Release Date: March 24, 2026
In this episode, host Dan sits down with Deepali Vyas—serial founder, elite recruiter, and CEO of Vyas Media—to dissect the not-so-obvious reasons behind great hires failing and the crucial, often overlooked concept of “talent market fit.” Through candid stories, hard truths, and actionable diagnostics, they explore how organizations can fundamentally rethink recruiting, retention, and leadership at every stage, from scrappy startups to scaled behemoths. The conversation also traverses boardroom power dynamics, gendered founder exits, the rapid rise of AI, and how the very concept of a career is being rewritten by the next generation of talent.
Misalignment, Not Incompetence
(01:35) Deepali shares that poor performance often signals a misalignment between a person's skills, the role, the organization's stage, the pressure profile, and even management style—not a flaw in the individual.
“When you see people on PIPs, it's not because they were incapable, it's because they were misaligned. ... Performance is contextual.”
— Deepali Vyas (02:14)
Diagnose, Don’t Default to Firing
She criticizes the "hire slow, fire fast" dogma, arguing leaders should first deeply diagnose the root of underperformance:
"I'm really good at empowering people, setting big vision, energizing people... If they would have seen that earlier on, they wouldn't have put me in spreadsheet land. That's not where I thrive."
— Deepali Vyas (03:36)
Definition & Application
(05:03) Unlike product-market fit, talent-market fit measures the alignment between a person’s wiring and the company’s current realities—stage, size, pressure, and culture—not just prestigious resumes or big-brand experience.
“You really have to ask yourself as a founder... Did that person make the logo, or did the logo make the person?”
— Deepali Vyas (05:39)
Classic Mismatch Example:
Founders, CEOs & Inflection Points
(06:45) Deepali reflects on her firm’s work on Uber’s CEO search, underscoring how company needs shift and leadership must evolve:
“There is an inflection point that happens... the CEO profile has to evolve based on the stage that the company is at.”
— Deepali Vyas (07:52)
Self-Audit Tool:
(10:09) Organizations—especially small teams—should regularly ask:
“The most dangerous CEO is not a weak one. It’s the almost-right one.”
— Deepali Vyas (10:55)
“High-profile founder removals have happened to men and women, but the pattern feels different for women. ... Women founders statistically raise less capital, have fewer deeply embedded board allies, and they get scrutinized earlier for leadership maturity. And that compounds under stress.”
— Deepali Vyas (12:28)
“I would say I was scrutinized like a Series A company versus a seed company as a female founder. That’s firsthand experience.”
— Deepali Vyas (15:41)
“What companies are making a mistake right now is there’s level one and then there’s level three. ... The missing middle is where the ROI is really at. ... I guarantee you the people that overcut now will over-hire again in the next pendulum swing.”
— Deepali Vyas (18:49)
Changing Aspirations & Career Structures
(21:46) Deepali describes how high compensation, stock options, and flexible work are leading younger workers toward “portfolio careers”—stacking different skills and income streams, often as independent or fractional consultants.
“The future of work is going to be everyone stacking skills, ... then say, hey, if I can do it here, I can do it across the board. And so they will stand up multiple income streams based on their expertise, ... that’s what a portfolio career looks like.”
— Deepali Vyas (21:48)
Generational Motivation & Passive Income
(24:16)
“Work motivation is shifting. It’s not disappearing.”
— Deepali Vyas (24:32)
The New Work Equation:
“Income is really leverage plus skill plus distribution.”
— Deepali Vyas (26:55)
Systemic Inertia
(28:11) Deepali advocates for rethinking work structures so benefits and mobility support careers that bounce between projects and companies.
“Most people feel stuck because they don’t have the understanding of what optionality looks like.”
— Deepali Vyas (29:14)
On Resume Blindness:
“Did that person make the logo, or did the logo make the person?”
— Deepali Vyas (05:39)
On Stage Matching:
“The most dangerous CEO is not a weak one. It’s the almost-right one.”
— Deepali Vyas (10:55)
On the Gendered Lens in Leadership Transitions:
“Women founders statistically raise less capital, have fewer deeply embedded board allies, and they get scrutinized earlier for leadership maturity.”
— Deepali Vyas (12:51)
On The Realities of AI Layoffs:
“The people that overcut now will over-hire again in the next pendulum swing.”
— Deepali Vyas (18:49)
On The New Work Equation:
“Income is really leverage plus skill, plus distribution.”
— Deepali Vyas (26:55)
Deepali wraps up by sharing ways to connect via her website (deepalivyas.com), LinkedIn, Instagram, TikTok, or email: hello@deepalivyas.com (29:31). Both host and guest agree: organizations serious about thriving must rethink how they hire, lead, and structure work for the future.
For more Founder’s Story episodes:
Visit IBH Media or subscribe wherever you get your podcasts.