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Daniel Robbins interviews Deepali Vyas about the real reasons people get put on performance improvement plans, how founders can diagnose misalignment before it becomes a firing decision, and how CEO and C-suite profiles must evolve as companies scale. Deepali shares behind-the-scenes insight into executive hiring dynamics, including the power networks that shape boards and why women founders can face different patterns of removal. The episode closes with a clear view of what’s next: portfolio careers, fractional expertise, and a workforce increasingly driven by leverage, skill, and distribution.
Key Discussion Points
This Founder’s Story conversation turns hiring and “future of work” from buzzwords into a practical operating system for founders. Deepali Vyas leaves listeners with a clear message: build teams for fit, not prestige, and design organizations for the reality of how talent wants to work now, not how it worked ten years ago.
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So Deepali, 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 amazing PIP, put them on that,
and then basically get them out, like, whatever, or higher, slow, fire, fast. That was like,
you know, do these things, and 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? 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 a
wrong role, wrong stage, wrong manager, wrong pressure profile, but I think the uncomfortable truth
is that, you know, 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 underperforming
as a 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 the 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 from before, but like, what are they really, really good at? And then where's the energy fit?
Where does this work drain them versus what energizes them? If someone who would have asked me that
early on in my career, Dan, it would have been super obvious where I thrive versus where I
suck at details. Period. Full stop. I suck at it. But I am really good at it. Empowering people,
setting big vision, energizing people towards a really big goal. And if they would have seen
that early 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, well, I talked about autonomy fit, but like,
the stage fit, right? Like, is the company in a phase that 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, 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? So founders do obsess with product market fit, which is fair, right? But most of them
don't think about the talent market sit. 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 a founder hiring that person, 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 3000 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. So we had a guest on before Francis Frye, a Harvard professor and she helped the
transformation through Uber when it was the founder to the to the new CEO. And I was fascinated
to hear about this whole like founder CEO when the company skills you now need a new CEO because
of the fits of the company. What do you see around C sweet fit as the company scales over time?
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 it. It 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, you 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 a in in one direction, right? 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. 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 removed 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 and see if the people they do have
are correct? The audit, I would say like if you think about it from like a board level because
that's typically why these things come about. What stage are we actually in? 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? And then do the leaders in our organization,
whether it's at this small stage, but they're all basically leaders. Does that pattern history
match that pressure? Does past patterns predict future behavior? Can they handle it? That's the
diagnostic. The hard truth is sometimes the most dangerous CEO is not a weak one. It's the
almost right one. That's where 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 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 was going to be. So there's a lot of dynamics that get
played out in the boardroom. 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 I've talked to
some really well-known companies before, not on this 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. Why do you think this is happening? And is it related to what you
were just saying around the future of the company? Is it only, is it because there's not a lot of
women who are founding larger companies? What do you think it is? So I think that there'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 raised less capital have fewer,
deeply embedded board allies. And they get scrutinized earlier for leadership maturity. And that
compounds under stress. My, I'm blown. My mind is blown. Like, I never, the power dynamic, I never
even heard of this, to be honest, like the power dynamics of what's going, this is why I never
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It's money because I was too afraid of the power, giving up the power.
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 venture, even just by the way, the zero to a 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 first-hand experience.
Hope it changes, because I know I have your situation.
The amount of money going to women is very small. We just had the previous founder of task
rabbit who started her own VC firm now to hopefully try and solve this, but obviously it's something
huge. When you look at the future of what the workplace will be, a couple of years ago,
this was like the topic everywhere. Well, people go back to the office,
hybrid, then all of a sudden it became a topic again. And there was 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 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? 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
pushbacks and 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 at 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 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 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 seeing all these layoffs saying, well,
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 overhire 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 MIT came out with the study saying 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 co-pilot 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 budgets can approve, right? Or, you know, roadmaps can be approved. And that's going
to be a longer cycle. Now, block did this, you know, layoff. And I think that 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. 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 can 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, multi millionaires. 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, 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. 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 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 advise, 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. 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. It'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 a
hustle and grind. Like I'd say like older millennials enough, we were, you know, you and I like,
we got a hustle, we got a 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, you are kind to lump me into older millennial because I'm definitely not that.
I am much older than you, but 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 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, oh, wait, 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 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 income back there. And that's where it's going to win. The new
equation I'm going to say is income is really leverage plus skill plus distribution. I think
that's the equation. I've never, I think I've talked to over 1,400 people in six years. I've never
heard this before. 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 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 only option
I had. Like I wanted to move somewhere. So I had to be feeling 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. But damn, that's a structural thing, right? Because corporations
are not allowing that type of flow. Exactly. 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 30,000 feet 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
the savings account, et cetera, et cetera. But you are free 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 solo
manure 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 there of,
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. I feel like people and corporations need your help.
Yeah, that's right. The students like to me. So if they want to get in touch with you,
because they all need to, how can they do so? So they can reach me. I have my website,
depolyvias.com. I'm on Instagram and TikTok and LinkedIn and all of the things. But hello,
at depolyvias.com. They can reach me there. And then your book will come out eventually. We'll
have to read that. The fact that you're you're wearing Vios media sweater, like I need to get a sweater.
This has been great. I appreciate it. I 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. Appreciate it. The maps app that came with your phone, it's fine. If you enjoy waiting
and guessing and inefficient routes, or you could use MapQuest. MapQuest is back with live
directions, real-time traffic and faster routes. It moves when you move. Best of all, no
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Founder's Story
