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Chief in Tech S1E15 - Kate Prouty : How to Be an Organizational Change Maker · Chief in Tech Deep Dive Shortcast

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  Welcome to The Deep Dive, where we unpack huge
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  amounts of research and distill it all down to
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  the essentials you need to know. And today, we
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  are really digging into a big one. We are. We're
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  tracing the 25 -year evolution of a major tech
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  company, Akamai Technologies. It's really a story
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  about change, about how leadership has to mature.
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  And, you know, how a startup culture survives
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  that transition to becoming a, what, nearly $4
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  billion? global leader. So our guide on this
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  journey is Kate Prouty. She's the current CIO
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  of Akamai. Right, and she's the perfect person
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  to track this because she joined the company
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  way back in 1999, right at the beginning. She's
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  been in leadership there for over two decades.
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  And we need to set the scale here. Akamai is,
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  for many, basically the backbone of the internet.
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  They're handling content, security, cloud computing.
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  billions of times a day. So this isn't just about,
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  you know, changing the snacks in the break room.
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  No. This is a fundamental shift in the company's
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  DNA, all while managing this insane technical
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  complexity. So our mission for this deep dive
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  is to unpack the sources from Prouty's experience.
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  How did they actually drive that change from
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  the top down? And I think more importantly, what
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  parts of that that sort of wild 1999 culture,
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  did they have to leave behind to survive? Because
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  the big takeaway here is that change, well, it's
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  not really optional. OK, so let's jump in that
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  time capsule. Let's go back to 1999. What was
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  that startup environment really like? The sources,
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  they paint a very specific picture. It's that
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  high octane, late dot com era. Right. It's exhilarating.
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  You know, frenetic energy, food deliveries, and
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  my favorite detail. people literally on rollerblades
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  in the office. Rollerblades? I mean, that detail
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  says so much, but that pace, it wasn't just for
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  show, was it? There was a real technical need
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  for that speed. Oh, absolutely. They were building
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  a global content delivery network from scratch.
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  They had to be faster and louder than everyone.
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  And that desperation, it translated directly
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  into their culture. So how did they define that?
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  Their motto, and this was literally printed on
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  their walls, was the word obstreperous. Obstreperous.
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  I love that word. It's so... Noisy, defiant.
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  That was the whole point. It meant you were a
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  disrupter. You were making noise, demanding change.
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  The lines between jobs were, you know, intentionally
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  blurry. If you saw a problem, you just jumped
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  in. But this idea of healthy debate, it sounds
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  like it often tipped over into something, well,
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  less healthy. It did. The sources are pretty
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  clear that this culture was full of young, very
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  academic people. And it created this environment
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  of constant, intense confrontation. So the goal
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  wasn't collaboration? Not really. The goal was
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  often to be the smartest person in the room.
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  To actively search for the mistakes in your colleague's
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  work. Wow, that sounds incredibly stressful.
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  A real pressure cooker. It was. And they had
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  a mantra for it, you were behind. Jeez. Yeah.
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  And the way they recognized success just solidified
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  this whole individualistic, heroic thing. They
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  had something called the Titans Award. OK, the
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  Titans Award. Let me guess. It wasn't for the
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  best team player? Not at all. It was explicitly
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  for the superstar Titan individual contributor.
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  The one brilliant person whose Herculean solo
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  effort saved the day. So management, teamwork,
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  that was all secondary to just these heroic solo
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  acts. Totally. And the expectation was complete
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  and utter dedication. 15 plus hours a day in
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  the office was normal. It was a badge of honor
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  to sacrifice your personal life. People rarely
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  even talked about their lives outside of work.
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  So that culture, as exciting as it sounds, it
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  really had a shelf life. It was a ticking time
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  bomb. It was completely unsustainable. And that
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  connects to the bigger picture, right? The mandate
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  to evolve wasn't just about technology. It was
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  about, well... about scaling their humanity.
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  Akamai and Prouty basically grew up together.
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  And the sources show that the pressure for change
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  often came from very personal places. Yes, exactly.
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  Prouty mentions that she was one of the very
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  first people at Akamai to get pregnant back in
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  those early days. And if you look at how the
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  company handled that then versus now, I mean,
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  it just perfectly shows the massive gap they
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  had to cross. The contrast is it's really dramatic.
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  Back then, she was one of maybe five people in
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  the mother's group. Just five. Maternity leave
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  was rigid. 12 weeks just following the law and
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  zero paternity leave. It was seen as a concession
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  You know not a benefit and now you fast forward
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  the company has over 12 ,000 employees You just
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  can't ask thousands of adults with kids and mortgages
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  and real lives To operate like those 22 year
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  old rollerbladers the leadership finally realized
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  it The old culture was actively hurting their
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  ability to keep the senior people they needed
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  So their most precious asset, their people, was
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  being worn down. Exactly. The mindset had to
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  shift from, how much time can we get out of them,
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  to something more like, how do we support their
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  whole lives so they do better work? It's that
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  old saying, right? What got you here won't get
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  you there. It's so true. The heroic, chaotic
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  stuff that built the company in the first place
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  was never going to get them to that next stage
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  as a mature, multi -billion dollar organization.
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  Yeah. OK, this is where it gets really fascinating
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  to me. How does a company that literally rewarded
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  people for being at their desks for 15 hours,
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  how do they suddenly pivot to celebrating the
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  idea that you might never need to be in the office?
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  It was a massive, massive undertaking. They went
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  from that culture of mandatory face time to something
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  they call flex space, which lets employees choose
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  where they work best. And it's not just a policy
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  on paper. No, it's real. Over 80 % of their employees
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  now work four or more days a week from home.
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  So my question is, the one every manager listening
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  is probably thinking, how do you keep collaboration,
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  productivity, all of it going when 80 % of your
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  team is remote, especially coming from where
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  they came from? Well, it's a huge investment,
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  both technical and managerial. Technically, their
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  systems had to be flawless and cloud -ready.
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  But the managerial shift was the big one. You
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  had to stop managing by sight. Exactly. The focus
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  had to move from inputs, you know, did I see
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  you sitting there, to outcomes. Trust had to
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  become the default. Managers are trained to assess
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  results, not your proximity to the office. And
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  you mentioned that Titan Awards still exists,
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  but it means something different. That must have
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  required a total overhaul of how they review
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  performance. It did. The Titan is no longer the
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  solo superstar. So what is it now? The new definition
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  is all about collaborative impact, cross -functional
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  success, mentorship. The performance metrics
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  now explicitly reward you for sharing knowledge
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  for making the whole team succeed. So being a
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  brilliant jerk is no longer a viable career path
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  there. Not if you want to be a titan, no. It's
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  about channeling that old intellectual fire in
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  a way that's... you know, sustainable and positive.
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  They didn't ask people to stop being disruptive.
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  They just asked them to be constructively disruptive.
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  Yes. They institutionalized that obstreperous
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  spirit. They realized you can't rely on chaotic
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  arguments for innovation when you're a giant
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  global company. So they build formal structures
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  like their annual innovation challenge. Tell
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  me more about that. How does a formal structure
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  like that create safety? It gives a clear, safe
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  path for anyone, no matter their role, to pitch
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  an idea all the way up to the CEO for funding.
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  It empowers people to challenge the status quo
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  without the fear of, you know, personal backlash
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  if the idea doesn't work out. So it's structured
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  risk taking. It creates room to fail. That whole
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  idea of letting people burn down the couch, not
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  the house. Exactly. They made innovation a system,
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  not something dependent on a random confrontation.
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  The core values are still there. Disruption,
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  innovation. But now they're channeled through
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  a system built on trust. So let's bring this
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  home for the listener. What does all this mean
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  for someone who's in an organization right now
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  that feels stuck in its own 1999 mindset? Okay,
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  key takeaway number one. You don't have to wait
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  for the CEO to have an epiphany. Proudi is really
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  clear on this. You can be responsible for your
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  own culture. You can be the catalyst. You can
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  be the catalyst. If you see something that needs
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  to evolve, speak up. Even if it's just in your
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  small corner of the company. And that leads right
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  into the second big idea. Control your immediate
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  environment. Even if you can't change a whole
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  company, you can change your team. That micro
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  level change is so powerful. You can build trust,
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  respect, and safety right where you are. Set
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  clear expectations for teamwork. Hold your team
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  accountable for eliminating those little microaggressions.
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  Make your bubble a safe place for people to bring
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  their whole self to work wherever they're working
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  from. Right. And for anyone in a leadership role,
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  this all demands a huge shift in style. It's
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  about being authentic, not just copying the old
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  titans. Which brings us to the third takeaway.
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  This is about leading by example, but also learning
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  from, well, from bad examples. Yes. Prouty talks
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  about the power of the anti -mentor. The anti
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  -mentor. I think that's a brilliant concept.
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  What does that actually look like? It's about
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  deliberate observation. You watch the leader
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  who is technically great but relationally terrible,
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  the one who micromanages their remote team or
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  engages in that destructive personal kind of
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  debate. And you just take notes on what not to
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  do? You observe their actions and you consciously
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  vow, that is a behavior I will never ever repeat.
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  You're not copying their success, you're learning
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  from their failures. It's such a powerful way
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  to build your own authentic leadership style
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  instead of just mimicking the people who came
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  before you. Exactly. The end goal is authenticity.
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  Don't pretend you're a 1999 Titan in today's
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  world. It just won't work. Because the world
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  is constantly changing. The moment you get comfortable
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  is the moment you fall behind. And that is the
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  final warning. If you like how things are now,
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  great. But you have to constantly be challenging
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  yourself and adapting. Because, as the old Ikemae
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  saying goes, if you're standing still... You're
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  gonna be behind. You're gonna be behind. What
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  a journey. From a frenetic rollerblading startup
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  to this flexible, team -focused global company,
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  the lesson from Kate Prouty's 25 years is just
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  so clear. Evolution is not optional. It is absolutely
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  necessary for survival. And if you're feeling
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  challenged by change right now in your own work
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  or life, we should leave you with Prouty's favorite
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  quote on this. It really sums it all up. What
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  is it? If it doesn't challenge you, then it won't
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  change you. Powerful. So don't just wait for
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  change. Be the catalyst for it. Thank you for
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  joining us for the deep dive. We'll see you next
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  time.