WEBVTT

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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.
