WEBVTT

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You know, there's a specific lie that I think

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most of us were told, maybe around age five.

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Oh, yeah. It's a really comforting lie, usually

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from a teacher or a parent. And it goes something

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like this. If you just keep your head down, you

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follow the rules and you get straight A's, then

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success is basically a mathematical guarantee.

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Ah, the old myth of the meritocracy. Exactly.

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The idea that a career is like a vending machine.

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You put in the hard work coin, you press the

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button. And out comes the promotion. Out comes

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the promotion snack. And honestly, it is just

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exhausting to keep believing that, because then

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you hit the actual workforce, especially the

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corporate world, and you realize, oh, the vending

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machine is broken. You see these brilliant engineers

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or analysts, and they're stalling out in middle

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management, while other people who maybe aren't

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as technically gifted, they just seem to glide

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up the org chart. It's incredibly frustrating.

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I mean, it feels unfair, or at the very least

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illogical. But today's deep dive is really about

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debugging that exact error. We're looking at

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a fascinating talk and the career path of Judy

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Dinn. And for anyone who doesn't know the name,

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Dinn is a huge figure in fintech. She is currently

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the Chief Information Officer at TD Bank, America's

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most convenient bank. But what I love about her

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profile is that she's not a career administrator.

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She is a hardcore technologist. That's such a

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crucial distinction. She's a University of Waterloo

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grad that's math and computer science. For context,

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Waterloo is basically the MIT of the North for

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engineering. Oh, absolutely. She speaks the language

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of cloud computing, of APIs, microservices. She's

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built systems at JPMorgan Chase. multiple top

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-tier Canadian banks. Which is why her advice

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just, you know, hits differently for me. She's

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not an HR consultant telling engineers to be

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nicer. She's an engineer telling other engineers

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why their code by itself is not going to get

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them promoted. Precisely. We're going to unpack

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what she calls her three pillars of success.

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Diversity, empathy, and balance. And I know hearing

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those words might make you think of like a generic

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corporate poster in a break room. The hang in

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there kitty poster. Right. But the way she operationalizes

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them is genuinely surprising. This isn't fluff.

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It is a strategic playbook. We're going to look

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at the safety cycle in meetings, why work -life

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balance is a dangerous math problem, and the

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missing sentence in the whole equation for success.

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That missing sentence, I think, is the key to

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the entire thing. But let's start with her first

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pillar. Diversity. Now usually when executives

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talk about diversity they go straight to hiring

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stats or quotas. Din comes at this from a psychological

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angle first and specifically she focuses on insecurity.

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She drops a truth bomb right at the start of

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her talk she says, everyone is insecure. Everyone.

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Everyone. And she doesn't just mean the interns

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or the new hires. She means the CIO, the VP,

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the loudest, most confident person in the room.

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That is really hard to believe when you're sitting

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across from someone who seems to have all the

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answers. It is. But Dinn argues that even the

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most assertive leaders are often battling some

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form of imposter syndrome, that nagging fear

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that they're about to be found out. And she brings

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this up to just level the playing field. So the

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idea is, if you're sitting in a meeting feeling

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like you don't belong, Statistically, the person

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running the meeting feels a version of that too.

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So if everyone is scared, how does anything get

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done? It feels like that would just lead to paralysis.

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This is where she introduces the concept of the

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safety cycle. It's a feedback loop. Her premise

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is that feeling included actually reduces your

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anxiety. When your anxiety drops, you feel safe

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enough to participate. And then the participation

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itself creates even more safety. Correct. It

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reinforces itself. But the inverse is where it

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gets really dangerous for a company. If you don't

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feel included, you stay silent. And in Din's

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view, silence isn't just neutral, it's value

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destruction. Wow, that's a heavy statement. Value

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destruction. Well, think about it. It's the reality

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of a technical organization, right? If you're

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an engineer and you have a specific insight on

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a piece of code or you've spotted a risk in a

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project plan and you don't speak up because you're

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insecure. Then you might as well not be there.

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Your value to the organization in that moment

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is effectively zero. You become invisible. And

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invisibility leads to career stagnation. So inclusion

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isn't just some nice -to -have moral victory.

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It's an efficiency mechanism. It is an optimization

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of human capital. If you aren't hearing from

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everyone in the room, you are not getting the

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full brain power that you are paying for. OK,

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but just telling someone who is anxious to speak

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up is terrible advice. It is. It's like telling

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someone with insomnia to just sleep. But Din

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actually gets cactical here, which I really appreciated.

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She has a playbook for the actual mechanics of

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a meeting. She does. And she targets two groups,

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the leaders and the participants. Yeah. For leaders,

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her advice is pretty blunt. Stop talking. Ah,

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the smartest person in the room syndrome. Exactly.

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If you're leading, your job isn't to prove you

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know the answer. Your job is to facilitate, to

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draw out the quiet voices. But for the participants...

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especially those from underrepresented groups,

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she suggests what she calls the buddy system.

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This is basically the wingman concept applied

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to corporate strategy. It really is. So before

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a high stakes meeting, you find a confidant,

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someone you trust. You agree to debrief afterwards.

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You can ask, hey, did I sound crazy when I said

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that? Or did you notice that Mike cut me off

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three times? It validates your reality. It stops

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the gaslighting. It keeps you from spiraling

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into that maybe I don't belong here mindset.

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But then she goes a step further with something

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called attribution. I love this one. I love this

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one because I've seen the problem a thousand

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times. The idea heist. We all have. A junior

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employee, often a woman or a person of color,

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suggests a solution. Crickets. Silence. Nothing.

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Five minutes later, Bob suggests the exact same

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thing, and the room just explodes with applause.

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Great job, Bob. You really cracked the code.

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Din's advice is, be the person who corrects the

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record. You don't have to be aggressive about

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it. You don't have to start a fight. You just

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say, actually, Brenda made that point five minutes

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ago, and I agree. It's the right move. That is

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a power move. It's allyship, sure, but it's also

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leadership. You are policing the integrity of

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the conversation. And that's why Din says inclusion.

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is a more critical metric than diversity. Diversity

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is just the stats. It's who's in the room. Inclusion

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is the mechanic. It's the attribution, the buddy

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system, the facilitation that actually makes

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the diversity work. Right. Without the mechanics,

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you just have a diverse group of people sitting

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there in silence. Exactly. But you can't have

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a diverse room if the people don't exist in the

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industry to begin with. And DIN addresses the

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pipeline problem in tech. Frankly, a lot of executives

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use this as an excuse. They say, we'd love to

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hire more women coders, but, you know, there

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aren't any graduating. Dinn acknowledges the

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reality. The numbers are low. But she rejects

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the passivity of that statement. She treats it

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like a supply chain problem. If you don't have

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the materials you need, you have to go upstream

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and manufacture them yourself. Which is what

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led her to co -founding Think About Math with

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the University of Waterloo. Right. She identified

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the bottleneck. It wasn't at university hiring.

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It was in high school. Specifically, high school

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girls who are on the verge of graduation. That's

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where the drop -off happens. They opt out of

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advanced math because they just don't see themselves

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in that world. So she didn't just start a scholarship.

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She built a community. That's the key word, community.

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The program isn't just tutoring. It brings these

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girls together to show them, look, there are

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hundreds of other girls just like you who love

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calculus. It normalizes their passion. It goes

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right back to that safety cycle again. If you

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see your tribe, you feel safe enough to pursue

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the career. And it works. This program has been

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running for over a decade now, and the enrollment

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of women in STEM at Waterloo has measurably increased.

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She proved that you can build your own pipeline

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if you start early enough. And just to put a

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cap on this diversity pillar, she's very clear

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this is not charity work. No. She cites research

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from catalysts. Diverse teams just perform better

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financially. They innovate faster. Din's a CIO.

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She cares about output. She sees diversity as

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a competitive advantage, not a PR requirement.

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Which brings us to pillar two, empathy. And this

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is where we get back to that missing sentence

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we teased at the top. Right. So going back to

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that kindergarten line, the standard advice is

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work hard, be smart, get the credentials. Din

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says that sentence is incomplete. The full sentence

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should be work hard, be smart, and build relationships.

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That sounds a little soft. Build relationships.

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It sounds like something you say at a mixer while

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holding a lukewarm sparkling water. It does,

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until you look at her promotion reality check.

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This part actually scared me a little when I

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read it. OK, walk us through it. So picture a

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promotion meeting. You aren't in the room. Your

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boss is there. along with, say, five other department

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heads or VPs. Your boss puts your name forward

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for a step up. OK, I've done the work. My code

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is clean. I hit my deadlines. I'm ready. Doesn't

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matter yet. Your boss asks the other five leaders,

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so what do you all think of them? And if the

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room goes silent, or if they say, I don't really

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know them, you are dead in the water. So my merit

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isn't enough. Merit gets you on the list. Relationships

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get you the vote. Promotions are a consensus

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game. If you are invisible to everyone except

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your direct manager, you're a risky bet. You

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need a room full of people nodding their heads,

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not just one person. So how do you get them nodding?

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This is where empathy comes in as a tactic. Din

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doesn't define empathy as, you know, crying with

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your co -workers or being a therapist. No. She

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defines it as the mechanism for being known.

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And she suggests a tactic that I honestly struggled

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with at first, the check -in. This is the idea

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of starting every meeting with personal conversation.

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Every single one. Even the crisis meetings. Even

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the budget reviews. How are the kids? Did you

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run that 5K? How's the renovation going? I have

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to play devil's advocate here. If I have a 30

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-minute standup and we spend 20 minutes talking

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about kitchen renovations, isn't that inefficient?

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We're burning payroll. That sounds like bad management.

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That was my first reaction, too. Yeah. But Din

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argues that you are looking at the ROI of the

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meeting, not the ROI of the relationship. Explain

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that difference. If I spend those 20 minutes

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connecting with you as a human, I'm building

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social capital. Later, when I need you to approve

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a risky budget or when I need your team to work

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late or, look, when I screw up and I need forgiveness,

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you're going to say yes because you know me.

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You trust my intent. It removes friction from

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the actual work. Exactly. If you skip the empathy,

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every single transaction is cold. If I don't

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know you and you bring me a problem, I might

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assume you're annoying or incompetent. If I know

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you, I assume you have positive intent. Empathy

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buys you the benefit of the doubt. And in a massive

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organization like a bank, the benefit of doubt

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is the most valuable currency there is. So the

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20 minutes isn't wasted time. It's an investment

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in future speed. It's grease for the gears. Without

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it, the machine just grinds to a halt. That's

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a really compelling reframing. It turns small

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talk into strategy. OK, let's move to the third

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pillar, balance. This is the one everyone claims

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to want, but nobody seems to know how to get.

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And Din explicitly states that she hates the

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question, how do you achieve work -life balance?

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Why? Is it because she doesn't believe in it?

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No, not at all. It's because the question implies

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there's a formula. Right. It implies there's

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a white answer, where you can solve for X. You

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know, 33 % work, 33 % family, 33 % sleep. And

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she says that's just nonsense. Total nonsense.

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She argues that balance is dynamic. It changes

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based on your life stage. When she was fresh

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out of Waterloo, maybe balance was 90 % work

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because she was building her foundation. When

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she had kids, the whole equation broke. She shared

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a pretty vulnerable story about burning out during

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that time. She did. She completely hit a wall.

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And what she did next is so fascinating. She

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didn't just take a nap or a week off. She trained

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to become a nutritionist and a yoga teacher.

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While working in banking. While working in high

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finance, yes. That seems counterintuitive. I'm

00:12:13.379 --> 00:12:15.139
tired, so I'm going to take on more work. But

00:12:15.139 --> 00:12:16.799
it was different work. It was using a totally

00:12:16.799 --> 00:12:19.059
different part of her brain. And this leads to

00:12:19.059 --> 00:12:21.860
her disconnect rule. She realized that when you're

00:12:21.860 --> 00:12:24.879
grinding on a single problem to 147, you lose

00:12:24.879 --> 00:12:27.700
all objectivity. You get intense, but you stop

00:12:27.700 --> 00:12:29.940
being smart. You lose the forest for the trees.

00:12:30.200 --> 00:12:33.019
Exactly. Stepping away, whether to teach yoga

00:12:33.019 --> 00:12:36.059
or just go on a real vacation, it resets your

00:12:36.059 --> 00:12:38.419
strategic vision. She actually forces her team

00:12:38.419 --> 00:12:42.240
to disconnect. No emails on vacation. Period.

00:12:42.379 --> 00:12:44.779
That requires a lot of trust in your team to

00:12:44.779 --> 00:12:47.549
handle things while you're gone. It does. But

00:12:47.549 --> 00:12:49.970
she says if you don't disconnect, you get lost

00:12:49.970 --> 00:12:52.629
in the conversation. You become reactive instead

00:12:52.629 --> 00:12:55.070
of proactive. You're just swatting away emails

00:12:55.070 --> 00:12:56.830
instead of actually thinking about architecture.

00:12:57.110 --> 00:12:59.850
But here's the hard part. Judy Dinn is the CIO.

00:13:00.149 --> 00:13:02.889
She gets to set the rules. What if you're a mid

00:13:02.889 --> 00:13:05.330
-level manager and your boss is not Judy Dinn?

00:13:05.490 --> 00:13:08.110
What if your boss demands you be online at 10

00:13:08.110 --> 00:13:10.669
p .m.? Din addresses this with what she calls

00:13:10.669 --> 00:13:13.409
managing up, but it comes with a dose of tough

00:13:13.409 --> 00:13:15.690
love. Okay. You have to be transparent. You have

00:13:15.690 --> 00:13:17.889
to say, look, I am in a life stage where I have

00:13:17.889 --> 00:13:20.909
a toddler. I cannot be online at 6 p .m. And

00:13:20.909 --> 00:13:23.289
if the boss says too bad, then you have to have

00:13:23.289 --> 00:13:27.750
the courage to leave. Well, walk away. She frames

00:13:27.750 --> 00:13:31.830
it as a detour, not a dead end. If a role cannot

00:13:31.830 --> 00:13:33.990
accommodate your current life stage, it is the

00:13:33.990 --> 00:13:36.250
wrong role for right now. It doesn't mean you're

00:13:36.250 --> 00:13:38.659
not ambitious. It means you're playing the long

00:13:38.659 --> 00:13:41.600
game. That's scary advice. It is. But staying

00:13:41.600 --> 00:13:44.159
in a role that destroys your home life is scarier.

00:13:44.740 --> 00:13:47.679
She emphasizes that careers are 30 or 40 years

00:13:47.679 --> 00:13:50.740
long. You can take a lateral move or a slower

00:13:50.740 --> 00:13:52.940
pace role for three years and then ramp back

00:13:52.940 --> 00:13:55.139
up when the kids are in school. That isn't failure.

00:13:55.220 --> 00:13:58.240
It's just pacing. So to recap the playbook here,

00:13:58.480 --> 00:14:01.179
we have three pillars that are actually strategies.

00:14:01.259 --> 00:14:04.139
Pillar one, diversity via participation, the

00:14:04.139 --> 00:14:06.250
safety cycle. You have to speak up to be safe,

00:14:06.570 --> 00:14:08.669
and you have to create safety for others. Use

00:14:08.669 --> 00:14:11.610
the buddy system. Use attribution. Pillar two.

00:14:12.070 --> 00:14:14.710
Empathy as currency. It's not about being nice.

00:14:14.730 --> 00:14:16.950
It's about making sure you are known by the jury

00:14:16.950 --> 00:14:19.570
that decides your promotion. That 20 -minute

00:14:19.570 --> 00:14:22.529
chat is a strategic investment. And pillar three.

00:14:23.029 --> 00:14:25.450
Balance is a dynamic state. Define it for yourself.

00:14:25.690 --> 00:14:28.110
Don't apologize for it. And realize that stepping

00:14:28.110 --> 00:14:29.970
away actually makes you a better strategist when

00:14:29.970 --> 00:14:32.610
you return. It's a powerful reframing of what

00:14:32.610 --> 00:14:35.149
it means to be a heavy hitter. It's less about

00:14:35.149 --> 00:14:37.210
the brute force of your own intellect and more

00:14:37.210 --> 00:14:39.509
about the ecosystem you build around yourself.

00:14:40.049 --> 00:14:41.990
Absolutely. The Keep Your Head Down and Work

00:14:41.990 --> 00:14:45.669
Hard strategy is basically a solitary confinement

00:14:45.669 --> 00:14:48.830
cell. DIN's strategy is all about leveraging

00:14:48.830 --> 00:14:52.509
your team, your relationships, and your own mental

00:14:52.509 --> 00:14:55.730
energy. We want to leave you with a final thought,

00:14:55.889 --> 00:14:58.769
something to test DIN's missing sentence in your

00:14:58.769 --> 00:15:01.850
own life. Right. Think about that promotion meeting

00:15:01.850 --> 00:15:05.190
we described. If your name came up today, right

00:15:05.190 --> 00:15:08.129
now, and your manager asked your peers about

00:15:08.129 --> 00:15:11.370
you, would they have a story to tell? Would they

00:15:11.370 --> 00:15:13.129
say, oh, I was just talking to them about their

00:15:13.129 --> 00:15:15.149
marathon training, or, you know, they really

00:15:15.149 --> 00:15:16.769
helped me out with that project last week? Or

00:15:16.769 --> 00:15:18.210
would they just say, I don't know, they seem

00:15:18.210 --> 00:15:20.750
to work hard? If it's the latter, you are in

00:15:20.750 --> 00:15:23.490
the danger zone. You are. So here's your homework.

00:15:23.679 --> 00:15:26.120
In your next meeting, just try the check -in.

00:15:26.279 --> 00:15:28.419
Spend the first five minutes just being a human

00:15:28.419 --> 00:15:31.299
being. It might feel awkward, it might feel inefficient,

00:15:31.980 --> 00:15:33.940
but see if it changes the energy in the room.

00:15:34.320 --> 00:15:36.500
You might be surprised at how much faster the

00:15:36.500 --> 00:15:39.620
actual work gets done after that. That's it for

00:15:39.620 --> 00:15:41.960
this deep dive. Thanks for listening. Take care.
