Latest / Chief in Tech Deep Dive Shortcast / Chief in Tech S1E14 - Judy Dinn : Diversity, Empathy & Balance: Fostering Inclusivity in a Modern Workplace

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Chief in Tech S1E14 - Judy Dinn : Diversity, Empathy & Balance: Fostering Inclusivity in a Modern Workplace · Chief in Tech Deep Dive Shortcast

• 0:00
  You know, there's a specific lie that I think
• 0:02
  most of us were told, maybe around age five.
• 0:04
  Oh, yeah. It's a really comforting lie, usually
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  from a teacher or a parent. And it goes something
• 0:09
  like this. If you just keep your head down, you
• 0:12
  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
• 0:26
  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
• 1:01
  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
• 1:15
  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
• 1:44
  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
• 2:00
  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
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  tired, so I'm going to take on more work. But
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  it was different work. It was using a totally
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  different part of her brain. And this leads to
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  her disconnect rule. She realized that when you're
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  grinding on a single problem to 147, you lose
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  all objectivity. You get intense, but you stop
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  being smart. You lose the forest for the trees.
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  Exactly. Stepping away, whether to teach yoga
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  or just go on a real vacation, it resets your
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  strategic vision. She actually forces her team
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  to disconnect. No emails on vacation. Period.
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  That requires a lot of trust in your team to
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  handle things while you're gone. It does. But
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  she says if you don't disconnect, you get lost
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  in the conversation. You become reactive instead
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  of proactive. You're just swatting away emails
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  instead of actually thinking about architecture.
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  But here's the hard part. Judy Dinn is the CIO.
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  She gets to set the rules. What if you're a mid
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  -level manager and your boss is not Judy Dinn?
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  What if your boss demands you be online at 10
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  p .m.? Din addresses this with what she calls
• 13:10
  managing up, but it comes with a dose of tough
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  love. Okay. You have to be transparent. You have
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  to say, look, I am in a life stage where I have
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  a toddler. I cannot be online at 6 p .m. And
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  if the boss says too bad, then you have to have
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  the courage to leave. Well, walk away. She frames
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  it as a detour, not a dead end. If a role cannot
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  accommodate your current life stage, it is the
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  wrong role for right now. It doesn't mean you're
• 13:36
  not ambitious. It means you're playing the long
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  game. That's scary advice. It is. But staying
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  in a role that destroys your home life is scarier.
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  She emphasizes that careers are 30 or 40 years
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  long. You can take a lateral move or a slower
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  pace role for three years and then ramp back
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  up when the kids are in school. That isn't failure.
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  It's just pacing. So to recap the playbook here,
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  we have three pillars that are actually strategies.
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  Pillar one, diversity via participation, the
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  safety cycle. You have to speak up to be safe,
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  and you have to create safety for others. Use
• 14:08
  the buddy system. Use attribution. Pillar two.
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  Empathy as currency. It's not about being nice.
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  It's about making sure you are known by the jury
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  that decides your promotion. That 20 -minute
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  chat is a strategic investment. And pillar three.
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  Balance is a dynamic state. Define it for yourself.
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  Don't apologize for it. And realize that stepping
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  away actually makes you a better strategist when
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  you return. It's a powerful reframing of what
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  it means to be a heavy hitter. It's less about
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  the brute force of your own intellect and more
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  about the ecosystem you build around yourself.
• 14:40
  Absolutely. The Keep Your Head Down and Work
• 14:41
  Hard strategy is basically a solitary confinement
• 14:45
  cell. DIN's strategy is all about leveraging
• 14:48
  your team, your relationships, and your own mental
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  energy. We want to leave you with a final thought,
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  something to test DIN's missing sentence in your
• 14:58
  own life. Right. Think about that promotion meeting
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  we described. If your name came up today, right
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  now, and your manager asked your peers about
• 15:08
  you, would they have a story to tell? Would they
• 15:11
  say, oh, I was just talking to them about their
• 15:13
  marathon training, or, you know, they really
• 15:15
  helped me out with that project last week? Or
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  would they just say, I don't know, they seem
• 15:18
  to work hard? If it's the latter, you are in
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  the danger zone. You are. So here's your homework.
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  In your next meeting, just try the check -in.
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  Spend the first five minutes just being a human
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  being. It might feel awkward, it might feel inefficient,
• 15:31
  but see if it changes the energy in the room.
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  You might be surprised at how much faster the
• 15:36
  actual work gets done after that. That's it for
• 15:39
  this deep dive. Thanks for listening. Take care.