You know, there's a specific lie that I think
most of us were told, maybe around age five.
Oh, yeah. It's a really comforting lie, usually
from a teacher or a parent. And it goes something
like this. If you just keep your head down, you
follow the rules and you get straight A's, then
success is basically a mathematical guarantee.
Ah, the old myth of the meritocracy. Exactly.
The idea that a career is like a vending machine.
You put in the hard work coin, you press the
button. And out comes the promotion. Out comes
the promotion snack. And honestly, it is just
exhausting to keep believing that, because then
you hit the actual workforce, especially the
corporate world, and you realize, oh, the vending
machine is broken. You see these brilliant engineers
or analysts, and they're stalling out in middle
management, while other people who maybe aren't
as technically gifted, they just seem to glide
up the org chart. It's incredibly frustrating.
I mean, it feels unfair, or at the very least
illogical. But today's deep dive is really about
debugging that exact error. We're looking at
a fascinating talk and the career path of Judy
Dinn. And for anyone who doesn't know the name,
Dinn is a huge figure in fintech. She is currently
the Chief Information Officer at TD Bank, America's
most convenient bank. But what I love about her
profile is that she's not a career administrator.
She is a hardcore technologist. That's such a
crucial distinction. She's a University of Waterloo
grad that's math and computer science. For context,
Waterloo is basically the MIT of the North for
engineering. Oh, absolutely. She speaks the language
of cloud computing, of APIs, microservices. She's
built systems at JPMorgan Chase. multiple top
-tier Canadian banks. Which is why her advice
just, you know, hits differently for me. She's
not an HR consultant telling engineers to be
nicer. She's an engineer telling other engineers
why their code by itself is not going to get
them promoted. Precisely. We're going to unpack
what she calls her three pillars of success.
Diversity, empathy, and balance. And I know hearing
those words might make you think of like a generic
corporate poster in a break room. The hang in
there kitty poster. Right. But the way she operationalizes
them is genuinely surprising. This isn't fluff.
It is a strategic playbook. We're going to look
at the safety cycle in meetings, why work -life
balance is a dangerous math problem, and the
missing sentence in the whole equation for success.
That missing sentence, I think, is the key to
the entire thing. But let's start with her first
pillar. Diversity. Now usually when executives
talk about diversity they go straight to hiring
stats or quotas. Din comes at this from a psychological
angle first and specifically she focuses on insecurity.
She drops a truth bomb right at the start of
her talk she says, everyone is insecure. Everyone.
Everyone. And she doesn't just mean the interns
or the new hires. She means the CIO, the VP,
the loudest, most confident person in the room.
That is really hard to believe when you're sitting
across from someone who seems to have all the
answers. It is. But Dinn argues that even the
most assertive leaders are often battling some
form of imposter syndrome, that nagging fear
that they're about to be found out. And she brings
this up to just level the playing field. So the
idea is, if you're sitting in a meeting feeling
like you don't belong, Statistically, the person
running the meeting feels a version of that too.
So if everyone is scared, how does anything get
done? It feels like that would just lead to paralysis.
This is where she introduces the concept of the
safety cycle. It's a feedback loop. Her premise
is that feeling included actually reduces your
anxiety. When your anxiety drops, you feel safe
enough to participate. And then the participation
itself creates even more safety. Correct. It
reinforces itself. But the inverse is where it
gets really dangerous for a company. If you don't
feel included, you stay silent. And in Din's
view, silence isn't just neutral, it's value
destruction. Wow, that's a heavy statement. Value
destruction. Well, think about it. It's the reality
of a technical organization, right? If you're
an engineer and you have a specific insight on
a piece of code or you've spotted a risk in a
project plan and you don't speak up because you're
insecure. Then you might as well not be there.
Your value to the organization in that moment
is effectively zero. You become invisible. And
invisibility leads to career stagnation. So inclusion
isn't just some nice -to -have moral victory.
It's an efficiency mechanism. It is an optimization
of human capital. If you aren't hearing from
everyone in the room, you are not getting the
full brain power that you are paying for. OK,
but just telling someone who is anxious to speak
up is terrible advice. It is. It's like telling
someone with insomnia to just sleep. But Din
actually gets cactical here, which I really appreciated.
She has a playbook for the actual mechanics of
a meeting. She does. And she targets two groups,
the leaders and the participants. Yeah. For leaders,
her advice is pretty blunt. Stop talking. Ah,
the smartest person in the room syndrome. Exactly.
If you're leading, your job isn't to prove you
know the answer. Your job is to facilitate, to
draw out the quiet voices. But for the participants...
especially those from underrepresented groups,
she suggests what she calls the buddy system.
This is basically the wingman concept applied
to corporate strategy. It really is. So before
a high stakes meeting, you find a confidant,
someone you trust. You agree to debrief afterwards.
You can ask, hey, did I sound crazy when I said
that? Or did you notice that Mike cut me off
three times? It validates your reality. It stops
the gaslighting. It keeps you from spiraling
into that maybe I don't belong here mindset.
But then she goes a step further with something
called attribution. I love this one. I love this
one because I've seen the problem a thousand
times. The idea heist. We all have. A junior
employee, often a woman or a person of color,
suggests a solution. Crickets. Silence. Nothing.
Five minutes later, Bob suggests the exact same
thing, and the room just explodes with applause.
Great job, Bob. You really cracked the code.
Din's advice is, be the person who corrects the
record. You don't have to be aggressive about
it. You don't have to start a fight. You just
say, actually, Brenda made that point five minutes
ago, and I agree. It's the right move. That is
a power move. It's allyship, sure, but it's also
leadership. You are policing the integrity of
the conversation. And that's why Din says inclusion.
is a more critical metric than diversity. Diversity
is just the stats. It's who's in the room. Inclusion
is the mechanic. It's the attribution, the buddy
system, the facilitation that actually makes
the diversity work. Right. Without the mechanics,
you just have a diverse group of people sitting
there in silence. Exactly. But you can't have
a diverse room if the people don't exist in the
industry to begin with. And DIN addresses the
pipeline problem in tech. Frankly, a lot of executives
use this as an excuse. They say, we'd love to
hire more women coders, but, you know, there
aren't any graduating. Dinn acknowledges the
reality. The numbers are low. But she rejects
the passivity of that statement. She treats it
like a supply chain problem. If you don't have
the materials you need, you have to go upstream
and manufacture them yourself. Which is what
led her to co -founding Think About Math with
the University of Waterloo. Right. She identified
the bottleneck. It wasn't at university hiring.
It was in high school. Specifically, high school
girls who are on the verge of graduation. That's
where the drop -off happens. They opt out of
advanced math because they just don't see themselves
in that world. So she didn't just start a scholarship.
She built a community. That's the key word, community.
The program isn't just tutoring. It brings these
girls together to show them, look, there are
hundreds of other girls just like you who love
calculus. It normalizes their passion. It goes
right back to that safety cycle again. If you
see your tribe, you feel safe enough to pursue
the career. And it works. This program has been
running for over a decade now, and the enrollment
of women in STEM at Waterloo has measurably increased.
She proved that you can build your own pipeline
if you start early enough. And just to put a
cap on this diversity pillar, she's very clear
this is not charity work. No. She cites research
from catalysts. Diverse teams just perform better
financially. They innovate faster. Din's a CIO.
She cares about output. She sees diversity as
a competitive advantage, not a PR requirement.
Which brings us to pillar two, empathy. And this
is where we get back to that missing sentence
we teased at the top. Right. So going back to
that kindergarten line, the standard advice is
work hard, be smart, get the credentials. Din
says that sentence is incomplete. The full sentence
should be work hard, be smart, and build relationships.
That sounds a little soft. Build relationships.
It sounds like something you say at a mixer while
holding a lukewarm sparkling water. It does,
until you look at her promotion reality check.
This part actually scared me a little when I
read it. OK, walk us through it. So picture a
promotion meeting. You aren't in the room. Your
boss is there. along with, say, five other department
heads or VPs. Your boss puts your name forward
for a step up. OK, I've done the work. My code
is clean. I hit my deadlines. I'm ready. Doesn't
matter yet. Your boss asks the other five leaders,
so what do you all think of them? And if the
room goes silent, or if they say, I don't really
know them, you are dead in the water. So my merit
isn't enough. Merit gets you on the list. Relationships
get you the vote. Promotions are a consensus
game. If you are invisible to everyone except
your direct manager, you're a risky bet. You
need a room full of people nodding their heads,
not just one person. So how do you get them nodding?
This is where empathy comes in as a tactic. Din
doesn't define empathy as, you know, crying with
your co -workers or being a therapist. No. She
defines it as the mechanism for being known.
And she suggests a tactic that I honestly struggled
with at first, the check -in. This is the idea
of starting every meeting with personal conversation.
Every single one. Even the crisis meetings. Even
the budget reviews. How are the kids? Did you
run that 5K? How's the renovation going? I have
to play devil's advocate here. If I have a 30
-minute standup and we spend 20 minutes talking
about kitchen renovations, isn't that inefficient?
We're burning payroll. That sounds like bad management.
That was my first reaction, too. Yeah. But Din
argues that you are looking at the ROI of the
meeting, not the ROI of the relationship. Explain
that difference. If I spend those 20 minutes
connecting with you as a human, I'm building
social capital. Later, when I need you to approve
a risky budget or when I need your team to work
late or, look, when I screw up and I need forgiveness,
you're going to say yes because you know me.
You trust my intent. It removes friction from
the actual work. Exactly. If you skip the empathy,
every single transaction is cold. If I don't
know you and you bring me a problem, I might
assume you're annoying or incompetent. If I know
you, I assume you have positive intent. Empathy
buys you the benefit of the doubt. And in a massive
organization like a bank, the benefit of doubt
is the most valuable currency there is. So the
20 minutes isn't wasted time. It's an investment
in future speed. It's grease for the gears. Without
it, the machine just grinds to a halt. That's
a really compelling reframing. It turns small
talk into strategy. OK, let's move to the third
pillar, balance. This is the one everyone claims
to want, but nobody seems to know how to get.
And Din explicitly states that she hates the
question, how do you achieve work -life balance?
Why? Is it because she doesn't believe in it?
No, not at all. It's because the question implies
there's a formula. Right. It implies there's
a white answer, where you can solve for X. You
know, 33 % work, 33 % family, 33 % sleep. And
she says that's just nonsense. Total nonsense.
She argues that balance is dynamic. It changes
based on your life stage. When she was fresh
out of Waterloo, maybe balance was 90 % work
because she was building her foundation. When
she had kids, the whole equation broke. She shared
a pretty vulnerable story about burning out during
that time. She did. She completely hit a wall.
And what she did next is so fascinating. She
didn't just take a nap or a week off. She trained
to become a nutritionist and a yoga teacher.
While working in banking. While working in high
finance, yes. That seems counterintuitive. I'm
tired, so I'm going to take on more work. But
it was different work. It was using a totally
different part of her brain. And this leads to
her disconnect rule. She realized that when you're
grinding on a single problem to 147, you lose
all objectivity. You get intense, but you stop
being smart. You lose the forest for the trees.
Exactly. Stepping away, whether to teach yoga
or just go on a real vacation, it resets your
strategic vision. She actually forces her team
to disconnect. No emails on vacation. Period.
That requires a lot of trust in your team to
handle things while you're gone. It does. But
she says if you don't disconnect, you get lost
in the conversation. You become reactive instead
of proactive. You're just swatting away emails
instead of actually thinking about architecture.
But here's the hard part. Judy Dinn is the CIO.
She gets to set the rules. What if you're a mid
-level manager and your boss is not Judy Dinn?
What if your boss demands you be online at 10
p .m.? Din addresses this with what she calls
managing up, but it comes with a dose of tough
love. Okay. You have to be transparent. You have
to say, look, I am in a life stage where I have
a toddler. I cannot be online at 6 p .m. And
if the boss says too bad, then you have to have
the courage to leave. Well, walk away. She frames
it as a detour, not a dead end. If a role cannot
accommodate your current life stage, it is the
wrong role for right now. It doesn't mean you're
not ambitious. It means you're playing the long
game. That's scary advice. It is. But staying
in a role that destroys your home life is scarier.
She emphasizes that careers are 30 or 40 years
long. You can take a lateral move or a slower
pace role for three years and then ramp back
up when the kids are in school. That isn't failure.
It's just pacing. So to recap the playbook here,
we have three pillars that are actually strategies.
Pillar one, diversity via participation, the
safety cycle. You have to speak up to be safe,
and you have to create safety for others. Use
the buddy system. Use attribution. Pillar two.
Empathy as currency. It's not about being nice.
It's about making sure you are known by the jury
that decides your promotion. That 20 -minute
chat is a strategic investment. And pillar three.
Balance is a dynamic state. Define it for yourself.
Don't apologize for it. And realize that stepping
away actually makes you a better strategist when
you return. It's a powerful reframing of what
it means to be a heavy hitter. It's less about
the brute force of your own intellect and more
about the ecosystem you build around yourself.
Absolutely. The Keep Your Head Down and Work
Hard strategy is basically a solitary confinement
cell. DIN's strategy is all about leveraging
your team, your relationships, and your own mental
energy. We want to leave you with a final thought,
something to test DIN's missing sentence in your
own life. Right. Think about that promotion meeting
we described. If your name came up today, right
now, and your manager asked your peers about
you, would they have a story to tell? Would they
say, oh, I was just talking to them about their
marathon training, or, you know, they really
helped me out with that project last week? Or
would they just say, I don't know, they seem
to work hard? If it's the latter, you are in
the danger zone. You are. So here's your homework.
In your next meeting, just try the check -in.
Spend the first five minutes just being a human
being. It might feel awkward, it might feel inefficient,
but see if it changes the energy in the room.
You might be surprised at how much faster the
actual work gets done after that. That's it for
this deep dive. Thanks for listening. Take care.