The Imposter Episode: Why Tech’s Best People Feel Like Frauds

There’s a quiet crisis running through IT leadership that nobody names in the meeting: the certainty that you’re in over your head, and that any minute now, someone’s going to find out. It comes with the job. And for women in tech, there’s a second layer underneath.

In this episode of The Catalyst, from Softchoice, a World Wide Technology Company, host Katey Teekasingh sits with three women who’ve lived imposter syndrome from every altitude: an IT director who wasn’t the first pick for her role, a five-time CTO who argues the field itself is the problem, and an MIT scientist who built a whole technology field while the engineering world dismissed her work — then won one of its highest honors.

Their answers about how to lead through doubt without faking it will reframe what most IT leaders quietly carry.

Key takeaways

• Why getting promoted for being the best engineer sets you up to feel like a fraud — and why it’s structural, not personal
• The second layer of doubt women in tech describe — the “merit, or a box to check?” question that follows them into every room
• How a top scientist reacted to winning one of engineering’s highest honors (hint: her first thought was “is this a scam?”)
• Three different strategies for leading through uncertainty — without pretending it isn’t there

Guest credentials

Rosalind Picard, ScD — Founder and Director of the Affective Computing Research Group at the MIT Media Lab; co-founder of Empatica and Affectiva; 2026 recipient of the IEEE Medal for Innovations in Healthcare Technology.

Meri Williams — Chief Technology Officer at Pleo; five-time CTO across fintech, retail, banking, and biotech; previously scaled the team that built GOV.UK at the UK’s Government Digital Service.

Julie Szaj — Director of Organizational Change Management at Washington University; 25+ years across education, learning design, and technology leadership.

About Our Sponsor

This episode is brought to you by HP, in partnership with Softchoice. HP helps organizations shape the future of work with AI-powered solutions across devices, printing, and services. 

Learn more at https://www.softchoice.com/technology-partners/hp

Hashtags

#TheCatalyst #Softchoice #HP #ITLeadership #ImposterSyndrome #WomenInTech #CTO #DigitalTransformation #MidMarketIT

Show Notes & Resources

Connect with our guests:

• Rosalind Picard — MIT Media Lab Affective Computing Group: media.mit.edu/groups/affective-computing
• Meri Williams — Pleo: pleo.io
• Julie Szaj — Washington University in St. Louis: wustl.edu

Referenced in the episode:

• Affective Computing (1997) by Rosalind Picard — the founding text of the field
• IEEE Medal for Innovations in Healthcare Technology — 2026 recipient: Rosalind Picard
• Empatica — wearable health technology co-founded by Picard: empatica.com

Learn more about HP’s partnership with Softchoice: https://www.softchoice.com/technology-partners/hp

The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology. 

Transcript

Producer 0:02

This episode of the Catalyst is brought to you by HP in partnership with SoftChoice. HP helps organizations shape the future of work with AI-powered solutions across devices, printing, and services designed to accelerate transformation and fuel business growth. Visit SoftChoice.com slash HP or click the link in the description to learn more.

Katey 0:36

There's a feeling a lot of people and technology carry around and almost never say out loud. It shows up right before a big meeting. It sits in your chest and it sounds something like this.

Julie 0:50

You know, just sweating bullets of, oh crap, they're gonna ask me something and I'm not gonna know. And then I'm gonna feel like an idiot. That's Julie.

Katey 1:01

She runs a technology team at a major university. And when she stepped into her leadership role, something flipped.

Julie 1:09

There's been a title switch, has been turned on, and all of a sudden I'm supposed to know everything.

Katey 1:14

One day, you're the person who does the work. The next day, you're the person who's supposed to have all the answers, and you don't. Nobody does. But the fear that someone's about to find that out is a specific kind of dread. It even has a name: Imposter syndrome. We talked to a lot of people for this episode. IT directors, CTOs, people who lead teams and budgets and systems most of their company doesn't understand. And almost every one of them told us some version of Julie's fear.

Rosalind 1:53

Almost everyone. For me, I've never felt that I might be discovered as not belonging.

Katey 2:01

That's Rosalind Picard, a professor at MIT. She invented a whole field of technology, the kind that's now inside the smartwatch on your wrist and the AI on your phone. And in 2026, she won one of the highest honors in all of engineering. By every measure that's supposed to make a person feel like they belong, like she belongs. So when Rosalind tells you the doubt was never hers, that's worth digging into.

Meri 3:38

We were promoted on the basis of knowing a lot, understanding systems well, being able to cope when they uh went wrong, being able to fix things when they broke.

Katey 3:48

That's Mary Williams. They've been a chief technology officer five times over, at a bank, at a retailer, at fintech companies. When they describe what it's like to get promoted in tech, they describe a trap.

Meri 4:02

When we become leaders of areas that we're not as fluent in, that we're not as detailed in, is super uncomfortable because we have to get to grips with a whole new area and continue to maintain our technical depth in the area we came from.

Katey 4:21

Here's the trap laid out plainly. You get promoted for being the best engineer in the room. And the reward for being the best engineer is a job that's no longer about engineering. Suddenly, you're responsible for security. And you've never worked in security for the front end when you came up on the back end for a dozen specialties you were never an expert in. And everyone around you assumes you're an expert in all of them.

Meri 4:52

I'm not a security expert, but I'm still responsible for security. I'm not a UX expert, but I'm quite often responsible for quite a lot of the experience of using the product.

Julie 5:01

And then there's Julie. So my name is Julie Shy, and I'm the director. Okay, wash you. I'm the director of organizational change management.

Katey 5:12

Julie echoes what Mary said about always feeling behind because the field doesn't sit still while you catch up.

Julie 5:19

It's changing all the time. We're just constantly trying to keep up with everything that's happening. And it's exhausting. It is absolutely exhausting to try to keep up with the speed in which technology changes.

Katey 5:35

Mary thinks there's something even more specific going on in tech. Something structural. It's not just that the work is hard, it's that the leap into leadership is a leap nobody trained you for.

Meri 5:48

We take the most competent technical people and promote them into management without equipping them for management at all. And that just causes this immense feeling of imposter syndrome because we actually don't know what we're doing when we become managers a lot of the time.

Katey 6:05

And then there's the loneliness of it, because the one thing you can't do in that chair is admit how unprepared you actually feel.

Meri 6:14

If you're the most technical person in a business, it's a super lonely role because you can't really tell your team how on how unprepared you feel and how worried you are about stuff because they might lose confidence in you. You definitely can't tell all the other execs that you're maybe not uh not on top of everything.

Katey 6:32

So the pressure builds with nowhere to go. You're supposed to know everything, and you can't admit that you don't. And the gap between those two things, that's where the imposter syndrome lives. There's a question hiding in all of this. And it's the one Mary kept circling. When you don't know the answer, and you won't always know the answer, what do you do? Do you fake it? Act two. A second layer. For some of the people we talked to, that fear of being found out, it didn't stop at the work. There was something else underneath it. Let's go back to Julie. When she was up for her director role, she didn't get it. The job went to someone else first.

Julie 7:20

I wasn't the first choice for the director role to start with, and went to my male counterpart, which was fine. But it led to a lot of wait a second. That self-reflection of why did he get chosen over me?

Katey 7:36

She did eventually get the role. The man who got it first was made interim, then moved out of it, then left. And then they needed someone, and there she was. But even now, even with the title, even years in, a question follows her into the room.

Julie 7:56

You know, kind of always in the back of your mind, are they choosing me on merit or are they choosing me because there's a box to check?

Katey 8:03

That question, merit or a box to check, is the second layer. It's not just do I know enough? It's am I even supposed to be here? And it comes with a particular kind of map that our colleagues don't even have to do.

Julie 8:20

It's harder just in IT in general, as a female, to have your voice heard and to be seen and respected as a leader who is not, you know, the emotional whatever that comes with the female stereotype. There's a tightrope in that. Be confident, but not too confident. Having conversations where you sound confident and strategic, but not coming across as bossy.

Katey 8:55

Mary sees this too. They've spent a career as someone who didn't look like the picture in people's heads when they imagined a chief technology officer.

Meri 9:04

There's a huge amount of imposter syndrome, particularly amongst folks who maybe are a little different than the stereotypical uh view of what an IT guy looks like, right? Um, so women, non-binary folks, people of color, anybody who didn't study computer science but still ended up in tech or IT, I think all of those folks have been told that they're not good enough and they're not expected and they're not respected so much that it's really easy to incorporate that into your view of yourself.

Katey 9:38

You're told in a hundred small ways that you're not what this is supposed to look like. And the danger isn't just the telling, it's that you start to believe it. You take the room's doubt and you make it your own. So here's the question that sets up everything that comes next. What if you didn't? What if someone walked into all of this? The same rooms, the same low expectations, the same not looking like the picture, and simply refused to take that doubt inside. Remember that voice from the very beginning? The one who said she never felt like she might be found out? It's time to go back to her.

Producer 10:57

That's the problem HP and SoftChoice set out to solve together. HP's portfolio spans the full technology stack that modern IT leaders are responsible for, from personal systems and workstations to printing, collaboration tools, managed services, and AI-powered workforce software. And SoftChoice brings the implementation expertise and customer delivery capabilities to make sure it all works together seamlessly without disruption to your business. The idea is simple. Instead of stitching together solutions from a dozen different places, you get a unified experience, hardware, software, and services from partners who are accountable for the outcome. To learn more about what HP and SoftChoice can do for your organization, visit softchoice.com/slash HP or click the link in the description.

Katey 11:44

Act 3. The room, not the person.

Rosalind 11:49

My name is Rosalind Picard. I'm a professor at the MIT Media Lab and also an entrepreneur, co-founder of Empatica.

Katey 11:59

Rosalind invented a field of computing and won one of Engineers' top honors, the IEEE Medal for Innovators in Healthcare Technology.

Rosalind 12:09

To me, that medal was something I would read about and see pictures of gray-haired or white-haired guys in suits getting these medals, and they were people who'd been around forever. And so I'd actually never seen a young woman get such an award. So I was just kind of shocked, actually. At first, I thought, is this a scam? A scam.

Katey 12:33

The most prestigious recognition of her career arrives. And the first instinct is that it can't be real. Because she'd never seen someone like her receive it. But notice what that isn't. It isn't self-doubt. She didn't think she hadn't earned it. She thought the world didn't hand these to people who looked like her. And there's a difference. She told us so directly.

Rosalind 12:58

What I hear from a lot of my friends who have it, who are MIT faculty, is that it's more of like a feeling of that they might be discovered as not belonging. And for me, I've never felt that I might be discovered as not belonging. I felt like I belonged, like I could hold my own just fine, technically.

Katey 13:18

So if that doubt wasn't inside her, where was it? Her answer reframes this entire episode.

Rosalind 13:25

For me, the thing I noticed that I thought was sometimes an impediment was that people just felt uncomfortable with me because I looked so different from you know the other 49 guys in the room, right? There might be 50 of us. And they might have just not been used to a woman or somebody who looks like me being there. And I imagine anybody who just looks like an outlier may go through a similar experience.

Katey 13:51

The discomfort was real. It just wasn't hers. It belonged to the room. And she figured out early that her job wasn't to fix herself, it was to get people past their first reaction and onto the substance of her work. There's a story she tells about this. Early in her career at AT ⁇ T Bell Labs, her dream job, she just crashed a compiler and went to find the engineer who built the language so they could debug it together.

Rosalind 14:23

And when I walked in there, he just kind of looked at me and looked sort of scared. Like a person who thought, uh-oh, how do I talk with this woman? And I and I realized as I looked around, everybody on the floor was a guy like in dark pants and a light shirt. So I kind of tried to dress the same, like in dark pants and a light shirt, to kind of not look so different, um, to try to look like I fit in, right? Because what people first see uh is your appearance. And then as I sat next to him, not kind of face threat straight across from him, and we started talking technical through the software, he got much more relaxed and felt, you know, fine. And we had a fabulous conversation and became great colleagues.

Katey 15:05

That was the move. Get past the appearance, get to the substance. But don't mistake her confidence for never having to work at anything. Because there was once one place she absolutely faked it.

Rosalind 15:19

I am familiar with the idea of the fake it till you make it. With technical stuff, I've never had to fake it. One thing that where I did have to kind of fake it till I make it is I had to stand up and give talks and appear like I was owning the room, as the speaker coaches say to do. I'm the girl who flunked show and tell. I was so shy and terrified to be in front of people that I really did not feel at all comfortable up there.

Katey 15:45

So she faked confidence as a speaker, never competence in the work. And that distinction matters because the rooms she walked into kept underestimating the work over and over.

Rosalind 15:58

Consistently I would see low expectations. They think, oh, she's the young female, she won't be as good as these guys. We'll give her the easy project. They never said this, but then they would give me a project that I would finish the first week I was there.

Katey 16:13

Even the people meant to champion her didn't always see it. When she came up for tenure at MIT, the make or break moment of an academic career, a mentor admitted something to her later.

Rosalind 16:25

When I was up for tenure on the faculty at MIT, I was hired at the same time as another guy in the group. And later, a mentor of both of us said to me that he thought that the other guy wound up leaving. I wound up staying and getting tenure. And he said, I thought you would be the one who would not get tenure. I thought you'd be the one who wouldn't make it. And here's how she carried that. I could see signs of that, like, you know, as it was happening. But I was like, eh, you know, I can't control whether this will happen or not. I'm just gonna have fun, do cool work, do my best work, you know, and if it doesn't work out, so be it.

Katey 17:04

But maybe the clearest proof of her whole philosophy is the field she invented. Today, it's called effective computing. Technology that can read signals related to human emotion. It's in your smartwatch. It's in the AI you talk to. But when she started, the engineering world thought the whole idea was a joke.

Rosalind 17:27

The work was rejected from the first conference I sent it to. They said, it doesn't fit and we don't do emotion.

Katey 17:32

It got worse than rejection. At a conference, she overheard one of the leaders in her field talking about her.

Rosalind 17:39

I overheard a guy saying to somebody else, have you heard what she's doing? She used to do respectable work. My heart sank. It was like, oh man, it's exactly what I feared.

Katey 17:52

She used to do respectable work, said out loud in a room where she could hear it. She could have taken that inside. She could have decided that they were right. Instead, she kept building the rigor, the measurement, the engineering. And then years later, at that same conference.

Rosalind 18:13

This leader in the field who before had made that dismissive comment came up to me and he said, Hey, I've started working on affective computing now, and I'm having trouble getting good data. Would you be willing to share your data with me?

Katey 18:27

The man who'd said she'd stop doing respectable work came back to ask for her help. And she gave it. That's the whole arc right there. The room was wrong. The work outlasted the doubt. It just took time. So, what do you do with all this? If you're the one in the chair sweating the meeting, sure you're about to be the one found out. Here's what we heard. From Mary, the most practical advice: you can't think your way out of feeling. You have to chip at it.

Meri 19:07

Do something every single day that helps you feel a little bit more in control, feel a little bit more knowledgeable, learn something new every single day. And over time it all adds up and it helps you to feel more confident.

Katey 19:22

From Julie, permission. Permission to not have it all and to stop performing that you do.

Julie 19:30

I really don't have to have all the answers because someone else in the room is gonna fill in the gaps for me. I'm not the only one who has questions, and it's okay for me to ask when I don't understand. And from Rosalind, patience.

Katey 19:47

And a warning.

Rosalind 19:55

It may take five years. Give it time. There are people who will judge you with all the wrong reasons because they won't bother to even get the whole story. They should really be judged based on their ability to do a great job. Three people.

Katey 20:11

Three different relationships to the same feeling. Julie and Mary have felt the imposter from the inside and made a kind of peace with it. Rosalind never felt it inside at all. She just kept meeting it in other people's faces and decided every time that the discomfort in the room was not a verdict on her. Maybe that's the gift in this. Not that the doubt disappears, that you get to choose where it lives. The catalyst was reported and produced by Tobin Dalrymple and the team at Pilgrim Content. Editing by Ryan Clark with support from Philippe Dimas, Joseph Bayer, and the marketing team at SoftChoice. Special thanks to Julie Sche, Mary Williams, and Rosalind Picard for sharing their stories and their hard-won wisdom.

Producer 21:07

Thanks again to HP and SoftChoice for supporting today's episode. If you're looking for a simpler, more unified approach to devices, printing, and IT services, visit SoftChoice.comslash HP or click the link in the description.