Did I Say That Out Loud?: How My Foot in Mouth Stepped Into Common Ground

Automatic Summary

From Imposter Syndrome to Leadership Triumph: Katie Shy's Journey Through the Tech World

Katie Shy, co-founder and Chief Customer Officer of the SaaS platform, Booster, is a sterling example of a leader who faced her own insecurities and came out victorious. Suffering from imposter syndrome in a tech world primarily dominated by men, she held an important position at IBM, yet felt insecure and overwhelmed. However, a moment of frustration ultimately catalyzed her journey into becoming an exceptional leader.

The Moment That Sparked A Change

Who knew a conference call could be a pivotal point in one's career? Katie vividly recalls her days at IBM when conference calls were the primary mode of communication. It was during one such call that an unintentionally broadcasted outburst of frustration broke the ice, enabling the team to solve a stalled hardware issue in the system.

From the perspective of an account executive, this issue was a grave concern. The internal conflicts in strategy amongst the teams had created quite an impasse. The situation, although awkward, actually served as a catalyst for solving the problem and initiated Katie's journey to becoming a more effective leader.

Break Out of the Shell: The Leadership Formula

If you've ever questioned your leadership ability, Katie's experience can provide some valuable insights. The sudden outburst in that conference call ignited a change not only in the situation but in her approach towards leadership. From this encounter, she devised a leadership formula comprised of three key components.

  1. Addressing everything head-on: Katie emphasizes that avoidance and evasion lead nowhere. Being honest, assessing the situation critically, and facing it bravely - however challenging it might appear - is crucial in leadership.
  2. Making space for emotion: Human emotions inevitably influence project outcomes, and acknowledging their presence can lead to better understanding and cooperation. By asking team members about their feelings towards the project, you'll be creating an environment open to expressing emotions.
  3. Taking responsibility: As a leader, you should be willing to take responsibility for your actions and the outcomes that they produce. Katie advocates taking ownership and responsibility, as evading or shifting blame doesn't solve any issues.

In Katie's own words, "If you take these three principles and apply them to your work, no matter the situation, you will find common ground with everyone who you work with."

The Journey: From Imposter Syndrome to Tech Company Co-Founder

The strong, ambitious, and capable Katie Shy who exists today was once a young rookie, striving to find her footing in a workplace teeming with experienced professionals, mostly men. Her journey is an inspiration for all aspiring leaders battling self-doubt and imposter syndrome in industries dominated by more seasoned professionals. Today, Katie no longer dreads stepping into the role of leader but embraces it with confidence - a major leap from that unsettling conference call 20 years ago.

With dedication, perseverance, and the application of her three-point formula, Katie has indeed emerged as a remarkable leader. This goes to show anyone questioning their abilities: Yes, you can be a leader too. So get out there, and make your mark, just like Katie did.

Video Transcription

I'm Katie Shy. I'm co-founder and Chief customer officer of Booster. We're a SASS platform that's both AC RM and an order management system for media and advertising. And I am going to tell you the exact moment. Uh I learned how to be a leader like the actual formula.And I hope if you're questioning yourself or you're scared or feeling like an impostor that this is gonna help you these 20 minutes 20 years ago in a time before Zoom, there were only conference calls and we had long dial in numbers with passcodes. And if you had a really fancy service, it would announce a recording of your name when you entered into the conference. And 20 years ago, I was an ambitious, bright driven, but very insecure and scared 20 something. I had a degree in art history and primatology, which were super fun in college but kind of useless. And I had a big job at IBM and a huge case of imposter syndrome to go along with it. Everyone I worked with was twice my age. Um They were an engineer or they were bought through an acquisition of a company that they had started, I was surrounded by almost entirely men and it was my job to tell them what to do in order to grow revenue. Um I was an account executive and we had a situation at my client that I was responsible to resolve.

The situation was roughly that we had one group that wanted to sell software and another group that wanted to sell the services that would effectively outsource that software and remove the need to buy it. But in the way of this argument was the fact that we had sold some hardware to the client and it stopped working. So the client had said I'm not doing anything until you fix what we already have. We called this a crit sit, there was a procedure around it and it required that we all met every day. In this case, at 230 in the afternoon, there were like eight of us and we would all get on the phone ostensibly to solve this technical problem. But also to figure out the strategy forward of what we were gonna lead with at the client. There was a lot of competing agendas. Um You've probably been to a meeting like this. It sounded like, um, all, you know, blah, blah, blah like that. Um It sucked. It really, it was horrible. I dreaded it every day. It, we never made any progress. Uh, I felt like such a loser. And, uh, one day I think it was day 10 of this crit it, I was in the office 230 rolls around and it's time to dial in and I'm like, slumped back in my chair, probably like hanging off of it, pick up the phone and put it under my chin.

Kind of stare out the window at like the life that I wish I was having at that moment. And I'm, you know, dialing the numbers, I probably had them memorized at this point. And I say under my breath, um I don't wanna join this fucking call and then I hear this automated voice saying, joining conference, I don't wanna join this fucking call and it was dead silent on the line. But I knew that they were all there because I was definitely late. So I was dragging my feet not wanting to join this call. I was also the only female. So I couldn't even pretend like it was somebody else on the call. It was definitely me. They definitely all heard it. And you know how, when you have like a near death experience, your life flashes before your eyes and, and time slows down. That's what it was like for me, I remember having like an hour to game theory out what the hell I was gonna do in this situation. I thought about just like closing my computer, taking my bag walking calmly out of the building and just like starting a new life. I never worked there that never happened. I never wanted to be in business or tech or computers just get it.

Um, but I couldn't do that because I would have had to walk by like, two or three of the people who were on the call and that seemed worse and, and more mortifying. Um, I thought about hanging up immediately and just maybe joining the call tomorrow and then I'm never talking about it. I thought about gas lighting. I didn't know the term at the time. But being like, what, I didn't hear anything who, who, who, who said that. But all of those seemed like really at some point, I was gonna have to pay the price for this. So I did the only thing that I really could do and I said, um hi, it's Katie and I really hate this call and I've come a long way since then. Um I'm a tech company, co-founder. I run all of product and all of customer success. I work with the greatest clients in the world and some of the most interesting publishers in the world. I lead a lot of people through a lot of situations and I never dread it and I never hold the phone under my chin and curse out my colleagues. And that is because I learned the greatest lessons from drinking that water that I had to wash down that huge foot in my mouth and everything I needed to know was, was in this story. Because by addressing it, we ended up solving the problem.

I'm not gonna lie and say like five minutes later, everything was perfect. I honestly can't remember if it was five minutes or five days. But by breaking up, uh the block that we had on that call, uh we were able to find a solution. So if you've ever asked yourself, you know, how can I be a leader? Am I allowed? Am I good enough? The answer is yes. And I wanna give you the formula for how to do it. I really believe that if you do these three things, you're magically a leader, the first is address everything head on. Um I don't mean be rude and blunt like me, that was awful. Never ever do that again. But um I mean, assess the situation, the problem, the objective, the constraints and lay it out honestly and completely. Absolutely. No avoidance, no tap dancing. This will sound like uh these kind of phrases uh like if you're building a, a product, hey, these are the problems that we're solving. Here's what we're up against. Uh This isn't working a piece of the data doesn't fit the model. We have a dilemma. Uh And these are the two things that are in conflict.

These are the, the the kinds of phrases that you can use to effectively address things head on if I had simply said back in that critical situation, hey, um I believe the best path for the client is gonna be XYZ. But I'm hesitating because I know everyone on the team has more experience in this situation than I do. What do you guys think I would have addressed every single block that we were experiencing without having to humiliate myself? The next one and I can't stress this enough is make space for emotion. If you feel a certain way, you aren't alone, there's just no way you're feeling something and everyone else is on a different planet. I mean, why would you be the only one who is worried or stressed about something or even the only one with impostor syndrome, like it's pretty well documented. We are all wondering what we're doing here and if it's OK and everyone says it's just business um and then treats people however they want and then pretends like we're robots, but we're really not. And um I think the assumption there is that emotions have to be bad, but they can also be good, right? They uh they can be things like passion and excitement which are good or they can be harder ones like fear and frustration.

But I think the fact of the matter and addressing the fact of the matter head on is that emotions will shape the outcomes of our projects. So we need to factor them in as an input. So my advice is ask as part of your stand up every day, if you're having a stand up meeting or weekly whenever it is as part of the project status, how are you feeling about this project? Ask everybody what they say. Um This is in a therapy session so I don't have any tips for what to deal with those motions. I just think asking and making space for them is good enough or good enough start if I had shared my feelings of frustration and dis discomfort way back. I don't know. On day two of our problem, I would have learned that we all had one thing in common and we could have solved the problem from there, which was how we felt about the situation, which is none of us wanted to be there. But instead, I focused on all the things that I wasn't, I wasn't smart enough. I wasn't technical enough. I wasn't experienced enough. I wasn't older. I wasn't a man. Um And I missed the thing that we all had in common and that myth not addressing everyone's emotions and my own cost us a lot of time and frustration.

The last one is take responsibility, take responsibility for your mistakes for the results, whether they're good or bad for other people, but for mostly what you own, which is more likely you own more than you think you do. Um In this situation here, I was waiting for the experts to solve this situation when honestly it was my account and it was my problem to solve. And by looking around at everybody else. I was just delaying and creating more frustration. I wasted so much time hiding from my responsibility. If you take these three principles and apply them to your work, no matter the situation, you will find common ground with everyone who you work with. And I truly believe that if you can do that, you will emerge as a leader. Good luck.