EP #3: How to Be an Authentic Leader in Tech With Tutti Taygerly

Tutti Taygerly - executive coach

We're so proud to announce the third guest of the StackPod: Tutti Taygerly! With more than 20 years of design experience in different types of companies - ranging from (tech) giants such as Facebook and Disney to smaller design agencies - she gained a ton of experience as a female design specialist in tech.

Using all lessons Tutti learned along the way, she now helps women ánd men to be the leader in tech they want to be, by, basically, being true to themselves. In this episode, Anthony talks to Tutti about her journey, she shares concrete tips to stay authentic ánd she spills the details about her new book that just came out.

You can find a written transcript of the episode below. Enjoy the recording!

Episode transcript

Tutti: [00:00] Pre this influx of venture capital there was a baseline of hey, this is why we were here. It was fun. It was playful. It was product-focused, maybe customer-focused. And hey, maybe there's a little bit of a switch now for having to move at a different pace. 

Annerieke: [00:20] Hey there, and welcome to the StackPod. This is a podcast where we talk about all things related to observability, because that's what we do and that's what we're passionate about, but also what it's like to work in a tech company. So if you are interested in that, you are definitely in the right place.

Annerieke: [00:35] In this episode, Anthony talks to Tutti Taygerly. Tutti is an exective and leadership coach with more than 20 years of design experience at large companies, design agencies and startups in Silicon Valley, including Disney and Facebook. She now helps women and men to be the leader they want to be in tech by, basically, being yourself. Also, she’s a fanatic surfer, and you’ll hear why surfing is actually a great metaphor for being a true leader. Enjoy the podcast. 

Anthony: [01:09] Hey everybody. Today, I'm joined by Tutti Taygerly, who's taken time out of her busy schedule to join us today and share some of her inspiration, her story, her roadmap in tech, if you will, as part of our ongoing series whereby we interview people in and around the technology industry. But that's enough for me talking. Tutti, would you like to introduce yourself and give a brief intro for everybody else around, who you are and what you do?

Tutti: [01:43] That'd be wonderful. Thank you for having me on, Anthony. So I've had a 22 year career in tech as a design leader, worked for design firms, early stage startups and also large tech companies. My last corporate job was at Facebook leading teams that did ad products, as well as more zero to one Greenfield video products. And all of that was amazing, because I've been a designer my entire life and loved the culture and processes and inspiring, getting teams together. But I ended up stepping away from the corporate life about two or three years ago on the aftermath of really three big events in my life. You can call it a midlife crisis or what you would like. And I think after those events I was really questioning if I still wanted to do the hustle and grind of these long hours and super high expectations and conditions in corporate life.

Tutti: [02:47] So I ended up leaving to start my own company. And now I'm a leadership coach. I think what you see is really interesting because we grow up with certain expectations and certain understandings from our parents, and I think we're shaped by the culture of the companies, the tech industry that we live in. I did a lot of computer science at Stanford University, where I got my undergrad, before I shifted more into human computer interaction. And so often I would be one of the handful of women in a room full of guys. And that happened through the majority of my tech career. So I really learned to tough it up, put on the armor, really act, especially in my first jobs, really in this command and control style of leadership where when you're first promoted, when you're first managing a team, you're like, "Oh, I need to know what I'm doing. I need to tell everyone what to do. That's what they're looking to me for."

Tutti: [03:46] And in some of those roles, I was a creative director, really advising the world's top brands with the future of mobile living, connected TVs, smart homes, what all of those are like. And there was the feeling of, as you call it, this masculine sense, a little bit of a masculine sense of power of having to just know what you're doing, suck it up, suppress the emotions and just no nonsense, go, go, go and grind it out. Honestly, I have to say, I feel very supported and blessed during my time at Facebook to have had models of leaders, and not that Facebook is a model for everything but in terms of professional growth and development, having communities, mentors, supports and coaches who would remind me that hey, it's okay to take some time off. It's okay to be vulnerable. It's okay to share what you're going through with your teams.

Tutti: [04:44] And so while you would imagine those events would really toughen me up, I think it was a little bit of a catharsis knowing that oh my gosh, this is so tough. I'm proverbially at rock bottom, I'd say the worst year of my life and it's okay to be able to lead and show that vulnerability.

Anthony: [05:04] That's a really good attitude to have, because a lot of people would have a defeatist attitude in some cases and...

Tutti: [05:14] I mean, Anthony don't get me wrong, there were some terribly... I'm not painting this rosy tinted thing. It's so much easier a couple years later to see it, but when you're in the midst of it, it's so hard.

Anthony: [05:28] I found one of the biggest lessons in my career was to be vulnerable, but then distance your decision-making from the emotional side of things. I find often when you make a decision around an email and you're sending an email to maybe your boss or a customer or something, if you're emotionally connected to that email, nine times out of 10 it's a bad email and won't help your career. So being able to learn to distinguish between is my output being affected by my vulnerability and my emotions versus am I just being a human being and sharing things with other people, which is much healthier than allowing it to affect your output, especially in a career, right?

Tutti: [06:21] Absolutely. And I think there's also a difference between the negative emotion. So sending that email with resentment, anger, frustration, definitely pause and wait an overnight or something. But I think it can be really different if you are going through more emotions of appreciation, energy, joy, I think it's important to distinguish between them, be like, "How do you want the recipient of this email to be feeling? Do you want them to feel the inspiration and curiosity?" Sure. Why not? But definitely not the rage and resentment.

Anthony: [06:55] We actually didn't know each other before this podcast. I actually got to know you through a news article that I read on Insider, you were featured, and your career at Facebook was obviously the poster child kind of thing. But then it's how you left Facebook and then you moved into coaching and now that's your full-time job. And obviously that was all part of that catharsis movement that you said where you took everything that you've learned, appreciated it, and now you help other people. Could you give us a little bit more detail around what you currently do today in terms of your coaching and some of the stories around that?

Tutti: [07:36] Absolutely. Because I spent so long in tech, I understand this world. So what I do now is I help support leaders in tech, both directors, VPs, senior VPs in these large corporations like the ones that I used to work at, who are dealing with what's my authentic leadership. If I'm a quiet leader, how do I make sure that I can speak up and I'm heard? How do I make sure that I am empathetic and compassionate to my team while also making sure that I get results? Working with people through those types of challenges. And then I also work a lot with CEOs and startup co-founders. And for them, different challenges, a lot of co-founder relationships, how do we equitably split our cap table and roles and responsibilities, especially when things change so rapidly every quarter or every month?

Tutti: [08:29] And so many first time founders, especially once they've hit a couple of funding rounds, are trying to figure out how to scale and amplify their reach, and when their companies get a little bigger, how to establish the right processes and cultures so that their companies continue to thrive, both based on the product market fit, hitting the numbers, hitting all your OKRs, but also making sure that people thrive and the culture thrives and there's creativity so that people can do their best work.

Anthony: [09:00] There's a difference between working hard and working smart. In my previous jobs I've worked for, let's say, quote, tyrannical CEOs who are like, "Hey, I've gotten 100 million in series B or series C funding, this idea has venture capital money invested in it. We have to show progress to the board every month or whatever. Do it my way or the highway." Or if you do it wrong, you're obviously doing it the wrong way and you end up having to work long hours just to do things that other people want you to do. And you end up just being more of a workhorse, as opposed to actually somebody who feels like they're giving to the success of the company, more than just taking absolutely a paycheck and a stock option.

Anthony: [09:50] What would be your advice to people who are going through that early rounds of funding when they all of a sudden have to switch? Especially series B and series C, where they have to switch from being maybe a fund startup with a decent product and a few decent customers to then having to get critical mass within the space of six to 12 months.

Tutti: [10:12] There was a different baseline. Pre this influx of venture capital there was a baseline of ‘hey, this is why we were here’. It was fun. It was playful. It was product focused, maybe customer focus. And hey, maybe there's a little bit of a switch now for having to move at a different pace, account to different stakeholders and really hit all of these goals. I really love your contrast between the first and the second, because so many times we think in black or white, that time was so great when we were all playful and we were a small team and we just did it for the joy of the work and the oh shit, now it's post-series B, post-series C, we're a serious company. How do we grow in scale? Because I think neither is completely true. And of course, we'll put to the side tyrannical boss for a minute, because there's definitely situations and times where for your energy, for your health, it is not the time to stay.

Tutti: [11:14] And if that's financially possible, then there is a time where hey, it's the end of the rope and you can't stay in these conditions. And I completely understand that. However, before you get there, there might be a period of where you remember what brought you to this company, whether it was the love of the product, whether it was getting and doing some of this stuff at Global Impact, whether it was the coworkers or maybe it was the same CEO who, yes, could be tyrannical, but at certain points was really inspired with the vision of what they were going to be able to do for the world and you were going to be a part of it. So some of the advice that I would give would be really remember why you joined that company, and is it possible to add that sense of curiosity and play and inquiry back into your current work?

Tutti: [12:02] I love, Anthony, you were talking about how it is to work smarter, not harder, and one of the parts I think about working smarter is knowing when you're in this state of flow and creativity, what gives you that energy and to try and do more of that, because for some people it's the coworkers, for some people it's the product, for some, engineers or different makers, it's the heads down focused maker time. So it really helps to focus on what was it that brought you there. And then the second thing is really, this is the thing that's forgotten so much in the grind time, is the relationships. Because I know so many people who say, "I don't have time for that. I don't have time to chit chat for two or three minutes. We need to get down to the nuts and bolts of it." But the reality is both are needed and I believe you do better work when you have that trust in relationships with your colleagues.

Anthony: [12:55] So I'm a big believer in the social aspects of work as well. And this may be just the British culture coming out in me as well but you always do the happy hour drinks. And not that I'm condoning alcoholism in any way, shape or form, but when you do actually go out and you meet with people, especially when you go out and you have a drink and you get to know them in a social setting, you get to know a little bit more about their vulnerabilities.

Anthony: [13:24] Even if you find out that they're a lightweight and they can only handle two beers, you now know that about them. It's a weird thing. It's always been that way that if I can go out and have a few drinks with people, all of a sudden the next day it's like you you've been friends for years and you just get to know each other, and then in turn you work better together and you'll have more time for each other and you create a bit more of a culture. Now, one of the biggest mistakes I did make is that I thought for the longest time that I could just introduce that social culture.

Anthony: [14:07] So I would just completely ignore the company's culture and I would look at the technology and I'd be like, "Oh, well there's only 50 people there. So if I come in, maybe I can introduce this and everybody's going to enjoy it." That doesn't work. If the CEO just doesn't like the sight of his employees with a drink in their hand and instantly reprimands them, it's never going to work because he's or she is ultimately in charge of the culture. It has to come from the top down in terms of how everything rolls. You can have your pockets, but when the company's so small, like 50 people, you're so close to the senior leadership, you need at least several people to build a culture. I like to have jokes. I don't take any meeting too seriously.

Anthony: [14:57] Even if we're dealing with an outage or whatever, I'll join the meeting, I'll be like, "Oh, what did you touch now?" Kind of thing. Because at the end of the day, actually one of my managers said one of the best things to me, he said, "Don't stress out, it's only software." And when you take that into consideration, it's like, "Okay, Facebook goes down, there's huge impacts, whatever." But at the end of the day, nobody died as a result of Facebook going down.

Tutti: [15:26] Yep. No babies will die. It's okay.

Anthony: Exactly.

Tutti: Only software.

Anthony: [15:32] So you need to bring that back into your mind. Let's talk a little bit more about you actually. So we've talked a lot about leadership. We've talked a lot about what you do. You help coach people. You've shared some opinions, and thank you for doing that by the way. I know this can be a little bit all over the place in terms of a casual interview.

Tutti: That's the fun of a podcast.

Anthony: [16:00] I'm really happy that you've been a good sport about everything. I did also read that you've lived in seven countries across three different continents. Where have you lived throughout your life? What's the backstory behind that?

Tutti: [16:13] Well, I was actually going to say that I've lived in Amsterdam before. And I don't recall much about it because I went to preschool and kindergarten there. So I'm Thai. I may sound like a Californian, but I am native Thai, was born in Singapore, and my father works for Thai Airways, the airline. And every three or four years, we would move to a different country. He was their growth guy, if you will. 

Tutti: [16:41] So every time Thai Airways wanted to test out a new route at a new city, they would send him out as the station manager on the ground to establish the base of operations and see hey, is this a feasible route for the airline? So he'd be there for a couple years. Some routes work, some routes didn't, but that was his job, that we followed him around. So I was educated in an international school system and I loved it. I loved the adventure and the moving around.

Anthony: [17:06] That's cool. I really like Thailand. I spent a little bit of time there. I also spent a little bit of time in Singapore. I spent a lot of time working for software companies, but for financial services customers there's their technical account manager. I was very fortunate to be able to stay in the Marina Base Sands in Singapore.

Tutti: Beautiful.

Anthony: [17:31] ... The infinity port. I loved that. If it wasn't for the sin taxes and the fact that you can't open soda on a public place or chew gum, I'd consider living there. But I'm a little bit of a rebel at heart. And I could see myself getting into quite significant trouble in a very short amount of time if I had to live with that kind of control.

Tutti: [17:54] Oh, definitely. I went through the Singapore airport this summer on the way to Thailand to visit my mom, and I was traveling with my two girls, and they take COVID very, very seriously. You're in a quarantined area of the airport. And my two daughters are looking at an iPad. They're watching a video together. So their heads are bent together. And this woman from in Singapore, marches over with a sign that... I have trouble with feet and meters, but the distance is roughly six feet, so I don't know if it's a meter or one and a half meters, and she puts the sign between them and says, "Further apart, you need to be this far apart." And I'm like, "They live together. We live together." And she's like, "Get apart." And she has this sign with the measurement and it was hilarious. We're like, "Okay, okay, we'll do that."

Anthony: [18:43] It reminds me of LA actually. I was in LA two weeks ago. And so in New York now, even though everything was locked down, we actually haven't lost a ton of restaurants and bars because they did this really cool thing where they basically said, "Okay, every restaurant, if you've got a parking spot out the front of your restaurant, you can take it over as outdoor seating." And they haven't taken them away. So now you've got all this outdoor seating area. And so in 15 years or something, somebody's going to go, "Oh, why do New Yorkers sit outside?" And I'll be like, "Well, let me tell you about the great COVID of 2020."

Tutti: [19:29] Ah, I love it.

Anthony: [19:32] But in LA, so now if you've got a COVID vaccine, you don't need to wear a mask, you can go in anywhere. You don't even really have to show proof of vaccination. It's just usually a de facto thing. They're like, "Oh, you're vaccinated."

Tutti: [19:45] You do in San Francisco. They check ID. They check everything. Different cities.

Anthony: [19:49] Well, this is my thing with LA, I had to go to the restaurant, I would be walking outside, I would get the evil looks from people because I wasn't wearing a mask on the street and I'd get even people doing this. And I'm like, "Okay, I'm on the street though. We're all breathing the same air." And then I'd get to the restaurant, they'd make me put it on, which I get, is fine. Then they'd make me show my proof of vaccination, make me show my ID and then they wouldn't let me take off the mask until I literally had a beverage or a piece of food in front of me. It was like going on an airplane. I was like, "Man, this is a little bit over the top because if I had COVID, the minute I take it off and I'm sneezing and I'm coughing, everybody's going to get infected. Because it only helps keep my stuff away from other people. You could still breathe in COVID if it's in the air, even if you've got a mask on." Again, I don't like dealing with people police.

Tutti: [20:56] I think what's fascinating about that story, and maybe similar to different companies and cultures, is that you walk into different places and there's maybe science and data, but there's though the cultural norms. And back to what you were saying, no matter how much a CEO may try and say, "This is the way things are at the company," cultural norms develop. They develop from the people. They develop from the practices and ways of doing things. I think up until about 50, 75, it might the personality and values of the CEO and the co-founders because they've hired all the people and often it's people who believe the same things as them, but then it grows and adapts and just takes off like wildfire. And sometimes it's hard to look back and be like, "Why did all these things develop? How did this happen?" Sometimes all you can do is laugh, as you were saying earlier, shifts the mood and the levity of it.

Anthony: [21:55] That's very true. So, for people who don't know you and whatever, they'll be like, "Oh, this person's a career coach and she talks a big game," but I do want to highlight the fact that you do have a book coming out as well. So it's not just me getting you on and looking at Insider and you talking a big game, you are actually having a book published. Would you like to give us a little bit of an overview as to what the book is about and when it's coming out?

Tutti: [22:30] Sure thing. My book is called Make Space to Lead and it'll be out, I think, by the time this podcast airs. And what it shares is what I've learned through my own experiences in Silicon Valley, as well as working with these startup CEOs and executives in tech, it really balances out the fact that we are doers all the time. We got to hit these milestones. We've got to hit these OKRs. We've got to hit these scaling numbers to justify our series B, series C round investments and keep running all the time. However, to balance out this, work harder, grind it out, sometimes you lose something. You lose your sanity, your peace, your creativity, the way you lead and work really well. So Make Space to Lead talks about different techniques, similar to some of the ones we've talked about here. How if you slow down, if you rest, not all the time, but know the right context for it.

Tutti: [23:30] If you do this work smarter, if you create that space to be your authentic leader, to address the self critical voices, it takes some time to be, go out for the drink, make a joke, get to know people and build these relationships. It's balancing out that being as well as that doing that's going to get you success and what really matters in a professional life as well as a personal life. And I use a surfing metaphor a lot through it as well, because most people think of surfing, especially recently of people have watched it last summer in the Olympics, as just this really strong, powerful, typically a male up and riding on the wave and on the board and really going down the line, but the reality is if you go out surfing and if you go out for maybe an hour or two hour session, you might be up and doing that riding of the wave for maybe 10, 20 seconds.

Tutti: [24:30] The rest of the time is bobbing on the ocean, experiencing nature, doing a lot of paddling, so a lot of the grind and paddling and putting in the effort, but also scanning the horizon and waiting to see where is the next wave, where's the next opportunity. And what I love about that is it's a metaphor, that there's the times where you need to do, do, do, to paddle, to ride the wave, but there's also times where you simply need to be and let the inspiration, the insights, the creativity, and the flow come, because that's going to make you a better leader overall.

Anthony: [25:05] I wonder if that you relate to this with surfing a little bit. So obviously I don't surf in New York City, but...

Tutti: [25:17] Rockaway Beach, not too far away.

Anthony: [25:20] I know, but I actually like to fly. I've never had a driver's license. I've actually spent more time flying planes than I have driving cars.

Tutti: Amazing.

Anthony: [25:33] So I love to fly. I've done barrel rolls and all that kind of stuff, but I just love the skill of landing an aircraft, navigating through a terrain, using your eyes to figure out where the runway is, figuring out winds, figuring out thrust, figuring out flaps. And so obviously I don't get a lot of time to fly planes either in New York City, but I do have flight simulators set up and usually when I'm in a rut or I'm not in a creative space, what I'll usually do is I'll sign off and I'll go and land an aircraft because it has a real weather simulator thing. So I can look for an airport where the weather conditions are absolutely abysmal. Like when the hurricane hit Long Island earlier this year, I literally went on flight simulator, turned on real weather and flew into the eye of the hurricane and tried to land at an airport near the eye of the hurricane somewhere in Nassau County, Long Island.

Anthony: [26:42] But that's my thing. And then once I've concentrated on that, because when you're flying, you have a lot of time where you're just flying. It's not until that final 15 to 30 to 45 seconds when you're actually coming down that you need to be laser focused on everything, but then as you're just putting everything together and you're getting into a spot, you're thinking, and because you're not demanding yourself to think it just naturally comes to you. Do you know what I mean?

Tutti: [27:17] Yeah.

Anthony: [27:18] And so I'm wondering if there's a similar thing, based on what you're saying, with the surfing? Because you spend a lot of time just being there, waiting for the wave, you're waiting for something, but then it gives you a lot of time to think at the same time.

Tutti : [27:32] Absolutely. I think that's a perfect analogy. And two things. One, I love that that is something, from seeing you talk about it, that energizes you and that excites you and that gives you a different passion and creativity that I'm sure carries back into your work. And one of the concepts that I talk about in the book is this concept of force and flow. And people might think that force, oh, that's a really masculine word, that's really hard, that's controlling, but we need structures in our life. And the force in it is the dedication of waking up and meditating every day or going to gym every day or putting in the hours at the flight simulator or putting in the hours to swim and build up your body. That's the force and the structures in your life. And then there's going to be times where there's flow, where all of those hours and dedication that you put in comes into this 10, 15 seconds of landing where you snap into this energetic mode and you can just flow, time will fly in different ways and you will just go through this.

Tutti: [28:37] I think all of us have felt of this flow of being in the zone. And some of the magic is realizing that there's going to be times in your life where you're going to be in the force and the effort of it and the rigor and the rhythm of it. And other times it's going to be flow. Either are fine, as long as the energy still keeps coming and, as you said, the positivity, as long as it still feels good, it doesn't feel like a grind, then these are all times to keep going and practicing and keep practice these skills.

Anthony: [29:05] That's really cool. And I'm glad you left us with that thought process. I hope people do go out and read your book. Again, I'm super thankful for you taking the time out of your busy schedule to come and do this.

Tutti: [29:25] Thank you, Anthony, for inviting me.

Annerieke: [29:28] Thank you so much for listening. If you'd like more information about Tutti, her new book and coaching options, go to tuttitaygerly.com. Or, if you want more information about StackState, you can visit stackstate.com. You can also find written transcript of this episode on our website. So.. well that’s it. Make sure to subscribe if you'd like to receive a notification when we launch our next episode and, until next time.

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About Tutti

Tutti Taygerly is an executive leadership coach and professional speaker. She supports CEOs and tech leaders to embrace their unique leadership style to achieve professional impact. She works closely with women, people of color, and immigrants and has a particular love for "difficult" people. Previously she was a design leader at design firms, startups, and large companies including Disney and Facebook. She has written for Business Insider and Fast Company and her new book Make Space to Lead shows high achievers how to reframe our relationship to work.

Tutti grew up in seven countries on three continents and is settled in San Francisco as her home base. She spends her time parenting two spirited girls, obsessively reading, and paddling out for the next wave. Find her at tuttitaygerly.com.

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