Quietly Judging with Amy Lewis - CTO Advisor 091

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All right. I promise you, me and Mark have been recording podcasts. We have like six or seven podcasts in the can, so to speak, but I just haven't had the time to edit them. This is a podcast we recorded a few weeks ago with Amy Lewis. As you guys know, I started a new job at VMware and I've just been just overwhelmed, wrapping down or winding down some of the bigger CTO advisor opportunities. I'll scale back on CTO advisor and spend most of my focus on VMware.

So the second thing I really want to get in as a preamble to this podcast is that this recording is meant to jumpstart a second podcast. This is not just the CTO advisor podcast, but a virtualized geek podcast in which we're focusing on careers. We're going to talk to Amy Lewis about her transformation. I guess you can call it a digital transformation from publishing into enterprise. , how did she identify that she needed to make a change and how did she go about making that change?

So we have Amy Lewis on and Amy, I've been meaning to ask you or your cohort this in person. And when I when I say your call cohort, you're going to know exactly what I'm talking about. How do you quietly judge if you're actively talking about it on Twitter? Like, how does that work? How do you judge why you're like literally talking about it on Twitter? I appreciate that most subtle shout out to my my comrade in arms, Lauren Malhoit.

We've taken up quietly judging as a career, you know, quite a while back. I think I would liken it to an iceberg. You know how they say you can only see like 10 percent of it. Right. It's like that. So you're hearing 10 percent of our out loud voices. And we've said so when we're when we're ready to exit in a blaze of glory, we're going to start the quietly judging show, which will basically be us watching people's videos or slideshows.

And it'll just be the back of our heads like mystery science theater. Yeah. So we know we'll be fired and run out of town on a rail. But say 10, 20 years from now, when we're ready to take up gardening or something else, we're going to look for the quietly judging show. Yeah. I'm actually quite looking forward to that. I'm ready to go. I'm ready to check to see if the Twitter handles there already. So we can go grab that real quick just to watch you quietly judge people.

It could be anonymous if it's just the back of your head. I'm just saying. Well, I think between the two of us. Well, I don't know. When we're together, people seem to realize that what we're doing. But it started years ago, probably like at a Cisco Live. And we just muttered something to each other, kind of lean forward and muttered something. And then we seem to get our picture taken like that all the time. And truthfully, we are quietly judging everybody.

So it was true. Yeah. So I like the fact that you spoke about the Cisco days. It's ironic that both you and Lauren have been at Cisco all about at different times. Yeah. As I look at both you and Lauren's career, this is one of the reasons why we want to you know, we're we're always listening to you about career advice. But and you're talking to other people like that. We like to, you know, kind of poke and prod at your career.

But you've transformed your career over the past few years. A lot, several times, I feel like at least three solid times that I can think of maybe. Yeah, I think part of it is saying yes. And that sort of improvisational opportunity when it presents itself and it feels right to take a leap and try. I think it may speak to just how I walk through life of I really do like to try new things. That pioneer spirit, whatever, however you want to phrase it.

But I've been very fortunate to have people walk with me through this journey. And lately, a lot of my focus has been on team building and and continuing to help other people build their careers, which I really do enjoy. So I sort of joke that there's the public comms ninja who, you know, quietly judges in public and and is on podcasts and does the individual contributor thing. And then there's this other side that's had an opportunity to grow over the past couple of years of director Amy.

Right. And that's that's like team mom. It's a whole different, you know, doing spreadsheets and budgets and working through assignments and coaching people in their career and untangling knots. And I'm like, I always tell my teams, I'm the one on your very worst day at work. I will be there with you on your side of the table like I don't interfere much. But on your very worst day, I'm I'm there. I'm the one you're going to want and I'm going to be sitting on your side of the table.

So one of the things that I've noticed throughout the many podcasts you've been on as we look to diversify our guest list, you did a great job at on the cloud cast a few weeks ago, talking through kind of diversity and all that good stuff. I think looking back at your career, you're you're kind of the poster child, not just for women in tech, but for women who want to break into tech. What I haven't heard from you is kind of your origin story.

I know you were in publishing, but how did you move from publishing to information technology? Like as Matt Broberg would say, what the hell? And it says that to me an awful lot somehow. The by the way, like how much do I love technology? Matt, Matt's dog and my dog had a play date over FaceTime a few weeks ago. Quietly judging, quietly. That's the story for you. Yeah, exactly. You should. You should. But we laughed out uproariously.

Yeah. So I was in publishing for the first half of my career and things that are things that are connected to my career. I realized I've almost always been a remote employee. I lived in New York for a little while and then I moved back to North Carolina, my home base, and worked remotely to a job there. So that part, at least, I'm really familiar with. And after I had my kids, I was sort of at a break point because I had accomplished kind of all that I could in that particular role.

And I knew that I had two kids and that's what I wanted to have. So pregnancy and again, speaking very bluntly for any woman, that's a big sticking factor. If you're going to change careers or jobs or anything, you want to know where you are and your fertility, which seems nuts in this modern day. But it's true. Right. So I had kids. I knew that was all the kids I was going to have. And I was ready to kind of try something new.

And I actually went to a job counselor. And that might be why I'm so into trying to get people matched up with their next career. So I went to this job counselor. I took a whole battery of tests. I spent a good deal of money at the time because I was in publishing and young and stupid. But money completely well worth the spending. So I took the classic test, the Myers-Briggs. But I took this other test that basically said, do you like A or B?

Do you like A or B? And it made you compare every single possible factor about a job to see what you'd like. Most people think they're going to say money or power or, you know, I don't know, something like that. But the most important thing to me was the ability to make my own choices. And the unbelievable counselor who worked with me waved his hands over the tea leaves of all this information he got and said, you need to look for a job at Cisco.

And he goes, I'm not usually so prescriptive. He said, but here's the thing. It's a big company. You can try new things. You're an English major. You're an editor. You understand content. Technical people don't always have that set of skills. So you can learn the other part, but you can bring them something. I never would have had the guts. I wouldn't have even known how to start. I wouldn't have known where to look. I probably thought Cisco was a food company still at the time.

I didn't. I didn't know. And that's what it did. It like he was so sure of himself. He was so completely sure. And it was so random. It was like going to see a psychic and having them tell you something and you just do it because it's so insane. Why not? And it worked. I got a content oriented job at Cisco and I was my I was a contractor and that was my my way in. Wow.

So, Mark. Yeah, I don't know what to say next. Actually, I mean, there's I have one other I have one other kind of great part of the story because the so, of course, contracting is a great way to get into any of these big tech companies. But then they sort of hold that golden prize in front of you of like full badge, full badge. And I worked for a friend of mine now who was an also a mentor and we had a QBR and these were a big deal in the group we were working in.

People prepare and Cisco does the classic or this group did the green, yellow, red. Like, how's your business doing? And I had inherited a business that had so much potential, but there were some issues. Everybody else got up and did their QBR and everything was green. Even if it wasn't, they all were committed to saying green. I got up and I had one green thing and like all red. I'm like, nope, we're in trouble. Pretty much. We need to fix this or kill it because this isn't working.

And jaws drop on the floor. And that is how I got the full badge at Cisco because I risked my own job, but I said the truth. So I always tell people that story as well. Just it doesn't always work out, but somebody in the room is going to respect the guts of saying this is terrible. Let's do something about it. I think that's actually a great to two lessons there. One, always be driving to find out what you want to do in your career.

I think so many people, you know, as they grow up, especially, you know, we grow up and we want to be firefighters or baseball players or basketball players. You know, that's not the reality for some of us. So we tend to we tend to settle. Right. We get a job somewhere because it's there. You know, we pick a desk at there because it's there rather than owning our own career. I think that's something all of us probably need to work on, especially early in our career.

Well, but, you know, take me, for example, I'm I was somewhat mid career and you can you can take the leap. And I think I think you're right. Don't settle. Happiness is incredibly important. Happy employees as a manager. Now, I often say the job description isn't worth anything. You have to hire the right people and then figure out what makes them the happiest. And that's where they'll do the best work. And if they're not mapped to that, find the work that needs to get done somewhere else or figure it out together.

But it really is an important factor. And not because I'm I'm trying to be, you know, one of those whiny entitled types. I just think you can we can all get through and do the thing that's unpleasant with work. There's always something you don't want to do. It's like eating your Brussels sprouts or cleaning up your room. Right. There's something that's on your nerves. But but if 80 percent, 60 percent, even 70 percent is truly what fires your passion.

And for me, it's being able to to make my own decisions, being able to have some freedom to choose. And in every role, that's that's been the that's been the deciding factor. So, Amy, let's follow that theme. You know, we're talking about transformations and pivot points in your career. I mean, you made this amazing jump from publishing to Cisco and not just from, you know, publishing to Cisco. You were a contractor and you finally got a full full badge Cisco by all intents.

If you look from the outside, you know, especially if you measure it by the publishing industry, it's a great company. Like it's one of those things like you go from being a journalist to having a full time job in communications. You were going to be with the newspaper you're with forever. Publishers really don't jump as far as I know. Don't jump shift often. That's really true. Yeah. What brought about because that's part of your culture, half your career to this point.

But most of your career to this point was in publishing. It's very steady organization industry. What made you kind of go outside the box again and make that next career move? I think the other piece of it. So I was very traditional and you're right. Publishing is one of those jobs that if you're lucky enough to get a job in the industry, you hold on to it with two hands. Right. It is people. It's very steady. It's very it's got a lot of interesting people.

There's a lot to hold you to it. It's got a culture. I was in online marketing within publishing. So I started out doing the traditional thing. But even then I couldn't sit still. Right. I read manuscript scripts. I made a living proofreading and editing using my hardcore English skills and background. And then one day somebody's laptop was broken and I looked at it. And then one day nobody was had the nerve to reboot the server. I remember it was a dull server and the server closet of the one person.

I was the IT department. And like I'm the only idiot that would get in there and push the button. It was not even that hard. I was being coached. I think this was always in my blood because the other sort of part of the story. I was one of those, you know, when I was young, I wanted a Commodore 64 more than anything. And my parents thought it was going to rot my brain. So they only gave me two games and a book for how to program.

So I taught myself basic because you can only play the two games so much before it really will rot your brain. And I met. But I set all that aside. I was a chemistry major before I was an English major. And I kind of pushed all that aside, went another direction. But it has a key. It kept calling me. It kept calling me back. I like to know how things work. I like to be in something that changes.

And so technology, it was always there calling out. But I couldn't see the whole picture. So let's talk to us about kind of that. I guess that unknown when I when I look at something like a career move, if I don't have someone to talk to and bounce things off. Wow. Yeah. You know, you you're obviously a self-starter. But there was a bunch of unknowns for this new industry. The technology is one thing like we talked before the podcast in basketball.

You can teach someone the skill, but you can't get somebody to be tall. Yeah, I train tall. Well, I think you can't train having the guts to leap. Right. To decide that this isn't what I want anymore. I want to make that drastic, potentially risky pivot with your career, your your livelihood, right, your mortgage, so to speak. You can't teach guts. You either you're either going to do it or you're not. You can try really hard. Right.

You can push yourself outside of the limits and you can do better. But you can't teach that. You just have to you have to want it. And it's a great question. It's funny when I look back. Like I talked to obviously all my friends worked in publishing then or not. Obviously, I didn't have friends in technology. So people kind of built me up and said, I think you can do this. You know, I had the counselor, but I really didn't have anybody.

And I didn't I've never thought about this till you guys just ask that question. It was absolutely a blind leap of faith. The other the other story I'm on record is telling this one. But the other the other person who kind of brought me through this was Brian Grace Lee. Sometimes you just get lucky and your cube happens to be a few doors down from from Brian Grace Lee. Right. Somebody who knows the industry is incredibly innovative, is open to introducing people into it.

He's he's it's that Detroit upbringing, right. Of like, make it or don't make it. You know, he's a he's an athlete himself, like all those sort of metaphors we talk about. So he he knew he couldn't. He knew he could coach me in some things and some things I couldn't. But he just laid out opportunity in front of me. And and some of it because I pursued it. I I just felt like I want to know what this guy's doing.

He's doing interesting things. My mentor said you should talk to him. And I really pursued it. Probably I won't say stock. That's too strong. But for anybody who knows Brian personally, like you can only imagine what on earth he must have thought. When this crazy lady with no experience or background just is insisting like that, he show up to these social things or the what? He was like, she's so crazy. I'm going to give her a project.

I notice you said your mentor suggested. Yeah. Right. Was that a company program at Cisco? Did you reach out to Cisco and find somebody? How did you do that? That again, just good fortune. I ask a lot of questions. So it's either going to get me fired or promoted. And I and I honestly think that's kind of how I roll. So some of that I don't know that I could teach or coach. That's just who I am because I don't do sitting still very well.

And I think you just for me, I was going to say this sort of to answer the first question. I do a calculation of not just like what's the scary part of leaping, but what's the cost of sitting still. And honestly, that terrifies me. That really is such a motivator for me. Probably says much about my psychology, but the fear of kind of rotting on the vine and, and being stuck is so much worse for me than whatever is over the next hill.

So given that you, it sounds like you, you know, ask the questions that you just kind of talked your way into a mentorship, which is great as a manager. Now, have you started anything to formalize that mentorship progress project or made that as an organizational thing? Well, I will say Cisco does have a formal program and I did that as well. I met some really interesting and cool people, diversify the group through that. As a, as a manager, I have always insisted that people not rely on just me and not to geek out, but I'm like single point of failure.

If I change jobs, if you want to change jobs, if you want to, I love this Harry Potter phrase. If you want to call me a barmy old codger, like you should have someone you can say that to probably better if it's not me for both of us, but I welcome you to say it, but let's let's find the right people for you. And I, so it's never, I've never honestly, and I respect that. I respect those formal programs. I think they're great as a way in, but I think like anything you get out of it, what you put into it.

So sometimes the formal thing is, is great and a super good match. I really think people should take it on themselves as part of their career path just to be interested in people around them and polite. And you can learn a ton. You just have to ask and listen and the education is out there for all of us. I really firmly believe that. And, and it, if you say like, Oh, I want to be mentored by the super famous person and I'm going to be really disappointed if I'm not then great.

That's aspirational, but cut through the part where you say I'm disappointed or it won't work out if I'm not mentored by that person. You can learn from everybody. I learned from my kids all the time. So the idea that you have to learn from someone on this higher plane, I just don't, I don't buy into that. Yeah. I don't prescribe for that either. You know, I look at this kind of like the prescribed tweets thing where organization sends out, this is what you should tweet and everyone, or you just tweet something along this line and everyone tweets the exact same.

Oh, the worst. Why does anybody think that's a good idea? That is click this link to tweet this. Oh my gosh. It is. I've had to use some strong language, but we, we pull it. Exactly. Yes. Yes. Chicken. Yes. Yes. So I've had this challenge and all the, what you've said, I just kept, I had to mute my mic as I was saying a man too much. One, one of the people actually went through before I made my career decision, I talked to in this, in the past month and a half was exactly Brian Grace Lee.

He gave me a little over a half an hour of his time, maybe a little bit more than that. And just talking through his experience and suggestions. And then also people would be surprised. I'll come out bluntly and say this because by the time this publishes, I would have announced it, that I made the decision to become a essay, a solutions architect at VMware. And I know a lot of eyebrows were raised because they're thinking, wait, Keith, you've done the cube.

You've done all these things. Why? Why essay role? And a lot of the decision was based on people that were not as far in their careers, minds, a lot of conversation, one-on-one conversations with Mark on just what drives me and what, what excites me and what gets me up in the morning and talking to customers. This is why I stopped the CTO advisor because I was not talking to customers and talking to customers is what, what gets me excited. And that's so important.

Yeah. I'm tick marking everything that you're saying. I'm like, Oh, Oh, this is, this is therapeutic. If you're not doing what you love, you're not going to enjoy your job. But if you don't enjoy your job, you're not going to have your job. No. And honestly, like when people joke of like, Oh, I enjoy eating chips and sitting on the couch. And I'm like, well, you in this day and age, you could probably figure out a way to make that make money too.

But within reason, like you said, I think there's such a cool amount of things that we can do that we're excited about and life is so short and there is a way there is a way to map. There really is a way to map what you love with what will get you paid. And it's magical when it works. And I just have to throw out one more thing. Cause I love Brian Gracely advisor to, to so many people. He's a great example of somebody, John Troyer, Matt Brody, the part about the hardest part about having mentors.

And I'm sure I'll get some more. Amen's here is you've got to get ones that will tell you the truth and you have to trust them enough to hear it and go, Oh, I don't want that to be the truth, but it is. And to listen. Right. I think, I think Mark literally in one of our Twitter discussions, he said something to the effect, it sounds like you'd be kind of stupid to take that job. I mean, I've, you know, I've known you a while.

I knew why you left your previous job. I know what you're looking for. And sometimes it's easy for all of us to chase after what we think is that one thing that we want. Oh yeah. You know, whether it's a title or money, a location, whatever it is. But in the end, those things don't make you happy. They really don't turn down like this senior director. You know, they're not going to make you happy if you don't have a job.

Most people, you know, you, these are once in a lifetime job opportunities, but you know, just having a mentor slash friend, who's able to just tell you like it is like, you know what? You can take that job. You make a ton of money. Whereas me and Mark like to say wheelbarrows of money. I love wheelbarrows full of money. I love wheelbarrows full of money just as much as the next guy, but you won't be happy. Now, you know, you can take that job.

You can make a ton of money. You can make a ton of money. You can make a ton of money. But you won't be happy. No. Yeah, it is. And honestly, every manager, every hiring person, you can feel it. I, if I had a dollar for every time I did an interview and I thought that that person, that person is on the couch eating chips and they don't even, you know, just care. Like it really is back to the whole coaching thing.

There's so many things you can teach. There's so many things you can coach, but you cannot, you can't coach passion. You can't coach interest. You can't coach curiosity. I can, I can help people temper those things or direct those things, but I can't make that out of whole cloth. And. When I, when I mentor people, I tell them, you know what? Describe to your, try to go to someone that's never been hungry and describe hunger to them. Oh yeah.

I tell them that, you know what? I can teach you how to feed yourself, but I can't teach you how to be hungry. That you have to, you have to have, you have to feel that yourself. Yep. let's face it. I think we're all really lucky in our careers, right? We could be doing things that are a billion times worse than what we do now. So it's agreed. That's great. I think we're all beyond lucky.

So I like to personally let other people feel that luck too. Right. I personally reached out to people who were working on a help desk, had a guy who was, he was a plumber, right? He got a, he somehow got a job on a help desk and I helped him work his career up from plumber to help desk technician to Linux admin to a guy who's running a Docker environment. Now he's still a plumber, just a different type of plumber. So those career paths exist.

And if you embrace the people who work in your organization, whether they work for you or not, in the end, the organization as a whole is going to be stronger and is going to be better. And you're going to feel better about yourself. All right. So we, we have to close out the, we can't go on talking forever, although we could, but people will stop listening. Maybe we have Amy. So we do have Amy, which helps out. I'll listen.

Oh, I thought I was the listener here. No, everybody went to sleep 20 minutes ago when I started talking. I have a very, I have a very sonorous voice apparently, because I used to put myself to sleep with it, listening to the key. When I'm traveling, my wife licks, listens to the podcast to help herself sleep. I don't know if that's because we're that boring or she just likes the sound of Keith's voice. I'm not really sure which way is scary.

Amy, how can people reach you? Oh, I welcome, I welcome people to, to reach out. I am most often on Twitter at comms Ninja. Um, and on LinkedIn, happy to connect and talk. Uh, and I really will. Uh, like I said, I, I believe in get paying it forward. Brian Gracely took the time with me. I tried to, uh, give, give my time to people, but often for difficult cases, I still have to refer them to the doctor.

Gracely, but thank you guys so much for the opportunity. I have enjoyed talking with both of you about your careers through the year. I'm so excited, Keith, that you're joining the band of Mary met. Yeah. Yeah. We've got, I'm in a Twitter DM with, uh, somebody. And it looks like I'll be one of five black guys. So, you know, I'm not, not exactly about the whole, the, you know, where my, my want to rethink this whole office, this loud black guy, a podium.

So I'm sure there's, I'm sure there's a, there's a Twitter handle ready and available. That guy at VMware. Yeah. So Mark, where can folks find you? You can find me on Twitter is at sensei storage or LinkedIn, or you can just, you know, hunt me down. It's not that hard. All right. And if you want to follow the ball black guy at VM, you can follow me. Oh, you know, that would be a great Twitter handle. The ball black guy at VMware.

I think it's number two, black guy number two. Yeah. I'm at CTO advisor on the web. com is where you can find the podcast. And if you want to put your mom, your wife, or your kids to sleep, you can subscribe them to the podcast by searching for the CTO advisor and your favorite podcast. Until then, we'll talk to you next CTO advisor podcast.