Tech leadership is about empowering teams, building trust, and championing diversity—creating an environment where everyone's voice is heard and valued. In this candid discussion, we sit down with Ruth Lee, CTO of Wave Mobile, to delve into the world of tech leadership, team dynamics, and the unique challenges faced by underrepresented individuals in the industry. Ruth discusses how she builds trust and empowers her teams, shedding light on the intricate process of evolving from micromanagement to a more self-driven approach. Moreover, as a queer woman in a predominantly male industry, Ruth touches on the challenges of being a diverse leader. She reveals strategies to create a safe space where team members from all backgrounds can thrive. Throughout the episode, Ruth reveals the tech world, the struggles of engineering management, and the need for change in the industry. Tune in to learn about tech leadership, and get inspired to champion diversity and positive change in your own professional journey.

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Empowering Teams And Championing Diversity: A Tech Leadership Journey With Ruth Lee

Before we start, I want to let you in on a little secret. Our guest is actually a dear friend of mine. If you hear us getting chatty, don’t be surprised. You have been warned. Get ready to meet Ruth Lee, a tech industry expert who is all about breaking the rules. Ruth’s journey in the tech industry began with a fascination for all things tech and a determination to make her mark. Trust me, you’ll hear that determination come through in this conversation. Starting from the trenches of engineering, Ruth climbed the ladder, and I actually saw her do it. As a CTO, she’s the driving force behind innovation and positive change in the industry.  

This episode covers a range of topics. We talked about Ruth’s early days navigating the tech landscape to her transition to management, and what makes a good manager. We even discussed how to manage your manager, and honestly, that’s my favorite topic. Ruth and I can talk about that for days. That’s not all. We will also explore Ruth’s insights on how to make tech a more inclusive and diverse space for everyone. If you’re wondering what’s up with the all-women-plumbing revolution that she’s about to start, maybe I’m about to join her in that, you’ll have to listen to find out. Sit back, grab your favorite beverage and always a snack, and let’s dive into this exciting adventure together. 

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How did you get started? How did you even become an Apple Genius? How did you go about making those moves? 

My degree is a double major in Jewish and Islamic Civilization and Film Studies. It’s not related. I spent a lot of time doing Near Eastern politics and history. When I graduated, it was during the 2008-2010 recession. A bunch of the jobs that I'd wanted was NATO, which got cut and wasn't available anymore due to funding. I ended up falling back on my old hobby. I'd always fix computers when I was a kid and used computers.  

I moved to London. I worked at an academic publisher for a time for no money. They were like, "You could come and be an editor." I was like, "That's so exciting." They were like, "For free." I was like, "That's an internship, not an editor." I had to decline that because it turns out you can't work for free if you live in London. I applied to a bunch of jobs, and then I got an interview with Apple at the Apple store. I started at the Apple store on the sales floor trying to convince people to buy Macs for their teenagers going to college. I was all right at that. I wasn't ever the best salesperson because I would tell people not to buy things.  

Most people who have been in Apple stores, you go in with your broken phone or your Mac. You find the first person and you're like, “Help. My computer is broken.” They're supposed to say, “Go book an appointment at the back and come back in six weeks.” However, I was able to fix a bunch of it. I'd be like, “Stand here with me and I'll fix it for you now.” At least if it was software bugs. After a little bit of that, my manager got sick of me doing that instead of selling things. He was like, “Why don't you go fix Macs?” That's how I became a Mac Genius. I used to walk around and tell everyone I was a genius, which was technically true at that time. 

This is new for me. I did not know about your degree in Jewish and Islamic History.  

It’s technically Theology and Ancient Civilization, and Modern Politics as well. It covered everything. It was Near Eastern Historical, Theology, and Modern Politics. 

You've done amazing work in tech and you are a CTO now. Clearly, you know what you're doing and you're good at it. Did you ever think about going back and looking for jobs?  

Yeah, maybe up until I became a Sys Ad. From Apple, I got this mad interview for a support person where I was supposed to know about Linux, but I didn't know anything about it and the guy who hired me said, “If you don't learn in six months, I'll fire you, but I'll give you a shot.” I did that and that was good. That was a stepping stone to get into being a Sys Admin. Sys Admin was cool because you were working on the computers. Also, more importantly, that was where you made money. Up until then, I was either minimum wage or just above it. Up until I got to Sys Ad, I was interested in going back and doing what my degree should have been about. 

We are talking about your life in tech. Tell me about moving from a technical position to a management position. What motivated you? I see you were doing Sys Admin work. Apple Genius also is not management work, and then you were doing the SRE work. You were good at it, and then you moved into management. What motivated you to make that change? Anything in particular that made you go, "I need to be a manager now. This is what I'm going to do." 

Two things. One, I was on quite a small team. Historically and also at that time, I had very little management interaction and support from my manager at the time. That meant that things for the team were extremely difficult. To be clear, retrospectively, this was a lack of support for that manager from his manager. This was a systemic issue, not a single-person issue.  

I felt like the team was constantly underwater or being yanked back and forth between priorities, overworked, and people didn't know what was going on. My boss' boss came to me and was like, "You are going to be a manager now." I had a choice but I didn't have a choice. I could have said no to that. The person who asked me to take the role was at the time very much up and coming in the organization, and was on their way to being extremely influential. I might as well have decided to never get promoted and have to leave the company if I hadn’t taken this opportunity. 

It turned out that his instincts were pretty good. He was right to force my hand a little bit. To be clear, I was offered a tech lead role. I was told, “You don't have to do much management.” I was like, “Cool.” Cute lie, I became a manager. I was a manager and they never changed the title. I was like, “Why does my thing say manager when it's tech lead?” Everyone was like, “We don't have the title of tech lead yet.” That was sus. Two years later, I was like, “I'm a manager.” That was that.  

Respectively, part of my reason for wanting to do it was the desire to make things better for the team and to think that I could have an impact. While at the time I felt that was almost motivated by spite or the decision that someone has to do it, so it might as well be me. Retrospectively, I'm like, “That was great.” I was keen to do those things and be able to help folks, but I didn't necessarily feel that I would necessarily do a great job at it.  

I didn't want to say, “I'm going to make things better for everyone,” and then fail at it. I used, “The current management isn't bad. How bad could I be in comparison?” as I wiggled in, but I wanted to do a good job and have people say that I was a good manager and had influenced them in some way to be happier at work, at least.  

This is instance number two where people are giving you a chance to prove yourself or they believe that you can do something even with the Linux admin job where you're like, "I don't have the skills." The guy was like, "I'm going to give you six months." You take that and make something amazing out of it where you're like, "I don't know how to go about it." It's amazing that you learn on the job and you deliver well.

It probably reflects on the people who gave me the shot that they're good at identifying stubbornness or whatever it is, “You be good at it.”

Ruth, take a freaking compliment. You're good at it too.

That too. I also think that now being in the position where I do that for other people, it is a skill to be able to identify who will rise to it and who will flounder. You give me a challenge and I'm going to go put 100% in. Usually, previous evidence shows, I could do as well at it and that's great, but being able to pick those people when you don't necessarily have insight into their previous responses is hard. Now, I'm interested almost in going back and asking those people, "What made you pick me without this previous information of how I'd done before? I would like to have that ability to do that more effectively."

Someone gave you the job because they taught you would rise to the occasion. Did you have a moment when you were like, “I can do this. I'm good at it, and I'm going to continue doing this?”

Normally I have that moment when I've stopped doing the job, when I get promoted or I move to the next level. I then look back and I'm like, “I was good at that thing.” It's hard to tell, especially for me in leadership positions, whether you are good at something because most of the feedback that you get is things that need to be fixed or improvements that you can make and rarely do you get positive feedback. Normally you get that.

I've mainly got that as a manager. When I left to go to a different role, people on my team came up to me and said, "You were the best manager I've ever had." That's so wonderful to hear, but it would've been nice to hear during the two years I was your manager. Now I say that there was one person who worked on my team when I was at Splunk with you who recommended other people to the team and said to me, “I recommended this person and told them you were great to work for.” That made me go home and sit down and think, “I'm achieving what I wanted, which is a safe shelter in the stormy world of tech for people.”

Anytime I've got feedback from people on my team that says, “I want to work with you. I recommended you to someone. I don't want to leave the team because I like working on your team,” those are generally the most meaningful positive piece of feedback I get. I get them from your VP or your CEO who says, “You're doing a great job.” That's fine. It's important to do a good job for the company, but that's not fundamentally the motivator for me to do my job.

It's also feedback for people like us. We don't look like traditional people in tech. I'm Indian. As a software developer, there are a lot of people who look like you. In leadership especially, there are not a lot of people who look like you, act like you, motivate others like you, and manage like you. Getting feedback on how you're doing can be essential because you have no system to learn from or footsteps to follow. You are creating that as you go. It is hard. You end up questioning what you do a lot. Given that I know you, it is quite possible to be like, “Ruth knows what she's doing. She's never questioning herself. She's all great. Ruth is fine,” which you are but I bet it’s that feedback or knowing, “I'm doing okay. My engineers like me.”

One of the things that is useful I have that’s a double-edged sword is I tend to be somewhat overconfident. That's useful. it's important in a leadership role. You don't stuff that anxiety. You have confidence in what you're doing. Sometimes that is overconfidence. Sometimes it's an appropriate amount of, "Someone has to pretend they know what's going on." That's pretty much for me what a lot of leadership is. It's that thing where you're an adult and you're doing your taxes and you're like, "Was this how my parents felt? They didn't know what was happening either. Everyone who's 35 doesn't know what's going on." It's exactly the same for me.

To be somewhat overconfident can be useful and even important in a leadership role. Someone has to pretend they know what's going on.

That was me when I turned 26. For some reason, 26 was the time when I was like, "My parents had no idea what they were doing. They were going around making rules like, "This is when you go to bed. This is when you eat. This is when you do this." It's like, "No, sir. You have no idea what you're doing, so please stop." Before we go to another tangent, what do you think are the most essential or important skills? You've touched upon this a little bit, being able to recognize talent within your team, but what would you say in your experience are the most essential skills of a competent manager?

There are three. One is you have to be empathetic. If you don't have empathy, you're not going to be able to manage a team or understand the team's struggles. Also, people can tell when you're not empathetic. They know the difference between sympathy and empathy, and they don't like it.

Can you elaborate on the difference between sympathy and empathy? I feel people confuse it all the time.

I'll give you the most simple analogy that I use for this. Let's say you're having an argument with someone or someone disagrees with you. Sympathy is when you say that horrible thing that is, “I'm sorry you feel that way.” It feels bad to hear that. Empathy is saying, “I understand why you feel like this. I would feel like this too if these things happened to me.”

It's that alignment where you're not only acknowledging the validity but you're expressing that you understand how they came to that feeling. Nobody likes, “I'm sorry you feel that way. Come on. Are you? No, you're not. You're just saying it.” Whereas empathy shows, “I understand why you feel that way.” It doesn't have to mean that they're right to feel that way or that you agree with them feeling that way. It says, “I understand.” That's different.

Thank you. You were saying the number one skill is empathy.

Number two is personal resiliency. This is a pattern that I often see with new managers and some managers who burn out. They're very empathetic. People often want to be a manager because they care about seeing when bad things are happening to their team or those around them. They care about the team. This backfires often when they become a manager because that empathy means they over-index an individual's feelings. When you manage a team, almost always, someone is subtly losing out. You choose to give a big project to one person, that means someone else doesn't get it. You choose to promote one person. That means someone else doesn't get it. You choose the direction of the team. Someone is always going to disagree.

You're never making everyone happy. When you're empathetic and you don't have your own personal resiliency to that, that can become extremely draining and upsetting when those people express anger, frustration, or contempt sometimes towards you because of those decisions that you've had to make. If you don't have resiliency, you either over-index on them, you start making bad decisions, or it screws you up. Your personal life becomes bad. You end up depressed, bummed out, hurt, trying to grapple with that. When we're hurt, we tend to act out in different ways.

When you're a manager, acting out is quite dangerous because you have power. Depending on how you choose to act out in reaction to that hurt, whether or not you're conscious of it, can often be lopsided in terms of its effect. Someone on your team might hurt you and you might react in a way that truly damages their career or impacts them. These are unusual. It's normally much more minor. It's important to have an equal balance of those two things, empathy, and resiliency so that you don't get stuck in that trap.

The third thing is technical. It's being able to make decisions. Not getting into an anxiety whirlpool, being good at making quick decisions, not second-guessing yourself, and moving forward. I fundamentally always say, “A manager is there to make the decisions no one else wants to because they're scary.” You have to make those and be okay with making them. You can learn to do that. You can modify empathy and resiliency somewhat. You can somewhat learn resiliency and empathy. Those are the two components that without those, you will always struggle in some way.

You said technical. Do you think the technical knowledge or the project knowledge is important? If so, to what extent?

It depends on the team. You can be a much more non-technical manager when your team is say twelve people with a high spread of seniors with a senior principal engineer, fine. You can be pretty non-technical. It isn't a problem. If you have a small team and there are a couple of juniors and a couple of similarly leveled seniors with no obvious leader, for technical decision-making, then it's going to be pretty damaging. Fundamentally, all managers in engineering should have a technical background and should have worked in technical roles, mainly because they will have at some point suffered from bad management in some way or understand the specific frustrations of the job. It's less and less necessary the further up in leadership you go.

Theoretically, an extremely competent COO or Chief Operating Officer could probably be a CTO, depending on the company as well. They can be interchangeable. Organizations tend to function similarly. Once you get to an organizational level, it's somewhat less important. By the time you get there, you're far enough away from your technical background that some of that knowledge has atrophied. Certainly, as a line manager and hopefully, all the way up to CTO, it's important to at least be able to have the respect of the people who you're ostensibly leading. For a lot of engineers, that does mean that you should be able to follow along a pretty baseline technical discussion and give some feedback or advice to them based on it.

That part is interesting that you bring that up. The respect from the people who are reporting to you, and the technical background helps with that, even though it sounds like something that shouldn't matter. If you're a good manager, if you have those skills, and if you are being productive, I don't understand why we engineers have a difficult time respecting that, but there is a certain level of, “You get what we're doing. You understand.”

The industry undersells leadership everywhere. We push great engineers into leadership roles because we're like, “How hard can it be? You're smart. You can be a leader.” Traditionally, tech doesn't put enough weight into good leadership. Also, I agree with it. I do think if you're going to lead an organization of people doing a specific job, you should have some experience doing that job.

There's enough nuance in the tech industry, at least for me to say that it's a requirement. I wouldn't take someone who let's say was a school principal, even though there are a lot of overlaps between being a school principal and managing a large engineering org. I don't think that they would be capable of doing the job because they don't have the fundamental knowledge of what the job is like and what it's like to be an engineer. To have empathy, you need to have somewhat experienced that. It all comes back to, “Are you able to empathize with everyone within your organization, and to do so in a way that feels genuine?” You probably need to have been in a similar role.

I'm going to move on to our personal favorite subject, which is managing your manager. It's a whole thing and I want to spend a little time talking about it and what it takes because it's a skill. We've had long conversations about it, but let's start with why you need to learn how to manage your manager, even if you have a good manager. Honestly, if you have a good manager, then probably you don't need to, and you are lucky. However, in most cases, you do need to manage your manager. Let's pause and talk about why that is necessary.

If you have a good manager, being a good manager is allowing your employees to manage you. Making that explicit. The reasons why it's important to be able to manage your manager is essentially, you're trying to create an environment where you can have accountability, but you're able to be as productive as possible in the way that works for you, but that also works with the team.

Being a good manager is allowing your employees to manage you.

The manager is largely responsible for team processes, and then you are responsible for helping your manager interact with you in a way that keeps you productive and unfrustrated. That's what we're trying to get to. We're trying to minimize friction in doing the engineering work that matters. That's what fundamentally managing your manager is about.

To use a basic example of status updates, working out clearly upfront like, “I would prefer to give status updates over Slack once a day. The Daily Notes function doesn't work for me. What are the options for me to give my updates in a different way? Can we have a face-to-face for 10 minutes every 2 days because that's much easier? I don't like typing things up. It distracts the flow.”

It's about working to find a compromise that helps you to be as effective as possible as an individual within the team while the team operates in a way that's as effective as possible. Now those two things can sometimes be in conflict and that's where if you have a good relationship, you can help decide whether the team takes the hit or you take the hit in productivity. Fundamentally, what you're trying to do is work out how each other works best and then how to adapt.

You mentioned some tips and anecdotes already. How would you effectively manage upward or build a solid relationship with your superiors?

There are two things that you need to get clear with whoever your boss is. Number one is what are their expectations for you reporting in, like giving status updates? They're going to delegate something to you and they don't want that to go into a black box void and never come out, or maybe they do. You don't know that. That changes, depending on your manager and depending on the level that you're at in the company. You should check in on that. The first thing you should do is, “How do you like to have updates? If you delegate me a piece of work, what kind of update would you like?”

The second thing that is important is to understand the remit of that delegation. You might have heard people talking about this. Do you want a review or do you want a preview? I will sometimes talk about this with my directors at the moment. I'll say, "My expectation of this is you'll give me a preview or you'll ask me what decision I need to take. You can solve this from top to bottom and you can tell me what happened." Be clear when someone asks you to do a piece of work and say, “How do you want to hear the status of the work? Do you want frequent updates? Do you want to know if it's off track? Do you want to never hear about it again? What's your deal on this?”

Secondly, for important decisions, if something changes the scope, do you want to make the decision? Do you want me to make the decision and tell you? Do you want me to suggest the decision that you should make too? Which of those options would you like? Those will change from project to project. For a small-scope project, it isn't that important. I'm probably going to say to you if I'm your manager, “Black box it. You don't even have to tell me if it's done. I'm going to trust that it gets done. Make all the decisions for yourself.”

For something that is super important. Maybe it has cross-team reporting or they're getting heat from their boss on. If you ask them that, they're going to say, “Can I have an update at the end of every working day? Can you tell me if we're on track or off track? If there's a big decision, can you let me know that there's a big decision and what you suggest, but wait for me to decide? I might have to ask some shadowy stakeholder that you don't know about.”

That is instantaneously helpful because there's no one way to work it. That means that all the things in terms of project and project management are covered. Most of the time, when there's tension or where you are struggling to work with someone, it's almost always because those expectations are not explicit. They are always explicit. Someone goes, “The last time I did something, you wanted it this way.” Work is different. Situations change. Recognize that difference. Those are the only key things that you have to do. Even if your manager is awful and they're horrible to you, if you do these two things, you will have a better relationship with them. It will keep them from breathing down your neck persistently.

This is great for micromanaging managers. It's great if your manager is a good delegator and doesn't care because it makes them feel more comfortable delegating you more work and you feel more comfortable. There are two bad sides, the micromanager and then the one who says, “Do this,” and then never talks to you about it again. That's terrifying too. Those are the only two things I tell people to focus on. All the other stuff like, “How do you like to be spoken to? How do you like feedback?” That's all gravy beyond that. If you get those two bits wrong, both of you are going to have an unpleasant time working together.

Can you elaborate on how I would use these two things to get to the next level? The question is always you work with your manager to get a promotion to get to the next level. That is an important aspect of managing your manager. In terms of setting expectations and scope changes, how would I use these two things to get to the next level and have that agreement with my manager?

If you're good about setting these per project, then it happens automatically for you for the most part. When I talk about what makes a senior engineer with people, I always use the same thing. A senior engineer is someone who I can turn to and say, “There's a problem. Here's the problem. Please make it not a problem.” I then know that I don't have to talk to that person again because I'm getting the right amount of updates and I trust their judgment. Over time, what happens with an engineer is the first project you delegate, the more that your manager gives to you and says, "How many updates do you want? Do you want to make all the decisions?" Almost always the manager is going to say, “I want loads of updates and make all the decisions.”

You'll do maybe two projects like that, and then they start to trust you a little bit more. You learn a little bit about the tiny decisions they would make, and the decisions that make sense so that you can start making similar decisions. The next one, they should be releasing the reins a little bit. By the time that progresses, they eventually trust you enough to know that they're going to get the response that they need. It's this idea of building trust in the relationship.

This should happen naturally. If it doesn't, then you have a great leg to stand on when you're trying to go for promotion and they say, “I'm sorry. You haven't done enough on a self-driven project." You say, "For the last six projects I asked you what updates and how much decision-making power you want. On each of them, you wanted daily updates and you wanted to make all the decisions. You are not providing the opportunities to me. I know this because we've agreed on the level of my scope beforehand.”

This idea of building trust over the relationship, this should happen naturally.

You are already evidencing, “I'm not getting these opportunities.” That doesn't mean you're going to get promoted, but it means you force them into giving you the opportunities. They can't say, “I'm sorry you didn't show enough proactive movement and guidance in your own work.” People love to say that to you. It's like, “How could I do that when you told me that you wanted to make all the decisions?”

That's hard because you're automatically falling into that pattern that they always want to make the decisions and you haven't upfront said who's making the decisions. If you do that upfront over Slack, an email thread, or even better, in a document, then later on, when they say you didn't show enough proactive decision-making, you can say, “At the beginning of this project, we agreed that I would provide you with two options and you would make the decisions. It wasn't possible for me to demonstrate that.”

As you said, it's not that the requirement is now gone from your promotion process. It’s explicitly out there and it's written down, and so for the next quarter or next cycle, you can you can work on that part.

To be clear, this is rare. Most people don't get these opportunities or hear this proactive thing spun because the manager doesn't necessarily have the language to express, “I don't trust you yet. I'm not sure how we build that trust.” Managers aren't trained in the tech industry space. No one gets training. You get made a manager and then you tattle off and try to HR a bit, but you never get trained. You never get resources put into you.

How many conferences do engineers go to? You never see a manager going on a leadership course. It doesn't happen. At least not through companies. Occasionally, they do. I've been on a women in leadership training before. I can't say that I learned a lot, but the quality of the education for leaders is significantly below the quality of the education for engineers. Let's leave it at that.

Setting expectations and defining what success looks like at the end of the process is essential. If anything changes, how are you communicating that upwards? Those are two things. We should think about writing a book. We did talk about a talk that we would do on managing your manager, but write a book.

Do we have time for that talk? They were like, “We don’t want that. We don't want a principal engineer and a senior manager talking about how to work cooperatively together. Get out.”

“We can't have managers and ICs getting along with each other.”

“They'll become too powerful.”

“They'll take over. No, thank you.” That would've been so good. Anyway, another day.

We can still do it separately. We should start submitting to conferences separate from our companies.

We don't have a lot of projects going on. We’ll sign up for more.

You're doing nothing. My job is so low-stress and unimportant.

Let's sign up for more things to do. That's a good idea for us. Coming back, there’s one last question I want to ask you before we go into Rapid Fire. Can you share any strategies that you have found effective in fostering a diverse range of perspectives and backgrounds within your team? As a manager with a diverse background, there are not a lot of people who look like us in leadership roles. We're here to change the landscape a little bit if we can. How are you as a CTO doing that?

This is difficult because if I answer this honestly, which is one of my company’s values is embarrassingly honest, which I equally hate but love, I don't think I do a good job of this. I get by because people perceive me as having a diverse background. They're like, “A queer woman.” That default makes them feel safer. I can coast on that. Automatically, it's safer because maybe I have some experience of discrimination in some ways and they feel more open sharing with me. I try to do a good job of this and ask people for their opinions. I try to signal where we can, small things like in your Zoom name, put your pronouns, and do it in Slack.

Things like that are helpful. One of the things that we struggle with as an engineering organization is hiring and retaining African engineers, which given that our customers are all sub-Saharan African, it sucks. I do what I can to make sure that we don't take the ownership of helping mentor, teach, and embrace those engineers on the other African engineers at the company. I try to make sure that we're not asking people to solve for diversity within their own community, as I'm sure has happened to you.

People love to ask me, "Can you go to this tech conference and tell them it's good here?" That's exhausting. You don't want to be the poster child. Sometimes you want to be known as a good CTO or engineer instead of, "Isn't it great that you're a queer woman?" I'm like, "Isn't it great that I'm good at my job? Have we tried that one?" I try hard to not do that to people, but there's always massive room for improvement.

I do think it's easier for me. I get to say, “I'm a minority too.” Some of that heat gets taken away. I often wonder if I was a cis White man doing the same things I'm doing now, would people view me as championing diversity? I don't think so. Probably not. They might say, “He's trying.” That's about what I'd get. This is the thing I'm still trying to work on and get better at.

As a friend, I feel the pull to be like, “You are trying.” You are probably facing a lot of discrimination as a CTO and as a queer woman yourself. To manage that and then also create an environment where people can share their backgrounds with you or feel this is a safe space is a lot. You are trying your best. There's also a pull to be like, “Thank you for recognizing that.” Thank you for recognizing you could be doing more. If you are trying, there's more that you could be doing.

We should all hold each other to higher standards. I'm lucky to have a lot of people in my life. I sometimes ask them about things I'm doing. They're like, “Cool, thanks for the minimum.” I'm like, “Okay.”

We're going to do Rapid Fire. I don't have a lot prepared for us, but we already went through a lot of prepared questions and such. Do you have any advice for someone who's trying to decide between a career in management or continuing as an individual contributor? I've asked you this question for myself.

I don't think you can condense this into rapid-fire answers. What I would say is to find someone you trust who is in a leadership role. Depending on the company, you walk into a different situation. If you can, try and find someone you trust that will give you a real honest conversation about it. If not, find someone elsewhere outside of the organization who has made that transition, who you can talk to, and who is willing to take an hour to dig into, "What are your expectations? Are you ready for these things to be hard? How would they make you feel?" They can give you a real rundown of the things to consider. We've introduced at my company a growing leaders' program, which is a mini-version of our manager training.

In the end, the last session is us being like, “What if you hate it? What things are you most dreading about doing this job? What struggles will you have?” We're honest about the fact that if you move into a management job, you will be bad at it and that will affect people. You have to be okay with being initially bad at it. That can be tough.

Having someone to have those conversations with and ideally, if you can have those conversations with, another peer who's also new to the transition or considering the transition. Those are helpful because they can force you to analyze your motives and the impact that they will have on your personal life and your mental health as well. It is a transition that I've seen a few people suffer from and get burnt out or choose to leave the industry and do a bunch of drastic things in response to work-related stress from making this move. It's great. I loved it. It was a great move for me. Find someone who you can talk to so you go into that eyes open if you do decide to make the change.

I remember setting up a call with you to have this conversation and it was a long conversation.

I told you not to do it.

In classic me-fashion, I did try it. There's that.

I almost always say don't because if you want to do it enough that you'll push back on that advice, then it's probably a good idea for you.

I'm also hearing that you would record another episode on just IC versus management. Thank you for that. I appreciate it. Can you share a memorable incident that has influenced your approach to technical leadership or your journey in the industry?

Yes, but it's not very nice. It is the reason that I stay in the industry in a weird way in some way. There was a company that I had a job at a long time ago. There was an incident that ended up at HR where I did not feel that my manager supported me. Retrospectively, it was extremely egregious and may be illegal. In some senses, it was bad. There were no consequences for the person on the other side. You can guess it's sexual harassment. There were no consequences.

The consequence was that I got shunted off somewhere else and told to keep my mouth shut. I saw that pattern. I then had the same pattern happen multiple times with less extreme incidents, but still pretty bad ones like colleagues telling rape jokes in front of you and laughing about it, saying that you could be their secretary. These things repeatedly happen to me. I saw that management was doing nothing and I couldn't tell whether they didn't feel empowered, they didn't recognize it, they were scared, and didn't know what to do. I remember thinking, “This is terrible. How can a manager stand there?”

I'll give you another example. It was International Women's Day and they tried to be like, “Happy International Women's Day.” One of my colleagues was like, “Is Ruth going to go make us all sandwiches in the kitchen?” I laughed and I remember that moment. It was after a whole bunch of these things. It was the final moment. At which point, I was like, “That's it. I'm going to rise to power in this stupid industry. I’m going to take over and fire all of these people for breaking company policy.” That's the thing.

As company leaders, especially at a senior level, you don't want that to happen, but this happens because we don't train our managers well. We don't set those boundaries. Anytime I questioned like, “Maybe I'll quit and go live in the countryside,” I was like, “No if I can change this for one person in the industry that's not their experience. They know that if this happens with the company, I'm going to come down with a bag of bricks on that person and it's not acceptable, then it's 100% worth it to me to put up with all the other nonsense in tech like a million Zoom meetings or whatever it is that's getting my goal at that day.”

This is good and I've been able to do it once or twice when things have happened. I've been able to turn around and go, “Not on my watch. Let's go to our friends at HR.” That has felt extremely satisfying. Now, it doesn't happen at all, which speaks a lot to the company I'm at. Also, I'd like to hope. It speaks to the fact that people know it's not going to fly if I'm in the room or even in the vicinity. That motivated me to stay in a management role, which seems weird because it's negative motivation. It's a positive reason. It was a bad experience that I'm like, “Let's have good experiences for everyone else.”

This is not a negative. There are two ways that I'm feeling about it. First of all, I'm like, “Go get a boot.” Also, you shouldn't feel the weight of the entire industry or have to fixate on you.

I don't feel the weight of the industry. I'm like, “If you all are going to suck, at least let me make a nice little corner. Let's come hang in the nice corner because we don't need that. Nobody needs that in their life.”

I love that you are in tech and you are doing what you are doing. Ruth, why tech after all these years? This is my favorite question.

Cash money. A lot of things. To be clear, it's not just about the money, but I do think in tech, we are lucky to work in an industry that is probably severely overpaid. I use the comparison to Wall Street in the ‘80s. The tech crash has made that even more obvious. The tech industry has a lot of money flying about for stupid reasons. I don't see why I shouldn't take advantage of that.

Money is nice. Being able to bring your partner on nice holidays is nice. Being able to buy your parents stuff and bring them on holidays is also nice. There are other things that keep me motivated. To be clear, the role I'm in and the company that I'm at now, I fundamentally believe it is doing the thing that's beneficial for people. I didn't always feel that way in my previous companies.

The tech industry has a lot of money flying about for stupid reasons and some people don't see why we shouldn't take advantage of that. Money is nice being able to bring your partner on.

That helps me stay motivated. For me to stay in the industry, I'm going to have to be careful that whatever jobs I pick align with, at least, if I'm going to make a lot of money, I want to feel the company is doing good as well. It has been nice to work for a company where I feel the end product is beneficial to people on a fundamental level and that we're trying to do a good thing for our users.

At the end of the day, it's also a company and a business. It's not full charity, pat myself on the back. It's nice to feel you can make a difference and when people say, “I've enjoyed working with you,” or give you good feedback. That feels good as well. Those are motivating as well. We're all a bit too embarrassed to say the money is good and that's quite nice.

I wanted to ask you that because I could expect 100% honesty from you. If you weren't in the tech industry, what alternative career path would you have? We touched on this a little bit.

I want to go back to that now. We all have the get-out-of-tech fantasy. What are we going to do when we leave tech? This is bizarre but you'll love it. I would love to found an all-women plumbing company. The trades are vital. You always need trades. Especially, when you’re plumbing goes, you need someone ASAP. You have a desperate market. Third, when I moved into my house alone, before I met my wonderful fiancé, when I would have a tradesperson around, it was always these big dudes.

I always found myself saying things like, “My husband is traveling for business.” They’re like, “Do you live here alone?” I'm like, “No, my boyfriend is at the gym.” I suddenly had these moments where I was alone with a big guy or a locksmith and I was afraid. The woman who fitted my kitchen was great. I realized even though she was an imposing person, at no point when I was alone in the house with her or I gave her a set of my keys, at no point did I feel uncomfortable about that. I was like, “I feel safe around this.”

I thought, there are so many single moms, single parents, or single women out there who would happily pay for a woman to come to do their plumbing in the middle of the night in an emergency and have somebody who's going to be respectful and pleasant in their home. Also, plumbing and the trades are terrible industries. I tried to book an electrician. I had to bring 50 numbers and people were like, “I'll text you when I'm free.” I'm like, “Why don't you just have a website that I can go book on?” No one has a website. I'm like, “Do you know what I and my generation hate doing? Phone calls.”

Let me book it. Why can't I do that? It feels so obvious that you could do that but there's no facility for it. Why can't I video-call a plumber? Why can't I say, “Look at this thing,” and then they can tell me, “There's no option for that?” To wind you up specifically, it's an industry that needs disruption.

I was with you until you said that. You are right on the plumbing part of it, not the disruption part of it because even when my partner would not be home, now that we live together, it's different. I can send him and be like, “Can you deal with the people, please? Thank you.” Otherwise, I would call him over and be like, “Can you be home for this? I'm going to be with their dogs in the other room and lock myself.”

I have to bring men with me when I go to the mechanic because they talk to them. I'm like, “Why? I want to talk to an electrician who's not trying to rip me off because they're like, “Stupid girly.”

She's not going to know.

Maybe I'm sure women do it too to other women, let's be honest, but I feel like I don't expect that. As long as I don't think it's happening, it's not hurting me. It's only when it's happening that it hurts me.

Take more money as long as you don't say we are trying to disrupt the industry. Lastly, where can people find you, Ruth?

Not many places to be honest. LinkedIn is the only professional presence I have. I had a Twitter, but now, we don't support that site, so that's the end of that. Mainly LinkedIn, or they can email me at my company address which is also on LinkedIn, which is Ruth.Lee@Wave.com.

This has been wonderful, Ruth. We did it. We stayed on the topic mostly. I love this. Thank you.

Important Links

• Ruth Lee – LinkedIn

• Twitter - Ruth Lee

• Ruth.Lee@Wave.com