The Ruby Rogues

The Ruby Rogues podcast is a panel discussion about topics relating to programming, careers, community, and Ruby. We release a conversation with notable programmers and Rubyists each week to help programmers advance in their careers and skills.


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276 RR Hiring and Retention with Kenzi Connor

1:15 – Introducing Kenzi Connor

4:15 – Senior developer vs Junior developer: Sustainability and hiring

8:25 –  Examining the “senior-obsessed field”

10:00 – Importance of sustainability

12:35 – Lottery-ticket thinking

13:35 – Solutions to the junior vs senior dilemma

21:10 – Diversity and productivity

23:50 – Effective management strategies

31:00 – Strategies for going from a high-conformity company to a more diverse company

36:05 – Why junior developers leave your company


Mandy Moore (Sam)

Seven Wonders of a Once and Future World by Caroline Yoachim (Jessica)

Foreign exchange students (Charles)

Octavia Butler (Kenzi)

Black Girls Code  (Kenzi)


This episode is sponsored by

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Charles: Hey everybody and welcome to Episode 276 of the Ruby Rogues Podcast. This week on our panel we have Jessica Kerr.

Jessica: Good morning!

Charles: Sam Livingston-Gray.

Sam: Oh, we’re doing this now, are we?

Charles: I’m Charles Max Wood from Devchat.TV. Check out We also have a special guest this week and that’s Kenzi Connor.

Kenzi: Hi, nice to talk with you all. Have we met, Chuck?

Charles: I don’t think so. We might’ve. I make it to so many conferences in a year that it’s possible.

Kenzi: I’m more of a former conference goer, I’m getting back out there. That whole running the business thing doesn’t always mean you go to all the tech conferences anymore.

Charles: Don’t I know it? I’ve had a few people invite me out to them. I’m bad at saying no.

Kenzi: Ah, yes. I’m needing to get back to more and figure out a new range of talks that are more management or giving out most of the data they code anymore. I should be interacting with as that of a consultancy, I do a lot of sales in addition to hiring, I do need to figure out some sort of hey, you’re a manager now when you used to be an engineer, what’s that like?

Charles: Gotcha. In fact, why don’t you give us a quick introduction so people know who you are.

Kenzi: Yup. I’m Kenzi Connor, I used to be formerly known as Timocratic online before I transitioned which I was worn on the Ruby space as. I started developing professionally around 2000 and in 2005 we discovered Rails and had done Java, .net just started, PHP, Python, a couple of other things that were all awful. Rails came on the scene and we’re like oh my god, this is so much better than all the other ways we were doing it. We went all in on it since then.

In some ways I’m a little bit of a crusty old hand in the Ruby space, even worse in frontend. I’ve really had to deal with generation four browsers, I just shouldn’t write frontend anymore because I’ll just be, “Oh, we have to do all these things.” And everyone’s like no, we don’t anymore.

It’s a former engineer and I run a consultancy cloud setting that we do, Devon designed for web and mobile. Pretty much everything you would need to get an app shipped with a pretty big focus on that, on the design and development that integrates well is super high priority.

I’ve spent some time in other well known consultancies. Usually, you either have a design firm which does great design that no one can build anything practical out of or engineering firm that slices, does XP, slices features down to their smaller set and sort of ruins the overall product idea. Trying to reemerge those back into sort of a Linux part of why we started my consultancy in 2010.

Charles: Gotcha. When we were talking about topic, and I think this leads right in with your introduction, one that you suggested was the challenges of sustainability and hiring in a senior obsessed field especially during the bootcamp grads. There’s companies that don’t know how to do mentorship. There’s a whole lot more there but let’s just start with that.

Kenzi: The irony of that one for me is as a consultancy, I can’t help as much as I thought I would be able to. I used to try and hire juniors and train them up and have a broader range of skill set. The economics just aren’t there because there are clients paying us to train someone. I’ve actually had this argument with a number of consultancy owners that I think it’s unethical.

On the edge of unethical is to charge someone for your juniors because you understand the difference between junior and senior when it comes to an hourly bill rate and efficiency in a way they don’t. You know you’re paying half as much for this person but you’re getting one fifth overall as productivity, that’s a bad value for you as a client. It’s heartbreaking for me because I do so firmly believe the field isn’t super sustainable and your hiring in your company are better if you can bring in more juniors. I haven’t yet cracked how to do that at a senior level because consultancy, we believe in mentorship and we bring up people whenever we can.

A lot of the clients who have been doing Rails come to us because we know how to scale and build up Rails apps. The maintainer bundle works for us, we sell the problems. But if when we’re at a product company, there would be absolutely no reason I should’ve taken a much different approach. There’s a difference when you’re investing to train your own people.

Charles: It’s funny that you mention that though because my first development job, full time—I had been developing for maybe a year at my previous job but it wasn’t my full time job. My full time job was running tech support and then doing QA. My first full time development job was at a consultancy and I was billed out to clients for a year and a half.

Kenzi: I have been there, that’s how I got started. San Francisco is significantly more competitive than Utah where I got started as part of it. Once your company is established based on seniors and a whole bunch of other factors, it’s hard to do otherwise. I feel that one of the companies that was charging me out as a senior when I had a year of experience was exceedingly unethical in doing so. If you do a value sale of hey, the person agreed. If they agree to we’re billing this thing in this amount of time, what’s the value to you, that’s a different thing.

But in places that are doing time and material and you’re saying hey, this is how much someone is worth. If you’re pretending like your process is good enough, that the end result to the client is the same for someone with 15 years and 6 months experience and billing amount the same, I just have problems about the ethics of that and the effect it has on your good name over time.

Charles: That’s fair.

Kenzi: I used to make the pitch because I believed in it that you could do a mixed rate, like a blend of junior and senior. I feel the value for a client would be better if they hired a junior, we train them up. Then, if they’re investing in someone that will turn around long term, they’re sure to getting the benefits of that.

Sam: That’s an interesting idea, I like that.

Kenzi: At the end of the day, everyone is like what about availability? Like yeah, I as a consultancy can’t find enough seniors, it’s not on you to subsidize my juniors because of my inability to hire them. Then, you should go find another consultancy also that has more seniors.

Sam: You made a pretty compelling case for the pressures against hiring juniors in a consultancy. In your email when we’re talking about the subject, you used the phrase “senior obsessed field” which I’ve certainly seen as well, I love that phrase. Why do you think that the field overall is so set on hiring senior folks?

Kenzi: I will add in another tidbit there which is that that also factors into why I have trouble in the consultancy because I have to play to my client’s biases and expectations. I have noticed that if they don’t believe someone can do something and start questioning something, then you might as well end that part of that engagement because in every step along the way they won’t feel that they’re getting the value and they’ll doubt them.

I’ve watched this happen to very senior people of ours. If there’s anything in the mish-mash like client expectations, that factors in. Why is the field that way, though?

Sam: Why do you think it is that way?

Kenzi: Because as much as the 10X stuff is nonsense, at the end of the day if you’re engineering large solutions, all of their things being equal and you’re in a capitalist system, it is a better value to employ a senior if you’re looking at your productivity. A senior who is barely twice as expensive as a junior for engineering licenses and scales is going to be significantly more than twice as productive.

There are costs on your company towards culture and sustainability and how you build something of scale. But when you’re at the tiny scale of I hire one person, hire the most expensive person you can.

Charles: I have to ask because you keep saying sustainability but I’m not sure what you mean by that. I’ve heard several people talk about different things there.

Kenzi: I meant when I mentioned that there’s a big difference between yeah I’m hiring one engineer trying to build a system that is in my budget and I need to worry about when I’m hiring 100 engineers. The long term life of a non, not just a startup who just has to make—if you’re trying to build a company over long term, then you have to start worrying over your own internal funnel and what happens with fluctuations in the market of hiring and what happens when you are losing count because of any number or cultural reasons. I do think to build a starter company if you don’t fall into somebody’s traps.

Jessica: As a larger company, you don’t want all your knowledge in only a few people because that’s risky?

Kenzi: Because it’s risky, because it limits who you can hire which puts you at a disadvantage on hiring, because when you have a gap between 10+years people and six month people, you don’t even remember how to train them up off it anymore. If you’re in a field that confuses quarterbacks and coaches as I like to call it where we’re like who needs management, who needs to know about mentorship, you are a tech lead therefore you know how to train people. You have this really bad problem training them up and now all of a sudden not only is it your economically optimal choice to hire the senior, it’s the only person you can hire.

If you’re running a capacity of management now, you don’t have the management overhead to bring on and train up juniors—if your company is growing because it needs more engineering to get more features done which means it’s managing to keep itself running, now it doesn’t have the room for change without master reorganization to be like it’s graphed on. How a bunch of people that don’t yet operate quite the same way that we have to train, it takes a cost to bring anyone up to a certain level of training. Training and education takes time. You have to have people that will spend the time doing that.

A small percentage of people as juniors throw their problems with absolutely no help and given the impossible requirements will succeed. Many of us in the field are people who did that, that is one of the solutions that don’t work in mass. Too often, we try to look at hey, this person did it, therefore that’s what you should. That’s not very scalable.

Sam: Yeah, the clip that I saw on Twitter recently was when successful people give advice for what this person say they hear is here are the lottery numbers, they worked for me.

Kenzi: It’s all lottery ticket thinking. Look at polygrams spending years telling us that the reason you’re successful was list. Yes, being able to make the technical choices he wanted allowed him to be productive was part of what made him successful. Replicating his choices at a different time as a different person obviously doesn’t have the same results.

Every person I’ve talked to has been successful has had a mix of useful advice and lottery ticket thinking they didn’t notice. Even when they operate similar businesses, I’m like oh, you’re faking this and figuring out the same as anyone else. Now, some of how the things you did or codified into your self story about why you’re successful.

Charles: How do we get around this then? I think we see the problem but is there a solution, are we still figuring it out?

Kenzi: I think some companies have done no problem. As a consultant, I see all the worst failure cases often because I’m brought in.

Sam: You get to pick up the pieces.

Charles: Right.

Kenzi: Sometimes, the best case is, “Hey, we’re really well organized. We just need some more engineering help.” Some small fraction of the time, that is utterly true and they’re growing fast and they just need to sift their own mental muscles and stuff. Usually, the problem is, “Hey, we have a C-level problem which filtered down to a strategy problem which is affecting our hiring and our retention which means we need more people.” Rarely is, “We can’t hire enough people, not actually because of something else wrong.”

I’ve talked to someone who had an 80 person engineering team that no single method of the engineering thing was hired from outside, they were all trained internally. There are downsides to that. Your engineering culture has too few inputs of other range of experience but they were successful and productive at what they did. Everything is trade offs, my point being though to them it was just since their whole team came up separate from the rest of the culture, we’re probably more used to startups than other Ruby and etcetera land. It just didn’t seem like an odd thing to them that they would’ve trained all their seniors up from ground zero as doing something else.

But yeah, you build a company that has a wide range of experiences and build in a cold drawn mentorship and training. These are things we do anyways, we just can’t, as often as I would like, hire a wide range of people via hire more juniors. At a product company even more so, if you can get out of what do I need to do this quarter thinking, your culture of hiring and every other way of everyone being happy there is better off for the university which includes experience and range of years in the field and every other university you can think of. There’s just enough studies on you will make more profit in less time with increased diversity because your team will be more creative. The people who can shoot for that as a goal for no other reason but it’s also been a hired advantage, people pick up talent that other people aren’t.

How would you get out of some of those traps? It’s similar to the problem with becoming an engineer, becoming a manager. If you were your best engineer and then you become a manager, for some period of time everyone else is incompetent in your head because in technical competence, they haven’t acquired some of the skills you had. We valorize competence such anything that registers off into engineering as competent as a problem to be routed around. Humans are humans and there’s greater things and you have not done your part in training other people to replace you, probably.

Sam: And you haven’t even figured out what your job is likely.

Kenzi: Yes, and so how do you manage then with people that will solve things in a different way that might actually be a better way but to you it will register as not how you used to solve that. Yeah, you need to build and acquire your company, sort of difference of opinion and collaboration and diversity and mentorship and room for good management in general, room for making mistakes and having to build back and build a culture of trust.

All of your problems with hiring and diversity go away if you make your company run great in a way that everyone will like.

Charles: Yeah, but that feels like a little bit of a pipe dream as having a company that everyone will like to work in.

Kenzi: Not everyone that works at your company already. The thing is the people you can’t hire are canaries. In your company, you can get by because of whatever reasons got you there. You may not know some other problems because they don’t affect you. Whoever is having a hard time making it in your company whether it’s the junior or the big problem everyone talked about lately is gender and racial diversity, all of these things. The things that are impacting them are often impacting everyone else. Other people just are pushing it off just to not notice it.

It’s not like improving your company is a negative. Yes, it’s a time trade off, what can you do? My take is usually hey, take a bunch of steps to make your company better in every way and you’ll naturally have a better pool of candidates which will naturally have a wider range of diversity. When they line the recitals for violins, gender went to 50/50 for first chair.

Charles: The advice to make your company better in every way, it just seems like it’s a little bit hard to know, what do you mean in every way? Where do I start? Are there specific things I can do that are going to make it better?

At the same time, let’s say that I have this problem. Let’s say that I’m sitting in a company and I’m thinking to myself I need more people. Maybe it’s I need more senior people, I’m right in the middle of this trap. Then, I’m trying to figure out what do I do now? How do I improve the company so that I can attract more people, how do I determine whether or not I can bring in new people, how do I decide who to bring in, how do I decide to reach these people? There are a lot of things that it feels like we’re talking about the problem but we’re not talking about specific solutions that somebody can go and implement in the company they’re at so that they can actually solve some of these issues.

Jessica: I think Kenzi just said that a place to look for the problem is with the people you can’t hire and with people who have left or people who are there and not happy. If you can make those people happy, recruitment problems just go away to something great.

Kenzi: Basically, find your leaky feedback. I have a problem with this in my company and we’ve fixed it as much as I can and everyone does. There are feedbacks, you’re constantly as a manager working on a brew. There’s feedback you’re not getting, there’s something someone in your company isn’t comfortable telling you. There’s a reason someone’s leaving and you didn’t quite discern the full scope of. Every source of information you’re not picking up from is probably something you can improve. You have to prioritize, you can’t do everything at the same time. Part of the job of management is there’s too much to do. But if you’re at the point of worrying about growing your company and hiring, your priorities about retention should dwarf that.

We took a couple years off to work somewhere else. A couple of people who have been with me have been with me for 13 years now, some variation of this company. There are some great benefits with working with people that long. If you can give people opportunity for growth and solve a bunch of these things, even in this field, your typical two year term rate goes down a lot.

Jessica: Also, the part with the studies that show that the more diverse companies do more and make more money, some of that is likely the causation of when your company is an awesome place to work, both people are more diverse and they get more done. Not only are you keeping people, but you’re making everyone more productive at the same time when people have that psychological safety.

Sam: That translates into better recruitment too because I personally maintain a list of companies that have done awesome pro-diversity things on the theory that if I ever find myself needing a job, I’m going to check what’s up first.

Charles: What I’m interested in from what Jessica said is that is diversity caused to getting more done and making more money or is having an awesome company a cause of both?

Kenzi: I think they’re probably both. I think I would have to go double check in the research, I think there is some evidence for the diversity of itself because there is some suspicion that it has to do with the creativity of aligning more viewpoints. I have discovered over time why Polygram suggests hire clones essentially. You’re just different in your roles and otherwise have similar backgrounds. The saying about if you want to go fast, go alone and if you want to go far, go with others. I joke if you want to go kind of far really fast, go with clones.

It’s a management cost. Collaboration is a trade off, it is a cost. It’s easy to make a decision that everyone agrees on and you’re losing information and creativity takes time and energy. When you’re in a business, it’s all trade offs.

Charles: I can tell you when I asked the question it felt like it’s probably both. There’s probably evidence to support that diversity contributes to productivity and there’s also probably evidence to support that having a great place to work contributes to both.

Jessica: Here’s a causal one. If you have a more diverse group, then people are more likely to talk about the things that are different about them and their different experiences whereas if you have a group with a lot of people with a lot in common, they tend to emphasize those commonalities in their conversations and not the differences.

Kenzi: If you’re looking for different opinions or missing information that you can act on, it can be hard emotionally but you got to treasure every bit of information you can get about how things could be better in your company. It takes work to get that culture anyways.

Charles: But how do you do that? How do you get people to the point where they’re going to tell you how you could make things better in your company?

Kenzi: There are books on management, questions that counter range things, the down sides of open door only, being helpful to people that know you well and trust you. There’s a whole field of management that we ignore in our field right there. We all need to go take more management classes.

In short, the culture, by example, by sharing openly and setting an example and try and create a culture by example that accepts feedback and makes people feel valued. It’s very easy to accidentally shoot down feedback and then not notice that you just lost a whole bunch of information and then your relationship. Much less when there’s the power dynamic of management.

Charles: I just did a training for Toast Masters Club Officers and we were talking about values and leadership. I think that’s what this comes down to in a lot of ways is that you recognize that you value those things, you value diversity, you value the feedback, you value that people communicate with you. You find ways to enact that. You go out of your way to demonstrate that you have that and then you teach the people that maybe are below you to have that same sort of open empathy for everybody else and you create the culture that way.

Sam: Yeah, you model the behavior and you make sure that you are not inadvertently incentivizing the wrong thing. You say you value a culture where everybody goes home but then you promote the person who stays late, as for instance.

Charles: Or you stay late.

Sam: Right.

Kenzi: That’s the hardest one as a manager. I do allow for some degree between as a business owner and a manager, there’s going to be different work loads. The issue there is to be competitive is sometimes required. I think you’re creative, if you’re not more creative, then you don’t overdo it and then it does limit then who can step into the manager with that available anytime.

Part of my problem is that this is all trade offs. People talk like do this, and this happens. You’re like it’s part of being an engineer, you learn where all the tradeoffs are. The encapsulation is great, it also has a cost. Doing it that other way that’s quick and easy is the other alternative, it also has a cost.

Charles: Life is that way, right?

Jessica: It totally is.

Charles: I didn’t take the time to exercise, I gained weight. I didn’t take the time to plan to eat right, I gained weight. You made that trade off.

Jessica: Also, the tradeoff that’s going to work for you, the strategy, depends on where you are and your context. If right now what you need is more encapsulation, then that’s going to be awesome. At that next job, it might not be. It’s like I had this iron supplement and one time I was low on iron. I took this iron supplement and it was awesome, I felt so much better. You could read reviews of various vitamin supplements, this is the best thing, it totally gave me more energy, everyone should take this. No, everyone who’s low on iron should take this.

Kenzi: Yeah, exactly. Experience helps the managers, so your first time around is the hardest time. I don’t know if we set up the culture where the managers go and learn more. I think part of the problem is one of the diversities we really are bad about in this field is age. Particularly in the Bay Area, it’s a super agues field. Therefore, there’s a certain cap on the level of experience. There’s a whole range of experiences that would be useful for some of these problems that we’re sometimes not even hearing.

I run a company, we’re not perfect at any of these. Our management woman led and design team is more balanced, but these are not easy things. Particularly when you’re a smaller company, often you end up hiring your friends and that has costs also. I do not come at these sort of problems from a whole than that sort of place but hey, we’re all human, we’re all doing the best we can, we’re making tradeoffs as business owners and we’re trying to maximize the success of our company and the long term health of the people we work with.

Sam: If I can go back to something a little bit earlier, you mentioned companies that are run by clones, people that are clones of each other versus companies that are more diverse and therefore also more welcoming. I feel like I really want to work in the more diverse kind of company but I often find myself in a company with much more of a mono culture, they have established engineering practices, their demographics are totally representative of programming overall.

I feel like if I’m in one of those companies, I want to figure out how I can do everything I can to move us towards the other kind. Personally, I lack very effective strategies for doing that so I’m wondering if there are any that you can share.

Kenzi: It’s easier to burn everything down and start over. It’s a really—

Sam: So I should quit is what you’re saying?

Kenzi: No, it’s a really hard problem. Go back in time and found the company more diversely. Borrowing that. You just fight, you read up on it, you widen the pool of the network of people who you’re reading, you read up on hiring practices as we were talking about earlier, about blinding resumes. You try to look at the biases of the social groups you hang in and how that affects the candidates you’re bringing in as you try to diversify that.

You do what I used to do, a lot of which you get really involved in the pipeline effort both because you believe in it and because you want a company that believes in those same values. You just try to find some people who are willing to be those challenging first couple of people that are in that company willing to put up with the cost of helping fix the culture by being the first at whatever class. It’s a very hard role, you treasure how hard that role is and give that person room to grow and account for that. That’s a thing where you might be better off talking to someone who has made that large change.

Charles: It feels like a lot of the things you’re talking about though are still general strategies; read more management books, talk to people who have done it before. Are there specific, just basic first steps that are really clear that you can partake?

Kenzi: Go get involved in mentorship. These are very specific things. Broaden the pool of who you listened to on Twitter. You can amazingly transform your experience of the news input by unfollowing everyone and following people based on a different set of things. Friends go through the experience of unfollow everyone and only follow women in their field. Follow a lot more black Twitter and you’ll get a different range of experiences.

Twitter is an incredible thing for showing the input, how radically you can change, the media inputs you take in with little effort, look at what group you socialize professionally in and notice where it’s a monoculture and figure out where are ways to fix that. Can you make your group more inclusive, can you go find yourself in more diverse spaces? Everything I said might be a piece of a much larger thing but they are actual things you can do because I know you have done a bunch of them.

Charles: I think where my disconnect was though is you’re talking about go diversify the people that you are listening to or talking to. For me it’s like okay, well, how? It’s not obvious to me how to do that. Then, you’re saying unfollow some of the people you’re following on Twitter and then follow people using a different criteria. It’s like oh, okay, now I get it. In a lot of cases, there are blind spots there that people just don’t see.

Kenzi: Yup, we don’t see them, and that’s the reason you have to go do the Harvard implicit study, learn what your biases are and realize… Just study everything. Go read up. If someone does an analysis of the voices in this that the women will have spoken a significantly smaller percentage for the same equivalent by most of the attendees feeling like the same amount of time. If women speak 30% of the time, people feel like it’s equal. If they speak 50% of the time, people feel like the women spoke way more. We all have these biases because we live in a culture where they’ve been programmed in and we have to learn them and start unpacking them.

That’s a personal journey, obviously, but it is one that reflects on your work and factors in on so many ways because we live in a field with such bad boundaries between personal and professional, because we live integrated lives, we’re friends with the people we work with. We want to have this life where it’s all but it means that if most of your friends are white, you’re going to mostly hire white people. Enterprise companies tend to do better than the startups base in diversity because they have practices around this, they require open listings, they have certain ways that avoid the tendency in smaller companies and particularly startups based who just hire all your friends.

Being a long time Ruby, I know it’s a thing many of us did. If you’ve been doing Ruby for a long time, you used to know everyone else that did it so therefore by definition you were hiring seniors, you would be hiring your friends which excluded masses of people. Since it’s gotten popular over the years, it definitely broadened the applicant pool so much that no, of course we don’t all know each other anymore.

Sam: Just going back to one tiny simple thing that you can do to diversify your Twitter feed and get some new information that you may not have if you’re a white dude in tech is follow Marko Rogers. He’s @polotek on Twitter. You got to follow him and more importantly read and try to listen and understand what he’s trying to say. He tweets a lot of stuff about tech and also black culture and how those things intersect. If you had to follow just one person, that’s the person I’d point to.

Kenzi: Also, when we do this, don’t turn these people into just teaching moments for white people or women or men. Particularly when we decide we need to dive into this course without having to follow a bunch of it, there’s often moments where we’re starting to learn where we’re like oh thank you, I learned so much, and you step on that one.

Broaden the number of inputs for decision making. That’s sort of the core bit of that whole thing. Read the people you really don’t like. Just like you sometimes read what Republicans are saying if you’re a Democrat and vice versa. If some of the angry internet feminists they were as people put it, bug you, read them. Try to understand where they’re coming from and why. You don’t have to agree with it, but sometimes there’s reasons for some of that stuff.

Jessica: If someone’s experiences don’t match yours, that doesn’t make them wrong, it makes them information.

Kenzi: Yeah, exactly.

One of the things given the demographics of the field if you decide that it is wise to diversify your company, picking the engineer in the field, you’re going to have to figure out than how to train up juniors. At this point if you say you want to work on gender stuff, if you only hire senior women you are shuffling around where they work and how much money they get perhaps. It is not fundamentally changing the balance in the field. It’s a little zero some. For the sake of the company obviously maybe you care a little less, but it’s still just a smaller pool and competitive.

A lot of companies tackle this by hiring juniors. I can’t remember who it was but some company who was really proud of having fixed their gender diversity stuff because they fixed their interviewing that allowed them to hire up a number of junior women and then two years later lost them all and then complained about the losing of juniors. That retention I think is a much bigger problem than the pipeline, that’s a whole other podcast though.

Charles: It’s true but when we get into this, I have people contact me. “Well, you have a podcast? You probably know a whole bunch of people and we’re trying to hire senior developers.” I said well, have you thought about training junior developers? What they say is after a year or so, they’re all going to leave anyway.

Jessica: Maybe that says something about you. Almost everybody.

Kenzi: That’s what I’m getting too. There’s a case study, they actually got more than a year out of them but you have to remember that from the difference between someone with no field experience and a year experience is not a $10,000 raise. You’ve trapped in your head, “Hey, I’ve invested this into you and I think you’re worth this much.” Through some training investment you put in and maybe it’s loyalty, maybe it doesn’t, you have made them incredibly more valuable.

You’ve set up a situation of you do not promote them and stop thinking of them as, “Oh, that junior we just hired,” for it to be impossible for them to keep working at your company because why would they be able to afford to turn down a 30% raise when they were probably not affording to live in the city you hired them to live in because you hired them as a junior. I’ve seen enough of the junior salaries. Juniors in San Francisco are often scraping by. They are investing in themselves and hey, if I get a couple years in this field, I will be far better off. Either they wanted to, sometimes they literally can’t hang around and turn around this better offer.

It turns out if you promote them and make a path, the middle career path is where it gets hard anyways. If you make a path of advancement and give them a road and give them promotions of what they would do otherwise, they’re a lot less likely to leave.

Charles: I completely agree. In fact, it usually prompts me to say something that’s rather unsympathetic that boils down to well then pay them what they’re worth so they won’t leave.

Kenzi: They’re stuck in your head as a certain position and it’s hard to break loose of those assumptions.

Jessica: Also if you hire a whole bunch of women as juniors in order to balance your diversity, then you’re increasing the women as beginners through and it’s hard for any of those women to be considered senior because they’re women.

Kenzi: I was going to get around to all of the things that go wrong with this. The common I’m thinking of simultaneously is considering all the women. They hired juniors and not giving them an advancement track, replace the woman founder with her co-founder, her husband is the CEO which was probably bad signal at a time some of these cultural things were going on and so they lost the all to GitHub.

Charles: I think it’s interesting that you bring that up because you’ve implied it probably wasn’t the right move. It could’ve been the right move if the fallout, the message you sent whether it was the right move was not the message you wanted to send.

Kenzi: Well, I would also say the follow through. It’s a catch 22. If you’re going down this road and then you failed to follow through—on the other hand, here’s some people that got their first good job and bootstrapped into that. If you were nice enough about it, it might speak well of you. Usually in my experience if you give someone opportunities and they speak poorly of you, you really screwed things up thoroughly over time.

Even if someone decides they can’t take this new opportunity, usually they’ll be super happy and refer you as an employer forever down the road. If they’re bitter about it, wow did you fail to gather some signals about what was going on.

Charles: I think that’s really, really true.

Kenzi: I’m thrilled when someone goes onto another opportunity that’s a different thing that they’re doing that they get to explore stuff and maybe they’ll come back to work for us in a couple of years, maybe they’ll be somewhere else in reverse. We are a friendly field, as I said there’s cost to that. Particularly in the Bay Area, I’ve had people who were boss who later became a client who later became an employee. It’s a very small town and you should treat everyone very well and see how it works out when it comes around.

I don’t think that they made the mistake of trying to—I think they only hired people as juniors, that might be a problem. I think if they improved their bad filters on who they can hire and train and therefore increase their diversity and have the follow through and culture make good use of those people, it would’ve been a much different story. It wasn’t doomed to go down that road.

That’s my issue when people don’t realize why they’re losing the people they are. You don’t say canaries are annoying, they always die. When you’re a canary, the gold mine keeps dying. That’s kind of what we do in our field. “Yeah, I can’t afford canaries, they keep dying. I’d spent all this money and they don’t last.” It’s supposed to be a signal that you can fix stuff.

Charles: Not only that but if your canaries keep dying, you may want to look at why your miners keep dying too.

Kenzi: It will take longer often but eventually you sometimes will lose people in a giant swamp because the people that took longer noticed that they didn’t like how things were going. Sometimes tend to get really all frustrated all at once. Take the signal and improve your culture. It’s wonderful to have people so excited to work with you that they refer other people to work for you. It does radically change your recruitment game.

Charles: Yeah, I’d also point out that if they all leave at once, I have to say that it’s been pretty rare when I worked at a company where they weren’t one or two people that left. More than one or two people left at the same time. They didn’t all talk to each other, they weren’t all friends in the whole company except for maybe management didn’t know why they were leaving.

Kenzi: There’s a whole sorts of problems with that. If you think it’s expensive losing junior people, lose senior people that are the backbone of your company where all of the things work how they work. A company, its employees really are the best, most valuable part of the company. I’m always sad when someone resigns or moves on at the same time being excited for them. Multiple at a time would be rough.

Charles: Sam, do you have some picks for us?

Sam: I just have one pick today and that is Mandy Moore. As some listeners know, Mandy has been editing and coordinating the show since sometime in the first year, is that right Chuck?

Charles: It was right around six months in.

Sam: Oh yeah, quite a long time. Basically, she’s been making the Rogues all sound considerably smarter than we probably deserve to. Anyway, Chuck has recently switched to a different company for that stuff which means, listeners, that Mandy has some extra capacity. She does podcasts and screencast production as well as the usual virtual assistant work, event organization, and research and so on. You can check her out at

Charles: I’m just going to plus one that, Mandy has been terrific. There were some things that I had to figure out both financially and business wise that made me switch but it wasn’t anything that Mandy did, it was actually just where I was at and what it was going to take to keep the podcast going. I definitely recommend Mandy and I’m just going to reiterate, if you need any kind of virtual assistant, podcast editing, anything like that. She does a terrific job.

Jessica: I got a good book in the mail the other day. I don’t know who bought it for me, whether it was a gift from another person or from past me. I have Caroline Yoachim’s Seven Wonders of a What’s In Future World. It’s short sci-fi or fantasy, it’s just short stories. Each of them is super condensed, world building. Since my favorite part of all the sci-fi fantasy books is the world building, I get bored with the sequels really fast. This is awesome. Lots of worlds in just a few pages.

Charles: Nice. I’ve got a couple of things to pick here. The first one is we got a foreign exchange student last week. It has been a ton of fun. If you’re thinking about it, trying to figure out if that’s something for you, we’ve had a lot of fun. We got a 17 year old girl from Italy. It’s kind of fun for me because I lived in Italy for two years but it’s also fun for the kids, they’ve had a good time just playing with her, playing games with her. She’s also met some of the neighbor teenagers because my oldest is ten. She’s been enjoying a lot of that as well. If you’re looking for something that adds a little bit of interest and fun to your life, then definitely check that out.

Kenzi: Since sci-fi came up, I always like plugging Octavia Butler’s, one of my favorite sci-fi authors, particularly if you wanna get something a little outside of the same male viewpoint that you often do.

Black Girls Code, one of my favorite programs you can donate to. Obviously, since Andrei works for us, we also like Ruby together. If you wanted to donate and give back to the infrastructure and work that goes into making the Rails apps, we’ll use work. I think those are my picks!

Charles: Awesome. If people want to know more about Cloud City or anything else you’re involved in, what should they do?

Kenzi: They should look at our website and learn more or they can send me an email at or find us on Twitter @ClouCityio or just me @KNZCONNOR.

Charles: Alright, thank you for coming. This was a lot of fun.

Kenzi: Thanks for having me!

Charles: We’ll catch you all next week.

Sam: Happy Hacking!