Coaching New Managers, with Tiffany Conroy

Ep 16

Sep 20, 2023 • 55 min
Tiffany Conroy, former VP of Engineering at SoundCloud, shares what she’s learned about where new engineering managers stumble and how to support them, considering whether you want to be a manager at all, the value of explicitly asking those around you what success means, the power of having the confidence to say “I don’t know”, coaching managers through their first case of underperformance, how rigid role definitions hold back folks that perform both product and engineering work, the power of the Six Thinking Hats for making intense decisions, and the cultural responsibilities of senior leadership.

Allen: Welcome to It Shipped That Way, where we talk to product leaders about the lessons they’ve learned helping build great products and teams. I’m Allen Pike. Today’s interview is with Tiffany Conroy. Tiffany worked at SoundCloud for many years, spending time in product design and engineering roles up to being the VP of engineering and is now a professional coach and trainer for engineering managers. Welcome, Tiffany.

Tiffany: Hey, thank you. Want to clarify that I was a VP of engineering. There’s multiple VPs of engineering, but I think that’s one of the challenges we get with these titles. It’s like, are you the head of engineering or a head of engineering? Anyway, don’t want to overinflate my contribution.

Allen: I appreciate the humility and also, I’ve become fascinated in having all these conversations with people who’ve been in these leadership roles in different companies. All the various interesting decisions that orgs make about titles, exactly to your point, that are like, we have multiple heads of engineering, what does head mean? I’m like, head of engineering is two layers before senior executive VP of engineering, which is actually still only for this one part of the engineering org.

Tiffany: What is the job that you’re doing? Are you looking after an entire department? Are you running the entire location, or do you have half a dozen managers? What is the job? Anyway, just clarifying was not the VP of engineering. I was a VP of engineering.

Allen: Excellent. Well, it’s awesome to have you on the show. We’ve met many years ago back in the conference world and it’s fun to be back talking and having a chance to go more in depth than you can in five minutes in between sessions at a conference.

Tiffany: Indeed, yeah.

Allen: So before we get into certain some of the topics, we want to talk about engineering leadership and some of the things people learning. You’ve been getting some great time talking to new managers and working through some of the things that they’ve been learning, which I think be interesting to the folks who listen who are either new managers or maybe are often coaching new managers depending on where you are in your path. How do you like to summarize your path in a soundbite sort of way in terms of the Tiffany story so far?

Tiffany: The Tiffany story so far is I graduated with an electrical engineering degree. I guess maybe before that, I was this creative artistic person who was good at math and I thought, how can I combine these things or which one should I pick? And I went to this event where they said that engineering, whatever that meant, was the place to go. So I got bought into this idea that engineering is a creatively applying sciences, whether you believe that or not.

Allen: It depends how you go about it.

Tiffany: Yeah, sure. I graduated into the dot-com bust and the area that I’d studied, which was photonics fiber optics, was the wired internet and the wired internet tanking, I don’t know, if you’re Canadian, you might remember that Nortel.

Allen: Oh, yeah.

Tiffany: Was a part of that whole thing. I didn’t have a job, so I became this self-taught web developer who then through various paths, ended up really digging into that and really enjoying that in a way that I had not expected. And then about 15 years ago, I decided to accept an offer to come to Berlin to work at a small web agency. I worked at that web agency for three years and then I followed a colleague to SoundCloud and I was there for 11 years and I had this kind of mixed design and UX. At the time, I didn’t know what to call it. I don’t even know what we called it at the time. But anyway, I was doing design and front-end at SoundCloud and entered into a company where there were a lot of different things to do. And for someone like me with a sort of multifacet skillset, was constantly reinventing my role and finding what was the most relevant thing for me to do. And I contributed to a lot of behind the scenes things at SoundCloud and then I moved into management. And I moved into management at a time when there were not a lot of people around. There was a post layoff and they were like, “Who’s a competent person? Who’s left?” And so then I moved into management and really started to understand how to amplify my own contribution through engineering management as it’s done at SoundCloud and then moved up through the ranks and then eventually joined the engineering leadership team as a VP of engineering reporting to the head of engineering. And I did that for a couple years before I decided to take a break after a decade and try and become a full-time trainer consultant coach and have been doing that for about a year with some success. And yeah, that’s the path to where I am here.

Allen: Yeah, I’ve seen a number of people make really nice paths where basically you get to the point where you’re like, okay, this is a lot. I’ve done a lot, I’ve learned a lot. Maybe I’m going to go spend some time sharing that. What I’ve learned is some of the things that I’ve learned with the world, which can be a nice change of pace.

Tiffany: I’ve actually been having multiple conversations. So how much do I want to pursue coaching versus consulting versus going back into doing kind of leadership? And I’ve been looking at LinkedIn and reaching out to various people and talking to people who have been doing this coaching thing and really, I feel like so many people are a coach or a facilitator or some of these roles and I look around and I’m like, is it the age that I’m at that I’ve reached this teacherly advisor role, or who’s doing the work? We’re all coaches, who’s doing the work?

Allen: We’re all a whole cohort of coaches.

Tiffany: So that’s something. Or is it where you see the same thing once you notice it the first time? I’m just seeing it everywhere.

Allen: I think my instinct, and I’ve noticed the same thing, is that it’s half that and probably a thing that people massively under count, and I’m sure you’re doing this and I do it too, is you pay attention to and you surround yourself and you put your mind on people who are achieving things that you aspire to and that do great work and that you look up to and that you’re inspired by. And so when you think of “everyone is a coach” and coaching for Fortune 500s or whatever you think everyone is doing, it’s like is everyone doing that or is the 0.01% of highly talented people that you’ve sought out to meet at conferences and that you’ve invited to travel the world to talk with give talks or whatever the things that why “you know everyone that we know” or that you follow the on social media or whatever 0.1% of those people are doing that, and then the 99% of people. So we compare ourselves of course not to the 99%, but I do the show and talk to a whole bunch of people who are way more experienced and talented than me that have all this great knowledge and I feel like, oh, I am this random and everyone else is so much more successful. It’s like, well, I try to sometimes remind myself, I’m purposely seeking out people.

Tiffany: Yeah. Okay, I’ll put it that way. I mean, I have been seeking out those people and asking them what has their journey been and what advice might they have, that kind of thing. But I do feel like, yeah, who’s doing the work? But maybe it’s an anxiety actually of, is this something that there’s demand for if I’m just one of many more people doing it? That’s maybe also part of the question I have.

Allen: It’s an interesting time in our industry also where I think most people have at least in the back of their mind being like, all right, okay, what is their demand for where is my skills? How do they compare to… It’s not 2021 anymore, but what is 2025 going to look like, is the question we’re all asking. Talking about this, the work that you’ve been doing where you’re doing coaching and facilitation and some leadership and contracting and stuff like that, but one of the things that you’ve been doing this training and we’re working with new managers in this role that you’re in now, but also obviously working your way up through layers of engineering management to being VP, you’re also working with managers and new managers and helping people on that journey where they’re like, okay, I’m trying to be an engineering manager, which is infamously a difficult transition. What are some of the biggest barriers, blocks, challenges that you’re seeing new managers, at least new engineering managers stumble on?

Tiffany: So I think the main one that I think is classic and everybody goes through, and I went through this myself, which is do I want to do this job of engineering manager? Somebody probably has suggested that you do it. There are also people who are like, I want to do this thing engineering manager and it’s sometimes unclear what their motivations are, but money. But there are these people who have been encouraged to be engineering manager like myself or one is needed and they’re kind of suggested that they do this. People are like, I don’t know if I want to do this job. And the reason I think they don’t know if they want to do this job is they don’t know what it entails. They’ve got very few examples of what is the work look like? It’s what they’ve seen their manager chain do or maybe some adjacent people around them. It’s a lot of stuff behind closed doors. You don’t watch how a one-on-one works. You don’t see necessarily the back door of the promotion panel unless your company has a forum for that. But there’s a lot of activities that are happening that you don’t get access to so you don’t know if it’s a job you want to do. And because you don’t know what the job is, you also don’t know how good am I at it? Am I doing it? Am I even doing it? What’s doing it mean? So I think there’s a lot of that at the beginning. And so what I’ve found that new managers really need is a lot of times, just reassurance that that sounds normal. What you’re describing is pretty typical. Or the other avenue that I give people is, and I give this generally not just to new managers, is who around you is going to judge that you are successful? Who’s making that judgment? Is it your manager? Is it a peer? Is it yourself depending on how you’re doing things? Who’s making the judgment of what success is? And be very explicit about asking them what success means. And the other side of that is telling somebody what you expect of them, but if you are sitting there wondering, am I doing a good job or what is my job, is you can just ask people around you, what do you expect of me?

Allen: I like that point about expectations and actually polling for them. I see a lot of people polling for, am I doing a good job? And then they get, yep, you’re doing a good job. And then they’re like, hmm, okay. But then inside their head they’re like, I still don’t fully understand why. And so of course ideally as a manager of managers, you’re saying you’re doing a good job because of these reasons and this is the growth that I’m seeing. And ideally all that happens, but sometimes you think you’ve said that and then the person doesn’t absorb it or maybe you just are busy and you haven’t fully communicated why they’re doing a good job. And so that being like, okay, if I’m doing a good job, why or what does a good job… What would an even better job look like? Obviously these are things you want to assume that you’re having these conversations with everybody that you’re working with, but what does improvement over the next year look like? All those sort of questions. And actually-

Tiffany: Yeah. I have this coachee, and I won’t get super specific to kind of keep their confidence, but they had a suggestion that they take on this management role. And one of the things they expressed was the PM was very excited that they had begun this role and they’re like, “I don’t know why this person’s excited.” And I was like, “Ask them.” So when I took this role, you said you were super excited to have an engineering manager here. What were you missing before? Why are you excited? Because they’ll just tell you and then you can decide whether you’re going to do that. It could be that the reason they’re excited is completely outside of what should be expected, but that’s a conversation you want to have. And I think people are just really afraid to admit that they don’t know the answers to those things.

Allen: Yes, that’s such a huge thing and I tend to see it happen more in larger orgs.

Tiffany: Interesting.

Allen: And the larger the org gets, the more there’s a bit of a feeling. Well, because the bigger the company that gets, the more stuff you don’t know because if there’s a 1,000 people or 10,000 or a 100,000 people in the company, then you don’t know 99.9% of the things. And there’s a whole bunch of other people going around acting like they know the things. And so if you let on that you don’t know the things, then that’s maybe someone’s going to catch you as the one imposter among 99,999 other imposters.

Tiffany: This actually reminds me that I had been invited to do a talk a few years ago and I ended up doing it on confidence in the workplace and I drew a lot of my material from someone who had written a Medium post about it. And if you Google my name and confidence, you can find all the references. But in that talk, I talked about what are some of the benefits that confident people have in the workplace? And one of them is confident people are not afraid to say, I don’t know what that is because they know that them not knowing one or two pieces of information isn’t going to destroy their reputation, and they have the sort of freedom and relaxation to say, I don’t know what that is. I don’t know what that means. And of course this can be a very scary thing to say, but what I have found is that when you admit, oh, I don’t know what that means, people then understand that you’re understanding everything else. If you point out, oh, that acronym you used, I don’t know what it means, and that’s a very powerful way to get people to trust what you know when you’re super open about what you don’t know. If you are afraid of being vulnerable, no one has any idea whether you’re just faking everything. A similar vein is when you admit that you were wrong, it’s the same thing. That a confident person is able to confident that, oh yeah, last week I said the numbers were blah, but I’ve looked into it, it’s something else. And then what that tells the person that you’re talking to is, this person is going to come to me the minute that they get new information. And so I’m always going to be getting the best information that this person has from them, and I can just trust it for as long as this person doesn’t come back to me and correct it. And so these are all kinds of things that are tactics in the workplace that people have come to me and it’s like, oh, you’re so confident. I was like, I just have these behaviors that confident people have that then bring me all these benefits. But anyway, that was a digression from-

Allen: No, I mean, it’s part of it. It’s a part of all of it, right? Because a huge part of this change from individual contributor to manager, whether it’s engineering manager or any other kind, is that confidence gap where it’s like you’re now doing this job and that now it suddenly feels like, and in a lot of ways it is almost a completely different job that just because you were a good developer does not mean you can be a good engineering manager. And even if you’re eventually going to be a good engineering manager, you probably won’t be a good one in the first six to 12 months. So of course there’s going to be this confidence gap. And I think it speaks also to the trust building loop, which goes from something that’s like, yeah, you want to have trust of your team when you’re an individual contributor and then trust is the job kind of, in some ways as a manager and a manager of managers. And so these habits like admitting when you’re wrong and asking questions when you’re unclear and getting explicit and asking and even re-asking when you’re not sure exactly what expectations are, what people want from you, those all build trust. And then that’s hopefully part of where the confidence comes from. On this topic of stumbling box new managers, you mentioned one of the big classic ones, which is someone comes into the role and they’re like, ah, do I even want this role? Which is a good question to be asked. It’s probably better than the people that you mentioned. There’s that subset of people occasionally who are just like, I’m destined to be a manager, I should have power. And then you’re a little skeptical-

Tiffany: It’s a little bit of humility, it’s good.

Allen: So that’s a classic. Another one that I’ve seen before and I’m sure that you’ve seen before is a common, especially first six, 12, 18 months, a new manager is the first time that someone has to deal with under performance. They have someone who’s reporting to them, they think the person is not meeting expectations, but did I set the expectations right? Am I failing them? I must be failing ‘cause I’m a new manager and I probably suck. How do you tend to coach people through that experience?

Tiffany: I think the typical thing that I’ve seen people show is what you’ve described, which is they’re like, okay, this person’s underperforming. I haven’t set the right motivations, I haven’t made it clear how they need to perform. Clearly there’s something I failed to do. And in the cases where the person is really truly a poor performer, either due to their skill level or their motivation and attitude is it’s actually not recoverable often or can be not recoverable in those situations. And the manager, if they’re at all a caring person, wants to be sure. They don’t want to say like, ah, this person’s a poor performer, get them out of there. Or at least they’re not the kind of people who go for outside consultation on whether-

Allen: Yeah, for sure.

Tiffany: What they should be doing. And often it’s just that they don’t know how to get confident about that decision and they’ve never encountered it, so they don’t know what are the processes for how we’re going to get confident. They’ve never had to have that really hard conversation. And so yeah, I’ve had coachees come to me and they’re like, I’m looking for a coach. And then very early in the conversation, it turns out that you’re like, I’m having a hard time managing this one person. And the real issue is that they’re on a journey to decide to essentially confront that person with the situation and eventually they make a decision to end the working relationship, fire them basically, or convince them to quit. And so that then is, okay, what are the tactics for getting confident? How can you approach it? Those are the sorts of things that people do come to me for. And there’s sort of two types of underperformers that I’ve seen, and one of them is they’re done. They’re done or they’re not that interested or it’s not the technology choices they really are excited about, or for some reason they’re just not really into it and they haven’t made that decision or they’re afraid to make that decision or they’re looking for a job, they don’t want to tell you yet. And with those individuals, what I’ve seen work is people use the stay interview for people that are really interested in keeping. If you look up what is a stay interview, a stay of interview is you ask them, why do you stay here? Why do you like working here? People use the stay interview for that purpose for the people they really want to keep. But I actually have also found a stay interview to be useful to speak with a poor performer where you suspect that they’re just kind of done. You frame it as like, hey, I want to be the best manager that I can be. And maybe you’re doing a regular rotation of these stay interviews with everybody, but you focus on this person because you suspect there’s something there. And in those conversations, you can learn that they actually aren’t that interested in staying, and you kind of point this out to them and you kind of remind them and say, it’s okay. It’s okay if you’re done here, that is an acceptable thing. You don’t have to hold onto this. It’s not a failure. You can just go. And that can work. That can work as a way where people just say like, okay, I guess I’ll start looking. And pretty soon they resign. And that’s a way that you can, as a first time manager, proceed. The other option is that you find out that the person is just never going to get better. And in that case, very first thing you should do, and really the first thing you should do anytime if you’ve never encountered this in the work environment you’re in, is talk to HR about what the official policies are. And depending on your jurisdiction, the policies might be something more or less complicated or maybe the company has a policy. And what I’ve coached people into realizing is that it’s not just a formality. The HR policy is designed to get confident. Whatever their policy is, it’s a policy of being confident about the decision. So if they say the first course of action is that we write down all of the expectations and we put a date on it and get them to sign it, all of that is not just paperwork. It’s a procedure towards confidence. And so you don’t want to be really confident that you want to get rid of somebody and then find out-

Allen: And then start the process.

Tiffany: And then find out it’s a two-step process that takes multiple cycles. You’re way behind the game. And so those are kind of the two versions I’ve seen.

Allen: I think it’s interesting. It depends obviously a lot on the size of the company and the business and you’ll see very, very, very different conversations with a leader who’s a line manager at Microsoft and they’re like, ah, there’s somebody who I need to let go. So I’ve been working at through that, we’re about eight months in, I almost have the green light and you’re like, oh, no. And then sometimes you’ll talk to someone who works at a startup or whatever and they’re just like, yeah, I realized last week this person needed to go, so now they’re gone. And then you’re like, whoa. And it’s totally, totally different cultural expectations and whatever, and both policies and maturity and whatever. And so it’s really interesting seeing those paths. Obviously a new manager would never decide and click like that. Majority of the time a good manager is going to decide on the wanting to ask themselves over and over and over again and like, oh, how am I failing this person? And I’ve set these expectations and they really seem to be meeting them and they’re meeting some of them and they’re definitely trying harder. I am pretty sure they’re trying harder, but then now other problems have cracked up.

Tiffany: That is really hard. That is really hard when you’re seeing progress and then the progress plateaus or it doesn’t get as high as it needs to be. That, I think is also really hard. And something else that I’ve talked about with some other people is we are in this industry and I don’t know if it’s all kind of programming or engineering or whatever it is or if it’s somehow our specific industry, which is this idea that everyone has to be getting better all the time. And if they’re not getting better all the time, that they’re stagnating in a way that is not… They’re underperforming essentially. And as somebody who’s worked at a company where constant growth… When SoundCloud introduced values, one of the first batches of values was level up. We’re constantly leveling up, and that was a company value. Depending on the kind of company you’re in, you may not need to be constantly getting better. That’s a conversation you can also have, which is what you’re doing is fine. Your work is fine and you might not get promotions. And there are individuals who struggle with, they simultaneously want a promotion, but they’re also doing nothing to self-improve. And you’re like, they can’t.

Allen: You can pick one of these.

Tiffany: You can pick one of these. It’s okay that you’re doing acceptable work and it’s reliable most of the time. That is fine as long as you don’t keep wondering why you’re not promoted.

Allen: I think it’s an interesting point. I had never really been given too much critical thought to this common corporate culture, at least in technology, of that everybody should be growing and that we tend towards assuming not only that that’s the default, but that’s what success looks like, is that this growth. I think my instinct is that some of that just comes out of the fact in technology that everything we’re doing is getting outdated so rapidly that if we’re not growing eventually the company will just not, right?

Tiffany: You have to at the very least be changing what you know. How can you be the kind of person who keeps up and isn’t somehow also getting a little faster? You would have to be a special kind of person who’s capable of learning and changing but not also improving. It’s a weird…

Allen: And that kind of is improvement if it’s like, yeah, 10 years ago I was building a webpage using Plain HMO and CSS, and now I’m building a webpage, but now it uses 10,000 build tools and all these other things and it’s still a webpage, but have I gotten better? I still build webpages, although probably a lot more complicated and have more accessibility, and they’re actually probably better in a lot of ways. And so I have actually gotten better, but the bar of I’m a successful, what would’ve been called web designer and it’s now called front-end engineer or whatever it is, is actually increasing. And so I’m growing even if I’m still sort of meeting that bar. So I think that’s one kind of complicating factor in it. But I do like the idea of questioning some of these assumptions that are built into so many company cultures of growth and impact and stuff like that. And there’s a reason why most orgs tend to set themselves up that way, but sometimes it’s interesting to be like, is that everything? What are the limits to these?

Tiffany: So SoundCloud has… And I refer to them a lot because obviously I worked there for a decade. But at SoundCloud there are published engineering levels and you can Google SoundCloud engineering levels and find them, and there are descriptions of what behaviors are at the different levels. And a lot of companies have this, there’s a website, I forget the name of it, which has kind of a standard suggested what are levels. And it has to do often with the complexity of the work that you take on, the number of individuals that you are bringing along with you, the scope within the organization that your changes have. And you can be a really fantastic executor and you’re constantly on top of what is the best way of implementing things and still not good at breaking down work for other people. That’s just not a thing you’ve ever gotten good at. And so that is going to keep you at a level of impact because you can drive your own work really successfully, but you can’t drive anyone else’s work. This is where really larger companies need more complicated paths, where being an extremely excellent independent contributor, truly just what your contribution is is one path and one form of success separate from leading others, whether it’s people leading or technical leading. And at a company the size of SoundCloud, we just didn’t have that complexity. We needed people who were at these higher levels to be also doing technical leadership, not just high level execution, but I think you can go the other way around. You can go the other way around when you’re at a small company where these levels don’t matter, it just matters how great are you at getting the work done?

Allen: It is an interesting challenge. I see a lot of both people in roles as well as people in leadership and trying to set and improve and iterate the systems, how we level people and how we retain people and how we design our compensation and evaluation and all these sort of things. And you, I’m sure have a perspective on this ‘cause you talked a bit about how at SoundCloud, you had these mixed roles where you came in at some time, you are VP engineering, but you were doing some design, you’re doing some product, and you were kind of doing this small company thing that’s part of why small companies can sometimes outcompete much larger companies, is that people fill in gaps or they don’t necessarily have the title or the official training even or not every fully realizes that this person is doing both writing, marketing copy and writing C++. It’s like, we don’t have a job role for that, but they’re doing it and it’s great and they’re good at both. Or they could write the marketing copy that relates to the, I don’t know, other C++ developers that they’re marketing to or whatever the thing is. And so one of the things that I’ve seen as a huge challenge, and I’m curious what your take on it is, is that as organizations grow, there’s a huge gravity towards simplifying down the set of rules that they optimize for and the set of hats and the shape of… I worked at Apple when it was actually still much smaller than it is now, but I started as a person who was an engineer who also liked to do design and had product interests. And even at that scale that when there were, I don’t know, 10,000 people, 700,000 people, the organization was like, yeah, that’s not really a thing. Can you please just write code? Which not that there is zero people at Apple that write code and also have product influence, but certainly not very many new grads from university. So it’s a path that companies tend to go down. And I’m curious what your experience as someone who went from being in those mixed roles through to somebody who is then helping set how do we evaluate and compensate and measure and try to build equity and do all the sort of things that leads to these simplified ladders and structures, did that change your perspective on that or were you like, no, we still need to make sure we try to, as long as we can, support these multi hat wearing unicorns, for lack of a better word in our orgs?

Tiffany: Yeah, I think I know exactly what you’re referring to. And what I found as an individual person in my experience of being a design… I was on the design team, I was a product ,manager, I was a tech lead. I was developing all at the same time, was that I could relate to those roles a lot quicker than other people in my role. Or they had other superpowers I didn’t have, like trying to negotiate down our cloud costs and stuff. I mean, they had other skills that I didn’t have, but what it meant was that I was a really communicative partner with the product person or with the design team, or I could step in and hire for certain kinds of roles and do the hiring for it. So for me, it meant that it was how I related to my peers that became beneficial. For those individuals that are doing all of those activities, there was a transitionary period at SoundCloud where I had gone from just doing all my own thing to then going into one of these formalized positions and I got sort of slotted off onto one track when I was contributing in the other. And it was a real challenge because my title was product manager, but I was actually the tech lead. And when I say actually, I mean I was doing things that no product person would do. I was hands-on helping architect and writing code, but I was dropping a bunch of things that were considered important for product people to do, which I also thought was important to do, like certain types of monitoring of metrics and creating metrics and things. And I didn’t have time to do all of these things and I was really concerned that my title was product manager and I was being judged against some product manager metrics, but then I was contributing in this engineering way and this became this real challenge for me and it became this, not an anxiety, but I felt like I wasn’t performing the duty that they had given me this title of properly. I wasn’t doing the job they had told me to do because I was doing this other job which was desirable. And I remember this moment where I was in a room with my manager who was a product director, product lead, an adjacent engineering director and another kind of adjacent engineering director. And they were asking me if I would do some very specific surgical program, software engineering within inside the SoundCloud mothership. And for historical reasons, a lot of people knew these areas of the code and I knew them very well and they were like, “We have this really urgent task, we would like you to do it.” And I said, “I can do it. I will do it. I think I’m the best person to do it. I have the capacity to do it. I even have the time to do it. I need you to understand that my title is product manager and I will not be given any credit on paper for this work. I need you to all acknowledge that this is not product manager work, this is individual contributor engineering work and I’m the best person to do it.” And they all kind of seem confused in all their different ways. Why does this matter so much? And it mattered because I was paid 20K less than an engineer at my level, and I didn’t find that out at that moment, but I had this sense that I wasn’t being compensated for my contribution.

Allen: It’s even worse than that because your path to getting more compensation was probably to become a senior product manager, which probably was on some metrics about product management delivery reporting stuff, which are-

Tiffany: Which I wasn’t even interested in doing. So eventually, this was around the time that I made this jump over to engineering manager and then was always thought of as… It was really funny during this time when I was a product manager because all the people who were individual contributor engineers, they just thought I was an engineer because I was contributing to code all over the place. I was participating in incident response.

Allen: Ask you to review code.

Tiffany: And then they’d go to the HR system and be like, you’re a product manager? What? So that was a real challenge because when leveling was introduced, pay grades and everything was introduced and I was just on the wrong path and I was pretty resentful about it for a little while. I’m kind of over it now, obviously not that over it, I mentioned it, but I think that’s a real danger that can happen. That these people whose skills are highly valued and demands were made of me to… And by the way, I didn’t ask to be a product manager. I was given the title of product manager ‘cause I was doing product work, which at the time it didn’t matter because we didn’t have those systems. I think that’s a real danger if someone is not scanning to see, okay, as soon as we’ve introduced divergent compensation for different roles, who’s getting screwed? Who are we overlooking? And that got corrected and it took some pushing on my part, which then I think falls onto the next thing, which was that when I became a member of the engineering leadership team, when that was the transition, I had this realization that whatever I wanted from the corporation, from the company, whatever I expected the company to do on my behalf, that as a member of the engineering leadership team, I was now one of those people delivering whatever it is I expected as an individual contributor. Do you see what I mean?

Allen: Yeah, you were one of the people around the table who would be surprised if somebody came in and didn’t want to do a thing that didn’t fit or whatever. You have the opportunity to either be the surprised one or be like, oh, I understand. I’ll help.

Tiffany: Whatever. I was like, why didn’t anyone ever notice or why didn’t anyone ever approach me? Or how did this happen? I had this realization that I was one of those people. And so the idea of skipped level meetings where I asked everyone in my reporting chain, what do you want to accomplish here at SoundCloud? Are you set up to be successful at those goals? Are you aware of these programs that we have? How could you become more aware of them? What policies do you not like and not like? What policies do you wish we had and don’t? This became a set of questions that I would then ask. And I kind of accidentally invented this kind of questioning, which turns out to be a recommended thing to do because I just felt accountable for how people experienced the workplace because I was accountable. I was accountable for how they experienced the workplace.

Allen: It works.

Tiffany: And one of the first things I did, I kind of woke up one morning with this realization was, were there other people like me that had been kind of accidentally overlooked? And so one of the things I did is I went through the HR software and I looked at every person and I thought to myself, what do I think their level is? And then I looked at what their level was and whenever there was a downward… So I thought they were level three, turns out they were level two, I wrote their name down. It was not that many people. And then I had conversations with them. I was like, “So I noticed that you’ve been here for X number of years and you’re this level. Is there a story there? What do you think?” And I caught a couple of cases where the person had been either systemically based on the structures kind of held back, or no one had really encouraged them and no one had pointed out. And I was like, “Here’s why I think you should get a promotion. These are the reasons.” And they’re like, “Oh, can you put that in a document?” I’m like, “Yeah, sure.” And then there were other individuals where I found out they’re like, “Yeah, thanks for checking on me. I’m actually in the process right now.” So that’s the kind of thing that I felt accountable for because that experience had happened to me. I wouldn’t know how to replicate that at a brand new company, but I do think that auditing of who slipped between the cracks is something that if not the engineering leadership at the very least, HR should be accountable for.

Allen: This is a lot harder for an HR person to go through a list of people in the eng org and be like, ah, it doesn’t seem like Janet should be L2.

Tiffany: No, but they could have routine, even a survey that’s a similar kind of, do you feel like you’ve gotten the attention that you need from your manager to feel supported or whatever? Have you had conversations with your manager about X, Y, Z? Don’t think they ever ask what happens behind closed doors.

Allen: I’ve talked to a couple folks who’ve worked on these organizational design problems and trying to scale up compensation equity and making sure they’re retaining their best people beyond this scale where it’s like, I know everybody on the team. And so you end up building more systems and as we said, starting to treat engineers and people more as just things in a spreadsheet and stuff like that. And so I have all those problems trying to compensate for that and avoid that. And one of the things that I’ve heard before, and I’m not sure how true this is, maybe it’s an excuse, is that a person who’s been under-leveled incorrectly often can feel similarly to a person who is underperforming and is not going to work out where it’s in both cases, the person feels like I am worth more than this. I’m delivering a lot of value, I’m awesome. And then the person that they report to is like, this person isn’t really with the program either because they’re failing to recognize the value this person is delivering and the person is awesome. Or because they have the idea that a successful level three software engineer doesn’t break the build every Thursday, and the IC thinks, but I’m typing lots of code or whatever. Because people don’t always have a very clear self-perception, they can sometimes look similarly from the zoomed out two levels above, I’m the VP and then there’s a whole bunch of lines in the spreadsheet.

Tiffany: Sure.

Allen: That doesn’t mean that’s not an extremely important thing to distinguish between, but I don’t know, again, it might be an excuse, but-

Tiffany: Yeah. I think you look for signal and then you investigate, right? Is there an individual who’s got a long tenure at the level and has anyone checked in on them and had they checked in on their manager and had heard what the reasons are? So an example of somebody who is properly leveled, you would say you check in with the manager and the manager’s like, yeah, we’ve been having X, Y, Z conversations and here’s the paper trail of where I’ve talked to them and they’re aware la, la, whatever, there’s going to be an explanation. Versus the other situation that I heard, which was right before they were kind of finishing a really important task, they got a brand new manager and that manager was like… This is an absolute not an excuse, but people will go, oh, well I haven’t seen your track record. Well, then you’re not a very good manager because your job as the manager is not to see the track record, but to validate it. So if it’s true that this person had an impact, there are going to be people who know that, there are going to be people who can validate that. You as a manager don’t have to have seen it. And then this person went on maternity leave.

Allen: Yeah, classic.

Tiffany: And so there was this window of time where the manager’s like, I can’t possibly get to know you in time. They went on maternity leave, they come back from maternity leave. Now they got another new manager who’s like, I don’t know your track record, you’ve been gone for a year. This is classic.

Allen: Classic failure. This is how you lose a really good developer.

Tiffany: This is how you lose a really good developer. This is how women end up two years behind of their getting the proper pay. This is classic unacceptable behavior from a manager. So if you talk to a manager and they’re like, oh, well I don’t know because I don’t know what their track record is. Be like, that’s not an appropriate answer. That’s not a valid answer.

Allen: Find out what the track record is.

Tiffany: Find out. Do the legwork. Find people you can trust and validate it somehow. And so that is where there were a couple individuals where they had been systemically held back and there were other individuals who just hadn’t. Or there was other individual, like I described, which is no, there’s a whole history of this person having this conversation. They’ve had the same manager for a long time. The manager promotes other people. It’s not like the manager is not promoting other people. And by the way, something that got instituted at SoundCloud was a whole routine checking of exactly those things. Is this a manager who typically promotes or suggests promotion or is this one that typically does that, under promotes? And is there an explanation? ‘Cause there might be an explanation like, oh, well, they’re on a team that’s all brand new people and it’s formed out of nothing. And of course, nobody’s been promoted versus this is a team of really high performing. The role itself demands a certain kind of high performer, so of course that team sees a lot of promotion. And that’s the thing, you just have to look for these anomalies and then dig in. And I’ve started this conversation with somebody recently, which is it feels like this isn’t the job of engineering management, it’s the job of HR, to be having this kind of question.

Allen: I’ve heard it called organizational QA, a gray HR function ideally is helping you do the quality insurance on what good management looks like, and they have guidelines and metrics and stuff like that to ask questions and help ensure diligence through the varying levels of skill of the various managers, like we mentioned, the new manager that you just hired and they’re struggling with this and that, all the way up to systemic bias.

Tiffany: And I don’t know if the reason at SoundCloud it was management organizational-led because I don’t know why that was. And I don’t know if that’s typical or not.

Allen: I think it’s a scale thing or that’s my sense. I think at a certain scale, most orgs will tend to have HR have more and more formal expectations and analysis and software for doing things and risk of a lawsuit so they’d have more pf a structure. And that when you have a 100% company and certainly a 20% company, it’s probably a lot more like, oh, well, this manager reports to me and so I should help make sure that they’re doing things right and the HR person is worried about payroll or whatever.

Tiffany: And I also wondered if it had something to do with maybe it’s a Germany thing and the fact that the HR individuals are trained in a kind of more traditional German structures, whereas the people who are in engineering tend to be international, they’re online, they read blogs about what good workplaces look like. Not to say that the HR isn’t keeping up, but that they’re somewhat delayed in receiving these ideas. And I don’t know if that’s a German thing, if that’s a tech thing or like you said, it’s a scale thing.

Allen: I think it’s an HR culture thing that I’ve seen across different orgs, really different HR cultures, depending on to what degree the HR culture really comes from. People who come from a non-tech background versus people who came from startups and fast-growing software companies, which as you say, have different cultural expectations and have a bunch of things about our business that make trying to really innovate, I guess… I don’t like the word innovate, but innovate in terms of how we treat and develop people and how the bar we set for that stuff is. There’s kind of a more aggressive risk and return for that when your people are all making six figures and they are the life or death of your company. And as opposed to, it’s like, well, we’re Amazon and well, I mean, the fulfillment center part of Amazon, and then what does our business look like? And it’s like spreadsheets of like, well, we’ve hired almost 50% of all Americans at this point. What do we do now? Just very, very different considerations, right?

Tiffany: Oh my God, is that a statistic? Is that an actual thing or no?

Allen: No, I’ve inflated that statistic, but apparently I’ve read, and this is one of those somebody writes a headline to get clicks, so it may be a little bit overstated, but as I understand it, Amazon, on the delivery fulfillment center side, they have projections that have shown that they are going to start to have hiring problems because they will have hired and then either let go or had quit too high a percentage. They’re almost having saturated because they’re the number two employer. I think Walmart and Amazon are the top two employers here in America.

Tiffany: Wow, their churn of people is high enough that they will run out of fresh, never been. I mean, this is a problem that we face in software. If you churn out people, you’re going to burn through your audience. You need to…

Allen: So maybe they are somewhat the same. But my point with all that was just that the types of training and mentalities and frameworks and policies and jargon and mentality that you get of being in HR at General Electric or Ford or something like that is quite different than what you would have at Netflix and Google, Apple, Amazon, a startup, Slack or whatever. And so I think your point of this I’ve seen fairly often, and I’m sure that this happens in other industries too, is that management will take on some sort of HRE things, especially in engineering orgs where it’s like there’s one way that the org does it and then engineering has their way they want to do it. Cool. Well, I have one last thing. We’re coming on time. What idea or framework have you learned over the years that you found particularly useful or insightful, something you like to have in your back pocket?

Tiffany: So it’s this one very specific framework that whenever I think of frameworks that have been useful for me, I think of this one, which is six thinking hats. With the six thinking hats, the idea is that in the group thinking scenarios, you focus on a specific category of thinking at one time only instead of having this chaos of all the ideas all over the place. And so the classics six thinking hats is they have colors associated with them and they’re blue, white, red, black, yellow, green. And one of them is the managing mode. One of them is only facts, concrete facts. One of them is about feelings and emotions. The other is things that are kind of critical and bad, things that could possibly be good. And then ideas. And when I first was introduced to this, I can tell you the date, it was March 11th… Wait, let me do the math backwards. Yeah, March 11th 2020.

Allen: Oh, man. Okay. Yeah, sure.

Tiffany: So March 11th 2020 was the day that the Berlin office, at least at SoundCloud learned that we would be closing the office preemptive of any outside requirement to go into lockdown. And this was a decision that had come and now the Berlin part of the leadership team was going to be deciding how to then communicate this to everybody and implement it, and it was a very emotional time, very open questions. We were a fully in-person office and it was an intense time. And so my manager at the time, who was the head of engineering, Will Ellis, he immediately volunteered to kind of corral this group of leaders and he did a version of the six thinking hats, which he did with only five of them. And he introduced the premise and the first thing that he did was he did just straight up, what emotion are people feeling? And you get one word and you go all the way around the room and people give their single emotion. And then moved on to the other stages. And there’s a certain power in two different parts of this, which is you have a feeling or some complicated feelings and you don’t know who shares your feelings. And so much in these corporate environments, you’re told to just be really rational and these emotions are there. And by putting them out the very beginning and being like, what is everybody feeling? And some people are like, relief, fear, confusion, all these different feelings were coming out. It kind of makes space for complicated feelings to be allowed and accepted as present, but that we will then set them aside. Your feelings are valid, we’re going to just now put them aside and move into these other modes. And it’s very easy then if someone starts to brainstorm or criticize, it makes it very easy to say, wonderful, we’re not in that mode. Take a thought. You can see here we’re in the white column. We’re not in the black column. We will get to that then. And in especially heated environment like that was, it is possible to really focus people back onto the task. And I think it’s a very powerful way of bringing focus, not necessarily to what people are talking about in content, but in mode. And I think it was very obviously useful. And then I immediately took it back to my own team and kind of replicated that among the team. It was so simple and so powerful as a way to acknowledge intense feelings, but then switch to constructive, concrete, real actionable things. And I can see applying it in less heated environments as well, so I think it’s a really important one that people know exists. It’s great for facilitation, not just facilitating groups of people in sort of an emotional time. So that’s the one. If you don’t know it, there’s a book. I think I’ve told you everything you need to know anyway. You could just get started, but I think that’s one for people to look up.

Allen: Awesome. I can see how that would be really helpful in these circumstances where it’s a new dimension, you can slice a group meeting where there’s a whole bunch of different opinions, thoughts, feelings, stuff going on in the room. And the sort of traditional way that I often see it is you break it down by, okay, what’s the question we’re trying to answer right now? But then we have emotions, thoughts, criticisms, concerns, suggestions, all flowing in around this one particular question. They all iterate leads to other questions. So the value of saying, okay, we’ll try talk emotions for a bit. We’re just going to talk potential problems, we’re just going to talk potential solutions. We’re just going to talk different slices of it. That seems really cool. So thanks for that.

Tiffany: Yeah, I found it helpful and maybe other people will too.

Allen: Excellent. Well, thanks, Tiffany. Where can people go to learn more about you and your work?

Tiffany: Good question. So there’s only a couple Tiffany Conroys on the internet. One is a registered nurse in Australia. That’s not me. So if you Google my name Tiffany Conroy, I have been off Twitter since the middle of the Trump administration, but I’m now on Mastodon. And my handle there is theophani, T-H-E-O-P-H-A-N-I. You can find me if you Google Tiffany Conroy. I’m there. I haven’t been posting too many things. And then as I mentioned, in the last year, I’ve been doing this training and coaching consultancy with my business partner and the URL for that is golaminar.de.

Allen: Excellent.

Tiffany: And that is where you can learn more about me. Or you can email me at tiffany.conroy@gmail.com.

Allen: Excellent. Well, we’ll link those up in the show notes. Thank you so much for making the time being on the show. That’s it for today. You can give us feedback, follow us on social media or rate the show by going to itshipped.fm/contact. Until next time, keep shipping.

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