02:47 - Anne’s Superpower: Empathy & Collaboration

• Feeling Accepted & Creating a Sense of Safety
• Creating Happy Bubbles
• Making People Feel They Matter on Teams
  • No Matter Status (i.e. Employees vs Contractors)
  • No Matter Geographical Location/Timezone
• Equivalence in Remote Work

17:45 - Framing and Shaping Relationships + Communication

• Changing Company Culture
• Sharing Concerns with Upper Management
• “We are all on the same team.”
• Silence IS a Response
• Working Through Challenging Conversations

29:47 - Helping People Learn – Work Therapists: Should/Could They Exist?

38:18 - Having Support Outside of Work: Networking

• Find Communities First; Individuals Second
• Attract Your Dream Job
• @pivotgrowhustle
• #BlackTechTwitter
• Making Sure People Know What You Do!

48:20 - Overcoming Job Responsibility Misperceptions

• Managing Project Ownership and Roles
• “Secret Agile”

Reflections:

Arty: Being able to find strength and solidity within yourself so you can be someone that helps to contribute to moving things in a positive direction.

Casey: Coaching men on DEI. How could it be successful?

Anne: The future of where we need to go as a society, especially a tech-driven society, is to ask yourself how do you bring what you love to the table and to do it with love.

This episode was brought to you by @therubyrep of DevReps, LLC. To pledge your support and to join our awesome Slack community, visit patreon.com/greaterthancode

To make a one-time donation so that we can continue to bring you more content and transcripts like this, please do so at paypal.me/devreps. You will also get an invitation to our Slack community this way as well.

Transcript:

PRE-ROLL: Software is broken, but it can be fixed. Test Double's superpower is improving how the world builds software by building both great software and great teams and you can help. Test Double is hiring empathetic senior software engineers and dev ops engineers. We work in JavaScript, Ruby, Elixir, and a lot more. Test Double trusts developers with autonomy and flexibility at a remote 100% employee-owned software consulting agency. Looking for more challenges? Enjoy lots of variety while working with the best teams in tech as a developer consultant at Test Double. Find out more and check out remote openings at link.testdouble.com/greater. That's link.testdouble.com/greater.

JACOB: Hello and welcome to Episode 255 of the Greater Than Code podcast. My name is Jacob Stoebel. I'm joined by my co-panelist, Casey Watts.

CASEY: Hi, I'm Casey. I'm here with our other co-panelist, Arty Starr.

ARTY: And I'm here with our guest today, Anne Griffin.

Anne is a product leader, a startup advisor, and subject matter expert in AI, blockchain, tech ethics, and inclusivity. She is the owner of Griffin Product & Growth, a product consulting and advising firm. Her workshop, Human First, Product Second, teaches organizations and professionals how to think about building more human, inclusive, and ethical tech products. She has lectured at prestigious universities across North America such as Columbia University and West Point, spoken at major events such as SXSW, and created courses for O’Reilly Media.

Outside of her work, she loves rest, barbecue, and beaches.

Welcome to the show, Anne.

ANNE: Thank you so much. I am absolutely thrilled to be here today. It's a gorgeous day in New York.

Arty, I know I've had a couple conversations with you. Jacob, we'll talk about this in a little bit, but we've had a conversation before and I just really love you guys. You guys are great. And Casey, I'm super excited to meet you.

ARTY: Yeah, the last time we were recording, we had some challenges with audio issues and so, we weren't able to get the podcast together, which is really unfortunate because we had an amazing conversation. But we're all back here together and I'm sure we're going to have a really awesome conversation this time and it's probably going to be even better than before.

So I'm excited to ask you our first question, Anne is what is your superpower and how did you acquire it?

ANNE: I would say one of my best superpowers is, maybe this counts as two separate things, but it's a combination of empathy and also collaboration, which I think empathy definitely helps make for a good collaborator.

And where I got it, I think it’s a combination of places as well is really growing up, I was never the popular kid. I was always the kid that was picked last in the gym. I had some friends, but I was really – again, I was unpopular; I didn't really have that many friends. I was picked on a bit.

So for me, I was in this position where I was always super conscious, or tried to be of how the things that I was doing was making other people feel. Because being in a position where I think some people thought like, “Ha ha ha, that's funny,” and don't think anything much further than that for me made me feel not very great. So I think some of that started from there and not to say I didn't have places where I was like, “Oh, I could improve in terms of empathy,” but I really think that's really where it came from.

Also, in terms of my working style, I've always worked best being in a collaborative environment. I'm not super happy when I have to work completely solo and there's zero collaboration going on. Not saying there aren't things in product management where you are working solo, but one of the things I love about product management is by nature, it is a super collaborative role.

And really, you have to have empathy to be a good collaborator because I would rather have somebody doing really amazing and creative work because they feel inspired to, they feel like they can be themselves and bring them their best selves into the workplace, and that there is trust. That is the thing that makes me feel the best about anything I do honestly. And obviously, launching new things. That's great. I love that. Obviously, it's a big part of product management. I wouldn't be in it if that wasn’t important.

But honestly, I think I get equal amounts, or possibly more fuel from knowing that my team feels empowered, knowing that my team actually loves being on the team, and is really just excited to be together and be able to just do their best work and not out of like a, “Oh man, I'm going to get in trouble by someone,” or “Oh, I have to be super scared of political stuff,” but really being like, “I got to show up as me today and that empowered me to be my most creative and best self.”

ARTY: Wow. The story you were talking about at the beginning with how you were feeling growing, never the popular kid and how that made you kind of hyper aware of how your actions and the things that you did ended up influencing the people around you and just developing this hyperawareness that gave you this empathy and how you were thinking about things.

I'm curious, did you also have environments and context where you were accepted and well left?

ANNE: Growing up, obviously, I'll say I was very fortunate that my family has always been very loving and accepting. So I'll say one of the most critical environments I had that I went to daycare for a really long time and I felt like there wasn't really this I was an outsider there, but in terms of school environments, and I'm not really sure what it was, pretty much from grade school all the way through high school, I was an outsider.

So I think it's also having have been in certain other critical environments where I was loved and accepted and I think I met one of my then best friends in 5th grade, which then she eventually changed schools, all this other stuff. But having certain people, even if there wasn't a lot, and then having those critical environments where I was accepted. Knowing what it feels like when you are accepted and contrast to this whole thing of feeling like people don't really care you're there, or they don't really want you to like join them at lunch, or other things like that.

CASEY: Yeah, that contrast sounds really powerful.

This is kind of random, but it's reminding me of, I went to physical therapy last week because my posture is bad. My hands went numb 2 years ago. It's recovering. I'm pretty good now. But they were teaching me how to do a squat with good posture and they said, “Here's the right way to do it. Bend your back here, do this, make sure your shoulders aren’t tense,” and then they had me do it wrong. So I got to do it the right way and the wrong way and that helped so much. I've had like 4, or 5 PT people. This was the first one that showed me the wrong way for contrast. It's powerful.

ANNE: Absolutely. I agree that it's so powerful and I think for me, that's part of where I originally fostered like here are the feelings I know I want to have and that I can have and how do I create that sense of safety in being one's self outside of these environment? I really felt like once I got to college and especially once I was working in environments that were healthy enough and safe enough for me to be able to create this is the right type of environment where there's trust and collaboration, I was able to do that because I had experienced the wrong way of—I'll say, the wrong way as in being excluded from things, people not really caring about how you feel based on comments, but had also, this area where I had learned also the right way.

Actually, one person who was very, I think, fundamental in helping me translate that into the work world is one of my mentors Dana. Actually, she used to work at Microsoft. She actually early retired from Microsoft. So she was at Microsoft while I interned there and she really taught me that well, it shouldn't be on you to solve all your workplace's problems because they're not paying you to solve a culture problem that they should be handling. But you should really act at work in terms of implementing the type of culture that you would want to work in. Don't just be, “Oh, I'm just upset because all this bad stuff's happening,” and that kind of stuff. You have the right to be upset if bad things are happening in your workplace.

But if there are certain things that you can foster that you have control over in terms of the attitude on your team and how you empower other people to be able to talk about what are the problems, what is going well, what don't we like, how can we change it, what are little things that can nudge the atmosphere and really foster that? Because there's some places, they're going to be toxic; [chuckles] they're not going to be big impact there.

But there's also a lot that can be done in places where you are empowered to do that. Especially as a product manager on your own pod, or your own team, so that it is a happy place to be, that people do feel included. People don't feel like people can just jump into your Slack channel, say a bunch of trash, and then leave and it's completely fine. I think that's that contrast there is learning what is the right way, the right posture, I guess, for that type of environment really helped me and especially from my mentor Dana at Microsoft.

CASEY: Anne, I feel like you are saying so many things I say all the time and I’d love to hear it from another person's voice. I believe strongly that you can make a small bubble that you're in. Like a happy and effective environment, a team that you're on. Even if it's a toxic culture overall, you can have your own happy bubble, but I don't know. A lot of people don't value that, or they don't celebrate it when they manage to get even one bubble and that can be frustrating. That’s why it's so cool to hear that you have felt like you've made some bubbles happy before.

ANNE: Yeah. When I say empathy and collaboration are my superpowers, I would say also creating bubbles are one of my superpowers, even in remote environments. Even before the pandemic, one of the places I worked was a remote first company. It's always really interesting because I think because again, empathy and collaboration are my superpowers, I crave that a lot and I'm going to be working for 8 hours a day so I try to create that everywhere I go.

Not saying I'm trying to exclude people from the bubble, but anybody who wants to be a part of that type of culture, I welcome them into that and it's amazing because I'll go into places and even that small startup people are like, “Whoa, when you started, I noticed this big culture shift.” It was really small so it was much easier to make that kind of impact, but people started feeling a lot more connected to each other, especially we were remote first.

We weren't really centralized in New York, or in the United States. So there were people who were either based in Nepal, or Mumbai where they said because of the time zone differences, people didn't really think about okay, is that person getting the support they need when there's hours where people are not up and if we have more people in other time zones, how do we make sure those people feel included? Because there's a lot of ways you can actually make people feel excluded, even if it's unintentional and people may still resent that, or still may feel bad and even if they don't resent you, or blame you, those are things where I think a lot of people just say, “Well, it's not really my problem,” or organizations say, “Well, if they want to get a paycheck and they want to work remotely from that region, they're just going to have to deal with it.”

I also think I'm like, “But if you don't care, why are you hiring people in that region if you're not going to foster a culture and just an overall company bubble of making people feel like they matter, that they're included, that they're getting support and being creative with how you also support people asynchronously?”

JACOB: I think like in addition to that often is the case, the geographical differences, there's other differences at play that are specifically about power, or just in terms of country of origin. You might have a lot of circumstances where you've got people on salary in the States and everyone is a contractor in India, or something. I think there's a lot of intersecting issues that can come up with people working internationally.

ANNE: I would say, I completely agree. At that startup, everyone was an employee, but I definitely think there was a difference because people are used to, “Oh, those people in that time zone are usually a contractor.”

I've worked at plenty of companies where if somebody was remote, it was because they were contractor and they usually were from a country of a lot of brown people and how people treated them was different. It's very fascinating because consistently I see in cultures where there is not conscious messaging from the leadership about “Yes, these people are contractors.” Yes, we've outsourced this work to this place.” Conscious culture shaping and messaging from the leadership. “Hey, they are part of our team. We're working on the same goal. This is how we treat each other in this environment.”

You get very inconsistent results in how people choose to treat those people and I've seen it where I've worked with a team and it was like, “Oh wow. This was such an amazing project. We work really, really well together.” And then that same team gets passed to another person next project, that sort of thing and I talk to the contractors and they're like, “Yeah, no, that person just yells at us and tells us every time we do something wrong and they don't ever bother setting up time to discuss requirements in more detail.” They just feel like, ‘Oh, you should get it.’

You have to think about okay well, why would you not have these conversations with somebody who's based in India, or Columbia, or Brazil, but you're having these conversations at the coffee cooler in-person and you expect them to pick up the same amount of information, to understand the same amount of context?

It was just confusing to me because for me, I felt I would be very stressed out and have tons of anxiety if I feel like I'm missing lots of information, lots of context and my team is just telling me, “No, no, no, no. We gave you everything you should to just understand it. I don't think we really need a meeting because I sent you everything.” And me feeling like I still have questions and there is either this resistance to making time to talk to me about it, or this sense of I should already know this, which I think some of us have all experienced that at some point in our career like, “Oh my God, I'm scared people are going to think I already know this,” but when you're in that also power dynamic and you're on the side of less power, I know I would feel hyper anxious about the perception is that I'm not doing a good job when I'm really trying my best.

So those are things that also really bother me when it comes to people decide we're going to have a team that's going to be based in this different time zone, or this is going to be the only team that's not based in the US and there's not thoughtfulness from leadership. How do we create a culture that everybody feels included and everybody is set up for success ultimately?

Because people really liked the idea of remote work when it was like, “Oh, I can move to Ohio and get a really nice house and have a place in the suburbs.” But then there is all this stuff where people like that idea. But before it was like if you have someone who was based somewhere else, there was a lot of stuff where people are like, “I don't think we need to really do anything extra for them. They got it.”

And then people who are now experiencing remote work for the first time, they're like, wait, there are actually certain things that are pretty hard. Especially if certain people are centralized around certain time zones, or certain locations. That is just not something that is, I think well-thought-out and especially when we start talking about contractors. Even if a company decides these are going to be full-time employees in other countries, depending on how long a company has existed in a centralized location, there's sometimes resentment and fear that oh, they're just going to hire all these cheap people from this country and that seeps through in how people choose to communicate with those people.

I know I'm saying a lot, but I'm also super – I've been technically working with remote teams since I was in college and the first full-time job I ever had, my team was based in Belarus. I've worked with so many remote teams over the years and I have so many opinions [chuckles] about it. I just see again and again, and again that all it really takes is okay, if I would say something like this to someone at the coffee cooler about, oh, this project's happening, da, da, da, da and that little extra context, which sometimes seems insignificant. I need to make sure that there is some Slack message, email, how do they work best like some sort of thing so that they are getting an equivalent experience in a remote world.

ARTY: Wow. One of the things I'm thinking about now is just how much very few words, very few communications that we might have with someone has in terms of impact and shaping that relationship, and impact and shaping all communication that cascades from that relationship. Like you were talking about this example where you had one experience with a team and then there's another relationship that takes place.

The view, the perception of how they see these other people and this other team out there versus your experience—just the variance in the relationship and how it evolved the perception of the team and their capabilities and everything else—can just snowball from there, from the seed of a few conversations and the importance and the responsibility of leadership to frame that relationship, to frame it in a way that is supportive, and seeing of the humans and the challenges, and the power of going, “You know what, we're all on the same team.”

CASEY: I'm thinking back to the small bubble thing we touched on before. It sounds like if you were on a small bubble team with these remote people, you could fill them in. You're on it, you got this. But then if they're on another team, a small bubble that's not as remote aware and thoughtful, then they're not going to do as well. So I'm always thinking about this. I'm so confident I can get any small team to be a happy bubble if I'm in there long enough and I put my mind to it. But then the level up, it's not necessarily within my power as a PM to make a change above my level.

What experience have you had around trying to do that, whether it went well, or it didn't go well, or you made some amount of progress toward changing the company culture? I want to hear that.

ANNE: Yeah. So one of the companies I was at, they opened up a new office that was many time zones away from the centralized time zone. This was a thing where the centralized office was in-person and they created another in-person office in this other time zone, full-time employees. There were just things that people would say that were so small, but it was driving me absolutely nuts. Because I was like, “I know you guys wouldn't say that in front of the people from that other office.” It would be things like, “We don't know what hours they work,” and this was after a whole quarter – I think that office had been open for at least a year and the people who were saying this, “We don't know what hours they work” had been in a meeting actually that I set up that was once a week with those specific developers.

I talked to my boss about this because I said, “Okay, so usually if I have a question about, ‘Hey, what hours are you working whether it's like, you're in my same time zone and you drop your daughter off every day at 3:00, or whether you're in some very remote time zone from where I am.’” I'm like, “Just ask them.” I'm like, “They're right there.” Like, how is their confusion? Why is it that you can talk to the people that you know in the US, but you can't talk to the people that are outside the US that also happen to be brown people?

There were other little – and that's why they sound really small, but I was thinking, I was like, “But literally, we've been working with them.” [chuckles] like, directly with this specific team for now three whole months, how are we saying I spent three whole months in meetings with them and I never asked them this question? Google Calendar also has working hours, which our company utilizes. So I was like, “If you have a question about are their Google Calendar working hours up to date? That's a very simple question.”

The fact that it was like, these were questions that were being asked to a broader group where people from this other office were not included and they were like, “I think we need to better understand ways of working,” which I agree. You want to understand what helps people work their best. But these were things where it was just like, this is hard working with them and I was thinking to myself, I was like, “This whole quarter, this team has actually been ahead of schedule and you've been in meetings where if you had questions, you could ask them directly. So why is this a organizational concern now?” It was something where I don't think anybody intentionally meant harm, but I thought to myself, I was like, “I would be mortified if any of this got back to anyone in that office.” Number one.

Number two, I was like, “This doesn't have a place in our company, but I am not at a level where from a political standpoint, I can confront some of the people who said those things.” So it's something I had to go through my boss and say, “Here are my concerns. I don't think this was intentional. But the fact that these concerns only popped up with these specific people in the specific office that also happen to be in a country where realistically, they're getting paid less than us.” It's an office where there's only going to be brown people in there—and I don't say Black and brown because it's a place where it's like, there's definitely only brown people in that office.

But I had to address it with my boss and my boss had a conversation and some of that stuff reduced, but it's the kind of thing where running into those things and running into people where I'll say a lot of times, it's not even direct, but it's things where I'm like, “They know what those things mean when they hear them and I know what those things mean when I hear them.” I just think people don't consider how does me thinking – even once the thought and gets in your head, you have to stop and think like, “Does this thought even make sense? Why should I be concerned about this? Maybe I should stop myself and be like, ‘What can I do to [chuckles] make sure that my questions don't make people feel excluded in this environment, especially because they work here?’” Contractor, or full-time. These are our full-time people. But even if they're contractors, they work here. We share the same goals. We are on the same team. We are part of the same culture.

I don't believe in having second class citizen people in a company. I don't believe in second class employees. So I'm like, either the way we ask questions about anything about them, or the way we think about them is not going to be different than how we're going to think about everybody else who's US based and also in a primarily white environment.

I'll say it did get better after that addressing with my boss. But it is something where it's a lot easier to handle when it's on your team and with people you have a lot more influence over. It gets harder when there are sometimes people above you, or are in other circles where you're like, “Those people did come to my meetings, but they were technically out of my bubble in a way and I had to kind of go a level above me and voice my concerns because if I don't voice those concerns, no one else is going to voice those concerns.”

Also, I don't know if those people are necessarily empowered. If they had overheard those things, are they going to feel empowered enough to say the truth? Are they going to be afraid for their jobs if they speak the truth about how that type of thing makes them feel? So oftentimes, there's this thing that happens at companies where people feel, “Oh, well no one said anything so it must not be a problem.”

ARTY: Yeah. The silence is a response. It's a thing that we feel and experience, too. When we say something and the response is silence, when something happens and the response is silence, it's a response. It's not an absence of response; that is a response.

CASEY: Yeah. This sounds like a stark example of a power dynamic. So it's the main office/remote office. It's the culture and ethnicity, both. I'm wondering if the people on the more powerful side of the group, the main office, are they aware of this dynamic? If they're aware, are they interested in doing anything about it? If they're interested, are they committed to doing things?

I can tell, Anne you are committed to doing things, but of your peers. I wonder where they are in the spectrum of being aware. If they're not aware, it's hard to blame them. If they're completely unaware and no one's offered the ability to become aware like DEI workshops, I don't know, then nothing is a silver bullet.

ANNE: Yeah.

CASEY: But there's a whole path that people go on to become such strong allies like you are.

ANNE: I think it can be hard though, because in several companies, I've had trainings about unconscious bias, harassment, things you don't say about team members, things you don't do to exclude team members, how to create an inclusive environment. But then once you get into reality, things that people start thinking, for them maybe are in a gray area, or maybe a specific thing that wasn't covered by that training. There's a lot in which people are like, “I could never harm someone in that way because I'm not racist. I'm not sexist. I'm not homophobic. I'm not ableist.” I think that's one of the problems we have as a society, even bigger outside of the workplace, is this perception that I who took the DEI training, or I took the whatever training could not be racist. I'm married to somebody who is of this background. I have a friend that is this. I have friends who are gay. I can't be this.

There's this whole thing where I think that's one of the harder things to learn that even someone like me where I'm like, “Yes, I'm committed to changing this,” and da, da, da, da. I can still harm people, I can still mess up and hurt people, and I don't get to just say, “I had good intentions so you should just be grateful for that,” or “I had good intentions. Therefore, it doesn't count as this.”

That's something that I think we need to learn more that even if you have the best intentions, you can still hurt someone and it still counts as hurting someone. [chuckles] Doesn't mean it doesn't count because you had good intentions and sometimes you just have to say, “Oh my gosh, I did say that. That was this. I need to work on this area. I'm sorry.”

I think our reaction to society is we meet the reality of ourselves in ways and times that we don't expect and it can be a shock and out of fear of like, “Oh my God, if people think I'm racist, am I going to lose my job?” Or da, da, da, da. I'll say, if you're very racist, I do have opinions on that. [chuckles] But if it's like you made one comment, I’m like, “Apologize.” Realize you're like, “Yeah, me being concerned about how these people work maybe didn't make a lot of sense.” “Yeah, my best friend is this, or this, but for some reason, I still thought that thought,” and that's something where it's like we don't really teach people how to confront that, or that it's okay to be like, “Well, crap, I messed up here. Let me apologize.” Instead of putting out five non-apologies before I put out an apology later where nobody really believes and it's not sincere.

JACOB: Or how can we have an environment where that feedback loop related to microaggressions is just normal and low friction?

ANNE: Yeah.

JACOB: And then certainly, people will should obviously make amends for it, but it doesn't have to have more drama than necessary.

ARTY: I think those kind of conversations are always uncomfortable, but that doesn't mean we can't have uncomfortable conversations and learn how to be resilient working through challenging conversations. Like I don't think – it's not that it doesn't get easier with practice and things.

CASEY: For my work with my consulting group, I like to focus on people who are interested in learning and then how they just need practice. They need to know those tools and the techniques and they can practice it. I'm personally not interested in people who are totally unaware and disinterested. That is a harder battle and I want to get better at this middle step first before I would focus up stream, up the funnel. But there are a lot of people who are just oblivious and they would love to learn and have space to practice this and that's its own problem, its own difficult challenge.

ANNE: Yeah. I agree in terms of giving people a place, who actually want to learn and I would say also are doing the work to learn because – [overtalk]

CASEY: Yeah.

ANNE: And I'm not saying, okay, if somebody is on the receiving end, that they should be that person to have to put up with this, but it sounds like you have a consultancy where you're able to work with those people. People can pay money. So obviously, somebody is interested in being there to actually have that space and learn because some people, they would otherwise learn more, but there's certain things where it's nuanced.

Also, I think there's a piece about in practice because there's one thing where you can read something like White Fragility, you can read all the books you want, you can find that article on the web, and still have things that come out of your mouth where you're like, “No, don't say that, don't do that,” or “In this situation, just your specific action even if it's not words was not great,” and teaching people the tools of recognizing for themselves because it's also reading self-help books.

CASEY: Yeah.

ANNE: But then thinking, because you read the self-help books, that all your inner actions in real life are perfect and fine. That's why we also have therapists because therapists tell you – you're talking about your day and they can help you unpack well, why did you think that? Why was that your reaction? What were you thinking? What were you feeling? Because you can read all the self-help books and think you're doing these things and there could actually be all these layers under it that you're realizing, “Oh, in practice, I think I'm doing this, but here are the actual outcomes of what I thought I was achieving.”

JACOB: Because there's a feedback loop where you get to, for lack of a better word, experiment with what you learned and find out if you understand it correctly. I don't really like that word experiment—I can't think of a better way to put it. But it's like, I can learn a foreign language all I want by studying in a book, but it really cements when I go and have a conversation with a person that speaks that language.

CASEY: I like the parallel to therapy. You just inspired a new idea I never had before. What if there were some people who would coach others one-on-one like a therapist, like a session. I do more workshops where I end up having people in breakout groups and they talk to one, or two other coworkers about things. It's hard to make that safe space where they're comfortable and they'll make progress, but I'm pretty proud of that I can do that in a lot of the time, but then there is no expert involved. There's nobody who really knows; it's just peer feedback.

So what if there was a coach for one-on-one training on how to be a better ally? I think that would be really powerful. And my question is how do we get companies to pay for it for their employees? That's its own problem because workshops scale better.

ANNE: Yeah, and honestly, I really feel like they should just have that type of person on retainer for especially the leadership. Not saying individuals on teams don't need it because I think that's another thing where it's like I'm not saying, “Oh, reserve some of the most expensive resources for leadership and lock it away.”

But also, we're talking about how do we teach people to recognize what they're doing and also, how that impacts the teams that they're responsible for managing and how that impacts the company culture. Because I think that's how we end up seeing a lot of these things keep repeating themselves in company culture again and again and again and again. Even the things that are perfectly legal, but are actually still harmful in some way, shape, or form to different underestimated and underrepresented groups and I think that would have a massive impact.

JACOB: This is a great idea because I feel like I've wanted to work out questions I've had about work with my therapist and there's so much I have to bring her up to speed on just in terms of she doesn't work in tech, she's a therapist [chuckles] and doesn't understand the company at all because again, she doesn't work there. I feel like that would be so helpful; just someone who understands generally what this company is working on and what my job is, but doesn't have an active day-to-day involvement in what I do and can give hopefully, a less biased perspective. I love it.

CASEY: I hear that from a lot of people. People want a work therapist.

ANNE: Yeah.

CASEY: Or whatever you call it.

JACOB: Yeah.

ANNE: I think they exist a bit. I don't know specifically how you find them, but I will say so, it’s not a therapist and there's different types of career coaches. I have a career coach that I've been working with since I think 2015 and she's not a therapist, first and foremost and also, she is not this type of role that is helping me be less any of the things that potentially anyone could do to harm another group. She's not there to be like, “I heard you mention this. That sounds ableist.” She's not doing that.

But one thing that has really helped me in my career is having somebody who actually knows what I do. She is not someone who is in tech. She is a third-party person and she actually knows the different problems I've had in different companies, where the themes are, what has been unique to different companies, and also asking questions to unpack things to help me also understand am I the asshole in this situation, or was something else going on that was completely out of my control?

That has given me really good perspective in my career in where am I owning something that's happened versus this is out of your control. Maybe there's some things you could have done better, but also, don't beat yourself up over this thing when your leadership team should have been doing this. She also knows my habit. She also knows that hey, it feels like you're slipping back into this habit at work.

There's different types of career coaches. There are different ones where they're like, “I am focused on product management thing, XYZ and this is what's going to get you specifically this promotion because I'm going to have you work on this specific product skill.” This one is, she's more of a generalist.

I actually started seeing her more for career influence product coaching, where I was much more junior at the time and really struggling to understand where the disconnect was in my career, where my actual project teams were saying things like, “Wow,” “You do such a great job. You're amazing,” da, da, da, da, and have very senior people I worked with that would say, “When are they going to promote you?”

And then when I would speak to my manager and my manager's manager, it felt like I was treated very junior, I didn't really know how to talk to them. So the things that I was updating them on, I thought were very important, which then I then learned oh, it really just made me sound like I don't know how to focus and I was just pouring information at them and they were like, “Oh, she doesn't know what to focus on and she doesn't know this.” I thought I was impressing them. [chuckles] It's one of those things where having somebody with that third-party perspective and also someone where they can help you work on specific things that are, I think more general also is very helpful.

She's not a work therapist. She's not helping me unpack how my childhood experiences impacted how I reacted in the work situation. But she is someone who knows a lot of my work history because we've been working together for so long and I'm able to talk to her about when things are going really, really well. She's talked to me when I'm like, “I started looking for a new job because I can't take it here anymore.” So that's been something I really value.

CASEY: That's so cool. I love hearing it. You have support. Your support doesn't have to exclusively come from your manager and your current job. You hear that, everyone listening? You can have other support. It could be friends, too.

ANNE: Highly recommend support outside of your manager and your current job.

JACOB: Not easy in a remote workplace, or maybe it is, I don't know, but I would think it
would be harder.

ANNE: Networking is really big and I know people always are like, “Networking”! But to be specific about networking, because there's different types of networking, networking in a way where you are finding the online communities of people who value the same things as you and possibly even going through similar things, but not resorting to toxic ways of dealing with those things has been one of the biggest career hacks in terms of finding people that also understand outside of my career coach. Sometimes I can even ask them very specific questions to being in tech, or very specific questions to being a PM, or being a PM as a Black woman in tech.

Those type of things have made a big difference for me because there's a lot of things where you start seeing patterns and oh, other people are experiencing this. This is how other people are dealing with it and ways it didn't work out and the ways it did work out. That's something where just sending LinkedIn messages off to people who just seem like very successful. While I know that is a thing, I've really found the things that have made the biggest difference for me is finding these groups, whether they're private Facebook groups, or they're LinkedIn groups, or they’re private Slack groups for women in tech. Really, that is where I've been able to find additional support.

Also, there's people where even they're my peers and I'm like, “Whoa, we're now collaborators on something that we both really value a lot, that my day job would never give me a project like this and now I'm getting to collaborate with somebody outside of my day job to work on this thing because I met somebody else who fits in turn of values, what they're interested in.”

I think that's one of the biggest things of networking is finding the communities first before you find the individuals because in those communities, you're going to start noticing who are the individuals I tend to align with and maybe I shoot them a message, or maybe they need help with interviews and I can do a mock interview and then that starts we reach out to help each other, that sort of thing. Those are all things where I highly recommend and I think are much more effective than just being like, “That person looks like they probably make a lot of money at that company,” that has always been the most helpful for me.

CASEY: So I'm wondering, how do you find these communities? One trick I love is to tell people you're looking for those communities, they might know. I don't know, why this is so far into a lot of people. You should tell people your goals publicly. Did you do any of that? How did you find yours?

ANNE: Absolutely. Some of it is telling people, “I'm looking for these communities,” and some of it is people I've worked with in the past who have been part of my bubble, understanding those are the communities I would want to be in and saying, “Hey, are you in this Facebook group?” and me being like, “No, I've never heard of it,” and then they just add me.

There's one that is for Black women in tech and it has been one of the most valuable online communities I've been in long before the pandemic because somebody just added me because they know my values align and also, being a Black woman in tech and having to experience certain things.

In addition to everything else I do, I also run a small group coaching program called Attract Your Dream Job where basically, I teach people how to get companies to come to them, or if you do apply making it so that you have a better likelihood of them actually responding to you instead of applying to a hundred companies, just what I call spray and pray. So how do you avoid that?

One of the things I always tell people is actually the thing you just said first step is number one, tell people that if you're looking for a job, don't blast it out on LinkedIn. If you have a current job, you don't want to get fired. But tell your inner network, get their email, send them a DM on LinkedIn something and if you're also looking for those groups because we actually have an assignment that is you actually need to find three groups like this for your job search and telling them reach out to people saying, “Do you know a group for people who are really into art and backend development?” I've made that up, but those things where it's not just like, “Here's just a generalist tech group, tell them what you're looking for.”

And then the other piece I always tell them is go to LinkedIn, go to Facebook, go to even just Twitter. Well, you could start with really LinkedIn and Facebook, you actually can search for such and such group in and then whatever your industry is and that's one way it's actually very easy to find people to connect with, or those communities. And then also on Twitter, starting to browse around, I'm looking at hashtags there's #BlackTechTwitter, which is like, I really love that and there's a lot.

Actually, we did a whole barbecue here in New York in 2019 because of #BlackTechTwitter because I was like, “I have this idea that we're going to have a Black Tech New York cookout,” because I was like I never see other Black people in tech, unless this is a hiring event by this company for DEI stuff and I was like, “I’ve never see an event that you just get to hang out and talk and while we might talk tech, this is really just an opportunity to meet other people in the industry who are like you.” That really was all organized off of a thread on Twitter.

So there's lots of places you should go, but you should always let people know what you're looking for, what type of community you're looking for, because people don't know. They don't know.

The other thing I always tell people a lot. You'd be surprised how many people who have no idea what industry you're in, or what you do. You think your friends know. You might even think people you used to work with know. But one example I give a lot is one of the jobs I used to work at, I had a coworker who got peer feedback. He was a product manager. He got peer feedback from someone else that his wireframes were terrible and my coworker doesn't make wireframes. [chuckles] We have a whole UX designer on that team that was responsible for wireframes. But the peer feedback was like, “This person's wireframes aren't very good. This person's very nice, but the wireframes are bad.”

You realize while this is not necessarily the most common thing, if somebody on your team that worked with you for a whole project can misunderstand what your role was in the project and what you actually produced, people who haven't talked to you in a year, or two can easily misunderstand what you are doing, or if you’ve changed industries. There are a lot of things that people can get confused about. They saw you post something on your Instagram once and now they think that you work there. So there's just a lot of ways in which people actually have no idea how they would even stay hard to help you if you don't tell them.

CASEY: Yeah. People don't know. I got an award for the last company I worked at a year after and I was hesitant to post it because I'm like, “I don't work there. I've been gone a long time. I don't want to confuse everyone.” I did anyway, but I don't work there. Surprise! [chuckles] Yeah, people don't know unless you tell them, unless you talk to them about it and even then, they might not remember. That's normal human behavior, too. Especially in tech. What's a product manager anyway? [laughs] That's the question. I don’t.

ANNE: That is the question and the reality is that while product management as a discipline has been around for a while, there are a lot of companies who did not have product managers, really, or a product manager discipline until the last 5 years. That's just the reality. We like to think, “Oh man, this has been around for a really long time.” It has, but there are a lot of companies where they were like, “We have a project manager and we have a BA,” and there's no one who's a product manager.

While some of those skills overlap, a product manager has also a lot more of this undercovering the why piece that technically isn't a solid responsibility of a project manager and a BA. Those people can do that type of thing, but they're technically not accountable in their career for those things. So if you want to make sure you hire someone who is going to be accountable for that, has a track record, and is much more focused on moving metrics than just, “Hey, the project is done,” you would want that separate discipline.

But you have actually certain developers where oh, this discipline is really recent at this company and that developer has been there 10 years and they're like, “I only know the product managers I work with,” and half of them were basically just project managers where the title changed and – [overtalk]

CASEY: Ah, I hate that.

ANNE: Yeah, which some of those companies do stuff to upskill those people, but there's a lot of people out there who've never worked with a product manager and don't really understand well, what is the difference between that and a product manager?

I actually had someone at my current job, who actually is my best work friend, who didn't understand the differences between a project manager and a product manager. She thought it was a matter of semantics. She's not someone that I necessarily get to work with frequently so it's not like she's viewing my work and she's like, “It's the same,” but it's something where people even you work with, it's not even guaranteed that they understand what you're supposed to be doing and after you stopped working with them, they probably have no idea what you were [chuckles] supposed to be doing. They forgot. They were like, “Yeah, they did good things,” and like, “That person was a good project manager,” and you’re like, “No.” [chuckles]

But it's the kind of thing where you have no idea what people's perception of what you're supposed to be doing at your job, where you could be a frontend developer and somebody saying, “That person was not very good at updating things from the database,” and they're like, “Yeah, because they're a frontend developer.” There's a lot of stuff where people don't necessarily know, or understand based on the industry and company they're coming from.

JACOB: Where do you think those misperceptions come from? You touched on a little bit, but why? Is it just that our brains are so full that we see one tweet from somebody and we just attach that to that person because we don't have enough energy to learn more, or?

ANNE: I think there's some of that. I think there's also, some of it is how the human brain works and it tries to oversimplify things. I also think it also comes from there is often a fear of asking too many questions. Especially if you're not in an environment that fosters a culture of trust and safety and there can be a fear of asking, “I forgot. Can you please just explain to me what it is your responsibilities are and what it is you do?”

It also gets really tricky when, because every organization does this to at least a few people, somebody starts filling gaps for things that they see missing in the organization. That's not their job, but they start doing it and then that person becomes auto-enrolled and being the person responsible for that thing. They might be, “Oh, that person's a frontend.” Their title might be frontend developer, or frontend engineer, but let's say that person started doing wireframes because they couldn't get enough of a UX designer’s time. So they started doing that and started getting really good at. The company started saying like, “Okay, well that person's on the project so that they could handle wireframes,” and then it becomes a thing where that person does talk about UX things. But the perception is that person's not a developer, that person's a UX person and people not actually ask them questions.

Sometimes organizations not doing the right thing, sometimes it's because organizations can't afford to hire somebody, especially when you're talking about startups. Especially once you get into bigger organizations, sometimes they choose not to hire somebody else. Somebody starts trying to fill the gaps because they are the type of person where they cannot stand to see, “Okay. So we're just going to sit here and be blocked, or be yelled at, or something because nobody wanted to even just do a simple mockup in PowerPoint?”

Those are things where organizations also allowing for ill-defined roles and letting people be a catchall also creates that problem where people perceive you as one thing and in reality, well technically, this is your role and now people are saying, “Well, that person is not involved, but when I worked with them, they were doing wireframes.”

It’s really a little bit organizational problem, also how our brains work, and also just the nature of people actually [chuckles] trying to be proactive and that sort of thing. Also, we said that lack of safety for people to just clarify what it is people do. Especially if you're working with a lot of different teams within your organization constantly, you might be dealing with a lot of people where you're like, “I know this person is on that team and that they're responsible for getting this from me, but I actually have no idea what the context of their role is outside of my relationship with them.”

CASEY: Sometimes I end up making a spreadsheet where I put it all the responsibilities and rows and we see which ones are filled, or not and who's doing all of the stuff in the middle. That's the best visualization I've seen is a spreadsheet for it. I wish there were more, or easier ways that more people could do that because it's really powerful. Once you see it, it's glaringly obvious it's happening.

ANNE: Yeah, absolutely. And I also think one of the dangers, though is people assuming, “Oh, well, because we're just adding copy to this design, that doesn't count as design work,” or we're assuming the PM, or the frontend person can handle that design work. But when we look at all of this persons over allocated, are they really going to do the best job to make sure that yes, this is the right place for the copy, this is how it works? Because even if we're talking like, “Oh, we just need to add one line of copy.” Okay. Cognitively, what does that do to the customer? Is somebody looking at the page holistically and thinking about it? And if you have somebody else, even if it's a small ask, who has a bazillion other things on their plate covering it, we can say, “Yeah, this is under this person.” But I think also, leadership needs to think about, “Okay, how have we resourced that person? Is that person really going to even be able to do that small task that we perceived because we don't need to fill in that design part of the sheet because it's something so small?” But I think that also comes from people not understanding the full value that some of these roles really provide outside of they produce a deliverable.

There's a lot of stuff where I'm like, “You really need somebody’s time for them to even consult on your team and not even bringing in an outside consultant, just somebody who maybe isn't allocated to your team.” So you would just come in and consult and be like, “Yeah, that's great,” or “Wow! You added that line. Your page was already – now it’s the cognitive load on that person is going to be this.” They're not going to read any of this and you're going to have a bunch of customers calling you, complaining. When you have somebody who basically has to do a drive by, yes, or no, that looks okay. You're not going to get the same service.

JACOB: On the other end of that, I'm a backend engineer and I think in a lot of places, I don't think in my company, but I think in a lot of companies, there's been an overcompensation of saying, “We have to really protect engineer's time. We have to really protect their focus. We shouldn't have any too many meetings.” I've never liked that, the typical engineer that they get a ticket and there's something that's not completely clear about what they're supposed to do and they just throw it back to the PM immediately.

That sort of culture has always just drove me nuts where it's like, “Sure, maybe we traditionally think of the PM's job maybe convene people, perform glue work.” If it's just this small, or medium question, why don't I do that?” Why don't I open a conversation and include my PM, but also talk to the other people that we need to get a question answered from so then I can unblock myself? I think there are some roles that necessarily have to protect “this is what I do.” I think there's other roles that are too protective of I only do this and could maybe stand to go outside their boundaries a little bit.

ANNE: I agree.

[laughter]

So much and I am very much a supporter of everybody owns the product. Yes, you have a product manager. Do they have certain expectations with their role about how they manage that ownership? Yes. Does that mean that your developers are just there to do a bunch of tickets and never provide product type of feedback? No. I really think you get better results, better products when everybody is able to have ownership over it. I think it sometimes gets into this Steve Jobs syndrome where you're like, “I am the genius of the team. I was hired to be the Steve Jobs of the team and I just tell everybody what to do.” Oftentimes, that results in a lot of crap and also it creates a lot of inefficiencies; the PM becomes the bottleneck, other things.

If you're really empowering your team and you're saying, “I led a testing and experimentation team for over a year and every Friday, we would go through the data.” My team would go through the data of all the experiments together because I'm like, ‘What is the point of them doing all this work to code up this experiment and then they just find out did it win, or lose?” They don't actually learn anything about what about the customer's behavior changed? Why do we think it changed? What problems do we think were in this? What do we iterate on this? And it really helps them not only have more ownership over the work that they did, it helped them be able to say, “Actually, I have this idea to iterate on this. I am not the person that wants to do everyone's job. I cannot come up with all the ideas in the universe.”

People come up with things where I'm like, “Wow, I really didn't think about we could iterate it on this way because of this information.” I really think that's also a big responsibility of PMs and other collaborative roles is to empower people to actually also have product ownership and I think there were days where the developer just does work and that's it, and don't ask questions you don't understand like what's going on.

But one of the jobs I joined years and years ago, a relationship that was between the development team and the design team was incredibly toxic, which actually coincidentally enough was also a thing where it was like a team based in New York with a team that was based outside the US. They would basically do a bunch of designs and send over a big Adobe file, I think an email with no layers, or anything in it to this development team and say, “Cool. Let us know if you have questions,” and the development team would work on it and then say, “Hey, we finished building it.” And then design would say, “Holy crap, this is terrible.” Like, “What is this?”

When I first joined, I was like – they really don't get along, first and foremost and number two, why are these things happening? I started talking to different members of each team to understand what's going on here and a lot of it was, there was literally no process for collaboration. It was no one talked to the developers during the requirements gathering, or during the design phase. So designers would just design whatever, without anybody there to give feedback to like, “If you do this, it's actually going to make us, have to do this call and it's going to add this many seconds onto the page and you're probably going to have a lot of people leave.” There was none of that kind of feedback loop.

The assumption was whatever we design can be done and the developers had feedback where they said, “We have tried to ask questions in the past upfront when somebody finally hands this off.” Oftentimes, it feels like people are speeding through trying to answer the questions, that people don't understand the question, or don't think it's not obvious what this is and they'll ask questions and they're like, “We sometimes get answers back that don't make sense to us and when we try to ask more clarifying questions, there's annoyance, dismissal.” So they basically said it is actually faster for us to just not ask any questions, build what we think needs to be built, and then just get all the feedback at the end than it is to try to ask questions throughout.

The fascinating thing about this organization, it wasn't the developers and it wasn't the designers, but it was like, leadership was definitely scared of Agile for some reason. I suggested maybe we should use some Agile methodologies and I got a massive amount of pushback [chuckles] that said, “We don't do Agile here.” I was like, “Okay,” and I instead decided to make some suggestions.

I was like, “Would people be okay if maybe three times a week, we just had a 15-minute meeting where we talk about what's going on in design and development and anybody else who needs to be involved can just join for 15 minutes.” And people said, “Well, yeah. That sounds like it's okay. No problem,” and I was like, “Okay, cool,” and I was like, “And maybe we could plan out the work that we intend to do in two-week increments and we could have a meeting towards the beginning of that two-week thing where we plan out together what's going to happen,” and people were like, “That sounds good. I like that. That sounds nice.” I was like, “As needed, at the end of these two-week things, we could talk about what went well, what didn't go well,” and people said, “Yeah, that sounds fine. Cool. We'll do that.”

The first time I implemented this on a project at that company, the designer at the end came to me and said, “This is the first time I've been able to use anything we built in my portfolio” because what actually got built was actually what the designers intended.

The thing is that there were things that the client said, “I want to change this in design,” and then the developers were like, “Actually, here's a problem and we could do this, but this is what's going to happen,” and the designer was like, “My special animation is not going to work. That was the whole point.” Like, “Why can't we do this? It should be super simple,” and they were like, “Well, you have to use this weird, special technology for this specific type of animation you want to do,” but having that conversation in the moment.

And I think they also needed to facilitate and maybe understood tech a little bit more than in that specific design team—there's some design teams that are much more tech savvy. Help them understand you can have something that looks like animation that doesn't use any special technologies other than what we would use for a standard website here and that you're not going to have to worry about knowledge transfer if somebody leaves, you're not going to have to worry about does anybody else other than this one developer know how any of this works, and also, it's going to be really easy to update every time there's a content change, which we know happens for this client pretty much every three to four months.

And that was something where it was like the designer was like, “I'm sad that some of the beautiful sparkles and things around the soap and stuff aren't going to be as flowing as I had anticipated,” but she was a lot happier than had the development team just decided well, we can't do that so now it's a static image. We basically implemented something where it ended up being this carousel and we're just like, “Just give us these images so that when they go through the carousel, it looks like this animation is happening.” Pretty much like when you could draw things in a flipbook and make it look like something's moving. Basically, the website version of that, which is much easier to maintain, much easier to update the content. It was just really fascinating because there was such this animosity and almost hate between the design and the development teams, but it was also like your bridges of communication are completely broken and nobody wants to change.

One team is like, “It's all this team's fault.” Other team is like, “It's all this other team's fault.” But also from a company level, they also previously didn't actually have someone in that role to help facilitate either and they were also definitely scared of trying a different process. They were scared of Agile when in reality, they actually had no problem with Agile. I think they just were scared that I don't know what was going to change their whole company process and I was like, “Just because somebody uses it one bubble isn't going to bring the whole company down,” and in fact, it worked out really well.

CASEY: I love that story. Yeah, small steps forward. You can make this incremental change to your team you're on. Anyone can do this on any level. You just might have to disguise it and do it very small. One step at a time.

ANNE: Sneaky Agile. Secret Agile.

CASEY: Yeah, secret Agile

ANNE: I’m going to brand it. I guess, I can't brand it because Agile is already trademarked. [chuckles] There'll be like an off-brand secret Agile.

CASEY: Early in my career as a frontend developer, I suggested we could do a design this way in one day, or this way that you want in one month and after I talked to everyone involved, they agreed two developers times four weeks times 40 hours was worth it for this. But I absolutely don't think it was. I think the designer didn't have 30 minutes to talk to us. That's a different cause here. But that happens, too. 30 minutes of a designer's time could have saved. Imagine the amount of money that was. Ooh. [chuckles]

ANNE: Yeah, and I think it goes back to what we were saying where it's like allowing everyone to have product ownership and if you're gatekeeping like, “Oh, we can't afford to have 30 minutes of that person's time,” or “We don't want the developer thinking about those things.” It actually takes longer and it actually results in less good product.

CASEY: Yeah. I visualized turbulence like if there's stuff going smoothly, it's just going. Otherwise, it's looping around, bubbling, and oh, all that wasted energy.

JACOB: I'm not a manager, but I've always felt like it would be better to, like you said, empower people to do what they need to get things done, even if they don't do so in the most efficient way, because then they at least know that they're empowered to do it. People are going to figure out and iterate on those fluid ways of navigating the organization to get what they need and you have to experiment to do that.

ANNE: Yeah. I think that's really a part of a culture of learning. People say they want a culture of learning and they're like, “Oh, here's a stipend. Go take this class.” But if you don't get a chance to learn it in your organization and try to practice it, it's all theoretical. Not saying theory isn't good, but it's the difference between, I don't know, I'll just say, I studied engineering in college. It's the difference between when you're studying engineering versus when you actually get out into the real world and work in a real environment. It's very different. You learn things, but there's things you have to adjust based on what is reality. Everything in theory tends to work, but that's in theory. Once you hit the real world, there are certain things where you have to adjust based on the situation and the context.

CASEY: Totally. They apply it. It’s like theoretical versus applied and you need to apply it. Hands-on workshops! But even better than that, having people on the team able to help support and coach each other.

ANNE: Yeah. I love that. I think that's something that doesn't happen enough is connecting people where it's like you want so-and-so to get stronger at this, this other person's really good at that, and that person needs to get better than this. Like, those are things where I don't think that happens enough.

I actually had a thing that worked today where somebody on our data team was like, “I was told to learn more things about product management” because they're like, “That's where a lot of this –” not that there's trying to become a product manager, but they're like, “It's going to help.” They're like, “It's supposed to help my career long-term to really be able to think about some of this data that I'm using, manipulate” I don’t want to say manipulating, but working with and thinking about it in a, I would say more so like customer way. I'll say more customer way because product can mean a lot of things.

My thing is unlike I'm a product manager, I've taken data science classes, I know just enough SQL to be, I want to say dangerous, but whatever the level below dangerous is and that's the thing is that there's things where I'm like, “Do I do those things day-to-day?” No, I don't. I look at some Google Analytics reports, I look at Tableau, I use a number of things, but talking to someone who actually knows how this works and does the work in this organization is going to help. And we were like, “Yeah. So we should set up time to regularly exchange knowledge, basically do a brain exchange so that I can learn more about this type of thing, data and you can learn more about product and we both benefit.”

ARTY: Maybe we need to change how we frame those conversations as to what we're here to do when we have these interactions generally. Because a lot of the times when things are framed in terms of oh, well, it's going to be a waste of their time. We don't want to infringe on their thoughts when they're supposed to be focused on these other things that framing that value proposition for everyone with respect to over the long-term, we're here to learn together and learn from one another. Even if during that time, what we get is a picture in her head of what this other person's context is like, such that over our careers down the road, we'll have a better picture in her head of what these other people's contexts are like. That has long-term value that far exceeds the cost of 15 minutes.

But if we don't frame things that way and we frame it as this disruptive activity that only has this short-term potential gain like we were talking about at the beginning of how we frame these relationships that we have, how we frame these conversations, those few minutes that are involved in that initial relationship set up create this snowball of effects over the long-term.

If we make an effort to think about how we want each of those relationships to go, if we think about what the value proposition is from a long-term perspective, and we make that the point, we're on the same team, I think that's the stuff that makes all the difference.

CASEY: I like this framing for you and the person you're talking to. Hopefully, the framing is there on your team. Hopefully, it's in the whole org. Hopefully, all the leaders have it. But if the framing doesn't sound palatable on some level, I see that happen a lot. It's like, we know this is good long-term, we know you and I, even our team, maybe the bubble, it breaks down somewhere. A lot of places, most places, I think.

ANNE: Yeah. I think it can break down for a number of reasons. One is again, trust and safety. It's really interesting, I saw someone on Twitter talking about this specifically for product managers but obviously, it can exist outside of that, where they said, “Once people get to a certain level in their product management career, they notice that there's a lot less learning, even product people do between each other in an organization.” I think some of it is certain environments are hyper competitive and people don't want to seem like, “Oh, they don't know that,” or “They didn't think of that.”

Again, I think some of it goes to this idea that—and not saying everybody believes this—but the product manager is supposed to be this genius like Steve Jobs and you're supposed to have all the knowledge and all the ideas and not everyone thinks that. But I think some organizations may people feel like scared of having that kind of exchange with somebody else in my discipline.

And then I think some of it also can be companies where they stretch people really thin. They're like, “I know this is my career. I have my little bubble, but I have no energy, or interest in going outside my bubble for that kind of thing.” It's interesting because I think a lot of these things – some of it is individuals, but I also think a lot of these things are different causes from a culture standpoint that leadership could shift.

Because at the end of the day, if you're exhausted, do you want to add one more meeting to your calendar? Do you want to do another thing if you feel like you're already doing a lot right now and you're like, “Oh, I should do this, but I'm tired”? Also, there's that again, sometimes it's imposter syndrome, or other things that make people feel like in this company, I don't feel safe going to somebody else and being like, “I don't actually know this. Can we talk more about it?”

CASEY: Yeah. A lot of companies, there's no headroom. There's negative headroom. You're already over overbooked in every way. Asking anything of that in that environment is a lot.

ANNE: Yeah.

CASEY: I love thinking on the organizational level. Glad you two don't mind going there. Jacob dropped off. It's really fun for me.

I'm just looking at the time here. So with reflections, we usually go in a circle. It's usually the panelists first and then we have guests give your own reflections. It can be a thing that was interesting, or memorable, something that will stick with you after the episode.

ARTY: So the thing that stands out for me, I think about where we started this conversation with superpowers, empathy, and collaboration. When you were talking about growing up and being an outsider where things were really challenging, but at the same time, you developed this ability to understand what it was like to be on that other side of the wall. Such that now you're significantly more aware of what's going on in other people's heads and how they're perceiving these relationships that are going on. It's like being able to have eyes of what it feels like to be on the other side of that wall.

We talked about contrast and these contrasting experiences from that to where in your home environment, you were loved and accepted as you are, and then in your journey and growth, you mentioned this desire for congruence to be able to be yourself in these different environments and why that was hard at the same time.

As you were growing in that way, that congruence became your self-actualization of being able to find this strength in yourself, this belief and trusting in your own voice so that you could stand up when someone needed to stand up. So that you could go against the grain and be solid within yourself. To be able to do things and step into these uncomfortable situations. To create change. To create culture. To shape leadership. To shape these handfuls of super important, critical conversations that frame the entire relationship moving forward from contrast to congruence and just seeing you blossom in that, seeing what you've been able to do, what you've been able to bring to the table as a human being, as part of the team was really amazing.

Your journey of how you got there just says so much about who you are and I hope listeners will be inspired of just really seeing how important it is to be able to trust yourself in those ways, to be able to find that strength and solidity within yourself so you can be someone that helps to contribute to moving things in a positive direction.

CASEY: Oh, it's beautiful.

So my reflection is a little on the coaching and DEI side. I said it earlier, too. I was very excited about this idea. I used to think DEI was not something I could help with because I'm a white man. What am I going to say to anything?

But I do have the clear lens that gives me some kind of minority perspective that’s really valuable and white people, especially conservative white men, are more likely to listen to me, it's my power. So I'd like to wield that and do things like skills training, workshops, and coaching including for diversity, equity, and inclusion. But I never thought about specifically coaching people on DEI, making that content. I don't know why, because I don't know. All the formats of everything else that I do, but it was just like a light bulb went off in my head when you said it's like therapy, it could be talking through problems.

So I want to think about that more. Maybe we can talk another time about that. What would it look like? What would make it look successful? What would be helpful? Who could ever pay for it? Even companies, I hope. How do we really help people change and grow, the people who are motivated to? That's what I'll be thinking about after this episode.

ANNE: Yeah, I think that would be wonderful. I think mine is more of like a final message, really. It's a reflection, but it's more of, I think reflections of how am I feeling than necessarily a specific topic.

It is related, but it's been a wild nearly 2 years in this pandemic and I really think the future of where we need to go as a society, which also being in a tech driven society, is very important for people in technology to consider is how do you bring what you love to the table? I'm not asking you to be exploited by your company—and sorry, this is going to be very hippy-sounding—but if more of us showed up with love in terms of how we build our products.

Not just like, “Oh, I really love just building the product,” but also, love for the people who we're building it for and the people who will be impacted, but maybe we're not building it for. Showing up with love in terms of how we're treating ourselves that day and how we can empower others to be their best selves in our bubble, or when we have influence beyond our bubble, and really reflecting how you can show up in some of these environments where you can show up with more love and create safe and trusting environments. Because I truly believe just because it's digital doesn't mean that what you put in it doesn't impact the outcome.

If you put trash inside of a sausage, it's going to be trash in a sausage casing. If you put all your negative energy [chuckles] and disdain for what you're doing, or your team, or you just sort of like, “I don't care.” There's going to be things where obviously, you're going to work jobs just for a paycheck, but figuring out in which ways can you show up with love in that environment and whatever that means to you. That's my final thought for the day.

CASEY: I love it! Thank you so much, Anne for joining us here.

ANNE: Yeah, thank you. It's been such a pleasure to talk to you and talk to you about these things. You said earlier in our conversation, “It's great hearing these things from somebody else's mouth reflected back,” and that's how I really feel about this where I'm very passionate about these topics and being able to talk to other people and hear them value that as well means so much.

CASEY: Yeah. You're not alone. You're not crazy. You're not having ridiculous thoughts. You see somethings very clearly and you could enunciate them, articulate them, share them. I’m so glad we got to do that together today. All of us!

ANNE: Yes, yes. I’m incredibly grateful for this. It is such a pleasure.

ARTY: Well, thank you again.

Special Guest: Anne Griffin.

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