FAQ: How to disagree productively, know which hills to die on, and find your mentors with Ashley Murphy

Hi, everyone, we're starting a new WorkLife series today called frequently asked questions where I answer questions that I get all the time from listeners, glue clubbers, strangers I meet standing in line, and so on. To kick this off, we're actually going to start with questions from Glue Club, which is a leadership development community I built for leaders in fast changing companies. In those contexts, things are moving so quickly that you rarely have time to consult the business books. So today's questions reflect some of the topics people confront while learning in real time. We're also opening up an easy way to write in and ask your own questions that we might feature on a future episode. You can ask a question or share a story that you'd like my perspective on by sending a voicemail to 347-377-2938 or reaching out to worklife@ted.com. I'm Molly Graham, and this is WorkLife, where we untangle the messy human side of work. So to do this, I'm also going to introduce you to a special co-host, Ashley Murphy. Hello. Hello. All right, Ashley, now I'm gonna read your bio, which I know is going to make you uncomfortable, but we got to have people get to know you. Here we go. So Ashley and I have worked together for a while now. We first met when I was at the Chan Zuckerberg Initiative. And then when I started Glue Club, she was one of the key people that helped create and shape it. Since we started working on work life, Ashley has been my right hand, helping me figure out how to shape this season. And one of the things we both agreed on is that we really wanted to create a community around work life. So today I asked her to come on and help get that started. Also, just to say it, Ashley is one of those special people who cuts right to the heart of any topic. She's someone you can trust to always tell you the truth. And even if it's uncomfortable, she'll often make it funny. I usually say she's like a torpedo wrapped in a marshmallow. I'm excited for you to get to know her. So Ashley, welcome to work life. Thank you for having me. That has been cracking me up all weekend. Torpedo wrapped in a marshmallow. I am glad to be here in any form, including that one. It's how everyone describes you, right? Always, always universally. Okay, Ashley, where are we starting today? Okay, so here is our first question that someone actually brought up really recently. They said, I'm struggling because I work for a CEO that I respect, but I honestly disagree with a lot of the decisions that she's been making lately. How do you work for someone when you disagree with them? And how do you execute on decisions you disagree with? So there's a lot in there, Molly. What's your first thought? I have a couple thoughts. And this is a question that comes up a lot inside of Glue Club. Because you don't ever work for someone that you agree with all the time. That's not a thing. And I think the question is, how do you disagree productively? And there's this framework that I think was popularized at Amazon, but I don't actually know, called disagree and commit. And the idea, I actually learned about it on Knolls, which is the outdoor program that I led when I was my first job out of college. And Knolls had this really famous story about somebody, a group of people having to make a decision about which way to go on a certain route. And they would talk about disagree and commit because somebody like really, really disagreed with the decision. They were debating it and debating it. And finally, the group made a decision to go a certain way. And the guy went and sort of led the next section. Like he had been the person that had most violently disagreed. And he chose to kind of fully commit with his whole body in the case of this by, you know, leading that next section. But I actually think that the truth is that it's really hard to do that, to actually commit with your whole body when you disagree with something. And what I've found to be more helpful as a framing, just in terms of how you're thinking about how you lead when you're not sure about the decision that's being made, is what I call disagree and let's see. And I just want to say, I don't mean that in a passive aggressive way. I don't mean that like disagree and let's see, you know what I mean? Like, I'm gonna go along with it, but I'm gonna undermine you. No, I mean like, actually the truth is that most of the time no one knows the right answer and you're just picking a path forward. And, you know, honestly, sometimes it's the best of two bad options. But in general, everything inside of companies, particularly startups, is an experiment. It's just like, no one actually knows what we're doing. So are we gonna try A or B next? So how do you approach something as an experiment and think like, okay, I'm, you know, I've fought my fight and we can talk about, we can talk about fighting and how to sort of disagree productively. But at some point you have to pick a path forward and you have to just say, all right, let's frame this as an experiment. Let's, I'm gonna try your version. Let's agree on how to measure the experiment, right? How are we gonna know on what time horizon and by what metrics are we gonna know if it was right or wrong? And then let's try it and let's just see what happens. And then, you know, we'll know more, which really is honestly, I think the best way to approach a lot of stuff in startups. It's just like, everything is sort of, what's the next best choice we can make. That makes sense. And it's a good reminder. I think we get so caught up in who's right, who's wrong, as opposed to we're in this experiment together. What can we learn from this? I will say when you first said it, I thought, you know, disagree and let's see, could come out really positively, could come out a little passive aggressively, right? And so how do you really think about the difference between how you show up and how do you make sure that you're really embodying that genuine, let's see curiosity versus that passive aggressive point of view or mentality? Man, that's such a good question. The truth is we are all humans at work, right? And so when you're dealing with a decision where it can often feel really emotional. So I'm like taken back to this moment in my journey in one of my last jobs where the CEO came to me and said, I think we need to do a layoff. And it was not a small layoff. It was like 30% of the company. And I remember having this just extremely strong no reaction. And I don't think I like on the call was like, no. I was like very upset. And, you know, we had that first conversation and he talked me through his logic. And I honestly can't even remember what we talked about on that first call, but I think I basically said like, let me go think about it. And I just, I remember having multiple weeks of like a pretty emotional reaction to it. Just, it wasn't, I felt a little bit like it wasn't what I had signed up for. And it took me like a couple of weeks and a conversation with a coach and obviously like continued conversations with him to get to a place where I could get out of that headspace and get into a place of, okay, I get it. And I, it might not be what I wish was the right answer, but I think it was, then it became a journey for me of like, okay, how do I do this in a way where I can feel like I did my best in a sort of terrible situation. And I do think a lot of times you have to shift your energy to, I'm gonna make the best of this. I'm gonna figure out how to do my best, even if you have reservations, right. But that sort of like sense of like, okay, like I understand the pros and the cons here. I've thought about other options. Maybe there's an option I would prefer, but for whatever reason, that isn't going to happen. And we've chosen this path forward. So I'm going to lead through it. How do I get to a mental state where I can lead through it in the best way possible, where I feel like I can be the best version of myself in this, in my case, shitty situation. That is a really powerful story. It really helps me understand the mindset that you had to get yourself into to be able to work with integrity, still be a good leader, in respect to the CEO's decision, but also navigate some of that discomfort. So I really appreciate you walking us through that. And it also makes me think of another question, which is in this case, disagree, let's see that was the right choice. But sometimes you're just pretty sure that this is actually worth the battle. This is worth the fight. And so in these moments, how do you still show up with high integrity and in a very professional way when you know that you need to fight for what you believe is right? And how do you know when it's time to let go of the fight? Yeah, such a good question. So when I was going to go work at the Chan Zuckerberg Initiative, I had this mentor named Patty Stonesifer. And she, Patty ran the Gates Foundation for 10 years. And so when I was, you know, deciding to take the job at the Chan Zuckerberg Initiative, she was one of the first people I called because they're pretty similar. And I don't remember what the context was, but she told me this really wonderful framework that I've now carried with me and stolen and made my own, which was, she said that she had this that culture is, for the most part, set top-down. And I don't mean that in a prescriptive way. I actually mean that I spent a lot of time trying to change the culture at Facebook or influence it, and I realized that that's not how culture works. Culture is actually built in the image, literally the personality, of the person that founded the company. And this is particularly true in young companies, you know, in their first 10 or 15 years. You often, to understand what it feels like to work inside a company, what you need to do is a personality diagnostic on the founder. You need to be like, who is this person? What are their greatest strengths? What are their greatest weaknesses? And you will pretty quickly get a description of the personality of the company, at least to like 80% accuracy. And, you know, to go to the Facebook example, I would say Mark is, and, you know, one of his both greatest strengths and greatest weaknesses is he's an extremely competitive person. He's very aggressive. Like he, he's just in general, Facebook felt like a, you know, sort of a masculine, aggressive, competitive organization. None of that was in the original values. And it did actually come through in some of the stuff that he started to write down in a way where I was like, oh, this is not my natural style. It's explaining to me why I feel uncomfortable here some days. And also I think it's honest, you know? Um, so the, the point of all of this is just to say that like, there are some things that are going to be unchangeable inside of a company. Trying to change culture in a founder-led company is like, I mean, it's basically like you're married to someone. How much do you believe they're going to change? Do you know what I mean? People can change a little, but they're not going to change a lot. And I think you have to be honest with yourself about that when you're picking where to work, you know, let alone when you're fighting certain fights about the right way to tackle things or the right way to disagree or whatever, you know, the right way to lead a company. Um, at the end of the day, the founder and the CEO define a lot of what it means to work somewhere. And you have to just be cognizant of that when you're picking what to fight about. And when, most importantly, I would say when you're picking where to work because a lot of that stuff just isn't going to change. So that actually, does that actually answer the question that you asked? I really think it does because I think sometimes we get so caught up in just what is the, you know, quote unquote right decision based on what makes sense for the company. But we, and we analyze that so much, but we don't think about, well, who is this founder? Who is this person that built this and made these decisions? And based on who they are, what's likely to shift, what's likely to change, what's likely to be open for debate. And I think if we only analyze the company and not the founder, it can lead us towards some really futile battles that we can have day-to-day. So it makes a lot of sense to me. Yeah, it's so real. And I really think the more senior you get and the further along in your career you get, the more you're making a decision about like, do my values align with the values of this company and this person? Like it's, you know, I think when you're earlier on, you can, you can work somewhere and so much of your job is to learn and to figure out who you are and to figure out what your values are. But the farther along you get, like certainly for me, like I've had to say, do, is this a place where I can sort of effortlessly do my best work because my values are aligned with the company or the founder and, and, you know, sometimes that's just not the case and you have to turn the job down or you have to leave the company. That's a good reminder too, just in terms of for folks that are writing their own values or their company's values. It was interesting that you said that the process of helping Facebook define their values actually showed you where you weren't aligned. And I think often folks write their values in a way that's meant to be inviting and inclusive for everyone. But it sounds like you found some value, some value, no pun intended, but you found some value in values that actually actively repelled people that were opinionated enough that some people did not fit in and did not align. And that was valuable for you. Yeah, totally. Well, and you know that one of the things I believe, this is actually something someone said to me when I was working on culture at Facebook was like that the best culture is actually repellent. Like this guy, Marcus Buckingham, who's written a lot of the strengths books and is a brilliant sort of leader in strengths-based work, consulted for us at Facebook. And he said, I really believe that job descriptions should be repellent. Like the idea is that you should be writing a job description to attract the like five people that are perfect for it on earth. Instead, we write job descriptions trying to make every job sound like a sexy person that you want to date. Everyone should want to date this person. It's like, oh, this is the best job in the world. But actually, your time is much better served if the job description, like a lot of people read it and they're like, ugh, I would never want that job. And the same is true of culture. Like it's so much better to be honest about who you are and who fits and, and really up front about that. Actually try to kind of like anti-sell people a little bit. And then then the people know what they're getting into, right? And they can make the right choice for them versus trying to make yourself sound attractive to everyone. Makes sense. I think you're, you're one of the biggest believers in the whole clarity is kind thing. And I think it applies to job descriptions. It applies to values. It's just the through line throughout so much of what work is. Okay. We are ready for our second question. This person said, I think I need to hire an executive coach. How do you know you need a coach and how do you go about finding the right person to coach you? Such a good question. I get a lot of emails from people asking that question or a question like that, you know? And the first thing that I do is I think it's really important to distinguish between three different types of support. Like, first of all, I'm the biggest believer in the world that every leader in the world should have support. And I think that is a really good and important thing to look for, particularly the more and more senior you get, the less likely you're going to be able to find support from peers inside your company and things like that. So there are three different types of support that I think are worth evaluating what it is that you actually really need in this moment. The first is a therapist. The second is an advisor. And the third is a coach. So a therapist is someone that is going to sit down with you and they are trained. They have, you know, either a PhD or a master's in helping you try to unpack your past, your parents, your family, your biography. I like to call it your programming. What is it that's made you the way that you are? That is great work to do. It's really important. Every manager in the world would be better served by having done a bunch of therapy because things can trigger you, right? That come from your programming and your biography. And I would say that therapy is a great foundational thing to do as a human, but it's important for work too, right? Work, our programming comes with us everywhere. So the second type of support, I'm actually going to go to coach next because I think coach and therapist, they, they can be cousins at times. A coach is someone typically that has training, a certification or something like that. But a lot of what a true coach does, someone that is trained in coaching, is help you learn how to draw answers out of yourself. They are there to ask you really insightful questions that will help you get to the right answer for you. And they bring frameworks and they bring models and, you know, things that they've learned through their training, but they're there to really like help you deeply understand who you are as a leader and how you want to show up, but also how do you be the best version of yourself? And it can, it can connect at times to therapy because, you know, sometimes you're like, why am I so triggered by this person? And you dive into that with your coach and what you find is, oh, they remind me of my dad or my mom or my, you know, some triggering person in the past. So that, that is how I think about coaching, which is someone that is really, you know, a talented coach is going to be someone that helps you draw answers out of yourself. An advisor is someone that I think of as they have been there before. They've probably walked, you know, steps ahead of where you are in your journey, but they are someone that honestly has a lot of answers for you. Like they're someone that like, you could be like, what should I do? And they'll be like, here's my opinion. And that is actually very different than a coach. Like uh an advisor is someone that has specific experience that you can really learn from. You can go to them and say, which system should I pick? You know, something as tactical as like which tool should I pick in this situation? All the way to like, what have you done in the past when you've experienced this? But really Board of directors, if you want to call them that. That makes sense. I mean, I like that combination of this, you know, spirit of generosity and abundance and also this very tactical thing that, you know, anyone can do as they're thinking about leaving a job or hitting a milestone. That combination really resonates for me, for sure. I have one more question about the coach specifically. Have you had a coach that really stands out to you as excellent? And what is one thing, if so, that that coach has taught you? So I've actually had two phenomenal coaches in my life. And the reason I want to say that is because I do really think that different phases of your life ask for different types of people to help you. So when I was at CZI, I got this coach named Maggie Hensel, and she helped me through CZI. She helped me through my post-CZI really, like for, I think, five or seven years. And Maggie was extraordinary. I learned so much from her. She really made me more aware of who I wanted to be as a leader, but also what the work I wanted to do in the world. And I wrote an article on my Substack lessons based on something she taught me about, it's called the sandwich metaphor. And she has this idea that, like, basically, you have to think about where you get the most value in delivering impact to people, sort of like where is it that you feel most at home? And her metaphor is basically like a soup kitchen where it's like, do you get the most value out of being on the street handing out sandwiches? Do you like being in the kitchen making the sandwiches? Are you the person that likes buying the groceries and enabling the sandwiches? Do you want to fund the sandwiches? And that was just like a very helpful metaphor for me for a bunch of the time of realizing that, like, I'm much happier when I'm closer to handing out the sandwiches than I am, like, funding the sandwiches. Anyway, that, I feel like that has helped me frame a lot of interesting decisions in my life. And it's like the difference between Patty Stonecipher, who I mentioned earlier, who, like, you know, had direct experience that was so valuable to me to learn from versus like Maggie, who'd like never worked at CZI before but could help me think through how to detangle problems on my own, you know, and things like that. Now let's talk about your therapist. No, I'm just kidding. Perfect. OK, here is our next question. This person said, I am looking for a job, but I'm having trouble telling my story as a generalist. I am someone who's known for being able to solve complex problems at work, but that doesn't perfectly map to a specific functional job title. How can I effectively tell my story and be appropriately valued for my experience? I know why you picked this one. So this is something we talk about a lot inside of Glue Club because, well, I think people look at me and think Molly is a generalist. I think anybody that's had, like, the chief operating officer title, people think, oh, they're like the highest level generalist you can get. And I just want to say, I actually believe there's no such thing as a generalist. Like, I know it's nut balls coming from someone like me who leads a community and invests a lot of time in sort of, no matter what tier you put them in, they're always going to think what's right for the company and what do I need to do next and what do we need to do next. But honestly, like, I am a specialist. Like, I may have very generic titles. I may actually not fit in a functional box, right? Like, I'm not a marketer and I'm not an engineer and I'm not a salesperson. I can do all those things, but I'm not the best in the world at any of them. But there are things that I'm the best in the world at. And when somebody calls me about a job, I'll listen and say, yeah, you should never hire me to do that job, right? Somebody called me once about a data team, and they were like, our data team is broken. I think I'd been talking to them about other roles at the company. And they were like, well, here's a problem I have, which is like my data team is broken, and I really think you could come in and you could like run the data team and you could like. And I was listening to it and I honestly almost burst out laughing on the call because I was like, I am not good. Here's what I would be great at. I would be great at coming in, figuring out what's not working, trying to identify what your data team is even for and what role it's supposed to play in the organization, and then finding you the right leader for the data team. That is something I would be among the best in the world at. But leading long-term, leading a data team, like, girl can barely do math. So, like, let's not play. So the point about the generalist is, like, I actually believe every single person in the world has a specialty. And your specialty may not have a functional description, right? Like, it may not be, again, head of sales, head of marketing, whatever. But there's something that you are uniquely good at. And your job when you're thinking about telling your story or helping people understand what to hire you for is getting really good at explaining what your specialty is. And, you know, the way I help people do that when I'm talking to them about this is you want to sit down and think through, you know, two or three experiences in the past where you felt like you were at your best, things that you look back on and think, gosh, I'm so proud of that work, but also I really felt like this was the highest and best use of me. Like, I felt fully utilized or just, like, I don't know, like, at my best. And you can write down that story. Usually I just have people tell me the story of, like, what, tell me the story of, like, a time when you felt like you were doing your best work. And pretty quickly patterns pop out. You know, I did this with someone the other day, and he was describing it to me, and it was very, very different jobs. Like, you know, one was at a philanthropy and one was at a for-profit education company and something else. But what he described was a really clear pattern of someone that really likes vague, ambiguous problems, not clearly defined things, going in, having, you know, the right tools at their disposal, but basically wading into, like, chaos and figuring out the right path forward. And as he talked, like, it was just very, very obvious that there was a set of jobs where it was like, ooh, pick me, you know? And then a set of jobs that were like, yeah, never hire me to do that. You may not be able to easily say, like, hire me to be your head of marketing or, you know, your head of engineering or whatever. But you have something that you are uniquely good at, and you need to help people by being able to describe that and saying I'm a generalist or even using titles in general. Like, I definitely find that, you know, folks in our operator communities, like the operators in our community, will say I'm a head of business operations or I'm a head of revenue operations. And I'm like, that's not a thing. Those titles don't mean anything. They mean something different in every single company. You need to find a way to describe what you're good at that has nothing to do with a title because what you are good at is solving a specific set of problems with a specific set of tools. And you've got to be able to describe that for someone so that they can listen to you and say, ooh, I want that, you know? Or, ooh, you fit or no, you don't fit. You're not what I'm looking for. The best thing in the world is finding a job that's, like, uniquely yours, right? That you're like, I can crush this. And the only way to do that is if you can start to describe, like, your specialty. Okay, that's it for our FAQ. Thanks, Ashley. That was fun. That was fun. All right, so let us know if you liked it, and you might hear more of these in the feed from time to time. Make sure to submit your questions or experiences by calling us at 347-377-2938 or emailing worklife@ted.com. We can't wait to hear from you. Work Life is a production of TED and Pushkin Industries. This episode was produced by Isaac Carter. Van Banhengchang is our story editor. Mixing by Hansdale Xi. TED's executive producer is Daniela Balarezo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Hy-Lash, Valentina Bohanini, Lainey Lott, Tonsica Songmanivong, and Ashley Murphy. If you like the show and want more, come join the discussion on my Substack lessons. I'm Molly Graham. Thanks for listening.