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Worklife with Molly Graham

9 Jun 2026 · 42m · 10 chapters

Episode artwork

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

In short

How to disagree productively with a respected CEO, decide which fights to keep fighting, and find mentors/coaches; also how to recognize founder-led “unchangeables” and how generalists should tell their story.

Guests

Ashley Murphy, Molly Graham’s co-host and long-time collaborator (helped create Glue Club; right-hand on Work Life). Ashley previously worked at Facebook (HR/culture and employment branding) and has mentored/led in leadership development contexts.

Key claims

Disagree and “let’s see” by treating decisions as experiments with agreed metrics and time horizons. Fight “any fight” up to three times using different tools (peers, outside advisors, board/360 data) then let go if timing/authority won’t change outcomes. Culture is largely top-down and reflects the founder’s personality; use founder-fit to avoid futile battles. For support, distinguish therapist (unpack programming), coach (draw answers out), advisor (experience-based guidance); “mentor” often functions like an advisor. Generalists have a specialty; tell stories of peak impact and the problem-types/tools you’re best at.

Notable examples

A 30% layoff decision Ashley faced at a prior job; Mark Zuckerberg rewriting Facebook values; Patty Stonecipher’s “fight three times” rule; Ashley’s “sandwich metaphor” coach lesson (soup kitchen roles).

Written by AI. May contain mistakes.

Chapters

4:06

Introducing Guest Co-Host Ashley Murphy

Molly introduces Ashley Murphy and their collaborative work on the podcast.

“Now I'm going to read your bio, which I know is going to make you uncomfortable, but we You got to have people get to know you.”
5:56

Disagreeing with a CEO

Discussion on how to handle disagreements with a respected CEO and the concept of 'disagree and commit'.

“And this is a question that comes up a lot inside of Glue Club.”
8:38

Navigating Difficult Decisions

Molly shares a personal story about processing a difficult layoff decision and maintaining integrity.

“It's just like everything is sort of what's the next best choice we can make.”
11:23

Knowing When to Fight for Your Beliefs

Exploring frameworks for knowing when to stand firm in disagreements and how to approach them.

“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, intersect the CEO's decision, but also navigate some of that discomfort.”
14:00

Effective Disagreement Frameworks

Learn how to effectively disagree within your organization by utilizing a structured approach.

“report to you and you are making the case to your manager that they need to tackle that.”
16:02

Understanding Company Culture Through Leadership

Explore how leadership styles and values shape company culture and influence employee experiences.

“And it's helpful because I've definitely gotten stuck in those loops where you just feel like you're having the same chat again and again and again.”
21:41

Aligning Personal and Company Values

Discover the importance of ensuring your values align with your company's culture and leadership.

“But we analyze that so much, but we don't think about, well, who is this founder?”
22:56

The Role of Repellent Culture

Understand how a culture that actively repels certain individuals can actually be beneficial for organizational fit.

“It was interesting that you said that the process of helping Facebook to find their values actually showed you where you weren't aligned.”
28:00

Understanding Support: Coaches, Advisors, and Mentors

Learn the distinctions between coaches, advisors, and therapists, and how to find the right support for your leadership journey.

“This person said, I think I need to hire an executive coach.”
44:15

Telling Your Story as a Generalist

Learn how to articulate your unique skills and specialties effectively.

“This person said, I am looking for a job, but I'm having trouble telling my story as a generalist.”
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Transcript

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2:59Hi, everyone. We're starting a new work-life 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.

3:38You 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 at ted.com.

3:59I'm Molly Graham and this is Work Life, 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 going to read your bio, which I know is going to make you uncomfortable, but we You 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.

4:40And 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.

5:20So 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.

5:59And 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 Knowles, which is the outdoor program that I led when I was my first job out of college. And Knowles 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.

6:34And 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 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 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.

7:23And 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 going to go along with it, but I'm going to undermine you. No. I mean, like, 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 going to try A or B next? So how do you approach something as an experiment and think like, okay, I've fought my fight and we can talk about fighting and how to sort of disagree productively.

8:10But 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. I'm going to try your version. Let's agree on how to measure the experiment, right? How are we going to know on what time horizon and by what metrics are we going to 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.

8:46I 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?

9:20And 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.

10:03And 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 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?

10:46And I do think a lot of times you have to shift your energy to I'm going to make the best of this. I'm going to 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?

11:23That 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, intersect 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?

12:03And 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 have this mentor named Patty Stonecipher. And she, Patty ran the Gates Foundation for 10 years. And so when I was 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 rule with Bill and Melinda and Bill Sr.

12:44that she would fight any fight three times. And if she lost after the third time, she would give up. And there was a bunch of nuance to what she said that I've found really helpful. The first thing that she said was that you couldn't fight the fight the same way each time, right? So like the first time you fought it, it might be like you trying to make the case, you know, her trying to make the case to Bill, you know, or one of them about what she thought was right. And, you know, for all of us that have disagreed, it's like you go, you make the case to your manager that, you know, so-and-so needs to be fired or such-and-such decision is the wrong decision.

13:23But then you have two more chances. Let's say that they absorb it but don't change their mind or don't immediately act on what you argued for. You have two other options. And her point was you got to use a different tool each time. So what other tools do you have at your disposal that might be helpful in kind of making the case for the thing that you think is right. And those tools can be like an outside advisor, a board member, someone that the CEO or your manager listens to differently than they listen to you, other peers. So a classic example would be like someone is underperforming that doesn't report to you and you are making the case to your manager that they need to tackle that.

14:05Other data points from within the organization about other people saying, hey, this person's underperforming, or employee data. So like, you know, a 360 on that leader, or just, you know, employee engagement data. Anyway, data, outside advisors, peer feedback, all of those are different tools you can use to try to make the case again. And, you know, Patty's point was actually that like, she only got to the third time, I think once in her career, or in her time working at the Gates Foundation, which is pretty interesting. But you know, I think for those of us that maybe aren't as powerful as Patty, like it is just also a helpful framework to think like, okay, I have three chances to make this fight or sort of make this case, right, for this thing that I believe in or against this thing that I disagree with.

14:52And then at some point, I actually just have to put it down. I have to say, okay, I have made this case three times. And at the end of the day, this isn't my company or it isn't my decision. It's my manager's decision or it's the CEO's company and I need to let it go. Or maybe now isn't the right time. I was talking to somebody the other day who said that they had made this case for something they really believed in multiple times at their company and nobody was listening to them or people were listening, but they didn't feel like anything was changing. And I was like, well, is it possible that now is just not the right time for this battle?

15:29That people might agree with you and it might not be possible to do this right now. So anyway, timing also matters. You can pick it back up again, you know, in six months or 12 months and it's a different company. But I just think that idea of like using different tools, giving yourself a constrained amount of tries or time to make a case and then choosing to say, okay, you know, obviously I'm not going to win this right now and it's time to move on and sort of lean into whatever the decision is at this moment. That makes a lot of sense. And it's helpful because I've definitely gotten stuck in those loops where you just feel like you're having the same chat again and again and again.

16:09So the idea of over and over, it's draining for everyone. So the idea that you can put a constraint around how long you spend on it and a reminder that you have many tools in your toolkit, super helpful to me to hear about. Yeah. Okay. So we talked a little bit about how you can disagree effectively and professionally with high integrity. but I want to go into how you might be able to forecast the outcome of the disagreement itself. I know we can't predict the future, but are there any signals that you see that help you differentiate when a scenario could change because of who the CEO is or how they naturally lean, or a scenario where you probably are just going to need to go ahead and accept things as they are?

16:52Yeah. You know, so this is one of those ones that I learned experientially. Like, So when I was at Facebook, I worked on culture, whatever that means. So my job in HR was basically how do we talk to people outside the company about what it's like to work here, which is like employment branding. And then Mark Zuckerberg gave me this question, who do we want to be when we grow up? And I summarized that as culture. But a lot of that was working through both for myself and with leaders at the company, who are we and what is changeable about this place and what is immovable. And I had this really interesting experience where Mark came to me and Lori Goller, who is the head of people at Facebook for a very long time, and said, I want to rewrite the values.

17:48It was in like 2009, I think. And we actually had a set of values that he hadn't written. So now that I look back on it, it makes complete sense that he wanted to rewrite them. But at the time, I was like, what? You can't rewrite values. That's not a thing. Values are things you etch on the wall and unchangeable objects. But I realized that he wanted to have a conversation with the company about how we needed to grow up and how, for example, move fast and break things, which is sort of Facebook's very famous informal motto, was different when we were 80 million users and smaller than MySpace and that it was changing now that we had a platform where a whole business is dependent on us and things like that.

18:31So anyway, it was really interesting because the process of working on this new set of values was actually the process of Mark writing down who he was and what he wanted to build. And I remember one version of those values, he wrote down and I looked at them and was like, oh, I'm not sure I belong here. I think it both really clearly explained Facebook to me in terms of what it felt like to work there. and it was uncomfortable for me because it wasn't my values. You know what I mean? It was like, it was his values. It was who he was. And it actually working on that with him really taught me that culture is for the most part set top down.

19:22And 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 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.

20:00And you will pretty quickly get a description of the personality of the company, at least to like 80 % accuracy. And to go to the Facebook example, I would say Mark is, and one of his both greatest strengths and greatest weaknesses, he's an extremely competitive person. He's very aggressive. He's just in general, Facebook felt like 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.

20:38And also, I think it's honest. So the point of all of this is just to say that 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, let alone when you're fighting certain fights about the right way to tackle things or the right way to disagree or whatever, the right way to lead a company.

21:18At 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. 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 them for the company. But we analyze that so much, but we don't think about, well, who is this founder?

21:54Who 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 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.

22:37But the farther along you get, like certainly for me, like I've had to say, 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, 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 to find 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.

23:12But 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.

23:46And he said, I really believe that job description 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. It's so much better to be honest about who you are and who fits and really upfront about that.

24:20Actually try to kind of like anti-sell people a little bit. And then 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. It makes sense. I think 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 a through line throughout so much of what work is.

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27:58Okay, 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. 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.

28:40So 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 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.

29:26And I would say that therapy is a great foundational thing to do as a human, but it's important for work too, right? 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 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.

30:07And they bring frameworks and they bring models and things that they've learned through their training, but they're there to really 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 connect at times to therapy because 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 some triggering person in the past. So 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.

30:46An 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 there's 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. 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? Something as tactical as which tool should I pick in this situation? All the way to what have you done in the past when you've experienced this?

31:28But really what they're going to help you with is their own experience. They're going to come at it from like, hey, here's what I've done and seen in the past. The reason I think it's really important and valuable to distinguish between these three things is like when you're going to go out and market and look for support, you really want to figure out what it is that you want. Do you want someone that's going to come to you and tell you what to do? Or do you want someone that's like going to help you strengthen your own sense of knowing by asking you a lot of really smart questions and helping you grow more and more in the market?

31:56I will say there's like advisor coach hybrids, but I'll spend, you know, I'll talk to founders and they're like, I really think I need a coach. And when I dig into it, they're like, actually, really what I want is an advisor. I want someone that's seen this before that's going to tell me what to do or what they would do. Get the best version of one of those versus trying to find both of them in one person. That makes a lot of sense. Getting specific, I can imagine, can really help you here. So understand the therapist, understand the advisor and the coach. Where does mentorship fit in here? As a mentor, is it typically one of these three types of a role?

32:33Can it be a hybrid? What does that look like? Okay, mentor. Mentor is, for me, what I call a black hole word, meaning you can use the word mentor and I can use the word mentor. Like you come up to me and say, I want you to be my mentor. And my next question is going to be like, what do you mean by that? Because I think it's kind of a word that doesn't mean anything. Everybody just has a different definition of it. So I'll give you my perspective on mentorship, which is I actually think mentorship for the most part, at least in my life, has really fallen into the advisor category. Sometimes the coach category if it is a certain type of friend.

33:09But basically all my greatest mentors have come from people that I've worked with in the past. They've been people that have been my boss in the past or been like a really strong peer in the past or sometimes even someone that's worked for me. and they've just been someone that I really value. I turn to them for advice at certain times in my life where I've just really valued their opinion and their perspective. And slowly over time, all that I've done is just identify someone that has those qualities and then stayed in touch with them. People talk about the idea of a board of advisors, almost like you should hire people into roles on your board of advisors.

33:46For me, it's been a lot less formal than that. It's just been probably a set of 10 or 15 people that at different times, each one of them is valuable to me in different ways. And I have built really deep two-way friendships with these people. And they're folks that when I'm stuck or I am making a decision or whatever, I feel like I can call. And I know that they feel the same way about me. And for me, it's really been important that there are people that have worked with me in the past that do know me because that just means that I feel seen when I'm asking a question or making a decision. I was considering a job a couple years ago and I was talking to random people about it, people that didn't know me as well.

34:34And everyone was like, oh my God, you should totally take that job. That job is so cool. And everyone that really knew me, like my true, I guess, mentors or or truest friends. We're all like, absolutely do not take that job. Like you, that is you making a mistake that you have made multiple times. Let me give you all the examples. So to me, that's the value of like, I don't know if they really fit into a perfect category, but the truest form of friends, the friends that can really advise you, the friends that know you and see you are the ones that, you know, have, have been through stuff with you in the past that, that deeply know you, right?

35:07They're not just giving you generic advice. So I would say the best place to look for that, which again, I think probably falls mostly in the advisor category, is folks that you've really worked with in the past or at least built some kind of work relationship with in the past. That makes sense. And I heard you say somewhere in there that you have 10 to 15 of these people. And I have noted this to be true. You've got a lot of folks that you can really rely on, can call on when you need or want support. I also know that you are busy, right? And a lot of our listeners are busy too, right? How are you maintaining these relationships where you can feel comfortable asking for help and not feel like you're being a burden to reach out?

35:50That's a great question. So first of all, I would just say this is definitely a strength of mine in the sense that I think relationships are one of the ways that I move through the world. But I actually started doing something at Facebook that I think I learned it from Sheryl Sandberg, who has a very powerful network. And I watched her be very thoughtful about how she stayed in touch with people. And so all that I did when I left Facebook was I made a list of all the people that I really loved working with and that I really loved learning from. I just wrote it down. And then every three to six months, I would just look at the list and think, who haven't I talked to in a while?

36:43And it was just as simple as like a text or a note or a, hey, let's have coffee. This is definitely like pre-children and things like that. But it was like, I just stayed in touch with people. And what it taught me over time, because I've done that now for many, many years, and it's not as systematic as maybe it used to be, is that the most powerful, I guess, network, if you want to use that word, but the most powerful relationships for me have come from meeting someone. And it can be anything. I have really great friends that I've met in an interview. They may not have been right for the job, but I just was like, ooh, you're really, I like you.

37:24I want to be friends with you, or I'm interested in you, or I'm learning something from you. And I made a bunch of great friends when I was trying to learn about SaaS, which is software as a service. I ran around Silicon Valley trying to learn from all the great SaaS leaders and made some great friends through that. And all I do is kind of follow that instinct of like, oh, you're like, great. And then I find a way to be useful to them. I have this belief that life is a barter economy, meaning if I'm useful to someone, expecting nothing in return, then eventually when I need something from them, they'll want to help me.

38:00It's like the idea that it's better if the world is full of people that owe you, you know? And so all I do is try to be helpful to people and kind of maintain that kind of relationship with people that I find interesting or compelling or that I learned from. And over time, you have this very powerful network of people that want to help you. And, you know, some of those relationships become much deeper over time than others and that you find a lot you have in common. And I think that's sort of probably ended up distinguishing the 10 or 15 people that I rely on and help me make decisions and are sort of my board of directors, if you want to call them that.

38:41That makes sense. I mean, I like that combination of this spirit of generosity and abundance and also this very tactical thing that anyone can do. I start 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.

39:23So 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.

40:08And 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 a bunch at 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.

40:39And 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.

41:05Perfect.

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44:15Okay, 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.

44:59And I just want to say, I actually believe there's no such thing as a generalist. Like I know it's nutballs coming from someone like me who leads a community and invests a lot of time in sort of no matter what 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.

45:35But 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 should, 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.

46:04Here'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 long-term leading a data team, girl can barely do math, so let's not 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.

46:44But 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 the way I help people do that when I'm talking to them about this is you want to sit down and think through 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. I felt fully utilized or just like, I don't know, like at my best.

47:23And 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, 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 the right tools at their disposal, but basically wading into chaos and figuring out the right path forward.

48:06And as he talked, it was just very, very obvious that there was a set of jobs where it was like, ooh, pick me. And then a set of jobs that were like, yeah, never hire me to do that. You may not be able to easily say, hire me to be your head of marketing or 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. I I definitely find that 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.

48:47And 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 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.

49:16And 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 at ted.com. We can't wait to hear from you.

49:49Worklife is a production of Ted and Pushkin Industries. This episode was produced by Isaac Carter. Ban Ban Chang is our story editor. Mixing by Hans Dale Shi. Ted's executive producer is Daniela Balarezzo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Hilash, Valentina Bohanini, Lainey Lott, Tansika Sungmanivong, 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.

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From the publisher

In fast-changing companies, some things move so fast that you rarely have time to consult the business books when questions arise. Welcome to Frequently Asked Questions, a segment on WorkLife where Molly answers questions from listeners about the topics they confront in real time. In this episode, Molly is joined by Ashley Murphy, a key member of Molly’s team and one of the people that helped create Glue Club, a leadership development community that Molly and her team run focused on helping leaders feel more confident and less lonely at work. These questions are based on common questions from the community that Molly and Ashley thought would be relevant for the WorkLife audience as well – tips for working productively with a boss you don’t always agree with, knowing when it’s time to seek out an executive coach, and struggling to pitch yourself to prospective employers if you don’t fit into a traditional box.


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