Why the smartest person in the room is asking the “dumb” questions with Molly Graham

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2:06Molly came onto the TED scene back in 2024 when she gave a talk telling people to ditch the stairs and jump off a cliff. Don't worry, it's a metaphor. Molly loves metaphors. And now she's back, this time as the new host of TED's Work Life podcast. She's taken the reins from longtime host Adam Grant, and honestly, I can't think of a better person for the job. After a long career of supporting leaders at some of the country's largest tech companies, Molly wants to use her vast experience to help more people feel less alone in their careers. During our conversation, Molly shared some special tips on how to embrace change, especially during a time where all of our jobs are rapidly changing, whether we like it or not.

2:56But first, a quick break.

3:03And now, my conversation with Molly Graham. Molly Graham, it is so nice to have you on the TED Business Podcast. Thank you so much for having me. I am delighted to be able to spend time with you today. And you're not new to TED. In 2024, you did give a TED Talk. I did. And you told folks in that talk that they shouldn't take the stairs. Can you tell our listeners what you told them? The stairs is my sort of metaphor. I live in metaphors for kind of what I think what we think careers are supposed to feel like, or maybe it's like what our parents told us careers are supposed to feel like, where you're supposed to show up in college and know what you want to do.

3:43That major is supposed to lead you to your first job. And then you get another job, and you get promoted and promoted and promoted forever. The best part about the stairs is safety and security. It feels like you know what you need to do to get ahead. The worst part of the stairs is that it's like a weird video game that you can get stuck inside of for years. The stairs will make you feel like your self-worth is tied to your title or your last performance rating or your next promotion. And I would say that, like, I followed that path for a little while. And then at some point, someone offered me a crazy opportunity.

4:28and actually drew on a whiteboard for me what he called a cliff jump. He was like, you can stay on the stairs. It's boring over there, but why don't you jump off a cliff? Most people do not stay stuck on the stairs out of necessity. They stay there out of fear. The trick is to learn to tell the difference between the kind of fear that says, I'm scared I might run out of money, which you should actually listen to, And the kind of fear that says, I'm scared I might fail, which you should take as a giant green flashing light to jump. Cliff jumps teach you what you are capable of in spite of fear.

5:15He was like, you know, cliff jumps are fun. They're also terrible. He was like, you're going to fall. You're going to fall for a while. They do take you down and backwards and you sort of feel like maybe it was a mistake. But then there comes a moment when you're like hit the bottom and start to climb out. And this sort of climbing out can take you places that the stairs don't even go to. That's the thing about jumping off cliffs. It doesn't just take you a couple flights up on the stairs. It's like a weird elevator that takes you to a whole new place. Cliff jumps teach you who you are and what you are capable of in ways that the stairs can never.

5:58After saying that, what did you hear from folks? It's been so fun because I think one of my favorite things to do in the world is to help people feel sane in the middle of change. And I think a lot of what I talked about in my TED Talk was like what it feels like when you take a risk. Yes. Which is, first of all, the fear that comes before the jump and how you navigate that. And then all of the emotions that come as you jump and as you're falling and you just feel like an idiot all the time. And you often are like, you know, did I make a mistake? Should I go back? And I think talking about those feelings, talking about the fact that even if you have those feelings, it doesn't mean it was a mistake.

6:43And that there will be a moment. And it often takes longer than you think it should. It takes six to nine months to feel that moment of competence. But there will be a moment of competence that will help you realize, oh, this is why and this is how much I've learned. So all of that is to say that I think describing that experience for people, like so many of the emails that I've gotten from folks have just said thank you for helping me understand what I was going through or helping me understand what I went through or helping me make a decision that I was scared of but realized what it's going to feel like and that it will probably be worth it on the other side.

7:16side. That is so important for everyone to realize. It is. I mean, I'm obviously like a huge advocate for taking risks and getting better at taking risks. And I feel like the world around us is changing so fast. And sometimes it feels like it's faster and faster. And I guess I kind of feel like this used to feel like a choice. Do you know what I mean? It used to feel like the stairs were an option and you could, you had this linear path, you could stay in one company or one function for 10, 15, 20 years. And I think one of the things that I am really seeing with AI particularly, and to some extent, also just the chaos of the last five years and all the layoffs and everything, change doesn't quite feel so optional anymore.

7:57And risk feels like it's everywhere. And it might be that you choose to jump off the cliff and it might be sometimes that you get pushed off. Right. But I feel like it's more important than ever to know what it's going to feel like and know how you can kind of make the best of it. That's so critical. And I study stress. So jumping off that cliff is stressful. Being on that other side is stressful. And so how do we actually embrace that in a way that will help us thrive? How do you think you embraced that stress? Wait, I also want to know your answer to that question. For me, I have learned over many, many cliff jumps, big and small, to love it.

8:39I now know that there's a certain type of fear that when I feel it, I have to do the thing I'm afraid of. There is still stress. There is still all these emotions. That never goes away. No matter how many times you do it, you can give TED Talks about it and you're still going to feel it. I just realized that a lot of these emotions that come with change and stress, like they were never going to go away. So I had to make friends with them. I grew up on the Muppets. So I manifested them into this little monster and I gave him a name. So my monster's name is Bob. And I always tell people that I work with, you can name your monster whatever you want.

9:12The main thing is to realize you have one and that it's your little traveling companion. And they're just going to be like good monster days and bad monster days. You reminded me of a phrase I once heard, an acronym for fear, false evidence appearing real. Oh, I've heard that one before. That's so And so it sounds like what you're able to say, OK, I'm feeling this. Is it false? It probably is. And, you know, I need to just not let it dominate. Yeah. Not listen. Well, that's actually the purpose of this monster. When I'm having like a bad day, I can now say that's Bob, not me. Bob's back. Bob's back.

9:49Yeah, exactly. Bob's back. Bob's having a bad day. Do you know what I mean? Oh, I see. Got it. Yeah, it's like a bad Bob day. And, you know, I even call them sometimes like monster attack. I think there's something about externalizing it that allows you to like depersonalize it where you're just like, that's the monster, not me. Yeah. And it depowers it too. And part of what my point is and that I've learned is like it's all normal. You can't not have these emotions. The choice is what you do with them. Yes. And they should not drive your actions. And that's when we're all our worst selves, right, when we let the little monster send the emails or make the decisions for us.

10:24Right. One of the things I talk about in stress is that we need to acknowledge it. We need to welcome it. And then we need to use it. Yeah. And so a lot of what you're talking about is about acknowledging it. It's going to be there. Bob exists because it's sometimes assigned to me about something that I need to pay attention to or that I care about. And then, OK, if Bob is back, how can I use what I already know about Bob and my experience to take me to the next level? Yeah. So how do you use it? So you can use it by saying, okay, this stress that I have right now, what can I change? What can I do differently?

10:58It is a signal telling me something. So maybe I need to shift my mindset about what's going on. Or maybe I need to change something in my environment right now. Or maybe I need to phone a friend. So that's how you use what you're experiencing, the emotions, the feelings, the bodily responses, because that's another aspect. Okay. Can I tell you one of my other rules? Oh, yes, you can. Tell me what you think of it. So I first developed this understanding of these waves of emotions when I was working at Facebook. And I felt like I was literally sort of being forced into a different job every three weeks because the company was changing so fast.

11:33And this project that I was working on was like changing so fast and growing so fast. And so I had all these just waves of emotions rolling through, you know, sometimes it's excitement and joy and all that. But sometimes it's just insecurity, exhaustion, territorialness, all that. People always tell you to sleep on it. You know what I mean? And I said that in my TED Talk. I was like, a lot of them don't go away in 24 hours. You go to bed, you wake up the next morning, you're like, Bob's like, I still want to send that angry email. But I did find if I gave it two weeks, 90 % of those emotional reactions passed through.

12:08And it let me find the signal in the noise. It let me find the thing that was real. Give me some research on it. That is one of the ideas behind meditation. what you're doing in those two weeks is you're being present with everything that is coming up yeah and if you're present with everything that is coming up then it's not crowding you out and you're not denying it you're not pushing away you're just there with it and i think the research shows that when you're actually there with it then there are parts of your emotion center of your brain the amygdala that light up differently i think that's right and i also love your point about signals.

12:43To your point, the emotions are trying to tell you something and you can listen to them and you can observe them and you can take the information. But the point is to just not let them control you. Yeah, exactly. Yeah. And not be reactive. Right. Your two weeks allows you to be proactive, not reactive, you know, and your talk resonates with me a lot because I'm on sabbatical right now and having a really unique experience. I've had to embrace my inner professional idiot, which you talk about. I've had to do it. I can tell you that this is one of my greatest strengths. I am comfortable sounding like a moron.

13:19I am great at sitting in rooms with brilliant people asking very dumb questions. But what that actually means is that I have become an extraordinary learner. The first meaningful jump I ever took was leaving HR at Facebook. And somebody asked me if I wanted to build a mobile phone. And I actually didn't mention that detail in the talk, but it was such a dramatic change. I was like, why are you talking to me? Like, I don't know anything about mobile. I know nothing about hardware. This friend said to me, you've proven that you're good at like running these big company-wide projects in HR. Why don't you go see like if it's transferable, why don't you go see how actually good you are?

13:59And it was such a good challenge to 25 or 26 year old me. I was like, yeah, I'm going to go see. And so I took this job and started on this project. And I spent six to nine months feeling just like a complete moron. And I was sitting in rooms with all these amazing engineers. And I was like, excuse me, what is a CPU? Or like, what is that? What does that word mean? Or what does that acronym mean? And at first, it was just me in my head being like, am I the I think I'm the only idiot in this room that has no idea what is going on. And then I taught myself to just kind of pull people's sleeves after the meeting and say, hi, sorry if this is a dumb question, but like, what did that mean?

14:40Or I didn't understand that. And part of what I learned when I would tug people's sleeves is that they loved teaching me, that they were happy to answer the question. They didn't think it was dumb. I mean, for them in a lot of cases, it let them feel like an expert. And the other side of that is that most dumb questions are not actually dumb. It's so true. And the beginner's eyes and the beginner's mindset often are actually just like the most valuable resource because even if you walk into an organization, having those beginner's eyes, like you see things that everybody else just takes for granted.

15:11So many people are afraid of sounding dumb that the world is littered with important questions that never got asked. Questions like, can you define that word for me? Why are we doing this? Why are we having this meeting?

15:34Embracing being a professional idiot often actually makes you the most valuable person in the room.

15:43At my last company that I ran, we had a 30-day presentation for all new hires. It started with all new executive hires. And then we started doing it for every single new person. We just said, tell us what you're seeing. Tell us what seems strange. Tell us what you expected. Tell us what you're planning to do. You know, give us like a little bit of your roadmap. But a lot of it was just about hearing what they were seeing so that we can learn from them. We have to remember we are our harshest critics. Yeah. And so you're sitting there like, I think this is a dumb question. And then everyone's like, no, this is a good question.

16:16Oh, my God. So often I tell like more junior people starting off in their jobs or whatever, if you had a question and someone senior or someone else asked it, that is a reminder that your questions matter and you need to ask them and raise your hand. A hundred percent. And actually, I think at Facebook, Sheryl Sandberg was actually very good at that. She used to get really mad at any of us, but definitely at me when we made ourselves small. Yeah. She was always like, ask the fucking question. Yes. You know? Ask it. Hello. Just ask it. And what are you afraid of? This is going back to the fear.

16:51What are you afraid of? I don't think I've ever left a meeting and said, can you believe that person asked such a dumb question? Yeah, totally.

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18:17What are some of the lessons you've learned about what it takes to scale a company and be effective? I started my career in tech at Google. Google was really quite big at the time, I think maybe 10 ,000 employees or something. But my department that I joined, which was communications was 25 people when I joined it. And nine months later, it was 125 people. So 5x growth in a really short period of time. And one of my many lessons from scale is that the rate matters more than the number. Going from one to five can feel as crazy as going the rate that I went through. It is just that percentage growth that really dictates the experience of it for people.

19:00But one of the things that I really saw was when you're going through that level of scale, and then I saw it again and again and again at Facebook in the time that I was there, was fear. Like what we were talking about, there's so much changing and so much happening that people get scared. And the instinct when you're scared is to hold on to what you know. The instinct when you're scared is to control, right? And so in a lot of these cases, particularly when you've been early at a company, you have built an identity. You're like, I am the person that does X. And the truth is that if you don't evolve, right, if you stay trying to hold on to that thing that you're known for, that thing that you're good at, the whole company is growing and changing around you, right?

19:40So if you hold on and you stay attached to one identity that was relevant in this one year or this one instance, you're sinking because everything around you is growing. So what was true for me at Facebook was the graph of how fast our business was growing felt to me like the graph, not only of how fast the company was changing, but also of how fast my job was growing and changing and therefore how fast I needed to grow and change. I came up with this talk that I used to give folks that work for me called Give Away Your Legos. And it was just like, I know you've built this beautiful house and you're really proud of it and it's very shiny and new and maybe it's not quite done, but I need you to like hand them off and I need you to give them to that new hire we just hired and I need you to go work on this new thing.

20:25And yes, it's scary. And yes, it's hard and all the emotions that we've been talking about. But part of the rule with scale is that you have to grow as fast as the company is growing. Yeah. My godson will not like that. Every birthday, I give him Legos. It's part of why I like the metaphor and why I think it probably resonated with people is like, it's hard to share. It's hard to like half build something and then have somebody tell you, hey, give it to that person and you're like, they're going to screw up my castle. Do you know what I mean? Or like, what if they do it wrong? Or actually, what if that's the only fun part of the castle?

21:00Yes. That's what I love. I love being in the details. And now you're telling me I'm supposed to give the details to somebody else and not micromanage them? Yeah, exactly. That is so real. Often when I give speeches on this concept of give away your Legos now, and I'll often get asked, what's the best way to hand off your Legos to someone? And I feel like people want me to say, like, so first you hand them every single Lego and you explain to them exactly why you placed it, where you placed it. And then you hand them like an instruction manual. And I'm like, no, that's what you want to do. The answer is chuck the Legos at their face and run in the other direction and be like, let me know if you need help.

21:38Bye. So I've done some work on gender differences in delegation. Yeah. Oh, interesting. And found that women are less likely to delegate than men. They associate delegation with more negative emotion, more overburdening of your subordinate. And in one of the experiments, we gave men and women the opportunity to delegate to somebody and then coded their behavior. People watched the videos and women did just what you said. They just like gave the thing to them and went away because they were like, this is so stressful or whatever. I just want to give it to you and run away. But they still ultimately didn't delegate as much as men.

22:13But the reason I'm sharing this is I don't always like to just identify a gender difference, I like to talk about how to fix it. And in this work, we found that when we remind women that delegation really does help your subordinate, that's when they were less anxious about it. Man, that is so interesting. Yeah. Because the gender role stereotype that women are supposed to be communal and not agentic and dominant. And delegation is a little bit of both. You're giving someone something to do so you're being agentic, but you're also growing them. than the theories that women would be less likely to engage in it because of that gender role conflict.

22:49I have to tell you, it's so interesting. In my experience, I have not seen any gender difference. Like I genuinely see across the board people are very bad at it. And actually, there's starting to be this very annoying backlash in the technology industry around micromanagement being a good thing. Oh, no. Yeah. Yeah. I wrote this article a bunch of years ago called manage the what, not the how. And it's essentially the point, which is like, it's so tempting to hand somebody something and really be prescriptive about how to do it, right? To be like, here's how you run this event. And here's how I've done it for 10 years or five years or whatever.

23:31When actually all that matters is the what, meaning did they hit the goal? And I got a bunch of feedback about it from folks saying like, I really think you're wrong. The how really matters. And when I dug into it, we actually agreed. Meaning often the what has nuance. Often it's not just you have to hit the goal. It's that you also can't screw over this other number or there's like nuance in how you hit the goal that should be part of the delegation, that should be part of the conversation around what good looks like. Yeah. Do you know what I mean? I do. And that's why I want to do more research on it because I think the delegation is one of the most important skills that we need as a leader, but we don't have much knowledge about how to do it well.

24:14What is the baseline? What is the base rate? Maybe even just saying that women don't delegate as much as, maybe it's that women are actually delegating the right amount and men are delegating too much or whatever. Yeah, I see a lot of founders, therefore a lot of men, because most founders are men these days, depressingly still, sort of create this environment where they say, yeah, go crush this project. And then they come in at the last minute and rearrange all the furniture, which also is not delegation. No. Now, these insights from leadership, I'm assuming some of them have also come from the Glue Club.

24:45Tell us more about what made you decide to create this community for leaders and what the Glue Club is all about. Yeah, totally. I had spent, you know, 15 or 16 years building companies. And I had built this career around being a COO and basically helping brilliant leaders build organizations based on their vision. You have the vision, I'll turn it into reality. And at some point I just realized that that wasn't my work anymore, that I had done it. I had learned so much and I had run out of energy for it. And it really left me with this, wait, okay, what do I want to do then moment? And I had to go on a little bit of a journey around what is it that I love doing and what is it that feeds me and what is the work that I feel like I'm meant to do now.

25:32And I realized that what I love doing is supporting the humans inside the companies. And even more so actually in technology, but honestly in general, I think that there is a lot of support out there for CEOs. I think there's a lot of communities. I think there's a lot of writing. I think there's a lot of stuff. And there is a lot less for the people that work for CEOs and for the people that are learning to be leaders. And so I became more and more intrigued just by how to build support for those folks. And I think a lot of that came because when I was in my first COO role, there wasn't very many people to lean on.

26:12And so I would go out to breakfast with my friend who was the COO of another company at the time. And we would just stare at each other and be like, this is crazy. Like, what are we doing? How do we do this job? And slowly we convened this group of people that met once a month for five years that was all these COOs of all these different companies all over Silicon Valley. And it was this incredible community for me that kept me sane, saw me through three different jobs and just was always a sounding board. A lot of folks had seen a bunch of scale or seen startups before. And so I could always ask questions.

26:44And then I also felt like I could share with them wisdom as well as mess. And so when I started to think about what I wanted to do for leaders, I think I wanted to create that space for people. And it really started as an accident where we just tried to do one sort of circle. And we got such an overwhelming response that we ended up making four sort of circles of folks that could learn together and grow together and also support each other. And then when it was over, we sort of said to them, do you want this to keep going? And they were like, yes. And so it turned into a community. And over the last three and a half years, it's become this incredible community of leaders that are learning and growing And that sort of can't find that inside their own companies, probably because they're pretty senior at this point, that have enough experience that they have some scars and battle wounds, but also want to keep learning and growing and want to find a safe space to say, this is crazy.

27:37And how do I do this? And I'm scared or I don't know what I'm doing. And to be able to have that kind of community around you is, for me, one of the most powerful forces to help you be the best leader you can be. Nobody has the answers. You know what I mean? It's not like anybody's out there like being like, I've done this before. It's like, no, we're all facing down this incredible sense of what is this going to look like in five years? And you really need people that you can say, what are you seeing? And what are you seeing? And what are you trying? And what are you failing at? What are some of the key themes that you hear people express?

28:06So much of what we talk about is about the humans. I always say we try to make all the playbooks and all the frameworks in the world. But at the end of the day, companies are just organizations of humans. It's an entity that was designed to pull a group of humans together and hopefully create something that's greater than the sum of its parts. And what are humans made up of? Humans are made up of talents and time. So the job of leadership at the end of the day is how do you create the conditions for success? And part of my point to the folks that we work with, and this is something you have to learn when you're earlier in your management career, is you can't make people successful.

28:44Nope. You can create the conditions that give them the highest likelihood of being successful. You know, and I always think the holy grail is you want the highest performer in the world to think, I want to work for that person, right? Because they've created this beautiful environment where I can do my best work. But the point is not to make that person successful. The point is to build the environment where they can do their best work. And so that is what we talk about. And we talk about all the messy human stuff that's part of that, right? How do you manage people? How do you create those conditions?

29:16What is your job? What isn't your job? I actually feel like one of the things more and more I'm seeing with even the AI conversation is just these days anyway, it's about how the humans use the tools. It's true. And watching the behaviors of humans and how they integrate with AI is fascinating. Yes. But yeah. At the end of the day, it's all about the humans. Yes. And you did not say the humans and their crazy and their baggage and their trauma from their mama and their dad. I do tell my students, like, this leadership thing you're signing up for is not easy. No, and you just said something that I actually say inside of Glue Club a lot.

29:51I don't know that I say it publicly that much, but I feel like one of the things people come to Glue Club for is to be like, is this crazy normal? Or is this crazy extra special bad? So much of what we hear in, like, the first couple months that people sign up is, like, either it's like, oh, okay, it's normal crazy. Or it's like, oh, that's not good. No, that's not right. That is not right. With no fees or minimums on checking accounts, it's no wonder the Capital One bank guy is so passionate about banking with Capital One. If he were here, he wouldn't just tell you about no fees or minimums. He'd also talk about how most Capital One cafes are open seven days a week to assist with your banking needs.

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31:47And with fast, reliable internet and 100 % U.S.-based customer support, you'll stay connected and ready to bring your vision to life. Learn more at spectrum.com slash business. Restrictions apply. Service is not available in all areas. In addition to Glue Club, I think it's also really good that senior leaders have executive coaches to really have other sounding boards about like what kind of crazy is this? Is it extraterrestrial crazy or is it crazy crazy? Well, and one of the things that I talk about with folks that are curious about the community is that I think executive coaching is one of the most beautiful things in the world.

32:26I was gifted one in one of my last leadership roles and it made all the difference in the world to me and my sanity and me figuring out who I was and where I needed to go. And not everyone can afford it. Right. And so part of what I think we do in Glue Club is sometimes provide an on-ramp to that because nobody can do this alone. Do you know what I mean? Well, you can try, but it is like lonely and hard and it will make you think you're nuts. You know, the more senior you get, the less likely you are to find that support inside the four walls of your company. the more likely people are looking at you thinking, what should we do?

32:59And you're like, I don't know. So you need support. I think one of the things I love most in the world is helping people that I'm not necessarily going to be able to meet, but helping them not just in a sort of superficial way, like help making them feel like, oh, you move me forward, or you unstuck me, or you made this make sense. And that's the kind of emails that I get from my writing. And that brings me a lot of joy. And it sounds like that is going to continue because of the new exciting news. You're taking over for Adam Grant and you will be the new podcast host of Work Life. Yeah. What are you excited about?

33:38You're going to be my Ted Cousins. Yeah, I know. I'm so excited. Ted Cousins, Ted Audio Cousins. Yes. Ted gave me a call about nine months ago and asked, they said that Adam was going to stop doing work life and that they wanted to figure out the new version of the show. And they asked if I wanted to be the host of it. And I had this immediate fear reaction. I was like, I don't know if I could do that. I don't know if I'm going to be good at it. I'm terrified. And because of all my experiences, I was like, okay, we have to say yes to this, you know. But the other thing that I really felt and feel more now, even that I've started making episodes, is just this deep excitement that to have a platform to connect with more people and to help them feel less lonely and more confident in their work journey.

34:26And so much of what has made my leadership journey sane is having mentors and these smart, wonderful people in my life that I've been able to learn from. And so a lot of what I'm excited about is bringing on some of the people that I've learned the most from, but also just all these other amazing humans, some of whom I'm even meeting for the first time and drawing out their lessons that we can all use, you know. And so trying to give people access to that wisdom that helps us feel a little bit less alone and hopefully helps give us new tools that can make us better sort of humans at work. Well, I felt the exact same way around six years ago when I started as the host of TED Business.

35:13And if there's any advice I'd offer, it's have fun and then just continue to remember that you have incredible things to share. And I know that for sure, having just spent this short time with you, I have enjoyed every minute of our time together. And I really wish you all the best with your podcast as my TED cousin. And thank you for your time. This was so fun. And it's such an honor to get to learn from you. Feelings mutual. Thank you. Thanks. That was Molly Graham and I in conversation at the TED conference this past April. You can catch episodes of Molly's new season of Work Life wherever you get your podcasts.

35:53That's it for today. TED Business is part of the TED Audio Collective. This episode was produced by Hannah Kingsley Ma, edited by Alejandra Salazar, and fact-checked by Julia Dickerson. Special thanks to Maria Ladias, Farrah DeGrange, Daniela Ballarezzo, Tansika Sangmanibang, and Roxanne Heilash. I'm Madhupa Akinola. Thanks for listening.

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