I am excited to share my conversation with AJ Thomas, who I had the pleasure of meeting at the Culture Summit where we were both giving talks. AJ was sharing her perspectives on being a Chaos Pilot at Google’s Moonshot Factory, Called “X”. At the time of this conversation, she’s been with Google for nearly four years, starting as Head of People.
AJ is also A CxO in Residence at A.Team AND an Advisor at Magic Eden and SemperVirens Capital. She is also an Executive coach on the side.
She’s got a full calendar.
X, A.Team, CxO. This is starting to sound like the credit roll on Sesame Street! That is a lot of letters, but we’ll add a few more, like T, I and Z.
You may have heard of being T-shaped, as in having breadth of knowledge in general and having depth in one particular area…versus being “I” shaped - having just depth, but no breadth. Breadth is important in any position, because having some breadth means you can more readily engage a broad swath of people in productive dialog, partially because you “get” their inside language enough to collaborate with them. This breadth of collaborative potential is especially important for Leaders.
AJ is a fan of being a Z-shaped-leader, which for her means having depth across many different areas, over time, and the ability to connect the dots between them. But while being able to connect the dots, to scan the horizon for innovation and emergent opportunities, to be able to see an Audacious and almost-impossible future AND communicate that vision to others is a powerful leadership skill, AJ sees Humility as an equally powerful leadership value. This puts AJ in excellent company with Dr. Marilyn Gist, PhD, Professor Emerita of Executive Programs at the Center of Leadership Formation at Seattle University, author of "The Extraordinary Power of Leader Humility," and a past guest on this podcast! Check out our conversation here where Dr. Gist shares her Six Keys to Leadership Humility.
I love AJ’s idea of keeping Audacity and Humility in dynamic tension - staying “Humbacious”! That balance, the ability to “sprinkle” one quality or another into a conversation, shows up as tremendously powerful and generative in AJ’s leadership and coaching work. Audacity holds space for people to explore potential - the biggest vision and possibility. And Humility drives us to assume that we might be wrong and to leverage the mind of a scientist to de-risk the road ahead with powerful questions and intentional experiments.
Enjoy this powerful deep dive into these ideas and a lot more.
AI Automated Summary
AJ and Daniel discuss the concept of being a "Z-shaped" person, with depth across many different areas and the ability to connect the dots between them. They also discuss the principles of coaching, including being present, listening for what has heart meaning, and telling the truth without blame or judgment. They emphasize the importance of balancing audacity and humility in leadership.
Meeting summary:
(3:41) - AJ shares her favorite question to ask in conversations: "Can you tell me what led you to that?" to learn about people's approach rather than just their destination (7:04) - AJ describes the T-shaped person and how they have broad experience in their field and deep expertise in a specific area
(7:36) - AJ describes herself as a Z-shaped person, with depth across many different areas and the ability to connect the dots between them
(15:21) - AJ explains how exploring parallel universes can be valuable for leaders, allowing them to access different perspectives and create more compassionate ways of being and doing
(25:00) - AJ shares the four principles of coaching that have influenced her, including choosing to be present and derisking problems through questioning.
(29:16) - AJ notes that it can be difficult for leaders to hear the truth without blame or judgment, but earning trust through presence and deep listening can help facilitate this (37:30) - AJ introduces the concept of "humbatious" - being audacious yet humble in approaching the future
(41:10) - AJ and Daniel discuss the importance of balancing audacity and humility in leadership
Links, Quotes, Notes, and Resources
https://www.couragetakesflight.com/
Minute 1
Daniel Stillman:
Why do you think you enjoy the unpacking side of a conversation?
AJ Thomas:
I love going a little bit deeper in the conversations just because I'm ever the explorer. I'm just curious about where asking the right question can take you. And unpacking, and maybe it's just because I do this, but it's literally unpacking. When you're packing suitcases and you're unpacking different suitcases, there's always little surprises that you never knew were actually in there. Like the little side pockets where maybe you put a $5 bill or some nice little thing that maybe was just packed away on your journey. I see that as something about conversations as well. You never judge the contents of a suitcase by the suitcase itself, like you never judge a book by its cover. But if you ask the right questions and you're curious enough and you're unpacking enough, you just might find something pretty amazing.
Minute 13
AJ Thomas:
It's just a certain sense of, I think it's just built in for me, but I started describing myself as a Z-shaped person because I'm also very visual. So I was like, okay, the T shape, I get. We learn about it through design thinking. We learn about it in business school, but the Z-shaped has always kind of looked scattered to everyone. And I guess what I wanted to do was describe a way where that is just like a linear path is not wrong, a T-shaped path is not wrong, a Z-shaped path is also not wrong as well.
And so there's probably many different kinds of these things, but for me, what tended to describe my journey most was the ability to go from one vertical to another domain, take learnings from that, then go back and take learnings from that thing and go to something completely different. And then continuing to do that formula. And then really it wasn't until hindsight and I looked back and I stretched that thing that I found that everything in common, whether I was in sales and operations and marketing and product, building for a sports center, in HR, working in talent, whatever it may be, the through line was always about people, culture and organizations and how to build the future of what that looks like. So I think there was no foresight into it. Everything was just as a reflection. And quite frankly, I got tired of defending myself, as I saw it as defending myself. And everyone's like, you do all these things, how do you do all these things?
And I always get the question, how do you do it all? And I always have the same answer and it's only two words and it's always I don't. I don't. But again, it's not until I had the hindsight, I think I'm a little bit later on in my career now where I can say, wow, when I was doing this, was I like, yeah, I'm totally doing the Z-shaped thing? No. I was like, I don't know what's happening, but I'm just going to keep asking questions that's going to lead me to these different things.
Minute 26
AJ Thomas:
the four principles that have really influenced me is one, showing up and choosing to be present is so important. And I said that so fast, you probably almost didn't catch the nuance. A lot of people are told to show up and be present, are you present? Be present. And I think what Professor Angeles Arrien encourages us to do is be present, choose to be present. Being present is a choice. Being active in that is a choice. You're not distracted by anything else but that person you're having a conversation with, and it really helps hold the container for whatever you're going to be talking about or coaching through. The second principle that I loved was the ability to listen for what has heart and meaning for somebody, and it could be what they're not saying. Like when you ask somebody, how are you? And they say, I'm fine. If you really chosen to be present with that person-
Daniel Stillman:
How are you really?
AJ Thomas:
Exactly. You're like, well, let's talk a little bit about that because you say you're fine, but I'm hearing outside of what you're saying through your physical presence that you might not be. So it's really interesting, it helps you pay attention when you choose to be present. You listen for what has heart and meaning for somebody. Or when they say something over and over, but it's kind of glib but then when you really get to the heart of it, they're like, oh yeah, that actually means a lot for me. That's a really interesting one. The third one which I love is the ability to tell the truth without blame or judgment. You have to do that as a coach. And I think especially with working with leaders, it can be really isolating to be at the top. And again, I work with a lot of founders and CEOs where they're probably the only person that feels like they're carrying the burden of all the things.
And sometimes because they're in such positional power, people will not tell them what is wrong or what they feel could be worked on, or what they feel is a blind spot because one, they either have not been invited, or two, because society or the way in which they've interacted with communities has told them that there's a respect for hierarchy. But the respect for hierarchy is also the ability to be able to tell that person in that hierarchical relationship the truth without that blame or judgment. You can't do that without earning trust of course, that's really hard to do. So it's almost a little bit of a paradox. So it's a very interesting navigation of how you're able to really tell the truth without blame or judgment, but you have to be able to choose to be present, listen to what has heart and meaning for people 'cause that burdens the trust to be able to do that.
And then lastly, as a coach you're never advising. You always have to ask and be curious and hold the space, connect back, connect the dots, but that also means you have to be open to outcome and not attached. Which is why giving advice is not coaching.
Minute 36
AJ Thomas:
And I talk a lot about how Moonshot mindsets are accessible for everyone. I think one that I love in particular, an Astro talks about this all the time, is the ability to both be humble and audacious. Which I've then jammed into a word called humbacious. But anyway, it's the ability to be audacious enough to articulate an idea or a path forward, but to also be humble enough to say, I don't understand the entire problem set just yet and so it might not be right so I need to de-risk it, and here's how I'm going to do that.
More About AJ
A lot of what fuels my interests and passions intersect at bridging the gaps in talent, culture and career. The three words above matter to me in the grand scheme of things. The result of what I do moves people and organizations forward to create a future of infinite possibilities. I'm very passionate about building the leaders and organizations of tomorrow. It's never easy, but it is my own definition of meaningful work. I currently serve as the Founder and & Executive Director of Infuse Program Foundation where we turn at-risk youth into entrepreneurs in nine weeks. I also have the wonderful opportunity to serve as the People & Culture leader for one of the nation's largest real-estate online marketplaces. I consider what I do with Infuse and work as a key contributor to developing talent for the future.
Building culture is my knack and creating the conditions for people and their talents to come to life in a meaningful way is what excites me. I am often described as a big picture thinker and fanatic executor, though I consider myself an entrepreneur at heart that's just naturally curious. I like thoughtful approaches to complex problems and creating high impact solutions. I fall deeply in love with problems and am energized by the journey in discovering why they exist and how to solve them. The work I do centers around moving people and organizations forward by way of creating, building and institutionalizing process, and designing/experimenting innovative approaches. I get most of my joy in discovering leadership from those around me and have continuously found that a vast knowledge of intelligence exists untapped just waiting for the right question to be asked.
Full Transcript
Daniel Stillman:
All right. Well AJ, thank you for making the time again and thank you and welcome to the Conversation Factory. I'm so glad you're here. We're doing this and you sound amazing today.
AJ Thomas:
Oh, thank you. I'm really thrilled that we got this mic set up working pretty well for us, so I'm glad to be here with you, Daniel.
Daniel Stillman:
Awesome. So my first question for you is, what are your favorite kinds of conversations?
AJ Thomas:
My favorite kinds of conversations are I think ones you can build on. I never like conversations that are just linear, might as well just be a to-do list or an action item. But I like conversations where you can unpack, get curious, and learn things from. Those are usually the best kinds of conversations without even knowing you were going to learn, going into it.
Daniel Stillman:
Yes. Man, unpacking is like... That is a leadership skill.
AJ Thomas:
That's hard to do.
Daniel Stillman:
Why do you think you enjoy the unpacking side of a conversation?
AJ Thomas:
I love going a little bit deeper in the conversations just because I'm ever the explorer. I'm just curious about where asking the right question can take you. And unpacking, and maybe it's just because I do this, but it's literally unpacking. When you're packing suitcases and you're unpacking different suitcases, there's always little surprises that you never knew were actually in there. Like the little side pockets where maybe you put a $5 bill or some nice little thing that maybe was just packed away on your journey. I see that as something about conversations as well. You never judge the contents of a suitcase by the suitcase itself, like you never judge a book by its cover. But if you ask the right questions and you're curious enough and you're unpacking enough, you just might find something pretty amazing.
Daniel Stillman:
I agree completely. I feel like we could have a whole side conversation about luggage, clearly. I believe that bags are maybe the main thing that differentiates us from the rest of the animal kingdom. And I'm obviously I'm obsessed with bags and I agree with you. I actually love leaving things in my bag from if you travel a lot, it's nice to... When I switched bags recently, I was like, I need earplugs because this hotel's walls are thin. And I was like, damn it, I don't have any earplugs in this bag. I'm so sad. What are your favorite unpacking questions? You talked about how, and I agree with you 100%, the right question can help you with exploration. When you are trying to unpack with people, do you have a favorite question or is it more of a stance or an attitude, do you think, that you bring to it?
AJ Thomas:
I think it's the whole piece of loving conversations that you can build upon. And so it really takes... Crafting the right question often doesn't come with, here's a zinger. She's always going to ask a zinger, right? Yeah, I'm going to talk to AJ. She's always going to ask me this question. It always comes with kind of the exchange of perspectives that you have with somebody and then you build the right question from there. I love that question. The thing I tend to ask quite a bit when I'm in different conversations with folks is just, oh, that's really interesting. Can you tell me what led you to that? Whatever it was, I think it helps people reflect back. It helps people themselves unpack. Or if someone tells me, oh yeah, I ended up doing this thing and then I created this project, which ended up this thing.
Oh, that's really interesting that it ended up in that specific space. Did you ever know it was going to go there? Tell me what led you to that? What were the one or two things that you decided to either follow on a hunch or intuition or whatever that may have led you to wherever that thing is? So I think those are really interesting conversations because you learn a lot about people's approach versus just their destination. And sometimes that's much more fun than like, oh, I won this thing, or I experienced this thing. Oh, awesome. How was that?
Daniel Stillman:
Asking about the journey. Okay. Well, so now I feel like I have to ask you, 'cause we don't always unpack the how you got here question. But you mentioned being an explorer and I'm curious what questions you've been asking yourself on your journey that have brought you to go through some of the journeys that you've been going through. What if I said... This is a really fluffy question, but you see what you can do with it. I don't know.
AJ Thomas:
Yeah, no, for sure. Let's build on it.
Daniel Stillman:
Yeah, let's build. Thank you. Yeah, you're a builder and explorer, so I feel like I can ask a crappy question and you'll just do something good with it, so please proceed.
AJ Thomas:
No, no. There's never any crappy questions, by the way. So just keeping that in mind and riding on that wave and building that, I think what has led me to be an explorer, I could tell you all the motherhood and apple pie things like, oh, I'm just naturally curious and I just really love to see where these destinations take me. But it really is just an interest in the dots that connect things. So for me, for example, because of the profession that I'm in and the line of work that I've been doing, people tend to ask me about my career. What places have you ended up? I'm the epitome of the non-linear person, and it's not by design. It is led by asking the questions. And I think we talked about this previously in other conversations where you have your linear shaped folks, you have your T-shaped folks within an expertise, for example, HR.
I can go really broad on that, and then I'm probably really deep in compensation or in engineering. I'm a really great hardware engineer as a depth piece, but broadly I know everything about full stack. But I think that's the T-shape. For me, I'm really more of a Z-shaped person where I like to explore things here and there. And then I like the alchemy of mashing them up to see if there's any parallels. So for example, I've had the opportunity of having in my background sales and marketing roles, I've been in ground up builds of operational teams, support center teams. I had the opportunity of really diving deep into HR early in my career and then diving out of it and going into something completely different like product, and then becoming a customer of the expertise I spent a lot of my early career trying to hone, and then going back into it as a practitioner with those skills from that parallel universe.
And I've been doing a lot of that in my work to date, to date. Knock on wood. But to date, I've never been in a job that I've ever done before. And it's nice because you proceed until apprehended, but you just can ask all of the questions because you can reimagine certain things in different ways because you haven't traveled it before. Some folks I know that makes them really queasy 'cause it's like, well, how do you build expertise? I think being Z-shaped stacks your expertise because for me, if you think about this zigzag shape of a career, if I then pull it, the through line has always been people, culture and organizations. And I think that's beautiful. I can layer in coaching in that, which I've done. I can layer in the understanding of financial markets, which I'm currently doing right now with the work that I'm studying around venture capital and private equity.
I can layer in operationally, how do you build a tech stack into that? And sometimes people are like, you know a little bit about everything as you're a jack of all trades and master of none. Actually, no, I'm not. I'm just actually innately curious of where I can connect the dots. And I think that's where, for me being an explorer is fun. I want to come prepared to an unknown situation with... I use a lot of analogies, so tell me if this is a lot, but think about it as my most creative self is maybe a chef, we'll put that as a thing. They create amazing dishes and experiences, et cetera for people, but they travel the world tasting different ingredients. And at the off chance that they're somewhere where they need to then cook a dish, they have all of this access of these spices that they have collected.
For me, those spices are perspectives, those are skills, those are experiences that I never would've been able to do if I were just trudging along this linear path. There's nothing wrong with the linear path, by the way. I want to make sure that that's clear because I think there's a lot of vocations and professions that have that. But I think for me, what works because of the work that I do is this explorer mentality and then giving back to that exploration through connecting the dots in whatever journey you're going after. And you leave a little bit of what you've found before included in the new thing that's being created and I think that's fantastic. I mean, that's the way I think about coaching as well, is where can we collect these different perspectives and then how do we connect the dots to an insight?
Daniel Stillman:
So when did you start thinking about yourself as a Z-shaped person? And so just to review, 'cause this is interesting, I want to make sure I understand it. The T-shaped I'm familiar with the model and you described it. You have broad experience in your field and then have or actually brought experience outside of your field. You can maybe collaborate across multiple fields 'cause you know something about many things, which I think is, I can't remember if that's the hedgehog. The hedgehog knows a lot about one thing. The fox knows many things, but the hedgehog knows a lot about one thing. And you want that. You do want that depth in a person that you're hiring where you know what you're hiring and that they have deep expertise in this.
But a Z-shaped person, it sounds like there's multiple depths. There's depth across many things. You know many things about many things and there's a slash across everything where it's transdisciplinary. Tell me more about this mental model and I actually don't know if it's your model or if it's something that you started to absorb from... Is it out there in the ether that I just missed this or we just need to buy your book when it comes out about Z-shaped people?
AJ Thomas:
Hopefully it's the latter. I don't know. I'm a self-described Z-shaped person. I don't think there's ever been a model out there, but I think it just came out. And if there is, awesome. I haven't even Googled it or anything. Maybe we should and just see.
Daniel Stillman:
Pause for a moment, everyone.
AJ Thomas:
The rise of the Z-shaped person. No, I think for-
Daniel Stillman:
It's a good title. That sounds...
AJ Thomas:
For me what I think is really interesting is the depth doesn't have to be vertical. The depth can also be horizontal. And when I started describing myself as this Z-shaped person is when I started getting into conversations where people were asking me, how did you end up doing these many different things? You're a singer, you're a sales, you're in marketing, you're coaching.
Daniel Stillman:
By the way, I'm going to interrupt you. So if you don't know, you missed the first five minutes everyone when AJ went through three different microphones that she was choosing amongst to hack into her computer. And one of them, it was Chrome, beautiful microphone. I know.
AJ Thomas:
Wait, hold on.
Daniel Stillman:
Yeah, I know. It's amazing. It's a gorgeous microphone. So yes, you maybe you'll get an... It's like an EGOT. It's the person who can get the Emmy, the Grammy, and the Tony.
AJ Thomas:
Oh my gosh, I don't know if I'm in that category, but I will say I have the heart of just trying things, things that are unknown. Typically, if you put me in a predictable environment and I have to be there, I'll find a way to make it unpredictable. If I'm in an environment where it is unknown, I'll find a way to build. It's just a certain sense of, I think it's just built in for me, but I started describing myself as a Z-shaped person because I'm also very visual. So I was like, okay, the T shape, I get. We learn about it through design thinking. We learn about it in business school, but the Z-shaped has always kind of looked scattered to everyone. And I guess what I wanted to do was describe a way where that is just like a linear path is not wrong, a T-shaped path is not wrong, a Z-shaped path is also not wrong as well.
And so there's probably many different kinds of these things, but for me, what tended to describe my journey most was the ability to go from one vertical to another domain, take learnings from that, then go back and take learnings from that thing and go to something completely different. And then continuing to do that formula. And then really it wasn't until hindsight and I looked back and I stretched that thing that I found that everything in common, whether I was in sales and operations and marketing and product, building for a sports center, in HR, working in talent, whatever it may be, the through line was always about people, culture and organizations and how to build the future of what that looks like. So I think there was no foresight into it. Everything was just as a reflection. And quite frankly, I got tired of defending myself, as I saw it as defending myself. And everyone's like, you do all these things, how do you do all these things?
And I always get the question, how do you do it all? And I always have the same answer and it's only two words and it's always I don't. I don't. But again, it's not until I had the hindsight, I think I'm a little bit later on in my career now where I can say, wow, when I was doing this, was I like, yeah, I'm totally doing the Z-shaped thing? No. I was like, I don't know what's happening, but I'm just going to keep asking questions that's going to lead me to these different things.
Daniel Stillman:
Yeah, you were just chefing.
AJ Thomas:
That's it.
Daniel Stillman:
So you mentioned the parallel universes, in your perspective, is some of the bars of the Z the parallel universes, or is it more the exploring multiple cuisines and sampling spices and understanding like the salt, fat, acid, heat of other ways of doing things? Tell me your perspective on parallel universes as an important metaphor for a leader to be looking at their work in.
AJ Thomas:
I think a parallel universe. So for example, and again this is the analog, for me was seeing the way that product managers approached user testing. Taking the designing from outside in so that you can design for an experience versus just an event was really valuable for me. So for example, in HR, I see this in the function and I see this with leaders where we'll take, someone's going to have a hard conversation and it's going to happen on April 19th at 2:00 PM because that's the next one on one so we designed for that event. Everything's got to go right and here's what I'm going to say, and we're going to use this method and we're going to ask these questions. But rarely is going into that conversation about, I'm going to have that conversation on the 19th at 2:00 PM, but I want to design it from May 1st backwards.
I learned in product the power of future casting that because you could change the factors. If you just switch the parameters a little bit, you can change the factors of the design of whatever your apparatus is, whether it's a hard conversation or a decision or a strategy. It allows for you to be more aware of the things surrounding your decision making as a leader. And I think the parallel universe is really grabbing some of those things. I mean, each of the different functions are interesting, but there are ways in which finance teaches us about empathy. There are ways in which engineering can teach us about ways in which we approach unlocking hard problems. There are ways in which customer support can teach an engineer the other side of unpacking the huge problem, but then being able to tell the story about the huge problem. So I think there's a lot of those that I tend to think about when I think about parallel universes and what leaders can access.
It creates compassion in your way of being and doing because you're going to then be naturally curious, that's interesting. How does that work in support? Why does the utility of this function process in this way? And how do I get a little bit of that into this? I mean, you're seeing it in recruiting where there's the parallel universe of marketing and people want to take that aspect of building a CRM and nurturing a pipeline the way you would before you launch an event or a product. How is that different from you want to bring a hire into your organization and you want to make sure that they know about that organization? Rather than, oh, I'm going to hire somebody and I'm going to tell them about the company. What if through the journey of them coming to your company, they're already getting to know you? So there's a lot of parallels that I think if we stopped and really got curious around the organization, the utility and the things that they're known for that they're really good at, what could we take in?
Like I said, what's engineering known for? Building great things and tackling huge problems. Okay, well, where are we building great things and tackling huge problems? You could be doing that in any vertical.
Daniel Stillman:
Yes.
AJ Thomas:
But find out what's the best things they're doing in there. And then how do you implement that in your universe?
Daniel Stillman:
Well, it seems like there's actually two flavors of parallel universes that you delineated. One is, and I think this is a classic design thinking perspective of how do I learn about hospitality? Who does hospitality well in the universe? How can a hospital learn about hospitality from a hotel? What can a hotel learn about hospitality from a hospital? What does customer service really mean? And what are all the ways to absorb and cross fertilize excellence in an organization? Which is super powerful. But there was another type of parallel universe you were talking about, which is designing a difficult conversation, not as a, okay, I'm going to have conversation about topic one, two, three and four, and then I'll be done. But saying, what do I want it to be like two days, two months, two years after? Designing for what are all the ways that this conversation could continue?
AJ Thomas:
Could manifest, yeah.
Daniel Stillman:
Could manifest. And that's designing from almost a multiverse approach of this conversation could go many, many different ways. It could go to shit. It could create amazing positive alignment. It could create forced agreement. And it sounds like you're also designing your conversations. I would call this is the question going forwards or backwards in time? You're almost saying which of the many scenarios that are possible do I want to design backwards from?
AJ Thomas:
Well, if you think about that if you're sitting as a CEO, and I coach a lot of founders and advise a lot of founding teams, and one thing I always encourage them is... So for example, I had a CEO that was rolling out their performance management program and was like, "Hey, let's look at this narrative, this deck. Does this look good?" And the question I really had for them was, I mean, that's great. Would your content change if you designed it not for the event you were going to roll it out for, but a quarter after?
Daniel Stillman:
Yeah.
AJ Thomas:
Would there be anything added to that? Would there be anything taken away? And that's how you begin to future proof through scenario planning. I would say, a more elegant and slightly elevated way of thinking about scenario planning is looking at all of the other possibilities. Now, they may never come through fruition because you're really just trying to nail this one specific thing, but I think it makes you more organizationally aware and agile because if it did come up, you'd have at least thought about it.
Daniel Stillman:
Yeah. Well, I think it's very easy to be in survival mode and say like, well, I just need to get this plan so I can get out to this next thing. And you're asking them, what are we really trying to do here? So this gets to the question, the other thing we really wanted to talk about was being a coaching leader or having a coaching mindset based on whatever your coaching philosophy is, which I want you to unpack for us versus a therapist, which is a very different, maybe much more reactive and palliative approach of, yeah, well, let's work through the feelings and get you to the next thing versus a coaching approach, which at least what I'm hearing from you say is what would create a real lasting transformation? A moonshot, if you will.
AJ Thomas:
Impact. Yeah.
Daniel Stillman:
Impact.
AJ Thomas:
Yeah. No, I mean it's really interesting because when I was going through and doing my coaching journey, I was at the service of an executive team and I felt like my utility was really just being a therapist, because you have to hold space. You have to hold space in those spaces. You must. It is a requirement of the job to do that, but it felt like it was really-
Daniel Stillman:
When you say holding space, explain what you mean by holding space for that kind of a conversation.
AJ Thomas:
I mean, really letting people unload on you sometimes because that's what they need because they don't have that safe space to be able to do that. But I felt incapable of holding the right space without challenging as their leader also to give them back their agency, right?
Daniel Stillman:
Yes.
AJ Thomas:
I'm going to say, this is going to sound funny, there's a fine line between a brainstorm and a bitch fest.
Daniel Stillman:
Yes.
AJ Thomas:
And I think coaching helps you give people back the agency that they always had, by the way.
Daniel Stillman:
Yes.
AJ Thomas:
And it's done through a series of unpacking with the right questions. And so as I think about it, my whole coaching approach and again, was really influenced by these four principles by Dr. Angeles Arrien, which I learned through the Berkeley Executive Coaching Institute. It was a really interesting approach in a sense of how she studied the ways that Shaman Tribes communicated with each other, and it's actually been a very near and dear principle to me that I hold in certain spaces when I'm having conversations with folks. Which really, when you're coaching somebody you're really just having a conversation and you're holding that space for that person and then holding up the mirror back to them to make sure that they at least get a playback of what that looks like. And then you ask questions to help them de-risk their problem. And in some cases, that's kind of what we do with Moonshot's too. Identify a huge problem, ask questions to de-risk. That's simplifying it, of course.
But the four principles that have really influenced me is one, showing up and choosing to be present is so important. And I said that so fast, you probably almost didn't catch the nuance. A lot of people are told to show up and be present, are you present? Be present. And I think what Professor Angeles Arrien encourages us to do is be present, choose to be present. Being present is a choice. Being active in that is a choice. You're not distracted by anything else but that person you're having a conversation with, and it really helps hold the container for whatever you're going to be talking about or coaching through. The second principle that I loved was the ability to listen for what has heart and meaning for somebody, and it could be what they're not saying. Like when you ask somebody, how are you? And they say, I'm fine. If you really chosen to be present with that person-
Daniel Stillman:
How are you really?
AJ Thomas:
Exactly. You're like, well, let's talk a little bit about that because you say you're fine, but I'm hearing outside of what you're saying through your physical presence that you might not be. So it's really interesting, it helps you pay attention when you choose to be present. You listen for what has heart and meaning for somebody. Or when they say something over and over, but it's kind of glib but then when you really get to the heart of it, they're like, oh yeah, that actually means a lot for me. That's a really interesting one. The third one which I love is the ability to tell the truth without blame or judgment. You have to do that as a coach. And I think especially with working with leaders, it can be really isolating to be at the top. And again, I work with a lot of founders and CEOs where they're probably the only person that feels like they're carrying the burden of all the things.
And sometimes because they're in such positional power, people will not tell them what is wrong or what they feel could be worked on, or what they feel is a blind spot because one, they either have not been invited, or two, because society or the way in which they've interacted with communities has told them that there's a respect for hierarchy. But the respect for hierarchy is also the ability to be able to tell that person in that hierarchical relationship the truth without that blame or judgment. You can't do that without earning trust of course, that's really hard to do. So it's almost a little bit of a paradox. So it's a very interesting navigation of how you're able to really tell the truth without blame or judgment, but you have to be able to choose to be present, listen to what has heart and meaning for people 'cause that burdens the trust to be able to do that.
And then lastly, as a coach you're never advising. You always have to ask and be curious and hold the space, connect back, connect the dots, but that also means you have to be open to outcome and not attached. Which is why giving advice is not coaching. Sometimes people can flame-
Daniel Stillman:
Fine, fine line.
AJ Thomas:
Exactly. Well, there's also that fine line of being that therapist. You don't just say, tell me more. You say, huh, I really see that this is affecting you.
Daniel Stillman:
So what's the fine line between telling the truth to someone and giving them advice? Because I could see how in a way you're revealing something to someone, that's not telling them necessarily to fix it, but by telling it to them you are telling a truth about the fact that that's something that they could look at.
AJ Thomas:
I mean, it could be something as simple as we've talked about we can say, "Hey, Susan, we've talked about this topic a few times now, and I've heard you say the word I don't mind at all. And then I see you get really passionate about the specific example when we talk about it. Can you tell me a little bit more about that?" Okay, we'll unpack. All right. And then the reason why I'm asking that is because I sense there's a little bit of you do care about this, that you do care deeply because of the way we've unpacked these specific examples. So telling the truth without blame or judgment could just be pointing them to that one thing that they might unconsciously not even know they're doing. Like oh, this is really great, but I don't really care about that. It's fine. You know when people say that, it's fine and then you unpack it a little bit and they're like, well, actually, there's these couple things that have happened in the last couple of weeks. And I'm really curious you've said it's fine three times describing the specific situation, is it really fine?
That's a way of being able to tell the truth without blame or judgment. And also it comes with trust. You got to get to know folks and say, hey, I know in our last conversation, this is where you connect the dots as a coach, I know in our last conversation what was really important to you was that people collaborated well to get to the outcome you were looking for. And now I'm hearing that you think it's fine that they're not. That's really interesting. You find that interesting? So stuff like that where it's you're really bringing those pieces in from what they're reflecting to you is a way to be able to tell the truth without blame or judgment. Without saying, hey, I don't think you really care, but I've heard you say these couple of things where actually you do, don't you? So it's a very fine line, but it's about connecting it and reflecting it back to them in a way where they have the agency to ask that question for themself without you telling them.
Daniel Stillman:
Well, so this is the other piece that I wanted to pull back a layer on, because agency and being directive versus evoking or provoking people to think for themselves. A lot of people feel like leadership is about being directive and authoritative, and you have a value of bringing your coaching skills into your role as a leader. So I'm wondering if you can talk a little bit about how you balance those roles, because occasionally one must be directive, or can you just lead through good questions and deep listening and telling the truth and being open and not directive?
AJ Thomas:
Well, I mean, I'll tell you it's really hard to do it. It's really, really hard to do it because as a leader with your coach's hat on you still have to get shit done, right? It still needs to happen. But again, what I put in the center is whoever that person is am I giving them back agency in how I'm showing up for them? Again, that could be in a question, that could be in a directive to say the only directive is the goal. So that's how I think about it. And if we agree on the goal, you can go kick the ball however you want to. We can agree on the approach, but your technique is your technique, and I'm going to ask. And sometimes I think there are team members who want you to outline it for them, but I always have to say that's great. One idea is to do it X, and then I don't let them off the hook and I will say, what is your idea? Let's hear your idea. Let's see if we can build on that.
If they're lost and they want you to tell them something, I would say, well, how would you approach it? How would you approach it? Okay, that's really interesting. Why don't we build on that with what we know? Let's go back to the goal. So my job as a leader is to align people to the goal because the goal is in service to the mission to help the company succeed. And so as long as I know that's my role, I can continue to play the coach role. If I forget that that's my role, I'm going to be directive and authoritative because I need to get shit done. And I know that's oversimplifying things, but I think for me, that's what I've learned. I used to be the leader that was like, here's our task. Here's what we got to do, da, da, da, da, but what people need is also the context and the agency to say, okay, I can get this done. It is well within my power to be able to do that. And if I'm lost, I can always anchor back and I can anchor back if I'm lost on what the goal is.
Because then people get to see themselves whether or not it's a stretch or it's easy or whatever. And again, it's about giving them back their agency. If I've forgotten as a leader that my job is to clarify the goal and to make sure that the mission is clear, then I will end up being directive and authoritative. There's no other way around it.
Daniel Stillman:
Well, I'm wondering, because I want to talk about your title of chaos pilot, and I feel like in a world of complexity and maybe even chaos, to me it seems almost hubris to say that there is one right way to do things. It seems like a lot of humility comes from the recognition that we are just in a very complex, borderline chaotic situation and our job is to move through that and with a view of alternate worlds and parallel universes, there may not be. You are not coming as a leader saying that there is one best way, and that you know it.
AJ Thomas:
Yeah. You just really can't.
Daniel Stillman:
Unless I'm just putting words in your mouth, but that's the vibe I'm getting.
AJ Thomas:
Well, no, it's true because it's also working in the space that we work in. And I talk a lot about how Moonshot mindsets are accessible for everyone. I think one that I love in particular, an Astro talks about this all the time, is the ability to both be humble and audacious. Which I've then jammed into a word called humbacious. But anyway, it's the ability to be audacious enough to articulate an idea or a path forward, but to also be humble enough to say, I don't understand the entire problem set just yet and so it might not be right so I need to de-risk it, and here's how I'm going to do that. I think it's particularly important when you're working on things that are huge. I always like to say as well, there are people that are really passionate about their work. I can be so passionate about everything that I'm doing right now, but I also feel a sense of responsibility because the work that I'm doing touches the future in some way.
I have three kids myself, and the legacy I'm going to leave behind for them if I'm going to spend 80% of my time at work doing the things that I do is going to be shaped by how the future can show up in the work that we do in the present. And so I think it's really crucial that you don't... I always say, first rule of working on the future is for you to know you don't know it. And anybody out there who is working on the future that says I know exactly what it's going to look like, what we're going to do, here's where we need to go is automatically wrong. Because if I could be so bold to say or audacious enough to say, because the future requires you to constantly ask questions, to constantly de-risk, to constantly test things, and that's fine. But I think in the meta of things, you're always building on something. You're always building on something, and it's never that that one thing that was done is final.
You think about technology and the internet, we're all done for Y2K. Internet is here and now at the rise of generative AI and artificial intelligence or machine learning, there's always something to build on.
Daniel Stillman:
Yes.
AJ Thomas:
Once you plateau at the infrastructure and you create a new operating system, new apps will be built on that. New features and skillsets will be built on top of those new apps.
Daniel Stillman:
Yeah, that we can't participate.
AJ Thomas:
And the cycle starts all over again. So I think, yes, you should assume that you don't know, but be audacious enough to still explore anyway.
Daniel Stillman:
These two values of humble and audacious are really interesting. Lately, there's this wonderful concept of polarity mapping and polarity thinking in management. If you've got these an two angels on your shoulder, one's humble and one's audacious, we can over index on one and there's positives of each pole, and there's negatives of over indexing on each pole to the detriment of the other.
AJ Thomas:
Absolutely.
Daniel Stillman:
Do you feel like you're navigating those two poles in your work? What happens if you lean too much in one way or another for you?
AJ Thomas:
Well, I mean, I think if you lean too much on being audacious you end up really leaving a trail of folks behind you because you're not bringing them into the conversation in a way where you can get collectively curious. I think if you lean too much on humility, you'll never get anything done because you're never going to want to start it 'cause you're always thinking, okay, well, maybe not now, maybe tomorrow. So you got to have a little bit of that-
Daniel Stillman:
Yeah, and why me?
AJ Thomas:
Yeah, the imposter syndrome are settling in rather than having just a little sprinkle of that audacity can really take you there, and then a little sprinkle of humility on the other side. You don't want to change who you are, but you do want to live in the tension of what's the other side of this look like, right? I think some of the greatest leaders out there can see both or four or three sides of an argument, and I always think there's three sides to an argument; yours, mine, and the truth. So it's a very interesting, again, paradox, but I think it's also just very important to hold that tension. I navigate it every single day, and I got to tell you it's not easy.
Daniel Stillman:
No.
AJ Thomas:
It's hard.
Daniel Stillman:
Yeah.
AJ Thomas:
The part that I have to constantly work on is when I get triggered, when do I know I'm being too much of one? It's like your strengths, right? Strengths overused are detrimental to you, but if you have them just toned in the right pocket you're fine. Same thing with much of a good thing. So I think it's not the ability of whether or not you're ambitious or humble. It's not that at all. It's the ability of being able to know when you need to sprinkle a little bit of each in moderation to whatever it is you're working on because some tasks-
Daniel Stillman:
Yeah, or de-sprinkle or to pull back on one versus the other.
AJ Thomas:
Yeah, Absolutely. Absolutely. And again, that's the tension. A lot of people will say, that's context switching. No, it's not. It's being aware that it's there. Half the battle is knowing you're going to encounter that.
Daniel Stillman:
Yes. And to have control in the use of self to say, how may I... 'Cause I have a sticky note in front of me that says audacity from one of my good friends who's actually a therapist. And he was the one who said like, yo, I try to really remember to be audacious, to lean in and say what my clients may not want to hear, but they need to hear. And that's a lever that we can pull.
AJ Thomas:
That is.
Daniel Stillman:
But also let go because as you said, if that's all I'm doing is just pressing the audacity button, I'm not going to get what I want.
AJ Thomas:
Yeah, you won't get the utility of the audacity button.
Daniel Stillman:
Which is not always pressing it.
AJ Thomas:
That's right.
Daniel Stillman:
We've gotten so close to our time, God, we've covered a lot. What have I not asked you that I should have asked you, AJ? Because I have the humility to know I can't know all the things to ask.
AJ Thomas:
I love that. I don't know. I mean, yeah, no, that's a really good question. I mean, I would say we covered a lot of things. I think there's probably some areas where being a mother is a different intersection as well, and a working mother as well, but we can have a whole other conversation on that.
Daniel Stillman:
Happily, yeah. If you coach your kids.
AJ Thomas:
I think it's the other way around. I learn a lot from them. I learn a lot from their very interesting questions. Actually, my daughter and I, we wrote a children's book all from her question of, well, how hard could it be? It was really hard, but it was more of the curiosity of, okay, well, even if we don't know let's just try. And the next thing you know, we've got an award-winning children's book in our hands, which was really awesome. But discovering little things like that. I mean, because I work a lot in the future like I said, it's not just a passion for me. I feel responsible because I'm literally raising three humans who are going to be in the future.
Daniel Stillman:
They live there. That's where they're from.
AJ Thomas:
Yeah, that's right. And so I want to make sure that whatever I pour into it has that consideration in mind, because it can be so easy to be wrapped up in what's happening day to day that you forget that what you're actually working on is never going to be something that you may ever see in your lifetime. At least for me, that's true, right?
Daniel Stillman:
Yeah.
AJ Thomas:
So I think that, but other than that it's all kind of relative to our conversation today.
Daniel Stillman:
Well, I've never asked this question before, what would be the title of this conversation do you think? If you were to give this conversation one or two titles, what would you say this conversation-
AJ Thomas:
Oh, this conversation?
Daniel Stillman:
This conversation, yeah. What was this conversation about? What's on the cover?
AJ Thomas:
Oh, that's a really good one. I don't know, purveyor of perspectives.
Daniel Stillman:
I have a vote for there's a fine fine line between a bitch fest and a brainstorm.
AJ Thomas:
Oh, that's a good one. I got a lot of love for that one. I got a lot of love for that one. That one was just off the cuff, but-
Daniel Stillman:
I mean, there's so clearly so many books that you will one day write AJ, one of them might be these Z-shaped people and it's another really interesting overarching theme for this. So what it's like to be a Z-shaped coaching leader, it's a very different approach.
AJ Thomas:
Yeah, it is. I mean, I'm pondering a little bit more on that. I'm trying to learn as much as I can in the spaces that I'm in. I mean, because there's other spaces of access. I'm a Filipino first generation immigrant. I don't have a lot of folks that I can look up to in the industry that's doing stuff like this. And so in some spaces I feel like I'm breaking into these types of conversations, but I know I'm not alone. And I'd love to see more folks that look like me that have these different experiences in parallel universes talking more about what it feels like for them as well.
Daniel Stillman:
Yeah. Well, thanks for being part of the conversation and being so generous with your perspectives. It's been really, really delightful. Where ought people to go to learn about all things AJ Thomas on the internet if they want to get to know you better?
AJ Thomas:
I'm on LinkedIn, or you can find all of the ways to connect with me on, it's ajthomas.com.
Daniel Stillman:
Sweet. We will direct people there. Well, I think we will call scene.
AJ Thomas:
Woo.