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Conscious Career Growth (part 2)

with Wade Chambers

August 16, 2020


Wade Chambers - CTO and SVP of Engineering @ Grand Rounds

Wade oversees all aspects of engineering and technology innovation at Grand Rounds. With more than 25 years of engineering leadership experience, he has deep technical domain expertise and a successful track record of scaling teams and leaders, market-defining technology innovations, and business growth for companies of all sizes including Twitter, TellApart, Yahoo, and Opsware.

Before Silicon Valley, Wade served in the military and the White House Situation Room.

“And the more that you can come up with, well, what does it mean to be a great manager? Or what does it mean to be a great leader? Answering those questions for yourself and actually getting to the point where you have confidence and are willing to stand behind it because it's well-reasoned and like it's a principled point of view... will help you improve”

- Wade Chambers


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  • How to measure success, “win, and increase your capacity to win” (2:32)
  • How to increase the potential of people on your team (8:24)
  • How to get unstuck in your career (12:31)
  • The 3 “buckets” to help identify where your career growth is stuck (16:53)
  • How to maximize learning and growth from the books you read (21:23)
  • How to get to the core principles that drive your behavior (25:52)
  • Wade’s final thoughts on closing the gap between where you are and where you want to be (29:38)
  • Takeaways (31:41)


How to measure success, win, and increase your capacity to win

Jerry Li: A common question for a lot of engineering leaders, even at more mature companies are, how do we know we are doing a good job? How do we measure the success for a manager and a whole lot of people?

Yeah. And companies don't have a clear idea. So that creates a problem for evaluating performance. If you don't know how to evaluate consistently and have a clear understanding, it's going to be a problem. Something shared earlier, in past events is your goal is win and increase the capacity.

Can you share more on that so that, the audience can have a common understanding of what great looks like.

Wade Chambers: We touched on it earlier and I do think you're right. I know you're right.

I have had, leaders at multiple levels. and like you asked the very simple question of like, how do you measure success? Or what do you think success looks like. And it is wildly different from, common things that I hear is ... my job is to make my team happy or my job is to, create a good culture or my job is to, be a shit umbrella.

You hear all of these things and, , I kind of understand why, people say a lot of those things. That may be an attribute or a thing that you focus on to help, your success and your team success. But like, that's not the primary motivation.

I like "win and increase your capacity to win" just because it's pretty simple and memorable, but if you're not executing... and by win, are you creating business impact for your company... Is your company better off because of the results that you're shipping and are you able to successfully ship repeatedly, It's like, can you GSD, on the stuff that matters.

And there's a lot of things around just like execution, engagement, coaching team members, all of those things that just lead to winning, that's not good enough.

if you had the same team a year later, should they be able to do a hundred percent of what they did the previous year or significantly more? And of course opinion is that they should be able to do significantly more.

I like that, idea of, in 12 months you should be able to do 1.5X, and probably even more. But like how, like, what does that mean? And I think that, you have to help people understand like how to break that down. And I think that most time people come into, engineering manager roles as a senior IC, like how have I experienced the world? And you kind of think about things like there are individuals that are part of teams that ship things for the company.

And in reality, that's how most engineering managers, proceed with their role, who are the people on my team? Who are the individuals? Let me understand them. Okay. Is the team functioning? Can we do standups? Are we shipping? Is the quality where it needs to be? Do we need to adjust some process, et cetera? Are we shipping? Are we getting things done for the company? Good. Hopefully it hits some key company metric.

And the reality is, is like managers want to think the other way. Why does the company exist? What are we trying to do?

What are the results that would most significantly improve our ability to do that thing that the companies needing to do?

If we wanted to reliably produce those results... what would the team need to look like? What cultural norms would need to be inside of this team? What, type of individuals would we want on this team? What would be the optimal process? What would be the interaction styles with other teams in the organization?

Because then I know coaching and the mentoring and the hiring that I would want to do in inside of that team.

And so if you start to think about it as like, I need to increase my capacity to win, you've got all of these tools at your disposal.

You can improve on the execution side of things on like, can I make the process more streamlined? Can I do all of these types things around engagement or helping to coach people?

Or you can look at the increasing the potential of your team, are we working on the right things? Do we have the right mission, vision strategy? Do we have the right principles for what we're focused on?

Prioritization, objectives, key results. Do we have, the right team structure, team types, technologies, all of those things in place. Have we attracted the right people? Do I have the right talent level inside of my team. Are they top performers? Are they aligned with what we're trying to do? Can they use critical reasoning better than most? Do they have the needed strengths? Do they have a growth mindset?

If you find that you've got a limitation on the potential of your team, that's your job. to figure out how to move through that. You may have to move somebody out of your team to pull somebody into your team that will unlock the potential of your team.

And so if you think about it as an X by Y matrix of where on one side of it is potential on the other side of it's performance, like you have to figure out where you're at on that and how you're going to move it up and to the right.

And it may be that the team's executing super strong for what you've got. You've just got a low ceiling because the potential is low. Then you have to go deal with the potential.

If you've got a high potential team, that's just not executing, then you have to actually work on the execution side of things and getting the performance where it needs to go.

And so you're constantly, almost like an etch-a-sketch, trying to figure out like how to move the performance of the team to the right and the potential up consistently. And if you're not actively engaged, and figuring out like what part of the team that you need to be helping with... you're probably not doing your job successfully as an engineering manager.

How to increase the potential of people on your team

Patrick: With the limiting potential, what's the input to increase a team's potential? Is it related to some of the things you've mentioned about ego and blind spots? Is it coaching people to see those things to increase their potential or...?

Wade Chambers: I really think about it as like three categories of things in like potential. Number one is the what and the why. You can imagine, like you've got high potential people and they're super great, but there's no vision for what they need to do.

Well shit. Okay. Like we need to create a North star. We need to make sure that everybody understands what success looks like and how we prioritize things. So the what and the why needs to be really good.

In the middle you've kind of got the how. Right, like you can imagine amazing people. We've got this very lofty idea of what we want to... but there's no structure. There's no how we're going to do this? Like, how are we going to interface with other people? What are the tools that we're going to use? What are the norms that we're going to do inside of this? And so that can be a very limiting thing.

And the third area is the, who. And by far, it is where you've got the most leverage. Right? Like you get amazing people on your team and, amazing things can happen, assuming that you've helped with the what and the why and the how.

There are three things that I normally think about with each and every person on the team. Do they get it? Do they want it? Can they do it? A good friend mine, constantly talks about those things.

The challenge with that is, probably at least 60% of the people that you meet with can do it. They have the base potential. The IQ is there. They understand technology, they understand all of these things. And yes, they could do it.

What I really find, is the challenge is... they don't get it. Right. It's like they don't understand alignment with the company and like how to get to a better business judgment or the thing that's holding them back. Their ego is getting in the way. They've got blind spots that they can't get around.

You can help try and break that up so where that they do get it. And you need to do that in a way that it's a gift, not punitive, right? Like, If you can establish a deep connection with another human being and actually build good credible trust with them. Then hopefully they don't see it as like, I'm trying to feel good about myself by telling you something negative about you. But instead, ah, this is the thing, right? Like if we can work through this, your career or even beyond the company that you're currently at is going to continue to unfold.

If you can help people see both their strengths and like where they're really awesome and where their growth areas are and like how we could go through that, brewing beer exercise to like help them get on the other side of things... then they can hopefully get it.

The real challenge though, is if you get it, there's always a price tag. There's always a gap between where you are and where you want to be. the real thing is like, can your ego, handle that? Or are you willing to go through the discomfort of stepping into an area of incompetence and actually building out new strengths?

that's gonna suck. Imagine if you've got, you know, a decade or more of experience, and you're super good at what you do and the thing that's holding you back is something you've never focused on. Right? Like as you, as soon as you start to focus on that area, you are going to feel immediately incompetent. You're going to feel like this is bullshit, right? Like I just need to go back to doing what I was doing. And like that thought will set you back. And so as a manager, if you can help people both feel competent as they're going through that and other areas, but help coach and mentor them through that area of growth. Then hopefully they can get from the, I get it. I want it. I'm going to do it.

And their manager is alongside of them to actually give them feedback, set up the structure, help them get to declarative knowledge, help, give them an opportunity to practice in that area that they need to grow in and then measure it and give feedback as they go through it... hopefully in like one-on-ones and behind closed doors. But in a way that actually unlocks their forward progression.

How to get unstuck in your career

Jerry Li: Along that line , when people cool, you know, career are stuck, how do we apply some of the learnings you mentioned earlier to consciously look through those?

Wade Chambers: Yeah, that's super hard, I like the quote that's attributed to Einstein of "a problem cannot be solved at the level it was created or the level of consciousness that created it."

And so oftentimes you find individuals that are stuck because they don't get it. If they got it, they, would move forward. And so they're stuck as a result of not getting it.

And so... if you are listening to this, and , you feel like I should be further along. I feel like I've been repeating the same thing, just in a slightly different company for the last few years. And gotten a little bit of a pay bump every time I've went, right? Like the The real underlying competencies haven't changed.

My hope would be is that you can find somebody who actually cares about you and that you can have this discussion that helps move through it.

And I think that that would largely look like... let's try and be very conscious about what we want to be true. Like what do you want to accomplish out in front of you? what do you want to be true that isn't currently? Do you want to be, you know, the VP of engineering? Do you want to be a staff engineer? Do you want to be, and maybe it's not title driven. Maybe it's like, I want to be able to accomplish this. I want to be able to build this type of a solution. I want to be able to influence, executives. I want to be capable of leading a team in this new way.

If you can identify what you want to be true, then I think that you can step back from that and say, who do you know that like exemplifies. what you wish was true.

And not from the standpoint of like measuring yourself against them necessarily. But like, what we're trying to do is , look outside of yourself and say what causally makes them successful in that role. And if you can get to ahh right, they've got really good leadership skills or they're very good at cognitive reasoning. Or they have the ability to inspire others, or whatever that case is.

If you can kind of go through that and break that down. Then you can start to identify, is there a gap between where I'm at and that truth that gives them competitive advantage in that role if you can identify that gap. Then you can start to break it down and say, Oh, the neuroplasticity is a thing I need to start working on this. Let me identify some of the most leveraged, portable areas of growth, and focus there first. Can I find a coach? Can I find an opportunity to practice and just start chipping away at it?

The 3 “buckets” to help identify where your career growth is stuck

another thing that I think is helpful inside of all of this is, starting to think in buckets of areas that, are helpful.

Daniel Goleman famous for his books around emotional intelligence, put out a book called social intelligence. You can go read through that and it breaks things down into basically the three big clusters.

Number one, cognitive skills. Do I understand problem solving to understand critical reasoning? Can I apply that to a particular domain? can I learn how to do programming in this language? et cetera, et cetera. Like, can I apply my intellect to a problem and create a solution that's out there.

Area number two is personal skills. Are you self aware? Right. Like, can you truly understand where you're at? Do you understand, what gets you to fight or flight responses? that's very different. I mean, like, you can get to a place where you're aware, but you're not modulating yourself.

And so the second thing in there is like, you know, self modulation, right? Like I can choose a different response based on some stimuli. I can choose to not react to Jerry saying, "I don't know how to brew beer or I don't know how to run a podcast." and I can, instead of being defensive, like I can immediately go, "wow, he's right. Okay. Well, this is cool. This is something new for me to learn." Right? Like that can be a chosen response and you can choose to, self modulate in a lot of different ways.

The third area on the personal side is achievement drive. You can choose to be optimistic. You can choose to actually get up each and every morning and put your shoulder to the harness try and move it forward. Achievement drive is a thing that you can consciously choose to do, and neuro-plasticity again, right? Like the more that you focus on it, the more that it will become true.

So cognitive skills and then personal skills. The third bucket is social skills. And that is social awareness. Can I read a room? Do I understand how decisions are made? Can I listen empathetically? Can I understand, you know, I, I offended Jerry when, when I talked about his beer making skills.. Can I understand like when somebody shut up, and, , in some way, I triggered them in a way that I didn't understand. All of the social awareness allows you to have empathy for other people and be able to engage better with them.

That's very different than social impact. Can I move the team? Can I move the room? Can I provide, inspiration to others? Can I communicate effectively? Can I invest in other people? Can I develop them?

Any time that you kind of think through some limitation on output level of responsibility, business impact, you will probably be able to go to one of those three buckets and say, "ah, here's the limiting factor, ? , because I'm not doing this, this isn't probably proceeding." And so that's a lot. Right? But the more you can consciously sort of look at yourself first and say , this is in my area to control and let me make sure that I understand, consciously, what is important to me, where I want to be. If I can do that, then I can try and find the gaps that prevent me from being there. I can find mentors and opportunities practice in that. And then I can also start to diagnose specific competencies and areas that will help me move forward along those lines, by just looking, cognitive personal interpersonal and, you know, different types of behaviors that use combinations of those things.

and you can get on a path where I can actually do introspection and reflect and find areas that I think are very valuable to me. I get it. I want it. Now I can actually start to move through it.

Jerry Li: That's a very comprehensive framework to reasoning about a lot of things. I think people can apply that in many different places and using , the spirit of seeking truth and not letting the ego or other things or the projection to the world come in to play and prevent you from seeing what's real versus what is not.

That's something I learned from this conversation and I think it's profoundly, impactful.

Wade Chambers: We skipped over a lot of things, but, like I think that if you just start to look at this you'll start to discover a lot inside of this

Patrick: Yeah. I think the biggest thing I struggle with is oftentimes I don't know where to look. And so just even talking about cognitive skills, personal skills, self modulation, achievement, and social impact. Now I know where to look. Like that's the part that I feel like I'm always, I'm always challenged with is what are the right questions to even ask...

How to maximize learning and growth from the books you read

Wade Chambers: I wouldn't outsource my judgment to any one author or anything along those lines. But if you read two or three things, and there's some overlap in there, then you can start to look for the underlying principles that are behind that and decide for yourself whether that's actually true or not.

And just that getting to that core truth of like, yeah, no, that's a real thing. Then can help bolster, the, strength to actually move through it.

And it's just like, how conscious can you be about breaking it down and deciding what's most important for you?

Jerry Li: The thing about reading book is that I think you mentioned a really important word, which is try to understand, because if you just take what the books are saying , and you read enough number of books, you start get conflicting opinions. And it's really hard to reconcile.

What you mentioned is try to understand, so that based on your own understanding, how the world it work s , you take pieces incorporating that, building your own framework.

I think that's the part. A lot of people may miss, like, they'd read a lot books. but the key part is how much they actually understand on their own.

Wade Chambers: Yeah.

there's an interesting thing in that like, I will oftentimes, Watch somebody tweet of, "I'm going to read a hundred books this year."

And so the real question that I have behind that is like, why? If you're trying to get to declarative knowledge, then a hundred books is, is fine. Right, like it can fill you in on the details of how leader X might've thought about subject Y et cetera, et cetera.

And like, it's just good for, you know, like, you'll recall it at some point in time. But if it's around growth and skill development... right, like, as soon as you read it, if you're picking up the next one, you're actually not trying to convert it to action. Like you're not giving neuroplasticity a chance to actually have any impact on this.

And so then the question becomes is like, okay, did you write a book report for the book that you wrote? How are you trying to put it into action? What's your opportunity to practice on that book that you just read?

Every book that I read along those lines, I'm constantly trying to figure out what are the key points and how am I going to put it into practice? Otherwise I shouldn't read the book in the first place. And I actually mean that some degree, because what's the last book that you read that you were like, Oh, wow, that was really profound. That was really interesting.

Okay. Are you using it? Well, you know, I tried it once and it didn't work out, but like, it's still cool.

And like, as soon as you make that statement, you've got scar tissue and you've started to discount the principles in the book, as opposed to your application of those principles.

Right. And so then you're much less likely to revisit oftentimes you can, build up scar tissue and not go back and actually try and drive the real value of the content that you were looking at.

Instead, , you look for the next thing. And that's sad that you've invested hours spinning up on something and didn't figure out how to get full value out of it.

Jerry Li: And I guess the definition of done, like we talk a lot in engineering ... for learning, is you get unconsciously competent that you have the muscle memory, you can do something without any effort.

Wade Chambers: Yeah, I'm mixed on, some of those things, like if it is core and extremely high leverage. Yeah. I think you have to get to the point where you're unconsciously competent, you know, get your 10,000 hours in.

If it is a sometimes food, right? Like it might be okay to get to 30-40 hours and like, know that, okay, I understand it. I know how to do it. And if I need to, I can go back and refresh real quick and probably spin back up on it. I've gotten it far enough along that I know how to do this, like riding a bike. for me, it is like, is this a sometimes food or is it an all the time food? If it's an all the time thing, swing all the way through. Just , get to the point where you are that top 10%. Get to competitive advantage.

If it's something that you need to do every now and then get to declarative knowledge, get to procedural knowledge, but like don't waste that time that you could be spending on things that will have higher impact to your career and life.

How to get to the core principles that drive your behavior

Jerry Li: What are the other tools you can recommend for people to learn and develop themselves?

Wade Chambers: Oftentimes I think about it's learning that net new thing, the thing that you're missing other times, I think it's almost, about exploring what you currently believe and figuring out whether that's true or not.

love the old quote that " losing an illusion makes you wiser than finding a truth."

There's something profound in that of like, because you've never, had access to somebody who challenged your belief system, or you've never read anything along those lines, you continue to build on this false idea and then it, it comes out in really awkward ways. I think, just the reflecting and , listen to understand as opposed to respond. If you're constantly listening to be wrong, It will help you understand why do I believe that? What are the assumptions behind that? What are my biases? Like? Do I have recency bias because of the place that I just worked. And so I think constantly reflecting and inspecting your own motives and ideas is a great way for growth.

and along the same lines though, is for example, what is leadership, right? Like I'm not going to put you on the spot there, but like, just that thought of what is leadership? Woof... boy that is a wide open question isn't it?

But how would you answer that? Like how would somebody personalize that to say, okay, here's what I believe. And the more that you can come up with, well, what does it mean to be a great manager? Or what does it mean to be a great leader? Answering those questions for yourself and actually getting to the point where you have confidence and are willing to stand behind it because it's well-reasoned and like it's a principled point of view... will help you improve.

Right, like for me, it's a combination of two things. I think leadership is all about influence, right? Like, can you influence somebody else? And how many people can you influence and like having a compelling message and inspiring people and helping them see the same truth that you see. And there's like a lot of that. But everything that I just said, car salesman can do too. Are they a leader? Well, so that brings in a very different dimension into it.

okay, for the thing that you're influencing around who benefits? Okay. So if YOU benefit, that's not really leadership, right? That's manipulation. If you think about the team, the company, the industry, the United States, the world, et cetera... benefits from your actions and your high influence, right? Like to me, that's leadership.

If you're high in influence, but only you're benefiting that's manipulation. If you are low on influence, but the team benefits, that's like a great team player. And if you are low in influence and low on who benefits... well, you suck. Okay. , that's not right. Like, it's a different answer there, but like, that's not a leadership thing along those lines.

So then you can start to think about that. And it's like, Whoa, it's really hard to influence people, but then how do I do that in a way that I'm constantly thinking about what's the right thing for the company or my team or those around me or my family? t puts it through different filter as a result.

And so the more that you go back and address some of those basic questions that you have on, like, what does it mean to be a great leader or a great manager or a great partner or, a great executive? It will force you to go deep and actually get to the core principles that are going to drive your behavior.

Wade’s final thoughts on closing the gap between where you are and where you want to be

Patrick: Wade, we have covered so much together. We've talked about neuroplasticity, we've talked about coaching and learning and getting past declarative knowledge to unconscious competence.

We've dug into the anthropology of a company, how to measure success, and ultimately, how to get people unstuck with their career.

Before we closed, do you have any final words of wisdom to help people get unstuck with their career or to help them close that gap between what they know and where their current abilities are?

Wade Chambers: The only thing else that I would say is that oftentimes you don't know how to start and no one said here's how you should process this. Here's how you should think about this.

The only thing that I would offer out there is, every profound lesson that I've learned, has been because there has been somebody who is incredibly gifted and very generous with their ideas and their time. And you think you're bothering somebody, but the truth is, is that if you ask... probably most of the time somebody is going to respond in a way that helps you. And so there's a ton of great people out there that very much want to contribute to making you successful. Be vulnerable. Reach out. Ask.

Jerry Li: And that's essentially how this community was built by asking for help. There are so many people like yourself are willing to spend time and share to learning and, and that's essentially how we are connected .

Wade Chambers: I wish this had been around back in the, , the nineties. I could have definitely benefited.

Jerry Li: I can't really imagine myself in that position. I feel this if existed when I first became a manager, I probably make less mistakes.

Cool. Thanks very much for spending time. We started, .

Wade Chambers:

Always enjoy it.

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Conscious Career Growth (part 1)
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