SPEAKER

Quentin Clark - Managing Director @ General Catalyst

Quentin is a product and systems technical leader with broad experience in the enterprise space. Incepted, built, and delivered successful products over many years - from servers to SaaS platforms and applications. He will be joining General Catalyst in January as a managing director.

Prior to embarking on a career in investing, Quentin was the CTO at Dropbox, where he led all of engineering, product, design, and growth. He worked with them through its IPO, its pivot to Dropbox Spaces, and drove the portfolio expansion starting with the acquisition of HelloSign.

"The specifics of the framework are not as important as having one at all. Create some ruler... Like if you're a snail and you're trying to inch your way towards the head of lettuce, and you're trying to measure whether or not you're making progress every day... It doesn't actually matter whether or not you're using an imperial tape measure with inches or the metric system and a yardstick...

You can make up your own ruler! As long as that ruler is consistently being used over and over again. This is why I say it's important for people to have A framework... not necessarily any one framework. And that they come back to it.”

<cite>- Quentin Clark</cite>

He was at Microsoft for 20 years, most of that time focused on innovation - creating new products and value. The last decade of his time at Microsoft, Quentin was responsible for the high-growth data platform business, including SQL Server. There he worked for Satya Nadella leading the whole data platform business into the cloud.

After Microsoft, Quentin was at SAP for two years, first as CTO then as Chief Business Officer where he led strategy and product direction for the platform and ultimately for the whole company. Before joining Dropbox he spent a year angel investing and exploring the VC world.

He currently serves on the boards of Coda, Highfive, and Minio, and has been investing and advising very early-stage companies.

Quentin's Podcast: Equivalent to Magic

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Show Notes

• What does it mean to get “unstuck?” (2:55)
• How do you get unstuck? (5:32)
• How to divide your time between growth, grunt work, & what you’re good at (7:06)
• Where engineering leaders get stuck + how to benchmark your growth using the six areas of competency (10:42)
• How to get people unstuck at scale (15:55)
• Why it’s important to have a framework to benchmark your growth (21:22)
• Quentin’s story of getting unstuck in his career (25:20)
• “Give up” what got you stuck by changing your goals & intention (31:20)
• How to get your company and culture unstuck (37:15)
• Quentin’s podcast “Equivalent to Magic” (44:20)
• Takeaways (45:58)

Transcript

What does it mean to get "unstuck?"

I was hoping we could sort of first begin by getting a little bit oriented to what we mean by getting unstuck. what do we mean by getting unstuck and why is this topic particularly important to you?

Quentin Clark: Yeah, I think one way to think about this is that every system that people are paying attention to, including ourselves, and then also including an organization or a business... The the way that you get things to work and to scale and to be predictable is by training it to be predictable. We want predictable growth. We want predictable check-ins we want predictable feature progress. We want predictable roadmaps. And the very nature of that is countered to the kinds of disruption that creates growth. .

And the danger for people and the danger for businesses is paying too much attention if you will, to that operating and creating that predictability and creating those outcomes because they tend to tamp down on leaning into disruptions and changes that are those opportunities for growth.

And so you have to kind of start to create an intention, if you will around balancing, "Hey, we want things to be smooth and predictable and deliver these results, et cetera. But at the same time, we need to create room and opportunity for the kind of disruption and challenge that will help create growth, to help create opportunity for growth."

And I think that's an applicable thought, both to individuals in terms of how they think about their careers and manage uh, as well as organizations and as well as to businesses.

Jerry Li: Because I guess it's felt comfortable you already know something are able to do something, is it feels good to stay in that state. Both for individual and company. So the intentionality and also potentially the courage as well

Quentin Clark: Yeah, that I think that's exactly right. I mean, you used a good word. It's comfortable. But it's also necessary, right? Like you're running a business, you can't just drop everything that's going on and be like, "Hey, let's let's go explore this other thing." .

Or you can't wake up one morning and say, " I don't really care about my calendar. I'm going to go learn to play the ukulele today. there's a sense, not just of the comfort of the routine and the predictability, but there's also a necessity to it. . There's a greater system, if you will, that is relying on, on that predictability.

So to not just have that intentionality, but to also be willing to create that room in face of those expectations, I mean, Jerry, you're exactly right. It it takes a little bit of courage, And it takes real intentionality to do it well. In a way that's not chaotic and disruptive and doesn't disappoint you know, the systems around you.

How do you get unstuck?

Patrick Gallagher: Let's assume somebody has sort of identified you know, I've over-optimized for predictability and there's sort of this need for my own personal growth and development How does somebody get unstuck?

Quentin Clark: I think the first thing that people should think about is whether or not they've set an intention. I mean, human beings are amazing things. If we can measure things and create goals. Well, it's unbelievable what humanity has accomplished every time we've said, we know how to measure something, and we have a set of goals about how we want this to be and that we can measure progress against. ? There's no reason that our own development is any different than that.

And when I say an intention and I say goals, measurables. I don't necessarily mean like, "Okay, i, as an engineer want to, you know, be involved in you know, so many features over the course of years instead of sprints or whatever. Or I, as a PM have a goal to you know, speak with N different users every month or whatever."

What I'm talking about is, is more meta than that. It's taking catalog, if you will taking stock of "These are things that I'm good at. These are the things that I'm interested in that I'm not yet good at"

And setting an intention around I'm going to make the time and I'm going to make the effort. And I'm gonna create the room for myself to lean into that.

And whether that leading in is learning on your own and leading is building a network and learning from others. Whether that leaning in is doing work you know, within a job that's in areas where you're not an expert. It all starts I would say with an intention.

How to divide your time between growth, grunt work, and what you’re good at

Jerry Li: How do you divide time to spend on those, a few categories of things you just mentioned. Those things you are already know, or you're not good at, but you're interested in the things that potentially important and you need to acquire those skills.

Quentin Clark: Yeah. And, part of this gets into the relationship between you as an individual and the organization that you work within. If you're gonna approach learning in a, in an intention of I'm want to do this inside my work. if you're an engineer, And you're a really good data engineer, but you haven't done much in machine learning. Create an intention of like growing into that, learning into that. To do that in the job place you have to have an, an organization that is willing to give you that room to do that.

And there's a lot to be said about that around you know, psychological safety you know, the room to fail. an organization that is correctly set up to allow people to work on things where they're not yet good at it.

One of the frameworks that use on an off of my career is this thought of 70, 20, 10. It's like 70% of the work you do, you should be good at. Like you're, you're earning a salary. You're often earning equity. You're being paid. So there's something that the system's expecting you to produce for that salary.

But 20% of, your energy, a good organization should allow you to be working on things where you are not yet efficient. You're not yet necessarily competent. You're going to make mistakes. You're going to do this thing way more inefficiently, way less effectively than someone next to you where that activity may be in their 70%, Someone who's been there, done that expert at it. And this gets to, you know, of course engineering experience and ladder levels and all that stuff.

But basically great organizations give you the room... some part of your time to be able to contribute into areas where you're still kind of like feeling your way through it, , and not yet an expert.

And then of course there's 10%, which is you know, it's just stuff that has to be done. Everyone, should take on, we should just peanut butter all the kind of like work that no one really wants to do, but yet has to be done.

As a manager, sometimes that was, I had to go and I did that to like approve expense reports and like approved budgets for capital purchases for data centers. Like am I great at that? Probably not. Is it something that I'm really like learning into and leaning into is cause it's exciting growth area. Not so much. Does it need to be done? Yes, it needs to be done. And often, it's a combination of just the seat you sit in, you have to be the one to do something.

I had someone I worked with who was very senior at Microsoft who went into one of our releases, I dunno one Monday just got this in his head that he needed to go in and clean up, like the error messages and all this stuff that the product would admit to its users. You know, we just gotten sloppy basically.

This is a very senior engineer being paid you know, a lot of money. And definitely work that's below his pay grade. The truth is that work was below everybody's pay grade, but he just took it upon himself because it's like, we all need todo the dishes basically. . And actually that was a great lesson just in terms of what I lead by example.

But the point being, they 10%, if you're not doing some of the grunt work you may not be holding your own.

Patrick Gallagher: And I think there's so much to be said about you know, as a leader modeling the way even not being afraid to get in the trenches. But I'm guessing we'll sort of get into the balance of being mindful of the work that should be in the trenches versus other folks that could be, or should be taking that on depending on the scale of leadership that you're at.

Where engineering leaders get stuck + how to benchmark your growth with the six areas of competency

The next question I was curious about Quentin. So we talked about have an intention, make sure that you have room and effort, and then defining the 70, 20, 10 rule.

Where have you seen, like most frequently that engineering leaders are typically getting stuck in their career paths? What are some of the common friction or sticking points for them?

Quentin Clark: Regardless of its sticking points as you progress in engineering career, like what are the sort of the natural points in the river where maybe the current naturally slows down a little bit and you gotta, kind of row your way through it a little.

I would say one access is certainly every time you go through a scope of or scale of organization change.

There's a tremendous amount of learning that comes with that. And after people have gotten to some mastery of it, that is a natural point where people start to get stuck, right?

You're like, "Well, why am I not being considered for an engineering director? I've been in engineering manager now for X years."

Well, the, question to ask yourself really is " How have I shown that I'm still growing and learning and changing and developing, as I've mastered this level of scale?"

Because it naturally like I say, the, the river widens, and the velocity of the water naturally slows down as a result. And so the nature of the organization change is not going to carry you along and push you to grow. Which means it's up to you!

And so most of the time I find that people end up feeling like they're stuck you have to kind of help them reflect on, have they set that intention? Because something about their situation has led them to that comfort to go back to the word that Jerry used.

And often I've used this framework with people that I call the six buckets... which is effectively thinking about growth in terms of these six different areas of competency.

One of them is management. One of them is leadership. Those are obviously coupled in a related but different.

One of them is vision. One of them is strategy. Again also related, but different. Visions more though, we're going to climb the tallest peak on the planet. Strategy's more of the... "how do we measure the tallest peak in the planet? Like there's no satellites and GPS yet. So like, how's that going to work?" You know, when the British explorers were romping around the planet, looking for stuff there was no Google Earth. . And then you know, strategies, the what phase do we take? How do we get there? How many base camps et cetera.

And then the last two areas are Technical Acuity and Business Acuity. Where technical acuity is that actually you have a cross industry thing. Like you can have deep technical acuity in paper manufacturing . Paper mills, and that's a deep technical area. And business acuity of course is a very horizontal thing.

And very often to help people sort of recognize that they're stuck, you have people go through these six buckets kind of grade themselves and then ask themselves what their grades probably were six months ago? A year ago? Two years ago?

And that exercise alone often kind of jogs people a little bit and says, "Oh, actually I haven't really, this hasn't changed much in a year... that's interesting. So how do I now create the right opportunities or lean into certain areas of growth?"

Because typically the system will also see that growth ? If you're a line lead, You've been doing that for a couple of years and you kind of feel a little bit like you're in that you know, the wide, the river's widened, ? And so it's carrying you along, not necessarily at the same clip and you're reflective about what do I need to do to start to rekindle some of that growth and learning?

You can do things like get more involved You know, upstream in the business or spend more time on leadership that mentoring and development outside your team across teams. Or you can take some time to go dig into other technical areas and start to have your team contributing into more areas of the product.

There's all these different ways you can do that, but it all starts with the observation of the river's not moving quite as fast around me. It's up to me to row. Now what?

Patrick Gallagher: The river analogy I think is incredible is when you're talking about the six different buckets, I can almost see this sort of individual currents of the river. It's such a powerful visualization to understand is your current moving fast or not in these different parts of your own career development river?

Quentin Clark: and it really is the case that there are times in your career where the rivers constricted and so the water's moving faster. And so you're being buoyed by the challenge.

We often refer to this as accelerated or accelerative experiences... Engineering number eight at Stripe, right. That's an incredibly accelerating experience that river is moving very fast. And then the challenge really is can you keep up, can you absorb everything but it's a very growth intensive phase. But very often in our careers, we find ourselves in wider parts of the river and so it becomes up to us to then row if you will, to move faster.

Patrick Gallagher: I was wondering if you could talk a little bit more about some of the differences of the career levels and you know, from somebody in an early management experience to a senior executive, how some of the ways to build this awareness and to get yourself unstuck change at the different sort of stages of your career as an engineering leader?

How to get people unstuck at scale

Quentin Clark: I mean, certainly at different scales things are very different. As a lead, the challenges you have to help people and your responsibility to that is very direct It's very much, you have one-on-one relationships with people and you have the opportunity to really help people understand where they are and move forward and give them that room that 20%... that's up to you now, right? That's up to you as the, as a leader to, to provide as a manager, to provide that room. It's up to you to help them develop a framework for them to challenge themselves. And really encourage them to do that. It's up to you to provide feedback. And we can talk kind of more about those things a little bit later.

So to take you know, one extreme to the other for example, at you know, SAP managing 8,000 people or at Dropbox, 2000 people. I can't create that drive for growth and change with with one-on-ones... it doesn't scale. I mean, I don't know how many years it would take to have 8,000 one-on-ones, but it's probably a while.

So that's not the answers. So the question then becomes how do these things scale? How do you drive that sense of wanting to to get unstuck. So to say, right? To, to break through or to break down the cadences and the rhythms and keeping everything oiled you know, really well and working really well. And to create the room and the drive for more innovation.

And the answer to that is a lot about culture and is a lot about leadership. And some of it's about mechanics. So both those jobs when I was at SAP, I created an organization in Africa called SAP IO, which was an internal incubator and an external seed fund that's still operating and deploying capital to this day and actually doing reasonably well. And it, at Dropbox, we created internal effort around incubations.

And so that's what we mean by structural, Because there's, there's nothing like putting budget against values. As a leader, it's one thing to get up in front of people and say, "Hey, I want people to be feeling like they have the opportunity, the room to explore new ideas and whatever..."

It's one thing to say that, it's another thing to say, "and I've created it a mechanism for it to help catch it and to encourage it and to ensure that we don't just crush it with the machine that everyday needs to be fed to keep the business doing what it needs to be doing."

And so that leadership is important, the structure is important. And also the culture is important. And certainly it is the case I've been fortunate enough not to work anywhere that had a culture that was very much against innovation.

But I've seen them. in my walkabouts of the earth and working with different companies and talking to people... I've definitely seen cultures that have basically an institutionalized pushback against change.

And that is the other thing I think as you scale, as a leader... and you know, when I say that, I don't necessarily mean like You know, CTO jobs, I mean like engineering manager jobs. This question of culture really is important.

And it's not even just company culture and company values that are written on posters inside conference rooms... oh, yeah. Conference rooms. That's something I've forgotten about lately. We'll, we'll get back to conference rooms one day...

but it's, so it's not just a, it's not just like whether or not the company has a support for innovation and driving change and being curious. But how have you localized that to the team that you're overseeing? Because that's often where culture does not end up actually finding its way all the way out to the organization is it gets stuck, honestly and leaders who are not necessarily taking the opportunity to fully prosecute how that culture affects their team and sort of leading from that standpoint.

Why it’s important to have a framework to benchmark your growth

Jerry Li: I want to go back to the earlier things you mentioned, the six buckets. What I feel magical about that is at the moment you lay them out... I start to benchmark myself against those metrics and it started generating right away visibility and also awareness and also a drive to wanting to improve.

So I guess a lot of times people don't have the metrics, they sort of measure themselves against.

So are there other metrics that can be relevant for getting people unstuck in terms of personal growth and career growth beyond those six buckets?

Quentin Clark: Yeah. I think that everyone can create their own frameworks. the specifics of the framework are not as important as having one at all is the message, create some ruler...

Like if you're a snail and you're trying to ensure way towards you know, the head of lettuce and you're trying to measure whether you're making progress every day. It doesn't actually matter whether or not you're using an imperial tape measure within inches or the metric system and a yardstick, you can make up your own ruler. As long as that ruler is consistently being used over and over again. This is why I say it's important for people to have A framework, not necessarily any one framework and that they come back to it. And they create their own sort of sense of how they measure that.

In terms of other frameworks that I've seen people you know, use and engage with over time... you know, One of them has to do with an evolution of the role. that you're taking in a given problem.

So a problem exists. Someone was able to describe the problem to me, and they were able to describe to me the remediation of that problem. And they're able to give me the instruction set to execute that remediation. And when you started your career as an engineer, that's usually what it's like. It's usually like, "There's this thing we need done. Here's how we want it done and here's things you need to do. And here's all the toolkit you're going to use do it. Please just go fill out all the code..."

And then from my description, you can kind of see what those steps are in terms of maturing and evolving you know. Where ultimately you, you want to get to the place where you're identifying the problems. And then beyond that, you start to ask yourself the question, "How often am I anticipating problems that have not yet materialized?"

And I think one of the good benchmarks to use as a, as an engineer and as a manager, honestly is... when you get to some level of competency in a craft, you start to have the experience where you can start to anticipate the problems before they show up.

I'm working with a team today that I won't go into details of cause the investment's not announced...

But they gathered this group of engineers to have the kind of competency where they've built a system that will scale. And going to scale for the next five years and the next million users. And I have zero anxiety about this whatsoever. And it's because they took people with experience.

And that measure of how often can you anticipate problems that might occur applying this architectural principle to this problem space or using these design primitives, whatever they are, whether we're talking about you know, data structures or communication system, whatever it is. But these architectural primitives. you know, where are their bottlenecks going to be? And in the needs we're going to have over time... Will those, or will those not become issues? And so this you know, incredible substrate can be laid down, by these experienced people because they're able to anticipate those problems.

And so, that's one of the things that I think may is a hallmark of people that have done a really good job. I talk about building careers as a pyramid, but laying down that pyramid. As you do that, and you get a little further off the ground, one of the characteristics is that you can anticipate problems.

And the metaphor works really well because when you're, you know, when you are a little higher up off the ground, you can actually see things coming over the horizon. Right? Those metaphors actually you know, work well together.

Quentin’s story of getting unstuck in his career

Patrick Gallagher: The point you made about anticipation, I think is so powerful. And that team sounds incredible. excited to excited for the public launch to hear what they're working on so we can take some notes.

This is more of a personal question from your own journey, Quentin... When you're thinking about getting unstuck in your career, is there a story that comes to mind from your experience where you found yourself stuck? And how did you get yourself unstuck?

Because when I'm looking back at the, story arc of your career, you sort of had several different iterations of who Quentin Clark is at different phases of what you've done as an engineering leader, as chief business officer now as the managing director of general catalyst.

You've sort of had a forcing function to get yourself unstuck and to reinvent or reimagine your career a bunch of different moments. And so we'd love to hear a moment that stands out to you and what that change was like?

Quentin Clark: I'll share a story... the story is perhaps a little self-effacing, but I think it's an important one. There was a phase in my career and I won't bore you with the details of the hierarchies and the job titles and all that stuff at Microsoft...

But there was a phase of my career where I definitely felt stuck where I was in a job. The measures of career progress at that time at Microsoft, which isn't just like the salary and the promotions and all that stuff, it's also like where you're being involved. What kinds of forums being pulled into, and that kind of thing. Where it's just, clear to me I felt like I had slowed down. And I didn't really understand you know, sort of what was going on. And sometime during that phase the thing that unstuck me was, I had someone else that I had worked for in the past, pull me over into their division to work on some project.

They're just like, "Hey, I just need you to come do this. Someone I trusted very deeply...

People that have heard me talk about career building and one of the lessons I often talk about is just follow great people, Develop deep relationships, follow great people. Much good comes of that. Most of my career, when I've been really in the groove that's definitely been true...

And any event. So I did it, right. I went over to this other group, but on paper, it was a step back career-wise. Again, in that sort of time and place and the Microsoft machinery.

And what I realized some number of months later was that I was stuck. I was stuck of my own making. And I didn't really even know it.

The problem with not making progress was I had one of these moments where the river had naturally slowed down because that scale of that job, it's bigger, it's time dilated. The river, widened the current was moving as fast... And I didn't recognize yet that it was incumbent upon me to be the one to row faster, . That I was not recognizing the skills that I need to lean into to get the next level and intentionally working on those.

And it took a bit of a reset to kind of wake me up to that. But I believe very much a very valuable lesson in my career. And so you know, I don't mind sharing that.

And one of the takeaways I think from that also is to recognize that the things that got you to where you are... it's worse than they're not even necessarily the things that are going to get you to the next stage. Often they interfere with you getting to the next stage.

I mean, just take the simplest most obvious example. You move from an IC engineer to a lead. Just being a great coder, if that's all you do, if that's what you focus on, it'll actually prevent you from being a good manager.

You have to be willing to not produce you know, whatever it is, 50 hours of great coding a week. And instead, give that up in favor of a set of activities that you... again, to use Jerry's term, because it's a good term... that you may be very uncomfortable with at that stage. And you're uncomfortable with them because you're probably not very good at them. But that will change, . That will change.

One of the rubrics that I've talked about over time is strength. And strength is really like just the ability to carry weight. Just think of it that way, metaphorically. ? it is a function of talent. Which can be honed and developed and shaped and encouraged. But it's talent times the sum of skill and experience.

So not enough just to have inherent talent. You have to put the miles in. And it's not enough just to put the miles in. You have to be putting miles into areas where you may end up having talent at it. Right.

I will never be a great pianist. Like that is just not in the cards. you know, I took piano lessons as a kid... I don't really know what wrong, but my brain is not wired for it.

My brother-in-law. He can hear a tune once, sit at a piano and work it out within about a minute. It's just, his just brains wired for it it's just wired differently! He has inherent talent for it. No matter how many miles I've put in front of a piano, I will never be great at it. That's okay! I have other talents and I'll lean into those.

Patrick Gallagher: It reminds me a lot of, some of the insights that I got from reading Malcolm Gladwell's book Outliers about looking at the different, unique opportunities you've had in your life, that you either have had more experience or earlier opportunities to take shots at than other people. As a way to, for me, it was a framework to think about "In my own experiences, what are different things that I've done or experiences that I've had that may have given me an earlier opportunity?"

The example he shares is of course, is Bill Gates, getting access to being able to code at UC Berkeley earlier than most other human beings on the planet as a unique opportunity. The comment you made about giving up, what got you to where you are so that you could go to the next phase was really interesting because I think about, for me, I have a horrible time giving up those things. Because I think this is something Jerry and I talk about all the time is like, as soon as I feel like I've got something, Jerry will ask me, "like, okay, so what's the next step? Like, how are we going to transform this process to unlock new productivity here?"

And I'm like, I'm furious because I'm like, "But I just figured this out. Like, what do you mean I have to give this up?"

Do you have any thoughts about how to help people give up the things that got them there?

“Give up” what got you stuck by changing your goals & intention

Quentin Clark: Yeah that's a, a tricky one because it's so against human nature, I mean, if you, become competent at something, your emotional reward system, the dopamine hits. they're hard wired at that point. You know, being a really good engineer, that dopamine hit of like unlocking architectural problem or, that moment when you compile the thing actually works correctly, right. Or having the confidence to do the check-in you know, whatever it is..

You're chemically rewarded! It's our lizard brains that are telling us Not to give those things up. It's not just a matter of like rearranging your schedule that day. Right? You will just naturally drift from the intention because your brain is yelling at you that it needs that dopamine. I think a few things one, you need to seek and be in an environment with this, what I refer to as psychological safety. A place where you are going to be allowed to fail at the things that, that you're trying to work through and trying to learn into and all that stuff.

You need to... again, this is back to a framework of it doesn't matter what your your measuring system is, have one. Write it down!

In a, one of the things that organizations do when they want an outcome is they write down goals. We literally write them down. Google made a big fuss about it and like named it OKR's! But they're not the first business ever to write down goals. Just you know, as an FYI you know, Google did not invent goals. They invented a lot of good stuff! Goals, not one of them.

But nonetheless, the power of writing these things down... it's interesting that people are willing to treat so many things in their lives that way. People write down goals they have. They'll say them out loud. You mean writing down is actually often a very powerful and effective technique, but even just saying them aloud also is effective technique.

Like you know, "I want to be married by a certain age. I have certain financial goals..."

People say these things out loud and then they strive towards them. They feel a little bit more held accountable to them by their friends and family, because they've talked about these goals. And one of the things that makes great life partners is, when you share those goals and they help you with that accountability system.

And it's interesting that we're willing to do that in certain parts of our lives. And then other parts of our lives, we avoid it. like we actively avoid it... And the thing I definitely encourage people to do is write these things down. It's okay if it's in some private folder somewhere like you can put it in a desk drawer! Or put it in your sock drawer! I don't really care so much where this thing is written down. I just think you should have it written down.

The act of having to think it through enough to articulate it concisely enough in written form and have written it down is one of the steps that you can take.

And I occasionally do this technique where you know, whether it's a mail exchange that triggered a thought or it's something else I was thinking about. I'll write myself a note, in email. And then I'll you know, control H that thing off into the future. . And so six months, this piece of mail pops back up. And you know, more often than not, I read this thing and I'm like, " what is this thing about again?"

Right? But, you know, I, I figure it out!

It's a tiny mechanism to hold myself accountable to have you kept focused on this? And You know, returned back to this.

So there's things that I'm learning to do as an investor. I've been in this job about a year and a half now and there's still things that I'm learning to do. And so I have these emails that are showing back up in my inbox that are from three months ago or six months ago, a year ago that says, "Have you figured this out yet?"

And because if the answer is "I haven't" then probably more likely than not the reason for that is, is I've not set the intention to do so. It's not for lack of opportunity. The venture industry has not magically shut down you know, over the last year. So it's not for want of opportunity. It's for a lack of you know, the discipline to focus on it.

Patrick Gallagher: That's an incredible practice cause I'm just thinking like the long-term priorities that you know, you know, you should be focusing on are really hard to keep track of because the time horizon is not necessarily a daily activity it could be a six month or a quarterly thing to revisit some of those outstanding questions.

So I'm like, "Man, there's some emails I need to command H and revisit in a couple of months..."

Quentin Clark: yeah, it's, true for organizations as well. And you know, one of the things that I believe is that our tools don't do a good enough job helping us with this. Both from the HR tooling side, which is one of the reasons I invest in Eightfold. And from the day-to-day kind of work management team management side. Is one of the reasons I invest in this company called Range.

You know, Range is a product that lets you have that intentionality. One of the engineering managers at Adobe she basically has this thing she says around the check-ins the daily check-ins, it's a, ritual about being Mindful. right? It's back to that intention. and setting that intention, having written down, sharing them with other people, it just does. It goes a long way. And if you can do that in a way, again, the comment about psychological safety, if you can do that in a way where people feel the safety to share what's really going on. Then you get a lot out of that.

Just like with your partner, right. Where the magic's about the reason you are willing to share certain life goals with your partners, is because you feel that emotional safety that if there's turbulence in achieving those things there not going to be like, "Well, you're fired, like see you later."

Right? that we all strive to you know, have the kinds of partnerships in our personal lives where know, we're providing that safety and we're benefiting from that safety. And the workplace it should be no different.

Jerry Li: And also the importance of being nudged to make progress. That daily reminder, can play a very big role in a lot of cases.

Quentin Clark: It's a simple thing, right? It's a simple thing, but it's a contract you have with yourself. You wouldn't buy a house without a contract, but people are willing to set their life intention without a simple written note to themselves.

Interesting. Okay.

How to get your company and culture unstuck

Patrick Gallagher: A moment to transition the conversation, to talk more about the company level, because you had mentioned a couple of times about different ways to introduce different structures and programs. Or how to get your culture unstuck with all of these things.

And we were talking about people and individuals, organizations are ultimately just collections of people. And that as an engineering leader progresses, their career becomes oftentimes more dependent on their ability to impact and expand the impact of larger groups of people.

So when you're thinking about getting a company unstuck versus an individual, how is that different? And how does somebody have to change their approach or thinking in terms of helping people get unstuck with their growth and development?

Quentin Clark: I think it's, It's a great question. I think that... we've talked a lot about intentionality and psych and intent and all that stuff and having frameworks for kind of measuring and whatever.

But inside an organizational situation, additional things you really need is situational awareness. You need to be able to understand where you are, relative to the system around you and recognize that it is a system.

There's this organizational sociologist, I guess named Barry Oshree who wrote this framework about the hierarchies that are inherent inside organizations. Not even the ones that are like literally in the org chart. I'm also talking about the ones that are you know, about how things work and the power inside of organizations, et cetera. And how infrequently people are really leveraging their peers. And this is this concept around power of the middles. And really leveraging their developing relationships across peers to carry out will of the organization or the people in the organization.

I think that's important because, again, a framework of intentionally taking the time to understand and the nature of how things get done and you know, what people's motivations are and why are you things are happening in a certain way. so that you can figure out how to unlock and get unstuck in your own agenda.

Just the existence of being in the middle, inside a company, right. Whether you're in engineering, or a PM lead, or a design manager or director. and yes, even Vice Presidents, right?

At all levels, they live in an existence where there's the will of people above them. There's the capabilities and the will of the people that they're responsible for. And then there's the agendas. Of the people around them.

And the total net sum of these things, excel could not calculate. Excel would be like, "Circular loop logic problem, like does not compute..."

And would throw up on you. Because the reality is there's a lot of conflicting direction, if you will from above you and below you and around you.

And the way to get through this is to really understand... What are the capabilities? What are the desires, where the fears of all of those constituents and work in the awareness of that.

Actually, I use the same framework uh, on the career side, where I talked about leadership and management, vision strategy, and then technical and business acuity...

if you take that same framework as columns. And then as rows, you write down like yourself, "What are your competencies here? and what are your objectives?"

And then you create a row for your boss and maybe your boss's boss. Same thing, like to your best judgment, What are their Competencies? And, what are they skilled at? And maybe what are their. weaknesses. And everyone has them, so it's okay. What may their objectives be? What are they after? do the same thing for your peers and do the same thing for the key people in your team.

And then you start to look for patterns like, like any other interesting engineering problem. You just kind of look for patterns. And you can find things where it's very clear that certain agendas are going to be able to move very quickly because there's like an alignment of, competency and interest.

And so like, "Hey you have like five different things you're trying to get done? Find the one that's lined up to those things first!" Right? As a way to build some success and gain some trust in these kinds of things.

There's also situations... one that I refer to as the "Two Bozo Rule" where if you have two people in a reporting relationship that are both poor in some area, weak in, some area... that's dangerous! Because the currents can get stuck underneath them and has a hard time leaping over to the next layer. That's an opportunity, especially if you find the peers that around you that are strong in those areas to work together, to build enough momentum, to break through things.

So you know, an example this may be... if you're trying to change some cultural norm, because it's interfering with the work of an organization. But your managers, this is not what they focus on. They're just like, "Whatever, some stuff written on the wall and a poster. Like, why are you talking to me about this..."

And your boss's boss has also kind of of that mindset... The only way to break through that is by having a consortium, if you will, a coalition, federation of peers that do care about it and know it needs to change! That are willing to help get. This agenda sort of really listened to.

Because at that manager level, if you're that manager that's like, kind of not focused on it, doesn't really care about it. If you have five-year Director reports that show up that are like, "Hey man, some things are going to change."

You're kind of like, "Okay, I must listen to this. They're not letting me divide and conquer them. This is a force to be reckoned with."

And so I think this is about. You know, human beings, we're really good at effecting things, we can measure them. And so it's just another framework to measure something and to be reflective on that. And it can be very insightful when you kind of take stock of what's going on around you and figure out, "Okay I can't do this brute force. There's gotta be another way."

Patrick Gallagher: Really quick clarifying question. So when you say objectives... is it their individual goal or is it like their function goal that you're trying to map to when you're filling out that framework?

Quentin Clark: It's both really. It can really apply to both and very often, and of course, as you get to be a more senior you know, manage an organization. Your objectives and your organization's objectives tend to be incredibly aligned.

There are definitely some things like in terms of learning and other things you want to have an influencer there, you have a personal life there too as well. It's kind of less those things I'm speaking to more so than it is the needs and the will and the objectives of the organization.

But even on the personal front there is this tremendous opportunity to look at that data, if you will, and say, "Okay, I really want to learn... I want to like lean into building my business acuity. That's not who my boss is, maybe my boss is just a very deeply technical CTO that is spending time of the business. And most of my peers aren't. Which means I have to go outside the organization to do this."

That mentorship is going to come from, "I need to go form relationships with you know, the head of sales or with a you know, biz ops leader or somebody like this!" Right. In order to kind of get involved in enough things and start to learn. Learn that better..

Quentin’s podcast: “Equivalent to Magic”

Patrick Gallagher: Thank you Quentin I know you have a hard stop at five. I just wanted to quickly reference and bring up your podcast Equivalent to Magic And so I just really quickly wanted to ask you, you know, what have you loved most about some of your conversations on Equivalent Magic?

Quentin Clark: I appreciate you asking about the podcast. Equivalent to Magic is a podcast that my partner here at General Catalyst, Steve Herrod, and I embarked on I guess now several months ago. In fact, we had our first conversation about it before we were sent to shelter in place. So that tells you how long it was in the making.

And as you know, it takes a lot more work to do a podcast in a than it appears on the surface! But it's, been just this unbelievable opportunity to, Actually to help these leaders stop and kind of reflect and share a little bit about what they've learned, because you know, it takes someone like Jay Parikh who is you know, running engineering up until recently Facebook... his day-to-day life is get stuff done, get stuff done, get stuff done! It's not "Stop, reflect and teach."

Right? And so one of the things that's been remarkable about the experience of doing that podcast has just been how open and grateful people are just for that, that opportunity to take that moment to give back in that way. That's just been very, very humbling been a lot of fun to work on.

Patrick Gallagher: That's great Jerry and I are big fans of show

and yeah. Also you fall under the category of somebody who is taking the time to reflect and to teach.

And so for that, Jerry and I are both incredibly grateful for your time and for sharing all of your lessons and insights with everyone here today.

Quentin Clark: So happy to do it, Patrick, Jerry. Great to see you guys. Of course.