#162 - Scaling for Success: People Priorities for High-Growth Organizations - Andrew Bartlow

[00:01:12] Episode Introduction

Henry Suryawirawan: Hello again, my friends and my listeners. Welcome to the Tech Lead Journal podcast, a podcast on technical leadership and excellence. If you haven’t, please subscribe on your favorite podcast app to get notified for new episodes. Tech Lead Journal also provides bite-sized contents our LinkedIn, X, Instagram, YouTube, and TikTok.

My guest for today’s episode is Andrew Bartlow. Andrew is the co-founder of the People Leader Accelerator and the author of “Scaling for Success”. In this episode, Andrew discusses the common challenges faced by high-growth organizations and offers strategies for successful scaling. He emphasizes the significance of organizations creating a unique people’s playbook and cautions against blindly adopting best practices from other companies. Andrew highlights seven essential people practices organizations should prioritize, which includes organizational structure, learning and development, and culture and engagement.

I hope you enjoy listening to this episode and learning the importance of establishing a people playbook. Please share it with your colleagues, friends, and communities, and leave a five star rating and review on Apple Podcasts and Spotify. So let’s go to my conversation with Andrew after some quick words from our sponsor.

[00:03:18] Introduction

Henry Suryawirawan: Hello, everyone. Welcome back to another new episode of the Tech Lead Journal podcast. Today, it’s a bit different episode. My guest today doesn’t come from technical background per se, but he’s from the people’s side of the background. Today, I have Andrew Bartlow here. Really, really happy to have the chance to discuss with you today, because I think people management, people organization is something that I also have passion to do research about or study about so that we can all learn how to actually scale organization, especially in a high growth organization. So Andrew, thank you so much and welcome to the show.

Andrew Bartlow: Thank you. Hey, really glad to be with you.

[00:03:55] Career Journey

Henry Suryawirawan: Andrew, I always love to start my conversation by asking my guests to actually share a little bit more about yourself and if you can share with us your major highlights or turning points that we all can learn from, that will be great.

Andrew Bartlow: Well, I’m a, uh, lifelong or at least career long HR guy, human resources. I’ve been in this field for coming up on 30 years, across a bunch of geographies globally, across a bunch of different industries, not just tech, but certainly including tech. And maybe rare within the HR world, I actually intended to get into HR. I didn’t just fall into it. I went to school for this, have all the certifications, and I’m a lifer. So my major highlights, you know, really were making a great choice to enter a strong educational program for HR. I got my Master’s at the University of Illinois. And actually I just accepted a adjunct faculty position for them. So I’m coming full circle. I’ll be teaching the students in the same program that I graduated from many years ago.

And that program exposed me to the best academic minds, and frankly, the best on campus recruiting coming out of the really strong master’s program. So the market was hot, had a number of different job offers at the time. And these were from companies that were targeting high quality HR people. So right there, that was already an important filter. These were companies that came to campus looking for really strong HR people, not the more administrative, more tactical, more operationally oriented folks.

And I started my career with Pepsi. I won’t mention every stop I had over the 25 years, but a really meaningful move that I made was about three years in at Pepsi. This’ll date me, we were in the midst of the dotcom boom. And I was tapped to head up human resources at a growing international company as the 25th hire. We were a technology consultancy already with operations all over the globe. I was number 20 something. We took it to 120 something people.

And then with the dotcom bust, we went outta business. So that the cycle of growth and death happened very quickly, and that, that was my first experience in my early twenties leading the HR function. And for the next couple of decades, I stayed in HR and ping-ponged between, you know, high quality enterprise organizations and more entrepreneurial, smaller organizations. And my capstone in-house, I was the Chief Human Resources officer of what is now an S&P 500 public company called Invitation Homes, a real estate tech company. Back in 2018, I left them. And I hung my single shingle as a consultant, and I wrote a book that Columbia University published.

And today, I’m an operating partner for a private equity company. I’m an investor in a number of different venture funds. I do angel investing. And largely I work with founder-led, investor-backed tech companies, helping them to be more successful.

[00:06:56] Writing “Scaling for Success”

Henry Suryawirawan: Thank you for sharing your story. I think it’s really, really interesting. I mean, you have been, you know, in the people line of job, right? And today we’ll be learning a lot from your experience and also the book, which is titled “Scaling for Success”.

So you mentioned that you have been working a lot with the tech company, high growth tech company as well. But in the first place I wanted to ask you, maybe if you can share why did you write the book? Because in the background of story of the book, right? You mentioned something very interesting for me. And startup always experienced this kind of a growth stage, right, where maybe it started from a small teams, but suddenly, just like you mentioned your experience, right? You experienced a high growth suddenly within maybe a year or so. And then, you know, like what made you motivated to come up with the book?

Andrew Bartlow: Yeah, I think the root of writing the book was in part based on my location. I live here in the San Francisco Bay area in the heart of Silicon Valley. And I’ve seen companies grow massively and the venture industry, you know, really explode. And I’ve seen and been a part of people and management practices at these high growth organizations. Across the decade plus period of the war for talent, as everyone was trying to grow so quickly, as capital was being poured into these companies. And frankly, I found the management practices to be lacking. Frankly, I found that the people management could be done a lot better and in a much more sustainable way.

And so I wrote the book with the idea in mind that more leaders and more HR or people leaders could benefit from some of the mistakes I’ve made along the way and some of the research backed findings that my co-author and I could bring to the table. So to summarize, why did I write the book? To help companies manage their growth better. I saw a huge opportunity in people management.

[00:08:52] High-Growth Organization Challenges

Henry Suryawirawan: Yeah, so I’ve had experience as well in a few high growth companies, not only just startups, scale-ups, but also in big tech companies, right? Where, you know, suddenly in such a short of time we hire a lot of people. So definitely very, very challenging, you know, bringing a lot of people in, a lot of cultural differences probably in the beginning as well for those people. And also how to manage, you know, such a large growing number of people suddenly. Maybe if you can give us some common challenges that you normally see in this typical kind of high growth organizations regarding people management.

Andrew Bartlow: Sure, sure. Well, the common challenge is usually the same thing as the most common positive thing that’s happening, and that is growth. Like, growth is wonderful. And that’s what you want. You know, revenue growth, headcount growth. But that also creates its own challenges. More money, more problems. More people, more problems. Or at least, more complexity. So as you add headcount, you should probably also be adding management layers to your organization. Not everybody can work for the founders. Although that’s often a challenging turning point as well, is founders starting to delegate and hiring a management layer between them. So with headcount growth and the bringing in of new leaders and new managers, that can accelerate your organization and help you meet your product roadmap a lot faster, or it can be really difficult for your organization to adapt. I joke a little bit in the book, you know, you can burn up the competition or you can burn the house down from the inside. And having a strong management strategy in place can, you know, help you get the best rather than the worst out of a growing organization.

Maybe one more comment around a typical challenge and that is changing tracks. It’s changing your mindset about what got you here was being very entrepreneurial and, you know, quick and dirty and fast and iterate. But what gets you through scaling is adoption of more process and a little bit more structure. And that can be really hard for entrepreneurial founders to accept. What got your startup off the ground was you making stuff happened. What will help you scale is adding some process and some structure to how you operate.

[00:11:11] Goldilocks Zone

Henry Suryawirawan: Yeah. Or there’s this phrase “what got you here won’t bring you there”, right? So I think that’s always a good learning. And what I can see as well for many startups and founders or co-founders, right? They are not probably experiencing all these people management. I think that’s also one challenge by itself where they probably need really, really a lot of guidance on how to set up this processes, this structure. They need to start thinking about people. Maybe it’s a benefit, performance management or, maybe, firing people, you know, bad performers, and things like that.

Andrew Bartlow: Well, I just wanna reinforce what you’re saying there. Like a lot of founders are technical founders, or they’re business founders. It tends to be people on either ends of their life and their career, like very early stage life and career or very late stage life and career. And the very early stage of the folks that are, you know, typically getting the venture funding and need to learn a number of disciplines that they don’t know already. And I’d suggest that they should strive for a Goldilocks zone. Like don’t be so focused on your people that you’re afraid to make the tough calls and change people out or hold people accountable or be clear about what’s expected of them. But also, you know, don’t treat people like they’re disposable. And you can certainly move into micromanagement, you know, very quickly. So I write about the archetype of a prophet who’s a great visionary but can’t execute. Or a mule driver who, um, you know, is really hard on the team and believes themselves to be the only decision maker. And neither one of those archetypes are ideal. But striving for that spot in between where you can get results and do that while bringing your team with you.

[00:12:52] People Playbook

Henry Suryawirawan: Yeah. In your book you mentioned that all these type of companies need is actually a people playbook, right? When do you think those founders should start thinking about this kind of playbook? In your book, you mentioned there are a few stages that probably all founders have to go through. And maybe if you can elaborate in high level what kind of stages that we should think about when we want to build or iterate on our people playbook.

Andrew Bartlow: I don’t know if now, a couple years after having written the book, it’s been released for a while now, if I agree with the concept that everybody needs a people playbook or that it’s a single people playbook. I think your plays change over time, and so should your company. And so, like, I guess as a comparison, if I have two young daughters and they play soccer. And the plays that they run for their under 10 year old soccer team will be different than the plays that a high school team runs, which will be different than the plays that a professional soccer team would run. And so too in business. Like you should have different plays at different stages of your evolution. So I don’t think there’s one playbook.

But more generally, like what is in the people playbook, that’s be clear about your goals and communicate with massive clarity to your team what you’re trying to accomplish. Now clarity doesn’t mean detail. Like I see a lot of groups go way too far on OKRs and monthly or quarterly individual goals, you can really overdo it. But clarity at the company or team level is really essential.

And I think maybe a second area that I’d really reinforce is focus on the basics. Lots of startups get wrapped up in trying to do everything. We’re trying to recreate everything or, you know, we are special in every way. And boy, I would just really encourage disruptive organizations to try to disrupt the product or service that you have a startup in the area of. But don’t disrupt accounting. Don’t disrupt people management. Don’t disrupt basic things that bring stability to your organization. You want your organization to be able to function and have a narrower window of what really needs to be special and unique for you as an org. So be brilliant at the basics. I think is a really key idea.

[00:15:13] The Danger of Best Practices

Henry Suryawirawan: Yeah. When you mentioned about these basics, I think a lot of startups normally adopt best practices from, you know, other scale-ups or successful big tech companies, right? Things like having perks, having, you know, this foosball table or something like that. So what is your thought about, you know, adopting best practices from these kind of companies?

Andrew Bartlow: Yeah. I, I have a strong reaction to the idea of lifting and shifting, air quote “best practices” from some company that it’s very unlike yours. I think it’s really dangerous. You know, if you read about what Google does or what Meta does or what Elon Musk is doing at Tesla, how similar is that organization to your little startup that has 20 people that are spread across the world that might not even have seed funding yet. Like the practices at big, successful, profitable, mature organizations that have been around for decades should be… like, it’s a different playbook. It should be different than what you’re doing at the very early stages. And likewise, let’s say that you’ve raised a couple rounds of institutional capital, maybe you’re on series C. Seed will be different than C, which will be different than public company. You should just expect that.

So I think that best practices are a trap in a lot of cases. And you should really start with first principles thinking. What’s best for us? What do we need? Or at least apply a critical eye. Not everything needs to be new. You know, I just talked about be brilliant at the basics and don’t recreate everything. So, once again, here’s a Goldilocks zone. Don’t lift and shift what other people are doing. Don’t recreate everything new, but find that spot where it works for you. And just apply some critical thinking before you, you know, use somebody else’s best practice.

Henry Suryawirawan: Yeah. So maybe also in the past, right, where, you know, funding was easy, there are a lot of money around, right? People can spend more. But I think we are in the current era where, you know, funding starts to dry up. People starts to think about revenue and profitability. And probably that also brings down a lot of these kind of fancy people management tactics, right? So I think it’s always good to find the right spot that works for all of us.

[00:17:29] Crisis of Leadership & Autonomy

Henry Suryawirawan: In your book, you also mentioned these two kind of key milestones in the typical high growth organizations, which is the crisis of leadership and crisis of autonomy. When I read that part, I find it very insightful. Maybe if you can give us some explanation about these two stages.

Andrew Bartlow: Well, I really borrow that thinking from a great management scholar, Larry Greiner, who wrote about evolution and revolution in organizations way back in the 1960s for Harvard Business Review. So, like this is an example of some research that’s been around, some ideas that have been around for a long time, but may not have entered the popular discourse. May not have been talked about as much as they could.

So to your question, what is this crisis of leadership? In the very early stages, many organizations and startups are intentionally chaotic. It’s everybody working on everything, generalists making stuff happen, getting stuff done. And you’re able to do that, because you’re a small group that’s highly committed, that probably knows each other pretty well. That sort of startup is, again, a very archetypal and typical. But once you get a little larger, once you get to 20-ish people, at that point, your founder or founders probably can’t manage every single person. If you have 20 people, can a founder like really know what everybody’s working on all the time? Probably not. Can you have regular contact with all those 20 people? Yeah, but it’s probably a light touch.

So at some point in there, there needs to be more direction. And that’s the crisis of leadership. When you move from that chaotic figure-stuff-out environment to you’ve got enough scale that you need to bring some clarity, some communication, a little bit of process and structure. You’re probably bringing in your first manager sometime getting close to 20 people, maybe sooner than that, or moving somebody into that role. So that’s the crisis of leadership is where you need to start formalizing some things. And I think that’s a very common and predictable stage to go through. And knowing that that’s a challenge as you get to a certain headcount can help you move through it more successfully.

The second crisis that you mentioned, and actually Grinder spells out several and correlates that to a number of different elements inside an org. I, you know, strongly recommend, you know, if it’s in the show notes that the audience googles Larry Grinder, some really good stuff out there. Another crisis that organizations can predictably face is the crisis of autonomy. So usually the solution at one stage becomes the problem at the next. So we just talked about you need to have some process and some structure in the 20-ish people. Many founders do that kicking and screaming, resisting with every ounce of their core. But then they start to build the process and structure and they see what it can do and they fall in love with it. And they go too far. The pendulum has swung. And then everything is being tracked by everybody. Individuals have OKRs. You overdo, you move into micromanagement. And, you know, typically that’ll happen in the 50 to 100 headcount range.

Not for everybody, and some organizations get there sooner and some get there later. But if you can name it, if you can name like, hey, we’re moving into the crisis of autonomy. Or we’re moving into micromanagement, people don’t wanna be there, don’t want to admit it. But you’re probably tracking stuff that you don’t need to and there’s too much control in the system. That’s a crisis that needs to be resolved through clear delegation, through loosening the reins, through empowering managers. And so these are some, you know, typical challenges the organizations face very predictably at certain headcount sizes.

Henry Suryawirawan: Yeah, thanks for elaborating those two typical crisis, right? I think when I read that, I find it really insightful, especially if you have a chance to go through all these cycles. You will typically see this kind of crisis of leadership and crisis of autonomy.

[00:21:34] Lack of Role Clarity

Henry Suryawirawan: And I think one thing that many, many startups also struggle is about the clarity of the roles as they grew, right? Because, for example, those early members of the team, right, suddenly maybe they got promoted or they got shifted to different, different types of roles. Maybe if you can elaborate what are some typical challenges you see about these kind of transitions of roles or transitions of skills for those early members.

Andrew Bartlow: Sure, sure. Well, there are a couple of concepts at play here. You know, one is you’re moving from generalist to specialist. So as you start out as a very small team, you might be doing product and engineering and design. And then you grow a bit and maybe you separate product from engineering and you look for product experts and maybe somebody that was pretty good at doing EPD altogether as being like a solo concept. They would come up with a concept, they’d come up with a design, and then they would code it themselves. You’re looking for a greater depth in a certain discipline. And that could happen in operations or finance or other areas, sales and marketing as well.

So moving from generalist to specialist is a transition that organizations will naturally go through if they’re having growth. And that can be hard for the people that were really successful that help get the company to that next stage who are great generalists who figured stuff out. But now the expectation is that they’re going to lead a group that they don’t have nearly the level of depth than that the people that they will need to hire in. So that’s a challenge and that’s a change process. And some decisions need to be made there around like who will stay with the organization and who will depart. And you can do that in a graceful way or you can, you know, drag it out.

And there’s also, second transition, is between individual contributor and manager. So somebody that’s doing the work in a hands-on way versus someone that is guiding, directing, leading the work and coordinating the team. I often see startups resist the idea of management, in general. Like, management isn’t real work. We all code here, or we’re all hands on, and there’s pride in that. And that often ends up being counterproductive, like management is real work. Coordinating, coaching, giving feedback, providing clarity, breaking ties, making decisions. Like, if that’s not real work, I don’t know what is. Cause that facilitates all the makers, all the developers, all the engineering, all the creation needs that guidance. So the move from individual contributor to manager or leader is another transition. That’s often challenging and really difficult.

And then maybe one more, this idea of chaos to structure. There’s a great meme for this. I, I should dig it up. From pirates to navy. There’s this great photo of Jack Sparrow with Johnny Depp, you know, who’s the rude and rough looking pirate to somebody in a very nice starched uniform with shiny buttons in the Navy. And so the idea in a startup is, hey, we’re, we’re in this kind of chaotic environment where everybody’s doing everything. And there’s pride in doing something different and disrupting, and that’s the pirates. But the transition is at some point you become a real company with people that have mortgages and kids and are looking for health benefits. And they’re not all founders anymore. And, you know, for some people it’s a job versus a passion. When does that mix start to shift? When does the ownership start to change? And over time, as your organization grows, your leadership or the culture of your org should probably start to shift towards being more navy and less pirate over time.

Henry Suryawirawan: Thanks for giving the overview of typical common challenges or common transitions, right, that all high growth organizations will have to go through. I think all those resonate with me as well. And thanks for sharing that.

So in your book, you come up with, you know, the basics, right? The basic key practices that high growth organizations need to think about. Maybe it’s time to dive deep into there.

[00:25:45] 7 Key People Practices

Henry Suryawirawan: So I think in your playbook, right, you mentioned that companies need to think about a plan. They need to have a plan rather than just go through with the motion and kind of like putting some practices in place from, you know, some best practices out there, but have a plan. And then master only the basics. And the last one is actually to consider both the content and the context. But maybe if you can give some overview what kind of the key practices, what are some of the key practices that leaders or co-founders need to think about whenever they start to come up with this plan.

Andrew Bartlow: Yeah, I would break down this, you know, problem into a couple of different categories. And important though, these are kind of false separations. Everything’s linked. Everything’s connected to everything else. So you can’t just focus on one and let the rest sit usually. So I’ll call out these individual areas. But it’s really important to think about it like a web rather than individual columns, because everything connects to everything else. So a couple areas to think about around people practices and management practices and scale ups. And I’ll list them first, and maybe we can talk about them in a little bit more depth.

Structure. What does your organizational structure look like? Like who reports to who? Who does what? How much autonomy versus empowerment? Or how much are you inspecting what you expect? Structure is one.

Second area. Talent acquisition. How are you finding and hiring, selecting and onboarding new team members? If you’re growing and scaling, this is probably a big focus area. Talent acquisition, that’s area two.

Area three I’d label learning and development. Particularly in startups that tend to appeal to people that are earlier in their career, that are on a higher growth trajectory. One of the big compelling reasons to join a startup is that there’s this widespread belief that your career will grow faster than it would at some big, mature, stable established organization. So there’s an expectation from your team members, generally, I’m speaking in generally that they’ll grow. And so how are you delivering on that? But not just that sort of early career expectation. As a growing organization, how are you keeping up? How are you fostering learning and development, because your product or service is probably changing, and the way that you operate is probably changing very quickly. So learning and development is a key area of focus.

Fourth. Culture, engagement and communications. I’ll lump these together. So organizational culture. What does it feel like to work somewhere? How do you operate? Engagement is employee engagement. What’s the sentiment of your team? Do they wanna be there? Are they expending discretionary effort or are they looking for the next pay raise around the corner and they’re just mercenaries ready to go. And communications. I think internal communications, which is often the magic wand. So again, these things are really strongly linked. How are you communicating with your team? What information are you passing on? With what cadence? You know, that that’s a, that’s a, a culture engagement and communications is a key area.

And the last couple, performance management is important. We talked about like, some groups can be too slow to move on from valued staff, and some groups can be too quick. And how do you handle that in an organization? So performance management is important. And I think I’d link goal setting there. So call it performance management and goal setting. It’s tough to manage somebody’s performance if it’s not clear what they should be working on or what the expectations are. So I think those are inextricably linked.

Another area is legal and compliance. It’s an area that’s not fun for anybody to focus on. It’s a bit of a must do, but it can be a real landmine if you’re not aware of some of the most common issues. And it’s not hard to protect your company from the most common issues. And so I focus with a bit of a US-centric perspective on the legal and compliance matters. But there’s some crossover to other parts of the world as well.

And maybe underpinning all of these things. So I just listed a bunch of stuff and a lot of it’s kind of HR and management consulting speak. Like how do you resource it? How do you set up a people team, or an HR team, or a management team? Like you can do this with no HR people if you try. But what’s the best way to construct a team to help your organization deliver on all these things. And all of these things, again, together, work together. And so you could be fantastic at one and fail at another. And there’ll be ripple effects across your organization. So I just listed a lot of stuff and I’m happy to go into as much detail or as little as you like.

Henry Suryawirawan: Thank you for these overview, right. There are seven key practices that you outlined just now, right? And also in the book, they become one chapter each, right? So, let’s go through some of them, because I believe we won’t be able to cover everything for sure. Uh, let’s go through some of them, which I think I have a lot of interest in.

[00:30:44] Key Practice: Organizational Structure

Henry Suryawirawan: The first one is about organizational structure. I think it’s given in almost all these high growth organizations, maybe before they work with the co-founders, small team, maybe one team even. And suddenly when they hire a lot of people. Now you need to start thinking about structure. Maybe hiring more managers, hiring more leaders, and you start to have layers in between co-founders and maybe individual IC. So maybe if you can maybe highlight a little bit, what kind of typical problems that we need to think about the structure and what we should do about those problems.

Andrew Bartlow: Yeah, I love it. This directly reflects the structure that we have in the book. We try to break it down to what is the problem, what’s the plan, and what’s a very short list of basics that will be helpful to managers in most situations. So the problem around structure is that as you grow, as you have more workers, more headcount, your complexity explodes. It’s actually exponential complexity rather than linear, because you have more people with more context in between them. So that complexity becomes really challenging to deal with. So generally, the way the plan that my co-author and I would recommend and shout out to, Professor Brad Harris at HEC Paris, my brilliant co-author. You know, there’s a short list of things that can help with that.

Generally, it’s about defining some role clarity. Helping people understand what they should be doing will reduce conflict. And so you can overdo that, and you can underdo that. So, you know, shoot for that Goldilocks zone. You can’t have a job description that’s 17 pages long that gets updated every three weeks as your organization changes. And I’ve seen organizations like really go far as everybody wants more detail. So it’s definitely possible to take it too far, but provide clarity around who’s doing what and who gets to make what decision.

There are a couple of good tools to do that, like a RACI matrix, Responsible, Accountable, Consulted, Informed. It’s also known as a DACI or an ARCI or a RASCI, like pick your acronym, but make it clear who does what and how decisions are made. I think another basic around org structure is make sure that your structure makes it clear who makes decisions.

Like, if you have an engineering leader and a separate product leader and a third peer design leader, who makes the decision there? Does it always go to the CEO at that point? Because you have three peers and they’re expected to sort it out themselves. In that case, if you have three peers and they constantly need to interact on decisions about what your software product will look like or how it will function, you’re setting up your organization for conflict. So I would encourage strong role clarity, write it down, and set up structures so that, hey, maybe you have a CTO that sits on all three of them that can make decisions before it has to go to the CEO. You know, figure out what works for you. But make sure that your structure enables clearer decision making.

A couple other areas, and Henry cut me off if I’m going too long on any of this, stage-appropriate leaders are really important. I don’t know if I came up with that term if I coined it, but I’ve been using it a lot. And a stage-appropriate leader, that’s the idea of a generalist versus a specialist. That’s the idea of pirate versus navy. The idea that there’s some people whose skills and preferences are better suited for the chaotic early days of make stuff happen, get it done, be a generalist. And there’s some people whose skill sets are better suited for a more structured, more process oriented environment with specialists. And as you’re building your team, you don’t wanna get too far ahead of yourself. Like if you have 20 people, you probably don’t wanna go out and hire a bunch of folks from Google and Walmart. They’ll be way outside where you’ll be in the near term. But what makes sense for where your organization is now? And ensure that the people that you’re bringing in have at least a good mix or a realistic shot at being successful in the environment that you’re in and that you’re headed towards in the near future. So stage-appropriate leaders are really important as you build out an org structure and a management team.

And maybe last comment in this area is around structure. There’s a concept around, it’s a dual concept. Span of control. That’s how many people report into a manager. You know, often you’ll see a founder or a CEO with a dozen plus direct reports in the very early days, because they wanna know everything, they wanna, they’re not ready to really empower a manager yet. That’s a high span of control. Like think about what a really manageable span of control is. And that span is probably a lot lower when you have people that are geographically spread out, when you have people that are at different career stages, you can’t be as autonomous or independent. When you have people that are in different functional disciplines, each one of those things add complexity. So you wanna have lower span as you have more complexity. So CEOs, I would suggest their span should be no more than four to six, maybe eight on the outside to be really effective. And then you think about your organization, you can have high span where you have very similar jobs. Like, let’s say that you have an inside sales team that are constantly doing email marketing or, you know, a lot of people doing a lot of the same thing. Or a Zappos call center. They can have 30 people that are under one roof in a call center in Las Vegas, that has a call center supervisor over 30 people, because it’s a highly measurable job. The roles are very similar. The career stage is very similar, so you can have a big span there. So take a look at span.

And then the other piece is layers. Often in seeking career growth, people will wanna manage other people. That’s how you get promoted, that’s viewed as a measure of success. How many years have I been a manager and how many people do I manage? I’ve seen a lot of stacked column organizations develop where you have one person managing one person, managing one person, managing one person for no good reason. And what that does is it creates a lot more distance between the decision makers and the people doing the work. Think about the old telephone game with a can of soup and a string tied, but tied between it. You know, communication fidelity reduces the more layers it has to go through. And so every layer that you have means that those people that are further away understand the decision makers less and have less of an impact and an influence on the people that are making the decision. So try to minimize layers. Or have a good reason for a layer. And don’t just maximize span, but try to optimize span to make sense so that the managers that are, uh, in charge of a group can do good work. So happy to explore any of that, if that’s useful.

[00:37:49] Politics & Power Dynamics

Henry Suryawirawan: Yeah. Really interesting, ideas from you. I think all are really relevant, right, as you go through all this organizational structure. Some of these questions will definitely pop up. Another question that I typically have in mind when we introduce these kind of structures, I think, you covered it a little bit as well, right, about the span of controls and the layers and all that, is about people being politicals. Or maybe there’s a power dynamics happening when you have this kind of structure. Any kind of tips that you think founders or leaders need to think about this politics and power dynamics?

Andrew Bartlow: Oh boy. I mean that, that’s a real, that’s a real challenge, especially as an organization scales and there are personal relationships developed with some of the early hires. I worked at one organization, I’ll change the name. Let’s say that the founder was named Bob. And again, changing the name. We would joke about friends of Bob. Friends of Bob got special treatment. Friends of Bob would go talk to the founder CEO and go around three layers of management. Friends of Bob were good workers and really valuable, but super disruptive. And the CEO founder, like wanted to maintain those relationships, valued those people, trusted those people, but they were no longer directly reporting to the CEO for, you know, a lot of good reasons. That’s an example of a situation where political dynamics can get awkward where people start jumping the chain of command, start going around it. And as you get a bigger organization and, you know, you get distance, you get questions, you get lack of clarity. You get partial information along the way.

I think the best way to have minimal politics is to write stuff down. If you’re operating in an async environment, if you’re in a distributed workplace where you’re communicating via e-mail, Slack, Notion, various other async tools, write stuff down. Write down what the expectations are. Write down what the product roadmap looks like. Write down the user journey. Write down what you expect and what the deliverables are. And, you know, politics end up usually being a reflection of some form of emotion, some form of fear, trying to look good or look bad. And it doesn’t mean it goes away if you resort to written communication, but you just have fewer elements of personal dynamics if you’re operating in more of an async way.

Henry Suryawirawan: Yeah, when you mentioned about emotion, I think also leaders need to think about now the psychology of human right. It’s not like you’re putting structures, you know, you just put people in a hierarchies or something like that and it all will work. Don’t forget about the human aspect, the psychology, the fear, the emotions that got involved in all this as well.

[00:40:30] Key Practice: Learning & Development

Henry Suryawirawan: So maybe let’s move on to the next key practice, which is learning and development. Because I’m sure in a high growth organization, sometimes people crave, okay, what can I do to upskill my skillset? And you also mentioned, for example, those early in their careers, right? Sometimes they don’t have enough guidance or maybe people who transition from IC to manager, how to become a good manager. So tell us about the typical problems and the plan for learning and development.

Andrew Bartlow: Yeah, well, well, you nailed it. Those are the most common situations where you have early career people that are hungry to learn. And you have people that are promoted, especially in the managerial roles that are often in over their heads. And what I’ve seen at most startups I’ve interacted with is that they don’t do too little around learning and development. They do too much. They try to do everything. Like every time somebody asks for something, the answer is either, yes, let’s do it, great idea. Or great idea, go make it happen. There’s almost never a, oh, not yet, that doesn’t make sense for us. Or hey, that doesn’t align with our priorities. And I think that balance should probably shift. I think there really needs to be more prioritization as an organization around what learning and development initiatives you take on. So do fewer better.

And be clear about what those investments are around learning and development. Because this, it’s not always a ton of hard dollars. Like you’re not always buying expensive third party content or, you know, bringing in a consultant like me to go do something, it’s usually time. Like if you’re trying to develop your own manager skills training, like stop. Stop now and go buy it. You can buy it faster than you can build it. It’ll be better. And ultimately, it’ll be way cheaper, because you’re not burning weeks or months building a subpar product that you could get off the shelf tomorrow.

So be thoughtful about your investments around learning and development. Don’t get stuck saying yes too quickly. Like try to identify a few common core things. And in startups, like what are the common things? You’re hiring a bunch of people. So, so maybe, interview training or candidate selection. How do you do that? If you’re growing or maybe it’s customer onboarding or employee onboarding that you need to focus on.

Manager skills, we already mentioned that. But if you’re growing, chances are new people are coming into the org as managers or new people are being promoted into managerial roles. There’s probably something around manager skills that you wanna focus on. There may also be something around selling. Like, hey, if you’re hiring a bunch, maybe you found product market fit, and you just got a new round of funding, and now you need to go to sell this thing. So sales training or sales processes or the support systems around delivering to new customers. Those are probably a few core things that you’ll see pretty regularly. And there might be something unique to your org. Depending what you do or what you need, you may have something unique and that’s okay. But I’m suggesting that you don’t try to boil the ocean and say yes to everything. Say yes to a few and squash the rest.

And it’s okay to say no or not yet by focusing on delivering a few things really well. And as part of that, you’re deciding what you’re doing, and you’re deciding what you’ll do yourselves versus what you’ll buy or rent elsewhere. You know, so, so many startups seem to treat their people’s time as if it’s free. But time is money. Time is labor. Time is headcount dollars. Time from a team doing a lunch and learn or developing your own manager skills training, is time that could be spent doing other things that actually advance your product and your startup forward. So those are a few basics.

Henry Suryawirawan: Yeah, you mentioned about time. I was about to ask a follow up question, right? Because apart from just the content or maybe the instructor, the trainer, do versus buy, is actually to carve the time for people to actually put the time for them to learn and develop themselves. Because in a typical high growth organizations, there are too many things to do. There are so many things to get done. There are maybe a lot of focus and priorities at the same time. How can you actually motivate people to want to actually learn and develop themselves?

Andrew Bartlow: I think that’s actually rarely a problem. It’s rarely a problem that people don’t feel a high level of internal motivation to develop themselves. Again, a lot of people join startups to try to accelerate their career. As they’re passionate about the mission because they wanna move faster. They see the growth, they wanna be part of that. So I think there’s actually a pretty strong selection bias from applicants that want growth. So you don’t have a lot of that issue.

Where you do have an issue is where there might be some training or development that’s not obviously connected to something that benefits that individual. Like, hey, maybe you send everybody at the organization through some type of soft skills training that the engineers roll their eyes at. And the, the engineers say, how, how does that help me code in Python today. Like how does that help us advance our product roadmap? We’re like testing our confrontation and conflict skills. Like, I don’t get it. That’s where you might get resistance. And when you do get resistance like that, that’s a sign not necessarily that your team is wrong and they need to be motivated. But that maybe your choices about what you’ve prioritized for learning and development might not be naturally fitting every group with the same level of fit.

Henry Suryawirawan: Thanks for that advice. I think we all can learn about learning and development much better because I’m sure a lot of people wants to learn and upskill themselves. At the same time, also finding the relevant content for them.

[00:46:22] Key Practice: Culture, Engagement, & Communications

Henry Suryawirawan: So let’s move on maybe to the third key practice that I want to also learn from you, which is this bucket you mentioned: culture, engagement and communications. So yeah, what are the typical problems and what are the plans that we need to think about in this area?

Andrew Bartlow: With a high growth startup, usually the biggest problem in culture is the founders and the old guard holding onto the past. It’s resistance to evolution. And boy, evolution can happen fast. And if you don’t watch it, it can turn into revolution. But there, there can often be this, this feeling of anxiety or fear or loss of this tight-knit group of people that made something happen. And we went out and got funding and we built this product and we did this thing. And now, oh, now everybody, now everything’s all corporate. And ah, I don’t wanna be, you know, some big, bureaucratic tech company.

So usually the biggest problem around culture is resistance from leadership for the changes that have to happen. And, you know, so it’s important to know that culture will change whether you like it or not. So as you grow and add headcount, you can choose not to bring in managers. You can choose not to have layers, not to have structure, not to have role clarity, but people will figure it out for themselves, and it probably won’t be as effective as you want it to be. It’ll probably be a real mess. So you can fight it or you can own it. And so that’s the plan. The plan is make some decisions about how you wanna operate.

And share those decisions. Like you could share those in a vision, mission, values statement. You could share those in some operating principles. You could share that in a RACI type of decision matrix. But sharing is important, right? As you grow and scale, being able to communicate with this bigger org that doesn’t have the same depth of history with you as a founder, as your early hires do, they don’t necessarily think the same way that you do, or have all the same ideas and learnings that you’ve gone through and building your company.

So it’s about communication. It’s about trying to get those instincts that are in your head as a founder out to a team that now might have dozens of people in many locations all spread out that might not be working for a common vision unless you’re able to describe it effectively. So that’s the plan is communicate how you wanna operate. And, you know, again, it’s hardest for the old guard and the founders. You don’t need to have like a fake funeral ceremony. Um, I’ve kinda laughed about that. I think Oracle did that as they changed from one CEO to another at one point. They like buried the past. You don’t have to get, do anything like really silly and dramatic. But it’s okay. And actually, I’d strongly advise, be specific about what worked when, and what needs to change to be successful in the future.

So it doesn’t mean whatever you did or however you operated in the past was wrong or bad. That got you where you are now. But being clear about, hey, I as CEO founder can no longer have one-on-ones with every single person. I’d love to, but there just isn’t enough of me to go around and have me do all the things that I need to do. So instead we’re gonna do all hands on a weekly basis or a monthly basis, you know, that that’s a change.

Another example might be, hey, I know all of you would like to weigh in on the product and the design, and we used to all meet in one room and move the mouse around, or, you know, now it’s on video and do product demos every week. There’s just too many of us now. It’s too much time and not everybody touches it. And so the way that we need to operate is different and we’ll have the product team work on that and maybe they’ll do an office hours once a month for the people that wanna attend. So just being very specific like that about what things need to change and how people’s roles will change, can be really helpful in moving through a cultural transformation.

I think there’s also something around culture where so many startups are trying to do something new and different, right? I talk about like, don’t recreate the wheel. You’re maybe not as special as you think you are. You don’t have to make up everything new. But be clear about who you are. As we think about culture, I see some startups just try to be everything to everyone. And, hey, we wanna be completely flexible and we wanna pay everybody at the top end of the range. And we wanna only, you know, have the best desk chairs and only the coolest programming language and we wanna do all the stuff. And, you know, ultimately, in terms of operations and culture, it’s healthy and necessary to make some choices about who you are, what you’ll prioritize and how you’ll operate. And so that comes down to figuring out as a founder, as a leader, how you operate and ensuring that the group understands that.

And maybe you need to evolve over time, and that’s okay. And you’ll change your messages and you’ll change your expectations over time. But communications at the core of all of that. Like make it clear how you want your group to make decisions and that will make it easier for you to allow them to make decisions. You can’t empower someone unless you trust them, and you can’t trust them unless they make decisions that are similar to you. And how can they do that unless you explain how you make decisions and how you prioritize things. So yeah, I know I’m belaboring the point, but this is often one of the, you know, harder emotional things for a founder CEO to move through the challenges of growth are really largely around culture.

Henry Suryawirawan: Yeah. So you mentioned about vision mission. Be clear who you are. I think the company values as well, right? Those things that stay true as the company evolve. I think that’s also important to make clear, right?

[00:52:17] Sensing Employees Engagement

Henry Suryawirawan: And also I think the other point is about engagement, right? How do you actually first get the pulse of the employees engagement? Because as you grow large, maybe you cannot track everyone’s engagement for sure. How can you maybe understand what is the sense of engagement for my employees? How can we boost the engagement and things like that? Maybe some, you know, short tips and tricks here as well.

Andrew Bartlow: This is actually a favorite topic of mine. I’m a founder myself. I’m building a B2B SaaS product that will do performance management and employee pulse surveys. I think it’s really valuable for organizations once you get so big that a founder can’t talk to everybody and know what everybody’s working on and how they feel to have some method to gather that information.

So, you know, lots of organizations like Lattice or Culture Amp or 15Five have a survey tool that you can do engagement surveys. That’s okay, but it’s really long cycle. It’s really expensive and you can’t do it more than twice a year. And you ask a thousand que, or not a thousand, you ask a lot of questions. You do action planning for month and what actually comes out of it? Not a lot. And then you have these big performance management systems, you know, some that I just named, that are intended to help people figure out what they should be working on and how they’re doing. But it’s just all overbuilt.

And so I really think that the best method to stay in touch and stay in tune with your team is to talk to them. Like the most powerful tool is a one-on-one and a skip level. And the best thing that you can do when you have multiple layers is a skip level every once in a while or an all hands. Like just talk to your team. You know, call it a focus group if you want.

Inspecting what you expect out of one-on-ones is kind of the missing piece for a lot of organizations. Like are your managers actually…, actually having useful conversations with the people that work for them? What are they talking about in those one-on-ones? Is it just like reporting the news and doing some light bonding? Or are you actually helping each other and providing feedback about “you’re working on the wrong thing, I need you to focus on this other thing right now”. So I think there’s a real opportunity to enhance the focus on one-on-ones to inspect what you expect out of your middle managers. And there’s some simple tools that you can do it. And I found myself trying to build it in Google Forms and it wouldn’t do all the segmentation I wanted, and now I’ve gone down a rabbit hole of building the SaaS product.

Henry Suryawirawan: I really love the, you know, simplicity that you emphasize, right? Just talk to the people. You don’t always need to build fancy surveys or buy all these expensive tools. And in fact, yeah, after we collect all those surveys, right, coming up with some action plans itself can be really, really difficult. Especially coming to come up with, you know, maybe top three or top five things that the company needs to do, right? And I think I like what you mentioned about you inspect what you expect, right? Because sometimes, yeah, it’s not clear what we expect. And maybe people are also not doing it as what you expect as well.

[00:55:14] 3 Tech Lead Wisdom

Henry Suryawirawan: So thank you so much for this time, Andrew. I really love our conversation. I think in your book you have more tips, more plans, more basics that leaders can learn. And also when they go through all the stages, right, it will be different kind of context that they need to take care about.

Before we wrap up, I have one last question that I want to ask you. Typically, I call this three technical leadership wisdom, but I think your background is people, so I guess I can call it three people leadership wisdom. So think about it, just like an advice that you wanna give to us for us to learn from.

Andrew Bartlow: Oh wow. Big, broad area. And we’ve already talked about so much good stuff already. Yeah, how, how do I boil it down as concisely as possible. Let’s start with be clear. That’s a people leadership wisdom item number one. Be clear. Be clear with your team, with your organization, with people that work with you. About your expectations, about your goals, about your priorities. Don’t avoid the hard conversations. Be clear. Don’t leave it up to them guessing. Communication is just so important.

I think another area and maybe this is obvious, but also no matter how big you get, stay human. Continue to show some human empathy. You know, I’ve worked in organizations with hundreds of thousands of people, you know, General Electric and Wells Fargo and Pepsi, hundreds of thousands of employees. And it can be easy to start to think about people like numbers at some point. And you know, if you’re a founder with a team of five, you’re in no danger of that right now. But as you start to scale and add some layers, and you start to think about these management processes, stay human. And show some empathy to people, because, you know, no telling what somebody else is dealing with. And being empathetic can create a lifelong commitment and relationship.

And maybe a last one would be keep it simple. There’s a lot that needs to be done at a startup. There’s a lot that you can do. But if you’re able to focus and prioritize and just do the basics really well, it’ll take you really far. So, you know, usually, the challenge is trying to do too much too soon. So keep it simple for as long as you can.

Henry Suryawirawan: Oh, I really love the simplicity of your wisdom, right? Be clear, stay human, and keep it simple. I think it’s always good to have this simplicity kind of wisdom so that it really relates to all of us.

So Andrew, if people love this conversation, they wanna learn more from your resources, you know, book or, you know, online materials, is there a place where they can find you online?

Andrew Bartlow: Yeah. Thank you. I am all over LinkedIn. Look for me on LinkedIn, Andrew Bartlow. I’d love to offer your listeners a code to get a free download on my website as well. The main website that I am on is peopleleaderaccelerator.com. People Leader Accelerator. And there’s a section where I have a bunch of guides that are available for download. Many of them free, some for a fee. But if you use the code “podcast”, you can download anything there for free. So you know, hopefully some of your listeners take advantage of that.

Henry Suryawirawan: Thank you for the generosity, so I’ll make sure to put it in the show notes as well. So again, thank you for your time Andrew. Really love our conversation. I think people management is something that most of the co-founders will need to learn, right? Sooner than later. So thank you so much for your sharing today.

Andrew Bartlow: Thanks for having me. I really appreciate it.

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