How to Build and Scale High-Performing Teams

Aydin Mirzaee  2:10 

David, welcome to the show. 

David Sakamoto  2:13  

Thank you so much. I really appreciate you having me. I’m excited for the conversation.

Aydin Mirzaee   2:20  

This should be really fun. I’m particularly excited to interview you, because you’ve had so much expertise in leading Customer Success teams, but also because you work at a very interesting company that is one of the largest companies in the world that is fully remote.

There’s a lot that I want to get through today but I guess what I wanted to start with first was to ask you throughout your career Who has been the manager or leader that you’ve enjoyed reporting to the most and what  made you like that person or what did they do that was special?

David Sakamoto  3:00  

That’s great. I certainly have had multiple times where I work with great leaders, even I would say my current role Michael McBride, I would certainly say is among the top, wicked, sharp, very thoughtful caring about his team. I won’t go down that path. It’ll sound a little too self serving. 

But there’s a couple, to extra give you a couple examples. One is my first manager out of college, Mike Doosan. And he left a mark on me and one thing he would say is “look, my job is to get you where you want to go”. And he was very clear, “whether it’s on my team, or whether in our department, or in the company or in another company. I want to make sure that I’m supporting your career goals and getting you where you need to be”. And that was very meaningful for me because, you know, it was crazy times back in mid 90s at Silicon Graphics, things were moving really quick, working a lot of hours, and he would put on the agenda and force every month we’re gonna have a career conversation, and would ensure that that didn’t get lost. And it gave me, as someone on his team, a lot of faith that he was there. He’s got my back, and he was thinking of my best interest. So that was very meaningful. 

There’s another leader that I worked within his organization, and he also had a quote or something that’s resonated with me and he said, kind of loosely quoting him but the Esper Anderson, and he said “your projects, your programs are going to come and go, the legacy you build will be your teams”. And to me some of those concepts or some of that building blocks of servant leadership, even before that word became something that became native to my language. And there’s a couple moments where they had no gets free kind of, I think everybody in their career is going to work with great leaders and picking those up and making those part of your management style are really important.

Aydin Mirzaee   5:04  

Interesting. I’d love to dig in on both of those things. So he specifically every month even through all the madness of all the growth that I think you said Silicon Graphics, he made sure that you always had a career conversation as part of like the many one-on-ones that you would do?

David Sakamoto  5:23  

Yeah, so he had carved out and he’d have his folder, pull it out with all his notes. And I can’t remember exactly the cadence, I thought it was around once a month. But whether it’s once a month or every six weeks, or once a quarter seems a little long, but it didn’t have to be everything. But just like skills development or areas of interest or programs that would be assigned to. So it was very thoughtful to make sure that development-related conversation was helpful in terms of feedback or opportunities where I could test these skills and we talked about those. So it was really, really important. 

I found it stressful and a lot of times when I, in the middle of things as a team member, I got all these other things I got to be working on. But looking back, I realized how important and valuable that was. And then also the message that it sent to me, which was the most important thing around “I’m thinking about your long term future. And I’m here, I’m gonna invest the time and I’m making sure that I’m supporting that growth”.

Aydin Mirzaee   6:26  

Yeah, that’s super interesting  On the other note, on this concept of building teams and having those teams be your legacy, What did he specifically mean by that? 

And the reason I asked is, you know, in fast growing companies teams change all the time, people move all across. Did he actually mean the specific teams and the members of the teams that you brought into the organization or was it more from the deliverables that those teams actually achieved? 

David Sakamoto  7:00  

No, it was very much around the teams. And it’s definitely resonated to me. So everybody in the heat of the moment “I’ve got this project that’s got to get out, or we’ve got to close this deal or we’ve got to, you know, work through this customer issue”. There’s always something and those things are truly important.  But as you look back in your life, I don’t remember all of them. I don’t remember what was project Cheetah or this or that. 

But I definitely remember the teams we put, the teams that built. Or maybe somebody that was struggling and was able to partner with she or he to help develop their skills and get over it. Or maybe you worked on a development plan. And that person not only got promoted but has moved into a trajectory where they’ve continued to move up and become a leader or moving to roles that they wanted to. So, I personally can relate to it. And the things that I’m most proud of are the individuals I helped develop, or the teams that we pulled together and what we together did as a team. 

I can’t honestly remember what we did. But I remember how we did it. That the teamwork and the collaboration, and supporting each other in the transparency in the direct feedback. To me, ultimately in a day, it’s those experiences of developing individuals or developing teams, and to some extent to how we did it, versus necessarily what we did. And I’m not saying that those things aren’t important. They absolutely are. That’s why we’re focusing on them. But I just as a human being when you look back and I think of when I want to look back at my career, I’m going to be thinking about the people and teams. 

Aydin Mirzaee   8:50  

Got it. So speaking of teams, you’re obviously very passionate about building teams and one of the things that you’ve often talked about is building teams that can scale and the concept of building scalability into teams. I’m curious, How do you define scalability? But also what is your playbook? Like what tips and tricks do you have for people to build teams for scale?

David Sakamoto  9:18   

I mean, ultimately, I think it’s the ability to provide more output and bring more people on. So scalability ultimately is around handling a higher level of output or higher level of business or more team members. And interestingly enough, my past two roles at GitLaB and at Cisco both had to do with really rapid scaling. 

So here at GitLab, I started when there were about 40 people. We’re now about 120. So a little less than a hundred people and it’s just quite literally the same thing. We hired 100 people, but I would say the hiring is really just that practical measure that people can relate to. When I think about scaling, I often describe it as the platform, in my role, customer success platform. But I think it applies to any role that you’re building a team, building out that platform. And when I think of what that platform is, it’s that combination between the people, the processes, and the systems. And I always start with the people, because in any business I think it ultimately starts with your people, whether they’re direct or indirect to working with customers. It’s all of the things you have to do around people managing, people development. 

Do you have skill sets? Do you have levels to the career path really plainly identified? Do you have enablement to ensure that when you bring people on, you can support them and provide an ongoing learning experience? Do you have the right processes built in? Actually are you supporting people’s performance and career development? There’s a ton of other things I haven’t listed, but really ultimately ensuring your team can be successful. Again, going back to that servant leadership, I view my job as making sure that I provide an environment for my team to succeed. 

As the second part of that: the process, right? This is how you do your job. This is how you work together. Some of the HR stuff I talked about around feedback and career development. How do you shift constantly looking at the business and looking at first being effective, then being efficient, and you ultimately have the right processes and operations and metrics to ensure that your team can be successful individually as a team, as a as a company in terms of organizing and collaborating together, and also for your customers and partners. 

Really in the last piece is on your systems. And that’s also on purpose last, right? Your systems are there to support your people and support your processes, not the other way around. I was in a recent panel and they said “hey, how do you integrate systems into your scale or  in your business nicely?”. Well, first I think about the people then I think about the process, then I think about the systems that are ultimately needed to support both of them. At the end of the day, all of that: the people, the processes and systems, you’re there to ultimately drive results for your customers, for your team members, and as well as for your investors, whether you’re in a privately held or in the public market, I think of those three constituencies in all situations.

Aydin Mirzaee   12:30  

That’s really interesting. So it’s almost like you’re thinking about the teams, you’re thinking about how do you bring someone on board? How do you get them to ramp up in as little time as possible? How do you continue to support their development? What beyond that  are you also thinking about like in very tactical terms?

David Sakamoto  12:57  

Invery tactical terms, there’s a ton of areas where you can focus on in terms of money, you certainly want to bring them on board. If I think about the lifecycle of a new team member, right? 

First, you know, the recruiting aspect is very important to make sure they have the right fit, the right experience, right values, you’re going to onboard them, right? So you have the right enablement plan for them. But also, do you have the right continuous learning? I know, in all of my jobs, there is learning about the product, learning about your customers and partners learning about the internal process and operation. So it’s not a one and done, that’s a continuous piece. 

As they come on, beyond I won’t go into the process systems piece, assuming you have the right environment for them to be successful. You also need to make sure that you’re continuing to develop them. So do you have it? Do you have the right set of here’s the progression of your career, and you’ve got the right set of processes to support both the tactical “just checking in how are you doing”  to the development conversation, the performance conversations. And ultimately, you know, I think the three premises that excite people, like people think of conv. I think generally, from an employee satisfaction and excitement of their role. Are they excited about the business? Do they have a career opportunity ahead of them? And do they have a good relationship with their manager? And of the three, two have very direct-full of a responsibility and accountability on the manager to drive that. Obviously, the company’s a bigger scope. But ultimately, I think of it that way. To make it a successful customer engagement, I need a successful team engagement and successful team members. 

Aydin Mirzaee   14:49  

That makes sense. And I think that ties in well with another topic that you’ve talked a lot about, which is building scaling strategies and making sure that those scale strategies are never unclear. And you’ve actually built a framework around this. I would love for you to tell our listeners a little bit about the framework and some of the nuances.

David Sakamoto  15:15  

I think you refer to a presentation it gave back at a conference. But I wouldn’t say it’s any rocket science. In fact, I did get my disclaimer in terms of super manager, I don’t consider myself a super manager. When we talked about development, I think most of my learning experiences came from mistakes I’ve made in the past but I care and so just constantly looking at how you’re doing. 

But it relates to the strategy. I think it’s a couple different premises. Number one it’s based on as a leader, even depending on where you are as a leader.  Your role is to develop a strategy, brea it down into execution priorities. Help facilitate the team in order to go execute those. Assess how you’re doing. Review, rather rinse repeat. So whether you’re a Chief Customer Officer, whether you’re a VP of success, whether you’re a manager, all of those same components apply to your job. What are the things that you need to do to ensure you’re driving strategically to ensure success? How do you break that down? I think of time and strategy as just a longer term plan. How do I break that down into say one year strategy or 18 months? How do we break it down in what needs to happen this quarter? And you can use a lot of different metrics. I use VSM, which is vision, strategy, execution metrics at Cisco, and at GitLab we use OKRs. 

So like, what is the framework that you want to build to say “Okay, I’ve got 12-18 strategies that I’m able to articulate. I’ve written that down. I’ve communicated, I’ve had conversations”. Number one: make sure that is well understood. Then usually whatever framework you have or something other than VSM or OKRs, How do you break that down and chunk that up in terms of quarterly priorities? How do you kind of divide that up among the team? And what’s your operational motion to define those goals? 

Then you probably have some cadence. You have weekly team meetings, how do you work into that? Just checking in making sure servant leadership, your team has the support they need to succeed. You probably even have a monthly check-in. Are we progressing as we expect? And you close out the quarter, How do we do? And really that’s that iteration a big part of my personal management style and in GitLab one of our core values is iterating. How do we look? You may change your plans and goals “Hey, I thought this was queued up for q2” for example. Well, based on what you learn, you adjust. Leverage that communication, empowerment, autonomy, leverage that the skills and experience of your team, make that adjustment great. 

And then rather, rinse, repeat. So I think it’s really around defining that strategy. Having a framework to break that down into execution, building that operational cadence, whether it’s staff meetings, one-on-ones, monthly check-ins, QBRs, drive and track that for both progress in feedback and in iterating on what those goals are.

Aydin Mirzaee   18:17  

And in your opinion, what are some of the pitfalls? Like what are some of the traps that you know people do when  coming up with this strategy, breaking it down into components that you kind of talked about? 

One of the things that comes to mind for me as an example is oftentimes, I’ve certainly worked at organizations where there’s been these high level goals that say the company has come up with and there’s almost too much forcefulness of trying to make sure that every single person’s roles and everything they do fully leads into this main goal and it may or may not really be a perfect puzzle fit and that’s one thing that comes to mind. But you’ve obviously seen this at a lot of companies. What are some things that make this hard to do?

David Sakamoto  19:08  

I think probably the biggest challenge that I see and I still live it every day is balancing the time you spend on strategy and this time do you spend on tactical even firefighting. How do you constantly do it? Because asI lay out those goals, even when I pick the top two: run the business and built for the future, those are now supporting you at least in what can be interpreted as the exact same thing of what you how you prioritize and where do you spend your time on, on a day to day basis? 

I think the crux ultimately is How do you drive the right balance? You’re not being too tactical, but you’re not this 10,000 foot pie in the sky. It’s really balancing the both and if someone asked me what percentage should be on strategy and that’s not a question that I can answer because if you’re given a certain stage, you’re gonna be focusing a lot more strategy, right? So plan a lot more on annual planning so that if I’m spending a lot more time on strategy then I would say in middle of q2, q3. But I think the important pieces that you build your framework, and as your leader, you’re making sure you’re stepping back. And I think it’s all over those cadences whether it’s annually, quarterly, monthly, even weekly. I use Sunday nights to kind of like just see every Monday morning What do I need to accomplish this week? and looking at last week, looking at board week… Make sure you operationalize a lot of these, you’re constantly just kind of checking yourself and making sure that you are balanced out across those different things. 

And it’s really challenging. I think there’s a piece of building a framework, and operations. There’s a lot around just experience and listening to the business and seeing how things are performing right now. I look back even just a little less than a year journey that I look back “Oh, I wish I would have done that differently.” And it’s about having no ego around what you did, right and what you did wrong. It is mostly about how do you learn and try to implement that Kaizen attitude around. I’m not going to worry too much, I make mistakes, we all make mistakes, what can I learn from them? Great. How do I make sure I’m applying those learnings for the future?

Aydin Mirzaee   21:22  

You mentioned something interesting, which is, it sounds like on Sunday nights you have a ritual that kind of looks at the week ahead and making sure that things kind of balance. 

I would love to just get into some of that in terms of how do you plan your time.  Do you have, for example, certain rituals around I should be spending X percent of my time in different types of buckets or how do you make those considerations?  Also, do you teach those sorts of things to your team as well? Or is it just you? Is it just something that someone has to just develop on a personal basis, are there best practices that you’ve come to realize?

David Sakamoto  22:06  

Great question. I would say just pick a week level. I always like to start my week clean. I like to catch up. I like to be caught up. I don’t like to come in the week already feeling like I’m behind. So whenever I felt like I needed to accomplish the prior week, I like to clean it up or kind of assess like “Hey, I wasn’t realistic, and I need to work better this week”. But I like to start my weeks clean. So it’s partly around what I wanted to accomplish last week and partly around looking at what I want to accomplish this week. I like to have a look through my calendar and make sure that I thought through that. Am I set up for success in terms of that week,? and if I put in the right work efforts, and I also try to weave in “I need to like scheduled time. I need to work on this thing”. If I don’t see that on my schedule, I’m probably not gonna get work done. 

So it’s a matter of kind of planning out your week. I do follow a specific structure as well. So I try to and again, we all know our lives that things are pretty dynamic. I like to front in all my one-on -ones. So like Monday would be my time for checking in with the team. I generally try to align my one-on-ones and on that first day. But people’s schedules, their dynamic doesn’t always work that way. But that’s where concentration is. Day two, I like to lead for Team stuff. So there’s an overall leadership team, there’s other functional meetings, I line those up and then we have our zero meeting and other other meetings but my group meetings on Tuesday. Generally Wednesday, Thursday are working. There’s all kinds of stuff woven in. We all see our counters, and then I try to do my best to preserve Friday as around more working time there to make sure that I can catch up and get things done. And, again, that kind of is my goal to finish clean for the week, so that when I roll around Sunday I can kind of reset my cycle. 

And again, I think management’s all about their cycles, right? You have a weekly cycle, you probably have a monthly or we have a quarterly and you probably even have an annual set of cycles. So that would be my advice for any leader around: figure out what those cadences are across those different durations. 

Aydin Mirzaee   24:30  

Yeah, that’s super helpful. I feel like I’m gonna go back in and retune the way that I schedule some of this stuff. 

Shifting gears for just a second. One of the things that is very interesting is you basically have this principle where you typically don’t voice your opinion or you may try not to do that until you’ve heard other people on your team or within a group or meeting set. And I know that this is particularly, I mean the culture of meetings and the way some of these behave could be different at an all remote company. So I wanted to just hear your thoughts on Why do you let everybody else speak first? Is that even more important at a remote first company or is it principle applies everywhere? Or how do you think about that?

David Sakamoto  25:29  

I think the interesting thing is with the way that GitLab operates, and I’ll suggest anybody listening to look at the handbook. Every single thing that we do is documented and totally transparent, like how we run our entire business is totally available to the public. But I would say that ‘don’t speak your opinion first’ is really a small minor tactical method I’ve tried to use to really promote servant leadership and empowerment and autonomy. Again, like most of my management, I think I’ve shaved many from mistakes I’ve made. Looking back and my own personality, I bring a lot of energy and excitement and so  I always want to throw my opinion in. Like okay I’ve got a great idea and I like to debate. I like to get in and people have put opinions. 

But I’ve realized people process in different ways. Not everybody has my approach or they want to get in, debate and work through the issue. Not everybody thinks that way, not everyone processes that way. As their manager, I can stifle the whole conversation. So if there’s like a What do you think we should do? And then first thing the manager says “I think we should do this. Now. What do you think?” Well, that kind of shuts down the conversation. I think the best option is “What does everyone else think?”. My suggestion is like don’t voice your opinions until everybody else has. It’s been something that with my own understanding of myself as a leader, I’ve thought through it and said “Hey, I want to make sure that I don’t stifle the conversation”

You stifle the conversation, you’re stifling ideas. One advice to managers: if you think you’re always the smart one, you’re always at the best ideas, I will tell you now: you’re delusional. And that’s why you bring on teams, you’re gonna have a different approach and a different way to think about things. So try to do your best to harness those conversations, make sure he has a voice. And be thoughtful around the fact that  people are going to process and engage these conversations in different ways. Make sure the agenda is ready  in advance. Some people don’t want to just think on the fly. Some people want to think about it in advance and process it, maybe get some data. Try to set the expectation up front. What’s the decision that we need to make and then in the meeting you regulate and monitor: does everybody had a chance to chime in? If not, maybe you can probe them and ask them if they have an opinion or maybe check with them after. I always prefer before, because once a decision is made, it is made, but oftentimes that’s really a conversation around “Hey, the next time how can we set this up for you and contribute?”

I think it’s about being thoughtful of your position in the team, being thoughtful of the personalities and how she/he likes to engage in those conversations, and really doing your best to facilitate the conversation and bring out the best of people’s experiences, their passions, their uniquenesses and to me that’s the most exciting. Kind of going back to the thing around the legacy builder of your teams, to me I find that very enriching. To see and I love that especially when you’re like “wow, that is fantastic I never even thought about that”. Totally different rate, and the absolute best way to go for. So it’s when you experience those, then it becomes very real. And you’re like, Okay, this is why we do this right?

Aydin Mirzaee   29:07  

That makes a lot of sense. So I like this idea of different people process things, different ways. And also, it may not be easy for people to just think of answers to things on the fly. I know certainly  I’ve gone to meetings, and something’s been talked about. And at the moment, I’m not thinking of anything useful to contribute. But then the next day, I realize this thing that is highly, highly relevant. But obviously, if I had it before that I would have thought of it. So is your best practice. 

How do you folks handle this at GitLab? Is it agenda-like, is there an unsaid rule that agendas go out? Say like an hour before, is there a particular protocol that is followed or the night before? How’s that handled?

David Sakamoto  29:53  

It’s a great suggestion. You’d asked a little bit earlier about whether remote or not. I wouldn’t say it’s necessarily because they’re remote, but I would say it’s GitLab’s values in how we operationalize. So kind of a structure, which I, one of the things I love about GitLab is just as core values of efficiency. And everybody, every contributor, well it isn’t a value per say but the theme and everyone can contribute. So we use Google docs for all of our meetings, they’re all open. Team members can add in their own agenda items, and are recommended to do so. So team meetings for the team, not just like manager come down and I shall give you my commands for this week are priorities for the quarter. So it’s really a meeting for the team. 

So I’d say first and foremost, it’s open to everybody to contribute and design to what the agenda items are, and what we want to talk through. That’s number one. Number two, we always do agendas in advance. Sometimes, as I think about things of the week, I’ll just start putting them in, whether it’s a one-on-one doc or team meeting, to start putting those 10 items and as everybody can. By the way this is a great conversation. Like maybe we’re on Thursday, the week before. “Hey, let’s add that to the agenda talk about next week” So it builds over time. I’m sure we have something in the handbook. I try to do a minimum date/night before, but preferably it’s 24 hours before, but sometimes you’re looking at the agenda and think “Oh, hey, I’m gonna think through things”. So, again, we’re not perfect. But ideally, it’d be the day before  to take a look at it.

Aydin Mirzaee   31:30  

I would be remiss if I didn’t ask you about one thing that was specifically tied to customer success. Given that you’ve run the customer success team, my question is, What are some things that you have found strictly from a hiring perspective, that have been good indicators of people being successful in the customer success role/org and you know, whether that’s on an individual basis or on a manager basis, are there particular things that you found that you can do to kind of increase your odds of hiring successfully there?

David Sakamoto  32:09  

It’s a big challenge for the market. So if you think of customer success, there are people out there but generally it’s unlike sales function or something else like you don’t see a whole pool of people. I have been doing sales, customers success for 20 years or 10 years or 15 years. So oftentimes, you have to be very thoughtful around the skill sets, because I think what a customer success manager is and you need a perspective of sales. I need a service person, I need an oxy person, I need someone that has domain or product expertise or technology expertise. So you kind of start to put that all together as a hiring profile. You basically design a unicorn.  

I think you have to be thoughtful around what the expectations are for the cross of those skills sets are. What I generally say is you need strengths and two of them. So you look at the individual, but as also as you are hiring you look at the team. And I got a lot of people from services and product, I don’t have people even blending in someone from sales. There’s a little bit different mindset experience into the team. So I think  you have to look at the individual, you have to look at the team. But I think the one common thing to your question, I look for a passion for customers. Very specifically, can you tell me about a time where you put a customer’s needs in front of yourself? Or tell me about how you had to drive internally to get support for a customer need or for a customer initiative? 

And I look for people that can show specific examples of putting the customer first. I look at how they tell you that story. Are they excited? Sometimes you get these people, they’re talking other stuff when you ask a customer, they just turn on. And so I look for a bit around someone who can demonstrate those experiences, but also someone that really just has that passion, right? That you can see they care enough to be energetic, passionate, and also care and empathy. It’s that caring, empathy, passion for customers, is that kind of underlying trait that you look for across the board. 

Aydin Mirzaee   34:32  

Cool. I mean, that is great advice. And yeah, it’s those things that when you see someone’s face light up while they’re talking about something, that that’s certainly a great thing to look out for. 

I think that we’re coming up against our time so the the final question that I wanted to ask David was just around any final tips or advice that you would have for managers looking to get better at their craft, get better at leadership, any books or resources or blogs, or anything like that, that you would leave the audience with?

David Sakamoto  35:09  

Yeah, I think especially new managers, you don’t need to be perfect, right? So if you think about the things that are important to managers, running the business, developing your team, building the business, I think one suggestion would be: don’t expect perfection, you’re going to make a mistake, your team understands you are going to make a mistake. But what’s more important, just like how you’re going to guide your team, is learning from that and being transparent about that and checking your ego at the door because that will also set the tone for you. You’re basically role modeling how you want the team to work together. So that would be the first.

In terms of resources, there’s a couple books like they’re probably not the traditional management books, but a little bit related to me personally where I’m in a high growth. The Hard Thing About Hard Things by Ben Horowitz. One of the key things I like is as your company scales and specifically for GitLab and other fast growing businesses, you constantly have to be looking at what is your role in this organization? How does that evolve as the organization changes? and that was one of my key takeaways from that book is constantly looking around your role and what is the business need? What do your customers need? What is your key need as you scale and grow? The other one is Never Split the Difference by Chris boss. That’s about negotiation, and it’s just one of those things that I think if you think of core skills, like listening, negotiation is one of those core skills that I’m constantly working out to be a better listener. And one thing I think also is that core skill says negotiation like how do you negotiate in for the title never split the difference.. You’re not just splitting the difference, but you can find a true win-win. 

Aydin Mirzaee   36:54  

That makes a lot of sense. When you first set it out, I was thinking negotiation, i mean, sure it’s important, but the way that you described it, which is to listen and look for commonalities, that’s probably a really, and I can see when you’re talking to even customers and like they want something and you want something, you may want the same thing. But you don’t know unless you ask and dive deeper.

David Sakamoto  37:19  

Yeah, there is bunch of skills like discovery of needs, and articulating that in the right way that appeals to what they’re looking for. So this great bunch of great information there.

Aydin Mirzaee   37:30  

And we’ll obviously include both of those in the show notes. But yeah, David, thank you so much. This has been super helpful. Thank you for being on the show.

David Sakamoto  37:40  

Thank you so much. I really appreciate the opportunity and hopefully have some helpful tidbits in the podcast. So thank you again for the opportunity.