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Interview with Libor Michalek, President, Technology at Affirm, Inc

Location: San Francisco Bay Area

Vidal: Libor, hi, thank you so much for taking the time to speak with me today. Maybe you could introduce yourself, say a little bit about where you’re located, and what’s your current role.

LIBOR: My name is Libor Michalek and I’m the President of Technology at Affirm. I run our engineering, product, operations, and people teams.

What’s your background and how did you get into management?

Vidal: All right. I was looking at your background. I know you worked at Google, YouTube and different places like that before. Can you maybe tell me a little bit about your background and how you got into management and engineering leadership?

LIBOR: Certainly. So a lot of it actually came out of necessity. I went to school at University of Illinois, got a computer science engineering degree there then went straight into writing software. Pretty quickly, I moved into helping as an engineer, early engineer or first engineer building a variety of startups, in a variety of spaces. I was always very excited about software as something that enables a new business and new idea to come to fruition across really a variety of domains.

LIBOR: The first startup I worked on was in enterprise software followed by consumer web, and data center networking hardware. Then back to consumer web with a foray into social. At YouTube, I ran the infrastructure engineering teams. And, finally, into Affirm, which is solving financial technology problems and building products in the financial space.

LIBOR: I was always really excited about building and solving problems that were interesting and having the software background, that was the avenue for how to solve those types of challenges. In fact, one of the criteria for each one of the things that I worked on was always that software and technology had to play a vital strategic role in solving those problems.

LIBOR: The transition into leadership and management was something that happened for me multiple times, not just once. In each of these organizations with no real management in place or required given the size and scale, I’d go in, roll up my sleeves and write software. Then, as the organization grew, I would ultimately take on a technical leadership position, then a management position. And as the companies grew, I’d move into senior management positions.

LIBOR: I was fortunate to have the opportunity to go from individual contributor to tech lead, to manager, to manager of managers, director and vice president. Not only going through the journey multiple times but also taking lessons and applying them to the next opportunity. I feel like that was ultimately a really edifying experience, going through it and being able to f replay the past experience and apply those lessons to the next time through.

What’s your advice for managers who are just starting out?

Vidal: Well, so that’s great. So for you, it’s been a natural evolution to go from one stage to another to another. I’ll skip ahead to a question I like to ask. Maybe you could say a little bit like what would be your advice, then, for people who are just starting out as managers? Or may be going from level to the next since you had that experience multiple times?

LIBOR: Well, I’m always a little hesitant to give advice without context of who’s receiving it and what they’re taking away. Because it is very contextual. And context is extremely important in terms of not just giving advice, but also taking advice.

Vidal: Okay. Fair enough.

LIBOR: What I would say, that I think has been pretty applicable across each level is each time you move to the next stage in that progression of leadership, you’re playing a dual role. For example, as soon as you make the step, from tech lead to manager you’re checking your fidelity of understanding by really playing both roles. Right? We see this a lot when a really strong tech lead moves into management, they will continue to lead engineers on the technical side as well as on the people side.

LIBOR: And that really enables them to have this really perfect understanding of the relationship between a manager and a tech lead because they’re doing both. And so when you have that opportunity, you should really make a conscious effort to recognize which role you are playing when you’re playing multiple roles. Really seek to understand the relationship between them. Because ultimately, that will enable you to be able to manage tech leads when you’re not in that role as you continue to scale.

LIBOR: And it’s applicable at every level as you move from manager of ICs to manager of managers, similar things happen. You’re in a dual role and straddling the responsibilities of both. You have to do it very explicitly and be very conscious of it, I think this allows you to reflect on what it will be like to manage people who step into that role under you with a fresh perspective. So I think that’s probably the most broad version of advice I can give folks.

What are the biggest challenges you face?

Vidal: Great. Thanks. That’s very interesting. All right. Moving on. What would you say are some of the biggest challenges you face now as an engineering leader?

LIBOR: Communication. As you scale, people will take away different things when somebody gives a direction or provides context. When somebody helps to set direction. We always, all of us, take away a little bit of what, not just what is being said and what is being communicated, but what we want to hear, what we wish was being said. That can lead to discrepancies between what was intended and what was received.

LIBOR: As the organization scales, I think it becomes really important to, spend time on clarifying. Really getting to the heart of the matter. Getting crisp. And, then, iterating and reiterating. I think it always surprises folks that for any given number of people on the team, just how many times you have to make sure to reiterate a message to strengthen it and to make sure it lands.

LIBOR: You also have to get a lot of feedback from your teams and from the people that are receiving the message to really understand whether it was received. How you should change it for the next time. How you can improve it. How you can land it. And that becomes a challenge. That scale, that’s a real challenge because it really only allows you to have so many messages in flight at any given time. You have to be very, also diligent with what messages you are trying to communicate as well. That’s a challenge, I think.

What is your approach to hiring?

Vidal: That’s great. Communication is so important for leaders. So thanks for sharing that. Another key part of the role is, of course, hiring and recruiting talent. I wonder if you say a little bit about what your approach is to hiring. And maybe also speak a little about another thing that relates to hiring that people are interested in is maybe diversity. Do you have any thoughts on that as well?

LIBOR: So on hiring itself, I think the lessons are pretty consistent – in the end, you’re looking for talent. The questions are, where are you looking for talent? How are you thinking about sourcing and identifying talent? That is really important. Trying to get creative about how wide of a net you cast and then making sure that you have real clarity on how you’re identifying talent.

LIBOR: And with engineering, there’s obviously the technical aspects. For us, the technical aspects actually break down into three pillars: communication, collaboration and actual core technical skills. That’s because, at the end of the day, writing software is a team sport. And you have to have people who are able to clearly communicate their intent, their ideas. They have to be able to work together in a group. So it’s not just the core technical skills, but how you’re able to actually effectively deploy them in a broader setting.

LIBOR: And, then, there’s the cultural pieces. And I do think it’s very important to have clear culture guidelines, so you don’t have any misunderstandings about what it means for somebody to be a fit in the organization. Right? Too many times, culture can become sort of a catchall, which is very much about just somebody I want to work with. Is this somebody like me? And I think that the more effort you can put into defining culture in the context of your organization, and how do you think that actually maps to effective employees will have an impact on your business.

LIBOR: Getting really crystal on that, helps people understand what it is you’re looking for beyond just technical skills. It also frees you to having clarity on these are the things that are non-negotiable elements of what we’re looking for, especially when casting a wide net for talent. It opens you up to a world of possibilities of what does work.

Vidal: Could you say a little bit about, on culture, how do you evaluate or cast for culture or interview for culture?

LIBOR: Yeah. In our organization, we have very specific cultural hallmarks around humility, motivation towards self-improvement and the confidence to solve problems. Those kinds of aspects. And for those, we have very clear guidelines and questions of how we evaluate. Most of those are situational. So asking for different types of experiences when people ran into trouble, when they had to work with somebody that might have been more difficult or when they ran into problems.

LIBOR: A lot of times, what we think of as important hallmarks come through when people are in adverse situations when things aren’t going well. So we ask people to speak to those experiences and to understand how they approach them. And if they’re having trouble coming up with some, we’ll also put out some hypotheticals to get a sense for how they would handle them if they did turn up. And, then, using that to really dive into the different elements of: does this person score well on humility? Does this person score well on how they handle adversity? Those types of elements.

Vidal: Got it.

LIBOR: It’s very important that you try to make it as objective as possible and making sure you have criteria that are objective as well. We’re trying to pull the subjective ones out of it to the degree possible.

What’s your workday like and how do you manage your time, emails, etc.?

Vidal: Okay. I know you’ve managed a lot of people. And you’ve been a manager for a long time. One of the challenges a lot of managers have is just getting stuff done. Time management. I’d love to hear what are your strategies or what is your approach to managing your workday, emails, calendar, meetings, like all the stuff you have to do…

LIBOR: Well, that is definitely something that is ongoing. That never ends. New strategies, new ways. So I’ll ask people as well. Probably the biggest piece for me is also knowing yourself, getting comfortable with yourself and understanding what is a sustainable cadence for yourself. For me, I know that heads-down, focused work, I do really well in the morning. So I have blocks of time set aside for that.

LIBOR: Meetings and plannings are scheduled in the afternoon. I also have a weekly cadence. I think about structuring the overall week in terms of meeting with my peers to discuss different programs, different initiatives, what that looks like, early in the week. Then translating that into action items for my team, also early in the week. One-on-one’s are in the middle. Towards the end, a recap of the week. So there’s a weekly cadence.

LIBOR: And within the day, there’s also what times I work well. I work well in the morning. I also work well in the evening again when not too many people are around. For me, probably still very much engineering mindset, I think I’m most effective when I’m able to serialize my workload. Using my email as a to-do list and being able to just run through it one at a time. The longer continuous stretches of time that I can get to do that, the better.

LIBOR: And, then, I set time aside for reading documents or reviewing work. So, for example, every 7:30 a.m, I have half an hour dedicated to metrics reviews – operational and business metrics that I review every day to check on the health and status of the business. I have time set aside for postmortem reviews for all the postmortems that have happened in the last seven days. Going through those and combing through the action items as well as root causes. Spec reviews – where we have the last seven days of key specs and key decisions within those specs that need to be made.

LIBOR: So those kinds of things as well as progress report reviews, cross-functional report reviews. Reviewing what is happening in the business to make sure I stay grounded in the issues that are affecting the team and making sure they’re being dealt with in a timely manner.

Vidal: Okay. So blocking time seems to be the key.

LIBOR: Mm-hmm (affirmative).

Vidal: A key strategy you have.

LIBOR: Yeah.

What’s a personal habit that contributes to your success?

Vidal: Could you describe maybe what you feel is a personal habit that’s contributed to your success?

LIBOR: : I have a personal habit, maybe it’s a mindset, which is that, if something needs to get done, there’s no reason I can’t be the one to do it. So a lot of times, especially when you’re growing fast, issues become acute because nobody recognizes them as something that they themselves could potentially contribute to solving. They’re the types of issues that most people look around and go, “Well, that’s got to be somebody else’s problem and not mine.”

LIBOR: I’ve always been of the mind that, if I see a problem and no one’s taking care of it, there’s a high probability that the next person that comes along is also not going to look at it. I take charge, lean into it and solve it. And it could be anything across the spectrum – from kind of the mundane, coding or documentation, or planning exercise, or creating a spreadsheet for something.

LIBOR: At one startup I was running a team of engineers that were building a product and the product was having trouble selling into a very specific market that we needed to sell into. So I decided to hire a manager from my team and then I decided I was going to hit the road and start talking to customers to understand why this product that we had built wasn’t resonating with them and spent a large percentage of my time outside the office talking to customers and actually working with their engineers to utilize the product.

Vidal: That’s great. So just taking the initiative. Just to like get it done.

LIBOR: Yeah.

Share an internet resource or tool that you can’t live without.

Vidal: That’s awesome. Could you share … Are there maybe any tools, apps, or internet resource, or maybe something that you like rely on? Or find really helpful to you?

LIBOR: I try to simplify things. My day basically revolves around my inbox. And so that is basically the core of it. I try the actually strip down the number of tools and ways of getting things done, back to time management. Attempt to serialize my day and my tasks as much as possible. To just create focus on the task at hand and to get it done. And so, for me, it’s actually usually compelling the rest of my team to narrow down the avenues in which we engage.

LIBOR: I always tell people, “If you’re going to chat me, if you’re going to text me, if you’re going to call me, if you’re going to stop by my desk, that’s all fine. But just realize that, if you expect an outcome from me, then it’s got to show up in my inbox.”

Vidal: Interesting. So maybe the tool for you is your email Inbox.

LIBOR: Yeah.

If you could recommend one book to managers, what would it be and why?

Vidal: All right. If you could recommend one book for engineering managers and leaders, what would it be? And why?

LIBOR: You know what? The books I actually find the best about leadership and management are less directly about leadership and management, they’re more books where teams have come together to get something done – taking a large challenge and solving it. These books aren’t directly instructional about how to manage but give an insight into what’s possible. How different people have approached it, how they organize, how they actually got something done. At the end of the day, the purpose of it is impact. So seeing the impact, reading about the impact itself, and how they got there, is always an interesting lesson.

LIBOR: And I would say a lot of books that I, as an engineer, really enjoy about different time periods in the history of computing where teams have come together to do interesting things like, The Soul of A New Machine, or-

Vidal: I was thinking about that book.

LIBOR: … Where Wizards Stay Up Late. Yeah.

Vidal: Yeah.

LIBOR: But one of the really great ones in that genre is actually outside of software engineering, The Making of The Atomic Bomb, which actually won the Pulitzer a few decades ago. But a fascinating book about how an extremely large project was ultimately done on a very tight timeline with a fascinating bit of history. It’s interesting to reflect on what’s possible through high-quality leadership.

What is your approach to mentoring and coaching members of your team?

Vidal: I think that’s great. Yes. You probably can extract a lot of lessons from that. That’s awesome. All right. One last question here. Can you talk a little bit about your approach to mentoring and coaching, developing members of your team?

LIBOR: So, primarily by example. The way I think about it is the best mentorship and coaching happens when there are two important elements to it. One, it has to be contextual. There has to be this understanding of what is the context in which this person is attempting to develop. So what is the organization doing? What is it that they’re attempting to accomplish? Being able to observe them on an almost day-to-day basis about how they’re going about it to form, first, an opinion about what it is that they can improve on. But, then, also be able to talk to them on a regular basis about it just to make sure you’re calibrated to the challenges that they’re finding.

LIBOR: And, then, it is really an ongoing conversation and demonstration. So you lead by example. You show. You use yourself as examples. Use other leaders as examples as well that might be solving the challenge that this person is facing in a similar way. And the reason that these are really important elements is you have to make sure that what you’re providing, the coaching you’re providing, the feedback you’re providing, is actually suited for that person, for their approach, for who they are.

LIBOR: I think some of the worst advice or coaching that happens is when both, you’re giving feedback, but even the person that you’re giving the feedback to, is taking feedback that just isn’t going to work with their personality type. It’s just not the person they are. And that’s not how they look at the world. That’s not how they come across. That doesn’t play to their strengths. And they spend a lot of time trying to be somebody who they’re not versus mapping the problem that they’re having, the things they’re trying to accomplish to their strengths and who they are as an individual. So that is most important.

LIBOR: The other really important element is I think it’s really important to be mentoring and coaching someone who is not too far removed from how long it’s been since you had those challenges. It’s really important. So sometimes, it will happen where I’ll be managing somebody, but their experience of what it is that they need to improve on is something that I might have gone through personally 15 years ago.

LIBOR: 15 years is a long time and it’s not something that I’m likely going to be easily able to recall how I felt. How I experienced that situation. And that’s going to really mute to the kind of advice I can give that person. So, in those cases, I start to think about, okay, who can I find in our organization? Who’s been through this experience in the last five years? And actually, pair them up together because that’s actually going to be much more meaningful coaching and mentorship than I can provide.

Where can we go to learn more about you?

Vidal: That makes a lot of sense. Well, Libor, I want to thank you again. You’ve been super generous with your time. Some really great insights you shared. If people want to learn more about you, read more about you, is there any place where they could go?

LIBOR: Just on LinkedIn. And there’s a bunch of, obviously what I’ve done, but also links to interviews, other interviews and Q&As that I’ve done in the past. And I think that’s probably the best way to learn more.

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