Leadership as Craft

The craft of leadership requires a broad range of abilities, particularly at the executive level. Executives must be both strategic and tactical — able to see the big picture and attend to details where appropriate. They must be assertive but humble — able to deliver bold ideas but hold them lightly. And they must be strategic and relational — able to make tough decisions while attending to the human side of the people they lead.

There is perhaps no role where these requirements are more evident than that of the chief technology officer. While CTOs have existed at some companies since the 1980s, the scope and scale of the role have grown alongside technology’s importance. Charged with leading organizations’ long-term technology strategies, CTOs are critical players in keeping both legacy and digital-native companies ready for the road ahead.

Mike Fisher, chief technology officer at Etsy, is no stranger to the challenges of developing technology strategy and scaling solutions at a global platform company. For this edition of MIT Sloan Management Review’s Leading With Impact series, I spoke with Fisher about leading the technology team at Etsy, a company known for its engineering culture. Disclosure: In my coaching and consulting work, I have worked with Etsy in the past but had no active work with Fisher or Etsy at the time of this interview.

MIT Sloan Management Review: You’ve said that you practice leadership. To me, the word practice implies reflecting and asking for feedback. How do you incorporate reflection and feedback into your position as CTO?

Mike Fisher: Leadership is a craft. By that, I mean that there is no right answer. I developed this understanding from my time in the military, where your teacher or your boss is supposed to be your mentor. They watch you lead a group of students or do a job, and then they give you feedback. It can’t be taught in the classroom. In the Army, they can’t say, “OK, when X happens, you do Y.” Instead, they put you in situations, see how you react, and then guide you. To this day, I try to mentor in the same way.

One of my first jobs in my career was in inventory management for a supply chain. I developed software, solved problems, and built algorithms. I loved this job. But the project was behind schedule, so my manager’s boss, a mentor to me, recognized that I had leadership and management experience and encouraged me to lead the project. This push by my mentor helped me to take my first steps into engineering management, and, ultimately, she convinced me that this could be my career.

In my current position, I regularly receive 360-degree feedback — from my boss [Josh Silverman, CEO of Etsy], my peers, and the people who work for me. To add value, I also keep in touch with people I’ve met over the years. I have support from many smart but tough friends across various fields — some are CTOs, others are in finance, some are even professional athletes — to help me think through challenges.

With leadership, you’re always just practicing it, because you never master it.

As a leader, how do you give people feedback?

Fisher: No one likes receiving negative feedback, but I’ve found people benefit most from guidance when it’s given in a way that they can act on it in real time.

I want that too. Tell me the day — tell me the minute — that you see something so that I can immediately try to change it. To hone your craft, you need feedback.

You manage managers, primarily senior technology leaders. What are some common points of feedback that you find yourself giving to the people you work with? What are their common challenges?

Fisher: A common challenge is not understanding what I call the language of business. My first mentor told me, “You can’t go into a meeting with your business partners and talk tech, because they don’t speak that language.” The universal language of business is finance. You need to be able to speak that language.

In fact, what drove me to pursue my MBA and doctorate in management was the desire to understand business. I felt that I would be a better technology leader if I learned what my business partners had learned throughout their careers.

Senior technology leaders and chief technology officers don’t get fired because they’re not technical enough. They get fired because they can’t explain the rationale of why they made a technical decision to other people in the organization. They can’t explain how it’s going to improve the bottom line or help the business scale. The job of a CTO is not to just make technology decisions — it is to translate those decisions into the language of business.

I think the other way that CTOs get fired is by not understanding or communicating the human element of risk embedded in a technology-related decision. It can go sideways if a CTO delivers a project plan that doesn’t acknowledge that risk.

Fisher: I agree. Technology leaders fail because they can’t quantify or explain the risk or offer mitigation plans. Also, when I was a consultant working with organizations, I noticed that the most technical person on the team often became the manager. That’s not necessarily the best approach.

In fact, it’s probably worse than choosing someone at random.

Fisher: It’s probably worse than random. If they are super technical, they probably don’t want to manage, because they love the technology.

My belief is that engineering management is a discipline in and of itself. It is not a promotion from engineering.

We’ve tried to embrace that at Etsy. In our world, as an individual software engineer, you can go all the way up to the equivalent of a vice president. This gives people opportunity for promotion and advancement without forcing them into a management track.

Etsy was relatively late in making the shift from on-premises servers to cloud hosting. In terms of technology, how are you and your team working to stay ahead of the curve?

Fisher: When I came on board in 2017, I took an approach of trying to learn what brought the company to a lot of its decisions. Etsy was an early innovator in many ways; it built a super-strong engineering culture that drove innovation. The company helped pioneer the use of blameless postmortems and DevOps practices like continuous deployments — something we still do dozens of times a day.

In the case of sticking with on-premises servers versus cloud hosting, I think Etsy’s challenge was that it never went back and reviewed that decision. When I became CTO, I gave the team an opportunity to revisit and assess. Ultimately, we decided that the right decision was to move to the cloud, and we recently completed that migration.

I’ve given my team the OK to reconsider previous decisions. I’ve tried to make that a principle that we want to be known for as a company. Etsy has always been a learning organization, meaning we share learning and we try to learn from other people. Our Code as Craft engineering blog and speaker series serve as channels for people to showcase their knowledge and teach others. As part of this learning culture, we need to rethink our decisions periodically with this same openness.

And we’re starting to see that happen. For example, we built machine learning infrastructure because, at the time, there was nothing available from service providers. Fast-forward a couple of years, and now there are many options that fit our needs. It’s nice to see my team come forward and say, “There are other options that we should look at.”

This mindset of being open to learning and taking action from it — I think that is what is going to guide us forward and help us to stay abreast of all the new technologies and opportunities. It’s the mindset, not the technology.

Many technology businesses in the world are a similar age now. They’ve had enough time to accrete complexity and technical debt at the level of code and architecture. But what you’re talking about is the business level of technical debt. You’re proposing that we encourage routines to reexamine decisions made 10 or even 15 years ago — decisions that were the right decisions for the time and for the environment.

Fisher: Right. I think that’s particularly important when leaders come into the company. When they come into their role, it’s important that they take time to understand and show respect for past decisions. They should learn how the decisions were made and understand what the rationale was of stakeholders at the time. That doesn’t mean we shouldn’t rethink the decisions, but we shouldn’t say that they were all wrong.

In everything we do, we start from the assumption of best intentions. No developer goes to work and says, “I’m going to push code that breaks something.” Likewise, nobody says, “I’m going to make a bad architectural decision that is going to haunt us for years.” Everybody makes the best decision that they can based on the limited information that they have at the time. It’s not the right leadership approach to come in and say, “This is all wrong.”

Part of the craft of leadership involves listening to and incorporating feedback. But another part of it is having the courage to reimagine old ways of doing things. You can appreciate why a past decision was made. But it doesn’t mean you can’t change it.