Exec Chat: Transitioning from Engineer to Executive
What does it take to transition from an engineering role to a leadership position? It’s a journey not many venture take not necessarily for lack of acumen, but simply that only a small fraction of employees actually aspire to step into that role. And this can be particularly true for engineers as many are hard pressed to trade in their hands-on technical positions for team leadership.
Leading a team doesn’t typically come natural to most individuals, and this can be particularly true for practical and pragmatic engineers. But technical experts who do cultivate leadership skills are typically well-positioned as they bring together highly valued skill sets and characteristics — problem-solving, deep thinking, tenacity and curiosity — that are mission critical to any organization, especially in environments where the rate of change is ever increasing.
It requires dexterity in finding the right balance between leading at a strategic level and getting into the trenches with the technology and the processes.
In this Exec Chat, Indu Khosla, director of engineering at Shopify, and Eric Miller, principal and co-owner of PADT, share how they approach leadership, the skills they developed in transitioning from their engineering roles, and what today’s leaders should focus on developing.
How do you keep yourself sharp?
Indu: To stay informed, we read newspapers, books, etc, but how we stay sharp is more about a practice in a way. I do this by creating the environment to be sharp, which means health — getting enough sleep exercising, but also avoiding decision fatigue so that the moments when you really do have to make critical decisions, you are aware. So, maintaining a lifestyle where you limit the decision fatigue so that you are sharp for the critical decisions you have to make.
And then the other part is practicing to stay sharp, especially these days in a very attention-deficit environment. It’s very easy to get distracted. So many things are available and human beings are inherently designed to conserve energy. So anytime we are trying to do something that takes a little bit more energy, we are naturally drawn to not do that. If you’re going to read a complicated article or complicated paper, it’s very natural to want to instead go on Twitter or go on your phone. So, I practice focusing and paying attention for long durations of time. If I’m reading a technical paper, I’ll set my phone on a lock so I don’t distract and really just force myself to pay attention.
Eric: I’m a, a big believer in lifelong education and constantly educating myself on new things, whether it’s technical with what we do here at the company or whether it is based upon business or marketing or sales. It may be reading a book, listening to a podcast, going to a Tech Council webinar or seminar and learning from experts, etc. I went back to school for the first time in 30+ years to sharpen up my writing skills. Make learning a priority, not an “I’ll get to it.” It needs to be a priority. Even to the point of when I do a task, or learn a new tool or a new process, I set aside the time to not just get it done, but to really learn it and, and take some time to dig deeper into it so the next time I do it, I can be very fast.
What are the most important attributes of successful leaders today?
Indu: The rate of change in our industry is getting faster and faster. So the most important trait for leaders is to have different mental models that they can apply to a situation. Because as a senior leader, when you come into an organization, it might be in a different place. It could be that a team is struggling or it could be a team is executing well, or maybe they don’t have a good technical strategy, etc. We work in a social-technical environment. So there could be lots going on and you have to arrive with different mental models and be able to update your mental model so that you can solve problems correctly.
One of the things I see, for example, is there’s a lot around agile transformation in our industry where sometimes leaders have a single mental model of what an agile executing team looks like. And without understanding the situation, the company or the culture, or even where they are in their technical maturity, they might apply the same mental model again and again, and that doesn’t then work. So, the most important trait for a successful leader is to have different mental models that you can apply or upgrade, that really helps you be successful.
Eric: I think timeless is listening. Not just letting people talk, but actually hearing and understanding what they’re saying. That’s huge regardless of what kind of leader you are. The second one that has maybe jumped up on the list is flexibility. It’s always been an important trait of a leader, but if we’ve learned nothing more in the last two years, it’s be flexible.
For my style of leadership, which may not work for other folks, leading by example is really important. I feel really strongly that I should be able to do what my employees do and if I don’t do it, I should know somewhat how to do it, or at least understand it. And occasionally actually do it. It’s not necessarily the best use of my time, but it helps them understand that I understand what they’re going through. It helps me help them solve problems. For me, again, thinking about the long term, big picture rather than today’s crisis — combining strategic and, and tactical thinking.
What’s the most important risk you took and why?
Indu: What I find is that in business and in life, in general, anything that happens quickly, any drastic change is usually not a good change. An accident could change your life drastically, but it’s not a good change. Whereas all good changes in life happen a little bit more slowly. So I like to think in terms of not risk taking, but making big bets. Making a bet that you can then go behind and work at it. Because in senior leadership positions, a lot depends on us. Risk, to me, implies lack of care. Whereas making a big bet implies you do take care. You do think about it.
I like to think about it that way — to make big bets. But as far as career goes, the three big bets I’ve made in my life and in my career all involve taking a step back to be able to grow. For example, the first big bet I made was choosing to go to engineering school to study computer science without ever having touched a computer. Similarly, early in my career, I was in a really rapid trajectory, growing very fast in one of my first companies. However, once I had young children, I made a big bet that if I took time to focus on my family later, I will be in a much better space to grow my career.
Knowing the circumstances, what was happening at that point, what was going on with me, my family, the company, how I was thinking about life in general, I demoted myself back to IC roles so I could have a little bit more balance in life. I made the bet that would be best for my family, and career-wise, I’d have the opportunity again. And it did. Similarly, when I moved from GoDaddy to Shopify, I was a vice president at GoDaddy and I decided to move to a director role at Shopify. So that’s taking a step down. However, to me, it was a big bet toward how it was going to prepare me for the next stage in my career.
Eric: Starting the business. Our company is 28-year- old and we’re basically a value added reseller to mechanical engineers that also does consulting for mechanical engineering. We help people who make physical products. And we started the company when there was no such thing as a startup. That was not a thing. In 1994, however, in the midst of a bunch of layoffs, we decided that the technology that we used for a large corporation was applicable in other industries and we should start a company based on that. Taking that leap of faith and going for it was the big risk.
The second biggest risk further on — and I have to take it all the time — is trusting other people to do stuff instead of me doing it. It’s hard as an entrepreneur to do that. You’ve got to let go and trust that the person you’ve hired to do it can do it. And 98% of the time they can. And don’t worry about when the 2% happens, deal with it, but don’t hold back because of that 2%.
What advice would you give to upcoming leaders?
Indu: I can only talk about my field in engineering and technical leadership, but the advice is to always stay technically sharp and connected. This doesn’t mean you have to code every day. It’s actually wrong to think of coding as a proxy for technical acumen as a senior leader.
As you go into senior leadership, you have to be super aware of different ways of doing things. You have to understand where the industry is going and how software practices are evolving and changing. As a senior technical leader in any organization, in the end, you want the company, technology and platform or product to evolve really fast. It’s not just about how much code you write. You have to think about how you structure your teams and your technology, and consider new mental models and org structures. This requires staying connected to technology.
One of the mistakes a lot of technical leaders make once they start getting into senior leadership positions is they start getting into a project management mindset where they’re delegating all technical decision making to the team. Strategy is all about the technology. You can’t make strategic decisions while ignoring your technical setup. So you have to have an understanding of that and have enough technical literacy to understand how to adapt and grow.
Eric: Don’t be a fear-based decision maker. I see that a lot. Making decisions based on the worst thing that could happen rather than the best thing that can happen doesn’t usually work too well. One of the other pieces of advice I give to CEOs is it always takes longer than you think. Whether it’s fundraising, getting sales in the door, getting your prototype product done, or hiring somebody, it always takes longer than you think.
And not planning for that, and being ready for it emotionally, as well as practically, is really important. I’ve seen entrepreneurs lose steam because it’s just taking too long and you just have to accept the fact that this takes longer. The investor said they’re going to send a check next week. They’re not sending a check next week. It’s going to be two to three months if their lawyer’s not involved. And if the lawyer’s involved, it’s going to be six months. It just takes time for these things and don’t let it get you down. Have contingency plans. It’s much easier to adapt to something happening sooner than expected than scramble when it doesn’t happen when you expected it.
