The programmer's guide to breaking into management

The transition from command line to line-of-command requires a new mind-set -- and a thick skin

Software development, like any career, is divided into leaders and producers. You're either Steve Jobs, or you're Woz. Two completely different approaches, and yet both can lead to great success.

Talented engineers may see managing a team as the next step to growing their careers. So if you're moving in this direction, what tools do you need to make the transition? We'll look at some possible approaches, common pitfalls -- and offer solutions.

A first question might be whether to make a change at all. What if a Woz-like existence is more your style? Knowing yourself and whether management is really where you want to land is worth some self-reflection.

"You have to think about what aspects of the job you really enjoy, and which you try to avoid," says Adam Wolf, head of engineering for foundational applications at Bloomberg L.P. "If what you really enjoy doing is bringing everyone together to accomplish something as a team, or building a vision and getting everyone behind it, then management is a great opportunity to have a broader impact."

Consider the management transition thoroughly

The management track begins right where you are, in your current position. It requires taking on more responsibility, reaching out to team members, and making yourself visible. Because of this, you probably have a good first approximation of what to expect and an inkling of what will be expected of you, but there's a lot more to it than that.

Rick Hutley, clinical professor of analytics at University of the Pacific, advises checking how thick your skin is before you plan to manage others.

James Casey, vice president of engineering, Chef

"Demonstrating that you can excel in your current responsibilities builds trust that you can move to a role with more responsibility." --James Casey, vice president of engineering, Chef

"Ask yourself how well you tolerate risk and criticism," says Hutley, a former CIO at British Telecom, and vice president of innovation at Cisco Systems. "Be honest. Better to be a happy grassroots worker than a miserable leader. That said, stretch yourself. Have the courage to move outside of your comfort zone and take on more responsibility."

Managing others will often lead to awkward situations. An exceptional career can be uncomfortable. And good managers are driven by a desire to lead and understand that delivering criticism may influence people, but maybe not win friends.  

"Leadership means making hard decisions on occasions -- disagreeing with those who used to be your colleagues -- and it can be a lonely place," Hutley says. "The higher up you go the more certain it is you will fail -- in someone's eyes."

James Casey, vice president of engineering at Seattle-based enterprise software firm Chef, says you can communicate your desire to move up the ladder -- and this is critically important -- by showing you have the qualities possessed by a good manager.

"Leadership and mentoring are at the top of the list -- as an individual contributor," Casey says. "In parallel, ask yourself, 'Would my teammates want me leading this team? Why? Why not?' As you're thinking through how to move up, you need to be doing your current job very well -- demonstrating that you can excel in your current responsibilities builds trust that you can move to a role with more responsibility."

But if you've never managed people before, how can you know if leading others is a good fit for you? Hutley offers these tips: "Are you one of those who tends to think beyond the immediate task, not just at work but socially as well? Do you suggest a better way of doing things or challenge things when they don't seem right? Do others seek you out for your thoughts or guidance? If this is you then you are a natural leader -- and others recognize it too."

Communicate your plan

If you're hopeful hard work and attention to detail will speed your way to the top, you may need to broaden your plan. The leap to management will mean a complete redesign of your work life. But the first step is to telegraph your intentions to your boss.

Silicon Valley executive coach Jennifer Selby Long has spent two decades helping software developers move into management and effectively lead teams. Long says that great work isn't enough to send the right message -- you'll need to be more up front. And it's not always easy.

Sarah Nahm, co-founder and CEO, Lever
"Look for the fastest-scaling areas of the business, since those areas will present a tremendous number of organic opportunities to step up and take on additional responsibilities." --Sarah Nahm, co-founder and CEO, Lever

"Nearly all software engineers want to remain software engineers, so your boss won't know that you want to get into management unless you say so directly," Long says. "Discuss your desire to contribute more to the company and take on a new challenge, not just in terms of how you want it for your own career benefit."

Performance reviews and other one-to-one meetings are a good time to lay out a desire to move up the ladder. And your manager may be able to help you determine what skills you need to develop to make it happen, says Chef engineering VP Casey.

"Regardless of whatever system your company uses for documenting your long-term career aspirations and directions, your one-on-one meetings with your manager are the best time to discuss your goals in detail," Casey says. "If you and your manager are both agreed on the path you need to take to reach management-level responsibility, then they will also be your biggest advocate. That's the best route to success."

And along with these other tips, if you're looking to make the move, one of the subtle yet painful changes might be changing the way you present yourself at the office. It's obviously a personal choice, and Mark Zuckerberg aside, if you're going to be running meetings your street clothes may need to go.

"The best advice I ever received was: 'If you want to be something -- look like it,' says Hutley. "When a company wants to fill a position they look through their mental rolodex for someone who 'looks like' the person they are looking for. It's too late to start looking like a leader when the job advert comes out -- you have already been pigeonholed by your actions up to that point."

And that subtle shift toward wearing the part -- and separating yourself from the pack -- may be enough for the friction to begin.

Jennifer Selby Long, executive coach

"As a manager, your job will be 90 percent about influencing people, which is an inherently illogical task." --Jennifer Selby Long, executive coach

"Looking like a leader can itself be a little uncomfortable. Wearing neat pants and clean shirts when everyone around you is in jeans and sneakers can lead to some leg pulling," Hutley adds. "But you can't climb the ladder by standing on the bottom rung with everyone else. You have to differentiate yourself in the way you look, speak, and act."

Help along the way

You could, of course, apply to an MBA program and complete it online or after work. Public speaking courses can help, say our experts, along with budget training, self-assessments like Myers-Briggs, and training in diversity and inclusion. But there are plenty of opportunities at the office that can help you move in the right direction.

"I should disclaim this answer by saying that I don't have an MBA," says Bloomberg's Wolf. "My feeling is that I learned more about being a manager by actually being one, than by learning about the role. I have taken classes and read books on management, but I found the thing that helped me most was getting good feedback from my colleagues, managers, and my team, and from watching role models and trying to learn what made them effective."

"Find mentors," agrees Hutley. "These do not have to be people who have been formally assigned as mentors -- although they are good too. Identify leaders you resonate with -- who display qualities you admire and wish to emulate. Then observe them whenever you can and understand why you admire them: How did they handle a particular situation; how do they dress, speak, act?"

Pursuing certification in your field can also show that you're looking to advance, says Eric Klein, managing director of staffing firm HireStrategy. And you can show leadership qualities by helping along new or junior colleagues.

Adam Wolf, head of engineering for foundational applications, Bloomberg L.P.

"You have to be comfortable standing behind the work your team is doing." --Adam Wolf, head of engineering for foundational applications, Bloomberg L.P.

"Suggest a peer code review when a colleague is stuck in development," Klein says. "Aside from managing projects and teams, mentoring junior staff and peers can demonstrate your ability to lead others."

Sarah Nahm, a former Chrome team member at Google, advises you to look for areas where your current business is growing.

"Engineers should pay attention to the business around them," says Nahm, who now leads Lever, a Silicon Valley firm that helps companies hire well while scaling up. "Look for the fastest-scaling areas of the business, since those areas will present a tremendous number of organic opportunities to step up and take on additional responsibilities. Volunteer to do more interviewing and take a front-row seat to strategic hiring decisions. You'll see exactly what qualities are important to your engineering org, and also get a head-start on a critical skill for when you need to hire engineers for your future team."

Making the transition

One of our pros says management offers many of the same challenges and uncertainties as parenting. He then quickly adds you must never actually express that -- or you'll risk alienating your entire team. Along with that handy analogy/warning, here's a blueprint for the transition.

First, get ready for "a complete and total career change," says executive coach Long. "There are no product specs or algorithms for people. As a manager, your job will be 90 percent about influencing people, which is an inherently illogical task, and dealing with ambiguity in the business while still producing results through others, which is also a task that can't be done by leaning on logic and reason alone."

And now for the really tough part. Are you ready to hand over control and let your team do their jobs?

Mark Stagno, principal consultant, WinterWyman

"In a 'what have you done for me lately' industry, your ticket … is your technical skill-set. If you abandon that, you are vulnerable." --Mark Stagno, principal consultant, WinterWyman

"The worst managers are those who maintain too much control," says Long, "yet micromanagers always, always think they're doing the right thing. Can you dedicate yourself to guiding, supporting, directing, and advocating for others? At first, it's a white-knuckle ride. Be sure you're ready to get on that roller coaster."

And what if your team includes former colleagues from your workgroup? How do you retain a collegial relationship with these co-workers?

"You have to remain sufficiently detached to be objective and to make and communicate the hard decisions honestly," says Hutley. "It's very hard to give hard negative feedback honestly -- and it's hard for both parties, not just the leader. That said, you don't have to completely shun your old colleagues."

Let your team stretch their skills, our pros say, and be ready to do some nail-biting when they fail. Again, these skills -- communicating effectively, being persuasive, and keeping your cool during times of uncertainty -- may not come naturally. But they can be learned.

"A leader guides and coaches and then lets the chips fall where they may," Hutley says. "Be ready to praise when things go right -- something we forget to do all too often -- and to support and encourage when things go wrong."

Bloomberg's Wolf agrees and advises new managers give their team the same autonomy they wanted before they made the jump.

"You can't go too far and abdicate responsibility," Wolf says. "You have to be comfortable standing behind the work your team is doing. I find it's helpful to focus on asking good questions of your team, and letting them reach the right answers."

And don't give up on what got you this far. The quickest way to become out of touch is to let your skills get rusty.

"Use mainstream technologies that are transferable from one company to the next and remain hands-on," says Mark Stagno, principal consultant at staffing firm WinterWyman. "In a 'what have you done for me lately' industry, your ticket ... is your technical skill-set. If you abandon that, you are vulnerable, and if things change -- the company begins to struggle or you become unhappy -- it won't be as easy to find a job if you aren't hands-on."

An argument for staying put

Let's also consider that engineers who move up may look back wistfully to a time when building and deploying code was the focus, rather than managing a product, budgets, and a team.

HireStrategy's Klein says he occasionally hears from engineers-turned-managers that they miss the hands-on work of coding.   "With technology constantly changing and evolving, managers notice their technical skills slipping even as their management skills improve," Klein says. "We remind candidates that, at the end of the day, it's all about each individual finding what they love to do every day. Careers can excel without going down a management track."

Michael de Groot, chief architect, Geneca

"As a manager, your responsibility will be less about doing the work and more about helping others be successful." --Michael de Groot, chief architect, Geneca

Many engineers enjoy a solo approach to problem solving, says Michael de Groot, chief architect at software product development firm Geneca, and take pride in coming up with novel solutions on their own.

"As a manager, your responsibility will be less about doing the work and more about helping others be successful," de Groot says. "You'll have to deal with other people's behaviors, attitudes -- and differences in work ethic."    

And one final thought about moving up the ladder. In a time where rock-star developers are hard to find, being the boss may not mean better compensation. It's a far different world than when Woz looked around his calculator-producing colleagues at Hewlett-Packard -- and thought he'd found a job for life. In today's market, those who can innovate are the ones in demand.

"Engineers at the top end of the market are now making the same if not more than a line manager," says WinterWyman's Stagno. "Think long and hard before taking the plunge into management, and above all else, make sure you are doing it for the right reason -- that you want to be a leader rather than simply wanting to move up the career ladder."

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This story, "The programmer's guide to breaking into management" was originally published by InfoWorld.

Copyright © 2015 IDG Communications, Inc.

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