The armchair guide to engineering leadership Posted at 0:00, Mon, 1 August 2016 in Industry Insights

I’m stereotyping here, but many engineers (especially young, inexperienced ones working at startups) see management as unnecessary overhead. They don’t see the value in having an engineering leader, and may or may-not respect non-technical contributions to the team. This tends to change once they work with a great leader, or have worked through a couple of poorly-managed failures.

One of the more challenging aspects about my job is judging engineering leaders without being an engineer. I’ve shared this challenge with hundreds of founders and executives who aren’t technical, but are responsible for hiring technology leaders.

You often can’t rely on the current technology team to identify, interview & attract their future boss. It is up to business leaders (often Founders) to socialize the decision to the team and make the right hire with limited technical knowledge themselves.

As such, I’ve created a framework through which to judge what kind of leader is the right for a role based on what a company needs.

No framework is perfect, and this model is only meant to set up a high level understanding of what kind of leader you’re looking for and a framework for your team to debate around.

I’d like to mention two big common mistakes before we dive into the framework itself.

Don’t conflate “Hands-on” and technical acumen

Technical acumen is separate from how hands-on someone is. There are people with terrible technical acumen who code daily, and some people with fantastic technical acumen who are pure people & process leaders. Everyone should want to hire people with excellent technical acumen, but may or may not need someone hands-on.

Hire someone who fits what you need right now, not someone with the biggest, most impressive, experience

Raffi Krikorian (ex-VPE at Twitter and currently at Uber) wrote a great article on what a VP of Engineering really does (or should do). Spoiler alert – being the best engineer on the team is not what a VPE is judged by.

Eric Larson from Riviera took this one step further and started to flesh out some different types of engineering leaders that are right for different stages of companies.

FYI – Each level has a football analogy attached to it (I like football, it’s my article!)


The Framework

Active Coder – Team Captain

Profile: Usually an architect or engineering lead who still codes and commits regularly. Might have a management title but would only be a VP or CTO at a tiny company (or in a non-people leader CTO role). May or may not have management training. Often they are a strong engineer who has been recognized as a potential leader and handed people to manage or someone who is making a conscious career choice to remain (mostly) an engineer. They live for technical challenges and while they enjoy mentoring engineers, they don’t want to get too far away from their first love.

Strengths: Will pick up the ins and outs of all your code & technology on a granular level and quickly will gain the trust of the engineering team as a result. Can mentor engineers by leading by example and walking them through issues. Can help you make tactical technical decisions without slowing down delivery. Ideal for pushing out features on a single product.

Weaknesses: Active coders tend to struggle to scale people & process as they are too drawn into the day to day coding challenges & exercises. When they do lead teams, they often lead by example and don’t spend as much time building up functions like recruiting, process, architecture, and executive-level relationships with other functions.

Why hire: You have a really small and junior team that needs someone who can flat out execute, and teach the team how to do that by being an example of how they should all be as well. They can make good co-founders who can begin by coding themselves, and slowly build a team around them. Once they get beyond their ability, they will either have to hand off responsibility to someone else, or grow into the next level/role. Gives someone your team feels good rallying around as they might be the best engineer, and people see very clearly what they can learn working with them. They can be ideal for 3 – 15 person teams.

“Hobby” Coder – Positional Coach

Profile: While less of a coder than level one, the “hobby” coder still reviews code frequently and may commit from time to time. Often, they will wireframe or build prototypes that other engineers will take and put into production. They understand leadership concepts and can likely manage a manager in addition to direct reports. They are probably still ambivalent about taking themselves away from code, but are realising more of the value of leading bigger groups, releasing bigger products/features and starting to enjoy the mentorship aspect of their work. They are probably manager or director level, but might have been a VP before at a small company.

Strengths: They understand much of the day to day of what’s happening and can speak to code quality across all their teams as they are usually the ones in code reviews. They are still pretty lean and execution-focused in their mentality, but understand more about appropriate process and have some idea of what the business needs out of engineering beyond features and could likely manage engineering for a small portfolio of feature sets.

Weaknesses: Given their level of knowledge & ability, they can often micromanage teams & technical decisions and struggle to know what they should (and shouldn’t) decide themselves. They tend to hit a wall when being asked to manage other leaders for the first time and can struggle to give them adequate space & opportunity to grow (while managing risk). Unless they’ve been a founder, they are likely new or inexperienced at the executive team level and won’t be a strong contributor to the strategic vision of the business.

Why hire: You have a smallish team that needs a leader, but not someone who is out of the code (yet). They perhaps have the precursors of being a great engineering leader in their own right and can grow with the role over time. They should easily be able to win over young/small engineering teams with their hands-on ability, and are a strong enough coach to mentor them as well. They can be ideal for 15-25 person teams.

Architectural Reviewer – Defensive Coordinator

Profile: This is where many early stage VPEs fit and it’s the first level I consider a true executive. They’ve gotten to a point where they are leading at enough size & complexity that they know they can’t run the show at the code level, but they also know that their architectural insight is important to the organisation. While they may occasionally survey some code reviews, they mostly entrust that work to others and focus more on design/architecture level technical discussions. Some will still tinker with code but will struggle to find time at work and will scratch that itch at home or on the weekends with side projects. They have fully embraced the challenge of leading engineering teams at scale, but still enjoy technology challenges. Most of their direct reports will be managers, directors or architects.

Strengths: They have ideal range for early startups. They can come up to speed on technical challenges that are slowing the team down and drive delivery, but can still communicate with other executives at the business level. They know what it takes to recruit, build teams & process and establish other leaders in their organisation. They can manage delivery on a complex product roadmap and will not forget about technical debt. They know enough about the technical details and architectural direction to challenge the engineering team’s thinking.

Weaknesses: They require engineers to buy-in but won’t be able to gain their trust through coding, it’s important that they have a strategy to overcome that and the business team & founders support them. If they come into a company early they may not be as effective as a L1 or L2. It’s also important that they build a high level of trust with other executives as they are still figuring out how all the pieces fit together at the strategic level. They will likely struggle with the level of scale & polish to take a company public. They can be bullied into accepting goals that are too aggressive and under-deliver.

Why hire: You might be outgrowing a beloved founder, or bringing in your first real executive and want to pull someone in that isn’t too big a departure from the current team’s skill set & worldview. They have the gravitas to work with early-stage executive teams and still debate technical direction with their engineering team. Your company probably has found initial product-market fit but now needs to scale. Ideal for 30-60 person teams.

People & Process – Head Coach

Profile: This isn’t their first rodeo as they’ve been an engineering executive before and lead at scale. They’ve been the throat to choke for engineering and understand how to work well with the executive team while leading through their directors & managers. They might have the ability to debate technical details, but likely won’t be present at code reviews, and probably entrusts architectural decisions to others on his team. While viewing it through the lens of engineering, they are fully focused on business & product success and may not even code anymore. They see technology decisions in terms of trade-offs & resources and know that their team is only as good as the people & processes that they have assembled and invested in. They should be a capable recruiter and should have a track record of developing engineers in to executives.

Strengths:  Will be a key player at the executive level and build a motivated engineering leadership team around them. Should create an environment that ‘runs smoothly’ and doesn’t have huge resource challenges. Will do a good job of establishing targets at the executive level and making sure his team always hits the mark. Will push back on unrealistic expectations.

Weaknesses: Without scale & resources, they struggle to contribute heavily. Success comes with a price, some of these leaders won’t be as adaptable and may be too set in their established (previously successful) ways of doing things to fit every company’s culture.

Why hire: Your technology works and has survived rapid scaling after hitting product-market fit, but now it’s time to see how big & reliable it can get. Ideal for 60-100 person teams. Your business needs to start running like clockwork and avoid unpleasant surprises at the board level.

Corporate Leadership – Is the GM, hires & fires head coach(es)

Profile: This leader has achieved significant scale and is more of a technical GM than a pure engineering leader. They make high level decisions on who owns what, how to organize teams, and the most technical decision they likely make is whether to build or buy different technologies. Only the largest startups have use for leaders of this scale, and you’re most likely to find these people in Pre-IPO startups or corporate technology companies.

Strengths: Has an unparalleled understanding of how engineering integrates with every other component of the business and can speak the language of investors, product, marketing, sales & other key functions of the business. They are highly inspirational and should be expert at working themselves out of a job by developing strong leadership around them. They will shape the culture of the engineering leaders who will in turn deploy into the organization.

Weaknesses: Not right for small companies (at least in a VPE role, might be your CEO or COO for a very technical product). Might have great technical acumen in the technologies they grew up with but might struggle to stay up on new technologies and trends. Like L4s, might not be malleable enough to be successful in different company cultures.

Why hire: Preparing to go public, or already being public, you need someone who is rock-solid with investors, board members and the executive team. They can understand every aspect of the business and are a key contributor and leader at the company. Perhaps a large company with lots of resources needs someone who can ramp up a new line of business and can balance business, technology & corporate politics.


Are the levels set in stone, or can people move between them?
The barriers between each level are somewhat arbitrary and many leaders routinely shift between them throughout their careers.

While it’s relatively easy to move one step in any direction, it is quite rare to find people who can operate across the entire spectrum and be as strong an Active Coder as they are a Corporate GM.

Many leaders tend to grow their career as people managers and have to take a step or two beyond their comfort level before they understand where they enjoy their work the most.

What should I do if/when I outgrow my engineering leader?
This happens all the time. You have to have an honest conversation around the needs of the team, the company, and as importantly, what’s right for the leader being outgrown. If you’ve hired well, the leader should understand when they aren’t strategically the right leader for the organisation. That doesn’t make it an easy conversation, but to the extent you can have an open and honest conversation about it, that’s the best starting point.

In my mind, you have 3 choices.

1 – If the leader wants to grow into the role and you want them to as well – be prepared for them to struggle, but invest in coaching & mentorship to help them make it to the next level and keep up with them on their progress and hold them accountable to the outcomes you need.

2 – If the leader doesn’t want to grow into the role and is open to being managed – start the search to help them find a new technology leader for the department. Make them a key stakeholder in the hiring process but make sure that a) they aren’t secretly wanting the role themselves and b) their individual biases (technical or otherwise) don’t distract from hiring the best person for the job.

3 – If the leader doesn’t want to grow, or can’t (or the company can’t delay) into the next level and isn’t open to being managed by a new leader. You have to either conduct a search confidentially or let them know you are hiring someone to replace them and let them make their decision. In either case, it’s best to hire someone quickly and rip off the band-aid. You may or may not be able to repair your relationship with the existing technology leader and be prepared for them to take flight (but it’s often best if you can convince them to stay in a role they can get excited about).

How do engineering leaders build trust with the team if they can’t code circles around them?
How does anyone? You have to build the team’s belief in the value of leader’s work. Help them stop wasting time building things that don’t matter to the business. Help their wins become more visible in non-technical groups. Help buffer engineering teams that need time to change from quickly changing business needs & priorities.

UPDATE July 2016: We are actively working on a number of Senior VP Engineering roles (leading 100 to 300+ engineers) in both the Asia Pacific and the San Francisco Bay area. Please connect with Jason Heck in SFO or Simon Robinson in APAC if you would like to discuss great opportunities with the most exciting growth ventures on the planet.

What are your tips when it comes to engineering leaders? We’d love to hear from you on Twitter @MitchelLake