If you are fortunate enough to work at a tech startup that is experiencing some success, you will likely need to hire more engineers. At some point, as this process progresses, you may well find that you need to hire someone with management and leadership experience to run the growing engineering team. Most startups that need to hire an engineering manager do so because their current staff lack the skill set required for the job. Ironically, because they lack those skills, they may not have a good idea as to what the right skills are and how to evaluate them.
Reiterating: You may think you know what you want and need in an engineering manager, but if you lack experience in the role, you may be looking for the wrong things.
Get Organized
An organized approach is always good for interviewing, but particularly necessary for a key engineering leadership role.
1. Determine your specific needs.
- How big is the current team?
- What problems does your team currently face?
- Where are things straining as the team grows?
- What sorts of non-engineering problems is your team experiencing?
- Talk with your current team to get additional perspective.
2. Anticipate the direction you believe your engineering team will take.
- How many engineers will you hire in the next year? In the next two years?
- What is the expected mix of local and remote hires?
- What sorts of processes will the team need to adopt?
- What mix of roles and technical skills will be needed on the team (QA, PM, Ops, Security…)?
- What organizational challenges do you anticipate?
- A hiring roadmap will help you to determine the experience level required for your engineering leader.
3. Talk to experienced advisors/investors/board members/peers.
- What skills do they believe are necessary for the job?
- What areas would they suggest you explore with each candidate?
- What specific questions would they ask, and what are some of the answers they would look for?
- Better yet, get these experienced people into the actual interview process!
The Wrong Questions
Some of the more common questions used to screen prospective engineering leaders include:
- What is the largest engineering team you have managed?
- How many people have you hired?
- What is the highest title you have held?
- How technical are you?
These are probably not the best questions for you and your team. Often they are mediocre defaults which, in the hands of an inexperienced recruiter, might screen out great candidates. Do some preparation ahead of time and prepare deeper screening and interviewing questions that more directly match your needs.
Another common mistake is to narrowly focus on managers from large, successful companies as potential managers at your small, scrappy startup. Big name companies hire good people, and can afford quality training, so managers from these companies have some advantages. But there are substantial differences in managing at small companies vs. big companies. Managers at big companies benefit from large support staff, top end tools and systems, great benefits, and top pay for their teams. Succeeding at one of these companies requires skills like inter-team negotiation, project alignment, and cross-organization coordination. I have spent some years managing at both large companies and small companies—they are not the same. Target great individuals, not just great companies. You will be hiring the individual.
The Right Questions
Look closely at your actual situation to determine the types of issues your engineering team faces, the sorts of candidates you are looking for, and the questions you will want to ask them.
For example:
• Are you spending too much time or having trouble coordinating the efforts of your teams? Screen candidates on project and product management skills and processes, and ask them for specific examples of successful coordination during the interview.
• Is morale faltering as the company changes? Look for candidates who have worked at growing companies. Ask them for concrete examples of how they have addressed morale and other scaling issues.
• Is the quality of work decreasing as the team grows? Consider screening for candidates who have lead QA teams. Ask them to suggest multiple solutions to a specific problem you present (make a couple of options available to them).
• Are employees starting to stagnate after they’ve been at the company awhile? Look for candidates who have spent multiple years managing people and have found ways to help their engineers develop their careers.
• How much of the engineering tasks vs. management tasks can you (or do you want to) handle? This will directly affect just how technical an engineering leader you are looking for.
If you have lost some engineers in the recent past, their exit interviews can be a rich source of the sorts of issues you will need the new leader to address.
Avoid Biases, Consider Options
There are a long list of possible cognitive biases which may subconsciously steer you toward irrational choices. Avoid these as much you can by keeping yourself open to various possibilities.
A common bias for folks with engineering backgrounds is the tendency to favor candidates with strong, current engineering experience over those with excellent leadership/management skills. Unless you are specifically looking for someone to lead your technical efforts, think carefully about just how much coding and systems design you really need from a leader. Early on this will be useful, but as you scale, your team will suffer without a strong leader/manager. At some point you need to let your engineers handle the engineering.
More senior candidates bring deeper experience and usually lower risk. They are also likely to have higher expectations. Ensure that their experience fits your company and that the role will meet their needs. Ask them directly about this; experienced folks should be able to tell you (from their perspective) the pros and cons of coming onboard. A great fit needs to work for both the company and the candidate.
Also consider qualified but more junior candidates who are hungry for a leadership challenge and will genuinely appreciate the opportunity. Ensure that they have relevant experience and a good knowledge base to begin with, and make clear to them in what ways they are expected to learn and grow. If the growth of the engineering team is gradual, you might be able to develop a “diamond in the rough” this way.
Critically, find a great personality fit. Spend some quality time in conversation with the candidate to assess both their personality and their “people skills.” Ask the candidate how they have handled difficult situations, get specific examples, and dig into them. Ideally a candidate can talk about the pros and cons of multiple approaches, takes action when required, yet exhibits compassion when they do so. An honest person must be able to defend an opinion even when he or she knows you might disagree—push back a little to see how the candidate responds. Do not fall for the slick talker who sounds great but lacks authenticity. When you near the point of hiring someone, reach out to references and probe them on any questions raised, or areas of concern.
Your First Engineering Leader
The process of finding the right engineering leader presents challenges. If you take some time to figure out your needs, prepare appropriate questions, and run effective interviews, the process won’t necessarily be easy, but it has a better chance of being successful.