Ask the CTO: How do I hire managers?

The problem: Hiring managers is impossible!

I am growing my team rapidly and the time has come for me to start adding more management structure. Everyone says that promoting from within is the best way to do things—I tend to agree. However, I’ve had managers hired above me who were just terrible, and we’ve already had one person come in and quickly flame out. But I just don’t have enough people on my team who are interested in management and capable of doing the job. I don’t want to force people into management because I know that doesn’t work well. I’ve got to hire.

So, I want to do the best I can hiring people into management roles, but how? What should I be looking for when I hire managers?

The solution: Think about what you’re looking for

Hiring engineering managers is hard. And worse, the technology industry does not do a very good job of it. I believe this is because of two fundamental problems:

1. We don’t really have a clear idea of what we expect managers to do. Managers are expected to be unicorns. They are first interviewed with a bunch of technical questions, and then their actual ability to lead teams is assessed. A lot of excuses are made for people who are technically talented but may not have the management skills needed.
2. People are coerced into management jobs who don’t want to be managers. And, sadly, they aren’t trained in the skills needed. As I said in my first column, management is a job, not just a few more duties on top of technical work.

However, if you look at these problems from a different perspective, what you’ll find is that hiring must be done holistically by considering every hire carefully. Consider hiring people with management potential rather than just holding out for management experience. There are many people out there who are looking for the opportunity to go into management as part of their career path, which means they often turn out to be good, thoughtful managers.

If your goal is to build a culture where you can promote from within, think about how management potential manifests when you’re hiring senior engineers. Look for folks who express an interest in becoming tech leads or managers. These candidates will build up that talent pool within your organization.

Practical advice: Create specific questions and tasks for management candidates

One strategy is to look for incredibly smart tech lead-level developers who may have limited management experience and put them in the management role. You’ll need to spend a good deal of time focused on screening for management potential.

The other strategy is to hire experienced managers. For this, you’re going to want to get a sense of the candidate’s management style and philosophy, and make sure s/he is technical enough for the team’s needs.

Screening for potential is different than screening for experience. Consider these two different approaches once you’ve decided how to hire.

Questions for tech leads with management potential

Tell me about a project where you have acted as the tech lead. What was your role like, as tech lead? What were things you did that were different from the rest of the team? How did you ensure that the project was successful?

What you are looking for: A candidate should answer with more than just “I designed the architecture, chose the libraries, and wrote the most technically challenging pieces of the code.” She should have taken an active role in the project management, even if there was another person explicitly or implicitly in that role. She should have contributed to predicting problems with the delivery and working with the people on the team or cross-team to ensure success.

When you bring a new team member onto your team, what kinds of things do you personally do as part of their onboarding? Have you ever been a mentor to a new hire or intern? What was that like, what did you learn from it?

What you are looking for: A candidate who is actively engaged in the work of bringing on new people and thoughtful about making that process better. She should respect the work of mentoring, and not be someone who’s trying to shed human interactions quickly to get back to code.

Tell me about some things you have done to make the process of writing or delivering code in your organization better.

What you are looking for: The candidate should provide some strong examples of observing process, people, or systems problems and what she did to suggest improvements.

Questions for hiring experienced manager for tech teams

How do you build a diverse candidate pipeline?

It’s common to ask about hiring, but I would recommend asking about a candidate pipeline specifically, because it shows off candidates who are committed to having wide networks. Many people will simply shrug and say that they expect the recruiting team to bring in candidates. The best managers are capable of bringing in their own candidates, even at big companies. If you need someone to grow a team and he can’t answer questions about how he contributes to finding and recruiting talent, that should be noted as a risk. Furthermore, if you really do care about diversity and the candidate does not engage with that question, flag it.

How do you spend your day? What is your meeting schedule? Who do you spend your time with? How hands-on do you like to be in your management?

This type of question is key to figuring out if a candidate’s style is going to work with your organization. If you expect someone who will be very hands-on and the candidate is used to spending all day in meetings, it may not work out well. Managers often succeed or fail based on how well they fit in with the culture and style of the organization, so spend quality time getting a sense of their style and habits.

What do you believe the job of a manager is? What are the skills and qualities that make a great manager?

A candidate who cares about management as an important job is going to have some thoughts about these questions. They will have experiences to draw on, challenges that they have faced as they’ve grown as a manager, practices they believe lead to team success. This is a critical position of influence, and you want someone who has an idea of what it means to be great in the role.

How do you set goals? How do you evaluate success? Tell me about a project you managed that was successful. Tell me about a project you managed that was a failure. Why did each project succeed and fail? Or: Describe a problem you experienced with a hard-to-find solution. How did you decide on a solution? What did you do once you decided on the solution?

These two sets of questions help you understand how the candidate sees the technical, execution, and social elements of projects. How did the candidate get help from people outside of her team? Did she carefully consider the process of getting buy-in on projects that went beyond her area of ownership? Think about how she solicited technical input, balanced it with execution, and learned from failure.

When it comes to technically screening experienced management candidates, I prefer to focus on high-level questions about systems. One exercise is to have candidates sit with some engineers and mediate a technical disagreement or decision. What kinds of questions does he ask to help the team come to a decision? Is he capable of digging in even when he isn’t familiar with the technologies at hand?

Another exercise is role playing. Set up a scenario that might happen, for example, an employee is unhappy that she didn’t get promoted. Provide an overview to the candidate and give the interviewer some details that may include information that the manager doesn’t necessarily know. Have a third party observe the interaction and then at the end of the role play have all three participants talk about what went well and didn’t. (Credit to Marc Hedlund for this idea!)

Wrap-up

When hiring managers, particularly managers coming in from heavily hands-on technical roles, you will likely find (and maybe even intentionally seek out) someone who will not only manage people, but drive technical decision-making. Make sure that any people currently providing technical direction are aligned on that front with the candidate. If the candidate is gung-ho about functional programming and microservices but your team is more technically conservative, you might end up with a manager who wants to make big technical changes that you don’t agree with. Seek out technical alignment, but remember that this is a management job. It’s great if the team is excited about working for this person because they feel that they will learn something, but don’t just hire a manager because people are excited about her technical chops.

Overall, when screening for potential, look for signs of stepping up, caring about the people on the team, and thoughtfulness about the processes. And be prepared to train the candidate. This person will need help, so be prepared to assess where their gaps are and ask them what kind of training would be helpful. Whether it is formal training, a lot of mentorship from you, or a mix of both, no one is born knowing how to manage. I think it is worth sometimes taking a risk—I’m glad someone did that for me once—but your new manager will struggle if she has to do it all alone.

When hiring for experience, look for cultural alignment, engagement with the work of management as a discipline, and thoughtfulness about the role within the larger organization.

In either case, you should also be looking for excellent communication skills and everyone who interviews the person should feel pretty comfortable with the idea of working for them. However, be mindful of potential bias here. The best managers are often overlooked because they don’t pattern match to certain characteristics, whether they are “tall and male” or “have a forceful personality” or whatever. Talk to the team before the interview and give them examples of great managers who sit outside of those stereotypes to reset their stereotype bias a little bit.

Mis-hiring managers tends to come from overvaluing technical skills and pattern matching on “what a leader looks like,” and the failure mode is managers who just don’t deliver coherent teams and/or can’t deliver projects effectively. If you’re really unlucky, you hire a manager who is more focused on their own success than the success of the company and the team. Never ever hire a person you feel is overly ego-driven.