I have recently had a number of conversations with friends who are on the prowl for new roles given that we are coming out of the end-of-the-year review cycle. I could not help but notice there was a pattern to some of the questions and responses. As a result, and to help prepare you for those kinds of conversations, today I am going to talk about what someone looks for when they are interviewing an engineering leader.
When I am interviewing someone to join my organization I have a standard set of questions that I use. It turns out that I am not alone in this. Each of these questions is designed to tell me something about the candidate. I have seen candidates who realize they do not have a good answer for some of my questions. That is okay. Not having a perfect answer to all of my questions does not disqualify you from your candidacy for the role—it tells me how much work we need to do together to get you to address any gaps that you have to be really successful if everything else is in alignment.
So let’s start going over them.
How many people have you managed?
This question has two parts. I deliberately leave it as a one-part question, to see if they understand it is a two-part question. I want to know how many people someone has managed directly, and how many people they have managed indirectly. If someone supplies the answer in that form, that makes it clear to me they understand multiple levels of management and have participated in it. If you have managed a team of 30 people through 4 direct reports, that is very different from managing a team of 7 people who are all direct reports.
How many managers have you managed?
This is a question that flows naturally from the previous question. I want to know what your experience is at managing managers. It might sound silly but if you have more than 10 people in your organization and you are not breaking that up into groups, that gives me a lot of things to think about. Either someone in your leadership is not setting you up for success, or you are having some kind of other problem. I want to understand what that is. Managing managers is a very difficult skill to master. You have to have the right amount of trust in people to let them make choices, even if they are not well thought out, in order to see the outcomes and adapt to them.
How many managers have you created?
This is really what I want to see in a successful engineering leader. Have you successfully created an engineering leader or manager? Taking someone from being a rank and file individual contributor role and retraining them to learn the skills to manage or lead people is an important professional transition to make. I used to do this in previous companies instinctually. When I was at Zynga, I wrote down all of the steps I took with new first time managers and we turned it into a multi-week conversational boot camp.
How many managers have you promoted?
This is another logical extension from the previous question. Not only do I need to know that you can manage people successfully and transform them from individual contributors into managers or leaders, but can you also convince the rest of the organization that they are growing well enough to get promoted?
Promoting managers is a sign of having a growth mindset. I have seen far too many leaders who create an organization that delivers to the company at the cost of slowing or inhibiting the career goals of its anchors. I do my utmost to take my direct reports on any team and open the kimono to them about my worries and my goals so I can prepare them for the day they transcend their current role and take over a role at my level.
Have you ever had to fire anyone before?
I hope this question does not seem odd to you. Management is mostly about how you handle the extreme cases on your team. What do you do to encourage and grow your top performers? Also, how do you handle people who are performing poorly or participating in incurable, destructive behavior?
This is a horrible skill to have to learn and it is time consuming to teach to people. I do like to make sure all of my managers have had conversations about what this process looks like from start to finish before they ever find themselves in need of having to terminate an employee.
What time frame is suitable for handling a struggling employee?
Every person and every company has different rules for handling how employees struggle. Sometimes people are not performing well. Sometimes people are breaking things for everyone around them. There are very few things that people do that breach trust so completely that it requires an immediate termination, but it does happen. How many times do you try to help someone before it is past the point of trying again? There is no clear answer here. I have done my best to give people three strikes except in extreme situations.
What is the largest production issue you have ever had to manage?
This one comes slightly out of left field and might be more suitable for producers and product managers than engineering managers. Sometimes you learn something interesting based on how they define “largest”. Are people concerned about the volume of users affected? Are people concerned about the cost of an issue? Are people worried that there was a loss of profit? I am more looking for how they framed the term “largest” than anything else here. I want to know what their default behavior takes them to for measuring the impact of a crisis.
Describe the best person you have ever managed.
I am very clear in asking that I do not necessarily want this person’s name, but I want to know why they were the best person that you managed. I listen carefully for the terms they use to describe them. Quite often people try to give this one a pass, or sometimes even want to talk about multiple people. I insist they narrow it down to one person and tell me the most interesting things they can.
Where is the best person who ever worked for you now?
This is a follow up to the previous question and I will state that people react viscerally to this question if they do not have an answer.
I still keep in touch with many amazing people I have worked with. If you take anything away from this article, please set up a 30-minute meeting to reconnect with someone you really enjoyed working with.
There is an old saying “the devil you know is better than the devil you do not know”. I feel this is true. I am constantly hiring new people and adding people to a large and growing pool of people I would love to work with again.
One of the big things I look for is people to bring their existing network power as managers and leaders as a force multiplier to my own problems. This happens less than you would expect. I do my best to help promote my current employer to people I love and respect, and I try my best to find new roles for those people when they need them even if my company is not currently hiring for their specialty.
A lot of people do not value their existing network power as much as they should. I will often ask this question and it will create a momentary panic in a candidate when they realize they do not know where the best person that worked for them is today. That is not the goal of this question. If you find yourself asking this question and catching someone off guard, I recommend changing the subject and talking about something unrelated for a few moments to give them a chance to recollect their thoughts and continue.
Describe the worst person who has ever worked for you.
Similarly to the previous question, I am looking specifically for the attributes that made this person the worst person. Naturally, I do not follow up and ask where they are now.
Tell me about your proudest professional accomplishment.
After putting someone through the ringer on management questions, I generally toss them a softball question to let them bring it all home. If they need a few moments to think about this I will tell them my own proudest moment story to give them something to think about.
What questions do you have for me?
Finally, I try to give the candidate ample time to ask me questions. For a leadership role I generally expect questions. If there are no questions I will ask why not. In the past I was recommended to roles where my friends are working. I have stated that as a reason. “I was recommended to this role by a trusted friend and I have no questions accordingly.”
You might note from these questions that I am not asking a lot of architecture or problem solving questions. I typically partner up with someone else to probe domain-specific knowledge. These questions help me assess whether or not I have an engineering leader who can manage people, or if they are more focused on developing their individual technical leadership skills. There are a handful of candidates who excel in both areas of career progression (technical leadership vs people management) and I want to make sure that I have a full picture of what their experience is and where they can go. Sometimes I will find people who have not yet managed managers, but want to add that to their skill set. If that does not work out I want to make sure I have a different role to offer them in case we are not succeeding together.
When I am on the receiving end of this interview, I will note the shape of the questions I am asked because it will tell me about the problems I am being hired to solve, or at least about the perception of what those problems are by the people doing the interview.
I set up all of my hiring processes with a standard pool of questions to break that pattern. I strongly recommend making a standardized hiring process to every hiring manager I speak to. Especially if you are hiring for a large number of roles.
So now you know just about everything I think I know about interviewing managers.
I hope you find this interesting or useful. I have recently had multiple conversations on career direction with former peers whom I respect greatly. If you have questions or concerns about where you are in your career, I am happy to listen to them and see if I can give you perspective on them.
As always blah blah blah social, blah blah blah gratitude.
I look forward to writing again next week!
