How do you interview a VP of Engineering?

25 questions I’ve been asked in previous interviews

One of my interviewing habits is to write down questions I was asked alongside my responses to them. I do this as a way to self debrief and reflect on how well I think I did. Over the years, I have collected quite a few questions from interviewing for VP of Engineering positions. This post will offer some insight into some of the more salient questions. However, before diving into the questions, it might be worth describing the structure of a VP of Engineering interview. The following is entirely based on my personal experience and is not necessarily indicative of a trend or pattern.

In my experience, the structure of a VPE interview is ~60 minute sessions with each of the following: CEO, CTO, CPO, Head of People and either the Head of Sales or Marketing. I have also been interviewed numerous times by members of the Board. Additionally, most of my interviews included me presenting to a panel which is typically the entire leadership team. The panel interview is often-times me presenting about one or more topics shared ahead of time.

The below outlines some of the common or interesting questions that I have encountered. I group them by the persona asking them. While I do not make an attempt to answer the questions, I will try and dive a bit deeper into one question per section.

CTO & CPO

These two interviews are arguably the most important to do well on. As an incoming VPE you are expected to work extremely close to the CTO and the CPO. Additionally, it has been my experience that the CTO is almost always a co-founder and would have been up to the point of hiring a VPE managing the engineering team. As such, they have a very strong interest in ensuring that the right person takes over the reins from them.

If someone on your team were to guess what it is you do on any given day, what would they say?
How do you structure engineering teams? How does PM fit into this structure?
What is the reasonable interaction between PM and Engineering? What do you need from a PM organization?
What are some of the friction points between Product & Engineering and how do you handle them?
What is your biggest accomplishment leading an engineering team?

The “guess what Karim is doing” is a very interesting question. It’s one I was asked once, and to be frank it stomped me (I did get the job). It’s not that I do not know what it is I do, it is that I do not know what the interviewer, in this case the CTO is trying to assess from my response. It turns out that they were trying to find out the overlap between what I do versus what the team needs. For example, had I mentioned things like design reviews, code reviews and coding whilst the team needs more of a manager persona, then that would be indicative of a poor fit.

I won’t summarize my answer here, but it’s not that much different than what I outline in my article on “ What does VP of Engineering do “

CEO

CEO interviews tended to be either at the very beginning of the process or the very end. If they are at the very end, they’ll usually spend more time talking about the business and trying to close you. CEOs are almost always interested in hearing your story, what led you to them today.

How do you increase your team’s throughput?
Why did they ultimately leave their company for the next role?
If I called your previous CEO, how would they describe you
Tell me your story?

I’ve been asked the “throughput” question twice, both times using the exact word. I’ll be honest, I dislike the question. Not because I cannot answer it, but because it offers a narrow view of an engineering team; a conveyor belt of features that should move as fast as possible. While I do understand the intent behind the question, the word throughput triggers me. That could also be a result of ~7yrs working in the file-systems space.

My one advice when answering this question is to ask clarifying questions before responding. A CEO asking this question is concerned about the velocity of features coming out of the engineering team; they are observing a symptom not a root cause. Ask them why they think the team isn’t performing well. The response they give might offer you a root cause or at least provide you with a more structured and specific answer versus a very open ended one. For example, when I dug deeper once I found out that the “throughput” was slow because the team would deliver the wrong features, a function of poor scoping and problem definition. So, before you offer your Kanban boards or your agile processes and your exceptional hiring skills, just dig a bit deeper to get to the root cause.

Head of People

The Head of People interview is, unsurprisingly, going to focus on your people management skills. One very common topic is that of hiring, especially for an incoming VPE at a series-A or B startup. You are expected to scale the team, which is a function of hiring and building people programs in support of this hiring.

How do you scale an engineering team?
Have you fired employees, why and how
What people programs did you put in place as the team grew? How?
What’s your weakness? What’s your biggest failure

There’s no right way to answer the scaling the team question, but there’s a wrong one. The Head of People is looking to assess if you are a good partner for her team, meaning will you be a true partner with the recruiting team or simply offload all the work to them. A good answer should cover topics like structuring a repeatable and objective interview process, identifying sources of candidates (industry, referrals, college) and guiding the recruiting team on how to source for good candidates. All of these activities are ones the VPE needs to lead. Remember scaling a team is >> interviewing.

Head of Sales/Marketing

I’ve had interviews with heads of sales or marketing 50% of the time. They are rare, but I found them very insightful. Most of the insights were me asking questions, which I will share in a later post.

How does engineering support sales?
Walk me through a challenging customer interaction. What happened and what did you do

It should come as no surprise that the Head of Sales will be mighty vested in how you can help her team sell more. The main avenue for engineering helping sales win deals is handling one-off feature requests. I wrote about this topic in the “ Feature deal-making “ article. In the early stages of a startup, it is not unexpected to encounter a customer willing to buy your product only if a certain feature(s) are implemented. In comes the VPE to help make this happen.

Panel interview

The intent of the panel interview is to assess your written and verbal communication skills. I’ve had panel interviews in almost all my VPE positions I pursued, so it’s a pretty common format. As a VPE you are expected to possess reasonable written and communication skills. You might be asked to present at a conference, your team, to customers, to share written context with your team and so on. All of these require a good command of written and verbal communication.

The questions are always shared ahead of the time and the delivery is either a written document of a presentation. Regardless of the format, you will always be required to present your thoughts to the panel, which as I mentioned will be the company’s leadership team. Regardless of the format, the topic that you will be asked to write on could be somewhat vague (see the question I highlighted below). You will have to make reasonable assumptions and proceed from those. Not only is the intent of the panel interview to assess your written and communication skills, but it’s an opportunity for the company to assess your thinking. Can you make reasonable assumptions and structure arguments of hypotheses based on those?

Please write a document of significance showing your ability to manage and communicate upwards, e.g. something that communicates a new or key initiative to the CTO; (e.g., communication, ppt, xls, or word doc).
What is the most inventive or innovative thing you’ve done? It doesn’t have to be something that’s patented. It could be a process change, product idea, a new metric or customer facing interface — something that was your idea. It cannot be anything your current or previous employer would deem confidential information. Please provide us with context to understand the invention/innovation. What problem were you seeking to solve? Why was it important? What was the result? Why or how did it make a difference and change things?
Describe what the components are and how you would go about developing a 30–60–90 day plan at The Company.
Given what you know about current Company’s technology and scale, present a technology organization plan for a team that is double in size, from x to 2x.
Your team is unable to deliver features on time and is suffering from poor morale. What could be going on?

I highlighted the “team unable to deliver” question because the format was quite unusual. The question was shared with me at the beginning of the panel interview and I was given 30 minutes to construct my response. I came up with a few hypotheses and presented them to the panel. During my presentation, the panel would share relevant information, in response to some of my hypotheses. The whole process was similar to “Chose Your Own Adventure “ books. I recall alluding to poor scoping of projects, and was given additional information. It turns out that the CTO has a habit of parachuting in at the last minute and changing project requirements. This can definitely demotivate a team and introduce risk on their ability to deliver features. By the way, the CTO was part of the panel and fully acknowledged that he does that and needs to change that behavior.

Board Members

I’ve been interviewed by members of the Board 50% of the time, once with the entire board members (one at a time), which was fun. Interviews with members of the BoD occur at the very end of the process. The good news is, if you made it to the BoD then the company is leaning towards hiring you. The BoD are typically the investors in the company and have one main interest: can you help make the company successful, and hence provide a meaningful return on their investment. The VPE plays an incredibly critical role at a startup, hence they have a very strong vested interest to ensure that you are the right person.

What’s interesting to you about this company? What do you think you can add to the team?
What are the challenges in scaling a company from 0–20M in revenue/ARR?
What are some of the challenges you’ve seen when acquiring enterprise customers?
We’ve had quality issues, what do you do?
What can you do to accelerate product delivery?

I highlighted the “quality” question because it was a bit unusual to be asked this from a member of the Board. Keep in mind that a Board typically meets every 12 weeks and will get a summarized view of the more critical aspects of the day to day operations of the company. Therefore, a board member asking you about quality implies that the issue is critical enough to be shared by the company with their Board. While not exactly a red flag, it is one that should give you slight concern. More worrying you will not get a whole lot of details from the board member, they won’t know why quality is poor. They know that it is, and hope that you can fix this problem!

I have a much longer set of questions, some I encountered and others not. I compiled those all in this public document here. In the next article, I will cover what a VPE should ask and try and discover during the interview process. Remember, an interview is a bi-directional assessment!

Finally, this post is part of a series all concerned with the VPE role. You might find these other posts also useful