What to ask when interviewing for a VPE position?
What to ask when interviewing for a VPE position?
Remember, an interview is a two-way street!
In my previous post, I wrote about what to expect as a candidate during an interview for a VP of Engineering position. This post covers what you, as a candidate, should be asking during the interview.
An interview is a two-way street, the company is trying to assess if you are a good fit and similarly, you are also trying to assess if the company and position are aligned with your goals. Much like the previous article, the below is based on my own experience.
There are two areas I try to assess during an interview for a VPE position. The first is specific to the job. The second is more general to the company. The intent of my assessment is to answer two questions. First, Is the job aligned with my skills and goals? Second, is this a company I want to work at?
Job specific questions
The VP of Engineering job is entirely dependent on the stage of the company. A pre-seed startup seeking a VP of Engineering, which is highly unlikely, will have very different expectations on the role versus a pre-IPO startup. Therefore, one of the more important aspects during the interview, and arguably before you start interviewing, is to level-set on the expectations for the role. I mentioned in the previous article being asked the following question by the CTO of a startup I was interviewing at:
If someone on your team were to guess what it is you do on any given day, what would they say?
The intent of this question is to find the commonality between what the CTO, and the company needs from the VPE and what I am able to offer. You should ask the inverse of this question. I ask the following question to the CTO, CPO and CEO:
Whatproblemsdo you want to solve by hiring me
I recommend that you ask this question during every one of these interviews. The ideal outcome is that they all express the same motivations for wanting to fill the role, and that you are able and wanting to do what they have in mind. There have been numerous cases, in which I discovered disparate reasons for making this hire. This in of itself isn’t really an issue, except if the motivations of each are so divergent that it signals misalignment at the topmost levels of the company. I also recommend you ask the same question to Board members, if they are part of your interview cycle.
One other important way for you to explore the needs for this role is through members of the engineering team. It might be unlikely that you are interviewed by members of the team, which is why I always request that I interview a few members of the team. I do so, to understand what the and the team at large want out of this role. Again, you’d be surprised at the disconnect between what a CEO wants from this role versus what the engineers need. Below are some of the questions that I ask often times to more than one person on the team
What are the challenges facing you and the team?
Describe a day in your life, what do you spend your time on?
What areas should I focus on to help you and the team?
A few other questions I tend to ask the CTO/CPO and CEO are below:
Describe the ideal candidate for this role? I am seeking to understand fit
Why hasn’t this role been filled from within?
Your goal during these interviews is to fill in the Venn diagram below, and hopefully find that the answer to all three questions occurs at the intersection.
That means that you should be going into the interview knowing what your own motivations for the role are and assessing whether this role can help you realize those. You should also know what you are good at, which should be part of your own preparation for the interview.
There are also more tactical questions, which I outline below, which I ask. I ask them to understand more about the day to day workings of the engineering team and to discover some of the interactions engineers have with other teams.
How do you plan and prioritize work?
How do you make the case for engineering specific work? Examples: testing infrastructure, tech debt/refactoring, tooling.
How do you release software and how often?
How do you handle customer escalations?
How many engineers left the team last year (%) and why?
Company specific questions
There’s a significant opportunity cost and risk associated with joining a startup. The questions below are my attempt to understand the risk profile of the startup and evaluate whether I am willing to take this risk. There’s no way for me to fully quantify the risk, but my intent is to understand intrinsic risk, meaning risk that the startup is in control of. The extrinsic, or more generally market risk, is something I also try to understand mainly by focusing on the market the startup competes in, its growth and competitive dynamics. However, there are far more parameters than the ones I mention. Take interest rates as a recent example!
The questions I ask cover the financial health and equity structure of the company, the sales productivity and competitive landscape and lastly the company goals and values. I summarize a few of those below.
Finance
The most common way to get answers to some of these questions if from members of the leadership team. The CEO most definitely should be able to answer them all. If I have one major red flag it is no wanting to answer questions related to the capital structure of the firm. A company trying to deflect questions on valuation or number of outstanding shares is simply trying to obfuscate your compensation. I understand not wanting to divulge this information at the beginning of the interview process, but you must have this information at the offer stage. Otherwise you simply will be unable to value your offer and assess the risk you are about to take.
Total number of outstanding shares (common + preferred)
Pre & post money valuation in last round and latest 409a
Do preferred shareholders have liquidation preferences and/or participation rights?
Monthly cash burn and cash runway
Last year ARR, target for this year and where are you relative to plan.
Sales & Product
The questions below can also be answered by the CEO, CRO, CTO or CPO. My goal is to understand the competitive landscape facing the startup. I am also eager to know if the sales team is successful. A sales team that is unable to hit their targets signals all sorts of problems. These could be lack of true product market fit, a highly competitive landscape, quality or some others intrinsic to the sales team.
Why do you win? Why lose?
Who are your competitors and what is your value prop relative to them?
% of sales reps that hit their quota in the last 2 quarters.
What’s your wishlist from a product and engineering perspective
Company goals and culture
These questions help me understand what the company cares about, both in terms of people values and its goals and aspirations over the next year. The value and people related questions are of particular important to me. Joining a startup can be incredibly rewarding, but it is also arduous. The way to tackle the hard times is to be surrounded by people who share similar values to yours. Hence, the importance of asking these questions.
How do you do company planning? Quarterly? OKRs...etc
What are the goals for this fiscal year
What are the values you want universal across your employees
Why do you lose employees?
If you could solve one problem at the company, what would be it
Why will this company fail? I like asking this one to Board members. Try it out!
I start the interview process with a Google doc outlining all the questions I want answered, yet know that it will be unlikely I will get to all of them. Therefore, I prioritize them, according to what I care most about. I recommend that you do the same.
Spending time preparing for what you want to discover during the interview and prioritizing what is important to you, will ultimately help you land a job you can succeed at. Good luck!
This post is a part of a series that goes into the details of the VPE position and interview structure. Other relevant posts are