Interview Your Founders
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When it comes to startups, Silicon Valley is the home to fantastic success stories as well as catastrophic failures. As a candidate interviewing at these companies, it can be difficult to see through the hype and assess which companies actually stand out in terms of fundamentals and culture. What if you could increase your chances of winning that bet?
You can. The key is to turn the tables and start interviewing the leadership of prospective companies. All too often, candidates fumble with the dreaded “What do you like about working here?” when it’s their turn to speak up in an interview. Think of what you might learn if you instead asked a few more incisive questions:
Does the company have a clear mission unifying its work?
How many people have left, and what happened?
What is the role and structure of management?
What problems do you encounter when trying to collect revenue from customers?
My job search last year got me interacting more with founders, and I worked with my mentors to design a model for the type of leadership I wanted to work with. Below are some of the assessments we came up with to gauge how successful a startup might be — and more importantly — how happy I might be working for them.
Founder DNA
Management styles tend to evolve as a result of past experiences. To start, I tried to dig into what the a founder’s values were and how they were formed. A few questions that helped here were:
What companies have they worked for before?
What aspects of that culture do they bring with them?
What didn’t work?
Have they started a company before?
It’s important to note with these questions that you’re looking for how the founder has grown, not for a specific pattern or experience. Some people will learn great management through mentors, others will learn by observing repeated failures and learning from those mistakes.
Hiring Hygiene
When you’re meeting a new team, you get only a surface level glimpse at the team as it exists now. Your team will ultimately be made up of many more who made it through the interview process. It’s critical to assess that process and understand what it’s selecting for. To that end, I asked:
What is your hiring philosophy?
How is the company targeting candidates at varying experience levels?
What are you doing to develop a diverse work environment?
How do you ensure that you have enough mentorship capacity for new hires?
The interview process is something you’ll experience firsthand, so you can also collect data from your own experience here. After my onsite interviews, I asked myself a few follow-ups:
Does the company’s hiring process seem intentional?
Did the questions they asked allow me to convey my experience and value?
Were the questions representative of a realistic job scenario?
Would the people I’ve loved working with pass this interview process?
Would people who are difficult to work with be weeded out?
The Epitaph
One of the most telling signs of company culture is retention. Some companies have attrition rates are in the single digit percentages, others are trapped in a revolving door of departures. Ask the founders:
How many people have left, and what happened?
As with all of these questions, the details of the explanation matter here. “Our best engineer left” might be damning or perfectly healthy depending on the circumstances. Some departure stories I heard were rooted in mis-management, while other employees left because they had formed a mega-profitable side business. It’s worth pushing for the details!
Humility
Humble leaders will be better able to delegate and trust in others, and will be more forthcoming with admitting their mistakes and correcting course.
In my search, this one worked well for bringing out humility (or lack thereof) was:
I’m also interviewing at <X> and <Y> what do you think about those companies?
Many different questions will work here. Ideally you’ll ask something that provides a choice between answering defensively or with humility. A great response in that scenario sounds transparent and modest; a bad one sounds like a blame, attack, or cover-up.
Growth Mindset
Another trait that goes hand-in-hand with humility is growth mindset. Founders who adopt a growth mindset believe that intelligence and talent can be developed through hard work. They’ll view effort as a prerequisite to success and will leverage that belief to find creative solutions when tough problems arise. There’s even evidence that their brains are more capable of detecting mistakes. On the flip-side, those with a fixed mindset will believe that their inherent talent will be enough to propel them to success (spoiler: it won’t be).
A couple of simple questions helped to get at this one:
What’s the most important thing you’ve learned lately?
What assumptions have you been wrong about?
Management Style
Another broad category to look at is management style. To kick the tires here, ask:
What is the role and structure of management?
How are meetings run?
How is prioritization done?
How are project assignments decided?
I wanted to see evidence that the founders were building an intentional structure to identify priorities and align people within the business to work on them. I also wanted to know that management was capable of providing people with clear goals. Doing so is critical in a startup where you have many more problems than resources.
It’s also important that individual contributors play a part in prioritization. This ensures that people work on projects that are aligned with their interests and growth paths. In turn, they will produce more and stay longer.
Business Viability
At the risk of stating the obvious, I’ll say that you should asses whether the business idea this company is solving is a viable one that can sustain itself. A few that I like to ask here:
Why did you start this company?
What are the limits of the firm?
Does the company have a clear mission unifying its work?
What is the path from their idea to a concrete solution that people will pay for?
Are customers using it?
The two general ideas I care about here are (1) is the idea viable and (2) is the leadership team focused enough to realize it? You want leave the discussion convinced of both.
It’s also critical to have company-wide alignment on some of these issues. The question about unifying vision is a great one to ask everyone that you interview with. If leadership and individual contributors have different answers about company vision, it may be an indicator of poor alignment.
Monetization
While you’re on the subject of business viability, it’s important to understand how the business is positioning itself to monetize. A few that I think make sense here are:
What is the size of the market you’re operating in?
What is the gross margin on your product?
What is your path to profitability?
What fee structure do you use to charge customers?
What problems do you encounter when trying to collect revenue from customers?
Good founders will be able to provide a significant level of detail and a concrete plan around monetizing that makes sense within their industry. Bad ones will have a vague plan without figures and data to back it up.
Competition
Every business needs to maintain awareness of its competitors and position itself accordingly. A few starters here:
Who are your competitors?
What value do you offer over them?
What advantages do they have over you?
How do you maintain your advantage?
Good founders will be aware of their competitors and acknowledge the risk they pose. They’ll also give continual thought and attention to maintaining their positioning.
For me personally, this one exposed a few companies that insisted they had no competitors. A few minutes of Googling was often enough to uncover several. Don’t forget to do your own investigation!
Fundraising Hygiene
How a founder goes about raising capital provides interesting insight into their mindset as well as the sustainability of their business. This category gets a bit technical, so it’s worth learning about some of the dirty practices that can be employed in fundraising. Here, I’d ask:
How are you protecting your business and employees with your fundraising practices?
What terms are preferred investors being given?
Are you employing multiple liquidation preferences, dividends, or ratchets?
Good founders raise funds thoughtfully and seek out terms which will allow them to protect the business and reward key performers. Additionally, their ability to raise on favorable terms indicates that investors see value in the business and promise in the management team.
Surprises
Even after a deep dive into all of the facets above, you’re still going to be in store for surprises when you join a company and get exposed to the less rosy internals of the company. One of my mentors was interviewing for management positions and asked:
What will I be surprised by when I join?
Some founders were candid to a fault. In her case, one of the answers was “We’re too afraid to fire people and want someone else to do it”. Eek!
Backchannels
While founders or company leadership are the best people to ask these questions, it’s worth noting that this is their business and their answers may be biased accordingly. The stories you hear from them may sound different told from the perspective of a current or former employee.
I’d recommend working through some of the same questions by asking the same questions to other employees within the company, or to former coworkers. This will not only identify disparities and weaknesses, but will also help to build confidence as other sources will provide additional support for a founder’s strengths.
These are a few of the facets I used when getting a feel for founders or leadership, but I’m still developing and questioning my methodology. What questions have provided significant insight for you?
Thank you to the mentors who helped me think through these topics and shared questions. Credit for anything useful belongs to them!
