Last Updated: June 1, 2016

As someone that has hired and been hired, there’s one point during the interview process that is crucial. It’s the awkward, “Do you have any questions for me?” from the interviewer.

Too many times I’ve seen candidates not take full advantage of this question. When I’ve been in the position as the interviewee, I’ve also flubbed this opportunity. Really, the entire interview should be centered around this question.

So for my own edification, I’ve compiled the list of things I forget to ask. Each of these questions is designed to cut to the core of what makes the company tick. I’ll do my best to keep this list updated from time to time.

The types of answers you’ll get to each of these questions will be very different, depending on the company that you are looking to join. The founders of the company might be figuring some of the questions out as they go. That’s okay. The important part here is to kick off the discussion to answer: Can I get along with these folks?

High Level






High Level

What is the company mission?

Earlier in my career, I thought mission statements were a waste of time. Why would someone spend so much effort creating something that sounds like marketing?

At this point, having a mission statement is incredibly important. The mission is why every single employee schleps to work each day.

For younger companies that haven’t codified a mission statement yet, just ask the founders for the first sentence of their VC pitch. “Widgetly is going to improve how widgets are bought and sold around the world.”

If the company has a mission that they can articulate, great. Now for the hard part: is everyone a believer?

What are the company’s values?


How does the company decide what gets built?

There’s no right way to build a product. After having many, many conversations around this topic, it appears every company does things a bit differently.

One of the more important questions that leadership needs to answer is how they decide what gets built. I’m of the mind that companies live and die by their ability to answer this question. It’s an expensive proposition to build something that no one wants, or that no one wants to pay for.

Where does leadership allow product ideas to originate? How are ideas vetted and challenged, without destroying them in their nascency?

Bonus points if the answer involves something along the lines of “we decide what to build based on constant communication with our customers.”

A good hypothetical to drive to the heart of this question is: If an intern comes up with a great product idea, how will that get built?

Who decides what gets built?

Tangential to deciding what gets built, it’s also important to decide who makes the calls there. Is it the board? Is it the executive committee? Is it the CEO, head of product, or the CTO?

How do you decide how to build something?


Where does an employee go to find out information?

Every company can benefit from an internal wiki of sorts. I’ve seen this come in all shapes in sizes.

This isn’t a requirement, but if a company doesn’t have something that looks like a handbook and they are >10 people, I would categorize that as a company smell. Another thing to look out for: when was it last updated?

What was the last thing that shipped? When was that? How did that process go?

Software companies are defined by what they ship.

The smell you’re looking for here is a high number, like anything above a quarter. Software companies are sharks, if they stop moving they die.

Stay on the lookout for phrases like “burnt out” or “way too long.”

How are the success metrics established?

Even in young companies, being able to measure successes is incredibly important. By setting up goals for a product before it begins, you encourage a certain repeatability in development. This repeatability is incredibly important as the team scales.

What you’re looking for here is clarity in goals. “We are shipping Feature X to decrease churn. We’ll know if we’ve accomplished the goal if monthly churn goes from 8% to 4%.”


What is the financial health of the company?

Nothing kills a buzz quicker than talking about money, but it’s a conversation that you must have.

I’ve hired someone with just a few months of cash left in the bank, and I’ve had friends join companies with mere weeks of cash left in the bank. Weeks! It’s a shitty thing to do, but it unfortunately happens.

The answer you’ll get here will always be “good” or “fine.” So that’s why the next questions are so important, because they get into specifics.

When asking questions about finances, how the questions are answered is just as important as the content of the answers. Do they bristle when asked these questions? Do they refuse to be candid? Do you think there might be something they are hiding?

What’s the burn rate?

This one’s easy, and should be able to be answered by a CEO immediately. If the company is not profitable (it’s almost definitely not if you’re reading this), you need to know how much money the company loses every month.

For an individual, this number will always seem insanely high. Just write it down to come back to later.

If you want to dig a little deeper, ask “How is the burn rate changing month to month?” You’ll be looking for the answer: “It’s decreasing each month” or “It would be decreasing each month were we not bringing on new employees.”

What is the total amount of cash on hand?

This is the second half of the burn rate question, and lets you do some math to figure out an important question: When does the company run out of money?

The smell you’re looking for here is anything less than 6 months. If it’s less than 6 months, you’ll likely hear a “But we’re just about to close a round, so it’s okay.” That answer should be the reddest of flags: the founder doesn’t realize that they can’t hire their way out of a company that’s not working. By the time you’re onboarded and productive, the company will be dead.

When is the drop dead date for the company?

You should already know the answer to this based on the math from the previous two questions. What you’re looking for here is an acute awareness of mortality.

Are there any abnormal financial instruments at play that may cause unexpected swings in valuations, control, or equity? (Warrants, etc.)

Again, an uncomfortable question. In the world of financing, there is not shortage of ways to overcomplicate things.

Just know that you, as an employee, are the last in line when it comes to extracting the wealth that the company creates. The banks, VCs, and founders are all in front of you.

Many folks might declare this as unfair or lopsided. It’s not perfect, but they are the ones that took the most risk to get things to a point where they could have the luxury to hire employees. If this still seems unfair, my best advice would be to start your own thing.

I’ve seen friends think they own 3% of a company, only to have that evaporate.

How does the company make money? If it doesn’t, how will it make money?

Startups that don’t make money are going out of vogue a bit, at least at the time of this writing. There used to be a time where companies would float through the world without a care in the world for bringing in revenue. No, that is not a joke.

But who knows, you might be interviewing for the once-a-decade company that can get by without making money before they turn on the firehose. Know that those companies are so incredibly rare that you’re almost certainly not interviewing at one.

Which teams are actively focused on bringing in more revenue?

The best answer to this question should be “all of them, and here’s how.” A smell here would be a disdainful, “Yeah, we’ve got a few people working on figuring that out.”

Is the company designed to go public, be acquired, or neither?

Every company is a bit different. Some founders just want to build a small team of people they get along with and collect comfortable pay checks. Some people want to try to take a company public, which is generally considered a startup’s greatest success. Some people want to build startups to be acquired by a larger company. Those people are gross.

The important thing here is to have some alignment with your own personal goals. If you were to build a company, what would you want it to be?

If the company were to big acquired tomorrow, which company would that be? Is that company different than who it would ideally be?

This is one of my favorites. The ecosystem can seem to be quite forgiving to young startups. Even those that are objective failures can still secure the “soft landing.” (The soft landings can sometimes not be so soft.)

The interesting part with this question is when the differences come out. It tells you who the company self-identifies with the most, and then asks for a reality check. For a young company, this question can help better identify what type of company the founders are building. “We’d love to join the team at GitHub, but Google is probably the only company out there with enough cash to make our investors happy.”



How is engineering run?

What’s the org chart? Who reports to who? Just get a lay of the land here.

Does the engineering org pass the Joel Test?

You’re looking for a resounding Yes! here, or a commitment to doing so. It’s possible to have a functional software company that does not pass the Joel Test, but not for very long.

How closely do your apps adhere to the Twelve-Factor App? If that isn’t an intention, what was chosen instead and why?

Much like the Joel Test, this question is designed to test the priorities of engineering. I’ve found 12factor to be “good enough” for almost all young companies out there.

If they don’t practice it, ask why and what instead is in its place.

How do engineering tasks get prioritized, tracked, and delivered?

Chances are, the rest of the company hinges on the ability for engineering to deliver the functional components of a service or product in a timely and consistent fashion. Product, support, marketing, sales, and more don’t matter if there is not consistency in engineering tasks getting delivered.

This is also on of those questions worth asking several different engineers to look for consistency.

What is the process of letting customers know when a bug fix has shipped or a feature has landed?

Very few companies close the loop here to let customers know that that bug they reported 2 weeks is now fixed. This action is incredibly important to young companies because it develops a relationship with your customers.

I’ve seen companies hack this with custom Salesforce fields, notes in a GitHub issue and many other ways.


Not every company will have an inside sales team. Sometimes they don’t economically make sense. But if you find yourself joining a startup with a sales team, you want to make sure you trust them to deliver. Your job and the company’s success depends on it.

Can every sales person clearly articulate the value of the product?

This is a great test to see if the company has a functioning sales team. Much of sales is about training new hires.

If you find that members of the sales team don’t have a good understanding of what the product is or what it does, there likely isn’t enough sales leadership or training. This will have one consequence: your sales team won’t be able to close deals consistently.

Does every sales person have a strong knowledge of the market and the market’s nomenclature?


How are sales people trained?

Ask to glance at the training material. You should see something that takes someone from only having a loose understanding of the product to a very strong one.

The sales training process will usually take months.

How are sales people compensated?

Some young companies will get this very wrong in that they will reward activity instead of results. Make sure the systems here are set up to attribute and reward results.


How are disputes on teams resolved?

Sadly, everything is not all sunshine and rainbows in a young company. The stress is often palpable. You have an entire group of people getting paid less than what their worth trying to deliver a product better and faster than they ever have. It’s the exact opposite of easy.

With this question, you’re looking for some discreteness and some consistently. “If two people aren’t getting along for whatever reason, the CEO or team lead sits with the two of them in a wrong until they come to some consensus.”

I’ve seen the inability to resolve heated disputes unnecessarily cost people their jobs.

How are cross-functional disputes resolved?

Inter-personal disputes are bad enough, but sometimes you’ll have entire departments that hate each other. There are many ways of resolving these, but a repeated existence of these makes everyone wonder “Are we on the same team?” If you get the sense that cross-functional squabbles are common, you probably don’t want to work at that company.

What was the last “oh shit” blow up? How was that resolved?


How are people hired?

As you know, there is much more to hiring than simply submitting your resume to some system, sitting through a day of interviews, and then receiving an offer letter.

You’re looking for an answer that indicates some ownership of the process. If hiring seems to be everyone’s job, it becomes no one’s job. The company will struggle when it needs to hire the most.

How are new employees on-boarded?

I’ve left a job because there was no employee on-boarding process.

An employee’s first day is a 9-hour long first impression of your business. They will be consciously and subconsciouly recording lots of signals.

“Am I treated like a human or cog? Is the company organized enough to make sure my badge works on the first day? Is my desk set up? Did someone tell me how to connect to the WiFi? Is the first day just filled with training videos that haven’t been updated for years?”

How are people fired?

Much like hiring, firing is an extremely human process.

What you’re looking for here is some level of humaneness. This question is more important to seek out for first-time managers and first-time founders, since they may not have done it before.

You also want to get a sense of what the process looks like. You don’t want the process to be as short as “They had a disagreement with the CEO,” but you also don’t want it to be as long as, “We gave them several chances over the course of 9 months, and then they just didn’t work out.” Look for something that is humane but decisive.