Questions to Ask Before Joining a Startup
Questions for a candidate deciding whether to take a startup offer, covering runway and burn, what the equity is actually worth, the terms that decide whether you ever see it, the founders, attrition, and what the job will be in a bad quarter.
The questions
Open any question for the note
How much cash is in the bank, and what is the monthly burn?
Why ask it
Two numbers give you the runway yourself, which is more reliable than a stated figure. Hesitation about sharing them at offer stage is itself informative, since the finance team knows both to the day.
When did you last raise, how much, and at what valuation?
Why ask it
The date tells you where you are in the funding cycle, and the valuation tells you what your options have to beat before they are worth anything. A raise more than two years ago with no news since is worth asking about.
What has to be true for the next round, and how close are you?
Why ask it
Look for specific metrics and current numbers against them. A milestone described only as growth usually means the target has not been agreed with existing investors.
What happens if the next round does not come together?
Why ask it
Reasonable answers include cutting to profitability, a bridge from existing investors, or a sale. An answer that treats the question as unthinkable tells you the plan does not exist.
Is revenue growing, and what does a typical customer pay?
Why ask it
Growth rate plus contract size tells you whether the business is real or still a pilot programme. Ask how many customers make up most of the revenue, since concentration is a common fragility.
How many shares am I being granted, and how many are outstanding on a fully diluted basis?
Why ask it
A number of options is meaningless without the denominator. If you are given a percentage instead, ask whether it accounts for the option pool and any convertible notes, because it often does not.
What is the strike price, the current preferred price, and the last 409A or equivalent valuation?
Why ask it
These three figures show how much the company has to appreciate before your equity clears its own cost. This is where an offer that sounds generous frequently turns out to be thin.
How much liquidation preference sits ahead of common shares?
Why ask it
Preferred investors are paid first, and if the stack exceeds a modest exit, common shareholders receive little. Employees at companies that sold for large sums have often received nothing for exactly this reason.
What is the vesting schedule, and what is the exercise window if I leave?
Why ask it
A ninety day window means you must find the cash and pay the tax within three months or lose the options entirely. Extended windows exist, and asking about it now is far cheaper than discovering it later.
Do you have single or double trigger acceleration on an acquisition?
Why ask it
It determines what happens to unvested equity if the company is bought and your role disappears. Most offers have neither, but the answer tells you how the company thinks about employee equity.
How does the salary compare to the market, and what would it take to revisit it in a year?
Why ask it
You are usually accepting a discount in exchange for equity, and naming its size makes the trade explicit rather than assumed. Ask whether the gap is expected to close as the company raises, or never.
What are the first three things you would want me to deliver?
Why ask it
Specific answers mean the role was designed. A list of everything in the function usually means you would be absorbing whatever the founders currently do not have time for.
Who would I report to, and how long have they been in that seat?
Why ask it
Reporting lines at startups change quickly, and a manager who arrived last month may not be the one who reviews you. Ask who else could end up as your manager within a year.
How do the founders divide responsibility, and what have they disagreed about recently?
Why ask it
A specific disagreement described calmly is a healthy sign. If they cannot name one, either the relationship is unexamined or one founder is deciding everything.
Who has left in the past year, and why?
Why ask it
At a small company you can often verify departures independently. Several senior exits in a short period matter more than any statement about culture.
What does a genuinely bad week look like here?
Why ask it
The answer reveals working hours, weekend expectations, and how pressure is distributed far better than a question about work-life balance, which invites a rehearsed reply.
Who are you losing deals to, and why?
Why ask it
A clear answer means the company understands its market. Claiming no real competitors usually means either the category is unproven or nobody is listening to lost prospects.
How do decisions get made when the founders disagree with the data?
Why ask it
This is where you learn whether the company is genuinely evidence-led or whether conviction wins. It predicts a great deal about how your own recommendations will be received.
What is the plan for the company: keep building, sell, or go public?
Why ask it
The intended path determines whether your equity has a plausible route to value and on what timescale. Founders who want to run the business for decades and employees hoping for liquidity in four years are not aligned.
May I speak with someone on the team without a founder present, and with someone who left?
Why ask it
Employees are more candid alone, and former employees will explain the part nobody volunteers. Refusing both requests at offer stage is a decisive answer in its own right.
Evaluating the offer
Practical guidance for the conversation itself
Working out what the equity is worth
- 1Get the share count granted and the fully diluted total, then calculate your percentage yourself.
- 2Ask for the strike price and the most recent valuation, and note the gap you would have to fund to exercise.
- 3Ask what sits ahead of common shares in a sale, including preference multiples and any participation.
- 4Model three outcomes: the company sells for what it last raised at, for three times that, and for nothing. Two of the three are the common cases.
- 5Ask the exercise window and whether it extends after you leave, because this decides whether the equity is real or theoretical for anyone who does not stay to an exit.
Checks worth doing yourself
Look up the funding history
Filings and press coverage will usually tell you when the company last raised and roughly how much. A long gap with a growing team is the pattern to ask about directly.
Track the team over time
Public profiles show who joined and who left. Departures clustered in one quarter or one function are worth raising in the interview, politely and specifically.
Talk to a customer if you can
A single conversation with someone who pays for the product tells you more about the business than a demo does.
Get everything in the written offer
Share count, denominator, strike price, vesting, exercise window, and title. Verbal assurances about equity do not survive a change of chief executive.
Traps that catch experienced people
Treating a percentage as fixed
Your stake shrinks with every subsequent round. The question is not what percentage you hold today but whether the company grows enough to outrun the dilution.
Accepting a large salary cut on optimism
Work out what you are giving up over four years in cash terms, then ask whether the equity plausibly covers it. Sometimes it does, but it should be a calculation rather than a feeling.
Skipping the reference calls
Candidates research the market carefully and then decline to speak to former employees. That conversation is usually the highest value hour in the whole process.