Over the last few years I’ve collected a bunch of questions that have largely sat in my head that I tend to bring up during an interview process. This was born out of a google doc I put together for some old coworkers who were looking for new jobs and I started sharing it with more and more people. These particular set of questions are mainly geared towards startups but there are sections that apply to any type of company. Not all of these questions may be relevant to you and by no means is this an exhaustive list of things to consider. Nor should you take these questions and just throw them at a prospective employer but they are for you to build conversations with during different stages of the interview process.
Before even applying to a company, I research the following items…
- Any news of recent layoffs
- Company morale will be pretty low at this point
- Company’s growth may have stalled
- May lead to additional people leaving
- Executive turnover
- Is there a replacement yet?
- Expect changes from a new person coming into that area
- ⚠️ Has there been multiple executive departures in < 1 year? Could hint at issues with the CEO
- Glassdoor reviews
- Is there a notable trend in a certain direction?
- Are the only bad reviews coming from one department?
- Expect some negativity from disgruntled employees, it’s rare to have 100% positive reviews
- ⚠️ Are a bunch of the reviews clustered to a particular date? Companies like to bribe their employees to write reviews or worse I’ve heard of people being asked to write a review as part of their onboarding which won’t lead to any accurate reflection of the state of the company
- Recent fund raising announcements
- Are they raising at higher valuations?
- Who are they taking money from?
- Do these funds align with your values?
- Have they raised debt recently?
- Talk to friends in the industry about the company or reach out to friends I know there and ask them their view of the company
About the Position
- What major projects will I be working on?
- What will my day to day look like?
- If the job is not a new position/hire for the company, why did the last person leave this position?
- Why wasn’t this position filled from within?
- What does success look like in this position?
- What are future growth opportunities being in this position?
About the Company
- What’s your 1 year plan? 3 year plan?
- What defines success for the company?
- An IPO?
- Selling to another company?
- Who are your biggest competitors and why are you better than them?
- ⚠️ If they say they have no competitors
- What’s your review process look like?
- What’s your level of transparency within the company?
- Do you reveal numbers like revenue and burn rate?
- What are your future funding plans?
- What’s your board structure look like?
- ⚠️ No outside board members with voting rights
- What has your company been doing to improve it’s diversity and inclusion?
- What’s company’s growth plans in terms of revenue and head count?
- What’s been recent YoY growth in…?
- What’s the average leadership tenure been?
- What sort of company culture events do you host?
- Are they all drinking based?
- How has the company vision progressed or shifted since it’s founding?
- Ask hiring manager or CEO: What was the biggest mistake in their career?
- Are they confident and honest enough with you to speak openly about their mistakes and what they learned from them?
- What is your infrastructure hosted on?
- What technologies do you utilize?
- What does your oncall rotation look like?
- Do you offer reimbursement for cellphone bill if oncall is required or provide a phone?
- How often will I be oncall?
- Is it just business hours or 24⁄7?
- How many engineers do you have?
- What’s your growth plan through the year and next?
- What’s your deploy process look like?
- Do engineers deploy their own code?
- How long does it take to push a change into production?
- How often do you push code?
- Is tech debt included in your normal sprint planning?
- When do you build vs when do you buy?
- How are product decisions made?
- Is there a product organization?
- What does your code review process look like?
- What does the testing process look like?
- What’s the process when something breaks?
- Are blameless postmortems held?
- What type of equity do you offer? Options? RSUs?
- Vesting schedule?
- Type of options?
- Single trigger or double trigger?
- If ISO options, will you convert to NSO upon leaving and extending the amount of time I have to exercise from 90 days to X years?
- If options, what’s the strike price?
- How many outstanding shares do you have?
- ⚠️ If they refuse to give this, be wary.
- What percentage does my stock represent?
- You should be able to calculate this on your own with outstanding shares, if they don’t match, something is wrong.
- Do any investors have greater than a 1x liquidation preference?
- ⚠️ Non-standard terms usually are a sign that the company had trouble raising money and means your equity could be worth less in a liquidation event
- Read more about liquidation preferences at: Terms Valuations
- What sort of benefits do you offer?
- Gym reimbursement?
- FSA or HSA?
- What’s your maternity/paternity leave policy?
- What’s your remote work/WFH policy?
- Are there any performance based incentive plans?
- What’s your continuing education and conference policy?
⚠️ General Warning Signs
- No straightforward answer on how money is made or will be made
- If a company is just trying acquire market share and figure out how to monetize later
- Can’t give you an elevator pitch on what the company is
- Anyone trying to sell you on equity as a replacement for underpaying you (exception is seed or lower with obvious risk being there)
- Always assume your equity will be worth nothing unless the company has liquidity for their shares (e.g public)
- They agree to terms but refuse to put them in writing
- Very different answers from questions around company process or goals between interviewers
Thank you dvd, devon, matt k, alisa, eugene, and brett for your contributions to this post.