Considering a role as an employee or co-founder at a young company? Here are some questions to help you size it up. Some may be more appropriate for the leadership, others may be better for employees. Comments or additions welcome.
Business
What problem does it solve, and what is the value that it seeks to add?
- What would that be worth to the average customer?
- How big is the market? Is it a niche, or is it pretty generic?
Tell me about your competitors.
- How are you different? How are you similar?
About how many customers do you have?
- Are you building for a large market, or for a few large clients?
How do you know what features to build?
- Are you doing Customer Development?
- Do you do A/B testing? Do you have a structured process for evaluating customer feedback?
- Do the founders have any background in this industry to help them understand the market?
- Are they taking orders from a few big clients?
- The idea is to do everything you can to build what the market actually wants, rather than building what you think the market wants. Also, to build for the market without building for the sale. You want to avoid having 10 1 page feature lists to sell 10 customers, and instead, to have a single 1 page feature list that can be sold to 100’s or 1000’s of customers.
What is the level of repeatability of your product?
- This is the ability of your product to be used by different customers without customization. Your customers must have a similar problem, and they must be willing to use your application to solve it, even if that means changing their processes and way of doing things.
- A high level of repeatability is the best way to prevent your application from becoming consultingware afflicted with a bad case of death-by-preferences. If you customize your product for every customer, your app logic gets complicated, which becomes a breeding ground for hard-to-spot bugs. It makes UX tougher, reduces your ability to do automated onboarding, and increases the number of humans needed for training users.
Are you more focused on sales or marketing?
- Is this forward-thinking?
- If they heavily use salesmen, what does their sales funnel look like?
- Do they focus on outbound or inbound marketing?
- Do they try to out-spend or out-teach their competition?
- Do they blog? Is it quality stuff?
- Are they a walled garden where prospects must go through salespeople to see the product?
- Or do they let the product sell itself with things like free trials, open documentation, marketing videos, and incentives to refer friends?
How good is their business model?
- Are they serious about using financial metrics to hone their business model?
How much human touch is needed to turn a prospect into a customer?
- Can they do touchless conversions? This Holy Grail of business models drives down the Cost to Acquire Customers.
- Low-touch models can grow quickly, because people are the most expensive thing to scale.
Culture
What is the pace that you foresee everyone working at over the next couple years? Do you believe this pace is sustainable?
- Are you expecting people to work a 30 hour week? 50 hour week? 70 hour week?
- Is that reasonable? Is that a good fit for this season of my life?
Are there pressures to grow at a certain pace due to investors, competition, or the nature of the market?
- Do we have regular deadlines that are driving our decisions?
- How much stress do you anticipate your employees will deal with on a regular basis?
What kind of company do you want to build? What is your vision for the culture?
- Do you like things casual – t-shirt and flip-flops?
- Do you want a more formal environment, where employees dress up to go to work?
- Can people work remote if they like, or is it important that everyone be under the same roof?
- How often do folks around here eat lunch together?
- Are intangible “quality of life” metrics (family, hobbies, physical / spiritual health, etc.) important enough to the leadership that they would prioritize these over growing as fast as possible? Is this desirable to you?
How much time should I expect to be in meetings?
- 15 minute standup every day? 1 hour per day? 3 hours per day? Is this appealing to you?
- Do you follow a structured process like SCRUM? How many regular meetings does this entail?
- Do they allow engineers, writers, and knowledge workers to run on the maker’s schedule? Or do they (unwisely and perhaps unwittingly) want them to use the manager’s schedule?
- Are folks allowed to do self-directed work?
What is the typical noise level?
- Do people have their own offices or do teams share wide-open spaces?
- As the book Peopleware points out, a quiet environment free of distractions is important for knowledge workers to get into a productive and pleasurable state of Flow. If you use your mind a lot in your job, peace and quiet may be very important to your quality of life and productivity in your work. Need to explain this to a non-believer? Try this.
Do you do one-on-one’s?
- How can I get semi-regular time with the person I report to?
- Will I have to report to multiple people?
- If my boss and I never spend quality time with each other, could I be comfortable being completely honest with them?
What character traits and skills do you need for this role? What hats will I be wearing?
- Is this a good fit with who you are? Is it playing to your strengths or weaknesses?
What values are you looking for in every team member?
- Are these values that are important to you? Would you enjoy working with people like this?
Benefits
What is the salary for this position?
- Is this an appropriate salary for your skill level and your financial needs?
Can I have equity in addition to salary?
- What type of equity is it?
- How many shares? What percentage of the company is this on fully-diluted basis?
- Will I actually own the stock up front (Founder’s Stock), or will I only have options to buy the stock? (Owning the stock ASAP can dramatically decrease capital gains tax.)
- Do you use vesting to protect against early departures?
- Are there any anti-dilution clauses for the current shareholders? (Be careful with these… they can be pretty harmful.)
How much vacation time?
- Traditional vacation time, flexible vacation, or minimum vacation?
- 2 weeks paid vacation seems to be pretty standard for starting a white-collar job. Most companies give you more vacation time the longer you stay.
Health insurance?
- Cost to me? Co-pay? Quality of the plan? Health / Dental / Vision?
Retirement package?
- 401k? SEP IRA? Simple IRA? Defined Benefit Plan? Company matching?
Do you provide any less common (but no less awesome) benefits?
- Can I work whenever, wherever I want? Do you have a place and time I need to be working?
- Will the company pay for continuing education? Books? Courses? Screencasts? Conferences?
- Does the company support philanthropies or ministries? Do they have specific ones that they support, or do they allow employees to choose causes that they care about? Do they do it through donations, unpaid team-volunteer days, or paid team-volunteer days?
- Free meals or snacks?
- Can I have my own whiteboard?
- Additional monitor(s)?
- Office area where folks can work outside?
- Standing desks? Kneeling chairs? Hanging desks?
Technical
What is the profile of your typical user?
- Is this geared towards Enterprise use, or is it built for individuals?
- Are there regulatory requirements in this industry (Ex. Personally Identifiable Information) that might prevent you from using hosted software solutions, meaning that you have to roll-your-own regularly?
- Are there industry quirks (Ex. Corporate customers still running old versions of IE) that might prevent you from using the latest frameworks or standards?
What are you focused on doing with your product right now?
- How will I fit into that?
What are some of the technical challenges that you’ve faced so far?
- What are some that you anticipate in the future?
Do you write tests?
- Do you use a CI server?
- What’s your estimated test coverage?
- What’s your tolerance for bugs? Do they vigilantly fix bugs before making new features?
- Or are they sacrificing quality at the altar of features?
Are you building for mobile?
- Responsive design? Native apps?
- Is the team provided with tablets and smartphones for testing?
Can I use your product before I join your team?
- Performance – fast or slow?
- Design – modern or dated?
How important is code quality to you?
- Do you do code reviews?
- How often do you cease feature development to pay down technical debt?
- Do you use a code quality tool?
- Do you follow a code style guide?
What tools and frameworks do you use?
- Are these wise choices? Are they running up-to-date versions?
What is your SCM process?
- Are there things that have to happen before code can be merged to master?
- Are there things that have to happen before code can be deployed?
- Do you have an automated deployment process, or do you have to setup stuff manually?
- How often do you deploy? Quarterly? Monthly? Weekly? Nightly? Continuous Deployment?
How complex is your application?
- About how many lines of code? 25,000? 100,000? More?
- Is it a monolithic app, or is it composed of SOA-style API’s?
What are your technical team’s strengths and weaknesses?
- Balance of Engineering, Design, and Testing?
Leadership
I’m interested to hear your story.
- Listen for arrogance, excessive achievement quantification, or humility to learn from their mistakes.
- Also, observe them for unhealthy decisions that may be the by-product of working too much – not eating healthy, not exercising, weight problems, not sleeping enough, etc.
What are some of your favorite books?
- What does this tell you about what’s important to them? Do these square with your values?
Are there multiple founders? How long have you known each other? What has your relationship been like?
- The longer they have known each other, the more likely they have “dated” before they got married. How much do they trust each other?
- On the other hand, is this a family business? (If so, might folks play favorites?)
Are you bootstrapped, angel funded, or VC?
- If yes, why did you make this decision? What affect has this had on your companies’ culture?
- If yes, when are you planning to raise the next round of funding?
- If no, do you anticipate tapping into either down the road?
- If there are investors, it is good to know if they took 15% or 55% of the company.
What is the leadership structure? How are tough decisions ultimately made?
- A single CEO?
- Board of Directors?
- What is the founder equity split?
- Do all founders have equal decision making authority, or is equity irrelevant to decision making authority?
Well, that’s all I’ve got. You probably can’t ask this many questions in a typical interview, but hopefully they got you thinking about what’s valuable to you, and what things you’d like to see in the next company you invest yourself in.