I never learn anything talking. I only learn things when I ask questions. - Lou Holtz

Leaving a company voted as one of the “Best Places to Work” is not a decision that should be taken lightly. Before I joined my first startup, I talked to all the investors and had multiple conversations with the CEO. However, I did not get a chance to talk to the other founders and employees due to time-sensitive equity terms. After I joined, I connected with a few of the engineers and found out that there were some issues behind the shiny exterior. Looking back, I should’ve trusted my instinct and asked for more time. More time would have allowed me to get more information from other founders and employers about the company culture and operations. In addition, I could have connected with those who previously worked with the founders and my industry peers to get a more balanced perspective and catch the warning signs sooner

When considering any startup, you should always ask to meet the founders, investors and any relevant people (employee, external partners, vendors, etc) you would be working with. If they don’t let you meet or speak candidly with these individuals, then run as far away as possible. If they oblige, then ask these set of questions to each individual you speak to. Your goal is to meet and get to know a good representation of the people you’ll be working with.

Here are the questions you should ask:

  1. What is the most important priority for this company?
  2. How do you think this might evolve over the coming months?
  3. What gets you excited about this company?
  4. Why do you like coming to work everyday?

There are other questions you can ask, but it is equally important to listen closely. What is more important is to pay attention to their responses and how each individual answers the questions. From their responses, you should look for the following:

  1. Are the responses consistent? If the responses are inconsistent, this is a major red flag. If the responses are inconsistent across founders and employees, there is likely a major communication issue internally and/or externally. Even worse, this could also represent a lack of culture or unity within the company.
  2. What are the common themes? When you ask the same set of questions, you should be able to discern themes or common phrases used in those conversations. Given my last startup experience, I have prioritized authenticity, accountability, user impact and a safe work environment for any company I consider in the future. I highly recommend to draft a list of values that are most important and see if the responses align.
  3. What are the tone and body language? Do they maintain eye contact? Do they sound energized or deflated? Do they use a lot of adjectives but can’t back up with examples? Evaluate their choice of words and body language when they describe the company and what they’re working on. Passion and enthusiasm are just as easy to pick up on as fear and apathy. Body language like fidgeting or darting eyes may indicate that there is something they do not want you to find out about.
  4. How did the conversation flow? The best conversations are discussions where there is nearly equal exchange of information, questions and opinions between both parties. Equal exchange is a good indicator of cultural fit and whether you can work together with the team to make the startup successful.
  5. Is the company’s future viable? Have they set goals and key performance metrics to measure progress? In the end, every company needs a plan to build and grow a sustainable business and eventually make profit. Great teams are aligned and working together to achieve a goal. It is a good sign if everyone in the company can clearly communicate the path to success and understands how his or her work can contribute to that success. If individuals or groups are not aligned, these are major red flags that signal lack of focus, poor leadership or poor execution.

Above all, take your time making this decision. Despite the opportunities a startup can offer for your professional and personal growth, working at a startup comes with the cost of financial instability, decreased compensation, emotional and mental stress, and strained relationships. You will more than likely have minuscule equity share compared to the founders. If you are going to join a startup, you should not only be 100% sure that you are passionate about the company’s vision and product, you should also be 200% excited to work with the founders, investors and potential colleagues. Your time is valuable. It is the one asset you cannot make back, so it’s critical to be protective of your time and spend that time with the people you’re not only excited to learn from but grow with.

Questions to ask in your next interview