Questions to ask your next employer

Questions listed below are for various situations. You’ll have to choose the ones that fit your situation the most. The goal is to understand what experience is awaiting you on the other side.

You only have one first impression. Keep it friendly and open-minded.

Company representers will ask you questions that prove your value. Employer’s aim is to get the most value for the resources they have. Thus, a good candidate is the one who brings more than he takes out. Keep that in mind.


Human Resources staff represents the company, its objectives, and interests. They are not there to care about you as a person but as a professional, a colleague. So, you should ask her/him:

  1. From an employee perspective, what makes your company a good place to work?
  2. What top two values do you believe are the most crucial for a new hire to have?
  3. What is the company’s method for recognizing achievements?
  4. How does a company check if profession you’re there for is good at their job?
  5. What is the best way to grow in your company?

And then once the conversation is there and rapport is set it’s a great idea to ask:

Does the company operate on business revenue or running off funding?

And the trickiest question with the most value is:

Let’s imagine I found a tool that can improve my productivity. What process do I go through to buy it? What if it costs $150? Or $450?

The answer will allow you to understand the inner processes of a company. You’ll see the value it puts on productivity and the way it handles bureaucracy.

Founders & C-level executives

It’s a great place to get an understanding of a company’s direction and showcase the value you have.

It’s better to start off with something simple yet fruitful to understand the person.

  1. Why have you decided to pursue this product/market?
  2. What do you believe motivates your employees/colleagues?
  3. From an employee perspective, what makes your company a good place to work?
  4. Is anyone in the sales technology-driven? Are they technical?
  5. What is your preference, a large number of small customers or a small number of large customers? Why?
  6. What is the best way to grow in your company?

These questions are quite open yet informative enough to provide a solid bird’s eye view of a company.

If you think the conversation is flowing, it’s a good time to expand and ask deeper questions.

  1. Since you came on as CEO/CTO, has your vision changed? Why?
  2. What know-how do you expect from the position you’re there for? How should one help the company achieve its objectives?
  3. When was the last time your missed payroll?
  4. Who is your main competitor? 4.1. In what ways your product is better? 4.2. What separates you from your competitors?
  5. Do you share board meeting slides with employees?
  6. Are your company's strategy and development team close?
  7. How do you adapt the culture to achieve the company’s objectives?
  8. What is lacking in the workplace? Those reasons that would make some quit and others join? I’ll get to know either way.

It’s likely you won’t be able to ask everything from the list above. So, select those questions that you think are the most relevant. Every position is unique. Companies vary in size, market, and industry.

Questions below will be great if you’re aiming for a position where you have leverage. These questions will provide an extra set of insights:

  1. What is your burn rate? How much capital is left?
  2. What’s the exit plan? IPO, private forever or to get acquired? How long until then given the metrics?
  3. How did your pricing model change? What were the reasons?


It’s crucial to understand the culture of the main component of any business. By asking questions below, you might get an answer based on a client pitch. Nonetheless, you’ll get a chance to get a feel of the company’s care for customer problems. You’ll see the approach, and moral stance as well as the market opportunity. No doubt, you’ll understand the company a tad better.

  1. Who’s responsible for the sales?
  2. How many people are in the sales team?
  3. What’s your user/customer acquisition model?
  4. Is the sales team technical?
  5. How do you manage the funnel?


It’s common to have a conversation with the potential teammates as well. The goal is to understand the fit, your expertise, and quality of a workplace.

Remember, potential colleagues can provide insight into your future at the company. Listen to your gut feeling. Track how conversation flows. If hired, you’ll be spending a lot of time talking with them. You better make sure it’s enjoyable or at least professional. A decent rule is not to join a company where teammates are not those people whom you would socialize with.

  1. What is the best way to grow in your company?
  2. What is the one thing a position you’re there for could do to help achieve the company’s objectives?
  3. How distractive is the work environment? Read stressful.

I hope you find this helpful and find the role you’re looking for. There’s always an opportunity, don’t let one bad apple spoil the box.