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The Five Questions You Need To Ask Before Accepting A New Job


Alex Douzet is CEO of Pumpkin, a pet insurance and wellness care provider founded to help ensure pets live their healthiest lives.

If you’ve felt the pull of the “Great Resignation” and are considering changing jobs or careers, asking the right questions during the hiring stage can make the difference between joining a company that sounds great or one that is truly great.

When an interviewer asks, “Do you have any questions for me?” you should feel empowered to ask hard-hitting questions that help you evaluate the company and understand what it will be like to work there. These are the five questions I think all candidates should ask potential employers to determine if the job is the right fit for them.

1. What is your company’s purpose?

You’ll spend every day thinking about the problems your company is trying to solve, so their goals and mission should excite you. Any senior employee should be able to concisely describe the company’s goals as well as their plan to achieve them over the next year and beyond. Your future manager should be able to list your team’s specific goals and describe how your role and performance impact the company’s long-term plan.

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At my company, a pet insurance provider, I interview all potential employees. Nothing is off-limits. I encourage them to ask me anything and am frank in my answers. While meeting the CEO isn’t possible at every company, a conversation like this is an opportunity for you to assess whether a company has a steadfast mission or if they are aimlessly pivoting and changing priorities (which impacts resources, culture and success).

2. What is the financial health of the company?

You want to tie yourself to a rocket ship, not a sinking ship. You want to know the future of the company you’re joining is trending upward. Are they in a thriving industry and surpassing their competitors? Are they well-funded? Are they meeting or exceeding their revenue expectations?

Many candidates overlook or don’t feel comfortable asking questions like these. They might assume any company that’s hiring is doing well or that asking these questions will go against them. I argue that every employee should ask how well the company is doing and what sets them apart. Plus, if leadership is transparent about the company’s position and financials, that’s a positive sign.

3. What are your company’s core values, and how do you embody them?

Beyond a mission and vision statement, every company should have easy-to-articulate, memorable core values that all employees know and embrace. They should be more than words in a forgotten presentation. Take one of my company’s core values, “Trust the pack.” While we could have said we value teamwork and collaboration, we made a point to choose specific language that’s grounded in our commitment to pets and their people. We make sure our core values are evident in all we do—from our hiring process to onboarding, performance reviews and day-to-day decisions.

If a company says one of its core values is to actively seek diversity and create equity, you should ask how this value is reflected in their recruiting process, onboarding, promotional cycle and even their company holiday calendar. They should be able to identify concrete examples that reflect their core values in their daily operations and company policies.

4. How would you describe the company culture?

There’s a saying that culture will eat a company’s strategy for breakfast, lunch and dinner. If the culture is broken, a company cannot succeed no matter what they do. For you to thrive within a company, their culture must match yours. Beyond factors like your compensation and growth opportunities, will you build positive relationships and be happy working there?

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When assessing the culture, try to move past generic answers or corporate buzzwords to understand the thoughtful steps they’ve taken to create a positive work environment. How do they accommodate employee needs? How do they celebrate their wins and handle their failures? What’s their office structure, and will it suit you? Also note that if employees give wildly different answers about the culture, that company doesn’t have a strong, unified culture.

5. What can I do to succeed in this role?

It’s vital to know what’s expected of you and how your success will be measured in order to thrive in a new role. Beyond that, you need leadership that cares about your performance and pushes you to improve. Your manager’s success is an aggregate of everyone beneath them. They should be invested in providing you with the tools and support you need to succeed.

One of the best questions no one asks their future manager is, “What do I need to do to make sure you get a gold star by the end of this year?” Pay attention to the answer; if they can articulate your responsibilities and how your performance impacts their own success in their role, that job has promise.

Key Takeaways

In the job market, the grass will always look greener, but it pays to look beyond appearances and discover whether a company has solid roots. Truly great jobs are hard to find, but asking these questions up front can help you visualize the environment and culture you’ll be a part of. With that knowledge, you can confidently decide if it’s a place where you can build a successful career.


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