Top 5 Questions to Ask When Looking for a New Job

By Tyler King

Reading Time: 6 minutes

We’ve all seen the headlines over the last six months. Articles like “The Great Resignation is Upon Us” or “Record Number of Employees Ditch their Current Job for New Opportunities thanks to Remote Work.” 

UVM Digital Marketing Instructor Tyler King
Tyler King, UVM Digital Marketing Instructor

And it’s true; recent studies have shown that over the last 18 months, more than 7 million Americans have changed jobs, and I was one of them. But here’s the crazy part, I wasn’t looking. I loved my job, boss, team, and company, but right around January 2022, I started to see my LinkedIn feed filled with stories of people moving on from their jobs, and I thought, “should I start looking?” 

I was also in the process of moving my family from Utah to South Carolina, so starting a new job was the last thing on my mind. But then I got a LinkedIn message from a recruiter, and a little voice in my head told me I should probably talk to them. This wasn’t anything new. Over the last two years, dozens of recruiters have done the same. It’s always a good idea to see where you stand in the market, so I would always chat with them, but nothing seemed like the right fit. But after my first conversation with the new recruiter, I realized this could be a great opportunity, and I needed to put together a plan. I wasn’t going to leave my current job just for more money or a title. Life is too short to work for a terrible company, and it’s not worth your mental health to stick it out just for a paycheck. So one evening, I took a couple of hours and outlined my criteria to leave the job and company I loved, and here’s what I came up with.

When Looking for a New Job: Ask These 5 Questions

Q1: What Type of Leader and Manager is Your Boss?

The data shows that your boss will make or break your experience at a company, so knowing what kind of leadership you will work under is imperative as you evaluate new job offers. If you don’t like being micromanaged, find a boss that gives you the freedom to do your best work. From my experience, the best bosses are just like great coaches. They coach you when you need to and trust you to do your best work. When you make a mistake, instead of coming down on you with an iron fist, they correct the problem when it happens, giving you the tools and confidence to fix it. With so many companies moving to a hybrid or fully remote model, finding an excellent communicator is more important than ever.

Q2: What Really is the Company Culture?

Company Culture has been a buzzword for the last decade, and the sad thing is, it can mean different things to different companies. Many organizations think company culture is all the free stuff they give their employees (free food, beer, swag, gift cards), but those are just perks. Pre-Pandemic companies were in an arms race to see who could give their employees the best, but once the pandemic hit and their employees went remote, many of those perks went away, and companies were left with nothing but empty break rooms. 

Authentic company culture is about creating an environment where every employee feels respected, and the organization has policies and procedures that ensure people can do their best work. And sure, perks are part of that, but it can’t be the only thing.

“Transparency, accountability, treating people like people, and having an appropriate work-life balance are all part of a great company culture.”

Tyler King, UVM Digital Marketing Instructor

Q3: Can You Grow Your Career? 

This was a big one for me. I had been at my current company for six years which is 30 in Millennial years, and I started to feel like I had reached the end of the road. After 12 years in the digital marketing world, I knew the next step in my career was to lead a social media team, which meant I needed to learn how to lead people. I put together plans at my current company to demonstrate why social media is more than a one-person team, but it wasn’t in the cards.

And that was an essential lesson for me to learn. What you need in your career doesn’t always match what your company wants or needs to do. And that’s fine, an organization can’t meet the career goals of every one of its employees. So as you evaluate job offers, make sure your next job allows you to grow your marketing skills; no situation will be perfect but set the expectations early with your new boss of what you need to succeed in your career. 

Q4: Is the Compensation Competitive?

I don’t care who you are, we all need money, but it should NOT be the driving force in your decision to leave a company. It should be in the top 5 reasons but if you decide to make a move based on solely on money, you open yourself up to being on the job market sooner than you expected. The COVID-19 pandemic was awful, but there have been a few critical consequences that have changed the game regarding your career. Thanks to remote work, you’re not limited by your geography to determine how much you make. The talent competition is at an all-time high, and that means you now have an opportunity to see how much your talent is worth on a national scale. As I chatted with friends and co-workers who changed jobs over the last two years, I saw a trend. They were leaving for offers 30-50% more than they were making at their current job. And with the way inflation has skyrocketed these last few months, it’s never a bad idea to earn more money. By interviewing and networking, it’s an opportunity to research your worth in the open market.

digital marketing
UVM Instructor Tyler King and family stop for a photo while moving across country.

Q5: Does the Company Provide Value to People?

If I’m going to work for a company they need to make the world a better place. Now, does that mean you should only work for non-profits? You should find industries you’re passionate about and audiences that you can relate to. I love working with small businesses, and creating social media campaigns for them may not cure cancer, but it helps real people get to live their dreams as business owners. The more successful small businesses are, the more people they can hire, which is always a good thing. 

This list may not apply to every person and situation, but considering these top 5 questions when thinking about a new job can provide a solid outline of what you need to consider to make your best choice.


Tyler King is a Senior Social Media and Community Manager at PandaDoc in addition to an instructor in UVM’s Digital Marketing Fundamentals Professional Certificate Program.


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