Questions to ask in your job search to avoid hating your next role

When Chase, a former McKinsey consultant, was interviewing for a new job recently, he decided to try a new approach to evaluating the opportunity. He had decided he wanted to work at the intersection of consumer brands and media & entertainment, and he had scheduled an interview to do just that. But even though it was the job he wanted, Chase decided to first take some time to reflect on his career and experiences.

At the core of it, he wanted to answer one question: “What has made me happy in my previous roles?” What he discovered helped him refocus conversations with prospective employers — and ask questions in his job search that allowed him to find a role he enjoys.  

Important questions to ask

Chase had a good reason for wanting to take a more thoughtful approach to his job search. In fact, according to The Conference Board, 46% of workers are not satisfied with their work. In my experience, there are two main reasons for this.

First, most people say that compensation isn’t the biggest consideration for their career choices, but when it comes down to it, they often do select their jobs based on who’s offering the most. Scientific studies, however, show that pay has only a minimal impact on job satisfaction.

Second, most people focus on what they want to do, not how they will do that job. That is, most individuals focus on the company they want to work for, the industry they want to work in and the profession they want to be in. It’s as if we are all back in kindergarten and the teacher is asking us what we want to be when we grow up—and us answering with the profession of our choice. 

Profession and industry do impact overall career satisfaction, just less than you might think. But in my experience, job satisfaction derives from a complex set of factors, many of which have little to do with the problems you or your organization are solving. Most importantly, you want to know:

  • How much of your time goes to tasks and responsibilities that give you energy vs. tasks that drain your energy?
  • How well does your work style match with what’s required of you?
  • Do you fit in well with the company’s culture?

Answering these questions during your job search starts with figuring out what’s important to you. When Chase asked himself this question, he found it difficult to come up with an answer. So instead, he reflected on previous experiences and asked himself whether he had been happy working with various supervisors in previous roles—and why. His initial hunch was that a lot of his happiness in a role was driven by how interesting he found the industry he worked in.

After digging a bit further and to his surprise, he found that while the industry made the work a bit energizing, it was not the best predictor of his happiness. He realized that even if he was working in an interesting industry, he was unhappy when he could not buy into the business logic of the company’s leaders. He did not want to work in a company where the leaders asked the employees to drink the Kool-Aid and blindly follow the strategy.

It was important to him that the company leaders could engage in discussions about their business model and be able to convince him that they were right about their vision. In his next conversation with his potential employer, Chase, therefore, decided to dig deeper into their business model. Chase asked his prospective supervisor what they do to ensure a piece of media is easy to merchandise while it’s still in production.

The response he received was clear, yet disappointing. “Whatever they do other there, it doesn’t matter to us. We just take what they give us and focus on what’s on our plate,” the interviewer told him. Chase was conflicted. This was exactly the industry he wanted to work in. And having this job on his resume would open a lot of doors down the line. Yet, he knew the last thing he wanted to do is work at a siloed company where the success of his and his team’s daily work was controlled by a side of the business he would never even talk to.

Blindly following commands was not what he wanted. He, therefore, decided to pass on the opportunity.  

Other questions to consider

Chase’s approach to asking questions during his job search led him to learn about the company’s business model, bringing him closer to a job that was a good fit for him. But there are some other important questions that can help a job candidate determine whether they’ll be happy at their next job, including:

  • How would you expect a successful person in this role to split their time between their various responsibilities? 
  • What day-to-day activities did your past hires find most challenging in this role? 
  • Who are a few of your happiest employees (ideally in this role)? Why do you think your organization is such a good fit for them? Why do you think you were not a good fit for a few people who did not perform well in this role?
  • You described your culture as ______. Can you provide a few recent examples of how that has manifested itself?    

Admittedly, asking these questions in an interview can feel awkward. You don’t want to come across as overly critical. That’s why the way you ask these questions matter. Use a friendly tone, smile and start with a softening statement like “I want to make sure I will be a good fit for you. Is it OK if I ask a few more detailed questions?”

A few months later in his job search, Chase interviewed with ArcLight Cinemas, a high-end circuit of movie theatres. In the course of the interviews, many at the company had discussed designing a more meaningful experience for guests.

“I’ve heard a lot of ambitious goals in my time speaking with you. How are you actually expecting to reach them?” Chase asked. The executive walked Chase through a new initiative they were launching in their concessions stand. “Is that what’s going to make a difference? One new concession item?” Chase asked. “Absolutely not,” the executive responded and then walked Chase through the plan for the business: how better connecting with guests could be driven through a few key areas, concessions being only one of them, and how the spirit of rapid testing and prototyping would build the foundation for future innovation. “

The conversation felt open, honest and like something that made sense,” Chase recalled. The outcome of asking

Taking a more thoughtful approach to vetting his next opportunity paid off for Chase. He accepted the job with ArcLight Cinemas and now over a year later is still very happy about his decision. “Nothing is taken for granted here. We are not asked to overlook any decisions about our business model just because someone higher up made that decision and ‘this is the way he or she wants it to be.’ We can challenge every assumption about how we run our business and ultimately do what makes sense,” Chase explained to me. “Being in an environment like this is exactly what energizes me.” 

The same could be true for you. In your job search, focus on how you will do your job instead of just what you do, enabling you to find a job that’s a better fit for you. Start with the questions above and adjust them as you see fit. And after going through your questions to your prospective employer, the most important part is to be honest with yourself when answering one final question: “Do I truly believe I will be happy in this role?”

Once Chase was able to say yes, he knew he had found the right employer.