The 2 most annoying interview questions Boomers get, and how to answer them

Baby Boomers are staying in the labor force and working later in life at rates not seen in generations for their age, according to Pew Research Center. By 2024, 25% of the American workforce will be made up of workers over the age of 55, a record high, according to the Bureau of Labor Statistics.

But you don’t have to do anything but skim through the news and catch up on the “OK, Boomer” meme to know that Baby Boomers – despite their decades of skills and experience – aren’t always getting the respect they deserve, in and out of the workplace.

Boomers have a lot to offer, says Mark Silverman, CEO and founder of Amava, an online platform he says is focused on “empowering” this generation of tech-savvy workers “nearing the end of their careers, or extending them and living in semi-retirement, to make successful transitions.”

It also connects their members – including retirees and empty nesters – with flexible or part-time jobs.

“Some of them are looking for full -time work and continuing their careers, but a lot of them are looking for flexible part-time work,” said Silverman.

With the rise of behavioral interview questions, interviewing hasn’t gotten any easier. Interviewing at 55 and older isn’t easy, and Silverman has gotten feedback about the most difficult – some would say ageist – questions his members have gotten over and over again. Some of them, he says, tread on “subtle age discrimination.”

He does have some ideas on how to answer these questions, however, so they don’t derail your job interview.

1. Why would someone with so much experience want this job?

“This is both my favorite and the most hated question. It’s really hard to not think of this as an attack on age and experience itself. But I do think that it’s a question that’s often asked by somebody that doesn’t do a lot of interviewing. 

“But the answer to the question is very hard in terms of just a direct answer, because clearly what they’re interpreting your application as somebody who hasn’t been able to continue to leverage that experience to grow in their career and get to the next level. And so there’s an inherent judgment on the question that’s off-putting to a lot of people who are interviewing.”

“What I tend to recommend, and I’ve talked to a number of members that have dealt with this question, is to really focus on two different things. One is, don’t really focus on the levels you’ve achieved in your career and don’t focus on the need for let’s say, validation based on some type of title or something. Focus on the skills you have and then give three or four reasons why you’re making a change in direction.”

“And these can be really basic reasons for making a change. It can simply be, look, I’m looking for a place that’s closer to me that has a shorter commute. I’m looking for a place that has a culture that isn’t really looking to work with them and can grow with them. And yes, absolutely, I’m willing to take a step back in terms of title or even compensation because that’s more important to me at this stage of life, is finding a place where I’m really comfortable working where I can really contribute to the high level.”

“When I asked our members, most of the interviewers don’t pursue this question. So if you give a really solid and basic answer, that’s a combination of ‘Here are the skills that I’d like to bring in, here’s really the reasons why I’m making this change,’ the one or two things. They to move on and not worry about it.”

“If people get defensive or they get offended by the question, it can really derail the interview. So I think preparing for this one in particular, it’s important.”

2. What is your upskilling strategy?

Silverman cautions those on the receiving end of this question not to be too defensive – and focus on ways they’d like to develop professionally instead. “The question is really targeting [Boomers] because of their age, but more that it’s simply a question asking about areas for improvement, and an opportunity to show their continued curiosity and desire to grow as an employee and as a person.”

“And so I always think that it’s good for people that are going into an interview at any age, to think about what are the areas of development that they would want to focus on if the employer made them available to them – and they don’t have to be areas of critical weakness associated with the particular job skills required.”

“Obviously, [the question] can be problematic. But they could focus on areas of improvement, whether it’s new technical skills associated with different types of tools – let’s say, a new CRM system that might have been deployed or the ERP system that’s been deployed if you’re on the sales or marketing side. Or it could simply be areas around the leadership that you want to continue to focus on based on your experiences in the past.”

“What we’ve found is the members that come up with one or two areas that they really want to focus on, in terms of continuing their education and continuing development of their skills. It’s actually a straight question to answer from that perspective. Almost everybody who’s reentering the workforce or continuing in the workforce has areas that they would really love to take a step back and spend a few hours a week developing skills around or perfecting and polishing some of their skills.”