How to Wow an Interviewer Half Your Age, with Ruth Winden

Listen On:

One of the biggest challenges older job seekers face is connecting with younger hiring managers. Too many older workers look for jobs with the wrong employers and are not clear about the value of their experience. Ruth Winden says that if you have trouble working with younger hiring managers, you can fix it. She discusses how to do it in this episode of Find Your Dream Job. Ruth encourages older workers to begin by focusing their job search on companies that hire people from multiple generations. She also says it’s important for older workers to emphasize management experience and any evergreen skills they have. As an older worker, it’s up to you to find ways to connect with younger hiring managers and to be prepared for your next interview.

About Our Guest:

Ruth Winden is a career coach for professionals in their 50s, 60s, and 70s. She helps older workers overcome age bias and land new jobs with clarity, focus, and confidence. Ruth is also the author of the forthcoming book, “101 Ways to Overcome Ageism in the Workplace.”

Resources in This Episode:

  • If you’ve hit 50, 55, or 60 and you wonder where the time went, it’s not too late to follow your dreams and make a difference. On her blog, Older Yet Bolder, Ruth shares articles and resources to help you figure out what’s next.
  • Not knowing what to do next isn’t an excuse to give up at any age. Ruth offers personalized coaching for those who aren’t ready to contemplate retirement but who desire to continue working and interacting.


Find Your Dream Job, Episode 176:

How to Wow an Interviewer Half Your Age, with Ruth Winden

Airdate: January 30, 2019

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life.

I’m your host, Mac Prichard. I’m also the founder of Mac’s List. It’s a job board in the Pacific Northwest that helps professionals find fulfilling careers.

I believe that lifelong learning is the key to a successful career. And to get a better job, you need to learn the job hunting skills that will help you find the role of your dreams.

That’s why we’re here today. Every week on Find Your Dream Job, I interview a different career expert. We discuss the tools and tactics you need to find the work you want.

This week, I’m talking to Ruth Winden about how to wow an interviewer half your age.

Ruth Winden is an expert in helping older workers get jobs. And she says one of the biggest challenges these candidates face is connecting with younger hiring managers.

One mistake older applicants make, says Ruth, is not being clear about the value of the experience they offer. Technical skills often become outdated, she says. So, older workers need to emphasize management and other evergreen abilities.

Too many older applicants look for work with the wrong employers, she says. So Ruth encourages these candidates to focus on companies that hire people from multiple generations.

And she cautions that it’s up to older workers to work well with younger managers. If you’re not good at this, Ruth says, you need to fix it.

Want to learn more? Listen in now at the Mac’s List studio as I talk to Ruth Winden about how to woo an interviewer half your age.

Ruth Winden is a career coach for professionals in their 50s, 60s, and 70s. She helps older workers overcome age bias and land new jobs with clarity, focus, and confidence.

Ruth is also the author of the forthcoming book, “101 Ways to Overcome Ageism in the Workplace.”

She joins us today from the town of Yarm, in the Northeastern part of the United Kingdom.

Ruth, thanks for being on the show.

Ruth Winden:

Thank you for having me.

Mac Prichard:

Well, it’s a pleasure. You know, our topic today is how to talk or how to wow an interviewer half your age when you’re a job candidate and you’re an older worker.

Let’s start, Ruth, by talking about the challenges older workers face when they’re talking to younger interviewers. What should be on the mind of an older worker when she or he walks into that room?

Ruth Winden:

The first thing I suggest to my clients is not to get too worried about the fact that, yes, there is age bias in the workplace and there is age bias with recruiters. We know it exists. But if you focus on that completely, then I think that you set up the interview in a certain way and it doesn’t do you any favors. So, that’s something, really, how do you feel about the interview, how do you go into it, is a really, really important starting point.

Another good thing to think about is, who are you likely to meet in the interview? Do your research, really understand the interviewer, his or her background, what they’re interested in.

You could do this with LinkedIn, you can do a Google search, but you really want to find out as much about the interviewer, and then find, what do you have in common? Because I think what I see is, if there’s a big age gap between the interviewer and the candidate, and it can sometimes be that they don’t understand each other or they don’t think they have enough in common, and it is, in my view, the job seeker’s responsibility to find out as much, so they can really show how much they understand the world of the other person and also they can connect and build that all-important rapport.

Mac Prichard:

I love the idea of doing the research ahead of time so you know who you’re going to meet, because sometimes, I imagine you’ve had this experience with your clients, Ruth, they walk into and they’re surprised by the age of the person they’re meeting and it shows on their face, doesn’t it?

Ruth Winden:

It does. Certainly, I also hear stories from my clients, and they say, “I went into the room and the interviewer looked really surprised because he seemed to expect a younger person.” That is always awkward, so it is really important that we find that connection, something to talk about, and show that we’re able to work across generations and we are. There are so many prejudices and biases out there, you know, we talk about the modern generation, the workforce, and that the young ones don’t get on with the older ones and I don’t see necessarily that much evidence of it, but it’s impressions that people might have and you just have to prepare yourself, “How can I connect?” And we say that to any job seeker at any age, but I think when we have more experience and we’re at a different generation than the interviewer, then it’s doubly important we really do our homework and show them we can get on with any generation, any age, any background, in the workplace.

Mac Prichard:

Well, let’s talk about the elephant in the room and that example where, you know, you’re an older worker, you walk into the interview room, and you can tell that the person you’re meeting with is indeed surprised by your age. How do you deal with that and particularly, the possibility that the person might be prejudiced against older workers?

Ruth Winden:

Yeah, I mean, it is a tough situation but I think what you need to do is really show them how up-to-date you are with industry trends, you really know your field, you are a very capable professional, you are up to date, you know, the latest technologies and all the latest approaches, the latest discussions. Older job seekers do, so bring your professional expertise to the fore and don’t let it intimidate you or put you off because it’s your opportunity and in a way, try and woo them, try and win them over by showing what a capable person and professional you are.

Mac Prichard:

Well, I want to talk more about how to woo the person. One thing I know older workers, and anyone in their career will do, is to talk about their years of experience. When you’re an older worker though, you have to be strategic, don’t you, about how you describe your experience? Just rattling off the number of years probably isn’t going to be persuasive, is it?

Ruth Winden:

But you see this everywhere. You look on LinkedIn and how many profiles do you see, 25 years, 30 years, 35 years, experience and I do understand, we have a lot of experience, we bring a lot of experience to the workplace, but what does that actually mean? And when you see the reaction of other people who might have an issue already with someone not of their age group, what does it say to them? It says, “Okay, you’re older. You have a lot of experience, you’re expensive, but are you actually up to date?”

For me there are two types of experiences; one experience is what I call “evergreen” experience. That is the experience that does not expire. It is a lot to do with interpersonal skills, managing people, dealing with conflict, managing mergers and acquisitions, all the things that are very, very skillful and that we have built over time and in a way you can argue, “We’ve seen it all. We’ve done it.” That is something that is never stopping to be relevant.

On the other hand, we have the technical experience. I call it “time-bound” experience because things change so rapidly. If you say, “I’ve got 30 years experience in marketing,” what does that actually mean? The interpersonal 30 years absolutely are paramount, but if you did marketing in 20, 30 years ago, it is completely different from now and so is the opposite, who might have been in marketing for five years, was it, “Hang on a minute, I can’t relate to that. What do you actually know about content marketing, about social media, about customer engagement?”

So for me it’s really important that, as for job seekers, to think, to differentiate, what is really of value to this employer and how can I show that I am really on top of things and I understand the latest concepts and I know everything about social media you would expect anyone working in marketing?

I think that’s a difficult concept for job seekers because understand, we’re so proud of the years, but the years don’t necessarily give the interviewer a very good indication of what you can actually do us.

Mac Prichard:

And what you need to do, I hear you saying, is focus on what you can do for the employer and talk and describe the skills and experience you have that are relevant. Just don’t talk about the numbers of years experience.

Ruth Winden:

Exactly. Bring in…you need to have all the metrics, all the right keywords, all the things that you would talk to a colleague, let’s say that it’s marketing, that you show that you really understand and can apply it and share your achievements and that’s what wins any interview. In my view, the age shouldn’t really factor in. The age is just a number, you know, but a lot of people get very hung up about that.

Mac Prichard:

Well, let’s talk about how to woo that interviewer, the person sitting across the table from you who might be 20 or even 30 years younger than you. What’s the first step, Ruth? How do you recommend people get started?

Ruth Winden:

I think doing the research is absolutely paramount. You want to know as much about the interviewer as they know about you, so, do your search. Also just understand the culture of the organization. If you’re going from a corporate background and you go into a startup, it is a completely different culture. How can you show that you fit in? That can really start from how you appear.

What is your dress code? If you’ve been in corporate, you won’t be used to certain dress codes but is that really the dress code that will show someone in a startup, “I’m one of you?”

Absolutely not. Really doing the homework and understanding, “Who am I meeting? What is the culture? What are their expectations?” That’s all the homework you need to do beforehand.

I think also, it’s really having a feel for, what is on the mind of 25-year-olds or 30-year-olds?

Those are the few who mix it up with younger people. I think it’s absolutely important that we really understand their worlds and can use language and concepts and have something to refer to that you have in common.

Mac Prichard:

Well, let’s talk about authenticity too, because, obviously, you want to be who you are, you don’t want to pretend to be something you aren’t. How do you recommend…what are some guidelines there, Ruth? Because you don’t want to come across as sales-y or not yourself. What are your recommendations?

Ruth Winden:

I would always say, I talk to a lot of young people, I was teaching some 25-year-olds today and I try to connect to see the world through their eyes and I’m still myself, but by bringing in certain topics or commenting on something or being a little bit more laid back, there are certain things that I think you just have to practice connecting to younger people.

Some of my clients are very good at that and some of them really have to make an effort because it’s not necessarily their norm or they might not have children or nephews or nieces or not be surrounded by many young people. It’s about connecting and listening and not putting on a facade. You can’t really pretend these things because the person will notice that straight away.

Mac Prichard:

What’s your top tip, Ruth, if you’re an older worker, to connect with younger people? How do you see people do that successfully and authentically?

Ruth Winden:

I think it’s really being not prejudiced and going in with an open mind and having done your research; it’s interesting, I have children, a 21-year-old, a 15-year-old, and they teach me a lot about young people and they also tell me when I become very old-fashioned and that is a very good measure of, you know, I look at some of the videos they watch and I listen to some of their music and I think anyone should do that anyway. Whether you are 50 or 30, we all work in different, across different generations.

We now have five generations in the workplace and I think it’s really coming with an open mind and understanding. Does that make sense, Mac?

Mac Prichard:

It does and I want to take a quick break right now because I want to talk more about what happens in that interview room after you’ve done that research and you’ve thought about how to make that connection. Stay with us, Ruth.

When we come back, Ruth Winden will share more of her advice about how to woo an interviewer half your age.

In November, I celebrated my 60th birthday. My Dad and my sisters threw me a surprise party. It was the first surprise party I’d ever had. And it happened at my childhood home in Iowa.

Needless to say, it was a special day. And I didn’t think twice about posting photos from the party on Facebook.

But I might not have shared those 60th birthday party pictures online if I were job hunting.

Too often, older workers like me feel we have to hide our age when looking for work.

And it’s no surprise why. Ageism in hiring may be illegal, but it also happens every day.

I’ve got a free guide that can help you beat the barriers older workers face. It’s called Fighting Ageism in a Job Interview.

And you can get it today. Go to

It’s against the law for an employer to ask how your age might affect your performance on the job. However, you still need to address those concerns.

So my free guide gives you the answers you need for the six most common misconceptions about older workers.

Get those answers today. Go to

Before you go to your next job interview, know how to talk about the taboo topic of age.

Go to

Now, let’s get back to the show.

We’re back in the Mac’s List studio. I’m talking with Ruth Winden. She’s the author of the forthcoming book, “101 Ways to Overcome Ageism in the Workplace”.

Ruth joins us today from the town of Yarm, in the Northeastern part of the United Kingdom

Ruth, before the break, we were talking about making those connections with younger people and ways that people might do that. Let’s go back to that interview room; you’ve done the research, you’ve thought about how to make those connections, you’re looking for something in common with your interviewer. Let’s talk about confidence, Ruth. How important is that for a candidate, particularly one who is seated across from someone who’s much younger than themselves?

Ruth Winden:

Just to check, you said confidence, Mac?

Mac Prichard:

Yes, confidence.

Ruth Winden:

I think the confidence really comes from knowing what value you add to an organization and how you bring that across and how you engage and how you signal that, “I understand the world of the interviewer and the world of the employer.”

Mac Prichard:

So, it’s doing the research, walking into the room with that understanding. What kind of difference can having that kind of confidence make in the outcome of the interview, particularly when connecting with a younger person?

Ruth Winden:

I think that young people want to have the confidence that you fit in because they might have their own idea about what older workers are like. Really showing that you understand the organization and how you can add value, how you work, what you’re looking forward to, what you bring, and also bring in an examples that show that you have experience of working across different generations or, for instance, you might have done reverse mentoring, where you help sort out the input and the mentoring of the advice from a younger person. That really signals very strongly that you’re very open-minded and that you are humble and you don’t have any issues with connecting with younger people and seeking their advice, because it’s always a two-way street.

Traditionally, for instance, mentoring has always been to go to the older person, the more experienced person, but let’s face it, some of these younger people really know a lot more about certain aspects than we do. Signaling that willingness to learn from each other and also, you know, some of the wisdom that we bring, some of the highly-skilled negotiation techniques, or mergers, you know, we have a lot of experience doing business that we can help them with.

That’s where the experience, the management experience and the interpersonal experience, comes in, which is so important because we have that valid, solid foundation, and that’s what we can bring in.

Mac Prichard:

I like your example of sharing stories about how, as an older worker, you’ve had younger mentors, and what especially appeals to me about that, Ruth, is because it shows that you’re a lifelong learner, doesn’t it? And that’s always appealing to employers, isn’t it?

Ruth Winden:

Absolutely. Yes, and I do this myself. I sought out a younger mentor in the social media field and she’s only 26 and she achieves amazing things, and I have got a lot to learn from her and it makes me appreciate how much knowledge young people have, that their approach might be different and  I learn from that. It’s great fun for me, it’s very humbling, and it’s also nice for the younger person because they feel very recognized and they feel, “Wow, you know, this woman has got 30 years more experience in something, but she listens to me.”

I think it’s a really beautiful synergy that can come from the reverse mentoring, and here in the UK, we certainly see more efforts in putting this into place in the workplace because it is so good for the intergenerational relationships that we all need to master, now that we have the workplace with 5 generations.

Mac Prichard:

The workplace certainly has a lot more variety, in my office, there are 4 generations represented. I’m the only Boomer and I’m always learning from my colleagues, the majority of whom are Millennials, but they teach me new things every day.

I think also, another benefit of sharing stories like that with the younger interviewer, is that it addresses a misconception out there about older workers. That older workers just have stopped learning and they’re just looking for a place to coast until they can begin collecting some kind of pension benefit.

Let’s talk about, related to confidence, Ruth, how do you coach people who are older and have been looking for some time and they’ve had a lot of setbacks and, frankly, they’re feeling discouraged and sometimes they bring that discouragement into the interview room? What are your tips on how to overcome that?

Ruth Winden:

I think the first thing is really recognizing it. I mean, you go on Twitter, and I see all these negative comments all the time and I do understand, it is extremely frustrating when you go to interviews and you’re a capable candidate and you feel there’s this elephant in the room and they might look surprised. Some of my clients say, “They even said to me, ‘We were expecting or we were hoping for a  younger person.’”

That really hurts because it is totally unfair, but I think people need understand, if that’s going on, you need to really get out of that. You need to, because if we expect to be treated like that we behave differently and so, for me, a big part is really, first recognizing, “I have built up, because of the rejection, I have built up a negative view and I take it with me and it stops me from being my real self.” That’s number one.

When it happens, it’s really, how can you push those experiences to the side and focus on, “Okay, how can I portray myself positively, how can I connect?” It’s difficult, but every time you have to try again. Put things behind you and treat it as the most important opportunity to put yourself in front of an employer and show them what you can add.

I think that’s where the coaches come in, because when we look to our family or friends, everyone’s like, “Yeah, it’s ageism, it’s ageism, you have no chance.” That really undermines us. When you look at the facts, the older worker population is growing in terms of returning or staying in the workplace. You look at the numbers and the numbers are up and they’re up quite dramatically, so there are a lot of people who are constantly succeeding at this and so, let’s get out of this, “Oh everything is ageism.” Sometimes it can just be that you are the wrong candidate or you don’t have right skill set. It happens to everyone, so, de-personalizing that rejection of things is really, really important.

Then, the next step for me is really helping clients, okay, let’s focus on the positives. Let’s focus on the value that you are. Come with some ideas and be prepared that they might give you some challenging questions. Don’t get defensive, you know, when people say, “So, how do you think you can work with the younger generation?”

Some people read this as a criticism but I do think it’s a legitimate question and if we find good answers for that and we can think these things through, either by preparing well or working with someone else on this, I think it can really add a lot of value. You want to go in there and have a really good conversation and be prepared that, yes, some questions, you might think they’re loaded but if you go into thinking they’re loaded, you will give a very defensive answer and I think that’s a danger.

Mac Prichard:

I like your advice to be prepared for a question like that because sometimes these questions are never asked, like, “How might you work for people of a younger generation?” But they’re definitely on the minds of the hiring managers, aren’t they?

Ruth Winden:

Absolutely, and sometime I’ll even say to my clients, depending on what the atmosphere is like, and that is always a judgment call, sometimes it is the right thing to, you know, bring it up and say, “We had a great conversation. Is there something that is of concern to you?” Of course, they can’t say in the interview, “Well, it’s your age.” But I think sometimes bringing it up, or you can ask questions about, “How does the organization…what strategies are there to bring the generations together to talk to each other?”

You’re lucky in the US, you have the AARP,  lists of 700 age-friendly organizations in the US, and I would, as a candidate, really want to talk about the culture and how does it manifest itself and how do you support that? All the different generations could make a contribution.

Mac Prichard:

Well, you mentioned earlier a suggestion that job seekers look for companies that hire older workers and I know just a moment ago, you mentioned the AARP list of age-friendly employers. Are there other strategies that you suggest to listeners to find companies like that?

Ruth Winden:

I would definitely, you know, we all have connections, we have good networks, that’s another benefit we bring when we’ve been in the workplace for a while. I would definitely find out and talk to people. I would do LinkedIn searches and see, you can find out on LinkedIn, roughly at least, if someone’s in their 40’s or 50’s or 60’s or 70’s and reach out to them and say, “I saw that you work for my dream employer. Would you have 15 minutes of your time? In confidence, can we talk about something that I’m concerned about? How do they see older applicants?”

It’s research through the lists like AARP, or the Encore, or, you know, you have so many organizations in the US. Then, I would definitely say, do some research on LinkedIn and use your networks and ask around. I follow a lot of the media on Twitter and there’s a fantastic community in our space for older workers, and if you look out for those organizations who do a lot of research… In the UK we have Business in the Community and Aging Better. They work consistently with employers. I think there is a big change coming, and I think more and more employers, because of the demographics, realize, “It’s a tight labor market and we can’t find enough people. Let’s be more inclusive and also look at candidates we might not have looked at so much in the past.” I think this explains why we have such success rates with older workers now. Much more than in the past.

I think the time has come where our chances are becoming more equal, whether that’s because of demographics or policy changes. I’m a pragmatist. I don’t care. I want my clients to get great opportunities and I think it is shifting.

Mac Prichard:

Well, thank you, Ruth. It’s been a terrific conversation. Now, tell us, what’s next for you?

Ruth Winden:

I’m working on my book, “101 Ways to Overcome Ageism in the Workplace” and that’s been inspired by my clients. You’ll obviously hear a lot of anecdotes, what they struggled with, what has been in the way for them, what have been the barriers, and I want it to be a very pragmatic book. It will be 101 strategies, tips, little examples, so it helps people to really maneuver the job search in your 50’s, in your 60’s, and in your 70’s and I can’t wait to get it out into the big wide world, Mac.

Mac Prichard:

Well, I look forward to reading it. I know you plan to publish it in the summer of 2019.

Ruth Winden:


Mac Prichard:

I also know people can learn more about you and the work you do by visiting your website,

Ruth, thanks for being on the show today.

Ruth Winden:

Thank you very much, Mac.

Mac Prichard:

You’re welcome. Take care.

The most important point for me in that conversation with Ruth was about the importance of preparation. You have got to do your homework before you go into an interview room.

Now, Ruth was coming at this topic from the point of view of someone who is helping an older worker make a connection with a younger interviewer, and obviously one of the benefits of doing your homework if you’re an older worker is you will not be surprised if you walk in the room and the person you’re meeting is 25 or 30, when you’re in your 50’s or even your 60’s. Take that lesson to heart.

Do the preparation. One of the tools that we have that can help you get ready is a new guide; it’s called, How to Fight Ageism in a Job Interview.

It gives you practical tips about how to get ready for your next job interview, and how to overcome those negative stereotypes employers have about older workers.

You can get your copy today. Go to

It’s free;

Thanks for listening to today’s episode of Find Your Dream Job.

Please, join us next Wednesday. Our guest expert will be Stephanie Smith. She and I will talk about back to work strategies for stay-at-home parents.

Until next time, thanks for letting us help you find your dream job.