How to Talk About Bad Work Experiences in a Job Interview, with Stephanie Heath

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Find Your Dream Job, Episode 360:

How to Talk About Bad Work Experiences in a Job Interview, with Stephanie Heath

Airdate: August 10, 2022

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 you find a fulfilling career.

Every Wednesday, I talk to a different expert about the tools you need to get the work you want.

Find Your Dream Job is brought to you by TopResume. TopResume has helped more than 400,000 professionals land more interviews and get hired faster. 

Get a free review of your resume today. 

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Have you ever had a terrible boss? 

Or worked in a toxic office? 

You never want to trash talk a former employer. But sometimes, you need to be candid with a hiring manager.

Stephanie Heath is here to discuss how to talk about bad work experiences in a job interview.

She’s a job search advisor, a salary negotiation expert, and the founder of SoulWork and Six Figures. 

Her company has helped hundreds of professionals find their dream job while often doubling their salaries. 

She joins us from New York City. 

Well, let’s jump right into it, Stephanie. How common is it for workers to have had bad experiences in the workplace? 

Stephanie Heath:

Very common. I’d say hiring managers, founders, your peers- if you speak to any of them, they’ll say that you know they’ve either been laid off or let go or failed in some way at work. So it’s extremely common. 

Mac Prichard:

In fact, I know you’ve got a list of four kinds of bad work experiences. Can you walk us through those quickly? 

Stephanie Heath:

Yeah, absolutely. So, I’d say the first is a professional that was laid off or let go. The second could be some sort of harassment; we’ve seen that happen before. The third, most recently, is just someone leaving due to COVID policies or potentially a culture that wasn’t inclusive. And then, maybe another could just be folks wanting to work in a more hybrid environment or having a company that’s still, you know, just having sort of outdated work, busy work policies if that makes sense. So, those are some common reasons people aren’t really comfortable on how to describe when they’re on the interview, so. 

Mac Prichard:

And when someone is looking to make a change, and they’re getting ready to start a job search, how have you found that those bad experiences can shape their job search? 

Stephanie Heath:

It definitely colors it. I would say that, you know, you’re bringing that fear into the interview, and even though you’re answering questions, the interviewer can potentially sense that there’s something that you’re not disclosing. So, you know, we’ve had candidates get to maybe the third round or the final round, but the company will end up hiring someone else just because that little sort of twinge of distrust, and not being able to see the candidate for who they are fully, and so they’ll go in a different direction. So it really does affect someone’s search. 

Mac Prichard:

We’ve all heard the advice never trash talk a past employer. Why do you need to talk about bad work experiences at all? Isn’t silence just the best policy here? 

Stephanie Heath:

I would say silence can be the best policy if it’s not a, you know, and excuse my language, just a huge issue. But like I said, anyone that’s in a position to hire typically, quote-unquote, people-people, and we can just sense that there’s something you’re not disclosing. So, for most of the candidates that we assist, I would say maybe seventy or probably close to eighty, eighty-five percent of them, we’ll have them talk through a negative experience and then just give them language to share it in a professional way versus just having them not talk about it at all. 

Mac Prichard:

What mistakes do you see candidates make when they do talk about bad work experiences? 

Stephanie Heath:

Number one would be just not taking ownership of the part they played. So, we’ve all had managers that, you know, potentially weren’t the best manager. Right? They still had some work to do to develop into a people manager. But I would say that each employer wants to hear, you know, how you would approach the situation differently in the future, what you learned from it, and just having you take ownership because once you’re employed by that company, you’ll have people that you need to work with that potentially aren’t as developed or emotionally mature. So, they want to know that you’re able to handle any situation that arises. So, definitely being able to take ownership, that’s probably the first one. 

Mac Prichard:

And how do mistakes like this happen? Is it a lack of preparation? Are candidates surprised to get these kinds of questions? 

Stephanie Heath:

So, yes. It’s definitely the surprise. But also candidates are just having this, they’re weighed down by either feeling guilty or, you know, they should have done something differently, and instead of just looking at the experience as, this was a challenge that I went through, and this is how I would move forward in the future, they’re letting the negativity of the situation, sort of, color how they’re viewing it and approaching it. And so, they communicate that way with an employer, and like I mentioned, we all go through moments where we’re challenged, or we make a mistake, and so it’s just best for you to be able to really resolve it internally and emotionally, and then enter the interview process, and kind of communicate what happened. 

Mac Prichard:

In your experience working with candidates, getting them ready for interviews, do you find that many employers will ask directly about bad work experiences? Or are they looking, as you mentioned earlier, for just signs that someone might not be forthcoming? 

Stephanie Heath:

I would say there’s maybe one or two key questions that will open up the Pandora’s box or just kind of lead into learning more about what happened in the last role. The first one would just be, you know, tell me about your current position. Why are you looking to leave? And then, like I said, when you’re describing the role, if you’re giving big answers, you know, like, I’m looking for more of a challenge. Yeah, basically, I would say that that’s the most common. I’m looking for more of a challenge. 

A recruiter or a hiring manager or finder will kind of dig into that more. So, tell me about your day-to-day. What was it like working with your manager? You know, what was a challenging, you know, experience that you had there and you overcame? 

And so, they’ll just have a few different follow-up questions that will unearth, you know, potentially you weren’t getting along with your manager, or you may have made a few different mistakes and were let go. And so, that’s when, you know, that will arise, and it’s just really important for someone to feel okay with what happened and communicate how you would approach it differently in the future and take that ownership. 

Mac Prichard:

And what’s striking about the point you’re making here, Stephanie, is the question that you’re sharing is a very common one. Why are you leaving your job? And, you mentioned that employers are paying attention to that answer and looking for signs that something might not be right, perhaps, by withholding information. Are there other signs that employers are paying attention to when a candidate responds to that question? 

Stephanie Heath:

Yeah, more so. It’s not so much what you’re saying but what you’re not saying. How vague your answers are and your body language and your voice tone as you’re, you know, talking about that experience. If you’re giving, you know, a vague answer, and, you know, it’s short, succinct- especially, if you’re interviewing with companies that are really competitive- you’re gonna have to maybe speak to six or seven different people during the interview process, and they’ll all be asking you that question in different ways. 

So, we’re all just gonna be able to tell that there’s something you’re not really talking about, and usually, nine times out of ten, it’s not as bad as you think it is. So, it’s just better for you to just talk about it during your interview versus hiding it. 

Mac Prichard:

Well, let’s talk about how to talk about it. I know that when you work with your clients, one of your first recommendations is to vent before you go to an interview. What kind of venting are we talking about, Stephanie? 

Stephanie Heath:

Yeah, so let’s say you feel as if something unjust happened to you or, you know, something wasn’t your fault. We’ve all been there. It’s good to get the perspective of someone else. For me, I always recommend- try to speak to someone that was in your work environment. So, potentially, a colleague from a different department. But just someone that was there. Right? So, they saw what happened and get their perspective. Share, you know, how you felt it went, and then see if they can maybe negate it. Say, oh no, you’re beating up on yourself, you know, that’s not how I viewed you. 

A quick example could be when I was a recruiter, I was let go from one of my positions, and I got coffee with a business partner of someone who was head of their department just to kind of talk through what’s happening and maybe get some leads, and I shared how I embarrassed I was and just how I felt I should’ve done a better job. And she was just like, “You know, Stephanie, you are the best recruiter I’ve ever worked with, and I’ve worked for several different companies. You care so much.” And she laid out all of these, you know, aspects of my personality and how I performed at work that I hadn’t even thought of. And after that conversation, I immediately switched gears with my next interviews. I was a different person. 

So just being able to kind of speak to someone that can clarify some things for you. And then, on top of that, maybe even taking a session with a coach to coach you on how to communicate, you know, where you were at fault using language that’s not emotive, and like I said before, taking that ownership. 

Mac Prichard:

Can venting backfire? Do you find that people sometimes just get stuck in a place of unpleasant feelings? 

Stephanie Heath:

They can. So, the point of venting is to release whatever negative energy you have or an opinion that you have towards the work that you completed within that company. So, being able to view it in a different way. So, like I said, the point to venting is to release it and to have a new, fresh perspective, and when you get on that next interview, when they’re asking you what happened in your last role, or just tell me about your last manager, you don’t have that sort of sticky resentfulness and bitterness, anger in your body. It’s just like, oh, you know, X, Y, Z, happened, and I learned in this way, and moving forward, these are the questions I would ask in the interview to make sure that I’m not in that situation again. 

Mac Prichard:

Well, Stephanie, we’re gonna take a quick break, and when we come back, I want to talk more about who you should reach out to to talk about bad experiences. 

So stay with us, and when we return, Stephanie Heath will continue to share her advice on how to talk about bad work experiences in a job interview. 

You need to talk about every job on your resume, even when you had a bad experience.

Make sure you’re telling your career story as well as you can.

Go to macslist.org/topresume.

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Go to macslist.org/topresume.

Learn how you can make your resume better on your own. 

Or you can hire TopResume to do it for you. 

Go to macslist.org/topresume. 

Now, let’s get back to the show.

We’re back in the Mac’s List studio. I’m talking with Stephanie Heath. 

She’s a job search advisor, a salary negotiation expert,  and the founder of SoulWork and Six Figures. 

Her company has helped hundreds of professionals find their dream job while often doubling their salaries. 

She joins us today from New York City. 

Now, Stephanie, before the break, we were discussing how to talk about bad work experiences in a job interview, and we were talking about venting. 

And one thing I want to explore more is, when you’re getting ready to discuss a bad work experience in an interview, I know that you recommend that you practice your answer with someone you trust. What kind of practice do you recommend? And how do you find somebody who can help you with this? 

Stephanie Heath:

Yeah, so I recommend switching over or changing some of the emotive words you would use to describe what happened into just objective language. And the person that I would suggest that you meet could be someone that’s more senior in your role, a mentor that’s not in your industry at all, or a career coach, and then maybe lastly, someone at your old company that you could trust. That, you know, wouldn’t share anything with anyone. 

Mac Prichard:

What kind of questions do you recommend preparing for? Do you have a short list, Stephanie, of, say, your top three questions that you need to get ready so that when bad work experiences come up, you know how to use that language that you discussed?

Stephanie Heath:

Yeah, so I would suggest starting from the tell me about your last role and why are you looking to leave. Those two questions, you would start there and then just mock interview with, like I said, a mentor or a friend, and just have them kind of dig in a little bit. 

So, you know, tell me about your last role. “Oh, I was responsible for X, Y, Z, and you know, I’ve decided that I’m looking for a new challenge.” 

“Oh, okay, you know, what challenges are you looking for that you aren’t able to kind of experience at, you know, X, Y, Z, name.”

“Oh, well, you know, at my current company,” and then so, you kind of do that piggyback sort of mock and just keep going, you know, deeper and deeper into like the crux of the issue and then making sure that as you’re describing, you know, my manager’s communication style was a bit different than I expected or was just a bit different from me, or their expectations are different than what the job description disclosed. 

Using that sort of objective, blaming it on, you know, the situation versus saying my manager was overly aggressive with me, and, you know, my nervous system got shot because of it. So you would start there. 

Mac Prichard:

And in preparing and practicing these answers, do you have recommendations about length of response? Is it something you just acknowledge briefly and then pivot and turn to another subject? What have you found to be most effective? 

Stephanie Heath:

I think that’s a great strategy, and I’ll also just share that when you are interviewing with competitive companies, like Goldman Sachs or Meta, you know, you are gonna be interviewing with maybe eight people. So, you can have that strategy of just keeping it more succinct. But just know that, likely, the story will come out anyway. So, keep that in the back of your mind that, you know, don’t go on a rant. But also, just get comfortable with sharing what happened. 

Mac Prichard:

And, how much preparation do you recommend? You find the mentor. You have this short list of questions. You do rehearsals and get feedback from your practice partner. Is that sufficient to get you ready to go into the interview room? 

Stephanie Heath:

I think so, and I think prior to COVID, for some reason, I don’t know why, but prior to COVID, I think the job market was pretty normal. So, you could say, you know, I’m ready to enter the job market, and maybe take about a week to sort of rewrite your resume and to write down all of your wins and accomplishments that you can bring. You could share those stories during your interview. 

But now I am advising that people take even maybe a month or four weeks before, you know, updating your resume, and updating your LinkedIn, and starting any applications to really get familiar with your stories. To look at an ideal role, maybe a job description and have a story or an example to speak to each bullet point so that, you know, if you’re pivoting into a new role or you haven’t interviewed for a while, you get rid of those nerves, and you know how to communicate your answers. You have that practice, and maybe even memorizing, you know, forty percent of the questions that you expect to be asked. 

So, I definitely, you know, suggest taking a longer time now, and we can maybe share more about why. But that is kind of most of it. Just it’s what I recommend now. 

Mac Prichard:

And tell us why. What has changed? Why do you recommend investing more time- up to a month- and getting clear about what you want and understanding job descriptions, and preparing your interview responses? 

Stephanie Heath:

Yeah, so I would say this could just be because of the clients that we see. Most of the candidates or clients we see are looking to either pivot into a new role, new industry, maybe interview into their first director-level position or managerial position, or are just completely reinventing their career. 

So everyone that we speak to are really in an introspective stage of their life, and so they want to put their best foot forward and really take their job search slowly, intentionally, and seriously. So, now it’s important. I do suggest that before you apply, just get really comfortable talking about your current role. 

Know how to ace, and just, you know, spout off like off the back of your hand, those common interview questions. Tell me about your current position. Why are you looking to leave? You know, be able to speak to the intricacies of your role. And then, you know, show up authentically during your interviews. 

And so, when you’re asked some questions that you can’t prepare for, you would at least have those great answers for seventy percent of the questions that come up. So, yeah.

Mac Prichard:

Terrific, and I know in thinking about those answers, other steps that you recommend include breaking down your answer. How do you suggest that a candidate break down an answer when they’re preparing for a response to a question about a bad work experience? 

Stephanie Heath:

Right. So, the easiest way is to use the STAR method. So, let’s say you’re sharing an example; you would want to, you know, quickly summarize a situation, the task, what was your action, and then the result. And then, since we are talking about experiences that aren’t the best, potentially, definitely remember to not use emotive language. So, don’t say, I feel like, or I was angry and I just. You know what I mean? Just really, again, separate yourself from the situation and just describe what happened. That environment turned out to not be the best for me, and just my communication style, and so in the future, I would be looking for blank, you know. 

And I do want to give one more example if possible. One of our clients, yeah, she said her voice was never heard during her meetings and that her voice was never heard. So, we suggested that she would share, “I’m looking for an environment that has more of, sort of, a round-table decision-making culture.”

So that could be a way to kind of describe, you know, being talked over in meetings and not being taken seriously. 

Mac Prichard:

And how did you help her prepare to use her voice and to make sure that she was heard? 

Stephanie Heath:

So number one, we made sure that she got clear about what she was looking for in the future. In this instance, it was round-table decision-making. If you’re soft-spoken, if you’re not someone that raises your hand for everything and waits and doesn’t quite jump in, you know, sussing out if your future colleagues and hiring managers have that same personality type or that’s kind of the culture where, you know, like I said, people aren’t jumping over each other, and they’re not really using excessively aggressive language. It’s just like, okay, well, let’s go around and ask, you know, what your opinions are, and what your recommendations would be. 

So, getting clear about what your non-negotiables are, writing them down. You can maybe stick to five. Round-table decision-making could be one. Another could be hybrid work culture. Another could be a manager that, you know, respects my decision-making. And then, crafting, not necessarily sneaky interview questions, but crafting questions to suss out if that’s that company’s environment. 

So, for example, that could be, when we craft those questions, we like to call it, giving them the either/or. So, for example, you could say, you know, I’ve worked in environments where you really had to have a strong voice to push your thoughts and suggestions forward, and I grew a lot in those environments, and I’ve also worked on teams where everyone was a bit quieter and more thoughtful, and so it was more, just everyone has a voice, and I really kind of respected that, as well. And so, what would you say that the environment is like here? 

So, if you pose that question to your potential new peer or your hiring manager, neither answer is wrong, and they’ll just tell you the truth, and you can either say, okay, this is probably the environment for me, or you know, they’re gonna be maybe a C opportunity versus being at the top of my list. 

Mac Prichard:

I like that example a lot because you’re giving the candidate the tools they need to find the work experience they want so they can move away from an environment where they not only didn’t thrive but it wasn’t pleasant for them. Are there other tools like that that help the people you coach accomplish that? 

Stephanie Heath:

Yeah, and so I guess because we are focused on helping folks that really are obsessed and, you know, this next role isn’t just a paycheck. They want fulfillment from this next opportunity. So, we suggest slowing your search down, maybe not entering the job market for a while. Asking yourself, what makes you happy? What are you good at that you want to keep doing? What are you good at but you don’t want to do anymore? You know, going through a list of those questions. We have a PDF on our website that’s free. You can download it. It’s called the Market Value Guide. 

And then having that practice of grabbing maybe two ideal roles and going through the responsibility section and having an answer to each bullet point. Something that, you know, lights you up, you feel comfortable sharing. And then, practice answering the question a few times so it sticks into your memory. 

And then, not being afraid to ask those sneaky questions in an interview and really tuning into your gut. So, how am I feeling talking to this person? How am I feeling talking to the next person? You know, am I comfortable with sixty percent of the people that I’ve spoken to so far? How are they treating each other? You know, what do I feel throughout this entire experience? 

You could journal about it, so you can keep notes. You can create an Excel doc. So, it’s like, okay, you know, this is likely matching up with what my ideal role would look like, or it’s kind of similar. 

And then, not being afraid to ask certain questions that, you know, in the past, potentially, someone would save for the end or just not ask at all. Potentially, around salary and bonus, and again, you know, really asking for that hybrid work schedule.

And then, the very last tip would be just to be really brave and comfortable asking for the top of the range. Even if it’s thirty thousand or forty thousand or fifty thousand more than what you actually need or want. Just so that when they negotiate you down, you’re still in a good place. And that sort of experience grows you. Yeah. 

Mac Prichard:

Terrific. Well, Stephanie, it’s been a great conversation. Now, tell us, what’s next for you? 

Stephanie Heath:

Yeah, so we’re always focused on our signature program, the Career Catalyst and the Six-figure Catalyst. We’ve since launched it as a ten-week model, and now we have a five-week model for someone that wants to get ramped up quickly. 

Mac Prichard:

Well, terrific. I know that listeners can learn more about you and your programs by visiting soulworkandselfies.com/catalyst. We will be sure to include that link in the podcast newsletter and the website article about your episode. 

You also invite listeners to connect with you on LinkedIn, and if they do so, I hope they’ll- encourage them to include a note and mention that they hear you on our show. 

Now, Stephanie, given all the great advice you’ve shared today, what’s the one thing you want a listener to remember about how to talk about bad work experiences in a job interview? 

Stephanie Heath:

Definitely disclose what happened because, again, we’re gonna figure it out. We’re gonna figure out that there’s something that you’re not sharing. Use objective language. Show how you’ve grown, even if, you know, you weren’t at fault. Take ownership, and, you know, stand in your truth. Your ideal role isn’t gonna pass you by. So each individual interview that you take, don’t put too much pressure on it. You’ll get there. 

Mac Prichard:

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Next week, our guest will be José Miguel Longo. 

He’s a career and life coach who helps Millennials achieve meaningful and successful careers while gaining clarity and purpose in life. 

José Miguel also hosts the podcast, Coaching for Millennials. 

You’re likely to switch careers several times. 

But if you’re in your 30s or even 40s, you may be getting ready to do this for the first time. 

Join us next week when  José Miguel Longo and I talk about five steps Millennials – or anybody else – can take now to change careers.

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

This show is produced by Mac’s List. 

Susan Thornton-Hough schedules our guests and writes our newsletter. Lisa Kislingbury Anderson manages our social media.

Our sound engineer is Matt Fiorillo.  Ryan Morrison at Podfly Productions edits the show. Dawn Mole creates our transcripts. And our music is by Freddy Trujillo.

This is Mac Prichard. See you next week. 

There are many reasons you may have had a negative work experience; the question is, how do you communicate it to a hiring manager without sounding vindictive or like you’re hiding something? Find Your Dream Job guest Stephanie Heath says it’s crucial to be honest because the truth will come out. Stephanie suggests owning your part, not over-sharing, and venting with a friend before an interview. Spend more time focusing on what you want from your next position than you spend on what was wrong with the negative experience you had. 

About Our Guest:

Stephanie Heath is a job search advisor, a salary negotiation expert, and the founder of  SoulWork and Six Figures.

Resources in This Episode: