5 Questions to Ask Before You Make a Career Change, with Kelli Thompson

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How do you decide whether to stay at your company or look for a position elsewhere? It all boils down to a few simple questions, according to this week’s Find Your Dream Job guest, Kelli Thompson. Do your values match those of the employer? Are you excited to get to the office every day? If not, have you discussed your needs with your boss? Kelli recommends doing what you can to change the environment before choosing to leave it. State your needs clearly and set boundaries around time and expectations. And finally, trust yourself to know what’s best for you.

About Our Guest:

Kelli Thompson is a leadership and career coach. Kelli’s mission is to help women advance to the rooms where decisions are made. She’s also the author of  Closing The Confidence Gap: Boost Your Peace, Your Potential & Your Paycheck

Resources in This Episode:


Find Your Dream Job, Episode 372:

5 Questions to Ask Before You Make a Career Change, with Kelli Thompson

Airdate: November 2, 2022

Mac Prichard:

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Since the start of the COVID-19 pandemic, you may have thought about quitting your job and even changing occupations. 

But how do you know it’s time to stay or go, give your notice, and start a new career?

Kelli Thompson is here to talk about five questions to ask before you make a career change.

She’s a leadership and career coach. Kelli’s mission is to help women advance to the rooms where decisions are made. 

She’s also the author of Closing The Confidence Gap: Boost Your Peace, Your Potential & Your Paycheck. 

Kelli joins us from Omaha, Nebraska.  

Well, let’s get started, Kelli. 

You’ve got five questions you ask your clients to answer before changing careers, and we’re gonna walk through them each in a moment, but you designed these questions to help career changers understand their values, know what matters to them, and find work that aligns with their values. 

So let’s talk about those subjects first. Why, Kelli, is it important to know your values when you’re considering whether to stay or go from a career? 

Kelli Thompson: 

That’s such a good question because I think one of the things that happens is that we stay at organizations that our values don’t align. And I think the best way is just to give a personal example, and I’ll talk about myself, I’ll talk about my clients. 

But I was with an organization for twelve years. Wonderful organization, pillar of the community. They were a place that everybody wanted to work for, and they were a great organization, but I couldn’t understand why I wasn’t happy, why I wasn’t feeling fulfilled, and even though I had the job and the title that I wanted, it just felt like I was pushing a rock uphill every day, and I was feeling frustrated. I was feeling resentful. And one of the things that I discovered was that you know what, maybe this organization and I value different things. 

I worked for a bank. A great bank. But one of the things the bank valued was, you know, steadiness. They wanted to make sure that they were compliant of everything. They wanted to pass through things, through six rounds of approval because that’s just how banks operate, and here I was. 

I was somebody who realized I value creativity. I want to be able just to test and learn things. I want to be able to try things, and you know what? This is just not who the bank is going to be. Banks are gonna bank, and they’re gonna run, you know, in compliance, and they’re going to want a lot of approvals for things, a lot of standardized things, and that’s just not the way that I wanted to work. 

And so, my point in why it is so important to discover your values is you can work really hard at climbing that career ladder only to get to the top and realize, oh my goodness, I think this ladder is against the wrong building, and it’s something I’m just not gonna rectify, because what the organization values and, in my case, it was, consistency, adherence, compliance, is just different than what I valued, which was creativity and innovation and pushing things forward and testing and learning. 

And so, it’s so important to discover your own values and to determine if they match your organization’s values. Because if they’re not in alignment, it might be really hard to find some long-term career satisfaction when you’re working in different directions. 

And if they do match because I know I have, and some of my clients have had, organizations whose values match, when the tough times come, they’re a lot more endurable because our values match. And so, you know, we can have challenges, but we’re getting through them because we’re focusing on the same things. 

Mac Prichard:

What happens, Kelli, if you attempt to make a career change and you’re not clear about your values? 

Kelli Thompson: 

Such a good question. You know, one of the examples I would love to give is, you know, one of my clients was really just frustrated with her career, and I think we can all put ourselves in those shoes when we are at the fed-up moment, and we just want to get out, and we just need to find something different. And so, we just take the first thing that’s offered to us; maybe it has a great title, a great salary, and it’s mildly interesting to us. 

But when we make the move, and we don’t move in alignment with our values, one of the things that can happen is we just end up recreating all of that old dissatisfaction that was in our old job, and we go to an organization that continues to be a mismatch. 

And so, here we are trying to do work the way that we want to do work, and maybe we’ve showed up in the interview process being who we think we need to be to get hired, and then they hire the pretend us. We get there, and we want to start to relax into our roles and have fun and do things we love to do. But when the values don’t match, then all of a sudden, we find ourselves in that exact same predicament again. 

And I’ve had clients go through this, where they’re at the other end of three or four failed jobs, and they just can’t figure out why, and I know, with one specific client, I know, one of the things that we really dug into was, oh my goodness, I’m sitting here going to all of these different organizations who maybe are very strict, very rigid, very process-oriented, and here I am, I’m somebody who loves to go into an organization and shake things up and be creative and we were just never going to be a match. 

And so, that’s why it’s so important, so that we don’t go to the next organization and recreate all of the old drama and old habits and old dissatisfaction and resentment that we had in our prior career. 

Mac Prichard:

When you’re considering a career change, it’s very common to ask colleagues, friends, and family for career advice. 

What happens if you’re not clear about your values when you get that advice? Can you act on it properly, Kelli? 

What do you see happen with your clients who are getting coaching from colleagues but still aren’t clear about their values? 

Kelli Thompson: 

Oh, such a good question. You know, we’re gonna get a lot of well-meaning advice, you know, especially, I, in my work with women; women get a lot of well-meaning advice. I know I got well-meaning advice, even from my parents, from my early leaders about, oh, Kelli, you should do this. You should work for this type of organization. They’re very stable. They’re very steady. You’re gonna get great benefits. You’re gonna climb the ladder. We all love to give advice. Let’s just be honest. 

But what happens when we aren’t clear about our values is we tend to fall for anything. We have no barometer by which we can take in that advice and say, is this advice right for me? 

I have a client, she works for a benefits technology organization, and she is just brilliant. She’s so bright. She’s so creative. She gets work done. She’s the type of person that everybody loves to work with, so when projects come for the organization, guess who they want on their project team. They want her because she’s a high-achieving person. 

And one of the things that she found was, of course, she’s getting lots of advice. Hey, you know, Julie, you should go for this job. You should consider this. This position is open. And so, eager, young in her career, she’s like, yeah, that sounds great. Because I think a lot of the things that happen is we start to get starry-eyed about titles and salaries. 

But now that her and I are working together, she’s exhausted. She’s burnt out. She’s resentful. She’s just simply confused. She goes, I don’t even know what I want. And one of the things that we uncovered was, you know, through her career, she just took a lot of folks’ well-meaning advice. Because yeah, it seems good. Yeah, that would be a promotion. That would be more money. That would be more. It does sound fun.

But she never stopped to ask herself, is this what I truly want? Am I going to be doing things in the role that I value? For example, she just is a get-stuff-done sort of person, and one of the things she’s recognized is she values efficiency. She values effectiveness, performance. She actually doesn’t really love managing people. You know, it’s not that she doesn’t love people, but she’s just recognized that’s just really outside her skill set, and it’s just outside of her values system, and that’s causing a lot of disconnect right now. 

So I think it’s so important to be clear on what you stand for, what you want because otherwise, we get to take a lot of well-meaning advice and just tend to fall for anything because it looks right and not because it is right. 

Mac Prichard:

The second subject you encourage your clients to explore when considering a career change is to know what matters to them. What stops job seekers and career changers, Kelli, from thinking about what matters to them personally when they’re thinking about making that next move? 

Kelli Thompson: 

I think it’s just a lack of stopping and reflecting. We’re so busy. You know, I think we live in a hustle culture, where there are certain things that are prized in the workplace. Getting things done, how many hours we’ve worked, how many people we manage, how much money we make, what our title is, and many times we don’t often just stop and even simply ask ourselves the question, what truly matters to me? What do I really care about at work? 

I often ask my clients, a good way to really discover what really matters to you is to ask yourself, what really lights you up? What do you come to work and you are just giddy about? Like you’re just full-on geeking out. That is a really good clue to decide what matters to you when you can know that by reading and looking at your energy. How do I feel when I’m doing this thing or I’m thinking about this thing? 

You can also discover what really matters to you by discovering, you know, what makes you feel resentful. You know, lots of times when we feel resentment, it’s often because our values have been crossed, and we might feel resentful about the number of hours we’re working because maybe we value work-life balance. Maybe we feel a little bit resentful about the lack of our time with our family because family isn’t a value. Or lack of ability to be creative because the organization doesn’t value creativity. 

So when we really slow down and we start to think about our energy, what gives us energy, what takes away our energy, we can start to get clues as to what really matters to us, and then we become more informed when we go on job interviews, and we say, and I encourage and coach many of my clients to say, just to be clear, here are the things at work that really matter to me. Tell me, in your organization, what you do to support these things. And just be clear about what matters, and asking our future employers, tell me what you do to support this. 

Mac Prichard:

Terrific. We’re gonna take a quick break, Kelli. When we come back, I want to talk about the third area you encourage your clients to focus on, which is, aligning your values with your work, and then I want to walk through the five questions you use with the people you work with to get clarity about whether you should stay or go and make a career change. So stay with us. 

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Now, let’s get back to the show.

We’re back in the Mac’s List studio. I’m talking with Kelli Thompson.

She’s a leadership and career coach. Kelli’s mission is to help women advance to the rooms where decisions are made. 

She’s also the author of Closing The Confidence Gap: Boost Your Peace, Your Potential & Your Paycheck. 

Kelli joins us from Omaha, Nebraska.  

Now, Kelli, before the break, we were talking about several of the areas that you need to focus on when you’re considering making a career change, and you’ve got five questions that can help your clients and our listeners answer that question. 

But I want to talk about the third area, which is to find work that aligns your values with your work. And I’m just curious, why is this important to do, Kelli? 

Kelli Thompson: 

Well, I think if we do work that’s outside of our values, we’re always going to feel resentful. So, let me give, I think, a really relevant example a lot of my clients are struggling with, and maybe as you’re listening, you’re thinking about this, too. 

A lot of my clients are getting called back to the office, and some of them are thrilled. They’re so excited. They want to be in an office. Some of them, they’re in the middle. Some of them, they just are, gosh, I’ve got to get up. I’ve got to put on pants with a button. I have a commute. All of the things, and they just love the variety that has come from working from home. 

And a lot of women have taken on the brunt of labor in the pandemic of the remote learning, getting kids to be all the places, and research has shown from Mckenzie and Lean In that forty percent of women have considered quitting because they’re just overwhelmed. 

And so, when it comes to values, this is the first time where I think folks have really paused to say, gosh, do I even want this? What does my career mean to me? What do I really need to be happy?

And so, a lot of my clients are asking questions like, how much flexibility do I really need? And a lot of them, their value of flexibility, how much flexibility and freedom they value is really becoming apparent in these things, their values of work-life balance. Their values of family and health and all those sorts of things have come to the forefront because we’ve all gone through this collective experience together. And so, they are oftentimes, if they’re lucky, working for an organization that matches those values. 

Yep, I want hybrid. My organization offers hybrid. We’re good. A lot of my clients are saying, oh my goodness. My company is calling us back, and I’m feeling resentful because one of the things that I’ve really enjoyed in the pandemic was all of this flexibility. All of this freedom. My health is better. My work-life balance is better, and now we have a mismatch, and that mismatch is causing resentment, and so, now I’m gonna have to start to make some choices on whether to stay or whether to go. 

And so, that’s why we keep coming back to these questions of, what are your values? And do they match the values of the organization? And nothing has made this more apparent than the pandemic. Because that’s all had us stop and question, gosh, what do I really want? And does it match what’s my organization offers? 

Mac Prichard:

Well, let’s go through your list of five questions. Number one on your list is, does this organization align with my career values? Do I agree with the way it makes decisions? Kelli, how do you find out about an organization’s values? 

Kelli Thompson: 

A great way I always ask this of my clients, I tell my clients, when they go on interviews, I say, here are three questions you can ask. The first one is you can always tell what someone values or what an organization values, is by where they spend their money. So when I was looking to change organizations, I led training and development teams, and I previously worked for an organization that was unwilling to provide a good amount of budget towards training and development. There’s a value mismatch there. So in the interview, I would ask the employer, tell me what your training and development budget is. 

For my clients, I have a lot of women who tend to work in marketing. It’s a field that tends to find me. And I have them go in and ask, tell me what the marketing budget is. How much do you have set aside for these things? I think it’s really clear to say what they value is where their money is gonna go. 

I also have them ask about decisions. Tell me about how you make decisions as it relates to your employees. Tell me about your process for making decisions because, again, it’s not going to be the I agree with every decision that an organization makes. I want to understand how you make decisions. And so, I did. My clients do. They’ll go in and say tell me about a time that you had to make a decision that greatly impacted your employees, whether it be benefits, training, rewards, et cetera. And that’s gonna give you some clues as to what they value in terms of how they treat their employees. 

And then another great question just to ask yourself is asking the same people in the interview process the same question about, you know, tell me what frustrates employees around here. Tell me what issues the organization continues to have to work on over time, and you’ll start to, hopefully, notice some consistency in those answers. 

Which one, consistency, is good because then you know that everyone is aligned? But when you can start to ask yourself, like, okay. Every organization has problems that just recur, and those recurring problems can give you some clues as to what the organization values and what might be missing, and you just have to ask yourself. No organization is perfect. Am I okay with some of the imperfections that continue to happen in this organization? 

Mac Prichard:

Number two on your list of five questions to ask before making a career change is, does this organization provide me an opportunity to use my best talents somewhere else? How does the answer to this question help you make up your mind about a career change, Kelli? 

Kelli Thompson: 

Yes. So lots of times what happens is folks get really upset, you know. They’re drained. They’re exhausted. And I think, sometimes, the immediate urge is I have to look at another organization. 

But what I do with a lot of my clients, and I’m thinking of one in specific. She was in sales, and she was just exhausted. It was a global role. She was traveling all of the time. She felt like she was pushing a rock uphill. Really burnt out. 

But on the side of her desk, they had her doing diversity and inclusion work and corporate social responsibility work. She loved it. It was one of those little side projects, you know, that we get fascinated on, and we just want to go spend all of our time there. 

She was actually going into her boss to quit. And one of the things we talked about was, well, is there actually an opportunity to stay at this organization? Which she actually did love, and ask, could I make this side thing a full-time thing? 

And so, she did. She went into her current boss and said, you know, listed all the reasons why she really wasn’t a fit for her current role, but really brought in an idea of how she could make this side project a positive, impactful, and revenue-generating opportunity for the organization. 

And that’s a beautiful example to say, you know what? Sometimes when you’re saying, do I stay or go? You may not always have to leave your organization. I really encourage folks that if they do love where they work, to go and talk to your boss. And say, is there an opportunity for me to use this? This thing lights me up. Do this thing that makes me feel creative and in flow. Just ask. The worst case is they’re gonna say no, and unfortunately, that’s not here, and that actually brings you more clarity on if you need to stay or go. 

Mac Prichard:

Number three on your list of five questions to ask when considering a career change is, how have I advocated for the changes I want? What do you mean here, Kelli? 

Kelli Thompson: 

You know, I think a lot of the things that happen is we get frustrated, and decisions don’t go our way. Maybe we’ve been re-orged. Maybe we’re not happy with our current state of work-life balance. And so, lots of times when clients come to me, and they want to work with me, one of the first, like, I need to leave. I’ve got to go. I’m so burnt out. I’m so tired. I’m so sick of the organization, et cetera. 

I often ask them, so tell me, what happened when you went to your leader and you advocated for some of these work-life changes you want to see? And many times, there’s a long pause, and they say, well, I haven’t. And so, I think, sometimes, we just kind of sit and silently hope that, like, things will change without us actually having to advocate for them. 

And so, I have another client who, again, global role, different organization. She just was exhausted. She was exhausted with all the five pm dinner time meetings, and she was just ready to throw in the towel and quit. And I asked her, I said, well, have you talked to your boss about different options you can do with trading off times and setting more healthy boundaries? And she’s like, well, no. And so, she went, she sat down, and she talked to her boss, she talked to the people in Japan, and they were like, oh, we’d be happy to trade off night meetings with you. And through a simple conversation, she was able to advocate for the changes she wanted to see, and she’s a whole lot happier. 

So it’s always helpful to remember, before I jump ship, have I actually talked to somebody in my organization about what I want to see different? 

Mac Prichard:

Your fourth question that you encourage your clients to ask when considering a career change is, what boundaries do I need to set and communicate? How does setting boundaries help you make a career change, Kelli? 

Kelli Thompson: 

Setting boundaries is another really related stream to what we’ve been talking about. I see this a lot with high achievers. What do high achievers get? High achievers, they get all the projects. Why? Because they get stuff done. Everybody loves working with them. They execute, and what can start happening is they say yes to all of the things because they think I have to say yes. So that I look capable. I have to say yes to keep people happy. I have to say yes to look perfect and to do all these things.

And what happens is they get this burgeoning project load. They’re working nights. They’re working weekends. They’re exhausted. And lots of times, they put very unrealistic expectations on themselves and how quickly they can actually get these things done. And so, it’s really important that before we,  you know, get dissatisfied and jump ship and hope that another organization will make our circumstances different, we have to first say, well, what boundaries have I actually set around my work? 

I have a client who fixed this exact scenario, and she’s like, I’m working nights, I’m working weekends, and I’m over – she goes – I am, literally, Kelli, overpromising and under-delivering because I give these deadlines. And I’m like, why did I do this? I just said that date because I wanted to make them happy. And we had to get really clear about setting realistic timelines. Saying no to things. Saying, hey, thanks for thinking of me. I’m currently working on this project, so I can’t accommodate this request. Let’s talk about who else it can go to. 

Because one of the things that can happen is if we don’t start to fix all of the things that have caused us to live outside of our boundaries and overwork in our current role, we’re just going to take that same system into our new role and recreate all of those things. So let’s focus on setting healthy boundaries now, so we can carry it forward. 

Mac Prichard:

Your fifth and final question is, what is my to-do to create the future I want? What do you mean here, Kelli? 

Kelli Thompson: 

I think that this question is really a self-ownership question. You know, I’ve been through this in actually personal relationships. Just to be honest, I’m married and divorced. I was engaged, and I called off that wedding. I had gone through many different jobs. And, you know, it can be really easy to just blame other people and blame other circumstances, and say, my picker is broken, personally. Or just to say, I’m just not good at interviewing, and I’m not good at picking jobs. And we can just kind of blame our outside circumstances. 

But one of the things I realized was that, you know, there’s a common denominator in all of these failed relationships or these failed roles, and fortunately or unfortunately, that common denominator is me. And so, taking that ownership of saying something, I am doing conscious or unconscious choices, decisions that I’m making, behaviors that I’m choosing have caused these to fail. 

And so, I learned, I have to learn to ask myself, what do I need to do differently to create the future that I want? How can I account for the choices, like the breadcrumb trail that got me here? And if I want a different future, how do I need to choose differently? How do I need to choose different roles? How do I need to interview differently? Am I not aligning to my values and just saying yes to something for the title or the salary? 

And so, I believe this is so important, and one thing I work with my clients on, what do I need to own and choose differently so that I can create a different future that looks different from the past that’s made me unhappy. 

Mac Prichard:

Well, Kelli, it’s been a terrific conversation. Now tell us, what’s next for you? 

Kelli Thompson: 

Yeah, I’m working on my- I’m not working on it. Actually, my first book is done, and it comes out on November 1st. It’s called Closing The Confidence Gap: Boost Your Peace, Your Potential & Your Paycheck, and I’m really excited about talking about it and doing all of the fun book launch activities. And so, I’m having a lot of fun with my book launch. 

Mac Prichard:

Well, I know listeners can learn more about you and your book by visiting your website kelliraethompson.com, and you also invite listeners to connect with you on LinkedIn and Instagram, and if they do reach out to you on LinkedIn, I hope they’ll mention that they heard you on Find Your Dream Job. 

Now, Kelli, given all the useful tips you’ve shared today, what’s the one thing you want a listener to remember about today’s topic? Stay or go? Five questions to ask before you make a career change.  

Kelli Thompson: 

Number one advice is trust yourself. You know, this is revisiting a question that you asked me, and that is, a lot of people are going to give you advice in life. Very well-meaning, loving advice. And at the end of the day, we have to really go in and pause and ask ourselves, does this align with my values? Does this align with what I’m trying to create? Does this give me energy? Does it light me up? Does it align with my skills and my talents? 

Or does this feel like dread? Does this feel like an energy suck? And at the end of the day, I really think that we can be powerful, especially as women, when we can really learn to trust ourselves. Trust that still, small voice, our energy, because it will never lead you astray. It will always tell you your best decision of staying or going. 

Mac Prichard:

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Next week, our guest will be Rhodes Perry. 

He’s a bestselling author, podcast host, and award-winning social entrepreneur.

Rhodes is also the author of the new book, Imagine Belonging: Your Inclusive Leadership Guide to Building an Equitable Workplace.

Everybody wins when you feel accepted at work for your authentic self. You do a better job, you enjoy work more, and the workplace improves overall. 

Join us next Wednesday when Rhodes Perry and I talk about how to find an employer where you belong.

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

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This is Mac Prichard. See you next week.