How to Organize a Complex Work History on Your Resume

This week, Jeff and I are tackling the "messy" resume. If you’ve ever looked at your work history and felt like it was too complicated to explain, you aren’t alone. There are so many variables (gaps for family or school, received a quick promotion, or navigated a company merger) that it’s easy to feel like your background is a puzzle that won't fit together. We’re here to show you that there is a neat, professional way to frame every single one of those "complex" situations so you can tell your story with confidence.

This week, Jeff and I talk about:

• How to decide when to combine or separate job titles
• Strategic ways to list company mergers and acquisitions
• The simple "gap filler" trick for education or family leave
• How to highlight interim leadership and temporary roles
• Structuring project-based work and consulting blocks
• Downplaying irrelevant recent roles to pivot back to a former industry
• Why a long tenure at one company isn't the problem you think it is

Listen in to help us, help you give yourself the best chance of landing your Next Job… NOW :)

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Transcript

SPEAKER_01 0:00

Kind of doing that role for the last four years, but they only just promoted me now. Or if you were in one of the jobs for 80, 90% of the time you were with that company, like it's not uncommon for someone to start in like a frontline individual contributor role. Three months in they get promoted to manager, and then they were in that manager job for five years. We're not gonna list that first three months as its own separate job. It's just gonna be a bullet point that we were initially hired as this and we earned a promotion to manager uh after three months. Like that looks good and it's simple.

SPEAKER_00 0:41

Welcome to Next Job Now, the podcast where we help you get your next job right now.

SPEAKER_01 0:55

Welcome to the podcast. I'm Greg Langstaff. I'm a certified resume strategist. I've written over 2,000 resumes, and I love helping people get new jobs.

SPEAKER_00 1:05

And I'm Jeff, and I have a lot of questions about job searching. Together, we're gonna talk about everything you need to know about landing your next role. In this week's episode, we are talking about complex work history. We're gonna talk about what that means, how we can transform or present that on our resume if we have a bit of a nonlinear, overlapping or confusing history, uh, so that you can present that in a neat and organized way. What does it mean when someone says to you, Greg, I got complex work history?

SPEAKER_01 1:42

Well, usually people don't necessarily like lump themselves into that category, but when we're talking about complex work histories, we're talking about people who have gaps in their experience. We're talking about people who've received like multiple promotions. We're talking about people who maybe were demoted. We're talking about people who uh were at a company and then it was acquired by another company, and so they kept the same job at a different company. Like there's all kinds of elaborate situations. Could be someone who owned their own business, but while they were doing that, they might have had a job. Or they were consulting here and then the company hired them full-time. There's so many complex job history stories.

SPEAKER_00 2:28

I feel like 90% of us will have a complex work history. Like it seems so rare to have such a linear career. It seems uncommon to have no side gigs, no contracts. It seems common to have gaps. So is that what we mean by like presenting, like complex to present on our resume because like we're determining what needs to go on there or if we've had a promotion, but nothing's really changed about our responsibilities? Is that two jobs versus one job? Walk me through your thought process on how you approach complex work history. So let me give you a deeper example. Like when you're looking at a client's work, how do you decide whether or not a job should be combined or if they should be separated out? How do you determine how to list a certain gap? Are you looking at it per job or resume holistically?

SPEAKER_01 3:27

Well, like the ultimate goal is to tell your career story. They need to know what you've done and in what order you've done it in. And we do have a bit of an onus on us to simplify for the reader so they can easily understand our journey. Okay. So if you've had, say, a job at a company and then at a certain point you received a promotion. We have a couple of choices. We can list those as two separate jobs, one above the other, or we can combine them into one. We can use our little overview or a bullet point to describe that we got that promotion. Like I very often will say, initially hired as customer service representative and earned promotion into customer service manager role, taking on responsibility for blank, blank, and blank. And then like that allows us to just put those two jobs in one. But we've been transparent that we weren't always the customer service manager. We were promoted into the customer service manager role at a certain point, but the the job history is close enough that we're just gonna list the bullet points all in one place.

SPEAKER_00 4:40

I mean, I think you're bringing up a good point. Like it obviously complex work history is gonna be very case by case.

SPEAKER_01 4:46

Yeah.

SPEAKER_00 4:46

We all have these very unique. Do you have like four questions that you can kind of ask yourself when you're looking at a job to be like, how do I present this?

SPEAKER_01 4:57

I've okay. So we talked about combining jobs. Yeah. And yeah, the questions for that are like, were the responsibilities largely overlapping? Can I explain this by uh by with a bullet point or in the job overview explaining that this was a couple different job titles? Would it look good for someone to see very quickly that I was promoted? Because sometimes not combining is a great idea.

SPEAKER_00 5:24

Yeah.

SPEAKER_01 5:25

If they're looking and you can fit it in your resume to have multiple sections for this one company, it's nice to see, like, okay, first you were a director, then you were a VP. Like that kind of thing looks great. So we would want to separate those if it plays to our advantage.

SPEAKER_00 5:40

Yeah, I feel like if you're in a rule, say for 15 years and you've had the same responsibilities, but maybe you got a title change halfway. Yeah. Like that to me seems like a good opportunity where you can kind of separate and show two jobs on your resume to make it look more full.

SPEAKER_01 5:58

Yeah.

SPEAKER_00 5:59

And break up that 15 years into some chunks. So you're not just like one job, 30 bullet points.

SPEAKER_01 6:06

Yeah. And that's another thing is like there's no problem staying at a company for a long time. People think that they've done something terrible for their career when they stay at a company for a long time. You're good. But if you have the exact same job title for a long time, that's where employers start to get suspicious because they're thinking, did you not have any ambition to move up over the past 18 years? Were you not tapped for a promotion? Did your team not trust you to move up? That is where like it starts to look stagnant, and that's kind of dangerous for our career. So one company a long time, fine. One job at one company for a long time, not great.

SPEAKER_00 6:50

So I was wondering if we could try to kind of play a little game.

SPEAKER_01 6:54

Yeah.

SPEAKER_00 6:54

And see if we can work out whether it's complex or not that serious. Okay. All right. So let's, Greg, let's play a game. Okay. Easy to explain, hard to explain.

SPEAKER_01 7:07

Okay. That'll be easy to remember because you are easy to explain.

SPEAKER_00 7:12

And you have you are complex and deep.

SPEAKER_01 7:15

I don't think I'm that complex. I think I'm a very straightforward person.

SPEAKER_00 7:18

Straightforward? Yeah. Ah, but you're cool. You have layers. Okay. All right, let's do this. So uh for those listening at home, we're gonna play a little wavelength game where Greg is gonna try to explain based on uh the examples I give, how hard it is to explain some complex job histories. Okay. I have had the same job for many years, but I've had some natural promotions. There's been a couple overlaps in responsibilities, but I've been with one company, several promotions, some job title changes. I really just have to think about how I can frame the years that I've been there.

SPEAKER_01 8:01

I'm gonna leave that right in the middle. That's like kind of hard to explain, but not too tough. Interesting. You're just gonna leave it. Yeah, dead center.

SPEAKER_00 8:10

All right. You want to review with me? Yeah, you go. Boom! Right off. Here we go.

SPEAKER_01 8:19

Four points, which is the maximum amount of points.

SPEAKER_00 8:22

Uh that's nice.

SPEAKER_01 8:23

I think I hit it. You did bump it, yeah.

SPEAKER_00 8:25

It was there for four points. All right, let's do it again.

SPEAKER_01 8:27

Okay.

SPEAKER_00 8:30

My company merged, but my title stayed the same and my responsibilities stayed pretty similar.

SPEAKER_01 8:37

Oh, that's so easy to explain.

SPEAKER_00 8:40

Okay.

SPEAKER_01 8:41

Yeah. I'll explain how to explain it after I find out if I'm right.

SPEAKER_00 8:47

Ah I thought that was gonna be a little bit more challenging.

SPEAKER_01 8:51

It's so easy to say.

SPEAKER_00 8:52

Company merger.

SPEAKER_01 8:54

If your job stays the same when your companies merge, you have two choices. Again, you can separate it into two sections, or we can just list the job title as it has always been, list the employer, which is the new employer, and then in brackets say formally the name of the old employer. And then in the overview, you might want to say, like, initially recruited by first employer, and maintained position after acquisition by second employer, holding responsibility for, and then you run through your list, and then in your bullet points, you might want to share like a bit about your role in the integration after the acquisition.

SPEAKER_00 9:37

Oh, so like uh kind of a change management bullet point and like transitioning period to like how you supported what you did.

SPEAKER_01 9:45

Yeah, yeah. Because no matter what job you're in, no matter what level you're at, if you go through an acquisition and join a new company, you played an important part in making that happen. Yeah.

SPEAKER_00 9:57

All right, thanks. I feel like mergers sounds so complicated.

SPEAKER_01 10:00

I mean, it's complicated to buy and integrate a company, but on a resume, not that hard to explain.

SPEAKER_00 10:06

All right, here we go. On two occasions, I stepped into my manager's role during vacancies over several years, and I've now received that job full-time.

SPEAKER_01 10:23

Ooh, okay. Oh, that's a bit hard, but not too hard. Like I know exactly how I would do that. How would you do it? I'll tell you after I find out if I'm right.

SPEAKER_00 10:33

Yeah?

SPEAKER_01 10:33

It's kind of hard. But I I could pull it off.

SPEAKER_00 10:37

Alright, here we go. Oh, on the edge.

SPEAKER_01 10:42

Yeah, okay.

SPEAKER_00 10:44

So it's not that hard. Well, it's not as hard as I thought.

SPEAKER_01 10:46

Yeah, it's you pegged it as a near impossible. Um, here's what you do. In your your current, your current job, the manager title, just gonna treat it like a normal job.

SPEAKER_00 10:59

Okay.

SPEAKER_01 11:00

Um, in your previous job, the one where that you occasionally had to step up and step back down, in that job, we're gonna have a bullet point right at the top, interim leadership bullet point. And that's even the title I would give the bullet point, interim leadership. And then you would describe like on multiple occasions, uh elevated into a temporary management position, taking on accountability for you know, people, leadership, uh leadership team meetings, strategic planning, high-level uh oversight and strategy, like just you know, whatever it was that came onto your plate during those short-term periods. And then, like in the management role, that's where we would elaborate more on what we've accomplished in that time.

SPEAKER_00 11:49

I love watching you do that live.

SPEAKER_01 11:51

What?

SPEAKER_00 11:52

Like just kind of navigate the bullet points and like this is what I would do. I would do this bullet point, and I would separate here, here. It is amazing to watch your mind work. Can you tell I've written 2,000? We're almost at 2,500 resumes. I can absolutely see. I could tell. One more? Yeah, sure. Let's do one more. I like this. All right. I have two career gaps. One was for family, one was for education, uh, and I had a couple small part-time jobs in the middle while you were in gaps. Yeah.

SPEAKER_01 12:29

So we're talking gap, part-time job, part-time job, gap.

SPEAKER_00 12:36

Yeah.

SPEAKER_01 12:38

Yeah. That's that's harder. I mean, it's it's not hard to explain so much as it's hard for people to see that as having been okay.

SPEAKER_00 12:49

Because people are gonna get worried with the gaps and the part-time and gaps and the part-time. Yeah. But how would you explain it?

SPEAKER_01 12:57

Let me decide and then I'll tell you. Um that's pretty hard. That's one of the ones I struggle with the most.

SPEAKER_00 13:05

Interesting.

SPEAKER_01 13:06

Well, because I I guess my angle is like to to do it well. I know how to lay it out. That's actually really easy. I'm wondering if that's what you were thinking about when you chose it. It's super easy what you just described, but to make it look good is tough. Let's go with this. Let's say easy to explain.

SPEAKER_00 13:24

Oh two out of four points. Interesting. Yeah, we're on the edge here. Okay. So you're saying very complex and hard to overcome.

SPEAKER_01 13:37

Yeah.

SPEAKER_00 13:38

But it's not hard to list on your resume. That's what I'm saying. How would you list it on your resume?

SPEAKER_01 13:42

That's easy. Like, if you're ever if you have an explainable gap, which is like anything besides being just unemployed and having tr like trouble job searching for months on end, anything else you have an explanation. We just like use a gap filler. So education leave, family care leave, travel leave, relocation leave. Like, there's so many things if you move, if you or take time off for work, travel, whatever, or not for work, um, school, travel, whatever. Like those are easy. So you can pop in gap fillers like those. Only bad you only have to do that if it's like six months or more, otherwise, just leave it.

SPEAKER_02 14:23

Okay.

SPEAKER_01 14:23

The the thing about the part-time job that I was concerned with is like it's easy, right? Job title, company, location, dates, and then your bullet points and such. It's like having those part-time jobs, you don't have to mention that they're part-time. And let's say even if they were full-time. What's concerning is kind of the way you described it. I'm assuming that we're talking about jobs we weren't in for very long. Right. Two months, three months, whatever. And that just your reliability takes a massive hit when they see in the last five years, maybe you've had three of those years on and off of work and a couple of jobs where you were at for six months, eight months, whatever. Because they want someone who's like steady, reliable. We're gonna train you, it's gonna take six months for you to even be good at this. Then we want to get like three, four, five years out of you. And when you have that kind of a work history, you don't look like that type of person. All right.

SPEAKER_00 15:24

Well, thanks for playing.

SPEAKER_01 15:25

Great game, great game.

SPEAKER_00 15:27

So many more on my list here that I'm like curious about.

SPEAKER_01 15:30

Why don't we run through scenarios for people? Because like I bet a lot of people are listening to this waiting for their complex scenario to come up.

SPEAKER_00 15:37

Yeah, okay. Let me give you a couple more. So, like, I got a promotion, but in within three months I went back to my role because it was not for me.

SPEAKER_01 15:46

Uh, we do probably just all one role, and the promotion is a bullet point about a temporary elevation of responsibilities, where we can describe that as like a short stint. Definitely don't tell them we got re-demoted or that we decided to go back down.

SPEAKER_00 16:02

Interesting.

SPEAKER_01 16:03

Yeah.

SPEAKER_00 16:04

I worked for the same company. I've had five different titles, but it was the exact same job.

SPEAKER_01 16:11

I would combine them all. I'd pick one title that best represents the role. And then maybe in the overview, and if you hear me talking about the overview, that's like the little line before like one to two lines of text before the bullet points that explain a job. Um, in the overview, I might say, like, maybe initially hired us this first position and proceeded through multiple titles to eventually take on this role, which was responsible for this. And then, like, that way you've kind of covered your basis, saying there was a few different titles here.

SPEAKER_00 16:42

Uh, I worked, I started a consulting firm, but I would have small contracts like one year, six month, one year at major companies.

SPEAKER_01 16:52

Yeah, that's that's a really common one. So if you've got a consulting experience that isn't necessarily a full-time job, definitely lump it together as a consulting block on your resume. And then all these small company contracts that we've completed for a small or big company, like treat that as a bullet point or like a master bullet point with some indented sub-bullet points. If like you're at a company for say nine months and you accomplished a few nice things there, the overview of the that bullet point can be explaining why they hired you, and then your sub-bullet points, which are indented one and usually like the circle instead of the filled-in bullet point. Yeah. Um, those can be like some of the accomplishments within the purpose for which you were hired.

SPEAKER_00 17:41

So bullet points can have sub-bullet points. Like a your main bullet point can be the consulting at a company. Yeah. With a little like the bullet point becomes kind of like a mini overview. Like, is that how it works?

SPEAKER_01 17:53

Like it Yeah, absolutely. Like if you have a super complex project that you managed, you might need a few bullet points to describe it, but we want to know that it was all part of the same project. So that's a great instance to use the sub-bullet point structure.

SPEAKER_00 18:09

So project managers is like a complex one where you're working with, I'm a project manager for a company, all of my projects are vastly different. How do I explain that on my resume?

SPEAKER_01 18:22

What I might do in that situation is split that job into two subsections. So, like, we've got our job title and company at the top, got our little two-line overview explaining the purpose of the role, and then we have like in bold a little heading that says like core responsibilities. And then all the bullet points there are the things you did on every project. Like you were planning the project, you were bringing the stakeholders together, you were managing the budget. That gets the bullet points. Second subheading under that job is key projects, and each one of your projects gets a bullet point that explains what was the purpose of the project, what was the budget, how long were you working on it for, how many people were working on it, and did it achieve its ultimate goal?

SPEAKER_00 19:08

All right. Any other ones that stand out that you've seen kind of over the years that are like these are uh complex things.

SPEAKER_01 19:16

We've covered like promotions, demotions, temporary promotions, we've covered gaps, we've covered mergers and acquisitions.

SPEAKER_00 19:24

I left my full-time job to pursue like a different career, and that didn't work out, and I need to go back. So, like I left my job to become a coffee roaster. Yeah, my business isn't thriving, I need to go back into the corporate world.

SPEAKER_01 19:38

Okay, so going back.

SPEAKER_00 19:40

Going back.

SPEAKER_01 19:40

Yes, that's a great one. That happens so much. Yeah?

SPEAKER_00 19:44

Yeah.

SPEAKER_01 19:45

No, it's not always like a sad reason.

SPEAKER_00 19:47

Not a sad reason. Sometimes it's okay, okay. I just thought about like, oh no.

SPEAKER_01 19:51

It's usually like it's usually the other way around. Not that they left something they didn't like and now they're forced to go back. It's like they they were doing something they loved, they wanted to try something different, they didn't love it, they want to go back. It's so common. This is a conversation I have like twice a week with clients.

SPEAKER_00 20:10

Okay.

SPEAKER_01 20:11

What you do if your most recent job is not super relevant for the jobs you're applying to, is you just keep that section small. Like two, three, four bullet points at the most. And then that way, if your next job down is way more relevant, let that take up space, eight, ten bullet points, and they'll see it a lot sooner. They'll see it as bigger, more important to you. You talk more about it. That is how you go back into an industry that you used to be part of.

SPEAKER_00 20:42

It's now time for unusual interviews where we ask each other questions that we hope you never get asked. Greg, what is your favorite thing to do at the theme park?

SPEAKER_01 20:54

Oh man, I used to be such a roller coaster guy, but I can't handle it anymore. Like, it just makes me feel sick. Really? Yeah, I got I got hit with the motion sickness probably like 10 years ago.

SPEAKER_00 21:07

So you used to love it.

SPEAKER_01 21:09

Love it.

SPEAKER_00 21:09

Now you don't love it.

SPEAKER_01 21:11

Do you think you might love it again? No, I think we're gonna get in that upside-down loop-de-loop cycle.

SPEAKER_00 21:16

Oh, okay, okay.

SPEAKER_01 21:18

Alright, Jeff, my question for you. I asked you a few weeks ago how many words you know.

SPEAKER_00 21:23

Yeah.

SPEAKER_01 21:23

How many numbers do you know?

SPEAKER_00 21:26

I know a lot of numbers.

SPEAKER_01 21:28

Yeah.

SPEAKER_00 21:30

Infinity. No, that's not true. I don't know infinity. I think once you get up to the billions, I'm gonna get lost.

SPEAKER_01 21:37

No.

SPEAKER_00 21:38

Come on. I don't know what what happens after a billion. A trillion.

SPEAKER_01 21:41

Yeah.

SPEAKER_00 21:42

And then what?

SPEAKER_01 21:42

I d I don't know.

SPEAKER_00 21:44

That's it. Quadrillion? Don't ask me. But I don't know if I can five hundred and eighty seven billion? I don't know when you're gonna be able to do it.

SPEAKER_01 21:53

I'm not asking you to count.

SPEAKER_00 21:56

I would make it to seventy five, I think, before I stumble.

unknown 21:59

I

SPEAKER_00 22:00

Be I'd be distracted.

SPEAKER_01 22:02

That yeah. Yeah, that I mean, okay.

SPEAKER_00 22:05

Yeah.

SPEAKER_01 22:06

This is why we hope you never get asked it in a job interview.

SPEAKER_00 22:10

Because what's the point of that question? Thank you so much for listening to Next Job Now. If you've enjoyed this episode, please like, subscribe, leave us a rating, share it with someone who's looking for a job. Don't forget to grab free resources off of Greg's website, greglangstaff.com. And join us next week when we talk about tooting your own horn. Tooting your own horn. Boop boop.