549: Finding Your Ideal Career Fit by Conducting Career Experiments

Experimentation is the best way to reduce risk during a career change! By test driving conversations you can build relationships and quickly assess whether you want to dive further into a company, role, or industry.


on this episode

What’s the best way to figure out if a different role or industry is right for you? Many people believe you have to take huge risks to figure this out, but that’s not the case. Career experiments are the answer! They are the opposite of the tactical approaches you often hear about, and far more effective.

We are going to cover one of the most highly effective types of career experiments today: test driving conversations. This experiment will allow you to meet new people, quickly test new careers, and pave the way for creating your very own role custom-fit to you.

To demonstrate how this experiment works firsthand, we’ll walk through Laura Morrison’s initial career change (episode 213), and explain step-by-step how she test drove conversations that led to finding a role that was perfect for her!

Bonus: You can also hear a follow up of Laura’s career change in her “Where are they now” episode of the Happen To Your Career Podcast here!

Juggling her senior role with the challenges of being a new mother, Laura found herself at a crossroads. Despite loving the team she was working with, the work no longer fulfilled her, and the thought of returning each day became increasingly painful.

When Laura first found us at Happen to Your Career, she had already taken action to start looking outside of herself for a new job by going to a career coach. Coincidentally, on her walk home from that session she found our podcast, and “binge-listened for about a week!”

The thing that stuck was it was the first time I heard there were tools and processes to help me figure this out. I didn’t have to just look at job postings but I could do other types of work to think about what I wanted to do next.

Seven months later she found her dream career!

Woah–not so fast though. Laura went through a lot of self-reflection, and dug deep to understand what that next step should be. During this process, Laura also began to get feedback, and collect “mini-wins” from her coaches, her friends, and many others to help rebuilt her identity.

At the beginning of her coaching sessions, Laura wasn’t exactly sure what she wanted to do in her next role. But, as she began to complete her self-assessment projects, she couldn’t contain her excitement. Laura couldn’t stop talking about how much fun she had completing these self-assessments (her husband might have gotten a crash course or two!).  She kept this idea in the back of her mind, but still had a lot of searching to do.

Interestingly, Laura already knew what kind of culture she wanted in a company. She loved having the flexibility of wearing jeans and working from home when she wanted to. Even more importantly, she knew that the office should have a ping-pong table in it–for what it represented about the office culture.

But, from her experience in her last job Laura knew that a cultural-fit wasn’t enough. She had to find the right role, not just the right people.

That’s where she kept getting stuck. She felt naive about all the types of jobs that were out there.

One of the first things Laura did to understand all the job opportunities she could have was to begin test driving conversations!

She scheduled dozens of conversations with people in and out of her network–which was a growing experience in itself. Laura admits that this was one of the most challenging, but rewarding, parts of her coaching experience. She’s not necessarily a self-proclaimed extrovert. But hey, why not?

Laura met with tons of people who helped her understand what she did, and didn’t want in a role. Some of those conversations could have opened the door to a job. But, while it was tempting, Laura said no when she didn’t feel it was exactly right.

Until finally one day–she found it.

Laura learned quickly that she loves to prepare. For her conversations alone, she would do research and write prep questions for almost two hours each time!

But, when she finally found the perfect job opportunity, she realized that she just had to be herself.

With the help of her career coach, Laura practiced some mock interviews and found that her answers sounded good on paper, but “boring” during the actual interview. So, she stopped preparing as intensely as she might have and got herself in the zone.

It’s less important that you know how to answer a million behavior questions but get yourself in a headspace to be yourself and be confident in those conversations.”

Laura ended up securing her dream job. But, not only that–she has completely transformed her mindset from disengaged and hopeless to optimistic and confident. Laura is thriving in her career, as a new mom, and constantly achieving new goals!

What you’ll learn

  • How to explore new careers and industries through conversations 
  • Why an ideal career profile is a game changer for career change
  • How Laura strategically used career experiments to find her ideal career 
  • How to conduct a career experiment when you’re still working 

Success Stories

All the stars aligned and I ended up finding the right thing at the right place at the right time, and it was you guys! Everything that you said was speaking to me and the things that you had done in the job that you had transitioned out of and into. Also how finding work that you love is your passion for people! Honestly, it was you Scott, I mean, the way that you talked about it, how passionate you were, I was like, there's no way he's gonna put out a faulty product. So I'm gonna try it, you know… I recommend you to all my friends, you know, even if they don't realize that they're looking for a new job, I'm like this is the first step, let's do this! Even if you maybe don't move out of this career. This is going to help!

Maggie Romanovich, Director of Learning and Development, United States/Canada

I was nervous. But obviously, it worked out extremely well. (Kelly) was unbelievable. I still keep in touch with her. She's phenomenal. And we had such great conversations. I didn't know that I would be getting laid off from this job. And I signed up for Career Change Boot camp a week before I got laid off. Which was just insane timing. And I just started it. I remember I wrote you guys, and I was like, “I just got laid off from this job. I'm so happy that I enrolled in this program.” And it was, it just was the perfect time.

Melissa Shapiro, Career Specialist, United States/Canada

Scott Anthony Barlow 00:01

What's the best way to meet new people, quickly test new careers, and pave the way for creating your very own role, maybe custom fit to you even? Most people think that it must be some amazing tactic, but it's not.

Introduction 00:20

This is the Happen To Your Career podcast with Scott Anthony Barlow. We hope you stop doing work that doesn't fit you. Figure out what does and make it happen. We help you define the work that is unapologetically you, and then go get it. If you feel like you were meant for more, and you're ready to make a change, keep listening. Here's Scott. Here's Scott. Here's Scott.

Scott Anthony Barlow 00:45

On the Happen To Your Career podcast number 537, called Rethinking Informational Interviews: Stop Doing Them & Start Test Driving Conversations, there on that episode we broke down quite a bit of the step-by-step process of test driving conversations. And we talked about what are the differences but particularly the subtle differences between test-driving conversations, as well as informational interviews, and why those subtle differences actually make test-driving conversations far more effective. Here's what we didn't do in that episode, though. We didn't go through and give you an in-depth, real example with a real person or set of people. Today, we're going to show you exactly how test-driving conversations work with a real person. And that's where, if you go way back to Episode 299, Laura Morrison comes in.

Laura Morrison 01:43

I've always been fascinated with behavioral science. And I'd like to have many nights with friends having a couple of beers being like, "What's your Myers Briggs score?" I just like wanted to talk about that stuff. And I think it's because I think it's really interesting to understand what makes people do what they do.

Scott Anthony Barlow 02:01

That's Laura. And if you don't remember from her story way back in the early days, Episode 299, she was a senior level, she was working in a senior-level role in sustainability. And at that time, just had her first child. Even though she had no desire to stay at home with kids beyond her maternity leave, it was still really difficult to go back. Difficult because when she finally went back, she realized it was no longer challenging. It was actually pretty boring. And to make matters worse, she led a team of eight people who were actually really excited and really passionate about their work. Okay, normally, this is actually a good thing. But for her, it felt like she had to fake this excitement. And as you can imagine, since she was leaving a new kiddo at home every day, this wasn't something that she was into. And it became painful, rather quickly. So you can go back, you can listen to episode 299. We'll link this episode, in particular, in the show notes. There's quite a bit of her eight month journey that couldn't fit into the podcast. So it was years later, I sat down with Laura to break down step by step what had happened. How on earth did she get this opportunity with an organization that just absolutely fit her ideal career profile, which if you recall, that's usually the first step in the process after setting yourself up to have success, what we call a plan for inevitable success, and then defining a profile of your ideal career. And this was exactly the stage that Laura was at, where she had completed a version of her ideal career profile right before she started test-driving conversations. Here's a little bit about what she knew.

Laura Morrison 03:45

And I've always had a little bit of a natural instinct of like, this person's being a jerk, but it's probably just because of this XYZ insecurity, right? Like, I usually could read people's behavior a little deeper than just what you could see on the surface. So I didn't know what I wanted to do. But I knew the type of company I wanted to work for. So the first way I actually found and heard of the Predictive Index was I just started searching best places to work lists in Boston because at the time being local was very important. And I would read the name, and then I'd Google them and be like, "Okay, law firm, not interested." Right? Whatever. And T is pretty far down in the alphabet and some of these lists. So it took me a while to get there. But that's how I found The Predictive Index. Because of some of the resources you helped me with in terms of like finding people on LinkedIn, I was able to find a friend of mine, who I had met at what we called the worst moms group ever, and became friends because of it. It's a funny way to make a friend, like, we agree this was terrible.

Scott Anthony Barlow 04:53

So it turns out Laura's new friend from the worst mom's group ever ended up knowing somebody already that worked at The Predictive Index, this organization that she was really interested in at the time, and appeared to line up with her ideal career profile. Okay, so she asked that person to introduce her.

Laura Morrison 05:13

At the time, he was the head of marketing at The Predictive Index. He now has a fancier higher title that I can't remember. And so she introduced me, you know, more than willing to talk. We talked for like the 15 minutes.

Scott Anthony Barlow 05:27

Laura mentions 15 minutes because we often recommend asking for 15 minutes in order to make a test drive conversation happen. Now, the reason behind that is pretty simple, but also psychological. You want to ask for something that people can say 'yes' to, not something that is difficult to say yes to, most people can find 15 minutes. But when you're asking for an open-ended amount of time, or an hour, or even a half an hour or even 20 minutes, sometimes, it becomes more difficult to be able to say yes to that. But here's the interesting part. When you get there, and your 15 minutes passes, and you're like, "Hey, you know what, I want to be respectful of your time." Often, many people will say, "Yeah, I can find more time."

Laura Morrison 06:09

So I learned a little bit about him by looking on LinkedIn, I had a 15-minute call with him. And mentioned, I was curious about product marketing, and UX research, and product management because those were the things I was interested in at the time. One of the things that I did is I did not express that I was interested at working there for as long as humanly possible.

Scott Anthony Barlow 06:31

The reason why Laura mentions this here is because we often encourage people as they're going through experiments to keep an open mind because what you might find is that you don't actually really want to work at the organization or this particular type of role. And it was different for Laura, she validated that it actually was a good fit for her. But that's not always the case. So be aware. Okay, back to Laura's story.

Laura Morrison 06:57

First of all, I researched them so I could make a personal connection, like, "Oh, I hear you like music. Tell me about that." But then also, I have two or three awesome questions that I can never remember off the top of my head but are written in those documents.

Scott Anthony Barlow 07:10

One of Laura's favorite questions is, "What do you love about working in this role, or this company, or this section of the organization?" Her other questions were more personalized or individualized. Also, I want you to remember that this is a career experiment. So here's a fun way that Laura would look at the data visually afterward, and assess what actually worked, where are the areas where she wanted to keep going forward, and where didn't she.

Laura Morrison 07:41

But then I also like what highlights in green are some colors. If they said things that I was excited about, I was like, "Ooh, that sounds like something I'd like I put it in green." And if it wasn't, I was like, "Oh, that sounds terrible. I put it in red." And so like, I would talk to UX researchers and realize there was so much red, like that one green thing I was curious about probably wasn't enough. And it's not like I'm not detail-oriented, at least based on my behavioral pattern. I'm like, trained into it through engineering. So it's not like I ever printed them all and compared them. But it was like a good gauge for me. Okay, this is why I'm excited about product management. I've talked to four product managers and keep highlighting things in green.

Scott Anthony Barlow 08:21

So one of the things that you need to realize is that Laura was going through and even though she was really excited about this organization, The Predictive Index, she was also investigating other organizations and other roles and opportunities over a period of months. And during those conversations, during those interactions, she was having a lot of areas of red, but also a lot of areas of green for The Predictive Index and the conversation she was having there. And this was further reinforced as she continued to investigate and continue to interact with people in the organization.

Laura Morrison 08:56

One of the things before the interview, I don't like suits at all. I'm a pretty casual person. And I was like, I don't want to work at a place... And this was a while ago, this was four years ago, it's a little different now. I feel like no one wears a suit anymore, because everyone's in their pajamas. But so I'm like, okay, I'm going to wear something that I'm comfortable in like Lisa help with this too. And I'm gonna go in there and I'm going to be myself and not pretend to be anyone else and see what happens. And I think the morning or the night before, I was like, "Ryan", my husband, "there's a ping pong table in that office, and I'm going to see it and that's why I'm gonna want to work there." He's like, "How do you know that?" Because he's trying to get me to wear a suit, right? He's a banker. He's very formal. "Very sure you're comfortable wearing this to an interview?" I was like, "Yep, I'm comfortable. I guarantee there's a ping pong table in their office." And like, the first thing I do is I walk in and I see the ping pong table. That's good, right? I read the culture right. And then in our part of the interview, he whiteboard it for 30 minutes, didn't ask me a single question. And then another Engineer came in the room and started asking me all these questions about product management because he didn't like read the memo that I didn't know anything about software product niche. And he kept asking me all these questions. It's like, I don't know. I don't know the answer to that. What I do know is bla bla bla. And I just, I didn't try to be something other than I was, I just was honest and curious. And it was fun. Like, I left that interview energized, which is not something I would normally say about an interview.

Scott Anthony Barlow 10:27

Okay, so let's review for just a second here. Where Did Laura start out? Well, let's go back to step one. She started out in our Career Change Bootcamp program, which meant that step one was building a plan for when things get hard and identifying the people and things that she needed to make her career change successful. It's what we now call the plan for inevitable success. Step two was identifying a hypothesis where she spent several months creating a working draft of her ideal career profile. Step three was experimentation, where she specifically chose what we call test-driving conversations. That's what we're talking about right now, right? And during those conversations, she was reaching out to people in a variety of different ways, which we cover in different episodes. And we'll have links to some of those different ways and examples in the show notes. But finally, she observed that she was really excited about this one company, in particular, The Predictive Index, and had already been through many conversations. And the previously determined, prior to even uncovering The Predictive Index, that product management could be an area that she was excited about changing, too. So now, at this point, she had some validation that she was on to a role that could be right for her, as well as a company that could match up for her. That's when she started talking to the people at The Predictive Index And let's not gloss over the fact that she already now had relationships with them, after she had this series of those initial test drive conversations. And after that happened, after she had decided, "Yep, I want to work at The Predictive Index. How do I make that happen?" She went to them to discuss that she was interested and how it might be possible to work there because she was loving every interaction that she had. That's where they brought her into the interview process for a position that wasn't even posted at the time. And as you heard, those interviews that she had reinforced her experience with the company, and ultimately led to a pretty decent-sized race when she was worried initially about having to take a pay cut. And she ended up having to lead to this amazing opportunity. Now, when people listen to this, there's one thing that doesn't always seem obvious, doesn't always stand out. But it's really important for us to cover. It's that, to be able to get to this point where you actually have an opportunity in front of you, you actually have to give up initially, that you want it to lead to an opportunity at all. And you actually have to genuinely be curious when you are in the test-driving conversations. Test driving is for that purpose only. It's for test driving. It's for experimentation. It's for trying to find out if what you think you want is actually what you want. Nothing else.

Laura Morrison 13:27

I was trying not to be the person who was like, "Oh, my gosh, hire me." And I was trying not to sell myself essentially like I was trying to be curious and ask questions rather than me like you should hire me because of XYZ.

Scott Anthony Barlow 13:41

It's only at this point in time where you've gone through, and much as Laura did, you've already validated that this is an organization that I want to work with. This is a role that I want to actually be in. I have some actual evidence, if you will, through my experiments, that what I am heading towards is actually right for me. Only at that point in time, can you then shift your focus and ask for what you want. Well, you might be wondering, "How did Laura do that here?" Well, in addition to this conversation that you've been hearing that I had with Laura, years after the fact when we pieced together all the events that had happened, I also went back and looked at our notes. And what I discovered is that there was a point along the way where Laura had interacted with us saying, "You know what, I really want to work for this organization. I proved that this is something that's going to be right for me. How do I shift into let's get this mode now that I know what I want?" And what we did is we helped her understand that you could go have a conversation. It's pretty simple conversation saying, "You know what, I love all the interactions that I've had here. I have really enjoyed how you've taken me through and helped me understand what it is that you do. Every interaction I've had has really strengthened my desire to work here. And now at this point, I'm sure that I want to work here. So I'd love to talk to you about how we could make this happen. How in the future I could work with The Predictive Index." And so that's what we came up with. And if we fast forward quite a bit, that eventually led to do a progression, and ultimately, the interview process that you heard earlier on in the episode, and then ultimately an opportunity. Here's Laura talking about how it moved from I'm exploring into now we're talking about this role.

Laura Morrison 15:38

Before we're talking about careers, like jobs, how a product works, how marketing works. And then that second conversation, I think, we start talking about the role. What is the role specifically are you interested in it? Here's what I want in this role, that sort of conversation.

Scott Anthony Barlow 15:55

The last thing I should probably mention is that almost everyone, not everyone, but almost everyone we work with, when we have our clients have these types of conversations, they're uncomfortable, wildly uncomfortable at first. However, you build skill around it, and also comfort.

Laura Morrison 16:14

I mean, part of your whole process that I really appreciated was like forcing me to talk to all these people that I didn't know.

Scott Anthony Barlow 16:20

And you might ask, well, why do we do that? Why is that a part of our process in one way or another? And the simple answer is, because if you really want to get to work that fits you, work that is meaningful, work that actually is a wonderful situation for you, then it doesn't just come through the normal channels, you have to identify what it is, find where it can happen in the world, and then essentially, engineer your way into those opportunities. And we find that the very easiest way to do that is through people, whether it's these types of conversations, whether it is building new relationships, whether it is, you know, experimenting, and having other people's help in making your career change and understanding what you want, and getting that feedback all along the way, it always comes from people. People are the shortest road to being able to making this type of work possible. And guess what? It can be great for them just as much as it's great for you. So last thing I want to leave you with is that here's a couple of things that you can do today to get started. If you're not quite ready to experiment, if you haven't already identified where it is that you're heading, then that's where you need to start. And that's okay. Now you know what comes later on in the process. So the way that you can do that is by starting with your plan for inevitable success, and so that you are prepared to make a career change. And then if you've already done that, you can go into your ideal career profile and begin to identify your destination– where it is that you want to go, your hypothesis so that then you can go into experimentation. However, if you're all ready for experimentation, then the first thing that you can do is begin identifying those organizations, or roles that could be a great fit for you. And then reach out to folks so that you can begin scheduling some of these conversations, test drive conversations, like what we talked about. And we've got plenty of links here in the show notes to help you with each piece of the process referring back to other episodes. Or, if you want help with this, by all means, don't hesitate to reach out and send me a note directly Scott@happentoyourcareer.com. And just put 'Conversation' in the subject line. And we'll be more than happy to be able to help you for whatever stage you're at. Otherwise, pick out some organizations, and let's get started.

Scott Anthony Barlow 18:57

Hey, if you've been listening to our episodes here at Happen To Your Career and you want to make an intentional career change to much more meaningful work, and have it neatly laid out into an organized framework, well, guess what, we actually have that available for you in the Happen To Your Career book. It's available on Amazon, Audible anywhere else where you get your books. You'll learn about the five hidden obstacles, stopping your career change, how to figure out what would truly make you happy with your career. And what brings you more happy more often. And more importantly, how to transition to a much more fulfilling career and life. You can find the book on Amazon, Audible anywhere where books are sold, by the way, people are particularly loving the audio book, which you can access right now in second.

Scott Anthony Barlow 19:45

Here's a sneak peek into what we have coming up for you next week right here on Happen To Your Career.

Michal Balass 19:52

I got to that point, and I didn't want to give it up. But the thing of it is, is that I didn't want that.

Scott Anthony Barlow 20:01

Okay, if you've ever hung on to something for way, way longer than you should, this episode is for you. Whether it's a job or a relationship, maybe it's something completely different. But all of them can leave you feeling completely drained. So the question becomes, "How can you motivate yourself to make the necessary change and then make sure that you move on to the first sign of trouble the next time? How can you learn from it?"

Scott Anthony Barlow 20:30

All that and plenty more next week right here on Happen To Your Career. Make sure that you don't miss it. And if you haven't already, click Subscribe on your podcast player so that you can download this podcast in your sleep, and you get it automatically, even the bonus episodes every single week, sometimes multiple times a week. Until next week. Adios. I'm out.

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