How to Negotiate a Career Pivot with Lisa Lewis

How to Negotiate a Career Pivot with Lisa Lewis


If you are ambitious and analytical, and if you want to grow your career through strategic pivots, you won't want to miss this value-packed conversation with career change coach Lisa Lewis. 

Lisa Lewis is a career change coach helping ambitious, analytical individuals feeling stuck in their current jobs find different work that “fits” who they are. She does this by helping you clarify who you are, what you want most, what a great job for you looks like so you can make your career transition in the easiest way possible.

In this conversation, Lisa shares how she successfully negotiated a career pivot with a $10K increase in salary offer. (Listen carefully for the word-by-word script!) 

We also explore how the growth mindset can help ambitious people like you overcome the trap of perfectionism so you can embrace change, risk, growth, learning and joy. 

Learn more about Lisa here: 
Watch the Carol Dweck's TED talk

Full Episode Transcript

Hello! Welcome to Episode 37 of Born to Thrive with Jamie Lee. This is Jamie Lee and I am recording this intro at the Phoenix Airport.

I am here because my flight back to New York was delayed by three hours. Well, originally, I’m here because I presented a talk at the Human Capital Institute’s HR Call to Action conference here in Scottsdale, Arizona and you know what?

I think I did a B- job.

I pride myself on being a frequent public speaker and I learned that I have a lot more that I can offer. I have a lot more to learn. I have a lot more to grow in terms of my public speaking capacities. That’s my biggest takeaway from attending and presenting at this marvelous conference for HR professionals.

I’m telling you this because this podcast episode touched on something really big that is helping me work through my feelings of inadequacy, feelings of embarrassment, dare I say shame because I did a B- job at my public speaking engagement.

This is a really wonderful conversation I had with Lisa Lewis who is a wonderful career coach. She is in my coaching alliance. I have an alliance of coaches who...we all support each other and we help each other be held accountable so that we can continue to do the work of growing our business no matter how often we are told “no” or people don’t respond to us.

In any case, Lisa Lewis is great and she is a career change coach who helps ambitious, analytical individuals who are feeling stuck in their current jobs find different work that fits who they are. And she does this by helping people like you clarify who you are, what you want most, and what a great job for you looks like so that you can make your career transition in the easiest way possible.

And in this conversation, we talked about so many really amazing things. We talked about a wonderful way to negotiate your career pivot. She shared with us the Jenny Blake career Pivot Method, the four-step process. We talked about the trap of perfectionism. We talked about how to work through the fear of change. We talked about how courage is different from confidence. And we talked about the growth mindset, which is the mindset I am trying to apply to myself today as I work through my feelings of inadequacy because I didn’t do a perfect job.

So, if you are somebody who is ambitious, who wants to pivot, who wants to grow, who wants to risk change, risk uncertainty and thrive nonetheless, I think you will find this conversation super, super valuable.

And I want to give you a heads up that I am doing another webinar on October 17th. Come over to to sign up for that and also, if you are interested in being on my podcast, write me at and let’s take it from there.

Without further ado, here is the conversation with Lisa Lewis.

Lisa: How are you?

Jamie: I’m doing great, how are you?

Lisa: I am good, thank you. So honored and excited to get to show up on your podcast. Thank you!

Jamie: Same here, same here! So, I want to just share with you that...I’ve shared with my audience that you’ve been holding me accountable to grow my coaching business, so thank you for that, and I’m curious to know: What is a negotiation in your life or career that had the biggest impact on you?

Lisa: Well, I’m so excited to get to share parts of this story because it has some overlap with how I got into being a career coach myself. So, back when I was still working in the corporate space, I was doing digital marketing work, and I had been marching up the career ladder, and getting promotions and raises and additional responsibilities and it all felt exciting and very seductive. But more and more, the further I climbed up the career ladder, the less and less the work felt like it was aligned with my heart and my soul.

Jamie: Yeah.

Lisa: So, I had gotten myself into a great situation at an ed tech company where I was making really good money, I was eligible for a pretty strong bonus and by all accounts on the outside, I would have been in somebody’s dream job. It looked fabulous. But it just felt soulless for me.

And I spent a good, probably two or three years of my life trying to figure out how to find work that felt a little bit more like me, that I would feel alive and excited to do that work. And pretty quickly after I had moved into this job doing marketing work and managing multi-million dollar ad-spends for this tech company, I had started my own career coaching business on the side. It was my little test-drive side hustle to see if the type of thing that I had realized that I really loved doing was something that people would actually pay me to do.

Jamie: Hmm.

Lisa: And, slowly but surely, I started to get one client and then two clients and then three clients on the side while I was still doing my 9-5 job in the marketing space. But what I was realizing was that I was becoming more and more unhappy in my 9-5 and that dissatisfaction and unhappiness was bleeding into the rest of my life, as it is often wont to do.

Jamie: Mm-hmm.

Lisa: So, I was trying to figure out a way to make an internal pivot and get into something else at my organization. And I tried the route of making a pivot into HR, because I thought, you know, marketing into HR isn’t too, too big of a leap and HR feels kind of like it’s aligned with career coaching. You know, it’s very focused on employees and their happiness and creating sustainable career paths but that didn’t work.

And I tried to make a pivot into corporate communications because I thought, okay, corporate is a little bit more removed from the day-to-day work that I’m doing for our clients and our partners, so maybe that would feel good.

And then I realized that we had a career services offering that we did as part of the education branch of our work as a company. And so I talked to the folks on the career services team and they prefaced the conversation with “You know, we’re not hiring right now, but happy to have an informational conversation with you.” And I said, “Great! That works for me!” You know, anything to start to plant some seeds to make a transition felt like it was directionally correct and helpful for me.

Jamie: Mm-hmm.

Lisa: So, I sat down with the head of the department, head of the team, and had this great 45-minute conversation with her and by the end of the conversation, she said, “You know, I know I said that we weren’t hiring but let me see what I can do.”

Jamie: Mmmmm.

Lisa: And within a week she came back to me and said, “Hey, we have an offer for you if you want to make a transition but the offer is for a pretty significant amount less money to come over and make the transition because your responsibilities and the place that you would fit into our org chart is different from where you are on the marketing side of the house.”

So, I stepped up to the negotiation plate and said, “Hey, I am so grateful and so honored that you would think of me and that you would make this possible and I’d love to see if there’s a way that we can make this work for both of us. You know, I would love to be a part of your team but I also want to make sure that it feels like this is whole and this is fair and feels good for both of us.” So, I countered and said, “Hey, you know, I would love to see what else you can do to close the gap on salary and bonus in this new role.”

Jamie: How did you frame that? How did you create the basis for that ask?

Lisa: Well, I said, “I appreciate…” and this is all sort of me trying to recreate the memory, so forgive me if it’s not 100% accurate to how the conversation perfectly played out, but I remember saying something to the effect of “You know, I really appreciate everything that you’ve done for me here. I know that this is a difference in terms of the level of responsibility and the level of management that I would be moving into, but I also know that I have a lot to contribute, I’m really capable, and that there are going to be possibilities for me to really make a difference in this role. And if I come into this role and accept the pay as it is, it’s likely not going to be a sustainable good fit for me in the long term, so I’d love to see if we can find something in the middle that allows for me to feel whole. I’m happy to take a part of paycheck, a pay decrease, a pay cut to make this work but we’ve gotta find a way to get a little bit closer to the middle.”

Jamie: That’s fabulous!

Lisa: Thank you! So, HR and the department head put their heads together and they talked about it and they came back to me with an offer that was $10,000 higher than what they had initially offered me, which was great, but it was still a pay cut.

So, at that point, I said, “Hey, I feel like, I’m so appreciative of everything you’ve done to champion and find a way to make this a win-win. I think we’re almost there. Would you be open to talking about, once I get into the swing of things for this job, being a little bit more flexible on the hours? You know, potentially, instead of doing five 8-hour days, talking about doing four 10s instead. Making sure that I’m still meeting all of the obligations, I’m still serving all the students and clients that we have here and taking really good care of everything that needs to be done but in a way that feels like, again, it’s making me whole in all of this and it feels really fair and like something I’m excited to say yes to.”

Jamie: Excellent, yeah. I love how you brought in the non-monetary component of your work arrangement and it increased the overall value of this opportunity for you.

Lisa: Absolutely, but Jamie, here’s where the story gets interesting is that they agreed verbally that they would definitely be willing to talk about that and see how quickly we could put that into place and they even said things to effect of, “You know, we’d want you in the office five days a week for the first couple of months for training, but then that seems really reasonable and really doable once you are, you’re in good shape and you’ve been trained and you have relationships with all of our clients started.” And so I made the transition into the role and was feeling pretty good about it, but then that two months of time turned into three, turned into six, turned into nine.

Jamie: Mmmm.

Lisa: And I had some pretty frank conversations with my direct supervisor where it became abundantly clear that while he had said that that was something that he was open to, it wasn’t actually something that he had any intention of creating the space to accommodate for. So, it’s an interesting negotiation conversation in that I both was able to really close the gap and make some meaningful differences and compensations in the negotiation package, but that there are always times when sometimes your employer will say certain things or make things feel a way that might make them seem more concrete or more certain or more appealing than they may be when you get in the door and that negotiation is not a one time, you know, you do it and then you wash your hands of it, you’re done kind of thing. But it’s really an ongoing state of mind and an ongoing conversation that you’re having with your employer at all times to take care of yourself.

Jamie: Right. Yeah, what I’m hearing is that negotiation doesn’t end once you sign that agreement. It continues. It’s a series of agreements and you have to continue to ensure that the agreement is implemented and that everyone has the same understanding of what has been agreed to. Like you said, it’s an ongoing process. Thank you so much, this is a really rich lesson, a great success and also really great takeaways. So, you are a Pivot-certified coach and I’m curious to know what that means and would you walk us through what the Pivot Method is?

Lisa: Absolutely. I love talking about it. So the Pivot Method comes from a book written by Jenny Blake who is a fabulous coach and speaker and author. And the idea of a pivot is something that she borrowed from Silicon Valley, you know, because you’ve heard the parlance of if a startup has gotten their seed funding, they’ve entered the market and then they’re realizing that either their business model, the market-product fit, the profitability, something out of the way that they are trying to monetize isn’t quite optimal, isn’t quite getting them to the profit level that they need, then they oftentimes talk about a pivot. Which is their way of taking stock of what they’ve done so far, reorganizing their assets and their capabilities in a way that will likely be more profitable.

And while, in the world of Silicon Valley, that’s really seen as a product of failure and a negative thing to have to make a pivot, Jenny wanted to reclaim that phrasing and that ideology in a way that’s really empowering and really exciting for individuals. As a way to essentially take what’s working about who you are and what you’re doing and parlay that into mapping out what could be next for you.

So, the framework that she thinks about and that I coach and teach in my work has four different elements to it. Number one, it has what she calls the plant stage, and that is where you are trying to figure out what could be next and you start by taking stock of exactly where you are, who you are, and what’s working for you right now because if you don’t ground yourself in what’s already working and what you know to be true, it’s going to be really, really challenging to map out what could be next in a way that doesn’t accidentally having you, say, throwing out the baby with the bathwater or feeling like you’re starting from scratch and starting completely over. So, you start out in the plant stage to get your grounding, get your sea legs, and get a sense for where you could potentially go.

Then, once you’ve planted, the second part of the Pivot Method is to scan and take a look at the marketplace, your environment, your surroundings, to see what else is out there and evaluate the possibilities. Jenny often describes it as thinking about a basketball player, you know, you’re dribbling down the court and then when you’re about to make a pass, you stop and get your plant foot that keeps you grounded in one place, but then visually, you’re scanning down the court to see who’s open, who’s moving, what the different defensive and offensive possibilities look like.

So, it’s really doing the same thing with your own career. So, thinking about what trends are coming up in the marketplace that you could take advantage of and that excite you. Who are the people that you’re seeing out there as movers and shakers in the sort of role you want to move into, are in the industry that you’re curious about that you could draft off of or you could use maybe some of that professional envy in a really positive, productive way to sort of reverse engineer their path and their success to figure out what pieces from that you might be able to use?

Jamie: So, plant and then pivot…

Lisa: Well, plant and then scan.

Jamie: Oh, okay, I’m sorry.

Lisa: I know! There’s a lot of terminology! So, you start with your plant. Then you do the scan. Then you figure out what your pilot is going to be.

Jamie: Oh!

Lisa: So, your pilot is a pretty common piece of language for a way to do a test drive. What is your pilot program? What’s your beta test? How do you dip your pinky toe into the water of what might be next so that rather than going straight from the idea to jumping right into your pivot, you’re doing some risk management work to make sure that whatever feels good for you next doesn’t just feel good in the dream but it also feels good for you in the reality.

Jamie: Mmmm-hmmm.

Lisa: And then, once you run that pilot program and see how it feels and see what data you’re bringing back from that about what you want to do next, then if you are piloting in a direction that feels great, then you go ahead and you can make your official pivot where you commit, you go full-throttle towards the goal and you put together your strategy for how to do market entry into whatever the new role is, the new project is, the new organization is, to make that happen for yourself as efficiently and effectively and safely as it can.

Jamie: Hmm. That’s interesting. So, you...I find it really interesting that you use the word safe because it is a risk that you’re taking, no?

Lisa: Oh, absolutely! I think that’s a really important point that you’re bringing up because I don’t mean safe to mean comfortable and complacent and known. I mean safe in the way of you’re putting yourself out there and you’re taking risks and you are trying something that requires a lot of courage but doing it in the way that’s the smartest and most managed so that you will keep moving forward and sort of feeling the fear and feeling that uncertainty and yet taking action anyways, as opposed to getting to the point where you are excited about some future possibility, but it feels so far away and so different and so overwhelming that you end up totally stuck in analysis paralysis or in one of those perfectionistic, you know, brain holes that doesn’t allow for you to actually explore what it is that you’re curious about.

Jamie: Yeah, that’s excellent, because you specialize in working with ambitious and analytical people and as an ambitious and rather analytical person myself, I know that in my experience, when I do risk assessment, there is always that underlying fear of failing and you mentioned courage as a component of this and people often seek out coaches like you and like myself because they want to feel confident in the process of changing their jobs, in the process of negotiating a new offer. So, I wonder if there’s a distinction here that you can help draw for us. What is the difference in being courageous as opposed to simply confident?

Lisa: Absolutely. I’d love to go into that. And I want to come at it from a bit of an angle around perfectionism and I know, I remember back in Episode 3 of your podcast, you talk all about perfectionism and the Itty Bitty Shouldy Committee, which is so great and so memorable.

Jamie: Yeah.

Lisa: But what I often see is that people who tend to identify with a little streak of perfectionism, shall we say, get themselves into a certain way of thinking that is very black and white, right and wrong.

Jamie: Yep.

Lisa: And typically, this is not a thing you did to yourself on purpose. This is not a thing you did conscientiously. It often goes back to the way that you were socialized and you were affirmed growing up. So, Carol Dweck is a research psychologist who went to Barnard, just like I did, which is sort of a fun thing.

Jamie: I just picked up her book!

Lisa: Did you?

Jamie: It’s amazing!

Lisa: Oh, yeah.

Jamie: It’s an amazing book. I want to recommend Mindset by Carol S. Dweck to everyone who’s listening. It’s phenomenal. I’m sorry for the interruption, please continue.

Lisa: Well, if you’re gonna put some things in the notes from today’s conversation, you could also link to her TED Talk, which is also a fabulous resource and a good sort of appetizer teaser before you buy the book.

Jamie: Mmmm. I will watch it, thank you for that tip.

Lisa: Yeah, absolutely! So, Carol has these two different mindsets that she identified in children and students. One is a growth mindset, which is where you’re really focused on progress and action-taking and the process and the other is a fixed mindset, where you’re very focused on the outcome and really sort of the identity of who you are relative to that outcome. So, I think about this, you know, when you were a child and you think about the way that people would remark on what you were doing and who you were, would you get the sort of feedback about, “Wow, look at you reading! You are doing so much reading over there.”

Jamie: I got that. I got that.

Lisa: Yeah, well that type of feedback tended to be associated with growth mindsets. But the other type of feedback that people might have gotten was, “Look at you over there. You’re such a good reader. You must be so smart!” And it is ever so subtle in the difference in the way that that was posed to you. But if you’re getting the feedback of, “You’re a good reader,” somebody has just put a qualitative judgment on your activity and your action to make it good or bad.

Jamie: Mmm. Can I add something to that?

Lisa: Yes, please!

Jamie: I’m definitely a recovering perfectionist and I used to get straight As for most of the time and I remember feeling like such a failure when I got an A- or a B. And so I wonder if there was a lot of times in my very early childhood where I was praised for doing things well. Like, “Oh, that was good! You did it right! You got the right answer! That’s good. You didn’t get the right answer. That’s bad.”

Lisa: Yeah, oh, absolutely. And nobody does it maliciously and nobody does it intentionally but we all received that sort of feedback and especially high performers, you know, the type of people who seek you out as a coach and the type of people I meet, too, tend to have gotten a lot of feedback of,  “You must be very smart. You must be a great reader!”

That then not only puts a value judgment on the action, so the action can’t just exist in the beauty of the action itself, it has to have a label that it’s good or bad. But it also then becomes a part of your identity. When somebody says, “You know, you’re really smart,” then you internalize that you are smart and that any information that may challenge that or expand that or change that definition of who you are becomes a psychological threat.

Jamie: If you try things, that might make you look dumb.

Lisa: Right. One hundred percent. This is where the intersection point between perfectionism and courage comes in. Because if you have a fixed mindset about work, writ large in your life, whatever it is, you tend to be very fearful about the identity pieces. You know, I’ve always identified as a digital marketer, I’ve always identified as a technical project manager, I’ve always identified as whatever. And the possibility of expanding yourself to grow in a different direction feels like a threat to that identity because if you try it and you’re not immediately successful, then all of a sudden, it comes into conflict with who you had thought that you were.

Jamie: Yeah.

Lisa: And so confidence tends to come from that validation and that certainty of knowing what you’re doing and knowing that whatever you’re going to do is going to turn out well. So, perfectionistic people tend to be pretty confident when they’re in their own swim lane, but they tend to have a very difficult time summoning up the courage to try something new at which they might fail or they might be rejected. And I reject the word fail, writ large, because I really don’t think that that is something that exists but to try something that you don’t get the results you were hoping for from.

Jamie: Well, I also have experienced people define failure as when things don’t go as expected or as planned. And I mean, things almost always go as unexpected. We have plans and then other things happen all the time, right? So what do you call that?

Lisa: I think that’s exactly right. I think that life intervenes in all kinds of different ways that we could not have foreseen or foretold but that rather than looking for outcomes as you expect, like  for certain things to happen, I think it can be really helpful to focus on how you want something to feel.

Jamie: Mmm.

Lisa: And I think that this ties into another concept that I know, Jamie, you and I were talking about before we had gotten on the recording today about the idea of a beginner’s mindset. Because when you’re trying out something new and trying out an experiment and you’re not totally sure how things are going to end up, if you’re not used to that feeling of being a beginner and being experimental and creative and being okay with things not turning out as you had hoped, it can feel really, really painful to try something new.

Jamie: Yeah.

Lisa: But if you make that ever so slight, ever so nuanced, and ever so powerful mindset shift to say, “Well, I’m gonna try this as a beginner and see if I enjoy it, see what happens,” and you let yourself be really present in the experience and play with the craft and the process of whatever it is that you’re trying to do, there is so much potential for enjoyment and joy.

Jamie: And learning.

Lisa: And learning! And the beautiful, lovely, almost addictive rush of learning something new and feeling like you have this new knowledge, this new insight, this new wisdom about how things work in the world.

Jamie: Yeah, absolutely. Some of my most successful clients, they take that approach that every opportunity, every conversation, every interview is an opportunity to learn, right? As opposed to an opportunity to prove themselves as smart and successful, they go into that conversation with an attitude of curiosity and that can really transform not just the nature and the result, but the outcome of that conversation. And I think you’re touching on something really big, which is that we have the power to choose how we feel about anything.

Lisa: Yeah, absolutely. And I’d love to actually let you speak on that a little bit because I remember that one of the things that I noticed about you and your coaching which is such a gift that you’re giving to the universe is that you’re really able to help people peel apart the difference between an outcome and the story that they tell themselves, that they make that outcome mean about who they are, what they’re capable of, what is out there in the market for them.

Jamie: Right. And this is something that you, me, and Carol S. Dweck will all agree upon, which is that what we believe, what we think and believe about any given circumstance will have the impact on how we feel, on how we react or respond, and the result that we get. So, as you were saying, if we believe that we must be seen as smart to be successful, then you fall into the fixed mindset trap. But if you believe that you’re here to learn and that you can learn by trying and even if things don’t go as planned, even if the outcomes are not what you hoped for, there’s always room for more learning, because, as you said, you approach it with a beginner’s mind, then everything can be a joy. Even when you don’t get the job, you’re like, oh, that was a great opportunity for me to learn what not to do at a job interview. That was a really great opportunity for me to realize that, you know, I have more value to offer, etc.

Lisa: Oh, absolutely, and one of my favorite quotes from Marie Forleo is that “Everything is figure-out-able.” And if you walk into any situation, any interview, any possibility, any new skill-building opportunity with that mantra, that will inevitably lead you down the growth path because you will constantly trust in yourself and your own ability to figure things out, to use Google, to use your resources and not to put the pressure on yourself that you have to have all the answers and you have to be smart and you have to be perfect and you have to be right, but to allow for much more space for playfulness and creativity and learning and growth and for many different outcomes to come as the fruits of your labors.

Jamie: Absolutely. I couldn’t agree more. So, I so appreciate your wisdom, your insight, you expertise, and you’re a very eloquent speaker, Lisa. I so enjoyed having you on the podcast. I think many of our listeners would also enjoy learning more about you and your services, so where can people go to learn more about you and what you do?

Lisa: Well, I appreciate getting to speak to your amazing audience. I mean the sort of person who’s going to be listening to you is probably already really hungry for growth and improvement and advancement and opportunity and it’s a joy to get to be a part of that conversation. But if you’re listening to this and you’re interested in learning more, you can find me at my website which is

Jamie: Wonderful. Do you have any upcoming events that you want to share with the audience or workshops or…

Lisa: I don’t have anything that is scheduled at this very moment to share, but I do have a brand new, what I’m sort of calling my white-hot paper on the four career fulfillment pillars that I see over and over again can lead to the difference between feeling like you made a move into a role that fits who you are versus making a move into an opportunity which looks shiny and seductive on the outside but actually isn’t in alignment with your values.

Jamie: Ooooh!

Lisa: It’s at the very bottom of my website and I’m just starting to share that gospel around and I feel so strongly about it that I would be honored to get to have any of your listeners go and check it out and give it a read.

Jamie: It’s a white-hot paper. I love that!

Lisa: Thank you!

Jamie: Well, Lisa, it’s been a pleasure, as always. Thank you so much for being on the podcast and sharing your insights. I will talk to you soon.

Lisa: Sounds great! Thank you again.

Jamie: Alright, have a good one!

Lisa: You too. Bye bye!

Interview with Dr. Maya Borgueta: How Ambitious People Overcome Anxiety and Burnout

Interview with Dr. Maya Borgueta: How Ambitious People Overcome Anxiety and Burnout

How to Avoid the Trap of Impostor Syndrome

How to Avoid the Trap of Impostor Syndrome