Pivot with Your Strengths

Anita Brick: Hi, this is Anita Brick and welcome to CareerCast at Chicago Booth. To help you advance in your career. Today we're super delighted to have Kimberly Cummings here. She is a premier career and leadership development expert. Her mission is to empower women and people of color in the workplace. Through her company, Manifest Yourself, Kimberly provides in-person and virtual workshops, trainings, and coachings to professionals who want to have a dynamic career in life. Kimberly, don’t we all. And her first book–I'm sure will not be your last– is Next Move, Best Move: Transitioning into a Career You’ll Love. She has spoken to the Urban League, Princeton University, South by Southwest, and many others. And finally, for now, she is on the Board of Directors for the Power of [inaudible 00:00:58] organization.

So I love the fact that you are clearly dynamic, clearly ambitious, and you have a heart that also drives to add value both on the social impact and the profit side. Thank you for having that perspective and bringing that sensibility to our conversation today.

Kimberly B. Cummings: Thank you so much. I'm very excited to be here.

Anita Brick: Okay, good. Let's kick it off. An MBA student asked a question, and I think this is a question a lot of people have: “You had skills, knowledge, and experience that you brought to each of the roles. Because you've had for profit roles, non profit roles, entrepreneurial roles. And you always had that for a long time, that side entrepreneurial gig. But you had these skills and experiences. How would you advise an individual who wants to pivot into a new field without previous experience?”

Kimberly B. Cummings: So the biggest thing I always talk about is when you're in interviews, when you're speaking about your previous skills, experience, etc. it's your job to connect that to the job that you're applying to. I know we always talk about transferable skills, but continuously in interviews we see candidates just kind of speak from their exact perspective, but not related to that job no matter how many times we share that that's what you have to do. And I think when you're making a career pivot, that's really the piece that you have to draw upon. You have to understand how do you look at all of the skills that you've gained and almost draw the line into the role that you'd like to be in?

Like you shared, Anita, I've made several pivots across industries. Different things that from the outside may not make sense. But the key to doing that is really creating that synergy. I know this is audio, and I'm literally like pulling my fingers apart and putting them together and showing that line and making it crystal clear and making sure that you have those stories pre-prepared because people will push back. When I interview, I know I push back if I don't understand how it makes sense. Make sure that you can say clearly the experiences that you've had. How did those directly prepare you for that pivot role that you want to get into?

Anita Brick: If you are in Germany and you only speak English because there's an app for that, there's a way to translate. One of the things I see is that people get an idea, but the language gets all confused. So they use language that is very related to technology, tactical technology when they really want to be in strategy. How do you advise people to get an interpreter or to interpret on their own how to take those skills and yes, draw those connections, but do it in a language that is accessible for the audience. I find that that is a very tough thing for people to do.

Kimberly B. Cummings: 100%. So I think there's two ways that I've done it and I advise my clients. Number one, think about how doctors explain things to you. Think about your job as that like diagnosis and bring it down to the smallest way you can explain it, like how would you explain this at your child's first-grade career day? And use those basic principles of what you do and align that to the job that you like to have those core core skills.

Or on the other side, try and make connections in that field so you can have that candid conversation of, this is what I do. I have no idea how to connect this mess. Like, what would make you want to hire me in this area? What would I need to say? What language do I need to showcase to show that there's connectivity. And in  the book, I share this story when I move from being a banker to moving into higher education. And that's exactly what I did. I had my series 6, 63, Life and Health. I went from like mortgages and annuities and high-net worth clients and all those things, essentially a sales role and a high-net worth area in Long Island to being an admissions counselor. People are like, that doesn’t make sense at all? But it really does because admissions is just sales and education. I was selling a different product. I still had to build relationships. I still had to recommend products and services. There is so much synergy. I just had to take out all that financial language and connect the base of that role to the new role in admissions.

Anita Brick: Any conversation I have it all comes back to the relationships we build and those that we are able to sustain. And there are a couple of questions related to that. One was with an MBA student and she said: “In your book you talk about asking one’s connections to connect you to other people in their network. How do you do this without making it seem transactional? Because it feels that way to me.”

Kimberly B. Cummings: Number one is making sure that connection that you're speaking with is strong already. They understand who you are. They understand your intention. They know that you're not just looking to hop to this person, to that person, to that person. If that first relationship is strong, that person should be excited to expand and open their network up to you. That's literally my favorite question to ask. Is there anyone else in your network do you feel would be beneficial for me to connect with? And most mentors, sponsors, etc. are excited to open that door if the first relationship is solid. So my focus is always making sure that I've created a genuine connection first before I open up the doors and ask for additional follow-up connections.

Anita Brick: Totally agree. So here's a related question from an alum. And he said: “How do you network for the long term – build that relationship when you have a short term need?”

Kimberly B. Cummings: Oh, I love that. This is a hard one. You're asking someone to give you a loan, right? You're asking someone to to loan something for you and you haven't really sowed any seeds yet. It's like borrowing money. It's almost expediting that relationship process. But asking in a way that isn't directional. So when you have that initial conversation, just asking someone, you know, asking for that coffee chat, do you have 15 to 20 minutes to connect with me? I'd love to learn more about your experience. In most cases, that person may ask at the end like, you know, this conversation was great, let me know if you need anything else. I always ask in a way to invite them to assist versus asking them to do something. So I'll say something like, I know I just met you, you know, there happens to be a role open at your organization. Would you be able to tell me more or even refer me to someone in that area if you're comfortable? Give them the opportunity to think about do they want to make that? Because on the other side of the coin, I've been burnt many times referring people to things. So much so that generally the answer is going to be no, it's going to be no. Or I'm going to say that, you know, I'm happy to make the introduction. It's not going to be that super strong referral. Or I'll ask, well, I'd love to take your resume, I'll take it and I'll pass it on to that person. But again, that referral is not going to be that strong. It's going to be, hey, I spoke with this person one time and they seemed all right. But again, I just met them. You know, I'm not responsible. Please go for it and then as you see fit.

Versus if I had a stronger relationship, I'm like, oh my gosh, I've talked to this person for the past six months like they've been incredible. I know this that the third. I really think that you should bring them to the top of the pile. I will serve as a reference. So I think it's also just understanding there are different types of introductions and references. And if you haven't sowed that seed, it's not going to be as strong. Again, there's no shame in asking, just making sure that it's not a forceful ask.

Anita Brick: I like that. I usually give people a nod too. I like what you said and I'll say no pressure, but if you feel comfortable. Because I want them to be able to respond to me in the future. But if I backed them into a corner, they may say yes, do very little, and then not feel comfortable the next time. I like that a lot.

So to shift gears a little, we had some questions about challenges related to this. So this alum said: “I grew up in a family where playing smaller was expected of me. Now this has turned into a bad habit. What are a couple of things you would suggest that I could do to break that pattern?”

Kimberly B. Cummings: This is a hard one and believe it or not, I feel like people now and they know me like, oh my gosh, you're so confident. You’ve never played small. That is a lie. I am someone who never would talk about any accomplishments or anything in my life. It was just like, you know me, you know me, I hope you know that I do good work.

The thing that I always share, and what I had to learn, is that your accomplishments, your success, your achievements are fact. I think many times we play small, we look at sharing about ourselves, building those connections. We look at it as we're bragging. We look at it as you know, we're saying too much. We don't need to do this thing, it's a little overzealous. But when you are advocating for yourself, when you're having these conversations, sharing the facts about your experience, it's a fact. It's not bragging. You did it. You achieved it. And slowly but surely, flexing that muscle in environments that mean something to you. I think there is nothing worse than being in an environment where you have an opportunity and you don't say anything. You are kicking yourself when you get home the entire way because you knew you should have made that introduction and raised your hand, whatever it is. And a lot of times I think about, imagine if you not saying anything leaves you in the same place you were next year. Flex that muscle.

Anita Brick: You're absolutely right. I do think that the playing smaller can be cultural, and it can be related to a lot of different things. I like to think about it this way. If you don't give me the full of who you are and the value you bring, you're actually cheating me.

So let's shift to a couple of situations or actually three situations. The first one is: “I'm very fortunate to have a number of strengths, and I'm deeply grateful to have them. That said, I'm often valued for what I no longer want to do. How can someone shift others' perspective so I can stop doing things I really don't want to do anymore?”

Kimberly B. Cummings: Oh, I love that. I think I call this like the jack or jill of all trades. When you can do a lot of things, like you can come in and do whatever it is and you do it well, I think it's important to start highlighting the thing that you'd like to do. Finding ways to do more of what you like, and even being more comfortable, pushing back a little bit, that when someone asks you like, hey, can you work on this? Just reiterating, sure, like I may be able to do this, but I'd really love to work on this instead. This is a skill I want to work on, finding ways to realign your role into whatever area you'd like to versus kind of just taking everything on. I know that can be a little difficult sometimes. There's a lot of pushback that may happen, but doing your best to continue to move your career strategy, your objective, your roles into that area, you want to double down on.

What I've seen there's a lot of people, they just keep on taking all the things. Yeah, it really takes speaking up to make sure you get to do the thing.

Anita Brick: I agree it takes courage too, especially if you've made yourself really indispensable in one area. What is the incentive for the lead, the manager or your boss in that sense, to shift you because you're really fulfilling that person's goals and objectives? Have you ever seen someone be able to start to break that into a small piece, where they were able to continue to be indispensable as they are, and also take on something else?

Kimberly B. Cummings: Definitely. I think it really is important for them to formally get on something that aligns to what they like to do, whether it's a project, whether it's in a professional association, or even if it's time for them to apply to a role that could have doubled down on that new area. If you find that your manager is still holding on to the old you or the old jack or jill of all trades, you may have to formally make that switch and that can be hard.

But ultimately, we're talking about your overall career satisfaction. Subline in my book is transitioning into a career you’ll love. And you know, that's really what's going to bring you joy. A formal transition may be needed if you're not necessarily getting that support. You know, when you're the manager star player who can do everything they may say, oh yeah, yeah, yeah, yeah, well, we'll move to that. We'll move to that. We'll do that sooner. You know, next quarter we'll work on that. And if you see that happening too much, a formal transition may be needed.

Anita Brick: Yep, I agree. And I do think you mentioned professional associations to get some experience. Nonprofits, start ups, all of those count. It all counts, whether you're paid for it or not.

Kimberly B. Cummings: 100%.

Anita Brick: Okay. So here is an alum – I sensed a little sadness here. And he said: “I have 20 years in a particular industry where I built a career primarily to support my family. Now I feel it's too late to pursue my dream. Can you please share how you advise clients to relaunch after a couple of decades?”

Kimberly B. Cummings: I hear the sadness too. I think it's when you realize that you no longer want to do what you built a career on. It's almost like you need to be a fish out of water again. I think that's very difficult, especially it sounds like this person has the weight of their family on their back too.

I always recommend deeply thinking about your wine, your passion, your interests and then seeing how you can make this transition to make things happier for you. In the last conversation, you said all the things have weight–nonprofits, professional associations, side hustle, all of the things. If you are unable to make a leap right now for whatever reason, even if it's financial, because I do believe that's a real thing, find ways to bring that into your career now.

When I knew I wanted to make a switch, professional associations were one of the big ways where I got experience in areas that I didn't necessarily have in my day to day job, so that when I interviewed for the next thing, I already had a little stuff, like behind the scenes. It also brought me joy working on what I really, really love. Figuring out what skills you have that aligned to that new passion, that new interest, so you can make a seamless transition is really key.

And for someone who has a lot of experience, I often see that the level may be hard. So let's say you're a director over here, but moving to a new industry, you kind of have to start over because you don't have any experience. It's sometimes how can you get the experience behind the scene, especially if this is a financial thing that you can come in a little bit higher. So how are you able to supplement the salary making that move or upskill yourself so you can come in at a higher level and slowly transition yourself into your passion?

Anita Brick: Really good point. Maybe you could tell us a little bit about how you thought about and built your side gig, because it really did a couple of things. I mean, it did many things for you. How could someone use a side gig to also do what you just suggested?

Kimberly B. Cummings: Oh yes, I side-hustled from 2013 to 2021, so a long time. I just left my full-time job in May 2021, so I definitely did it for a long, long time. And I think it's figuring out what you like to do. So for me, earlier on, I was speaking at a lot of conferences. I was frequently getting asked to do more career leadership development coaching on the side.

So I launched my own practice. It was very small in the beginning, but over the years I got bigger and bigger and bigger to the point where I wasn't able to balance both. So what is the thing that you would be able to do on your own that aligns that passion project? What skills do you need to do that thing?

I knew nothing about owning a business like absolutely nothing. I ended up hiring coaches, business coaches, strategy coaches to help me build out the framework for what my business would look like, to help me grow out and build out group programs and one on one coaching programs. I invested a lot, and that alone made me so happy. It brought so much more joy to my 9 to 5, because I knew I had something to look forward to, 5 to 9 on the weekends.

Figure out what is the product or service you'd like to offer. That's really what having the side hustle is. It's developing a product or service. What are the problems you'd like to solve, and how can you build out the infrastructure to solve that problem? You have an idea and if you need help, figure out who you can reach out to, whether it's an entrepreneurship center in your city, whether it's your alma mater, whether it's getting a coach outside to help you build this out for yourself. And start to slowly but surely build that on the side.

I know the experience that I built helped me make the transition into a talent acquisition in 2019. I worked as a director of Global Diversity Talent Acquisition Strategy at a Fortune 500 company in financial services. And that job came more from my business than it did from my experience in career services, because of my involvement in professional associations and the company I built that serve women and people of color.

Anita Brick: I love it, that's great. You know, when you think about it, it sounds like you started small and you scaled based on time and other resources and that's good.

Kimberly B. Cummings: Yeah. I saw my clients really getting results. People who I work with getting results. Alright, I think I know what I’m doing, let's see what I can do. Let’s start setting some revenue goal. And that's when things got much more serious.

Anita Brick: That's great. Here's an alum who you'll hear from the question sounds stuck and maybe more than a little discouraged. He said: “For 14 years now, I've been taking on roles that are boring, unfulfilling, and where I have no opportunity for promotion, contribution, or meaning. And I do this to support my family. If you are typecast in a role, what's one thing you would suggest someone work on to effectuate a meaningful career transition now?” That's a tough one too.

Kimberly B. Cummings: I think it is. But I also think it's very common. I think they need a paycheck so they get a job that gives them a paycheck. The first thing I would say is people treat jobs sometimes like they treat romantic partners, they just break up and get someone else break up and get someone else, and they don't do any work. So they don't understand why they keep attracting the same partner. My question is, do you ever think any of these jobs are going to be happy or fulfilling? Or did you just take them because they were offered? And then I'd ask, are you financially stable in your current job? And if yes, then I'd say it's time to do the work and really head into a deep self-discovery of what are the skills they have? What experiences do they consider their strengths in the workplace, and then what are they interested in? It's time to re-navigate. And yes, it's tough. Yes, it takes time. But similar to that last person who we  answered their question, I think it's how can we slowly adjust and re-navigate to something that makes us happy?

Anita Brick: One other dimension here, the getting stuck and pigeonholed, is at a lower level than this person would want. Does that change any part of your answer? Is there anything you would add to that?

Kimberly B. Cummings: Many times when you're stuck at a lower level, it takes some positioning to get to that higher level. What is the reason? Are they lacking relationships or are they lacking experience? Are they lacking connections? What is the thing that has them keep getting these lower offers or lower roles? Once they figure out what that thing is, we have to speak to it.

Anita Brick: First and foremost, what is the thread that ties together those different opportunities that are not what the person wants and not even at the right level?

Kimberly B. Cummings: 100%. I teach all of my clients that there is a gap between every role you'd like to go to. There's where you are right now, standing in the sand. And then I don't know how far away from you–sometimes it could be a step, sometimes it could be a mile–is the role that you'd like to get into. And it's your job to figure out what is that gap in between and how can you solve for that gap or make it smaller?

For some folks, we can solve it with relationships with a certificate or a professional association to get some skills. For other things, it's like, no, that gap really isn't that big. We just need to apply and position yourself appropriately. The gap is different for everyone, but it's really important that you acknowledge that, because that's what the hiring leader is going to drill in on in your interview. they need to understand how that gap is closed so that they know that you're ready for that next move.

Anita Brick: Yeah. And sometimes that takes a lot of hard, critical self-reflection.

Kimberly B. Cummings: Yes.

Anita Brick: The outcome is good. Sometimes the middle part's not so much fun, but you get where you want to go. You have to kind of do that work.

Kimberly B. Cummings: You got to go through the fire a little bit.

Anita Brick: Absolutely. So we talked about a number of things. One thing that I found very interesting, and I was glad to see a question around it. You talk about brand and compensation. So the question from an alumni is: “What are a few key elements of brand that you have seen increase a person's overall compensation?”

Kimberly B. Cummings: I really believe it's about your unique value to that organization, and that starts from the moment you interact with them. That's the thing that I always share about salary negotiation and compensation. People are waiting to get a bad offer. They're just expecting they're going to get a lowball offer, and they're gonna have to fight tooth and nail to get where they rightfully belong.

But when you start the expectation in that first interaction, a sourcer giving you a phone call, talking about how you may be in the pipeline for a role that's not even open yet, or whether it's the hiring leader talking to you. You have to set the expectation and make it clear what your unique value proposition is from day one.

And that starts from having a really strong personal, professional brand. And sometimes that brand can be magnified or amplified through relationships, speaking at a conference, etc. or just amplifying your conversation and making sure that you're drilling down on the things you've innovated on your results and how that connects to the role. Many times when I talk to people about practicing, talking about their value, they're like, yeah, yeah, yeah, yeah, yeah. And they're just kind of testing out their responses in an interview. And that is not okay. You don't need to test anything in an interview. You need to practice before that interview, even if it's just talking to yourself in the mirror and kind of curating the responses to those hard questions. Make sure that you've rehearsed what your value is and how you're going to communicate that so it's crystal clear.

That's really my number one tip when it comes to salary negotiation is creating that alignment with the salary compensation, the role, the title. Even like that last question where the person keeps on getting low balled and getting lower level offers than they'd like. It's what are you saying? What is that gap that’s not aligning with that higher compensation? And many times when we're talking about higher comp, it's about the results that you're able to get. That's why they pay you more money because you're going to get bigger and better results. So how does your brand align with big results?

Anita Brick: I would say that the conversation actually starts before you ever have a conversation. How do you show up on LinkedIn? What is your virtual presence as well?

Kimberly B. Cummings: Yes, everything comes together to really showcase who you are. Even when it's your brand online, you have to think about your total experience that people are seeing about you. And I think all your profiles and all the things online, because we all know that like everybody Googles everything. What are the platforms that impact your professional career? And those need to be buttoned up.

And if you have some crazy whatever online, it's about time you make it private, lock it down, whatever you need to do. So it's not impacting your process because people look. They're looking to figure out more about who you are.

Anita Brick: You're absolutely right. And I think when it comes to compensation, it goes back to what you've been saying all through our conversation. You need to know what you have to offer. You also need to know what the market is demanding or the role is demanding, or the company is demanding and align them at every step, no matter how small, along the way. I think you're totally right. People don't think about it. It's like, oh, compensation is so scary. And you shed this light on it that it gives control back to the person who is a potential employee, where before it's like, well, I'll look and see what the data says, and I don't want to go too low and I don't want to go too high because I don't want to knock myself out. And of course, know what those ranges are, but really solidify in whatever messaging you have, the value that you have. But I also think it takes a great deal of confidence in order to pull it off.

Kimberly B. Cummings: Oh yeah, you have to have confidence. And that's why the practice is necessary. For entrepreneurs, one of the things they always say is saying your prices confidently is one of the hardest things. And if you aren't confident in saying your price, someone doesn't feel like they should pay you that. For salaries the same thing. It's like, you know, for this role I'm looking for and just say it and drop it. Like, if you are my client, I get a little hard on my clients when we'll talk about salary negotiations. I'm like, you say that number and you shut up. Don’t say, oh, you know, I don't want to hear any of that. You say the number you drop the mic and walk away. I think that takes research expertise. You have to be confident in yourself. You have to be super confident in your abilities and just kind of lay it out there. No one wants to get in a job where they're unhappy.

Anita Brick: Absolutely. One thing that I've been doing recently, especially tech tech, tends to be really big packages. Maybe not the base, but once you start putting in the, you know, the RSUs and all of that, you end up with this big package. I was working with someone and she had done her homework. She said, Anita, it's like 225 total comp, all the way to 675 is what I'm seeing. If I give them that range, it's going to be a mess. I said, well, here's what I would do. Put it in thirds–225 to 350, 350 to 5 and then it's 675 a day. You know, I found that these types of roles fall into these three buckets. You know, these three ranges. For this role, what are you thinking about? So now she hasn't locked herself in to either too a low or too high. And now she's getting more information, which actually helped quite a bit. And she did find it was in that middle range, which is totally fine for her. But yeah, but she had to do it confidently. And she like you and many of the Booth students and alums, have a powerful message and it was all good.

Do you have time for one more question?

Kimberly B. Cummings: Of course, of course. Ask away.

Anita Brick: Okay, good. You’ve given us a lot of things, a lot of good information and ways to think about things, exercises to do in the book, and I'd like to bring things together. So if you're thinking about it, someone who really wants to pivot with their strengths. What are three things you would advise someone to do to leverage their strengths, and maybe not all of them?

Kimberly B. Cummings: Go through that long resume. The one you know you can never send anybody. The zillion pages. Go through that long resume and really understand what are the skills that you've gained from every single job. What do you want to continue to do, and what do you never want to do again? Because I think both are really important. And make a list of those top strengths that you want to continue to do in your work. Get crystal clear on what those things are. Essentially, if these things are not a part of your job, then you'd be sad because you're not operating in that area every single day.

Number two, when you're looking to build relationships and you're looking to make that move, really start to be in it for the long haul, start making a list of what your ideal day would look like in this next role. What are the companies that you'd be most interested in working at, and really start to build relationships at those companies with those individuals so you can get that insider information. That's the key. When you have insider information, that's the only way you can really and truly know what that company is like. There's no other way for you to know unless someone tells you, because interviews are everybody putting on their perfect mask. That's really what it is. You got to learn the skill because no one's really going to tell you what's really, really wrong. And even if they tell you what's wrong, you know, it's like 25% of the real problem. Build the relationships so you know and then intentionally prioritize.

Number three, where are you going to go and be patient? Generally, a really good job search can take about six months, sometimes more. So give yourself the time and try to remove the expectation of when you're going to get that job, because it's always better to get the job that builds your career, aligns with your strategy, than to get an old job. And the caveat I always give, I know with COVID-19 and all the adjustments and pivots that have been made, if you need to go get a job now to make the money you need to make, then go get that job.

But still keep looking. Keep looking to find what's really going to bring you joy. Because we spend way too much time at work. And I think now work can feel even more abrasive if we don't like it because we're working from our homes. It's like you can't escape it. You can't turn off and go home. Home isn't necessarily the safety that it used to be. So making sure that you have a career and a job that brings you joy is even more important, especially doing remote work.

Anita Brick: Totally agree. Okay, I said that was the final question. But one final, final question. Clearly you're a rock star. What's the next big dream for you?

Kimberly B. Cummings: Oh my gosh, I love that question. Speaking about the person who said that they don't like really talking about like their accomplishments or they're learning to play small. When it comes to my next goals, I'm learning to say it big because when you say it, then I believe it gets out into the world and you want to–it helps manifest it.

So number one, I want to have a series of books. My next book I want to write on managing management, managing up, managing down, and managing across. Such a big thing that people don't really learn how to be great managers. They just learn how to work and do their craft. But managing people is important. The first chapter of my current book is serving as a people leader is not a rite of passage, it's a privilege. So I want to take that and really expand upon it in my next book. And the thing I always joke is that I want to be the Oprah of career development. I want to make sure that I'm providing the resources, information, education at scale to people who are really looking to take their career to the next level and make their next move.

So I'm still kind of fine-tuning what that looks looks like, building out my consulting company, Manifest Yourself, working with more organizations. Essentially, I'm touching on all the things that I love, but I want it to be at scale.

Anita Brick: Got it. A scalable business is an investable one. That's what we want.

Thank you, Kimberly, so, so much. It was delightful to meet you. I really appreciate so much your mission, but also how you take action in a way that is clearly authentic for you.

Kimberly B. Cummings: Thank you. I appreciate that.

Anita Brick: Great. And thanks again. Thanks for giving us so much today.

Kimberly B. Cummings: Anytime.

Anita Brick: And thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth. Keep advancing.