686: How to Make Your Next Career Move Your Best Move with Kimberly Cummings

By July 19, 2021Podcasts

 

 

Kimberly Cummings shares her top tips on how to make career transitions easier.

You’ll Learn:

  1. How to make the next best move for your career
  2. The key indicators that it’s time to explore other options
  3. How to identify power players–and become one yourself 

 

About Kimberly

Kimberly B. Cummings is a leading career and leadership development expert and an accomplished speaker and podcast host whose mission is to empower women and people of color in the workplace. Her personal and professional development company, Manifest Yourself, LLC, provides in-person and virtual workshops, trainings, and coaching to professionals looking to lead a dynamic career and life. 

Kimberly has had the opportunity to speak to and create workshops for many organizations, including the New Jersey Conference for Women, Ellevate Network, Urban League, Princeton University and National Sales Network, SXSW, among others. She is also on the Board of Directors for The Power of You Teens organization. Next Move, Best Move: Transitioning into a Career You’ll Love is her first book. 

Resources Mentioned

Kimberly Cummings Interview Transcript

Pete Mockaitis
Kimberly, thanks for joining us here on the How to be Awesome at Your Job podcast.

Kimberly Cummings
Thank you so much for having me. Very excited to be here.

Pete Mockaitis
Oh, I’m excited to dig into your wisdom. But, first, I want to hear a little bit about how you’ve studied vocal jazz for 10 years. What’s the story here? And any interesting adventures come from that?

Kimberly Cummings
So, definitely, I think growing up, I was a kid who always liked to sing. When people asked me what I wanted to be when I grew up, I said, “Whitney Houston.” That’s what I thought was going to be the career path for me, and I took piano lessons for a bit but I kept on trying to sing. But piano takes a little bit more skill to kind of learn the chords and all those things. My voice clearly was much more advanced than my hands were so I went to vocal lessons. And, oh, my gosh, I absolutely loved it, all the great Ella Fitzgeralds, the Sarah Vaughans. I actually performed a 26-song concert in 2005 to raise money for kids.

Pete Mockaitis
Twenty-six songs.

Kimberly Cummings
Yup, I had a pop set and a jazz set. And I say that I’m retired after winning every talent show in undergrad, mind you. I retired. So, now, I only sing for folks who know that I sing. Sadly, it’s more funerals or weddings and things like that. But you can hear me in the shower or in the elevator. There’s great acoustics there too.

Pete Mockaitis
Do you sing in your speaking on stage?

Kimberly Cummings
Oh, no. I’m fully retired.
Pete Mockaitis
Okay. Well, so there we are. So, you’ve retired and you’ve moved on into the world of career and leadership development. So, yeah, tell me, when it comes to people and their careers, often you end up working with folks who feel stuck. What leads to people feeling stuck in their careers?

Kimberly Cummings
Many times, I really believe it’s not having a plan. If you don’t have a plan to take yourself to the next level, it’s very easy to get stuck in your career. Not knowing what your next move is, not understanding what your own skills and strengths and how those manifests in the workplace, a lot of times people can find themselves being underemployed or unappreciated because they have no idea, they’re essentially treating jobs like old boyfriends or girlfriends, romantic partners, in that they’re just like they keep going on to the next. They get a little bored, they go to the next, they go to the next, hoping that it will get better and better and better and it never really does if you don’t have a plan in place to make strategic career moves.

Pete Mockaitis
Okay. Well, then when it comes to forming that plan, where do you recommend we start?

Kimberly Cummings
So, the first stop is really understanding your own skillset and your strengths. I like to have folks who work with me go through a full assessment of all of their strengths, all of their opportunities, all of their weaknesses, their gaps, and really get clear on, “What are the skills that they’ve gained from every single job that they’ve had?” Every single job. That long resume that no one really ever looks at, the one you probably can’t even send to anyone that has every job on there and literally look back and say, “What have you learned? What are your strengths? What are the things you want to continue to use?”

“And what are the things that you no longer want to use? And how can we start to build a career based upon your strengths? And if you don’t have the strengths that you need to get to the next area, what are the things that we need to work on? What are the gaps that we need to attack in order to make your next move?”

Pete Mockaitis
Okay. And so, you mentioned a full assessment. What are some of the key tools or resources or questions or things folks work through to get that picture?

Kimberly Cummings
So, the assessment really begins with you. Where are you? What have you done? What are the key skills you’ve gained from all of your jobs? What is the feedback that you’ve consistently been receiving from leaders? And if you don’t have that feedback, we walk through how to get that feedback using a simple start-stop-continue exercise with people in your industry and people who worked with you.

Of course, there are traditional assessments we can do. I’m a big fan of StrengthsFinder or Strengths Profile by Cappfinity. Those are also great as well but I want the baseline to always be the experiences because, generally, where you’ve gained your experiences, how you gained your experiences, what you’re taking away in terms of skill sets and strengths, that’s the baseline for you making your next move. So, the assessment really focuses on where you’ve been and what you’ve learned.

Pete Mockaitis
Now, you talked about how to get that feedback. So, start-stop-continue is a good way to organize the conversation. But how do you recommend folks specifically say, “Hey, tell me what I should start, stop, and continue doing?” Or, how do you recommend approaching that?

Kimberly Cummings
So, I always recommend finding time to have career conversations with your management. Many times, folks have one-on-ones, weekly, bi-weekly, monthly, or team meetings, and those are focused on doing the work but career conversations are a little bit different. So, I always recommend that people reach out to their leader, and ask, “Hey, I’d love to have a one-on-one with you but focused on my career.” And ask them simple questions like, “What is it that I should continue to do in my role? What are you seeing as good skill sets that I’m building? What do I need to stop doing? What is going to prevent me from moving to the next level? And what do you need to see more of?”

And the big question I always ask for folks who are thinking about making their next move before it’s time for them to make their next move is the big question of, “What do you need to see from me in order to know that I’m ready to get to the next level, I’m ready to make the next move?” so you’re not asking that question when you’re applying for the new job. You want to ask that question well before it’s time for you to have to apply.

Pete Mockaitis
That is a fine question. And, yeah, as I imagine that scenario, I think there’s probably any number of unsatisfying answers you might get, like, “Oh, you’re great. Just keep doing what you’re doing.”

Kimberly Cummings
That’s a fan favorite.

Pete Mockaitis
It’s not quite the right…that’s not helpful.

Kimberly Cummings
No, not at all.

Pete Mockaitis
So, how do you recommend pushing or digging a little more?

Kimberly Cummings
Now, 100% just like you said, that is the age-old, “Oh, my gosh, you’re fabulous. Things are great. End time.” It’s like, no. If you’re not getting good feedback from your leader, I recommend asking other folks, asking your peers, asking other people who’ve also been promoted, and sharing your experiences so they can share a little bit more insight on what it takes to move to that next level.

And then, also, honestly, having a candid conversation advocating for yourself, like, “Thank you so much. I love hearing that you think I’m doing really, really well. However, I want to make sure that I can be extremely planful, that I actually have a plan. Is there any direct feedback that you’d be able to provide me? Like, what is it that means that I’m doing really well? How do you know that I’m doing really well? What are the indicators for that?”

Or, even if you could call up someone else, like, “I saw that Joe got promoted last year into a similar role. What was it that made you know that Joe was ready?” Try and push back to advocate for yourself just a little bit more because feedback is hard. It’s very hard. Leaders don’t like it, employees don’t like it, so it’s really pushing the needle. And if they say that they need a little bit of time to think about it, make sure you circle back and push again.

Pete Mockaitis
That’s good. And I think that is the perfect response along those lines of, “Oh, you’re great. Just keep doing what you’re doing.” It’s like, “Well, I couldn’t help but notice I wasn’t promoted,” in the nice or professional diplomatic way that you get there because, yeah, those are the realities, is that there is something…well, unless the organization is just broken, which I’ve seen some of. There is something that causes people to move up, “What is it? And am I doing it? And how can I do more of it?” Perfect.

And then you mentioned doing this prior to when you start applying to other jobs because you’re ready to be out of there. What are some of the key indicators that it may, indeed, be appropriate to move on and out from a current role or organization?

Kimberly Cummings
So, I’m really big on role mastery and impact. So, when you have essentially mastered your role, when you are doing things with ease, when people are asking for assistance because you know that you have it down, when you’ve built relationships in your role so you have…I always talk about four key relationships that you need. So, you have great peers that you’ve networked with, you have teachers who can help you if you need help, or sometimes people call them coaches, and you have mentors, and you have sponsorships. You have those four key relationships.

If you know where your role fits within an organization, like, “What does your role do?” Every role has a purpose in helping the company reach some type of milestone, even if you feel like it’s a small piece. Like, there’s a reason why that role was hired. Once you really know those things and you could think about, “What is the value you contributed to that role? Have you been able to innovate? Have you been able to move the needle?” Once you’ve been able to do some of those things, then it’s time to start thinking like, “Okay. Well, I think it’s time I start exploring whatever the next move is in this role, whether it’s internal to the company or external.”

Pete Mockaitis
All right. And then if we are looking to transition away, what are some of the most common mistakes you see?

Kimberly Cummings
The most common mistakes I see are people relying on the amount of time that they’ve been at the company. Many times, people are like, “Oh, I’ve been here a year,” or, “I’ve been here two years. It’s time for me.” It’s like, “No, there’s people who’ve been in roles for 10 years who still aren’t ready.” The reality is you have to make an impact. You have to articulate value and what you’re going to do moving into that area.

And I’m not sure what your feedback is on what I’m about to say next, but I think that, many times people want to not do a tinge more work to showcase that they’re ready for the next role, especially for folks who are moving internally. They’re a manager, want to be a director. An analyst, want to be a manager. Whatever it is.

But what I explain to folks is that in your role, you’re essentially in a box. Like, this is the role of the manager. You’re doing everything that needs to be done within this box. When you’re ready to move to the next box of the director, you have to showcase that you’re ready to leave that box to go to the next level. And in order to showcase that, you almost have to show people like a little bit. Give them a touch of what they’ll see from you as a director. And it’s important that you start doing a few of those things, making sure that you’re aligning more to a director role than you are to a manager role so people can literally see you in it.

A lot of times, when there’s a job search that’s happening, I used to work in talent acquisition as well, and when you have someone who is internal applying to a job, and you have someone also who’s external, the internal person, you’ve essentially been in the longest interview of your life. They see you every single day. They know you. And if they have questions, like, “Well, why didn’t so-and-so start doing this already? Well, l really don’t see them doing this. They’re doing so well in their current role.”

Versus an external person can come in and just sell them the world because they don’t know them, they’ve never seen their work, and they can easily align to that director role. So, I think it’s really important that when you’re thinking about moving, you start thinking a little bit more on the level you’d like to be on versus the level that you’re currently at.

Pete Mockaitis
Absolutely. And, well, if you wanted my feedback on what you said with regard to doing a touch more work, I think that’s the right answer to advance in your career. But I think it’s also true, what you said is that a lot of people don’t want to do it, yeah, because it’s like, “Well, I’m not getting paid for that. I don’t have the title. It’s like they’re not paying me to do that, so it’s unfair or not justified in the give-and-take relationship between me and employer to do that while being paid what I’m currently paid.”

But what I’ve seen is that frequently your fastest movers and shakers are already doing the next job, and the promotion is kind of a formality, like, “Hey, you’re already doing this. We’d be embarrassed if we didn’t give you the title or the raise, promotion, etc. associated with that.” So, yeah, I think that’s kind of how it shakes out.

Kimberly Cummings
Oh, God, I’m happy we’re aligned there because some folks are like, “Nuh-uh, don’t give them a preview till you get the paycheck,” and I’m like, “Nah, you get the paycheck when you give them a preview.”

Pete Mockaitis
Right, yeah. Indeed. And so then, when it comes to the networking world, you’ve got some perspective on identifying power players. Can you tell us how do we find them and build great relationships with them?

Kimberly Cummings
So, in every industry, I strongly believe that there are power players. They are people who are at the head of the curve, the people who are the key stakeholders who everyone listens to. There are always a few key people that are great to really look at as sponsors in your network. So, the way I always try to identify them are looking up professional associations. Who’s speaking at the conferences?

If you’re at the conferences, virtual or in person, whose room is packed out every single time? Who is it that has your boss’ ear or your skip leader? Who’s the person who really has the power to make the decisions and you see being frequently called upon? Those are what I call the power players, the people where a business doesn’t happen unless you hear from them first, where they have a significant influence over whatever is happening in the workplace.

When we’re talking about power players, one of the key words there is influence. Same thing with sponsors. They have to be able to influence and impact change. Otherwise, they really aren’t a power player in the industry. So, when you start seeing people speaking at events, or people always tapping that person, you know that person has power in the workplace. And my key is always finding a way to get in the room with them. How can you get as close as possible, again, virtual or in person?

I think you could still do it virtually. In some respects, virtual can even be a little bit easier than trying to navigate yourself into a room in person. But find a way to get in the room. And whether it’s interacting with that individual at the event, even as simple as asking a really great question, or being super active in the virtual chat. Find a way to get involved with that power player and initiate some time, whether it’s a 15-minute meeting to introduce yourself, learn more about them, or attending quite a few events.

If I’m very honest, there are some people who I have relationships with now where it took me years to build a relationship. It wasn’t one time to get on their radar. It was multiple events, multiple things before I reached out and got any individual time with that person. I think, especially when you’re looking for someone who has influence, it’s going to take some time. It’s not going to be a quick one, two, three the first time you try to hear back.

And if you can’t get in touch with that person, I recommend also looking at who’s around them. So, let’s say there is a senior SVP in your workplace and you want to get in touch with them but you know you have not had any luck on getting on their calendar. Well, then who are their direct reports? Let’s see if we can get in contact with them and work your way around, so the next time when you try, you already have some relationships that are close and someone else who can refer you or make an introduction. Sometimes it takes a little bit more time to get that power player.

Pete Mockaitis
Okay. Very good. And so then, so you stick with it and you keep your eyes open. You ask for those recommendations and you’re watching. And then how do you yourself become such a power player?

Kimberly Cummings
Again, I think that’s so much about impact and value. It’s about being a subject matter expert, being the SME in your area. Many times, people believe that leaders have to have this big title, they have to be the SVP, the director, the super long title that is confusing, and you can barely say it yourself. But I really believe that everybody has the ability to be a leader.

You are hired for any particular role. That role has tasks and responsibilities. Regardless of your seniority, you need to be the subject matter expert for your role. Nobody needs to do that role better than you are doing that role. You have to lead in that role. When you are leading in your role, so you’ve mastered it, you are the person who they come to for questions or concerns, you have networked yourself appropriately so people also know that you are the best at that role.

You’re not just behind closed doors or in your virtual office, not speaking to anyone. That’s really how you can start positioning yourself as the go-to person and, ultimately, positioning yourself as a leader or the power player in your area. And, also, having that strategy, so knowing what’s next, which means having some of those tough career conversations even if your leader isn’t kind of giving you what you need, making sure that you kind of push forward or find someone else who can give you that feedback.

Having that strategy so you can continuously be evolving your career and moving to the next level, that will slowly but surely be able to position you. And, you know, for some folks, it takes time. For me, even thinking about my own career, for a long time, my goal was to be a director of career services in higher education. I spent nearly 10 years in career services offices working with people at 18 who don’t know what they want to do with their entire life, to people who are in their 60s who want to use all their experience and use that to kind of launch into something that just makes them happy in the world of work.

And I wanted to just be a director of career services running a large office. That was it. And I knew that in order to move to the next level, this wasn’t an arena where I’d be able to stay in one office unless I wanted to stay in one office for like 10 to 15 years to slowly work my way up. So, every two years, I made sure I knew what my next move was, I understood the skills that I needed to gain with each strategic move in order to build a career for myself, and also increase my influence.

I participated in conferences. I spoke at conferences. I always made sure I was able to level up in my career. And, ultimately, I did not get that director of career services job, but I became a director in a global Fortune 100 company in financial services leading some of their diversity talent acquisition recruitment efforts. So, you just have to make sure that you’re continuously leveling up and having a strategy for yourself.

Pete Mockaitis
Well, thanks for sharing your story there. And could you share also the story of someone you think did a fine job of kind of integrating all of these learnings and seen some cool results?

Kimberly Cummings
Definitely, success stories. Like, everyone always loves success stories. I have a current client who I was working with who came to me because they were feeling stuck, they’re in one of those jobs that we talked about earlier, Pete, where they were just kind of over it. They felt underemployed, definitely underpaid, and they really wanted to start positioning themselves for leadership roles.

Then when we first started working together, she just wanted to get on track. So, we went through the assessment, we went through kind of understanding all of the skillsets, was she in a career that was aligned to what her goals were. And at that time, she was but she didn’t have the level of seniority that she wanted. She didn’t have the impact that she was looking for.

So, for that particular person, we worked a lot on the relationships. How can we start making sure people know about the work that she’s doing, networking, cultivating some of those sponsors, some of those mentors? And, in about three to six months, I think probably around the five-month mark, if I have my memory serves me right, she’d been applying to jobs and she finally landed a role.

And because she’d done so much work with building relationships, understanding her own personal and professional brand, she rocked this interview process, making sure that she was finally positioned for a role. A lot of it was the language she was using to make sure that she was no longer underemployed and being in a role that was in much better alignment.

She negotiated a $35,000 salary increase. She got added to a committee right away that was aligned with some of her career goals. And she was able to speak a lot about career pathing even in her interview process, so she knew what would be the next step for her, being very candid about looking for longevity in an employer and not just for a defined role.

Pete Mockaitis
Beautiful. Well, thank you.

Kimberly Cummings
No problem.

Pete Mockaitis
Well, Kimberly, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Kimberly Cummings
No, I think this is good. I think you had me cover it all. I love how actionable all of our questions are.

Pete Mockaitis
Thank you. Well, now could you share with us a favorite quote, something you find inspiring?

Kimberly Cummings
Yes. So, there’s a quote by India Arie. It is, “The only thing constant in this world is change.” I put it in my high school yearbook, and I think it’s so, so, so true.

Pete Mockaitis
And do you have a favorite study or experiment or bit of research?

Kimberly Cummings
I really like the research on diversity, equity, and inclusion when it comes to privilege. I’ve been doing a lot of research on that, kind of looking into more of the privilege walks. I know Drexel has a lot of information on that arena.

Pete Mockaitis
All right. And a favorite book?

Kimberly Cummings
So, my new favorite book is Winning is Everything by Tim S. Grover.

Pete Mockaitis
All right. And a favorite tool, something you use to be awesome at your job?

Kimberly Cummings
I think StrengthsFinder, the assessment, is one of my favorites. It helps you understand yourself.

Pete Mockaitis
And a favorite habit?

Kimberly Cummings
I live and die by a planner and a task-list system that I use. I have it every day.

Pete Mockaitis
Well, I’m now intrigued. What’s the system?

Kimberly Cummings
So, I use Asana but better than that, I really do it in my notebook every single day. I prioritize my tasks by functional area, and for my business, by revenue impact in order of importance. I have a little color code system too. I’ll have to take a screenshot for you, but it helps me knock out even more every single day by having all those priorities in line and make sure that I’m working on what actually needs to get done versus the mini-tasks that we do all day that keep us from doing the big thing that we should be doing.

Pete Mockaitis
And is there a particular nugget that you share that really seems to connect and resonate with folks; they repeat it back to you often?

Kimberly Cummings
A lot of it is around confidence. I think I have a quote from my business, my manifesto that I always share. It’s, “You must believe in yourself and your vision. When you do this, you’ll manifest the life you desire.” And I share this a lot because when we’re trying to make any type of career change, I think the number one thing you have to do before we get into all the strategy pieces is believe that it’s actually possible for you.

And a lot of times, when we start talking about that, people are like, “Oh, my gosh, like that really resonates. Like, I didn’t even think that that was important. Maybe that’s why I haven’t been moving.” It’s, like, you have to believe that whatever you want to do is possible for you.

Pete Mockaitis
And if folks want to learn more or get in touch, where would you point them?

Kimberly Cummings
I would point them to KimberlyBCummings.com. I’m also on all the social places. So, Instagram and LinkedIn are probably my favorite. LinkedIn, it’s my name, and Instagram is kimbcummings.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Kimberly Cummings
Yes. So, shameless plug or not so shameless because you said I can share. But I’m a very brand-new author. So, in June 2021, I wrote a book Next Move, Best Move: Transitioning Into a Career You’ll Love and it is available wherever books are sold. And this is the process to help you put together a two-year career strategy.

Pete Mockaitis
All right. Kimberly, thank you. This has been a treat and I wish you lots of luck in each of your moves.

Kimberly Cummings
Thank you so much.

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