The Feminine Founder

162: {Interview} Navigating Change with Jessica Jacobs

Caroline Pennington Season 2 Episode 162

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In today's conversation, I sit down with Jessica Jacobs, a change management expert and entrepreneur, who shares her journey from corporate America to starting her own consulting practice. Jessica reflects on her extensive experience in Fortune 15 companies, highlighting the lessons learned about personal passions and the importance of adaptability in the workplace. She emphasizes that the transition to entrepreneurship was driven by a desire to make a more significant impact in the realm of change management, where she and her partner, Alison, could implement innovative strategies to facilitate transformations in organizations.

The discussion delves into the nature of change, both on an individual and organizational level. Jessica explains that while change can be uncomfortable, it is essential for growth. She offers practical advice for navigating change, such as embracing micro-experiments to ease into new habits. The conversation also touches on leadership qualities, emphasizing kindness, transparency, and the importance of emotional intelligence. Jessica concludes by encouraging listeners to focus on small, consistent steps toward their goals, reinforcing that everyone starts somewhere and improvement comes with practice.


takeaways

  • It's all about the pivot
  • Everybody sucks at first
  • You can't grow without feedback
  • Focus on micro-experiments to ease into change
  • Kindness is a powerful leadership skill
  • Small steps compound into big changes
  • Emotional intelligence sets great leaders apart
  • Change is uncomfortable but necessary for growth
  • Trust your team and delegate effectively
  • Be open to feedback from all directions

Learn more about 3 Keys Consulting HERE or connect further with Jessica on LinkedIn HERE


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ABOUT THE HOST:

Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called The Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara.

This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.

Let's connect further!!

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IG @cpennington55

FB HERE

ChilledVino HERE


Caroline Pennington (00:00.371)
Welcome, Jessica.

Jessica Jacobs (00:01.794)
Thank you, it's so good to be here.

Caroline Pennington (00:04.287)
So you and I have known each other now for some time and we met originally on LinkedIn and now have become fast friends since. But I want you to tell our audience, tell me about your story. You've had some really big corporate jobs. You worked in corporate America a long time and then you've gone out being an entrepreneur the past two years as a change management expert. So I want to hear your story.

Jessica Jacobs (00:09.398)
Yes.

Jessica Jacobs (00:17.474)
Hey, Dad,

Jessica Jacobs (00:25.42)
Yeah, so like you said, I've been, spent the bulk of my career in corporate America in Fortune 15 companies and it was a really great and really powerful experience and I learned so much about who I am. I've learned about the work that I like to do. I found a lot of my passion through being in these large enterprises. I learned also what I don't like.

And I really enjoyed all my experience that I had there. And it also brought me closer when I talk about my passions to bringing me into a space where I finally felt like I was ready to leave corporate America and start my own consulting practice with Alison, my business partner. And we ultimately left because we've been doing change

in large scale transformations in these very big companies. And although we really loved it, we also saw there was a different way to do things and a way to do it where we can make a bigger impact. And that was really what pushed us over the edge, I think, into this new space of entrepreneurship. And we haven't really looked back. We both really enjoy what we're doing and it's really exciting and fun to be here.

I wouldn't have gotten here in the way that I am today though, without that past experience. It made me a leader. made me all these other great things that helped me build who I am with Three Keys Consulting or practice. And, you know, I think the biggest lesson that I've learned along this journey has been that you take everything that you've built.

And it just, and it continues to just follow you into new spaces, into new ways of being. And that's what I've done. I've taken everything I've learned. I've been able to, thankfully I'm very good at experiencing and seeing patterns. And so I'm able to use those and to apply them to the work that we do when it comes to change and transformation. And, you know, what we discovered really through our work in-house in corporate America is that

Jessica Jacobs (02:52.906)
things easily derail. Things easily move into directions that you're not expecting. And if you aren't working with people who can ebb and flow with things and can be flexible with the way things go, it becomes very difficult for success to happen. one of the things that Allison and I met, the way, when we were working together in corporate America. And so we've known each other for

We're getting close to, think, 10 years at this point. We've known each other and we decided we loved working together so much that we were going to start our own practice together. But through that, we really discovered that what works for us and helps our clients, whether they were in-house or now the ones that we work with, is that we're very easily flexible. We can move and we switch directions as necessary and we're able to

to pivot in the ways that we need to because anything in life, in work, in being an entrepreneur, it's all about the pivot. You can't do things really without that ability to move and to quickly shift.

Caroline Pennington (04:09.013)
All right, so let's talk about this. I'm just jump right into it since we were just talking about it before I press record and you're kind of leading up to it right now. But let's talk about the topic of change. Why is change necessary on an individual level and on a company level?

Jessica Jacobs (04:17.677)
Hmm.

Jessica Jacobs (04:24.319)
well, change is necessary in every way we go. What I said to you before, Caroline, was none of us really like it. It feels uncomfortable. And if we can talk about all the reasons it feels uncomfortable, and I could talk about those for literally for hours, I think, though, we just kind of get into this way of being and comfort that we find in life as an individual.

As individuals, whether you're making a change because it's a personal change, you want to get healthy or you want to get fit or you want to learn a new hobby or a new skill, these are all changes that we make to our life. Some of them feel really good and really exciting. Others don't. And if we even think about the things that do feel really exciting on an individual level, traditionally happy things.

You're married, you're moving in with somebody you love, you're building a family, you got a new dog or a new other new pet. These things all feel really great. And Caroline, you've got two dogs. Remember what it was like bringing home puppies?

Caroline Pennington (05:31.869)
is the best feeling ever until they wake you up at three o'clock in the morning and have to pee like every single hour. But yes, continue.

Jessica Jacobs (05:37.43)
Yes, yes. And all of a sudden, all of a sudden, you're going, what have I done? Right? You've got one foot in the old way of living. You've got one foot in a new way. And you're very wobbly and you're trying to make this path forward. But it is so uncomfortable. And it's because you're growing. It's because you're you're experiencing this shift and change of who you are in so many ways.

Caroline Pennington (05:44.317)
you

Jessica Jacobs (06:07.606)
And that transitions over also into work. The things that we do at work, the changes that either happen to us or with us, they're all about this shift in equilibrium and all about identity shifts. Right? If I was this, if I was this person at work yesterday and now you're me, this person today, who am I? How does that change who I am as an individual? And that's a very hard experience to work.

through.

Caroline Pennington (06:39.861)
What's your best piece of advice to someone who's going through a season of change?

Jessica Jacobs (06:45.814)
Enjoy the ride. Find ways to experience it. Be open to it. Think about the things that are going on. Focus on it a little bit. Put a spotlight on what's changing for you. And then spend some time with micro experimentation. I say micro experimentation because it feels safer and it is safer. These are like the little tiny shifts that you can make to get to where you want to go.

Maybe that's if you are wanting, I have a few friends who are about to run a marathon this year. And so this is top of mind for me, right? They're not, neither of them are particularly runners, but they are going and they made this goal to do it. This is changing a lot about their life right now. So they're not going out and running that marathon tomorrow. They're making these small little changes, small little shifts every day, running a little bit more.

seeing what this does, trying out that, right? You experiment in small ways to see safely how you can live in a new way.

Caroline Pennington (07:56.179)
Yeah, I talk about this a lot. The tiny steps that you make compound in really big ways and the game changer is staying in it. So I don't care if it's you want to learn a new skill, you want a new job.

you want, whatever fill in the blanket is just take tiny steps every single day. And everyone's busy. We all have stuff going on. We all have family, kids, parents, dogs, whatever fill in the blank. But if you just take literally, it can be less than 10 minutes a day to make steps towards whatever you're trying to change. can literally, you will look back in three months, six months and be like, holy moly.

Jessica Jacobs (08:36.671)
Yes, it's those little tiny things. like there's an illustration I've seen out there that little droplets of water filling the jar, right? Each day a droplet comes in, each hour a new droplet comes in, eventually the jar is full. It's all about the compounding effects that we have and the work that we're doing to always move ourselves and progress ourselves to the next phase.

Caroline Pennington (09:01.53)
And I'll add to this too, like if you're listening to this podcast and you're like, well, I'm not good at fill in the blank, whatever it is you want to do. Guess what? When I started this podcast, I didn't know what the hell I was doing. I was not good at it. Now, two and a half years later, I'm much better at it. So listening to this, don't be discouraged. Keep going, take the tiny steps and you will have a great outcome. I promise.

Jessica Jacobs (09:13.934)
Yes!

Jessica Jacobs (09:26.56)
Absolutely, you know, I say this to my kids all the time. Everybody sucks at first.

Caroline Pennington (09:33.781)
Yes, I love that story, by the way.

Jessica Jacobs (09:35.022)
And I don't know, maybe they may not find as much comfort in that as I do, but if everybody sucks, that means you're in good company, right? You're in good company. If they suck too, and now you see somebody who you really admire, you know, we're talking about podcasts, right? So Amy Poehler just won the Golden Globe for hers. Yes, but Amy Poehler didn't wake up one day, Amy Poehler.

amazing actress, podcast host and all these other things. She woke up and was sucking on the stage of the Bright Citizens Brigade or one of these other, you know, whatever it was. But we all start off sucking and to become that person, you got to embrace this sucking a little bit.

Caroline Pennington (10:23.829)
Oh my gosh, I'm so glad you bring up this topic because I love talking about this because so many people I talk to, so many women are like, well, I don't want to look stupid or I don't look silly to whatever, fill in the blank. And I'm like, Michael Jordan didn't start as a basketball star. Like he put in the reps, you got to put in the reps. And if you're not willing to put in the reps, then you're not going to get the outcome that you want.

Jessica Jacobs (10:46.35)
100 % and we've all got to do it and the only people who think that that you look stupid is yourself and this is what I've learned.

Caroline Pennington (10:56.341)
And also people are so consumed with themselves. Like they're not looking at you. They're not paying attention to you. So even if you feel embarrassed or feel like you don't want put yourself out there or you don't want to go through the suck, keep in mind like the people are not even paying attention to you. And they're going to talk about you anyways, by the way. So why does it give them some talk about.

Jessica Jacobs (11:17.006)
Yeah, right? Make it good and juicy. And it makes me think, Carolyn, one of the things, a piece of advice that you gave me when we first met was nobody's paying attention to you as much as you're paying attention to yourself. So you post a picture and you think you look terrible. They're not thinking about that. They're just thinking about what you wrote about and looking at the picture and moving on. Right? That's it. We get so caught up in our heads of all these other things that nobody has time to think about.

Caroline Pennington (11:43.317)
It's so funny, I had a meeting with someone recently and they were all caught up in that. And it actually was specifically about LinkedIn. And they were like, I don't wanna appear like whatever fill in the blank to these Fortune 100 leaders. I'm like, guess how much time those Fortune 100 leaders spend thinking about you on LinkedIn? Zero.

Jessica Jacobs (12:02.286)
They've got a whole lot of other things that they're thinking about. you know, I've worked with a lot of them and they're all wonderful people. They also have very busy lives, very busy. And so when they come onto LinkedIn, especially they're coming on because they want to catch up and see what's going on. They want a quick insight and they want to see what people in our network are doing. That's it.

Caroline Pennington (12:27.817)
Yeah, so true.

Jessica Jacobs (12:28.76)
They're not coming on there to judge one person over another.

Caroline Pennington (12:35.061)
So I want to hear from your opinion. What makes a great leader?

Jessica Jacobs (12:38.242)
Ooh, there are a few things I think make a great leader. One, and first and foremost for me, but it's one of my values is kindness. And I say this and inevitably somebody out there is gonna be rolling their eyes around it. But here's the thing, I don't think that it's a soft skill. I don't think that it's something that nobody can do. Everybody can do it.

Everybody can extend a little bit of kindness every day. And it shifts and changes so much about the person that you're speaking with and their world and how that kind of continues to expand outward with from just one tiny act of kindness. And we all have lives outside of work and we don't know what's going on with our employees or our peers or our managers, right? And so if we...

can extend that kindness to others, it pays you back tenfold. Number one. Number two, I think is the ability to be as truthful and honest as possible at any given moment. And to be very clear around what your expectations are, what's going on, where are things heading? And as leaders,

We can't always be 100 % transparent. That's just the nature of life. But to be able to walk up to the line and share things makes such a big difference for so many people and it builds really strong relationships. And the third one for me is the ability to delegate. As we move up in organizations,

And it goes back to this whole thing around identity too, right? The more we move up in organizations, the more we have to shed the things that we were doing before so that we can take different views and perspectives within an organization. The only way to do that is to trust your team, to trust those around you and to delegate the day-to-day work and trust that they're going to do that really well.

Jessica Jacobs (14:44.386)
so that you can make the thoughtful strategic decisions that need to be made and to bring them into the mix as along the way too. And sometimes that means there's a meeting you can't make it to and delegating that to another person. And what I will say about this also is if you're going to delegate, you gotta be very clear around what this means. What kind of decision rights does the person you're delegating to have?

where do they need to come back to you, what do you want them to come back and share with you so you're not missing something from that meeting also. And to make sure that you're being very clear and giving them these opportunities to grow and to experience different types of settings within the work environment.

Caroline Pennington (15:32.553)
Yeah, I feel like the best leaders that I've at least worked under the trust and the transparency and you're right. Like you can't tell me everything that's going on. I get it. But at least let me know like what the expectations are, what the timeline is or like those things as go a really long way and they seem really simple, but they go really far. I love that you're number one.

Jessica Jacobs (15:46.956)
Yes.

Jessica Jacobs (15:51.724)
Mm-hmm, absolutely.

Caroline Pennington (15:55.647)
Pillar was kindness because I think there's this misconception out there that if you're a leader or if you're an executive or entrepreneur or whatever, it's like you gotta be a hard ass to be successful. And I don't think that at all. I think you can be successful and be kind.

Jessica Jacobs (16:11.321)
100%. And, you know, kindness is different to me than being nice also. Those are two different things. And kindness takes many different shapes in the work world. Sometimes kindness is being very clear around your expectations. Sometimes it's kindness is giving the feedback that maybe you don't want to give, but you know it's going to help somebody grow. Kindness is extending

a warm smile even, Like bare bones minimum, a smile is still an act of kindness. And they can change something in a person and their day. And you just don't know when that's going to happen.

Caroline Pennington (16:37.941)
I worked by this rule of thumb before when I worked in corporate and I do it now as an entrepreneur. I treat people like I'm going to be treated.

Jessica Jacobs (17:01.228)
Mm-hmm.

Caroline Pennington (17:02.001)
And that's the golden rule. That sounds like, again, very simple, but especially when you get into tough conversations or have to deliver the hard feedback or whatever, fill in the blank, it does get more difficult to do. But I think it goes a really long way too.

Jessica Jacobs (17:17.326)
100%. If you know that you're staying true to yourself, that then gets felt by the others in their room. And I think that's what you're describing is a form of authenticity too, right? This is what I know I would need and what I would want to see from somebody else. So I'm going to put that out there into the world. And...

I know enough about you and so many others that that's not where it stops. You know, it's also about then recognizing that sometimes what we need isn't what another person needs and starting as a leader to understand what is it that your teammates need? What is it that your coworkers or peers need and helping be that person to them when they need it most?

Caroline Pennington (18:11.237)
What skills do successful leaders have in your experience?

Jessica Jacobs (18:18.06)
They are wonderful listeners.

they move away from their technical skill and move into more skill around development and

they develop on their own, the more of a growth mindset and how they continue to experience the world is a huge skill to have. And not one that we're all necessarily born with. That's one that sometimes you got to push for. Growth mindset is tough.

Caroline Pennington (18:57.281)
Yeah, the number one question I used to get asked when I was recruiting, when I was working and recruiting as a headhunter, but I was recruiting in the C-suite space. So like the really high income earners, the high six, seven, eight figure income earners. And people would ask me all the time, they would say, what did these people have that you placed in these jobs? And I would, the answer was the same every single time. I don't care what job it was. I don't care what industry it was.

I don't care how big the company was, multi-billion dollar company or small 10 people or less. They have good emotional intelligence.

Jessica Jacobs (19:24.963)
Mm-hmm.

Jessica Jacobs (19:29.27)
Yes.

Caroline Pennington (19:31.689)
And that was it. And that's something you can't teach. You have to acquire it or learn or work at it and always work at it. But that was the game changer, what set those people apart from the people that were not functioning at that quite high level.

Jessica Jacobs (19:33.006)
Mm-hmm.

Jessica Jacobs (19:48.17)
Yes, absolutely. It's such an important skill to have and to grow into. And I think, you know, part of that is also building our own self-awareness.

Caroline Pennington (20:03.516)
Yeah, that goes a really long way. I didn't learn that until my 30s. Guilty.

Caroline Pennington (20:13.745)
So as a leader, do you think you should be open to feedback from your team of like how you are as a leader and how your team is experiencing you?

Jessica Jacobs (20:22.91)
gosh, yes, I don't know how you can grow without it. You get feedback ought to come from every direction, up, down, and across. You have no other way of knowing.

that can be a really tough pill to swallow sometimes too, especially when you think that you're doing things really well and then you hear it's not working for everybody. I think that although it can be hard to experience hearing that, what I tell people

when they're getting feedback is to remember that this other person is taking time out of their day and putting themselves in a very uncomfortable position to tell you something. And they wouldn't do that unless they cared about you. They wouldn't do that unless they wanted to see you grow. And so if somebody is stepping so far out of their comfort zone to give feedback to their own manager,

Caroline Pennington (21:23.085)
That's such a great advice.

Jessica Jacobs (21:33.08)
you have to listen to it and hear what they're saying and turn it into a conversation because you might really believe that what you were doing was the right move. And they're maybe saying, I didn't experience that way. And so maybe that's an opportunity for you to understand where did intent and impact not align together and how do you accomplish your intent?

and make sure that that impact is still felt in the way that you wanted it to with the other person.

Caroline Pennington (22:03.201)
How do you know if you're having impact?

Jessica Jacobs (22:09.406)
Sometimes it's really easy and you can see the growth in another person. You can see that you're growing yourself or you're seeing other people around you grow because of something you did or a program or project that you're working on is really taking off. And those are the really easy ways to see things. Those opportunities though, I think are few and far between.

because it's like one day you wake up and you realize, my gosh, I'm doing something I never thought I would do. Or, my gosh, this person started working with me and they couldn't even imagine doing X and now they're doing X, Y and Z. And you wake up one day and it's this big epiphany, but that's not enough to keep you.

moving and excited and seeing that impact. And so what I often say to folks is to think about it and be a little bit more intentional about what your goals are or what you're working towards and what that might look like. And to think about what does the smallest little bits of success look like? Because every day something is shifting. And so that might be these really small moments. And it might be because you had a micro experiment and

It went really well. And you saw from that micro experiment that you actually had a big impact or even a small impact. But what's the overall impact that you're looking to build? And how do you know that you're taking these little tiny steps to build that big impact? What are those?

Caroline Pennington (23:48.089)
That's such great advice. And even it's like working backwards. You have this big goal and then what steps do need to take to actually get there? I love that. So, okay, as we wrap up, how can our listeners find you?

Jessica Jacobs (23:53.774)
Yes, exactly.

Jessica Jacobs (24:01.858)
You can find me on LinkedIn, Jessica Jacobs. You can also check out our website, threekeysconsulting.com. And you can find me here on this podcast. I'm always commenting on things that Caroline posts on LinkedIn too. Come on over at LinkedIn, I'm here. Thank you.

Caroline Pennington (24:17.905)
Just head on over to LinkedIn and you can find her.

Thanks, Jessica.