New York AWE Leader, Judy Jackson on Building Trust, Leading With Honesty, and Embracing Who You Were Born to Be

By: Jasmine Pierik

 Judy Jackson, Global Head of Culture at WPP and Advancing Women Executives Leader.
Judy Jackson, Global Head of Culture at WPP and Advancing Women Executives Leader.

New York AWE Leader, Judy Jackson, was recently promoted to the Global Head of Culture for WPP. Formerly, she was the Global Chief Talent Officer at Wunderman. Judy is a thought leader in human resources management whose career includes stints as chief talent officer at IPG Mediabrands North America and Digitas, and HR roles at Time Inc. and BBDO. Known for her candid, straightforward approach and her unmistakable laugh, she takes a fresh approach to traditional employee programs to develop a culture driven by honesty and transparency.


Recently Judy sat down with our Founder and CEO, Meiko Takayama, in New York City for the second segment of our AWE Accelerator program to share her story. The room was transfixed and by the end of the conversation, everyone was hungry for more. I decided to give Judy a call to dive in a bit deeper to see what other gold we could find.

 Judy (center) next to her best friend, Debbie (on Judy’s right). The two are still best friends today.
Judy (center) next to her best friend, Debbie (on Judy’s right). The two are still best friends today.

Thank you so much for taking the time to connect today. Let’s start at the beginning. Will you tell me about young Judy? What did you want to be when you grew up? Did you always have dreams of ending up in Corporate America?

I am just a black chick from Brooklyn. I was born and bred in Bed Stuy when it was nothing like it is today. My childhood was marked by fun. In fact, I was given the nickname Sunshine because I was such a happy kid! I grew up with 2 sisters and a bother. We have strong Jamaican roots and part of that is having family at the center of everything. Theatre was my passion and I took acting lessons. I guess I thought I’d be an actress when I grew up…I’m still waiting for my big break! (laughs)

My older sister was an actress and she went to Performing Arts High School. Some of my fondest memories growing up were of practicing lines with her. She was my role model, I wanted to be just like her. Although I didn’t become a professional actress, self-expression has always been so important to me.

I don’t think I knew what Corporate America was back then, so I definitely didn’t have dreams of ending up there. But even today, I don’t feel like what I do is “Corporate America.” I see it as providing a service that is needed in all kinds of institutions, schools, etc., and I just happen to be doing it in business.

I read that you studied media and mass communications in college. How did you end up in HR?

I knew I wanted to go into media, but I wasn’t sure in what capacity. I took a class in advertising and instantly fell in love. I started looking for an internship in advertising and found one at a small black owned ad agency. A few weeks in, I knew that was exactly what I wanted to do. When I finished school, I went to a headhunter and expressed interest in advertising and moving to DC. The headhunter liked me so much, he offered me a position at the firm to help candidates so that I could get paid while I also searched for my dream job! A few weeks in, an advertising position at BBDO and a recruiting position at ABC Television surfaced. ABC sounded like the more secure choice, after all it was ABC! I ended up becoming a Junior Recruiter and stayed for five years, until I became the Manager of Minority Recruiting. Those were fun times. I did some interviewing for on-air talent, I was in my 20s, and in the exact space that I wanted to be in.

 Judy and her niece/daughter, Christina. Judy adopted 8-year-old Christina, when she was just starting her career at ABC.
Judy and her niece/daughter, Christina. Judy adopted 8-year-old Christina, when she was just starting her career at ABC.

Then life happened, as it does. I had a string of tragedies mark my life very suddenly. Both of my sisters passed away along with my sister’s husband and I had to be the Executor of their estates. This was a really hard time. My sisters had raised me. As my parents passed away when I was still a child and being the closest living relative, my sister requested that in the event of her death, I would be the legal guardian for her 8-year-old daughter. I was 27 years old, I had just gotten married, and now I was raising an 8-year-old girl. This obviously meant a lot of shift for my life, starting with my job at ABC. After all the tragedy, it became a daily topic of conversation. I had become marked by these tragedies. I wanted to reinvent myself and start somewhere new where I would just be Judy, not Judy who had suffered this great loss. I would later discover that this became a pattern, anytime there was a major change in my life, I changed jobs, too.

Coincidentally, I ended up at BBDO as the Vice President, Manager of Human Resources, where I spent five great years. As you can imagine all of that shift was a lot of pressure for a young marriage. My husband and I ended up getting a divorce – an amicable one – and of course, I felt I needed to switch jobs, because this time I didn’t want to be divorced Judy. If I was going to reinvent myself again, I wanted to try something really different. An opportunity came my way to be the VP of Organizational Development at Planned Parenthood. As a single mom of a 12-year-old girl, I liked the idea of being around young teenage girls. This seemed like something worth trying.

Wow. Talk about a 180. How was that change coming from the world of advertising?

I had no idea how hard it would be. My responsibilities included monitoring our programs and deciding what to keep, iterate, get rid of. At the time I was monitoring a program called, Street Beat. We’d go out in a van in the middle of the night and search for women on the street who were in bad shape and give out condoms, non-perishable food items, etc., and offer an opportunity for the women to get some respite from the street and talk to a counselor. I remember thinking, wow, we are changing the world.

One night, this woman came into the van and shared her story. She had five kids at home, alone, and she would do whatever she needed to do in order to feed them. After talking to our counselor, the woman seemed inspired to make a change in her life. She said she would come in to get more help the very next day. When she left I looked at the counselor and said, “This girl is going to change her life!” The counselor looked at me with zero enthusiasm and ensured me that the woman wouldn’t show up. I woke up the next day excited at the possibility that maybe the counselor was wrong. Sadly, she wasn’t.

In that moment, I decided I didn’t have the stomach for that work. Shortly after I returned to the safety of advertising, a space where, in HR, I felt like I could see a more direct impact of my labor in the lives around me. Although I left, I am so grateful for my time at Planned Parenthood. I learned some big lessons that I’ve kept with me forever:

1. Mission matters. People need to be connected to each other and what they are working towards. You really learn that at a not-for-profit because pay doesn’t keep people around, the mission does. This is a valuable lesson for managers who are thinking of how to engage their team.
2. It’s important to test your dreams. Dip your toe into things that you may want to do, so that you can really find the things that you love. This is one of the reasons why it’s so important for young people to do internships. You’ve got to taste a lot of different things before you can make a decision about what you want to do with your life.
3. Find out what you want your impact to look and feel like. I realized that I needed to be somewhere I could see results, even if my impact was small. I had a dream that I would make an impact and I wasn’t going to be satisfied until I did just that. Working in HR I saw how I could create change in someone’s life for the better and that fulfills my soul. You have to find what works for you. Additionally, it was important for me to learn that not everyone wants to have a huge impact with their work. For some people, it’s simply how they pay the bills. It’s not everyone’s expectation to be truly fulfilled by their job. But for me, I am living my calling!

I can hear the passion in your voice. How exciting to do work that ignites you and leaves you feeling truly fulfilled at the end of each day! Speaking of lessons learned, can you share a story from when you were just starting out that’s really stuck with you?

Yes, I have so many! For years, I’ve been recording episodes that have happened to me in my life and work and the lessons I’ve learned along the way. I am going to compile them into a book in the near future. I’ll share a story from back when I was in school and was preparing to go for my first interview ever. Being a young black girl from Brooklyn meant that if you had an interview, it was time to get your hair done. My sister used to go to this real shi shi salon in Manhattan, and given that I wanted to be just like her and I trusted her, I knew that was just the place.

While I was waiting my turn, there was this older woman there who was in a rush and wasn’t getting serviced as quickly as she had hoped. She was visibly upset about the wait time. Being who I was, I went up to her and I said, “Excuse me, Miss, my sister has been coming here for years and I think you should wait it out. They do an excellent job and I’m positive that you won’t regret it!” I was able to calm her down enough that she decided to stay. When her hair was all done, I made sure to go back up to her and tell her how great her new style looked and she was very appreciative. That was Saturday.

On Monday, I went in for my interview and guess who was the interviewer? None other than the woman from the salon! I tell people this story to remind them that you are always interviewing. As you could have guessed, I was hired on the spot.

I don’t think I ever went out and proactively looked for a job, they all seemed to come to me. And this wasn’t because of some streak of luck, it was because I actively TRY to take care of my resume – and I don’t mean the paper one – I mean the way in which I interact with the world. YOU are your resume. The way you show up. How you treat people. Your reputation. Never forget that you are interviewing every single day.

 Judy and her mentor, Joanne Zaiac.
Judy and her mentor, Joanne Zaiac.

Is there a person that really helped you when you were starting out?

Oh absolutely! There is a woman named Joanne Zaiac. I met her when I interviewed for my first time at Wunderman. Joanne was head of client service then (eventually became a President at Digitas). Early in my career, she was a friend and mentor. She always told me the truth and still does. She stood by me, she shared crucial information with me, she’d always go out of her way to make sure I was okay. When I was pregnant, she even gave me all her old maternity clothes! Joanne taught me that while honesty is hard, it’s also a gift. This is especially rare in advertising, where we are trained to massage the message. Joanne never did that. Instead, she made things look like what they were. I always knew that if I needed to hear the truth, I would get a direct answer from her.  

I try to give that back to people. I do my best to be open and candid. It’s not often that you find people who have the courage to be respectfully honest. That kind of truthfulness is so meaningful, because you know whomever is delivering it is doing so because they care. It’s hard to be honest. In fact, you have to get permission to be honest. You have to build some trust before people can appreciate that level of honesty. Trust has to be the foundation. It doesn’t have to take a long time, it can happen in a single conversation, but the trust has to be there in order for honesty to bloom.  

I’m so glad you brought up honesty, because that’s where I was hoping to steer the conversation next. At AWE that’s one of the things that we admire about you most: the authentic way in which you cultivate trust. I read in a previous interview that when you first conducted employee interviews at Wunderman, the first 4 words people kept saying were, “Can I be honest?” Will you tell me more about how you created an environment where people felt safe to share?

It all comes down to being vulnerable. To listening carefully and checking your intent. You know when someone starts a sentence with, “Can I be honest?” that whatever they say next probably isn’t going to be good news. At Wunderman, we worked to cultivate an environment of trust for employees to share freely. Sure, there are some skills that help develop trust (i.e. truly caring about the individual, being an engaged listener, etc.), but more than that, people sense you and your intent. Call it what you want, your aura, your spirit, whatever. People can tell when you’re authentically looking them in the eye and giving them the permission to be honest.

I also try to create space for people to show up and share. I think people want an opportunity to tell their story, and what happens a lot in business is that no one ever really asks, “how are you?” People are hungry to have their story heard. You don’t need a lot of tools to create trust. You simply need to check your intent, be willing to ask, and willing to hear. When you’ve got all that, it becomes a floodgate, so get ready!

You are in the business of people, but you are also in business. How do you manage building relationships while also making tough decisions that aren’t always easy for the employee?

I try to see people as adults and I try to think about how I’d like to be treated in a similar situation. Pretend for a moment that you have cancer and have three months to live. Would you prefer that the doctor: (1) not tell you, (2) surprise you two weeks before your supposed death, or (3) tell you well in advance so that you have time to think through and plan your last three months of life. I personally would opt for the last option. I like to help people think through what’s in front of them, and see how I can help them get through it.

Let’s simply call the elephant what it is: big, gray, funky, and hard to manage. Hiding the truth from people isn’t helpful and that means avoiding sugar coating as well. When something tough comes up, deal with it, because the longer it sits, the more difficult it will be to manage. In sum, face the truth, deal with it honestly – but with care and kindness – and help the individual through the challenge, sincerely. It also really helps if you make a habit of establishing a relationship of trust in every encounter that you have. Tough conversations and decisions will surface, but if you’ve built a foundation of trust, that will bring some ease to every situation.

 Judy pictured with other senior leaders at WPP, including Mark Read (on Judy’s right), who is her boss and the Global CEO at WPP.
Judy pictured with other senior leaders at WPP, including Mark Read (on Judy’s right), who is her boss and the Global CEO at WPP.

You’ve partnered with top CEOs of some of the biggest companies in the world. Did you notice a pattern in behavior of top leaders? Or in other words do you believe that there is a magic trait that all effective leaders share?

There are magic traits and magic behaviors.

Magic Trait: Not being afraid to make tough decisions and always being honest. I noticed that the most effective leaders I’ve worked with held their integrity high on the list. Mark Read, our WPP CEO, is a fine example of that.

Magic Behavior: These leaders know the value of putting talent at the center of their organization. It’s standard for a CEO to keep their finance head close, but when they also keep their talent head close, that’s a high impact trifecta. In my experience, the bosses that created that trifecta did the best.

What’s your current focus at WPP? What are you really excited about there?

My job is to take the values of WPP and embed them in the fabric of the organization. This is a newly created position and I am 6 weeks in the role. I work with teams across our various regions and companies to help shape their leadership, their talent programs, and ultimately their organizational cultures. In my role I work with others to ensure that the way we go to market, is in line with WPP’s core values – from the tools we use, the behaviors we emulate, to how we work every day, to the training and learning, to the people we hire.

 Judy moderating a panel at the 3% Conference in 2017.
Judy moderating a panel at the 3% Conference in 2017.

Right now, I am focused on building communities. For example, I am bringing our global talent leaders across WPP together to get aligned on how we innovate our talent practices against our values. I plan to do this same thing with our D&I leaders at WPP and so forth. Another thing I am passionate about is finding ways for people to feel a sense of belonging. It’s so important that employees feel that they are connected. That’s what I think helps build a culture. Going back to what I learned at Planned Parenthood, folks need to feel like they are in something together and working towards a mission that they believe in. I can help foster that.

In addition, I want to make sure that I am creating a culture where people feel safe to speak up. About a week into my new role, I met with a CEO. He was under a lot of pressure and I asked him where his safe space was. He told me he didn’t have one. He said he felt like he had no one to trust at work and he didn’t want to bring that stress home to his family. That’s when I realized that creating spaces for psychological safety was priority. Additionally, when people feel safe to speak up it also helps the company avoid major pitfalls. I’m sure you’ve heard the phrase, “the emperor has no clothes.” We need to create work environments where the members of the community not only feel safe to voice their opinions and ask for help, but where they also feel okay telling their boss, “you have no clothes on!”

 Judy (center), her husband, Jon (right), and their daughter, Jonay (left).
Judy (center), her husband, Jon (right), and their daughter, Jonay (left).

Your role requires you to hold space and give so much to so many people. How do you take care of yourself?

I have a fabulous support system. My husband, Jonathan, of 23 years, is my best friend; my 17-year-old daughter, Jonay, attends Brooklyn Tech HS, is an old soul and is easily one of my best friends; I am still very close with my best friend Debbie from 6th grade; and my niece/daughter, Christina, whom I talk to everyday (she actually worked for me at one point!). I have some very close sister friends like Pat, Denene, Pam, and my niece, Mariesa. At work, I have a small knit community that I keep close. I never feel alone. I am comfortable letting people know when I need help. Early in my career, and maybe in the business in general, it wasn’t cool to let people know that you need help. I totally let go of that. I let people know when I need something and I am so glad the culture is changing to encourage more of that.

I have another story related to this from when I was working at Digitas.  One day on a walk to get some coffee, my boss asked me how I was doing with work and otherwise. At the time, I had had to create Excel spreadsheets for the project that I was on and I really wasn’t great at them, to the point that they made me dizzy. I told her that and she said, “Why are you doing spreadsheets? I didn’t hire you to do that. I hired you for your ability with people and teams.” She shared that she had gaps in her skill set and had built a team around her to fill those gaps. This was such a memorable moment in my career where I learned that I didn’t have to do everything.

Stop focusing on the areas that you struggle with and instead focus on what you do well. Build a team around you, to support you, to fill the gaps that you will undoubtedly have, and remember that you are not doing a solo performance.

You mentioned earlier that you are interested in writing a book. I am wondering if you can leave us with one last Judy story to round out our conversation today?

Yes, I’ll share a memory that was a big turning point for me and that I love sharing with others because of Its message around being your true self. I was a junior manager at BBDO and I was working for the head of HR, who also happened to be a mentor.  He called me into his office one day and said that he needed to give me some feedback. I remember being nervous – when your boss calls you in for feedback it’s usually around something that you need to improve.

I’ll never forget this. I walked in and he told me I needed to do something with my laugh, “It’s loud, it’s unprofessional, and it’s bad for your career.” Since he was my boss, I took the feedback seriously. I went home and practiced in the mirror. I tried to quiet my laugh, make it less boisterous and full, but I couldn’t! Whatever fake laugh that I was trying to embrace wasn’t authentic. My laugh is the essence of who I am! I decided that there was nothing to be done about it and that if someone can’t accept my laugh, then they can’t accept me. After that incident, I stopped trying to hide myself. I embrace my laugh. It is my spirit. It is part of me.

That moment helped me discover the importance of embracing who you are. Plus, it was a reminder that it takes too much effort to try and be someone else. And you know the beautiful thing? When you embrace yourself, others embrace you too. The thing that was my “worst” trait became my distinguishing quality! And by being myself, I give others permission to be who they are, and that is the basis of any trust-filled relationship. I should thank that boss! He really gave me such a gift, as disguised as it was in that funny looking packaging. But then again, life’s greatest gifts don’t always come tied up with a big bow.

Thank you so much Judy. This has been a true delight.

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I Wish I’d Known: Advice for the Next Generation of Leaders

We asked executives in our Leader Program for a piece of advice they wish they had received at the start of their career and we’re thrilled to be passing on the knowledge in this bi-weekly series, I Wish I’d Known.

  Chicago AWE Leader, Ann Carter, Vice President, Purchasing and Supplier Management at Baxter , says, “Self-confidence requires constant tending, so try not to beat yourself up if you have moments of self-doubt. Re-adjust and don’t let self-doubt turn into self-sabotage. “
Chicago AWE Leader, Ann Carter, Vice President, Purchasing and Supplier Management at Baxter , says, “Self-confidence requires constant tending, so try not to beat yourself up if you have moments of self-doubt. Re-adjust and don’t let self-doubt turn into self-sabotage. “
bool(false)

I Wish I’d Known: Advice for the Next Generation of Leaders

We asked executives in our Leader Program for a piece of advice they wish they had received at the start of their career and we’re thrilled to be passing on the knowledge in this bi-weekly series, I Wish I’d Known.

  Chicago AWE Leader, Kathleen Cantillon, Vice President, Strategic Communications at an Aviation Company  says, “Fake it until you make it - in other words, you don’t have to know how to do every responsibility listed with a specific role. If you know some of it, are smart, and know how to ask good questions – you will do fine. Believe me, men have no hesitation going for a new job/role that they might not be totally qualified for and you have to think the same way to move up.”
Chicago AWE Leader, Kathleen Cantillon, Vice President, Strategic Communications at an Aviation Company says, “Fake it until you make it – in other words, you don’t have to know how to do every responsibility listed with a specific role. If you know some of it, are smart, and know how to ask good questions – you will do fine. Believe me, men have no hesitation going for a new job/role that they might not be totally qualified for and you have to think the same way to move up.”
bool(false)

I Wish I’d Known: Advice for the Next Generation of Leaders

We asked executives in our Leader Program for a piece of advice they wish they had received at the start of their career and we’re thrilled to be passing on the knowledge in this bi-weekly series, I Wish I’d Known.

  Chicago AWE Leader, Kristen Weirick, Vice President, Global Talent Acquisition at AbbVie  says, “Listen more, speak less, and focus on truly understanding the value that you can deliver based on what you hear and learn.”
Chicago AWE Leader, Kristen Weirick, Vice President, Global Talent Acquisition at AbbVie says, “Listen more, speak less, and focus on truly understanding the value that you can deliver based on what you hear and learn.”
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