Inside the Office with Theola DeBose

Inside the Office WITH

THEOLA DeBOSE www.eyemaginationimaging.com

Inside the Office with

THEOLA DeBOSE

2

C - SUITE PICS® MAGAZINE - INSIDE THE OFFICE

A Division of Eyemagination Imaging

1. What is your “day job”?

I am the Chief Operating Officer of GraySide Media Group, a crisis management and communications firm that I co-founded with my husband. We position people who are doing work that is good for the world to tell their story with purpose, across all platforms, so that they can receive recognition and

C - SUITE PICS® MAGAZINE - INSIDE THE OFIFCE

3

respect. Our clients tend to be unknown, undervalued or underrated in some way and have a deep desire to make a contribution. That includes charter schools and nonprofits to edtech firms, real estate agents, and journalists. I am also the founder and host of a podcast, “The Gray Side: Life After Journalism,” where I interview former journalists like myself about forging a new career and identity after leaving the news business.

2. Who were your heroes, or mentors?

My mother. She was born and raised in Haiti and came to New York City in her 20s. She married my father, learned English and earned an associate’s degree, a bachelor’s degree and a master’s degree. She had a long career as a hospital OB-GYN nurse and later, as a health administrator. She has a great laugh, wears bright colors with pride and speaks her mind. She taught me determination, honesty, and humor, and that I should knock down any barrier, real or imagined. She was never a business owner but I certainly rely on her example and inspiration as I continue on my entrepreneurial journey.

4

C - SUITE PICS® MAGAZINE - INSIDE THE OFFICE

A Division of Eyemagination Imaging

3. What is your best childhood memory?

Sundays. My parents, older sister, younger brother and I would dress up for Catholic church.

Afterward we would come home and my father read the newspaper while my mother prepared dinner. We always had the largest meal of the week on Sundays. We children played games with each other while Haitian music and news came through on the radio in the living room, and I was happy that I could understand the Kreyol that was being spoken. We did this every week. I loved our ritual of food, faith, and family.

4. What traits did you possess as a child that resembled traits of a leader? Do you have a funny story?

I wasn’t afraid to challenge authority or speak honestly. Sometimes too honestly. One time, when I was about six or seven, I got in trouble because I told some friends of my parents who had come over that when we children were cleaning up before they came, we found a dead bug under the bed. It was true, it happened! But my mother was not amused by my sharing.

C - SUITE PICSÂŽ MAGAZINE - INSIDE THE OFFICE

5

Leadership often requires bringing up things

I knew I loved writing and talking about

that aren’t all that pleasant, and that others

schools. And education had played such a

may not want you to share. But I’ve never been

critical role in the lives of my immigrant

afraid to speak about those kinds of things. If

parents. That’s how I ended up joining DC’s

anything, over time I’ve learned the role of

charter authorizer and leading all of the

filters and how and when I should apply one to

communications efforts and external affairs.

myself. It’s a balance, but in general I lean

We had some great successes, like publishing

toward saying what I believe needs to be said.

the first-ever Parent Guide to Charter School Quality, which now comes out annually. And

5. When did you decide you would be

then I served as a communications leader in the Obama administration at the cultural

communications professional, that

agency that gives grants to institutions like

this would be your journey?

colleges and universities. On a very short timetable and no budget, I designed a digital

This is my second career. My first career was as

campaign to celebrate the agency’s 50th

a journalist. In more than a decade as a

anniversary that reached more than one

newspaper reporter, I interviewed principals

million people on social media.

and teachers, worked as a correspondent in Iraq and Haiti, and wrote hundreds of local news stories. While I loved journalism, I was

Being the chief communications officer of an

always an observer describing things that

organization requires interacting with

other people did. When my first son was born,

everyone from the senior leadership team to

it changed me in a way I didn’t expect. I found

the interns. With their input, I created and

myself for the first time wanting to take a more

represented the organization’s brand and the

active role in solving society’s problems and

message: Who are we? What do we stand for?

making things better for him and others.

How can we express that on our website, in printed materials, through social media and in personal and public meetings? Because I had

6

Reporters are supposed to remain neutral as

such a long and successful career as a

they encounter multiple people and situations

journalist, I had to work to get people to see

and as a result, you end up knowing a little

me as a communications executive. They’re

about a lot. When I knew I wanted to leave

not the same thing. I interview former

journalism, at first I wasn’t sure which topic

journalists about the nuances of making that

area I wanted to pursue. As I sat undecided,

career transition on my podcast to inspire

a friend asked me: “What would you do for

other journalists who want to create a "life

free?”

after journo."

C - SUITE PICS® MAGAZINE - INSIDE THE OFFICE

A Division of Eyemagination Imaging

C - SUITE PICS® MAGAZINE - INSIDE THE OFFICE

7

As a communications executive, I had

The natural process of pregnancy brings

the opportunity to interact with many

enormous change to a woman’s body, and that

organizations doing amazing work that had

lack of control over your body can be

very little communications know-how. Just

especially difficult when you’ve survived a

doing the work is never enough - you have to

sexual trauma. You have to get lots of exams

be able to describe who you are and what you

and you’re being poked and prodded in a very

do in a way that engages people and enrolls

personal space. I purposely chose a midwife

them so they can support you. Seeing the

practice for all three of my children because it

communications-savvy organizations getting

was non-invasive and incredibly supportive.

the funding or recognition, while other just-as-

Instead of doing an internal exam at every visit,

worthy but inexperienced organizations

they would use a tape measure on your belly to

struggle, or in some cases cease to exist, that’s

measure how much the baby had grown. In

what made us start GraySide Media Group, to

honor of all women, no matter what they have

level the field. I love using my years of

been through, I would want to be a doula to be

journalism and strategic branding in service to

an extra source of support at such a liminal

others. Our clients may come to us as

time. The only reason why I would be a doula

unknown, undiscovered, and underrated, and

instead of a midwife is because I am not into

they leave with a clear brand identity and

science or medicine and I would not want to

stronger connection to their desired audiences

actually have to deliver a baby!

that advances their mission and supports their goals.

7.

If you had it all to do over again, would you do anything differently?

6.

If you weren’t doing this work, what

I would have been more dedicated to myself

would life look like?

and my hobbies and interests, like playing

I would probably work alongside a midwife as a birth doula, a non-medical support person trained to assist women during childbirth.

Being pregnant and giving birth is such an intimate, vulnerable and powerful experience in a woman’s life. I’m a #metoo survivor of a child assault, and that trauma can complicate having children.

8

C - SUITE PICS® MAGAZINE - INSIDE THE OFFICE

guitar, sewing and making soap. As the daughter of immigrants, I’ve been conditioned to focus on work and achievement. I wish I had struck more of a balance earlier, because just imagine how many bars of soap I would have made, how many dresses I would have stitched and how many songs I could play by now on my guitar! At least I’m aware now, though, and changing the pattern.

A Division of Eyemagination Imaging

8. Something that has always stuck with me is, “You don’t have to make the mistake to learn from it.” What is the toughest lesson you’ve learned, that you hope another woman can learn from you?

It’s an ongoing lesson, to acknowledge my emotions. I’ve taken the Myer-Briggs test and I’m a Thinker. That means that my default nature in any situation is to tap into my thoughts rather than my feelings. I love that I am practical and rational, and my sense of humor comes from that perspective! Not everything can be solved with a screwdriver - sometimes you need other tools.

That’s what I’ve learned, especially from my husband and business partner (who is a Feeler) that my emotions can be a signal to my values. If I’m angry or happy about something, it’s a way for me to be in touch with what’s most important to me.

9. Reflect on your first major challenge in a leadership role. What resources did you have, or need and not have, to overcome it?

I was encouraged by a boss to fire several team members. I was promised support in hiring new people, but I was still so scared to do it. Instead, I made a compelling argument for keeping them on and my boss relented. That was a mistake

C - SUITE PICS® MAGAZINE - INSIDE THE OFIFCE

9

because I was a new manager and at that

11. Top businesses have a board of

point my boss had more experience with my

directors to help govern the business

staff. I should have trusted my boss. And I

effectively. Who is on your personal

should have had faith in myself that I would

board of directors?

have worked it out.

My husband, who can see all my blind spots. My

10. There is a lot of research

7-year-old son who keeps me on my toes. He

demonstrating the value of

will ask me: “Mommy, when are you putting out

diversity in leadership. Tell me

your next podcast episode?” My oldest friend

about your experience as a female leader in your industry. What has diversity looked like in your work?

who dates back to high school and knows me so well; I love that even though we are not in each other’s lives everyday, we can always pick up where we left off. These are some members of my personal board. What I love is that they don’t

Often I am the diversity! There are still too

care that I went to Princeton or obsess about

few women of color entrepreneurs or in the

the cute shoes I’m wearing, or how I look in my

top leadership of journalism newsrooms, or

skinny jeans. They can see right through any

in C-Suite of communications and

facades and the superficial and they care about

advertising firms. The numbers are growing

what’s going with me on the inside.

for sure. And I love that social media has made us more visible to each other than ever, so that you don’t have to feel so alone.

12. What keeps you up at night?

I’m used to walking into a room to greet a new client or serving on a leadership team

Finally, nothing! Between being pregnant,

and being the only person who is like me. It’s

having my daughter -- my third and last child

interesting now working with my husband

-- and nursing her for more than a year, I haven’t

on our business, because it’s two of us and

slept well since early 2016. Now she sleeps

we’re both people of color. Maybe we’ve

through the night, and so do I.

gotten business because of it, maybe not.

You can’t dwell on those things, and we don’t. We know we passionate and committed, and our diversity of experience

13. What do you do for you that brings you absolute joy or peace?

and background is an advantage we bring to our work and our clients.

I drink a cup of hot tea every morning. There is just something about inhaling the steam as

10

C - SUITE PICS® MAGAZINE - INSIDE THE OFFICE

A Division of Eyemagination Imaging

C - SUITE PICS® MAGAZINE - INSIDE THE OFFICE

11

12

C - SUITE PICS® MAGAZINE - INSIDE THE OFFICE

A Division of Eyemagination Imaging

I wait for it to cool down, taking small sips,

16. When do you feel the most confident?

feeling the heat travel down my throat and into my body. It’s a sacred ritual and I can’t start my day without it.

After I’ve put on some lipstick. I don’t wear it everyday but whenever I’m finished putting it on, I can’t help but smile at myself in the mirror and feel

14. What is your favorite book (any

like I’m going to go out and kick some butt.

genre)? What book are you reading right now?

17. If you had to describe yourself in five words, what would they be?

An Hour Before Daylight: Memories of a Rural Boyhood by President Jimmy Carter.

I’m a city girl, born and raised in Brooklyn,

Strong-willed, genuine, funny, practical, and attentive

NY and I absolutely adored this book about Carter’s memories of growing up on a farm and walking to school barefoot. It is a

18. What would you like your epitaph to be?

beautiful ode to a simpler way of life that largely doesn’t exist anymore. Right now I’m

She made things better.

almost done reading Haiti Noir, a collection of short stories from Haitian writers edited

by Edwidge Danticat. The stories are so gorgeously written and so dark at the same

19. If your life were a movie, what would be your theme song?

time. Every tale seems to end in death -- or a presumed death. At first this struck me as

Gretchen Wilson’s Redneck Woman. It’s a country

depressing. Then I realized that it was simply

song where she calls herself that because she sings

good literature because it was true to life.

about preferring to drink beer over champagne,

Doesn’t all life end in death?

buying her lingerie at Walmart instead of Victoria’s Secret (for half price) and proudly keeping on her Christmas lights on all year long. It’s hilarious. I

15. What’s a skill you want to learn?

Why?

sing that song at the top of my lungs. I know that’s not what’s expected from a Haitian sistergirl like me from Brooklyn, but that’s what I love about

To play guitar. I love to sing and I would be

the song. It’s all about defying expectations, and

able to sing a lot more songs if I could play along to them.

C - SUITE PICS® MAGAZINE - INSIDE THE OFIFCE

13

HOW CAN READERS CONNECT WITH YOU?



@THEOLITA10 @LIFEAFTERJOURNO

 THEOLA DEBOSE  LIFEAFTERJOURNO  @LIFEAFTERJOURNO Listen to The Gray Side podcast: soundcloud.com/lifeafterjourno

Follow the business, GraySide Media Group, @graysidemedia, on Twitter, Instagram and Facebook

14

C - SUITE PICS® MAGAZINE - INSIDE THE OFFICE

A Division of Eyemagination Imaging

reclaiming the worst stereotypes about yourself so they are a strength, not a weakness. As women, and as women of color, there are a lot of expectations about us like how we should style our hair, how we should behave professionally, what our bodies should look like. “Some people look down on me/but I don’t give a rip,” the song goes. Sing it, Gretchen!

20. Is there anything else you wish I’d asked you?

How did it feel getting your picture taken? It felt awesome!

C - SUITE PICS® MAGAZINE - INSIDE THE OFIFCE

15

Follow us on Social Media @csuitepics    