Dethra Giles

Chief Bridge Architect, ExecuPrep

1. Did you have a favourite teacher at school? Who was that person and what did they teach you?

Ms. Grisby, 5th grade elementary school. She was the first Black teacher I remember. I loved everything about her. Her hair was almost honey blonde, her skin was pecan brown like mine and she was sassy.  Not “I have an attitude” sassy, but  “I know what I am talking about and you know you like it” sassy. I was a talkative child and prior to Ms. Grisby it always got me in trouble. Teachers would complain to my mother, send notes home, and lower my marks all because I was talkative.  Not Ms. Grisby, she would jokingly tell my mother “that girl can talk. I moved her from her friend and she talks to everyone I sit her next to. I sat her by me and she talks to me. But, it’s cool.” I wish I could find her.

2. At what age did you become an adult? What happened, and how did you know?

I really can’t remember when I “became an adult.” I feel like it just happened. I began making adult minor adult decisions at a very young age.  Those decision progressively increased and had more and more impact on my life long term.

3. What do you think is true that most people think is false? What do you think is false, that most people think is true?

I think most people are good and want to do right we just live in a system that prevent their better nature from thriving.

Nature vs. nurture.  In 2007 I had my 2nd child- a boy. Prior to 2007 I was adamant that the difference between boys and girls was 100% nurture.  In walks my son.  Exposure to him and other little boys via him changed my mind significantly. Now, I still believe that boys and girls are socialized differently but I am no longer a 100 percenter. I feel as if about 70-80% is nurture, the rest is nature but that 20-30% stands for a great deal of difference between the genders.

4. If we were to go and speak to people who don't think very highly of you, what do you think they would say?

I wasn’t ready for what she said. Just because it is the truth does not mean everyone needs to know it or wants the truth. She didn’t have to say that.

5. What’s one misconception people generally have about you?

That I prefer extroversion (am an extrovert). I am an only child (I actually have two brothers and one sister, but I am my mother’s only child and was raised apart from my half siblings) and never wanted siblings. I love people and I really enjoy alone time.

6. In the last few days, what news has given you most cause for alarm? In the last few days, what news has given you most cause for celebration?

They are one in the same: there is both cause for alarm and celebration concerning the unrest in the US around race.  If we don’t get this right it could tear our country apart but if we do we will be a shining light. I am alarmed because the opportunity to get this wrong is ever present and celebrating because there is an equal opportunity to get it right.

7. When was the last time you felt like an outsider in a group? What did you learn from the experience?

I have become comfortable being the outsider, it is my world. The better question is when was the last time I did not feel like an outsider.

8. What’s your desktop/mobile screensaver? Take a screenshot and attach it to your answer!

My two children as young children (4 and 1)


9. Cheese or Chocolate? What kind?

That is like saying right or left arm. I am not picking. But, my chocolate must be dark (70%+) and I love feta and blue cheese.

10. What are the three books that you would unhesitatingly recommend to others? Why?

The Temple of My Familiar by Alice Walker

I love the complexity of the characters in this story, how you have to pay attention and stay connected to the story to prevent missing anything.  I love that it does not wrap up in a pretty little bow where everything just ends perfectly. It is like life, a little messy.


The Alchemist by Paulo Coelho

This story reminds me to search for the right things.

Selling to Vito by Anthony Parinello

This changed my life as a business woman. It cut my conversation to sales time in half.  It allowed me to be laser focused about who I need to speak with to go from conversation to contract.

11. Which fictional villain do you find yourself sympathising with most? Why?

The Joker.

He lives in a world where nuance has made him the villain. He and Batman are the same and society has deemed Batman a hero but the joker a villain. What if society had told Joker, who is equally intelligent, strategic and motivated, that he was good, that Gotham needed him, that his wit and intelligence was genius and not sinister, would Gotham be sending out a Joker signal instead?

I think this resonates with me because I have seen the impact first hand of being given the message about who you are and what your talents mean.  I have a cousin, my favorite cousin who ended up in prison. He was smart but was told he was a smart ass, he was savvy but was told he was slick, he was strategic but was told he was always scheming and was confident and was told he was cocky. So what did he become? Not a Smart, savvy, strategic, confident business man, he became a Smart ass, slick, scheming, cocky drug dealer.  I don’t think adults realize the power their words have over children and The Joker is a clear indication of that to me. Gotham is the adult and Batman and The Joker are the children.

12. If you could invite any 3 people - living or dead - to your final dinner party before the end of the world, who would they be and why?

Yashua (Jesus Christ)

I know that sounds cliché but I really want to know where does want get the strength to love their enemies in such a way that you would lay down your life.  I struggle with people the idea of not harboring ill will for those who lie on me, or speak ill about my work, or even treat me poorly. But, to ask that people in the process of killing you be forgiven and be given the opportunity to live with you for eternity, that blows my mind.  Not only do I want to know where that strength comes from but I also want to know where that desire comes from. Not only do I have trouble finding the strength to do it but I also, often lack the willingness.

Queen Nzinga of the Angola

Talk about a warrior Queen.  She literally made her own seat at the table.  In one interaction when the Portuguese invaders got tired of warring with a people they thought would be easily defeated the Portuguese colonizers invited the Queen to a negotiation for peace. They intentionally had no seat for her at the table. Those of us who practice and teach negotiations recognize this as a power move. But, Queen Nzinga was not hearing it. She had one of her men get on all fours, creating her own seat at the table.  I can only imagine the looks on their faces when she made the superior power move.  I would love to talk to her about how what it was like to live in a society that embraced her totality as equal a society that allowed her to be without explanation.  To live in world where you did not have to compound defending your skin and your gender with everything else you have to fight for. I would love to know what that felt like. To just be and be allowed to be in your country, yes, defend against external invaders but to be able to be home at home, what an ideal.

Walter White

Black man with Blonde hair and blue eyes who could have easily passed for white in a land where white was the thing to be.  Instead of denouncing his true heritage, that of an African American, he embraced it and put his life in peril to expose violent racism in the United States, even going in an infiltrating the KKK to investigate the lynching of Blacks in the US.  Because of his appearance he was able to get information that was only shared amongst whites.  In one instance a few white people even shared with him that a mob was coming to town to kill him.  They had no idea that he was the Black man of which they spoke when they told him that a white mob was on the way to kill a Black man that was passing for white and “was causing trouble.” I would love to ask him “why and how?” I LOVE my Blackness but would I love it so much if I had a choice.  No one will ever mistake me for white, no one will ever afford me the privileges provided to my fellow beings with milky white skin.  I would love to think I would embrace my Blackness even in the face of not having to do so. But, would I, particularly when people around me were being raped, hung, killed, maligned, disgraced… I would want to ask him what it was like to be a Black man trapped in a body that looked white? What was it like in the belly of the beast where he was surrounded by white men plotting to kill people like him? How did he maintain his composure in the midst of people who were his intellectual inferiors while they insisted that this truth was not so?

13. Can you give a work example of a lesson you had to learn the hard way?

A good idea at the wrong time is a bad idea. I was young and new to a very old and drenched in tradition institution. I felt like I could come with my great/grand ideas that “just made sense” and everyone would bow before my intellect. Why wouldn’t they, I was bringing great ideas. Not only did I think these ideas were great, but many of them chimed in and acknowledge the merits of these ideas as well. What could possible go wrong here? I learned that I was moving too quickly with no one on board to support my ideas. They loved the idea but were not ready for it. I did not assess the organizations readiness for the ideas. Because they were not ready they rejected the implementation of the ideas totally. Because the timing was off, the idea was rejected and never implemented.

“A good idea at the wrong time is a bad idea”

14. What's a skill that isn’t on your resume, but your former bosses would recognize as one of the reasons you are successful?

Relationship building. I have historically been in positions where I needed authority that I did not have. That authority was required to get the task done.  No one in my leadership line cared that they gave me responsibility with no authority. The only thing my leadership cared about was task completion.  I had to learn the authority of influence.  Through relationships I was able to get things accomplished: I was able to use authority I did not have to get the job done.

15. Who was the best person you ever hired? Why were they so good?

Ivy Horn.  She had all the skills but came to the job to learn and really dove in and did the work.  She is a great person: honest, professional, eager learner, humble… She is the bar I use to measure anyone I hire even to this day.


16. Have you ever been the weakest member of a team? What was the situation?

Yes, as an entrepreneur I am quite often the weakest member of the team. The weakest member of the team is my comfortable state; it is how I know I am doing my job well as a leader. I don’t desire to be the expert in everything or the strongest person on every aspect of my team. I am intentional about hiring experts and allowing them to thrive and do their job. When I am with the accounting team or IT or operations or…I am the weakest link and that makes me happy. Being the weakest link on a well performing team let’s me know I am a good leader.

17. When it comes to our work and industry: what scares you most?

 It scares me that we do not get the respect and credit for how much we contribute to the success of the organization. This means in critical financial times we get placed on the chopping block too quickly and companies and people suffer.

18. What changes to our industry would you like to see post-Covid19? What changes do you think we will see?

Virtual work. I hope that organizations will assess all of their position to determine the feasibility of making each position a virtual one.

19. Do you have a secret tip, tool or trick that’s contributed to your success?

Be OK not knowing. Everyone wants to know but no one want to learn. If you don’t know and you need to know, make sure you learn. But, if you don’t know and your lack of knowledge doesn’t matter to you, don’t learn it just to look good. Spend time on what you need to know and what matters. I am completely ignorant in some stuff and I am comfortable with that because I don’t feel the need to look smart. The things I know I am a genius, the things I need to know I study, the things I don’t know and don’t need to know, I am OK not knowing. Ex. I don’t know IT. I have learned what I need to know to operate proficiently. Outside of that I will not be fixing any hardware or software. Could I learn it? Absolutely, but what will that accomplish? I may look smart to a few but in actuality I will harm my company. The time I spend learning IT would be better spent fine-tuning my expertise, consulting with a client, writing curriculum, completing a bid…I am comfortable not knowing IT.

“I am ok with not knowing”

20. Name one person who has had an extraordinary impact on your career. What did they do and what did you learn from that person?

My mother. Sounds cliché but life dealt her a pretty bad hand, but it also dealt her a few good cards as well. She never pretended like she had a good hand but also did not focus on the bad hand to the detriment of getting the full value from those good cards. She never lied to me about the role she played in our situation. My father did not play his full role and when I would ask about his failures she NEVER said a bad thing about him. She would simply say “I was not diligent in my selection process. I should have done… I knew better than to… But this is how we are handling it now.” She taught me SO much about responsibility. I took those lessons through life and it has served me better than any other education.

Thank you Dethra Giles for sharing your story with 20 Questions on The Recruiters Tribune. Make sure to also follow Dethra on Instagram because she is killing it over there

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