The Choice is Yours. (2024)

Eleven years ago, I was in the middle of making the biggest decision of my life.

I had just ended a long-term relationship, and my love affair with New York City was on the skids. The vibrant, eclectic and energetic city that invigorated me in my youth now irritated me as I rode the cramped subway each morning, suffered horribly from bronchitis each winter, and paid hefty rent for my 550 sq ft walk up each month. It was time to leave.

Coincidentally, at this time, I had a great reason to travel outside of town, repeatedly. My friend was heavily pregnant with twins, and I, as the godmother, was flush with vacation time. I could travel to Tampa to catch up on girl time before the kids were born, and I could finally take a much-needed respite from the concrete jungle.

As I flew low over the Gandy Bridge, I fell in love.

The climate. The pace. The proximity to the beach. It all reminded me of my humble beginnings in the Caribbean, so I was immediately sold.

I needed to move, stat.

Mentally, I started to plan my relocation down south, but my thoughts were immediately halted as I envisioned telling my boss. How was I going to break the news to her?

Honestly, we were thick as thieves. As an early riser, many times when I entered the building first thing in the morning, she was already there, working away, bathed in bright sunshine from the bay windows that lined our office.

As I entered the room, the smell of lavender greeted my nostrils, its fragrance muddled with the smell of fresh coffee from the steaming mug she placed on my desk. Next to that was a toasted bagel, topped with an organic egg (yes, we had facilities and yes it was ALWAYS organic) and after I settled in, we would officially start our day at the round conference table to brainstorm and solution-out action items for the meetings scheduled that morning.

During my time working with her, as our rapport, relationship and friendship grew, her trust in me grew. I did not have an extensive resume when she hired me, but I had some skills, and I was smart. She saw this, gave me her blessing, and sent me off. And I ran with it.

She encouraged me to work on drafting formal deliverables for our school, because she knew I loved to write. She sat me next to her in meetings with senior leaders. I reviewed resumes and made notes for her scheduled staff interviews and sat in on hiring panels. She exposed me to the inner workings of management, delegated the leadership of support staff to me and provided me with the space I needed to grow and develop as manager. I was being developed for a role way above my station. My boss saw my potential.

When I finally told her I was relocating, she encouraged me to go and has continued to support my growth since then. Never once did she try to squelch my growth. She fostered it. She was the Inspirational boss.

Watching her work inspired me to do my best, because she did her best. Her passion for youth was evident in her actions and in her eloquence. When she spoke, everyone listened. I listened. And I learned. I am capable because of what I absorbed under her tutelage.

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Fast forward a few months.

A headhunter reached out to me about a role in Tampa Bay working for the President/CEO of a healthcare company who was looking for an assistant. The recruiter sent me an extensive job description, information about the company, and what looked like a dossier on the senior leader for my review before our screening call. I took to the internet to search for any information I could find about my future boss. The following week, I was on a flight to Tampa to interview for the role.

After several consecutive interviews, it was finally time to meet him. He was a diminutive man, soft spoken with piercing eyes, who never broke eye contact as we chatted. Our conversation was short and to the point. He explained in detail what he expected from me and asked if I could meet those expectations. Of course I could. I was hired on the spot.

For many reasons outside of our control, this position was short-lived, but the lessons learned during this role have stuck with me to this day. During my brief tenure, the scope of my work and leadership latitude exponentially grew. I was given the blessing to interface with leaders in government, and at the local, state and federal level.

I met with political fundraisers and angel investors in our local area. I liaised with high profile politicians who contacted our office from across the country, power attorneys, bankers and the most competent in health care risk and compliance. I supported their work, responded to their emails and ensured they had everything they needed from our company to drive the business forward and to serve our customers.

Never once did he doubt or question my abilities. Did he call out my mistakes and missteps? All the time. BUT he made them teachable moments.

As a young, black female getting my feet wet in a new and fast-paced corporate environment, I understood how he empowered me in my role to be my best. He ensured I had what I needed to do my job, well. His way did not work with everyone, as he was direct, candid, spoke directly to the issue and was at times low and patience and time. But when I slipped up, with each correction, a commendation was equally doled out to soften the blow. He gave me sugar with the vinegar. His words and his way toughened my skin and prepared me for the world outside of his glass-paned office.

On some days at the end of the day when the staff had left and we were left planning for the next day, we would veer off topic and chat about his family, an article in the paper, his favorite restaurants or what I was going to do for the weekend.

He was an Intellectual boss. Working for him was like a boot camp. Lessons in business, finance, legal, operations and strategy were all covered. He gave me a front row seat to learn from him and his executive leadership team.

Sometimes the shortest experiences can be the most impactful.

And then a few years later, an awesome opportunity practically fell in my lap. I had the opportunity to possibly work with and support another female executive. I could not turn this down. She was coming to town and would only have a brief moment to connect, talk shop and see if we clicked.

On the afternoon of the interview, I had to leave from another meeting across town to connect with her at her work site, and as luck would have it, there was a pile up on the interstate. I could see the clock ticking and my time rapidly running out. I was going to be late. VERY late. To add to the frustration, the building where we were to meet had an obscure address that GPS did not like, so I spent an extra fifteen minutes circling the block trying to find the entrance.

Finally, sweaty and exasperated, I parked my car, jumped out in my pants suit and heels and booked it to the door. I took the stairs, raced down the hall and found her office.

I was twenty-five minutes late. I knocked and entered, apologized profusely, and introduced myself, wholeheartedly expecting to be told to take a hike. She looked up from the desk, glasses perched on her nose, told me where the restroom was, to get some water, and said she would be finished in just a couple minutes. That evening we spoke until the janitor told us to leave the building.

While working with her, I would maximize opportunities to connect because I supported her team virtually. We scheduled regular calls just to check in, and when she was in town on business we would meet up for lunch to chat. These connections improved my ability to anticipate her needs, to help scope out solutions to issues impacting the business, developed my capabilities in project management and allowed implement administrative efficiencies to ensure that she was best prepared to lead our region.

She was a Respectful boss. She recognized I had a lot on my plate, so she kept me in the loop and gave me the context and details I needed to act with conviction and independence, in her absence. She communicated effectively, did not micro-manage, listened and provided real-time feedback. She was/is successful because she never lost her cool, treated others, regardless of title, how she wanted to be treated, was honest, fair and worked hard.

By now I am sure you are starting to see a trend.

I have been lucky to work with great people and have learned a lot from all of them. The one thing I can recall about each of the initial meetings with these individuals was that none of these interactions felt like an interrogation- they were all conversations.

I was not subjected to a battery of rapid-fire questions, and they did what they could to put me at ease in the moment, to ensure I could use the brief time during our interview to gain as much knowledge about who they were, how they worked and what they would need from me.

After I was onboarded, I did not have to fight for time on their calendar, fight for context, fight for their confidence or fight for adequate compensation. They prioritized time with me, gave me what I needed to be successful and did their best to create an environment that was inclusive, safe, and primed for me to deliver my best work.

So, as many of you all are currently looking for a new position, and IF you are wondering what you should look for in your next leader, here are some tips to help you in your decision making.

1. As you spend most of your time at work, you should at a minimum, respect this person AND your values should align with theirs. Extra points if you really like them. Call yourself lucky if you can envision yourself being mentored by them.

Next,

2. Does your working style align with their management style? How can you tell? Ask them! This is what interviews are for. Use this time to find out if their way of managing is going to agree with how YOU work, long term. If it won’t, then don’t! No amount of money, ping pong tables, or free snacks are going to make a misaligned relationship, business or personal, work.

Additionally,

3. Are you ready to be managed? Sometimes we start a position with a great leader, but we are not in a teachable place. This is where insight comes in. Know where you are in your professional journey and be honest with yourself about what kind of guidance you are ready to accept.

Remember, all seeds have the potential to develop. They can be planted in good soil, watered every day, provided with direct sunlight, food, and nurtured.

However, if the seed is immature, it will not grow fruit.

In my own career I strive to evidence the values I learned from these leaders: to seek inspiration, to grow my intellect by learning and doing, and to be respectful. I continue to seek out guidance from my more experienced colleagues, openly seek mentoring and coaching, and actively utilize these opportunities to learn and to be better.

One day, I hope someone will write one of these articles about me.

As cheesy as it may sound, I would want them to say that I too, gave them a chance, that I listened to their ideas, that I gave them great feedback, that I trusted them with great responsibilities, and that I pushed them out of their comfort zone.

I was provided with great experiences beyond what my mind could envision, and I excelled.

Simply because I was given a chance.

What’s up this week??

• I’m reading: Mastery by Robert Greene (still working on this one….)

• I’m presenting here! Neurodiversity in Cybersecurity Summit 2024 | SANS Institute Register today.

• I’m listening to this series - NAE Website - NAE Launches Diversity Dialogues Podcast with Wanda Sigur

• I’m watching: How To Become A Cloud Architect And Get Your First Cloud Architect Job - YouTube

• I’m doing: Life has been stressful lately - The Self-Care Wheel: Wellness Worksheets, Activities & PDF

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