Truth stands, even if there be no public support. It is self-sustained.

—Mahatma Gandhi

You likely know about legendary Danish writer Hans Christian Andersen and his 1837 fairy tale, The Emperor's New Clothes—but here is a brief refresher. It describes a king who is duped into buying a very expensive outfit that could only be seen by the smartest of men who were fit for their position. The king paid a large sum of money for the clothes to be made. Upon his final exhibition, he refused to admit that he could not see his clothes because that would reveal he was unqualified to be king. All the men around him also lied and claimed they could also see his magnificent clothing. This charade led to a public procession with the king parading these new garments across his kingdom. It took two innocent children to point out that his “costume” was a sham and the king was naked. Everyone in the kingdom finally came clean. By that time, the swindlers had left the city with bags and bags of money.¹

The moral of the story has a direct application to the corporate world: when a leader surrounds himself with “Yes” men or women, it often leads to embarrassing results. It is far better as a leader to surround yourself with an honest team of people who are unafraid to ask questions or to point out shortcomings as they see them.

I had a personal opportunity to either be a “Yes” man or that little child who declared that the king was naked. My CEO and President once invited me to meet the then-Presidential candidate, Barack Obama, at the Nasdaq headquarters in 2007. I was elated at the invite when it came through my Outlook email. I was going to have this unique opportunity to meet a man who many believed could be the first Black President of the United States. It was humbling to think that my CEO handpicked me out of close to 5,000 employees to be one of the few who would be one of his esteemed guests. I immediately called my parents and told them about the opportunity. My dad was particularly flabbergasted. I also told my small group of close friends. They too were as surprised and encouraged me to get there early and take lots of pictures.

At that time, there was such a fervor for Barack Obama among the Black community. African Americans, Caribbean Americans, and the ever-growing African Diaspora in America all embraced Obama as a force for good. For them, he was a giant symbol of who we could be in this country if we work hard. My parents did not believe that in their lifetime that they would see a Black President in America. Barack Obama now represented that dream.

I recall my mother calling me, shocked and surprised at the news. “Why did he pick you?” “I don't know, Mom!” “What did you do?” She said in an inquisitive and almost accusatory tone. As if to say, please give me some more context so I can understand what is happening to my child.

You see, my mother is different than my dad. For her, good news always came with speculation and concern. In her mind, there had to be a reason why I was picked, and she wondered if the decision had ulterior motives. As a recent immigrant to this country, Mom passed through America in a very different manner than I did. Nothing was given to her. She worked hard for every bit of her success. She also came to America leery of people. There is an instant skepticism of immigrants when they arrive in a new country without knowing the language well. My immigrant parents, especially my mother, formed hardened hearts to this new American world and maintained a more distrusting eye. I felt this suspicion like a dark weighted blanket thrown upon me and any of the achievements that I brought home. My spirits deflated when I discussed with my mom why I was chosen to meet the Presidential candidate. After all, it was a great question: Why did the CEO choose me?

It did not make much sense, as I was only a business development consultant at the time. I had limited exposure to my CEO, and I was not his direct report. In fact, I was several layers below him in the company hierarchy. We hadn't spoken about politics in the past, nor did he know any of my personal feelings about the candidate. Maybe my mother was on to something with her questioning. Frustrated, I quickly ended the call with her. After I hung up, I decided to leave the question unanswered and focus on way more important things … like what I would wear to the event!

The idea of meeting then-candidate Barack Obama gave me butterflies. These are the moments in your life that you can describe to your children and grandchildren! How many people experience exposure to such a historical figure?

I envisioned a closed-door meeting over a large antique wooden conference table with Evian water bottles on marble coasters stationed in front of each seat. I knew there would be other key business leaders from New York in attendance as well. I imagined CEOs of other prominent companies at the table in their dark solid and pinstriped suits. I knew enough to realize that I most likely would not have a seat at the boardroom table. But I figured I would at least be in the room and could take one of the seats in the back. Was my CEO grooming me for a future leadership role? Is that why he wanted me to attend the meeting?

The invite came from my CEO's executive assistant. It stated that I was cordially invited to join my CEO to this meeting at the Nasdaq headquarters in New York. No one else was listed on the email. I could not see who else would be attending.

It was February 2007. At the time, the economy was beginning to falter. Stock prices fell, and Alan Greenspan, then Chair of the Federal Reserve, was publicly predicting a recession. This was also the start of Freddie Mac pulling back from investing in subprime loans, the earliest indication that we were in a volatile housing bubble. By this time, a real estate investment trust specializing in subprime lending, New Century, would file for bankruptcy. American Home Mortgages would follow suit, and by the summer, Bear Stearns would liquidate two of its hedge funds. NetBank would also file for bankruptcy while Countrywide Mortgage was borrowing $11.5 billion from 40 different banks in order to stay open. The American economy was in a free fall.

Candidate Obama was coming to New York and meeting with approximately 150 Wall Street executives at the Nasdaq headquarters to give a speech about how he would reform the financial industry, protect Americans with mortgages, and offer help to middle-class Americans. He was to highlight several financial and tax reforms during his speech, but his message to Wall Street was that more regulations, scrutiny, and oversight were coming their way.

I will never forget that that day, Monday, September 17, 2007. It was impossible to fall asleep the night before. I was so excited about what this grand meeting would be. I tossed and turned the whole night, occasionally staring at the ceiling in the wee hours of the morning.

It was a Monday, so I knew going into the office was going to be hectic, especially because public schools had just reopened. I left extra early and had to take a different subway route, which added to my anxiety. I got off at Times Square where the Nasdaq headquarters were located. Exiting the subway, I remember looking up at all the intimidating skyscrapers surrounding me. As I got closer to the address, I could feel the butterflies in my belly beginning to flutter.

Walking in, I saw scores of reporters lingering around the lobby. As I maneuvered through the crowd, I stumbled upon Jonathan, a fellow employee from my company. What was he doing here?

Jonathan didn't work in our corporate office with me. He worked in our Brooklyn office, where our operational teams were located. Mind you, I worked on the executive floor, the same floor as my CEO, in our corporate office in Manhattan. I assumed my close proximity to the CEO was the reason I made the list. But if Jonathan also made this elite list, who else was invited?

We were directed to go to a specific floor where the meeting would be happening. Security asked for our names and company. As they looked for us on the list, I could not help but notice a long guest list attached to my company. I grabbed my nametag and waited for Edwin.

We rode the elevator to the appropriate floor, entered a big hallway, and bumped into a slew of more co-workers from my job. We all recognized each other and began to walk as a group into the main seating area. It was now five of us inching our way forward. As we approached the front, we quickly learned that only invited guests were allowed in the executive front section with seating. Up there, these executive guests could see the podium and the stage from which Obama would be speaking. This executive section was bordered by a barricade that prevented other guests from entering or exiting. Behind that section was a row of seats for the press and media cameras.

Behind the press was where we were, a rear section where guests of the invited guests were allowed to loiter. Where we stood, there were no seats, and our view of the front was obscured by the media. Two more co-workers joined our group, bringing the total number to seven. None of us had had any idea the others were coming, as we each had received the invites separately. As I gazed at our group of standing employees, all here to see candidate Obama, it hit me like a ton of bricks. Everyone invited was Black.

A sea of thoughts and questions ran through my mind. First, what an awesome opportunity to meet a Presidential candidate who could potentially make history. But did our CEO specifically handpick only his Black employees? While maybe it made sense to bring those employees to see Obama, it forced me to realize how low in the organization he had to go to find enough African Americans like me to invite. There weren't enough of us in the middle or higher levels of management to pull a list of 10.

While we were invited and able to be in the room during the speech, it was impossible to see Barack Obama or even our own CEO, who was seated in the front. On top of that, the other 149 New York business leaders looked a lot less like us. Do you get it? Whites in front, Blacks way behind.

When Obama concluded his speech to great applause, he began to walk through the crowd and shake hands. We all tried to squeeze and push to the front, but by the time we got even slightly close, Obama was already heading to the exits. I remember leaving the Nasdaq headquarters on my own. I tried to see if I could locate my CEO and head back with him, but I lost him in the sea of people. I had dressed up for nothing.

On the subway ride back to my downtown office, I wondered why I had been invited in the first place. I was curious if the invitation was to simply show the candidate that my company had diverse employees. Or did my company want to extend this invitation to our Black employees as a token of appreciation? Either way, I felt small and used as a pawn. Of course, I would have preferred to have been invited on my merits rather than my skin color.

I returned to the office and turned on my computer. There it was, sitting in my inbox. An email from the CEO. He asked for feedback on the event and wondered if I enjoyed myself. I had a quick decision to make. Do I provide authentic feedback or just say: “It was awesome. Thanks for the opportunity”? Should I be a “Yes” man or should I tell the emperor he had no clothes? I decided to let the emperor know he was butt naked.

For some strange compelling reason, I wrote back a long-winded reply:

When I received the invite, I thought I was special. I thought I was handpicked because of my value to the company. I thought the invitation was solely for me. I had worn my best suit, got a haircut, and had excitedly told my parents about this amazing event. However, when I arrived, I realized I was invited with nine other Black colleagues as well. The most depressing aspect of this group was that it included the highest-ranking Black employees we have, including our General Counsel. Even though I was only a consultant at the time, it dawned on me that I made the list as one of the 10 Black employees to attend this prestigious event.

This was not all. We did not get to sit with our CEO who also attended but he was able to watch from an executive section in the front the room. We were forced to watch from the back of the room, way behind the mics and cameras of the media. I assumed I was going to meet candidate Obama. No such luck. He was so far in front of the room with the invited executives that he never made his way to the back. There was too much security for us to try to move forward to meet him. It soon became clear that our company was the only one to bring so many guests. When I realized this, I suddenly felt like a pawn, selected only because of the color of my skin and not because I was a valued employee.

I hit SEND. The damage had been done. This was the feedback I provided to my CEO!

I thought I would be fired or at least demoted. My phone rang. The CEO's executive assistant asked me to come down to his office. That was perhaps my longest walk down any hallway. The walk was the easy part. The hard part was waiting to enter his large and intimidating office: a corner office with its own conference table, giant sofa, and spectacular views overlooking the New York City skyline. I thought to myself how rarely I had ever been in the CEO's office—let alone by myself.

I was also scared that the CEO's response would be to tell me he didn't have to invite me to the event in the first place. Often, when people of color do complain, a common but coded retort is: You should be happy with what you get; it could be a lot worse. This is a silent message expressed through gestures and deeds that we learn as employees of color in corporate America. These statements are never said out loud, but you can definitely feel them.

The CEO called me in. He was as intimidating as his office. A tall White man, he sat down and gazed at me for a moment. Then he began to speak. He shared that this had been something he had been thinking about. I told him how amazing I felt to have been invited but was dismayed to see every other Black employee from our floor there, including our General Counsel. It showed me that our bench was not that deep, particularly if I made the cut as a consultant.

The CEO thanked me for my honesty. He wanted to increase diversity, equity, and inclusion (DE&I) in the company and was strongly committed to it as an executive. He appreciated feedback like this so that the company could do better.

“Can you keep telling me the truth?” he asked.

I smiled and said yes. And I certainly did. From that moment on, our relationship began to grow closer as well. He would email me directly asking for data and information. My confidence grew as I felt more comfortable emailing him back and sharing my true opinion on business matters. He took time out to check in with me and ensure that I felt seen, heard, and supported.

Within a few months, I was promoted to my first managerial role, supervising a team of nine sales associates. I also was quickly recruited to join the company's first diversity and inclusion committee, speaking truth to power without fear of retribution or retaliation.

Then one day, a few years later, the CEO called me into his office and asked me if I would be his Chief of Staff, reporting directly to him. Once again, he appreciated my candor, my insights, and matter-of-factness.

I happily accepted the role and looked forward to the opportunity to work even more closely with my CEO. This role catapulted my career. All because I was crazy enough to send an email telling my truth. It would have been so much easier to lie, but sometimes the easiest decisions are not always the best ones.

I was once told by an executive that my Achilles heel in business was my conscience. In the moment, the true meaning of the comment did not resonate. But today, if that is my biggest weakness, I wear it as a badge of honor. Honesty does not always make you the most popular person in the room. But you will be respected for your values and your resolve. That level of respect is priceless.

LESSON 11.1: BE BRAVE!

Have the courage to fail forward if necessary. Speak your mind, stick to your values, and accept the consequences. Don't be afraid to tell the truth. Ever. When you are asked if you have an opinion, HAVE ONE! When early in my career I was told, “Errol, your Achilles heel in business is that you have a conscience”; what that meant was that I felt a huge burden to tell the truth no matter how hard it was. After years of reflection, I have come to realize that telling the truth is my greatest strength. It can be hard, especially if you do not have a receptive boss. But if you join a team and expect to be a Yes man or woman, you may need to change teams. Do not compromise your morals for your paycheck.

LESSON 11.2: BRAVERY HAS ITS COSTS

Understand the ramifications of speaking up and be prepared to deal with them. I took a chance when I had an honest conversation with my CEO. At the time, I was four levels below him in the company hierarchy. However, I believed my honesty would be welcomed. In that moment, my words could have just as easily negatively impacted my career. Instead of a promotion, I could have been demoted, or just ended up becoming stagnant in my career. I would have had to accept those consequences for speaking up. Pushing back against the establishment comes with risk. High risk can yield high rewards, but it can also lead to your downfall as well. It is important to be pragmatic in your approach. If you are going to be upfront, honest, and bring something to the attention of your organization, be prepared for the possibility that they may not be receptive to what you say.

What is your Plan B? If you are so dependent on the job that you may regret such actions, you should come up with another tactic. Martyrs are not celebrated in the corporate arena. They can become examples of what not to do in many corporate cultures. It takes wisdom and guts to speak up, but you must also possess the courage to accept the consequences. Make sure you decide with your eyes wide open.