“Are you afraid?Good. You’re in the great game now. And the great game is terrifying.”-Tyrion Lannister, Game of Thrones

In 2016, I was promoted into the first sales leadership role I’ve ever had in my career. There were maybe a handful of us promoted into sales leadership and I was the only person of color in the role. Furthermore, all of my bosses were white males.

I felt accomplished. And proud of myself. I also felt alone.

What I didn’t know about myself back then is that I immediately avoid unpleasant feelings by shifting into what’s positive about a situation. Unconsciously, I resisted feelings of aloneness by creating joyful experiences for my team. I’d make jokes during meetings. I’d try to make people laugh. I’d shy away from hard conversations by magnifying small things into HUGE wins.

The reality was I didn’t feel like I belonged. I felt unsupported. I felt like people were just waiting for me to fail since I was the only person of color that was a sales leader.

What got you here, won’t get you there

When I coach new leaders, especially execs, I always offer this distinction that the mindsets and behaviors that got them into their current level of success won’t get them to their next level of success. I know this because I fell into this trap too.

My mindset about leadership at that point was to please. If I please you, I am leading you.

Our mindsets are embedded so deep into our programming, we’re not aware that they’re no longer serving us. Even worse, we don’t notice that they’re no longer serving our people and our purpose in the world.

In 2016, I did a disservice to everyone around me by learning to please them. If they liked me, that means I’m doing a good job. For my direct reports, it meant withholding significant feedback that might hurt their feelings. For the senior management, pleasing them meant not telling them my lived experience as the only person of color on the sales leadership team.

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Do you ever have moments in your life where you wish you could travel back so you could do better?

This is one of those moments for me. I’d go back to 2016 with a different mindset. I’d go back with a new distinction about leadership.

The new distinction would be that true leadership is about serving, not pleasing.

If I’d had the service leadership mindset, then I would not have withheld important feedback from my team. I would have been more transparent with them. I would have asked for their help. The way I would have served them is through vulnerability. I’d go back to Day 1 and I’d say,

“Look, I’m nervous. This is my first go at this thing and I’m afraid to do the wrong thing. I’m afraid I’ll look foolish. I need your help. These are our goals and I need you to tell me what you need from me, how you want me to serve you, how you want me to lead you, so you feel positioned to meet these goals with us.”

If I had this service mindset, I’d immediately tell one of my direct reports that I was offended by their behavior. That I care about them and developing a good relationship with them. And in order to do that, it meant highlighting a behavior that impacted me in a way they might not have been aware of. Instead, I ignored it. I let it be. And then I ended up being passive aggressive with them in front of the group during a meeting.

If I had a service mindset, I would have pushed back against the HR team who was calling me daily asking me about my management process. It felt like they were looking for holes, instead of actually training me. Instead of just going along with their questions and playing nice, I would’ve asked them if they were doing this to other managers too, or just me. It would have been an opportunity to speak truth to a system unaware of invisible behaviors it was subtlety reinforcing.

But I didn’t want to rock the boat. It would mean I wasn’t pleasing others. It would mean I would be disliked. And because I was more concerned about myself and the perception I wanted others to have of me, I did a disservice to the system.

That was one of the hardest times of my life. I was so mad, mostly at myself, for not seeing it sooner.

But I also hold compassion for myself. I often tell my clients that if they had known better, they would have done better.

I take that advice too and hold compassion for myself. For my heart. I didn’t know better. And if I had, I would have done better. For me, my path meant learning the distinction between pleasing and serving by going through that experience. And I’m so glad I did.

What about you? What mindsets got you here? How can these same mindsets prevent you from getting “there”?

There is a depth to this journey. It’s challenging, frustrating and tender. So if you reflect on these questions, be gracious to yourself if what you initially find is unnerving. Seek support.

But if you’re going to take on the burden of leadership, the truth is we need you to take on new mindsets. This is how you can serve us. This is how you can generate the most impact in the arenas you’re playing in. This is how you change lives.

Step into your great game. Follow the fear. Speak to it. Listen to its wisdom. The fear is trying to stop you from taking action. Listen to what action it’s preventing you from taking. And take that action. I promise you, there is a greater freedom on the other side.

Fiercely loving you,

Jomar

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