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  • Saasy Sistah

Leader of Leaders

I had the privilege of hearing former President Barack Obama speak to Marc Benioff during Dreamforce 2019. I didn’t think I would hear anything that I hadn’t heard before, I like many people admire Mr. Obama’s eloquence and charisma. I thought the conversation would be centered around technology… ya know since it was a tech conference. I was pleasantly surprised that the conversation was focused more on social impact. 

So I wanted to talk about how this one session summed up what I got out of 2019 and how I will apply those learnings for 2020 and beyond. Have you ever thought about what leadership means to you? Well, Merriam-Webster defines leadership as the office or position of a leader. This is an extremely basic definition, however, Mr. Obama spoke extensively about this very topic. One thing Mr. Obama said to Mr. Benioff is that “you need to have people who are smarter than you sitting around the table. Find those ‘Leaders of Leaders’ and amplify them, uplift them and include them.” 

As I look back on 2019 and prepare myself for 2020 I ask myself am I “leading” the change I hope to see? 

I like to *think* that I am. I try and focus on the importance of the individual and the importance of the community that raised them. I think about the platforms that I not only create but support, are they allowing these people; these communities to thrive and succeed?

Being a “leader of leaders” is action leadership and part of action is living in such a consistent moment in the present you’re not thinking about what you’re leaving behind. However, you’re acknowledging the impact that’s being made with every exchange and interaction. 

We are trying to shift narratives so a leader of leaders will focus on impact over legacy. The work that I am doing is not the beginning and it will not be the end. I know that I am continuing to work towards a future that I am not guaranteed, however, I deem it necessary and essential. There were many great leaders that came before me and I consistently question how do I continue in the legacy and impact that was presented to me? 


One thing that I know to be true is that you have to make accommodations to the existing structure even though you want to change it. Working within the existing structure is the only way to move forward. The world that we live in that we want to change is not binary. Binary thinking reduces it to “good” or “bad” with nothing in between. There is more grey area than any of us care to admit. We know that at times binary thinking is vital for decisiveness however, it can be harmful when not used appropriately. That’s why it is imperative that we, while making these accommodations, ask ourselves – are we contributing more or less to the things we want to change? Are we part of the solution or part of the problem? 

The world is messy and there are ambiguities; we need to get over the fact that nothing or no one is 100% pure. I have to remind myself that the impact I leave behind the youth will carry on until we are able to reach total equality and equity.


  1. Evaluating what I believe 

  2. Testing it against the world 

  3. Developing skills, courage, and resilience 

  4. Fit my actions to the scale of influence I have 

  5. Continually analyze what worked and what didn’t 

When you take these steps you’re ready to take it to the next level. Remember you are trying to expand the orbit of your impact and it’s an iterative process. 

Worry more about what you want to do rather than what you want to be. When you replace ‘I want to be’ with ‘I want to do,’ you organically do this by doing the thing you want to do. You will expand your influence and you end up being a leader, doing the things that you actually care about and a byproduct of your passion will be success. 

Remember to remain purpose-driven: resist, mobilize, and fail – but always find the small victories. I choose to be a “Leader of Leaders” by applying something else that Mr. Obama mentioned. “Be kind and be useful” doing this you will find like-minded people. I have found many beautiful allies and accomplices. Without whom my impact wouldn’t be what it is. I want to thank them for being leaders of a work in progress leader. This post is dedicated to you! 

So how are you changing the world? 


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