Lead Like a Poet

3 Leadership Lessons I Learned from Tupac

by Will Small

[5 minute read]


As our world has recently grappled with ongoing issues of racial justice, I found myself returning to the poet who changed my life when I was 14 years old.

Tupac Shakur. AKA 2pac.

You probably know he waxed poetic over beats, given that he’s one of the all-time greats of hip-hop, despite dying tragically young (shot in 1996 at just 25 years old). But, you may be surprised to hear of his lesser known poetic works, scribed on paper the old fashioned way and published in a book called ‘The Rose that Grew from Concrete.’

A friend burnt me a Tupac CD in year 8 – and it stands out as one of the most significant events in my life. A white, middle-class, church kid sitting in his bedroom, listening to an African American rapper speaking about racism, poverty and injustice.

Tupac’s life was nothing like mine. And yet, his poetically woven narrative cut through more than anyone else in my life at the time. My bubble of privilege cracked a little, and I began to realise my experience of the world as safe, fair and comfortable was far from universal.

I became obsessed. A framed picture of ‘pac soon hung above my bed, watching me sleep. He was shirtless, the words ‘Thug Life’ tattooed across his chest (needless to say, my Mum was thrilled, and she never tried to convince me to take it down).

Regardless of how you feel about songs with a language warning or ‘Thug Life’ tattoos, my exposure to Tupac taught me some of the most powerful leadership lessons I know. In a nut-shell, he taught me to lead like a poet, something I’ve tried to do ever since. Let’s shift gears now from my mini memoir into a more standard blog offering: three principles I learned from Tupac, that I think all leaders could benefit from.[i]

1. Well-chosen words transcend divides

Racial. Political. Theological.

Division. Is. Everywhere. Isn’t it?

Social media algorithms (and a good dose of human nature) lead us to build walls and find look-alike, think-alike and sound-alike tribes. But, my most profound experiences of growth and self-awareness generally happen when I am exposed to people and perspectives different from my own. It takes some work though. When we speak the slogans, phrases and lingo of our tribe people disconnect. But, when people use language creatively, and share their story authentically, it cuts through. I’ve seen this a thousand times at spoken word poetry nights, where the same microphone is shared by Christians, atheists, homeless guys, academic gals and other diverse ragamuffins vulnerably engaging in a powerful shared space.

Should you deliver your next message as a spoken word poem? With a few exceptions, I’m going to recommend not. But in your context, what are the words, phrases and lingo that will immediately disconnect you from your audience? Ditch those ones. Listen to people very different to you. Take the extra time to find words that are more personal and thoughtfully crafted. Flex a fresh metaphor. Activate people’s senses with your descriptions. Our words are a super power. They can build walls or knock them down. Which will you choose?

2. Well-crafted messages make every word count.

4 minutes and 29 seconds. The length of Changes, one of Tupac’s most influential songs about racial justice.

What was the length of your last keynote? Sermon? Presentation? I’m not saying it’s wrong to build an argument through a long-form piece of communication. But, can you say what you want to say in less than 5? Can you summarise it one sentence?

I know for a fact that my 3 minute poems are more memorable than my 30 minute monologues.

I’m sure Jesus delivered some lengthy messages. But the versions of his teaching we get in the gospels are punchy. To the point. Easy to remember and relay.

Are you making every word count? Don’t fill the space with unnecessary noise.

3. The personal journals hold the true gold.

Earlier, I mentioned Tupac’s book The Rose that Grew from Concrete. It’s an intimate collection of poems that reveal the inner mind of an enormous public persona. I’m pretty sure he never intended to publish them; someone just found his personal journals after his death and made some coin. I love these poems though because they humanise an icon. They articulate fear, love, grief, hope, faith, doubt and the inner working of a man wrestling with himself and the divine (a description just as easily applied to the Psalms).

So, what’s the leadership point? Keep your journals somewhere obvious so they can be easily published after you die? No. The point is you need a space to process your inner landscape. If you’re reading the Arrow blog, I’m sure you know personal leadership comes first (and is never complete) so this should be a reminder, more than a revelation. (Or maybe that’s what most revelations are?) Your greatest work is done off stage. Without a microphone or platform.

Put a timer on for 5 minutes and spill your brain on paper, without censoring or judging yourself. Write down your biggest doubts, questions, insecurities and fears, your greatest hopes, desires, insights and convictions, and everything in between. The Spirit is with you, as you do so. That is sacred space. And no one ever has to see it, for it to be your best work.

So, to review:

In public, choose language that transcends divides. Keep it sharp and make every word count. Off stage, wrestle it all out. Brutal honesty, no holds barred. God is with you, and isn’t afraid of what is in you.

Words hold incredible weight. So, lead like a poet. And make space to listen to a few along the way. Particularly those who look nothing like you.[ii]


[i] For any fellow hip-hop heads, it was De La Soul who taught me that “Three is the magic number.”)

[ii] If you want to hear a brilliant Tupac song (without any swearing), look up “Unconditional Love.” Reach out to me if you want more recommendations!