Startup leadership lessons from Barack Obama

Why should anyone be led by you?

This is a great rhetorical question for any startup leader, focusing on your leadership values, purpose and approach, and self-reflection enquiry. It’s also the title of a book by Rob Goffee and Gareth Jones, research I use when working with startup founders to help shape and articulate their leadership style.

Goffee and Jones identify some key concepts – know and show yourself often, get close to your people but also keep your distance, and communicate with care. The key is to release one’s inner self and to talk and act in an emotionally connected way. Startups need emotionally intelligent, authentic leaders, with relationships founded on trust.

Contrast this to the current political leadership in the UK and US. Trump in a parody president, I simply can’t take him serious on anything, he lacks any ounce of credibility or gravitas. It’s the same here with Johnson. On Johnson’s desk stands a bust of the Athenian leader Pericles – his ‘hero and inspiration’. Pericles built the Parthenon. Not sure what Johnson has built, he’s deconstructed most things he’s touched.

But the differences between Johnson and Pericles are not trivial. It is not simply that Pericles had more self-control, allowing him to act more prudently. It was Pericles’ understanding of when to speak and when to be silent, when to lead and when to step out of the way. He was rooted in a notion of personal honour, and the honour of the state.

In contrast, Johnson operates in a dislocated dance, like a frantic startup leader who acts and speaks seemingly in the moment, lacking a coherent strategy, focused more on the apparent celebrity status of being a startup founder than being a leader. I see many of these, alas, and like Johnson, they want to grab the tail of the galloping horse of history, when everyone else is still wondering where it might be stabled. Johnson is whistling the horse of history to himself, and whipping it on its way. Trump is no different.

Against this backdrop, how I miss Barack Obama. His presidency appears to be a lost golden age when reason and morality reigned. All of his faults, real as they were, fade into insignificance compared with the crippling defects of his successor. His redeeming qualities are more readily apparent, as we live through a deadly pandemic with US and UK leaders who embody the antithesis of Obama’s empathy and rationality.

Obama’s strengths – seriousness, dignity, intellect, probity, dedication to ideals larger than self – shine all the more clearly in retrospect. With Obama there was no self-praise and no name-calling. In his speeches, his sentences were complete and sonorous, and probably written by the speaker himself. Imagine Trump writing anything longer than a tweet – and even those are full of mistakes – and like Johnson, his speeches are bombastic but hollow in substance.

Imagine Obama as a startup leader. He epitomised Mandela’s example of persistence and of hope, positivity with realism and focus. I’m nostalgic for the ballast of his familiar cadence and the Yes We Can ambition of his presidential agenda, just what you want from a startup leader.

So for this blog, I’ve boiled down my thinking to look at the parallels from the best traits of Obama’s political leadership, and take these into startup leadership, using Obama’s own words to illustrate why anyone should be led by you, from a startup perspective.

1.        Be a visionary

Focusing your life solely on making a buck shows a certain poverty of ambition. It asks too little of yourself. Because it’s only when you hitch your wagon to something larger than yourself that you realise your true potential.

You must stand for something and communicate your vision to the people you want to follow you.

  • Learn to paint a picture with words, speak it, write it, touch it
  • Your startup vision should be in your mind every day, and you should re-evaluate it occasionally so that it stays fresh
  • Be involved in living and breathing the vision every day

2.        Have passion

Take off your slippers, put on your marching shows. Shake it off, stop complainin’, stop grumblin’, stop cryin’. We are going to press on. We have work to do.

Your startup team want passion, in fact, they’ll go to the ends of earth because of it – think of the sailors who travelled with Columbus to explore uncharted territory. Their leaders’ passion inspired them to take on new and dangerous challenges. Engage and represent your people to light the fire in their bellies, to get them to feel passion about your startup venture, and connect to your vision. Passion is infectious.

3.        Be a great decision maker

If you run you stand a chance of losing, but if you don’t run you’ve already lost.

How do you make major decisions in your startup, what is your process for making them? Some leaders have a set process, and others trust their intuition and go fast. But you don’t want to be one of those leaders who consults no one before making a decision, announces the change the next day and then gets frustrated when no one follows it. Leadership means having the courage to take timely corrective action on someone or something that’s not working. Timely decision-making is intrinsic to good leadership, read the signals above the noise.

4.        Be a team builder

Where we are met with cynicism and doubts and those who tell us that we can’t, we will respond with that timeless creed that sums up the spirit of a people: Yes We Can.

To become a great startup leader, you must develop a great team. Don’t breathe down their necks and don’t micromanage, enable your team to find their voice, give them the freedom to work through their own decisions. However, when projects aren’t on track or you are falling behind a deadline, it serves no one if you start pointing fingers. This is when you need to support and inspire confidence. When red flags are showing, be a tower of strength and leadership.

5.        Show your character – sense and respond

Keep exploring. Keep dreaming. Keep asking why. Don’t settle for what you already know. Never stop believing in the power of your ideas, your imagination, your hard work to change the world. If you’re walking down the right path and you’re willing to keep walking, eventually you’ll make progress.

Without character, all the other traits are for naught, because your innate character strengths play a critical role in your leadership style. The real question is, are you aware of just what role they play? Take time to learn about your individual personality and what part your character plays in your leadership style.

6.        Lead collaboratively

The cynics will be the loudest voices. But I promise you they will accomplish the least.

Collaboration means working together, with give and take toward a common goal. Don’t egos get in the way, if people rather than ideas take centre stage in distorted ways your startup is in trouble. Leaders collaborate through rigorous debate of ideas, not by demonising people.

In describing China’s transition toward a socialist market economy, former Chinese Communist Party leader Deng Xiaoping used an evocative image of discovering, rather than planning and solidifying everything before starting: We are crossing the river by feeling for stones. This is a lovely analogy of thinking about progress, so maybe take a step back and refocus more on creativity and innovation than simply ‘getting stuff done’.

7.        Be balanced for the ups and downs, maintain perspective

Progress comes in fits and starts. It’s not always a straight line. It’s not always a smooth path.

A startup leader must own the ups and the downs – the errors and failures shape you more, even though first thoughts tempt you to distance yourself from them. Aside from being good moral leadership, an error-owning leader tends to result in great achievements in the long run due to their determination to bounce back. Alas most political leaders are epically far better at blaming or stepping back from mistakes than they are at owning a failure or misstep.

In a startup there is a high degree of flux at any moment in time. There is no paradigm, no precedent, there is nothing. You have to carve it with a sensitive hands-on connection, with the particular reality in front of you. Don’t lead the metaphorical charge, lead the thinking.

8.        Think of your work as a craft, not an assembly line

We need to steer clear of this poverty of ambition, where people want to drive fancy cars and wear nice clothes and live in nice apartments but don’t want to work hard to accomplish these things. Everyone should try to realise their full potential.

Leadership means candour with yourself and others, both emotionally and intellectually, being willing to ask for and hear honesty from others. Honesty brings the humility needed for leaders when things are going well, and the necessary fuel for critical change when things are in trouble.

9.        Listen – lead with empathy, not argument

We live in a time where there is a big contest of ideas. We see the world as there is us and there is them. Societies work better when everybody has a voice.

Leadership means asking and listening, rather than doing the talking all the time. Sometimes your job is to quieten the noise of your own point of view in order to hear others. The next time you’re in the midst of a maelstrom, choose to take responsibility as the leader and own the problem, but reach out with open mindedness to your folks, work through a team based solution by listening, then get to work and sort it.

10.      Find the areas that unite

You’re not going to solve a problem like climate change on your own. I was the President of the United States, I had some clout, some juice, and I cared about this issue deeply. But I couldn’t solve it alone.

According to Obama, what is really powerful is when a group of people with different perspectives and different backgrounds are brought together. Because we all have blind spots. We did not come to fear the future. We came here to shape it. We don’t turn back. We leave no one behind. We pull each other up.

Startup leadership is the art and science of influencing others, a leader is a dealer in hope, keeping your own head above water in the midst of an on-going fire-alarm. But no matter what tumult is thrown into your path, your response as a leader is to take responsibility. It can feel like the whole world rests on your shoulders, but fixing the problem and wrestling it to the ground, owning and addressing the issue, is the primary role of a leader in a crisis.

Being a startup leader can be harrowing. Managing competing priorities is an uphill battle, mustering the courage to keep going gruelling. You need to be both tough-minded and tender-hearted with people, looking outward and take responsibility, leaning into tough situations. Obama gave confidence in giving direction, simultaneously offered meaning and purpose to people. He led with empathy – in a startup it’s important to ‘feel the pulse’, being in touch with everyone to have a sense for the hidden and silent things.

Transformational presidents like Lincoln, Roosevelt and Obama challenge and change the direction of the country. They indict the old order and summon a new vision, carry the people forward and create opportunity to put the country on a new path. Obama was awarded the Nobel Peace Prize during his first year in office, compare his stature to the tawdry leadership we have from Trump and Johnson, highlighting how much we miss his eloquence, decency, and steadiness.

As the above quotes show, Obama remains a symbol of strong leadership, highly relevant for startups. He has many policy legacies, but one legacy that might just outlive every single act of legislation in the history books is the sense of positivity he engendered, and that’s perhaps the primary quality for a startup leader too.

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