Asher's Blog

I have been thinking a lot about what separates leaders who are merely effective from leaders who are truly memorable. Not the ones who hit targets or manage processes well, but the ones who change something in you. The ones whose influence you are still feeling years after you stopped working with them.

Parker Conrad is not someone I have met personally, but his story is one I have followed closely, and it has taught me more about leadership than many books I have read on the subject. In February 2016, Parker was ousted from Zenefits, the company he co-founded and grew to a $4.5 billion valuation in record time. It had become the fastest growing SaaS company of its era. And then, in the space of weeks, it was over. He was forced out under a cloud of controversy, his reputation publicly damaged, and a board member from one of Silicon Valley’s most prestigious venture firms looked him in the eye and told him, “you don’t have another company in you.”

And most people would have simply disappeared.

Six weeks after resigning from Zenefits, Conrad began working on a new company. Not months later. Not after a sabbatical. Six weeks. He went back to his home in San Francisco, sat down with one co-founder, and started building again quietly, with no fanfare, no press release, and no guarantee that anyone would believe in him. That company became Rippling. In May 2025, Rippling secured a $450 million Series G funding round, elevating its valuation to $16.8 billion.

I learnt so much from Parker’s story that I wrote him a thank you note for inspiring this founder (me) – which he replied to. Parker resilience is out of the roof. His story, his boldness, his never-quit attitude, this is leadership 1.0. This is Leadership of the most important kind, the kind you exercise over yourself, before you ever exercise it over anyone else.

And that brings me to the first thing.

1. They Live What They Say

Gandhi said it in a way that has never been improved upon: “Be the change you want to see in the world.”

Great leaders do not point the way. They go the way. They are the first ones to walk into the difficult room, to make the uncomfortable decision, to hold the standard they are asking everyone else to hold. They do not ask for commitment they have not already demonstrated. They do not ask for sacrifice they have not already made.

This is why one of the greatest challenges of leadership is not managing other people. It is managing yourself. Because you cannot lead others to places you have not been willing to go yourself, and people are always watching more closely than you think. Not just your words, but the distance between your words and your actions. That distance, even when small, is where credibility either lives or quietly dies.

Parker Conrad’s entire second act was built on this principle. He did not tell people he could build again. He built. He did not make speeches about resilience. He demonstrated it. Rippling was born out of what Conrad himself described as a revenge fantasy, a consuming desire to prove the people wrong who had written him off. But the method he chose to prove them wrong was not words. It was work. Quiet, consistent, daily work, done mostly in private, for years before the world paid attention again.

That is what walking your talk looks like in real life. It is rarely loud.

2. They Constantly Lift Their People Up

Every leader leaves you with something. Some leave you feeling like you’ve shrunk, like the room, the opportunities, etc., got smaller the moment you walked in. Others leave you believing you’re capable of things you hadn’t dared to imagine before you sat down with them.

The second kind are rare, and they are unforgettable.

John Maxwell, who has spent decades studying leadership, puts it simply: “A leader is one who knows the way, goes the way, and shows the way.” But the leaders who truly change people do something beyond showing the way. They make you believe you are capable of walking it.

Think about the leaders in your own life who have shaped you most. I would be willing to bet that what you remember most is not a strategy they shared or a decision they made. It is the moment they saw something in you that you were not yet able to see in yourself. The moment they gave you more responsibility than felt comfortable. The moment they told someone else about you in a way that shifted how you carried yourself. My life is better because of specific leaders who chose to invest in me rather than use me, and that investment compounds in ways that are almost impossible to fully trace.

The leaders who lift people up understand something deeply: their job is not to be the most capable person in the room. Their job is to make the room more capable because you are in it.

3. They Love the People They Lead

This one is harder to talk about because it sounds soft. But it is actually one of the most demanding things on this list.

There is a version of leadership that loves leading. Loves the authority, the platform, the influence, the visibility. 

And then there is a version of leadership that loves the people being led; that loves them more than it loves the role. Those are two completely different things, and people can feel the difference almost immediately.

When a leader genuinely loves the people they lead, it shows up in small, consistent ways. They remember details about your life. They ask questions because they actually want to know the answers. They make decisions with your growth in mind, not just the organisation’s output. They protect you when it would be easier to expose you. They are contagious in the best possible sense, you want to be around them, and something about being around them makes you want to be better.

Robert Greenleaf, who coined the concept of servant leadership, wrote that “the great leader is first experienced as a servant.” That posture, of leading from a place of genuine care rather than personal ambition, changes everything about how you show up and how people respond to you.

Leadership that is not rooted in love for people eventually becomes transactional. And transactional leadership produces compliance. It never produces commitment beyonds what can be rewarded or seen. 

4. They Are at Their Best When Times Are Worst

If everything is going well and the path ahead is clear, how much do you really need a leader? You need a coordinator, maybe. A planner. But leadership, real leadership, is revealed when things are falling apart.

This is where the truly great ones separate themselves.

Think about Winston Churchill during the Second World War. Britain was being bombed. Cities were burning. The strategic outlook was grim in ways that are difficult to imagine from this distance. And Churchill would walk through the bomb sites himself, in the rubble, among the people who had lost everything, visible and present when it would have been safer and more comfortable to remain at a distance. That act alone communicated something that no speech could fully capture: I am not asking you to face something I am not willing to face with you.

There are three things I have observed in leaders who lead best under pressure.

The first is courage. Not the absence of fear, but the decision to act in spite of it. Conrad himself said that no matter how difficult things became at Rippling, they never came close to how bad those six months were right after Zenefits. And that experience became his reference point, a reminder that he had already survived the worst, so everything else was manageable. Courage, once you have exercised it at that level, leaves a residue. It makes the next hard thing less paralyzing.

The second is commitment. In a crisis, people do not need a leader to have all the answers. They need a leader who is not leaving. There is tremendous security in knowing that the person at the front is staying at the front, regardless of how turbulent things become. That consistency of presence is itself a form of leadership, even when nothing else is going right.

The third is clarity. And this is perhaps the most important one, because clarity during chaos is not about pretending to know the future. It is about being honest about what you do know. It is looking the people you lead in the eye and saying: I do not know exactly how this ends, but I know what we are fighting for, I know who we are, and I know that it is an honour to lead you through this. That clarity, that groundedness, creates stability around you even when the environment is anything but stable.

When the storm comes, and it always comes, nobody follows a title. They follow a person. Make sure you are becoming the kind of person worth following.