5 lessons from Simon Sinek that inspired me to be a better leader

I’ve been fascinated by leadership for as long as I can remember. From my corporate days to starting my own online businesses, I’ve always wondered: What makes a truly effective leader?

I’ve found plenty of answers in Simon Sinek’s work. Over the years, I’ve read several of his books—Start with Why, Leaders Eat Last, and The Infinite Game. Each got me thinking differently about the kind of leader I wanted to be.

Today, I’m sharing five lessons I learned from him, which have genuinely changed the way I run my teams and approach leadership.

Maybe they’ll give you some inspiration, too. 

1) Start by defining “why”

One of the biggest takeaways I got from Simon Sinek is the importance of starting with why. 

You might recognize this from his famous TED Talk or his book Start with Why. He constantly emphasizes that people don’t simply buy what you do; they buy why you do it.

When I first came across this concept, I was running a remote team spread out over different continents. I thought: Isn’t it enough if they just follow the tasks and deadlines I set? But the more I tried to scale my business, the more I realized that clear tasks and deadlines weren’t enough to spark real engagement. 

My team needed a reason behind those tasks—an emotional connection to our mission.

I started having regular check-ins to reiterate our “why.” It was no longer just about churning out content or hitting monthly targets. It became about helping individuals (readers, clients, small business owners) succeed in the digital era. I noticed an immediate shift in motivation. People felt connected to the bigger picture and were more proactive.

As Sinek has put it “People don’t buy what you do; they buy why you do it. And what you do simply proves what you believe.” I found this to be 100% accurate. Once my team understood the why, they took on more responsibility and ownership. They weren’t just working for a paycheck; they were contributing to a shared vision.

2) Embrace empathy

If you’ve read Leaders Eat Last, you already know how strongly Sinek values empathy. 

He believes a leader’s job is to care about their team’s well-being as much as the bottom line, maybe even more. 

For a while, I was so focused on results that I’d inadvertently brush aside how people were really doing. But as our projects expanded and the pressure mounted, I realized that an empathic approach was crucial.

My experiences have shown me that empathy translates into higher morale, better communication, and ultimately, stronger performance. It’s not just a “soft skill.” Empathy can make or break a team’s resilience. 

Think about it: if you’re working remotely and you feel like your boss doesn’t care if you’re burned out, are you going to go the extra mile?

Probably not, right. 

When I adopted a more empathic style—listening more, asking genuine questions about each person’s challenges, and giving them time to decompress when needed—I saw a drastic shift in my team’s attitude. They opened up, and in turn, we started tackling problems together rather than suffering in silence.

I keep this in mind every time a team member is struggling. It reminds me that trust is built when people see that their leader truly cares.

3) Think in terms of the infinite game

I’ve mentioned this in a previous post, but I’ll say it again: short-term wins are great, but they’re not everything. 

In The Infinite Game, Sinek challenges leaders to look beyond the quarterly targets and plan for the long haul. This perspective resonates deeply with me because I’ve seen how chasing immediate metrics can lead us astray.

In my early entrepreneurial days, I was all about hitting monthly revenue goals and celebrating big product launches. 

To be honest, I used to push my team to the brink to meet tight deadlines, and while we hit our numbers, we’d often burn out in the process. Then, next quarter would roll around, and we’d need to do it all over again, often scrambling without a sustainable plan.

Shifting to an “infinite mindset” meant asking, Is what we’re doing right now going to help us thrive years from now? This approach changed everything. 

We started investing more in our people, focusing on brand trust, and building lasting relationships with clients. It’s not that we ignored short-term goals, but we balanced them with decisions that would still hold value down the road.

Another phenomenal thought leader, James Clear wrote, “You do not rise to the level of your goals. You fall to the level of your systems.” When I paired Sinek’s infinite mindset with James Clear’s emphasis on systems, I realized success is about building a platform that can adapt and grow over time, rather than constantly sprinting from one short-term finish line to the next.

4) Cultivate a circle of safety

A consistent theme in Sinek’s work is creating what he calls a “circle of safety.” As I see it, this is an environment where people feel secure enough to express their concerns, share their ideas—even when they might fail—and support one another without fear. 

I’ve had experiences in my previous corporate life where people were afraid to speak up. The results were pretty much always the same: resentment built, creativity shrank, and team morale plummeted. When I started managing my own remote teams, I made it a non-negotiable to welcome all types of feedback.

For instance, during our weekly virtual meeting, I encourage my team to voice any grievances—yes, even if it’s about how a project is structured or if they need more resources. 

People initially hesitated. After all, many workplaces punish dissent. But as they saw that I actually valued their input, it became the norm to address issues openly rather than whispering behind closed doors (or in private Slack DMs).

Sure, it can be uncomfortable to hear constructive criticism about something you’ve worked hard on. But by fostering this safe space, we started identifying problems faster, innovating more, and genuinely trusting each other’s motives. 

5) Prioritize trust over talent

This is the lesson that really sealed the deal for me: If I have to choose between a highly talented individual with questionable integrity and a moderately skilled individual with unwavering trustworthiness, I’ll pick the latter any day. 

In my years of running various online ventures, I’ve encountered brilliant people who delivered impressive results but left a trail of burned bridges behind them. Sure, they could produce quick wins, but those wins often came at the expense of team cohesion.

Eventually, I decided enough was enough. I’d rather invest in developing someone who’s open-minded, honest, and eager to grow than keep someone who has a toxic attitude, no matter how skilled they are. 

Once I made that shift, I noticed my teams became more cohesive. People were happier to share workloads and more willing to admit mistakes. And trust me, this is invaluable in our niche. 

Final words

That’s it for this one folks. I hope you got as much out of these lessons as I did. 

Simon Sinek’s ideas challenged me to rethink the fundamentals of leadership—from finding a clear purpose to cultivating an environment of trust and empathy. It’s not about managing people for short-term gains. It’s about guiding them in a way that brings out their best for the long haul.

Don’t get me wrong: none of these lessons are a quick fix. Like anything else in leadership, they take time, consistency, and a good measure of humility. But if you’re open to changing how you view success, your team can become the kind of cohesive unit that not only hits targets but thrives as a community.

Until next time. And as always, keep leading with heart.