Leadership Development: How to Become a Legendary Leader (in Just 5 Minutes a Day)

14 min read
Person standing on top of a mountain after investing in his leadership development and becoming a legendary leader.

For many founders, one of the best parts of leading a young startup are the one-on-one relationships they’re able to develop with their small-but-passionate team. And often, these relationships become more than strictly professional connections; they become genuine friendships between two people who share the same vision to build something great and leave their mark on the world.

But as a startup begins to gain traction, that initial team is probably going to grow. Obviously, growth’s a good thing and, at least for a little while, that growth won’t change the team dynamic much; it’ll still be possible to build those personal relationships with each new hire.

But unfortunately—as many founders have discovered—that doesn’t last forever.

The more a startup grows, the more responsibilities the founder has; and the more responsibilities the founder has, the harder it becomes to find time to invest into relationships.

In this article, we’ll explore the leadership development strategies that can help you overcome this to become the legendary leader your business needs to drive it to success.

The (Often Painful) Cost of Neglected Relationships

And at the end of the day, there’s no way around it: Relationship development at 50+ employees is going to look and feel a little different than it did at 5.

By the time a company reaches 50 people, many founders are struggling just to remember everyone’s name, let alone develop meaningful relationships with them.

And for a relationship-minded founder that cares about their leadership development, this can often feel like they’re losing touch with the very soul of their business; like they’re being pulled away from the things they enjoyed most about their startup in the first place.

In fact, I’ve known some founders to go so far as to say it feels like they’re betraying their team and the culture of their startup.

As a result, many founders find themselves feeling lonely, disconnected, and uncertain about the true thoughts and emotional states of the people in the company. This is the point where a legendary leader often finds themselves inching toward that proverbial “Ivory Tower.”

Upon reaching this point, many CEOs often overcorrect in their leadership development efforts to get back on track. They double down on the things that make them feel connected to their people—such as weekly skip-level 1:1’s with more people than they can actually sustain—only to find themselves feeling like they’re spending too much time in reactive meetings and not enough time on the proactive tasks that move the needle most.

Success and Relationships Are Not Mutually Exclusive

The truth—as many founders discover—is that there just isn’t enough time to invest in their business the way they need to and their relationships the way they’re used to.

Eventually many CEOs come to the realization that this overcorrection is unsustainable, and so they have to resign to the idea that having deep, meaningful relationships with every team member simply isn’t possible.

But it doesn’t have to be that way.

Although you may not always be able to interact with every single team member, there are a handful of leadership development strategies you can use to continue building meaningful relationships with the people in your company and, as a result, keep close tabs on the culture of your business.

And this all starts by harnessing the power of something you’re probably already doing as part of your leadership development efforts: Having watercooler conversations.

Watercooler Conversations: Your Key to Relationship Scalability

Watercooler conversations are pretty self-explanatory: They’re those quick one-on-one conversations that take place in the breakroom, around the coffee machine, or as you walk down the hall on your way to the next meeting.

They happen pretty naturally in the flow of business. In fact, I bet you’re already having watercooler conversations. But here’s what you’ve got to ask:

  • Are these conversations intentional and focused?
  • Have you developed the skill to go deep in the limited time available?
  • And are you leveraging the information you gain in these conversations to further deepen the relationship after-the-fact?

In my experience, probably not; at least, not to the extent you could.

Because used well, a 5-minute watercooler conversation can be used to deliver deep, meaningful interactions with everyone at your startup; from your head of product to your media intern and everyone in between.

At the end of the day, watercooler conversations—and the quick interactions that follow—can be just as impactful as 1:1’s at a fraction of the time and energy cost.

Let me illustrate this concept with a true story about one of my clients.

Delivering a Memorable, Meaningful Interaction (in Five Minutes or Less)

Awhile back, I was working with Rob (name changed for confidentiality), the CEO of a Sequoia-funded company. At the time, the company had about 400 employees and—understandably—Rob felt unable to stay connected with his rapidly-growing team.

So we launched Care for Culture—the scalable internal relationship program we developed for entrepreneurs—with Rob and, a few weeks later, he shared this incredible story.

He told me about a watercooler conversation he had with Erin, a young data analyst and new hire he hadn’t gotten to know yet. Over the course of the 5-minute conversation, he discovered she’d previously taken a year off her career to care for her ailing mother.

As many of you probably know, a young professional taking a year off their career—especially in a competitive environment like Silicon Valley—is pretty unheard of, and Rob was deeply touched by Erin’s dedication to her family.

Immediately following that conversation, he dictated the following request to Jill, his Engagement Manager:

Hey Jill, please draft an email for me to send to Erin on Monday, one week from today:

Hi Erin,

I was just thinking about our conversation last week and wanted to let you know I really enjoyed it. I’m sure that wasn’t an easy decision to make, but I’m touched by your dedication to your family. Choosing to take a year off your career was very brave.

As you know, one of the pillars of our culture here is caring for one another, and you showed me that you’re a living testament to what that looks like. Thank you so much for what you bring to this company.



A week passed and the email was sent. As you can imagine, Erin responded almost immediately and was blown away to personally hear from the CEO a week after their initial conversation.

And because of the candidness and authenticity of that interaction, both Rob and Erin left feeling much more connected to one another and to the company as a whole.

The Surprising ROI of Just Five Minutes

And here’s the best part: Between the watercooler conversation and the email dictation to Jill (who then wrote the email on Rob’s behalf), that whole interaction probably took Rob all of 5-7 minutes.

5-7 minutes. That’s all it took to deliver an exceptionally powerful, unforgettable experience to an employee Rob had never met before. So in the time it takes to hold a single 30-minute 1:1, you could deliver the same value to up to six different people.

Not a bad ROI for such a simple leadership development strategy.

And it illustrates an important point: At the end of the day, it isn’t about how much time you invest into an interaction that makes it meaningful. As Maya Angelou said, “People will forget what you said. People will forget what you did. But people will never forget how you made them feel.”

Generally speaking, people aren’t necessarily going to remember the experience itself; they’re going to remember how that experience made them feel, whether it took you 60 minutes or 6.

Note: The key to that whole interaction is how simple and easy it was. To make this process work, you must reduce as much friction as possible.

Rob leveraged his time to the extreme by having Jill, his Engagement Manager, draft his emails for him, reducing a 15-minute process to less than 5.

To get the most out of these principles, I recommend doing the same. Click here to learn some of the benefits of scaling your relationships (and your business) with the help of an Engagement Manager.

Nailing Leadership Development and Becoming a Legendary Leader

And here’s the best part of all of this … The value of the interaction doesn’t stop there. Think about it: When was the last time you kept an amazing experience to yourself?

When something great happens, it’s practically second-nature to tell others about it. And that’s exactly what tends to happen here: That person is probably going to forward that email to their family, friends, and coworkers.

And even if you don’t have the time to provide interactions like this to every one of your team members, those you are able to interact with will act as a force multiplier as they share their experience; and soon that single interaction is touching far more people than just those initially involved. And then the magic really happens:

As stories are told over and over again, they become something more: They become legends. And that’s how this leadership development strategy turns you into a legendary leader: One interaction—one story—at a time.

Let me share another true story from a client to illustrate what this process of leadership development looks like.

A Legend in the Making

This client, we’ll call him Alex, was the CEO of a very successful startup.

About eight weeks into the Care for Culture Program, Alex received an email from his front desk receptionist, Mary. Mary was something of a “mother of the herd” to the rest of the team and, as a result, had a good pulse on the state of the firm.

Here’s what Mary had to say:


I‘ve been hearing your name come up a lot lately and I thought you’d like to know what people are saying about you:

– “His conversations are always so thoughtful and genuine,”

– “He works so hard. I don’t know how he finds the time to stay connected with everyone,”

– “He just really cares about the people in the company,”

– (Don’t let this one go to your head) “How is he so perfect?”

Thank you for setting such a great example!

Generating feedback like that just takes a little time, intention, and consistency. And take it from my clients: It’s worth every minute, because the benefits don’t stop there.

3 Benefits of Investing in Your Leadership Development and Becoming a Legendary Leader

By personally investing into a handful of internal relationships, you’re going to get more than just goodwill. You’re also likely to develop loyalty within your team, reduce CEO loneliness, and create a healthy, quality company culture.

Let’s take a quick look at each of these three leadership development benefits.

#1: Overcome CEO Loneliness

According to many of our CEO clients, one surprising benefit of the Care for Culture Program is that these leadership development practices left them in a better emotional state. And it makes sense:

According to HBR’s CEO Snapshot Survey, nearly half of all CEO’s report feelings of loneliness. This is especially true for first-time CEO’s, with nearly 70% reporting feelings of loneliness that negatively impact their performance.

It happens all the time: Once you get to the top, it’s easy to feel like you can’t really talk to anyone about the big challenges and decisions you face on a day-to-day basis.

After all, you’re the ultimate decision-maker, and it often feels uncomfortable or inappropriate to share potential business decisions with your executive team (since they’re your employees) or board (since they have final say in your business).

The result, as Bill George (@Bill_George) points out in How to Overcome the Loneliness of Being a CEO, is many leaders who feel abandoned and alone in their time of need. Left unchecked, this often leads to a debilitating sense of loneliness.

But when you start receiving emails like the one above, it can be a powerful reminder that people do care, and a great way to realign with why you’re doing all of this in the first place.

And while these emails might not necessarily change the reality of the situation, they often make the perceived loneliness much more bearable.

#2: Quality Culture

Like proactivity, “culture” has become something of a buzzword in Silicon Valley: There’s a bunch of people talking about it, each with their own definition of what it means.

Here at Mindmaven, we have a very simple definition: Culture is the sum of all actions taken by a group of people.

The key words there are “actions taken.” In other words, your company culture isn’t defined by what your slide deck or mission statement says, but rather by how you and your team act on a day-to-day basis.

But although culture is defined through the actions of a group, arguably one of the most influential factors in determining the culture of a company are the actions of its leader.

The actions you take on a consistent basis set the course for the rest of your company. So when you habitualize empathy, connection, and genuine care, you’re likely going to find those same traits emulated within your organization; not only in how your people treat one another, but in how they treat customers as well.

#3: Team Loyalty

By consistently delivering these types of interactions to your team, you show them that you’re invested and interested in them not only as employees, but as individuals.

When you create the type of work environment where people feel appreciated for who they are—not just what they do—their loyalty tends to skyrocket. And as loyalty increases, attrition decreases, leading to teams more likely to stick around through good times and bad.

Above All, Be Authentic

By investing and committing to your leadership development, you’ll likely …

  • Gain the respect and loyalty of your team,
  • Overcome CEO loneliness, and
  • Create a higher-quality culture.

But I’ve worked with enough clients to know what at least some of you are thinking: “Isn’t it disingenuous to use something as sacred as relationships to achieve business objectives?”

And I’ll tell you the same thing I tell them: You’re looking at it the wrong way.

As long as your interactions and engagements are genuine—meaning you truly want to connect with your people and fully believe the things you say—the fact that you’re leveraging a system to help deliver these experiences isn’t going to bother anyone.

At the end of the day, the Care for Culture Program—like all things involving relationships—is largely about intention.

If your primary goal of your leadership development is simply to accomplish a business objective—like lower attrition—then it doesn’t matter how you interact with your network; it’s always going to feel inauthentic.

But if you approach each interaction with a genuine desire to learn about and care for the other person—to make them feel special, important, and valued—no one’s going to care what system you used to deliver that experience.

All they’re going to care about is how those interactions make them feel, and that you keep delivering them.

Ready to Start Scaling Your Relationships Today?

If this article on leadership development resonated with you and you’re interested in exploring how to bring Care for Culture to your company, schedule a free check-in call with us!

During this 30-minute consultation, you’ll meet with one of our experienced, results-driven coaches to develop a quick-start plan to begin implementing some of these ideas within your organization immediately.


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