5 Habits Of Exceptionally Likeable Leaders

At 26 years old, I was the founder and CEO of a fast-growth startup. We were generating millions in revenue, on the covers of business magazines, and even had a slick office in a desirable area of Orange County California. The last thing I expected was to be disliked by most of my 40 employees.


This is a picture of me (bottom center) with my staff after an employee party paddle boarding through the bay in Newport Beach, California. From the outside, everything looked great. But in reality, there was an emotional divide severing my employees from their leader.

Just days after this photo was taken in 2012, my mentor asked if we could have a private conversation. At my surprise, he listed off a range of negative feedback he had heard from my team.

He looked me in the eye and said, “Dale, you hurt people and you don’t even see it.”

At this point, I was speechless. The details of how people had perceived my leadership, began to open my eyes to the wake of emotional destruction I left behind me. And while some of these flaws are acceptable for the average person, they were deadly for a business owner in my position.

It reminded me that self-evaluation is helpful, but evaluation from someone else is essential.

Over the next several years, I dove deep into healing. I enrolled in a $12,000 executive psychotherapist course, had a monthly appointment with a therapist, read over 15 books on emotional leadership, and made an immense level of progress over the coming months.

“Dale’s entrepreneurial journey is very diverse, but he truly does seem to have that magic touch in leadership, regardless of the industry.”

-Forbes Editor, Evan Kirkpatrick

In November of 2014, my stock was acquired. But it was the lessons I learned during this season, that changed my trajectory of success forever. There’s an old saying that all leaders should know:

“What got you here, won’t get you there.”

It’s the lessons of this season that not only allowed me to come back and earn millions, but to lead with integrity, to elevate and inspire those around me, and to create companies that change the world.

Since selling my stock, I’ve been overwhelmed with thousands of inquiries for mentoring, consulting, and speaking. It was evident that if I wanted to share my learnings with the world, I would need to package them up into an effective curriculum. A curriculum that that was affodable, useful, and deep.

On January 1st, 2015 I launched StartupCamp. A school for aspiring entrepreneurs, bloggers and dreamers. A school for people tired of working for someone else. A school for those who have brilliant ideas and burning passions but just don’t know where to begin.


Inside the curriculum, there are over 100 master takeaways. These are pieces of wisdom that quite literally alter the trajectory of a startup. Some are for branding. Some are for marketing. Some are for ideation, finance, and legal. But I have summarized a few for leadership below:


In module #8, I help new entrepreneurs recognize the power complaining can have on those who follow them. The CEO of Clif Bar once told me,

“The reason executives get paid more, is to bear the immense weight of the company so others don’t have to.”

If even one employee or subordinate hears you complain about anything, whether it’s today’s traffic or the deadline you’re struggling to hit, or how you lost a client, it places unnecessary weight upon their shoulders and builds contempt in the hearts of everyone who follows you. Leaders get paid to stay quiet. Not with everyone, but surely with your team.

Because the only thing complaining does, is convince other people that you are not in control.

I’ll leave you with this. If you struggle with complaining, you must realize the problem is deeper than spewing out a few words of frustration. Your heart is not content. You embody a false sense of entitlement and those words will slow your progress to becoming the entrepreneur you want to become.

Question: Do you struggle with complaining? What behaviors or thinking needs to change in order to remove this habit?


At our core, we are all selfish beings. And focusing energy on selflessness has always been a common win for leaders, but what is rare is those who can communicate with selflessness.

To intentionally craft their words for each individual audience. To be considerate enough to change their style to accommodate the needs, vernacular, culture, or beliefs of those who are listening.

Thoughtfulness is the most effective version of communication.

In Module #6, I uncover the 15 keys to empathetic marketing that convert people into customers. Because good communication should captivate. As entrepreneurs, we must realize our success is less dependent on the ever-changing strategies and tactics found in marketing articles, and more reliant in our ability to understand how to talk to people. If you can unlock this, you can unlock millions.

Question: Are you prideful in the way that you speak to others? Are you selfish in your conversations? How can you become more empathetic in the way you communication? Better yet, how can you become more empathethic in the way you market?

“Dale’s level of business wisdom is rare. And the fact that he has packaged his knowledge so beautifully online is truly a gift.”

-Blake Mycoskie, Founder of TOMS Shoes


Every battle has a consequence. A victor and a failure. It’s common for leaders (especially A-Types) to turn common confrontation or debated discussion into a battle. We lose sight of the person and focus our sights on the win.

We fight with intense fervor and find our moment to slam the door shut. Bam! “I’m right!” But then it sinks in… the hurt and defeat we caused another human on an issue that never had the merit of such a pain in the first place.

In Module #10, I teach students “How To Think Like A Mature Entrepreneur”. The theme is quite counterintuitive, but this philosophy has produced more valuable relationships than I can count.

In that module’s 30 minute coaching video, I share a heart wrenching personal story and give students a detailed approach on how to win the hearts of those around you. Because when we can create loyalty, we can create an audience, and with an audience, you can launch a product. But without it, you’ll drown trying. The key lesson is this:

It takes guts, maturity, and strength to be gentle.

Question: As leaders we must clearly understand what we divide for, debate for, and die for. Are you too intense with people? Is there anyone you need to apologize to? Making things right is helpful, but never hurting someone in the first place in optimal.


I see too many incredible leaders hide behind their company. Sure, they can build a strong brand and execute a list of corporate initiatives, but at the center they lack the self confidence to even follow themselves.

Many of us believe when people engage with our companies or our ideas that we are adding value. But value is different than connection. Connection only occurs when the leader incorporates their humanness and their story within their work. Their weakness, their realness, and their authentic desire to grow. This is the beginning of relationship and the only thing worth following.

Question: Are you afraid of leading? Do you need help recognizing your own value before you can stand in front? You might want to consider the StartupCamp program.


In all of the leadership habits I have learned, humility trumps all. Have you ever met someone who authentically compliments you, lifts you up, and affirms your character? Almost as if you’re more important then anything else at the time?

The capacity of offering this gift derives from a heart of humility and genuine belief in the value of other people. It’s a hard quality to develop as a leader, but the more you can grasp about the equality of the human condition, the less you will tower over those around you.

It reminds me of this truth: A great leader is always willing to be little.

As leaders we can afford to be broken, but we cannot afford to be emotionally immature. People will follow you in spite of a few bad decisions. People will not follow you if you are unaware of your weaknesses. As a leader, you must develop the elusive skill of leading confidently and purposefully growing or you will forever stand still.


Do you want to become a captivating entrepreneur? Do you want to start something great? If you’re looking for a practical guide with timeless principles that never fade, principles that push for a healthy type of success, one with integrity, honor, and respect, then my StartupCamp school might be perfect for you. Watch my video below.

Enrollment Ends

jQuery(document).ready(function(){ countdown(); setInterval(countdown, 1000); function countdown() { var now = moment(), then = moment().endOf(‘week’).subtract(1,’day’); ms = then.diff(now); days = Math.floor(moment.duration(ms).asDays()); then = then.subtract(days, ‘d’); if (days < 10) { days = '0' + days; } ms = then.diff(now); hours = Math.floor(moment.duration(ms).asHours()); then = then.subtract(hours, 'h'); if (hours < 10) { hours = '0' + hours; } ms = then.diff(now); minutes = Math.floor(moment.duration(ms).asMinutes()); then = then.subtract(minutes, 'm'); if (minutes < 10) { minutes = '0' + minutes; } ms = then.diff(now, 'milliseconds', true); seconds = Math.floor(moment.duration(ms).asSeconds()); if (seconds < 10) { seconds = '0' + seconds; } diff = '‘ + days + ‘‘ + hours + ‘‘ + minutes + ‘‘ + seconds + ‘‘; jQuery(‘.countdown-timer’).html(diff); } });

Are you an aspiring leader? What has worked for you? What have you seen work well for others? Let me know in the comments below.

Learn About My Story

The post 5 Habits Of Exceptionally Likeable Leaders appeared first on StartupCamp.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s