THE LIFESTYLE ENTREPRENEUR

Read time - 4 minutes

Leadership

I’ve posted on LinkedIn every day for 7 months now - 216 days to be exact.

It’s been a transformational experience in many ways, and I believe will continue to transform my work and career.

In reflecting on the past 7 months, I pulled my top 20 posts by engagement and categorized them, here’s the breakdown:

• 30% Leadership

• 20% Progress updates

• 15% Sleep

• 10% Wellness/Self-care

• 10% Productivity/mindset

• 10% career philosophy

• 5% Art of play

Which is deliciously convenient, because Leadership was my topic this week.

Don’t you love it when things workout like that?

Seeing leadership as my most engaged topic feels really good, because it’s one of the topics I feel most suited to write publicly about.

In terms of content pillars, it fits all the requirements for a great one:

• I have more leadership experience than most people

• I have more varied experience than most people

• I’ve been a student of leadership my whole career

• I’m curious about leadership, I always want to learn more

Two other reasons I’m uniquely suited to talk about leadership:

My current work - I work with leadership teams and founders of small business every day, so I observe and coach their leadership in the pressure cooker that is managing small business.

All the mistakes I’ve made - I can point to a bad example of leadership from personal experience for every single leadership attribute I’ll ever talk about.

Seriously - I coach people on leadership every day, and for every principle I share I can come up with instances where I’ve failed or come up short.

Living it, observing and coaching it, and failing at it, all have shaped my philosophy on leadership greatly, and also formed my core belief - leadership is a learned skill that requires consistent effort for success.

What is leadership?

Leadership is guiding, leading, and inspiring people to achieve a common goal.

Leaders set the vision, and inspire people to execute that vision, of an organization.

Why is Leadership Important?

Leadership is the backbone of any organization - it’s responsible for setting the vision, culture, and direction. It’s also the primary determinant of success or failure of an organiztion.

Over time, the success of an organization can almost entirely be attributed to the effectiveness of it’s leadership.

Because of it’s position of importance - leadership is also the most important skill a human can learn if they want to have any form of success in this world.

Are there good careers that don’t require leadership?

I suppose there are some - highly specialized subject matter experts, like:

• Securities trading

• Medical specialists

• Financial analysts

• Programmers

But most of those people, at some point, will be required to work in teams, if they want to progress. And that places them right into needing to learn leadership - because leading up and down chains of command, along with working with teams, is a core leadership principle.

Except for a few niche jobs, leadership is inescapable.

Professionals then have a choice - let leadership happen as a matter of chance and be clueless about whether they’re good leaders, like most people. Or accept the fact that it’s a skill and work to develop themselves.

Why is leadership mostly bad?

An interesting human phenomenon, is that despite most people agreeing that leadership is critical, most also believe leadership is mostly bad.

A Gallup study from 2020 famously reported that only 15% of the global workforce is engaged in their jobs.

A 2021 Harvard Business Review report found that 38% of employees were actively engaged at work, and 14% were actively disengaged.

While there are many causes for poor employee engagement - leadership is the primary one.

I don’t know the sample size and company sizes of these two reports, but I would guess they’re on medium to large businesses. And anecdotally I can say leadership quality is worse in small business than in enterprises.

So why is the standard so low for good leadership?

That’s a complicated question, which I have only opinions:

1. Our early exposure to good and bad leadership is mostly a matter of luck - you start your career and are either exposed to good leadership or bad, and usually don’t have good points of comparison.

2. Structured leadership training is reserved for people much later than their formative years.

3. Small businesses make up 99% of all businesses, and employ the majority of people.

Small businesses rarely get past the level of scale where resources are invested to develop leaders. Because a majority of employees come from small business, and leadership development is lacking in small business, logic dictates that small business keep the bar for good leadership low.

The majority of people interact with leadership as a matter of chance throughout their careers - some see great leaders while others see bad leadership.

And without taking active measures, the majority of people will spend their careers leading by chance based on what they’re exposed to.

What are the principles of leadership?

I was lucky in my early exposure to leadership. Not only did I expose myself to some of the world’s best structured leadership training - namely the US Marine Corps Infantry - I was also exposed to both great and poor leadership within short intervals.

In high school athletics my basketball coach was a world-class leader, while my lacrosse coach was an amateur fulfilling a side hobby. The difference was stark.

In the Marine Corps, my first company commander was truly one of the best leaders I’ve ever met. He led us through the invasion of Iraq and lived every principle I value every day. Returning home, I was assigned to a new company commander - he was so bad he got fired when we were in Afghanistan.

These contrasting early exposures, along with an early career structure around leadership, shaped everything I’ve done in my career.

Starting businesses 13 years ago, and operating them since, has crystalized those lessons in the pressure cooker that is building companies.

The most important learnings I’ve had throughout my career have come from my own leadership failures.

I mostly exhibited good leadership in my career. But there are periods and instances where I did not.

Seeing myself - a good leader - become a bad leader, proved to me that leadership is a learned skill based on consistent habits.

It’s not a matter of natural ability. The charismatic leader who gives a great speech and inspires the masses is largely a myth.

Great leaders show up every day, and exhibit qualities every day that make them leaders.

Those qualities require consistent work. Day in and day out. There’s nothing sexy about it.

Because leadership is learned, anyone can become a great leader.

Here are my core principles of good leadership:

• Lead by Example - Demonstrate the behaviors, work ethic, and values you expect from your team. Your actions set the standard for the entire organization.

• Extreme Ownership and Accountability - Embrace ownership of outcomes, demonstrating accountability for both successes and failures. Encourage team members to take ownership of their work as well.

• Vulnerability and Empathy - Foster an environment of openness and authenticity by being vulnerable about your own experiences. Practice empathy to understand and support your team members on a personal level.

• Resilience and Persistence - Model resilience in the face of challenges and setbacks. Show persistence in pursuing goals and inspire your team to do the same.

• Continuous Learning and Adaptability - Prioritize ongoing learning and remain adaptable in a changing world. Lead the way by consistently seeking new knowledge and skills.

• Ethical Decision-Making and Integrity - Uphold strong ethical values and make decisions with integrity. Set an example that reinforces the importance of ethical behavior throughout the organization.

• Clear Communication and Vision - Communicate your vision clearly and transparently. Communicate the WHY early and often.

Are there natural leaders? Just like any skill, there are people with more or less talent. So some people start off in a much better position for good leadership.

But as you can see above - while we’ll all naturally exhibit higher or lower levels of each principle - they can all be developed through work, discipline, and consistency.

How can I become a better leader?

To be a great leader, one must align their lives around it:

• Create a mindset of servant leadership

• Set an environment that allows it

• Exhibit daily habits that promote it

• And care for themselves physically and mentally

Leadership requires consistent daily work. And to put in the work, a leader must prioritize being a leader.

In practice what that means, is every day when you show up at work - when looking at the mountain of tasks and priorities on your plate - leading others needs to be the main priority.

If it’s the priority, and you setup an environment that allows it, you’ll be in a position to lead.

And to lead you need to exhibit daily habits that make you a good leader to your people.

Little habits like listening, respecting people’s time, and creating structure for growth.

The final piece is caring for yourself physically and mentally

Leadership is a higher level skill. It requires higher brain function.

If you’re overworked, overstressed, and undercared - you’ll constantly be in survival mode.

And good leadership doesn’t come from survival mode.

When it’s all boiled down it’s pretty simple:

• Care for yourself

• Prioritize leadership

• Put in the work daily

For anyone who’s thinking about how they can be leaders - I’d recommend starting with a daily question - how can I be a good leader today?

Just asking yourself that will illuminate your priorities, and help you focus on it.

Talk to you next week,

Mike