[TRAINING] Heroic Leadership For Remote Teams: Training & Exercise

Yes, You Can Empower & Foster Future Leaders In a Remote-Only Workforce

Dear Digital Consultant, 

As your team grows, self-management and leadership skills become more important.

Reflecting on companies that I’ve consulted, I can trace that the core root of most of their issues lay within their leadership.

My aim with this training is to give you some fundamental principles of digital leadership. Real insights from being a leader across multiple teams across the globe in a digital, remote first economy.

At the end of this training, you will have a short exercise to apply what you will learn in training.  I encourage you to complete it on your own and also to complete it with your team.

There are books out there, I won’t name them,  that base their “remote-first” leadership lessons on research, surveys, employee questionnaires etc. And somehow, the authors believe they can dictate a protocol for working and leading effectively in a remote economy by theory and research alone.

While that’s ok for some, it’s not for us.

What we will be discussing here is brass tax, real world, 1st hand experience, and lessons from my own failures of leading hundreds of people online, building multiple companies, remote only, across 12+ timezones, from the comfort of my home in San Diego.

The main goal of the leadership approach we will focus on is to answer the following question:
How do we harness, empower and lead a team that contributes their best performance, consistently, over time?

Keywords I’d like to highlight are performance, consistency, and time.

Performance because results matter.

Consistency because that’s the name of the game.

And time, because we all, as humans, experience and go through time. And it’s in how we remain constant in our pursuits over time that divides the winners from the losers.

So, how do we harness, empower and lead a team that contributes their best performance, consistently, over time?

From experience, the answer to this question is within the framework of Heroic Leadership.

We will dive into Heroic leadership as it applies to you, your teams, and the style in which you decide to lead yourself and those around you, especially those who depend on you.

We will be diving into the following:
  • The Definition of Heroic Leadership
  • The Essence of a Heroic Leader
  • The 5 Pillars of Heroic Leadership
  • Becoming a Heroic Leader: Simple Exercise

What is Heroic Leadership?

Heroic Leadership is the practice of disciplined thought, communication, focus, and action.

These are the things that we practice every single day, but it’s about being intentional of how we think, what we think, how we think about ourselves and others, how we communicate, our word choice, tone of voice, where our focus is at, where we spend our time, and how we take action.

This practice leads to effective selfleadership. Remember, the first person that you lead is yourself.

You have already led yourself to whatever outcomes you have in life right now. Every outcome you have right now is based on your decision yesterday. It’s based on the habits that you’ve already created. The beauty is that you can change your outcomes starting now.  Everyone has that power, and everyone has that capability.

The Nature of Trees

There’s a story from Jim Rohn about the nature of trees, and as I tell this story, I imagine the large tropical banana tree I have in my backyard.  If you look at that tree, its nature is to grow as much as it can. It doesn’t just stop growing because it decided one day to say “enough!”.  No, this tree, especially my banana tree, is almost 9 feet tall and has already sprouted 8 offshoots that will probably also grow to 9+ feet…

From this, we can gain insight: the law of nature is growth.

As humans, unlike the trees, we have choice and power to change. And we also have the power and choice NOT to change.

Heroic Leadership starts with taking that first choice to grow, to change, for the best.
I believe that we should choose and invest in ourselves to grow in as many areas as we can in our life, daily. Of course, within reason, but daily. Because in doing so, we lead ourselves to the future that we want and also have a larger capacity to lead others as well.

We all have a personal responsibility to ourselves and those around us to make this choice.

The Essence of a Heroic Leader

Why not just call this “typical leadership training” and leave it at that? After all, all leadership training is the same, right?

Well, I personally believe that there is a difference.

Just like there is a difference between managers and leaders.

It’s the same difference between leaders who lead and leaders who inspire.
The goal of Heroic Leadership is not just to have you lead effectively but also to lead an inspiring life for yourself and for those around you.

Leading in a way where people will say: “hey, this person’s a little different, in a good way. Like, I don’t know what, but something about them makes me want to become a better person.”

You have the power to be a positive influence on those around you.

And guess what happens when people work with someone who inspires them to become better?

The pressure will definitely add up in a healthy way. Because if you become that person for others, the question becomes: “who am I becoming?”.

Why Heroic?

Because Heroic Leaders don’t shy away from reality.

We face reality as it is, with its difficulties and complexities.

We are dedicated to the mission our team is embarking on and the people involved in the mission.

We make the difficult decisions that lead to the greatest good towards the goal at hand.

We own the outcomes: the good and the bad. Never play the blame game, and give credit to those who helped us succeed.

We have the wisdom to understand the difference between delegating a task and delegating responsibility. (Hint: we don’t delegate responsibility).

We understand the weight and power of our words.

We understand that it’s in how we do our work that matters, in the style of which we carry ourselves: to achieve our goals virtuously.

Why Does This Even Matter?

I have a guarantee for you:

The same work you do for a living is being done by other companies right now.

But what matters most, especially with service businesses, is the style in which you do your work and deliver results for the client. The relationship you build with the client, the approach you take with your communications, and the confidence and expertise you demonstrate. These are the intangibles that make you unique, and no matter how hard others can try, they can’t be you.

The 5 Pillars of Heroic Leadership


There are 5 Pillars to Heroic Leadership. These are habits that build upon one another. We crafted them as habits because you want to practice all of these as you develop as a Heroic Leader.

Remember: you are what you practice.
Heroic Leaders:
  1. Set the stage
  2. Are steady
  3. Take informed execution
  4. Facilitate movement
  5. Fuel others

Set the Stage

As a Heroic Leader, you set the stage for how you want others to feel, how you want others to treat you, and your team’s behavior. And that’s powerful.

This is probably the #1 lesson and thing I work on when working with founders and CEOs: understanding the weight of their words.

Every word that you say and don’t say delivers a message, intended or unintended. And these messages create behaviors: positive or negative.

In direct-response copywriting, the most important part of a sales presentation is the first 30 seconds.

Why? Because it sets the frame of mind for the audience.

Now, you don’t have to be a sales expert to set the stage, but you do have to understand your audience, namely your team, read the room, understand situations and communicate accordingly.

In the digital-first communication world we live in, we set the stage in many different modalities.

We use:
  • Text
  • Recorded Video
  • Voice notes
  • Video Meetings

How can we use these modalities to also communicate non-verbally online?

We have the power of:
  • Emojis/gifs
  • Voice tone
  • Text tone
  • Eye contact on video calls
Hint: you can pre-framing a text message by calling out that the tone may sound “low” and that you are coming from a place of understanding when sending it. Here’s what I’ve used to send out hard messages to a team across the country “I know there is no tone in text and the tone of this message will come across as “low-energy”, but I want you to know this comes from a place of empathy and understanding…”

There is power in setting the stage correctly with your team. You will be able to direct your team through your verbal and non-verbal communication to where they need to be led, towards success, even in difficulty. And they will want to follow by being fully enrolled and aligned with your message.


Heroic Leaders are notably steady, especially when experiencing difficulty or company growing pains.

When difficulty or growth pains happen, it’s natural to react. But reacting to situations creates more stress and draining and may not yield the best outcome. 

As Heroic Leaders, we have to pause, keep our composure, and respond appropriately to the situation at hand. This takes repetitive practice, but it’s good to know ourselves, so we come prepared for your next difficult situation.

Identify what your known stressors are and what habits you can develop to counter them.

For example, before responding to a high-stress situation, lay down for 15 minutes, step away for an outdoor walk, or take a cold shower.

Being steady goes hand in hand with setting the stage; Your team will respond or react depending on how you address tough situations or seasons.

Informed Execution

Heroic Leaders take action based on information. There are two primary data sources that fuel every Heroic Leader.

The first is very clear to everyone: the key performance indicators, numbers and stats of a company, team, or department performance. This is the basis for data-driven decisions.

However, the real world isn’t as binary as that since we have to also deal with emotions. It’s just part of the process of being human. You manage your emotions, those around you, and your client’s emotions.
If you work with humans, you work with emotions.

Which is why it’s important to also review the second data source for Heroic Leaders: trusted advisors.

As Heroic Leaders, we must look at the data and also get what I like to call a “sanity check” by talking through situations or decisions with trusted advisors.

Who are the people in your life and business that you trust? I advise you to create a small council of advisors for the areas of your life and business so you can leverage their experiences in order to craft your own.

The most expensive experience is on your dime.

If you don’t have advisors, you can hire them or buy experience from reading books. Books are hidden treasures because for the price of $20-50 you can learn years of someone else’s experiences in a week or if you’re like me, over a weekend.

The Only Assumption To Make

A key note to take away from making informed decisions is not operating under false or negative assumptions. We all make assumptions however, it’s important to catch ourselves in the act and also call each other out when making negative or false assumptions.

With these types of assumptions, we imagine the worst and start creating false narratives in our minds and with others, leading to stress, gossip, and misled activities or negative actions.

The best way to combat these is to clear the air by calling out assumptions and having open dialogues with your team and clients, not being afraid to call out the elephant in the room.

The only assumption I would encourage you to make is assuming positive intent.

When working with others, be it your clients or team, one powerful technique I’ve learned is to assume that the other person I’m working with has a positive intent when working with me.

Of course, you must use caution and not act blindly if someone is actually out to harm you. But for the most part, your team, your clients, and you want the same thing: to succeed.

Imagine how different your interactions would look like and feel if you only assumed the positive intention of the other person.

This mental model has changed my life and mental state.

Facilitate Movement

The beauty of leading teams remotely is that you will get to the point where you are orchestrating the team and facilitating movement. The antithesis of this habit is to be a bottleneck or to micro-manage your team, neither of which Heroic Leaders are.

As you orchestrate the symphony of your team,  you want to constantly share the vision of where the team is heading, the mission, the values you stand by, and the impact the team is having in the market and with your clients.

These “soft” skills in communication actually accelerate, streamline, and amplify the work your team is already doing.

Being an orchestrator also requires having clear documentation, processes, and accountability with the team. This flywheel does take effort to develop, but once you have it running, it’s easy to keep spinning.

In addition, you must also identify the team’s weaknesses and fill the holes with training, support, tools, and resources.

Since you serve clients on a regular basis, you will come to the conclusion that not everyone on your team can operate or deliver at your level at first. And that’s alright. 

As Heroic Leaders, we must find the Minimum Level of Acceptability.

This is not to think by minimal standards or to lower your bar by any means. It’s meant for you to have a real grasp of what your clients expect, what your team can do, and your own personal standards of delivery. 
For instance, you may perform your services at a 95% level of excellence while your team is working to be at 80%. But the thing is your client can’t tell the difference between anything above 70%. Meaning if your team delivers at 71%, your client wouldn’t tell the difference since their needs are met. 

This is not meant to lower your standards but to give you a perspective of what your client experiences, how your team performs, and how you can proactively support your team’s delivery to be at 85%, 90%, and eventually 95% proficiency like you. Remember, patience is required here but the great thing is your team will be able to excel in their performance and be able to constantly do so over time with the proper investment of training, empathy, and optimism in their growth. 
You facilitate this growth by how you lead.

Fuel Others

Heroic Leaders understand that the team is running a never-ending marathon because our aim is long-term, consistent performance.

We must therefore take proactive actions to fuel the team and give them the electrolytes and support for the endless marathon.

Here we focus on the health of the team, creating new leaders, and inspiring your team to grow personally and professionally.

The health of the team is based on both the mental environment you’re helping create with the team, as you set the stage, and also the workload.

By checking in on how your team is doing, you can also identify how you might help them balance their workload more effectively or remove unnecessary tasks that were once a priority and now aren’t.
If you need a step-by-step to optimize your team’s day, go through the 80/20 Journal For Digital Teams and consider grabbing your team physical copies to align their daily focus on what matters most in their life and in business.

In addition, also empower your team with training and decision-making, so they can solve problems proactively without always relying on you.

One way to do this is to practice 3 Solutions Coaching, where when someone asks you a question, you set the expectation that they come to the table with 3 possible solutions to their own question.

That will allow them to think for themselves and also show you at what level they are in their decision-making skills. When you provide the answer for them, coach them on why you chose your answer. 

Over time with repetition, you’ll be able to have the team able to make the best decisions on their own. 

It does take time, but the payoff is definitely worth it. You’ll soon find your team making better decisions than you over time, and that’s a good thing!

Your Lasting Influence

As you work to fuel your future leaders, as a Heroic Leader, you must place importance on making your development opportunities interactions and not just transactions. 

Take a keen interest in your future leaders and also identify what they care about. The influence you have on your future leaders will determine the legacy you leave with them and the leadership qualities they may carry over the next 20-30 years.

Reflect on that.
The work you do today does have a lasting impact.

Becoming a Heroic Leader

Becoming a Heroic Leader isn’t complex nor difficult. It just takes intention, dedication and practice over time.

As you start to put these habits into practice, I’d like to give you a mental model that will serve you as you apply these habits in your leadership. This model will also help you as you implement anything new in your life and business.

We’ll be using the Fibonacci series of numbers, which can also be found in nature as the golden ratio, in order to give us a practical perspective when we apply something new in our lives.

When you go to first apply the new learnings, you make take up to 34 attempts before you see any measurable or observable progress.

That’s normal, keep on going.

In your 2nd round, it may take you 21 attempts to see progress. In your 3rd go-round, 13 attempts, 4th, 8, 5th, 5… and so until you get to what works consistently for you.
Lesson: Don’t quit early. You can and will succeed through consistency.

Below you will find 9 simple questions and prompts to get you to create a plan to practice being a Heroic Leader.

It’s an honor to be a small part of your journey. 

Do Good Work, 


Know someone that needs to read this? Consider sharing this with them. You may be the catalyst that opens them up to a new way of operating their business and experiencing life. 

Becoming a Heroic Leader: Simple Exercise


On a blank journal entry or in your note app, answer the following 9 questions on your own. If you are doing this with your team, pair your team in groups of 2 to support each other in walking through the questions.
This exercise can take 15-45 minutes depending on the depth of the conversation you have with yourself or with your team.

Becoming Heroic

  1. Write out 5 ways you can adapt to become or improve upon being a Heroic Leader. Detail out when and how you will implement them.

  2. How do you define the way you do business?

  3. What behaviors do you want your team to exhibit and learn from you? How will you teach them?

  4. List out the key feedback loops and data you need to monitor in order to keep the pulse of your company.

  5. Who will you go-to for a sanity check & advice?

  6. Who are the current and future leaders in your company and how are you nurturing their growth?

  7. What are the minimum levels of acceptability in every key area of your company?

  8. How will you facilitate movement in your company?

  9. Check your daily time blocks and detail when and where you will hold your team meetings. You control your calendar. Try to limit others from manipulating your time blocks.

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