What does it mean to be an intentional leader? Most articles would tell you it’s about aligning your inputs to the outputs you desire. Most articles give advice about modeling the behaviors we seek in others. Which is great! But my humble opinion is that most leaders need to lay the groundwork for their behaviors by looking inwards and asking some important questions. This is the best way to truly begin the challenging journey of intentional leadership.



As my good amigo, Daniel Harkavy, says in his amazing book Living Forward (co-authored with Michael Hyatt):

Self-leadership precedes team leadership. 

Here are some questions to ask yourself (fair warning: this may sting a little):


1) Do I live day-to-day, or do I have a plan and vision I rigorously follow for my life?

Average leaders focus on ROI. They hide in the safety of what they’re supposed to do day-to-day. Often, they have a hectic, fast-moving schedule that exudes, “I’m busy and important because my calendar is full and back-to-back.”

Intentional leaders do value ROI, yet place higher importance on ROL–Return on Life. They are secure in telling you “no” in a polite and graceful manner if they can’t serve you since it may be disruptive towards their long-term vision.


2) Do I want to be the hero, or do I channel all my energy into my team?

Average leaders believe they’re better than the people they lead. I understand that may sound harsh, but unfortunately it’s true for many. There’s an ego that shows up in their desire to be known as “the leader” and they silently enjoy when people know their status and title.

Intentional leaders know the dreams and the gifts of their people. They celebrate the progress of those dreams and leverage their teams’ gifts with every opportunity. They often broadcast those gifts above theirs to the entire community.


3) Do I look for things that went wrong, or do I catch people doing things right?

Average leaders are still hard-wired to look for mistakes. They are well-intended but this is where they invest too much of their time–finding the source of blame. They fixate on errors or misses, they keep score. They believe in the alpha myth that celebration and kindness is soft; or worse, unnecessary.

Intentional leaders have learned the immense power of recognition as well as the joy it brings to the people they catch doing the right things. The joy of their team makes leaders’ hearts sing! They are practicing the most powerful emotion on the planet: gratitude. They see the people they lead for who they are and who they want to become, not the little mistakes or failures.


4) Do I long to be the center of attention, or do I have the courage to take a quiet position in the back?

Average leaders seek to please the crowd. They crave for a post to go viral or they place too great an emphasis on social media “likes” or online ratings. There’s often an inner desire to be known for fame. Self-promotion becomes its own reward.

Intentional leaders share their wisdom with one purpose–to give. What matters to them is to align their leadership values to their actions for the benefit of others. They unapologetically live within their boundaries and respect that their approach to leading won’t appeal to everyone. They know we all struggle. They take tremendous pride putting the people they lead on the main stage instead of themselves.


5) Do I compete against others, or do I celebrate the good others are doing?

Again, average leaders keep score. They want to win for the sake of saying they are “numero uno.” Being known as the best, the biggest, or the wealthiest drives their purpose. This often shows up in their quest for status. You can usually sense this in a conversation because they will ask you very few questions about your story. Telling theirs is more important.

Intentional leaders believe in the power of simplicity and humility. They know their purpose and how they want their story to matter. They know who they’re helping and this gives them fulfillment. Intentional leaders are an unrelenting champion for the Underdog and cheer in the front row till they lose their voice when the Underdog pulls off an upset! They ask you a lot of questions about what you want and why you want it. When they tell their story, it comes from a place of wanting to help you better understand your own story.


We All Struggle

We must first go through suffering, pain, and struggle to get to wisdom. Wherever you may be on your journey and transformation, I hope you ask yourself these questions, and you’re honest in your answers. In time your reflections will become more clear so you can get the energy you need on your climb. I understand all too well how steep this mountain can be and how long it can feel placing one foot in front of the other.

Students of struggle confront their reality and practice reflection. They make hard changes and know the climb on this mountain towards intentionality is steep but they’re not alone. Imagine the possibilities when we all extend a hand to one another as we stray off the path.

Hail the Underdogs!



  1. Nathan Regier

    These are all fantastic guides. I particularly appreciate #5 since my personality is naturally competitive, so I have to be very intentional to apply what you say, Bobby. I’m working to foster a culture in our company where we balance individual achievements (for those who thrive on that), with celebrating wins for the good of the whole as well. One of my employees recently said, “All I want to know is if you have my back.” That’s a testament to your message.

    • Bobby Herrera

      Love this, Nate! Keep doing good!


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