Disclaimer: This story happened before the COVID-19 pandemic.

Herrera kids at horseback riding lessons, summer 2020

2/3 of my kids at horseback riding lessons, circa summer 2020

The Moment

I recently experienced a cool Dad moment.

It was early morning before school and my 2 boys had just come downstairs after getting ready. I’m the breakfast guy, so I was prepping the morning’s grub while Mom made lunch. For parents, this time of the morning is unpredictable at best, so we set our expectations accordingly. You never know if the kids are going to be happy, cranky, or as often happens in our house, doing somersaults off the couch.

My oldest, Santino, was in a great mood and yelled to me, “Dad, I’m on #462 on the Triceratops picture!” He loves dot-to-dot picture books and was really excited about his new, dinosaur-themed version.

I’m doing my best version of Iron Chef and his little brother, Griffith, was playing in our entry way, testing the boundaries with a football. I noticed Griffith walk to the table where Santino was happily connecting dots. He watched quietly for a moment, and Santino encouraged him to start the new book he’d recently talked Mom into buying for him.

Reluctantly, Griff opened his book and Santino excitedly says, “Awesome Griff! Find #1 then connect it to the next one!”

This was Griff’s first time so moments later, he moaned in frustration and wanted to stop. But Santino leaned over and said, “you already did 10, Griff! I see 11…you can find it!” Griff spotted 11 and yelled enthusiastically, “There it is! There’s 12, too!”

This continued for several minutes till I served the hungry boys and their little sister French toast and bacon. Griffith excitedly told me how high he got and was laughing with his big brother about how cool and how much fun dot-to-dot books are!

The Lesson–The Gift

Trying something new is scary for all of us. And it’s immensely frustrating for the people we lead if we don’t give them positive encouragement as they’re trying these new things.

In Chapter 7 of The Gift of Struggle, The T-Chart, I share a gut-wrenching lesson I learned when Santino was a very young boy. It stopped me in my tracks and changed my mindset in how I needed to give him direction. I share in the book how I transferred that life-changing lesson to anyone I lead.

And the story I shared above highlights the invisible forces behind my transformation as a leader during that gut-wrenching time of my journey: courage, encouragement, and trust.

  1. Courage: Like Griffith, I first had to step into the discomfort of changing and trying something new.
  2. Encouragement: Struggle is always a prequel to transformation–it’s hard. When Griff’s courage was running low and he was truly struggling, Santino was there to encourage him. I surround myself with people who did and will do the same for me.
  3. Trust: Griff felt safe, and he trusted his big brother enough to take the leap himself, and accept Santino’s encouragement. This force speaks for itself.

The Sharing

When Santino first started his dot-to-dot books, his mother and I modeled the same behavior he exemplified with his younger brother. When he was stuck, we relied on these 3 invisible forces to guide him while also using the ‘Go’ commands I highlight in the book. In other words, we honed our energy in what he could do versus what he couldn’t.

Too often in leadership, there is a disproportionate focus on the negative–on the things our people shouldn’t do. I understand first-hand how difficult that is. The problem? When we focus too heavily on the “should nots,” the leaders we’re guiding will do the same for those they lead.

The example of my family may be exaggerated and you’d expect those forces in a family setting. But that’s precisely why I use it–the people we lead are like family.

Wouldn’t you agree they deserve that same care? Kindness and compassion are exceptional lessons we can practice more often.

The Reflection

Strong leaders intentionally self-assess the impact of these forces by asking themselves these questions:

  1. How am I modeling courage and curiosity with my team?
  2. Do the directions I give my people make them feel positive and encouraged?
  3. How are my interactions building trust with my team?

The most exciting part of this story is that we get to choose our impact in every relationship and how many of these forces we ignite in others. If 2 rambunctious boys can figure this out, imagine the possibilities for your leadership journey.

Hail the Underdogs!


  1. Brandon Dudley

    More “could do’s” and less “should nots”…thank you for the reminder. 🙏

    We miss y’all and hope you all are doing well.

    • Bobby Herrera

      Thanks Brandon! Hope you’re doing well and had a great holiday!

  2. John Jones

    Great story and lesson Bobby

    • Bobby Herrera

      Hail the Underdog, John!

  3. George Gahr

    Great share Bobby – simple yet effective. A lot of training and development happening on my new team right now and very easy to point out what isn’t being done well….critical to encourage the newbies and find ways to build trust…..because as we discussed, that’s where you generate your speed!

    • Bobby Herrera

      We’ve always gotta build trust! Glad to hear you’re encouraging your team and guiding them to success!


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