Ask A CEO: What Does It Take To Be A Leader?


Bobby Herrera The Gift of Struggle Behind the Scenes


What happens when you sit down and ask a CEO brutally honest questions about what it takes to be a successful leader? Hopefully, you’ll get brutally honest answers, and when you do, let’s hope you’ve got a journal handy to take notes. Learning directly from experienced leaders is a rare and valuable opportunity, and you’ll likely hear something you want to implement with team members, utilize in your decision-making, or something to remind yourself when a hard day comes.

In this interview, you’ll learn about the different leadership qualities and leadership skills that effective leaders use from Bobby Herrera—CEO of Populus Group and author of The Gift of Struggle. All leaders, regardless of leadership role, will benefit from the topics that Bobby covers. Whether you’re leading a Fortune 500 company, non-profit, tech startup, or local community, there’s something here for you.

Heads up—we suggest you get that notepad out for section 5. Feel free to use the quick links below to jump to each section!

Table of contents:
  1. The Key Points of Leadership and Why It Matters.
  2. Learning From Leadership Mistakes.
  3. How to Become a Better Leader.
  4. Leading a Team: Questions to Ask, Problem-solving, and Priorities!
  5. Self-Evaluation: The One Question to Ask Yourself


1) The Key Points of Leadership and Why it Matters.

“People want to get the life they dream of. Unfortunately, many drift and allow distractions to dilute their potential. They get distracted and need guidance and encouragement. Great leaders help people take control of their story and live the life of meaning they want.”

– Bobby Herrera


Why is leadership something people should aspire towards?  

If you want to have a life of fulfillment and meaning, then becoming a leader is the right choice for you. Few things will fill your heart with more joy than helping someone achieve something meaningful for themselves and their family.


Is leadership for everyone? 

No, and that’s okay. Just like parenting or joining the military, it isn’t for everyone. The unvarnished truth is that it’s better for everyone if people who don’t want to selflessly lead others choose to follow instead. You must have it in your heart to serve others. Great leadership is simple: you must GIVE more than you TAKE. Simple doesn’t make it easy; effective leadership is hard work. I encourage others to admit whether the steep climb of leadership is for them. If it’s not, you’re still helping those around you by being humble.


What can people gain by becoming a leader?

At the end of our story, we want to know that we mattered. Leadership helps you check that important box. Sure, there are opportunities for more financial gain and exposure, but in the end, those pale in comparison to living a life of meaning and impact.

People want to get the life of their dreams. Unfortunately, many drift and allow distractions to dilute their potential. They get distracted and need guidance and encouragement. Great leaders help people take control of their story and live the life of meaning they want.


What is the cost of being a bad leader?

How much would you give to make sure the people you love didn’t hurt inside? You cannot measure the negative impact of bad leadership because the pain is too great. It’s not only financial numbers that are hurt by bad leadership, it’s also lives. Bad leadership ripples beyond the interaction of the leader and the person being led. It impacts lives and relationships in the home after the workday ends. It amplifies the narrative of self-doubt that people play in their head. People are human, and we get one act at life–it’s too important to allow a bad leader to steal that joy from anyone.

Parallel with this strong opinion is the fact that many believe the alpha-myth that good leadership is synonymous with perfection. The opposite is true. Great leaders are humble, and they openly own their mistakes. They are students and remain curious to learn from leaders who are better than themselves. Bad leaders won’t model this type of behavior because their ego gets in the way of their ability to be vulnerable.


What do people need to do to become a leader?

A ‘permission to play’ requirement is a strong desire to help others. To be a great leader you must be willing to be highly involved and hold your people to that high standard. To help aspiring leaders understand the essence of what I mean, I often ask them to name the one or two people who have had the most significant influence in their life. They tend to name a parent, a coach, a teacher, a friend, or mentor who was very involved while always telling them the truth of what they needed to hear. You can quickly name yours too.

A dear mentor taught me many years ago that as a leader, I am not allowed to change anyone else before I change myself. People do what people see, and they can sniff out bad leadership from a mile away. If you’re kind, they will model that.


2) Learning From Leadership Mistakes.


What is something you know now that you wish you’d known when you began your leadership journey?

That kindness and gratitude are skills that must be developed to be a great leader. Both are critical and overlooked skills that I recommend aspiring leaders start developing.

Kindness changed my life, and gratitude is the most powerful emotion on the planet. When you combine these two forces you create a magic that ignites potential in others and creates fulfillment for everyone.


What would you say to the person just starting out on their leadership journey?

I would ask them to consider two universal truths then decide what course they will take based on the answers to the following questions:

1) We all struggle. Every struggle teaches us something–that’s the gift. Will you consider making struggle your friend and viewing it as a source of empowerment?

2) You get one act at life. Do you want your story to matter?

Leadership is sharing those gifts to help those you are responsible for and love. You get to choose from this point on–I’m here to share my gifts if you believe they will help you. All Hail the Underdogs!



3) How to Become a Better Leader.


What character traits are associated with becoming a better leader?

Trust is the most important asset any leader will own. You must develop the type of character that builds trust. You intuitively know what these behaviors are because they’re inherently important to you. I’ll share some examples so you can harness your courage and build your own leadership confidence. Simply focus and do what you know you should be doing for those you lead:

1) Always tell the truth despite the circumstances. People want the truth and trust can be damaged beyond repair if a leader violates trust.

2) One of the best ways to build trust is to become more vulnerable. This is scary and overwhelming to many people, so they choose to stay quiet. It was one of the biggest struggles I had to overcome. I held my fears and my story in until my pipes burst. I learned the hard way that it was holding back the potential of the people I was leading. I’ve since learned that was selfish of me.

3) Transparency—people hate surprises unless they are good ones.

4) Listen more than you speak. People have a strong desire to feel heard.

5) Give people the benefit of the doubt—assume the good in people. Unfortunately, the opposite is modeled more often because it’s easier.



4) Leading A Team: Questions to Ask, Problem-solving, and Priorities!


Are there personal habits or practical actions that leaders should make a priority in their lives?

Great leaders put their oxygen masks on first. Leadership is about impact—the bigger the impact made on yourself, the bigger the impact you make on others.


What is the role of struggle or failure in the development of a leader?

Struggle is the most honest and revealing measure of progress for anyone who wants to lead. You must go through struggle, pain, and suffering before you get to wisdom. Struggle can stop us in our tracks. It can impact our sense of who we are and our self-esteem in a deep way. But I think there’s a lot to be gained by reflecting on your struggles, not running from them. I learned this the hard way. If you’re curious to learn more, check out my book The Gift of Struggle.

Everything you do well today started with struggle. Imagine the possibilities when you earnestly start to study what struggle’s already taught you?


Questions Leaders Should Ask Their Teams

The best leaders are in the mindset that they can’t do it alone and that they can’t do everything. They view their teams as people who have more important lives outside of work first and foremost. They also don’t buy into the dogma that “the leadership chain is the IQ chain.” True leaders are open and passionate about new ideas their teams suggest. These are the types of questions leaders should ask themselves when they connect with their teams:

1) What are their biggest dreams and how can I help them get there?

2) What’s most important in their lives and how can I help them do more of that?

3) How can I help them become a better version of themselves?

4) What type of things give them energy and how can I best utilize their strengths?

5) What are they doing well so I can show them how much I value their effort?

There are tons of classic cultural examples of what a “good leader” looks like. Some are helpful, some are not. Is there a specific “leadership style” that you associate with being a good leader?

Leaders come in all shapes, sizes, and, personalities. We need all of these wonderful differences. What must be the same is the common desire to serve others first. Leadership is about impact—how you make the impact is situational to the person. That’s hard for literal thinkers to grasp–I don’t have an easy answer for someone who is looking for a “what to do when” checklist.

For example, I used to think that being an outgoing and loud extrovert was required for leadership. But now I’ve observed many powerful, introverted leaders. Lions don’t need to roar to show others they’re a lion.


How do good leaders approach problem-solving?

Never alone and always together. They will ask themselves questions like:

1) Who knows more than me on this problem?

2) Who else’s perspective should we get?

3) Who do we know that has solved the problem we’re having?

They also never do the following:

1) Blame

2) Point fingers

3) Deflect responsibility

4) Assume bad intent

5) Stop at the symptom level—they drill deep to the root cause and start repairs there.



5) The One Self Evaluation Question Leaders Should Ask.

The first step to becoming a leader is rigorously working towards becoming the person you imagine inside. Ask yourself, “who am I becoming?” It’s the single most important question in leadership because leadership is an inside job. I would recommend you take 3 simple steps to begin this journey:


1) Take a brutally honest inventory of who you are today by self-assessing yourself on a scale of 1 – 10 with these pointed questions. Tell yourself the unvarnished truth and applaud yourself in areas where you excel:

A) Am I living with purpose? ___

B) Am I kind? __

C) How patient am I? ___

D) Do I give others the benefit of the doubt?  ___

E) How well do I intentionally build trust with others?   ____

F) Do I rigorously apply what I read and study?

G) Do I catch others doing things right and recognize them?

H) Do I take responsibility for all my shortcomings?

I) Am I vulnerable with others?


2) Then ask 3-5 people you trust the same direct questions about how you impact them and others. Only pick those who will tell you the kind truth. 

Note: You must make this a safe conversation for them by promising up front that all you will say is “Thank you.”  


3) Finally, draw your mountain. Look into the future and write down attributes and characteristics to this question, “Who do I want to become?” 

I must elaborate on Step 3. You’ll never stake your flag on the peak of this summit. To become a great leader you must choose to be on this unrealistic and infinite climb. The answers to your questions in 1 and 2 will highlight for you the areas that you will always need to strengthen and work on to build better long term habits. Be patient and persistent; it will take time to show incremental improvements towards becoming compassionate towards others.

In my experience, aspiring leaders fail because they don’t build their development stamina. They start fast, then drift. They take on too much at first, then quit. I was inconsistent and all over the map until I implemented simple and palatable routines into my life to become a better person. Examples include; 5 minutes daily to complete my gratitude journal, a daily short reading block, 10-minute blocks to call and recognize others and write thank you notes, exercise blocks, a monthly flush list to write down all my worries and questions, etc.



What does it take to be a leader? A commitment to integrating the principles outlined above. Without these critical first steps, you can still become a good leader…but your chances to become a great one reduces drastically. The best part is you get to choose.


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