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Interview Project People & Leadership

Isa Grimes Interview

I didn’t sit down with Isa Grimes to hear a title talk. I sat down with him to hear how he thinks, how he leads, what his 20s taught him, and what actually matters once life stops being theoretical.

Format

Conversation / Interview

Focus

Leadership, People, Your 20s

Why I kept it

perspective over title

Why I Asked for This Interview

Before we even started, I told him something that mattered to me: I did not want to interview Isa Grimes the CMO. I wanted Isa as a person. I wanted the mentality, the leadership, the teaching, the thought process, and the parts of his life that shaped the rest.

Anybody can talk about a title. That was not the interesting part to me.

I wanted to know what he believed after living enough life for the answers to cost something. I wanted to know what he would tell somebody who is still early, still uncertain, and still trying to build a real life instead of chasing a polished image of one.

What Actually Hit

Your 20s are for exposure, not certainty

When I asked him what he would tell a person uncertain about the future, he did not give me some polished five-step plan. He said the first five years after graduation should be full of different roles, industries, and people.

That mattered to me because it kills the lie that you are supposed to know everything at 22.

His answer was basically this: most people in their 20s do not know yet, so stop pretending certainty is the goal. Get exposure instead. Put yourself in different rooms. Learn different industries. Learn different communication styles. Figure out what actually fits you by living more of life, not less of it.

“The first 5 years of graduation, you have to be in as many different roles and industries and around people as possible.”

Do not rush the route just because you are scared of falling behind

When I pushed him on what advice he would give his younger self to become who he is now, but quicker, I expected some answer about efficiency.

That is not what he gave me.

He basically said he would not change the route just to get there faster. He talked about enjoying his 20s, living through things, making mistakes, and becoming the kind of person who could actually carry the role later.

That was one of the strongest answers in the whole interview for me, because it rejected the fake obsession with speed. He did not talk like someone desperate to erase the years that formed him. He talked like someone who understood that the route mattered because it made him ready.

“During your 20s, have fun. That’s what it’s for. But at the same time, expose yourself to different opportunities that are out there.”

“I wouldn’t change it at all.”

People beat process

When I asked him what mattered more in his growth — understanding the organization or knowing how to manage people — he answered quickly: people.

That answer carried the whole page.

He made it clear that a lot of organizational knowledge can be learned. What is harder to fake is knowing how to deal with people well. Knowing what makes someone tick. Knowing how to read strengths, weaknesses, timing, ego, confidence, communication style, and what someone actually needs from you.

That is what separates a title from actual leadership.

“People, right. Most people don’t know how to manage people.”

Favoritism ruins leadership

One of the cleanest answers in the interview came when I asked what he learned from people by watching how not to be.

He did not dodge. He said favoritism.

I liked that because it was concrete. Not some vague answer about “poor leadership.” Favoritism. Giving people room, credit, or movement because you like them, not because they are right for the moment. Once you do that, you poison the room. You make trust thinner. You make standards weaker. You make people feel the hierarchy before they feel the purpose.

“I see a lot of people have favoritism.”

Build a round table, not a throne

The best leadership image he gave me was not corporate at all. It was a round table.

He talked about leadership like King Arthur, the Justice League, a room where everybody brings a different angle and different value. The leader still has to make the final call, but the room is not supposed to revolve around one ego.

That answer worked because it matched how he talked the whole time. He did not sound like someone obsessed with status. He sounded like someone who actually believes that people matter, no matter where they sit.

“Everyone is equal. I don’t care if you’re the garbage man. I don’t care if you’re a CMO.”

The most human answer had nothing to do with work

When I asked him what experience taught him something real about leadership, he did not go straight to a job. He went to marriage, growing up, and realizing life was not just about him.

That was probably the most human answer in the interview.

The way I took it was simple: leadership is shallow if it only exists at work. If you still move through life like your choices only affect you, then the title does not mean much. The real shift came when he started asking a harder question: not “am I technically wrong?” but “what does this do to the other person?”

That answer had more leadership in it than most leadership answers do.

Leadership starts before the title does

I also liked what he said about who he used to be as an employee.

He admitted that earlier in his career he was more of a blind doer. He was getting tasks done without really understanding the bigger meaning behind them. Then he started changing the way he carried himself. He started dressing like he wanted to lead. Looking for stretch work. Shadowing other functions. Reading more. Asking bigger questions. Acting like the next role before he had it.

That answer mattered because too many people talk about leadership like it begins the day they get authority. It does not. It starts way earlier than that — in how you learn, how you carry yourself, what extra weight you take on, and whether people can trust you before you are in charge of anything.

Roots. Trees. Forest.

“There’s three levels in life: roots, trees, and forest.”

This was one of the best frameworks in the entire conversation.

He said life has three levels: roots, trees, and forest.

Sometimes you are down in the roots doing the immediate work. Sometimes you are in the trees looking at the next level up. Sometimes you are in the forest asking where all of this is going. What I liked is that he did not present those like fixed ranks. He treated them like positions you move through depending on the situation.

That made the idea useful instead of decorative.

No one is omnipresent

The introspection part of the interview was strong because it was honest about trade-offs.

He basically said you cannot be everywhere for everyone. You are going to give time to one thing and take time from another. You are going to disappoint somebody. You are going to make choices that help one responsibility and cost another one.

That is real life.

What mattered was not pretending balance is easy. What mattered was knowing that trade-offs are unavoidable and still trying to make the right call for the people and responsibilities that matter most in that moment.

“No one is omnipresent.”

“Spend time with the ones you love.”

The Part I Respected Most

What I respected most about this interview was that he did not try to sound perfect.

He did not sell me a shortcut. He did not talk like everything in life can be optimized into a clean line. He talked like someone who had actually lived enough to know that some parts of life are there to shape you, not just speed you up.

That is why I wanted Isa the person, not Isa the title.

The title is impressive. Fine. But that was never the best part of the interview. The best part was hearing someone say, in different ways, that people matter, timing matters, experience matters, and becoming the right person matters more than trying to arrive early just so you can say you did.

Selected Lines

These are the lines I would keep even if the rest of the page disappeared.

“The first 5 years of graduation, you have to be in as many different roles and industries and around people as possible.”

“During your 20s, have fun. That’s what it’s for. But at the same time, expose yourself to different opportunities that are out there.”

“I wouldn’t change it at all.”

“People, right. Most people don’t know how to manage people.”

“I see a lot of people have favoritism.”

“Everyone is equal. I don’t care if you’re the garbage man. I don’t care if you’re a CMO.”

“There’s three levels in life: roots, trees, and forest.”

“Spend time with the ones you love.”

Why I Kept This

I kept this interview because it says more than “be a leader” ever could.

It says get around more people. Learn earlier. Pay attention. Stop worshipping titles. Build a real support system. Be careful who you keep close. Do not rush your life just because somebody else looks ahead of you. Learn how to deal with people before you start acting like you know how to lead them.

That is a lot more useful to me than another polished success story.

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