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Level Up Newsletter

"Am I Just a Loser?"

How senior candidates can identify the subtle signals holding them back, strengthen executive presence, and stop finishing second

Ethan Evans's avatar
Jason P. Yoong's avatar
Ethan Evans and Jason P. Yoong
Jul 30, 2026
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Hi, it’s Ethan & Jason from Level Up: Make career breakthroughs with AI-proof leadership skills.

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Today’s Level Up: Inside Executive Coaching (your candid look inside real executive coaching conversations) explores why qualified leaders keep finishing second, and how to identify the subtle, addressable causes that separate a viable candidate from the inevitable one.

This conversation examines how confidence and executive presence shape the increasingly thin margins that determine who gets chosen for bigger roles.

The Situation

I spoke with “Ram,” a Senior Consultant at a healthcare technology organization who reached a plateau in his career.

After years of growth, he had set his sights on Director and CIO-level roles.

His resume was strong, and he interviewed well enough to consistently reach the final round in many application processes. In several cases, he even had senior executives advocating for him behind the scenes.

Yet, the outcome was always the same.

He finished second.

So close with nothing to show for it.

This happened 11 times in a row.

By the time we spoke, he was not questioning his qualifications anymore.

He knew that he was qualified to get all of those jobs.

He had begun to question himself.

Was there something wrong with him that made him so repeatedly dismissible?

The Question

Here is how the conversation with Ram went:

“I know this sounds dramatic, but... what is wrong with me?

Am I unable to get the jobs I want?

Am I just a total loser?”

This made me smile.

“I don’t think you are a loser, but I understand why you’d feel that way right now. Eleven final-round interviews is enough data that I don’t think this is random anymore. I think something is going on. The good news is that if there’s a pattern, there’s probably an addressable cause.”

I deliberately used the phrase addressable cause.

This is to communicate the idea that what he is experiencing is not a character flaw or a permanent condition. Rather it is a behavior to identify and improve.

Stop Blaming Cosmic Forces

As we talked, Ram admitted that after so many disappointments, it had begun to feel like there was some kind of cosmic force working against him.

This is exactly the opposite of looking to identify and improve a specific behavior or element of yourself, so I stopped him there.

“You’re not allowed to blame cosmic forces.”

He laughed.

“Seriously,” I continued. “Let’s take God, fate, luck, and the universe completely off the table. If you had to explain these eleven interviews using only things you can influence, your executive presence, your confidence, your communication, your interview style, your relationships — what would your theory be?”

He thought for a moment.

“I think I become the viable candidate... but not the inevitable candidate. I’m someone they would hire, but not the person they feel like they have to hire.”

I fully agreed.

This was a great realization for him to come to.

Now we could start working on the things that would turn him into the candidate that companies “have” to hire.

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