The Right Way to Explain Career Setbacks

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Everyone experiences loss—even executives. But we always gravitate toward the wins.

Especially if your career intel comes courtesy of the fluff-pastry-filled humble brag capital of the world—LinkedIn.  

In the often context devoid rat race to become the next influential business guru, the bombardment of social media deception tends to camouflage reality.

Many executives are big-time losers. But those with the most rewarding careers are resilient—or relentlessly stubborn. 

As much as I’d like to be the greatest of all time in the coaching arena, having you believe that all my clients were always winning would be misleading. 

Lately, I have worked with a handful of tough defeats.

I’ll elaborate. 

Experiencing Career Loss

2023 has not been sunshine and rainbows for many. The market has been a cutthroat bloodbath, especially in tech. 

You may have experienced a dose of disappointment yourself. Hopefully, you haven’t. You probably have a friend who has. Hug them for me.

Here are a handful of pesky losses of late.  

Client #1 – A highly specialized executive with nearly eight years paying their dues at a seven billion dollar software company — was passed over for a career-defining promotion. 

What’s worse? The internal candidate who won the role had no previous ‘specialized’ experience but had a prior bonding experience with the Chief Operating Officer from two decades back. 

Is it time to polish the resume? 

Perhaps it’s not what you know but who you know.

Client #2 – A younger ‘force multiplier’ performed as the acting CEO and #2 to the top position for 18 months. They were primed to lead the succession and a more innovative future in an antiquated industry. 

Growing to the CEO role is why they took the position in the first place.

After months of preparation and negotiation, they were eliminated for an older, status quo external hire—the opposite of what the board and leaders repeatedly said they wanted. 

Should they stay, or should they go?

Sometimes executives talk about wanting change, but when the opportunity comes to fruition, they revert to the conservative stodginess of before. 

Client #3 – A seasoned senior executive spent one year carefully vetting organizations and made an impressive transition into a new industry. They accomplished a rare career rebirth without sacrificing compensation or undermining their seniority.  

They won the deal and negotiated a notable increase in compensation—but they were dismissed six months in (after completing a companywide reduction in force). 

Do over?

When others carry our basket full of eggs, we’re always at risk of getting yolk blasted on our faces.  

Rebounding From Career Loss

Sometimes things go awry, and it’s your fault because you screwed up. I suspect these losses are easier to bounce back from because we can learn from what went wrong and adjust. 

Other times, it’s not your fault, and many thoughts may bounce around your noggin.

  • I’m cursed!
  • I quit!
  • Do other people deal with this?
  • How do I explain this crap?
  • Why am I attracted to masochism?

Regardless of whether it was your fault, it is your responsibility to endure. 

You knew the risks, and you took your shot. Coming up empty occasionally should keep your spirit intact, right? Ultimately, as an executive, it is your job to lead through the good and the bad, eh? 

That includes the mental fortitude to overcome yourself. 

I’m not suggesting that you won’t navigate the five stages of grief in one manner or another. Instead, I offer a not-so-subtle reminder of what you signed up for in the first place. 

You will endure.

Communicating Career Loss

I’m often asked how to communicate challenging career situations. It’s an acquired skill.

I used to be proud of how I could sling disappointing career bullshit into dialogue that resembled something positive and heroic. 

It’s not what you say; it’s how you say it.

Now I’m not so sure. 

Instead of weaving fabrication, I concentrate on how to help clients approach executive communication with a heaping plate of humility and ownership. 

When you play the victim, people feel sorry for you. 

But when you play the hero, people rise to fight alongside you. 

When faced with communicating challenging situations, I advise that you do so with candor and take ownership of what you can—but don’t throw stones. 

You don’t need to be perfect. 

For example. 


“Why did you get passed over for the promotion?” 


“This is still difficult for me to talk about. Initially, I felt angry that I was passed over—hell, almost jealous and frustrated that I didn’t have what the other executive had. Maybe you’ve felt this way too. Then, I began to think about what I could improve. It was a wake-up call to address my executive presence and communication style in critical meetings. I’m mindful of how….” 

Take a moment to pause and breathe before diving right in to answer tough questions. It’s okay to proceed slowly. 

Share where you may have gone wrong, even if your internal emotional response was disappointing, and be honest. 

Mindful and honest responses are better than a shifty, stuttery approach. They certainly do better than pointing a finger at anyone other than yourself. 

Bonus points if you can create a shared identity with your audience. 

“I bet you’ve experienced this before.”

You see, you and I aren’t that different. We all lose.

When you can work through sharing your losses with integrity, you invite your counterpart to participate

Getting it all off your chest with honesty is even therapeutic. 

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