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Career Strategy

"Why Did You Leave?" — Transform Your Greatest Vulnerability Into Unstoppable Leverage

By Jacob Warwick,

Published on Jan 30, 2025   —   11 min read

"Why did you leave?

Four words that make even seasoned executives sweat.

Even as a (mostly) objective confidant for thousands of executives, I've had to pull on my best mud boots to trudge through the sticky situations leaders delicately try to explain when looking for their next opportunity.

Sometimes, you're frustrated with hostile working conditions.

Sometimes, the performance expectations are untenable.

Sometimes, you are the one who created hostile working conditions and untenable expectations, and you're running from your self-inflicted mess.

Sometimes, it's just time.

Then there are the times when non-performance factors come into play, such as a spouse taking a new role or a lifestyle change to live closer to family. Babies, children's education, work visas, restructurings, aging parents, sabbaticals—you name it.

Either way, organizations and executives fall out of alignment all the time.

So why is it so hard to answer questions about why you want to leave or why your last role didn't work out?

Own Your Story, Control Outcomes

After engineering power dynamics in your first 90 seconds and mastering the "what's next?" question to demonstrate strategic vision, you might think explaining a transition would be straightforward.

But your answer is particularly treacherous because, more often, you will reveal more about your executive presence than the actual circumstances of your departure.

I've noticed that the general perception and most career advice regarding executive-level interviewing is incorrect.

While it's not wrong to be confident and optimistic about interviewing or to prepare your ass off—the buck doesn't stop there.

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