A witty column about the genuine, emotional, and humorous exploits of coaching elite executives.


Why Didn’t Your Last Role Work Out?

interviewing job search strategy narrative development realization
Interviewing Challenges: Why Didn’t Your Last Role Work?

Few questions spark the pain train and elicit a nerve-rattling duplicitous response quite like asking about why you’re leaving a current role (or why you got shit-canned 5 months ago and are still struggling to land on your feet). 

Even as an objective confidant for hundreds of executives, I have to pull my best mud boots on to trudge through the sticky situations that leaders delicately try their best to explain when looking for a new role. 

Sometimes they’re frustrated with hostile working conditions, sometimes the performance expectations are untenable—and sometimes they are the ones that create the hostile working conditions and build the untenable expectations and need to leave. 

Then there are the times non-performance factors come into play, such as a spouse taking a new role or a lifestyle change to live closer to family. But more often an organization and an executive have simply fallen out of alignment and a change is warranted.

There are countless reasons that can factor into a career transition. So why is it so hard to answer questions about why you want to leave or why didn’t your last role work out?

Don’t Look At My Failure.

I’ve noticed that the general perception about interviewing is incorrect.

It’s not wrong to be optimistic about interviewing and keeping interview conversations forward-thinking, positive, and about crushing goals— but the buck doesn’t stop there.

The purpose of interviewing is to understand. And that means the good and the bad, for the employer and the candidate. Wouldn’t you like to know what you’re getting yourself into?

If we don’t take the time to grieve a prior role, or more importantly, get clarity around why it’s no longer working and have confidence about what’s next, we do our future selves a disservice and are often caught off guard when challenged about it.

Is it because we’re our hardest critics and feel shame when we’re not as successful as we think we should be? Is change synonymous with failure? 

Sugarcoating Is A Weakness.

If you read, You’re Insecure, Why Not Own It, you’d be better prepared to avoid running into the brick wall of getting caught off guard by tough questions that can derail an interview. 

And in an ideal world, you won't find yourself falling into the trap of getting asked about why you’re leaving your role because you answered that directly after telling the interviewer about yourself… but the world is far from ideal (and I write content faster than most can read it).

Too often leaders trap themselves talking about a tough transition in a compliment sandwich. That is to say, a half-hearted positive thing, a softened fraction of negativity, and a higher-pitched positive thing with 15% more enthusiasm to feign authenticity.   

When you find yourself unprepared, the following is often the outcome. 

[Buying Time]

Ah, you see. I am so glad that you are asking about (this thing I really didn’t want to talk about).

I have had a great experience at XYZ Satanware.io (even though it has only been 4 months). The team, the vision, the (soul-suckingly inefficient, no product-market-fit, overfunded vaporware) product—all exceptional.  
I recognize that I want to get closer to working hands-on with the customer (because XYZ Satanware.io never once paid attention to the customer anyway) and we weren’t in alignment on the overall vision of the company (because the CEO bait-and-switched the role and micro-managed every leadership decision anyway).


I’m not in a hurry to leave (please get me the hell out of here, but don’t take all my negotiation leverage away) but I am entertaining other leadership opportunities at companies like yours where we can find stronger mutual alignment (Please don’t lie about this role. My heart and career can’t take anymore).

Ownership Is A Strength.

Let’s get real. These conversations are challenging and uncomfortable. GOOD.

The cliche is true that it’s not what you say, it’s how you say it. But too much sugarcoating simply sounds like bullshit. And if it’s difficult to put a positive spin on a tough situation, maybe that’s because the situation wasn’t very positive to begin with.

If that’s the case, your concentration should be more about understanding why that situation happened to you in the first place—so you communicate it in a more clear way to avoid it recurring in the future. 

When you have an answer to what went wrong, you’ll at least have the meat of what you need to address when answering why your last role didn’t work out.

Concentrate on being honest, take ownership of your faults and what you perceive the other faults of others to be, and glean what you learned from the experience to avoid this situation later.

For example,

I don’t find my current work fulfilling. I enjoy leading a larger team and the increased responsibility—and I’ve learned a lot. But I made a mistake when evaluating the product and we’re much further away from the growth that really excites me. 

I have learned that I can make a more significant impact on an organization further along. I’m evaluating other opportunities that are a better fit for me—and not flippantly looking at any opportunity to leave. Rather, I’m taking my time to make a smart decision with my next steps and avoiding a poor fit moving forward. Does that cause any alarm or hesitation? It’s not easy to talk about, but I respect being candid. 

More executive leaders need to get comfortable taking these challenging conversations head-on and answering with clarity, confidence, and conviction.

Want to speak directly with me about your career? Contact me below.

Contact Jacob

Get the latest executive career insights each Thursday.

“I get a lot of newsletters. I skim most of them. I read to the end each time I get one from Jacob. Sign up, you won't be disappointed.”

You're safe with me. I'll never spam you or sell your contact info.