How Honest Should I Be During a Job Search?

I know that many of you reading this post might well take offense at the title of this post. After all, doesn’t phrasing the question, “How honest?” imply that total and unvarnished honesty is probably not the best path forward when it comes to landing a job?

In a word? YES.

Look, in an ideal world we could all go around chatting with each other without worrying about what we say being construed in a negative light. But that’s not the world we live in, and it’s DEFINITELY not the world of those you’ll meet early on in the hiring process. This person usually won’t be the one you’ll report to. They’re a gatekeeper, in essence, and their AVERSION TO RISK will far outweigh the relative value they place on someone who “tells it like it is.”

That’s when you need to get strategic. Be honest, yes, but FRAME the situation and POV in a way that plays to your strengths, not your weaknesses! That’s the game played at its highest level.

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Also read: 3 Career Situations Where You Need to Be Brutally Honest 

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Honest vs. Too Honest — How to Navigate

Here are some of the major scenarios to be aware of:

Question: “Did you ever have issues with a difficult boss?”

The TOO HONEST Answer:

“Jim at COMPANY X was a passive-aggressive nightmare who made my life hell for the past two years. He was the kind of toxic person who seems to enjoy spreading that poison around to everyone in his orbit, and it took everything I had not to internalize his judgments and criticism. Frankly, I’m still working on it.”

Why you shouldn’t go this way:

No matter how justified, ANY serious criticisms of a past employer will probably be registered as you having a chip on his shoulder (bad), and being all too willing to badmouth this company should things not work out (worse).

A Better Answer:

“I wouldn’t say issues, but certainly there’ve been times when I’ve had to make some major adjustments to work effectively with a boss. At COMPANY Y I was working with someone really brilliant, but who worked in a COMPLETELY DIFFERENT way than I did. Rather than continue to be at loggerheads, I really did my best to understand what would resonate. I’m a big fan of face-to-face meetings, but my boss at the time didn’t see much value in it. So I routinized an email updating process with him where I laid out exactly what I was working on, and got his buy-in on the most important priorities to focus on. We got past our differences, made incredibly fast progress and this lesson of adapting to people’s preferred working styles is something I practice today.”

Question: “Is there anything that would prevent you from working overtime and weekends if necessary?”

The TOO HONEST Answer:

“You DO know that I’m the parent to two young children, right? It’s painful for me to be apart from them during working hours, so the instant I leave the office the 100% focus is on them. I don’t want to erode that by being on the clock 24/7, but if necessary, I’d prefer to take the work home rather than remain on-site.”

Why you shouldn’t go this way:

While I personally think it is SHAMEFUL for some (not all) companies to judge candidates with family obligations as potentially being “less committed” to their work, I ALSO don’t believe in opening myself up to vulnerabilities needlessly. The right path forward here is not to pretend that you don’t have a family, but FRAME it in a way that demonstrates you’re already at ease with balancing these two worlds effectively.

A Better Answer: 

“One of the benefits of being an involved Dad in the lives of my three kids is getting good at working odd hours, and maximizing what I do when I’m on site. My focus would be on getting everything done during on-site time, and beyond that, my preference would be on addressing it at home.”

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Also read: Should You Ever “Bluff” During the Hiring Process? 

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Question: “Tell me about something which didn’t work out?”

The TOO HONEST Answer:

“Well, the startup I founded 3 years ago has pretty much gone from crisis to crisis without ever stabilizing, added MAJOR stress to my marriage, and pretty much made me doubt the rightness of every life decision I’ve ever made!”

Why You Shouldn’t Go this Way:

As a Career Coach, I’ve had the privilege of working with a lot of successful people over the years. ALL of them have weird twists and turns in their work histories. But what sets them apart is their ability to RE-FRAME these experiences in a beneficial light. To unearth and capitalize on the VALUE of situations most would others turn away from. In other words, they go DEEP instead of getting DEFENSIVE.

A Better Answer:

“I’m proud of what my startup has accomplished over the past 3 years, but for reasons that are totally different than what I expected. I was thrust into a near-daily fight for survival, and what I learned was that one, I can in fact steer the ship during those moments successfully, and also two, at this point in my life I don’t feel like managing the constant instability of survival is the best way to develop my interests/areas of expertise in POINT A, POINT B, and POINT C. This is why I feel like this opportunity is one that’s worth seriously exploring- it strikes that balance that would enable me to more quickly progress in these areas of focus.”