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5 questions to ask if you want to find out what kind of work culture you're about to step into.


Today I want to discuss a timely topic for job seekers: unmasking toxic cultures.

I’ll share 5 questions to help you find out if you’re interviewing for a dream job or your next nightmare.

Work culture accounts for the majority of our job satisfaction. In some jobs, you felt respected and appreciated; in others, you felt exploited and underestimated.

There’s no such thing as a single “company’s culture.”

An organization is made up of hundreds of micro-cultures. Some teams are upbeat and supportive; others are gossipy and treacherous. Some groups report to an exemplary leader, while others ladder up to a little tyrant. It all depends on where you fall.

This is an important distinction because people often use blanket statements to describe company cultures, which, good or bad, need to be taken with a grain of salt.

To get a sense of work culture, you need to know which questions to ask.

Let’s dive in!

A work culture can be defined by the worst behaviors that are tolerated.

Every work culture is dysfunctional. There’s no escaping it. The question is what flavor of dysfunctionality you can live with.

To understand a culture, you need to look at how people behave in specific situations: what’s rewarded, what’s punished, how conflicts are handled, who gets to speak up, etc.

At interviews, most people fall short when it comes to inquiring. They assume that there’s a single list of adjectives to describe a corporate culture.

Their question often sounds like this: “How would you describe your culture?”.

The lack of specificity prompts the hiring team to spew out their hit parade of corporate buzzwords: “Sure…let’s see… we are innovative, fast-paced, customer-obsessed, collaborative, fun, what makes us different is our people… oh, and did I mention that we’re like a family?…”.

If you want to get a sense of the culture, be specific. Ask for stories about how people treat each other.

These are my 5 favorite questions:

1) Tell me about your team’s most cringe-worthy failure. What caused it, and how did your leaders respond?

If you value innovation, you want a culture that’s comfortable with uncertainty and risks. How they respond to setbacks shows to what extent they walk the walk. Pay attention to how they frame the failure. Do they show pride in what they learned? Do they hold themselves accountable or show signs of throwing others under the bus?

2) Tell me about a recent success in your team. How did you all celebrate it?

People leave their jobs when they feel that their contributions don’t matter. This question digs into how they go about noticing collective and individual contributions. While not everything deserves a party, great teams broadcast their successes. Do they share wins across the company? Do bosses get involved? Do leaders step back and let their teams shine? Do they show gratitude?

3) Tell me about the last person you promoted (or fired). What made them deserve it?

This one reveals what behaviors they reward (or punish) and how they define their standards of excellence. How do they define “top (bottom) performance”? Do they follow fair and objective criteria? If they can’t give you an answer about a recent promotion, it may mean that there’s no growth path or mobility.

4) What do you wish your leaders were more open about?

What’s not talked about is just as telling as what is. This is a good way to dig into unresolved friction points between employees and leaders. Do they operate on a “need to know” basis? Do leaders stick to their promises? Do they listen to their teams? Are they self-aware?

5) Tell me about a difficult decision you had to make. How did you handle it with those who were impacted?

A great boss will demonstrate foresight and empathy. Pay attention to signs of emotional intelligence (or lack thereof). Did they do something to alleviate the blow after firing someone or canceling a project the team worked hard to deliver? Did they agonize over the decision? Did they do everything in their power to support those who were affected?


Work culture is the difference between a job you love and a job you hate.

Culture is determined by the collection of behaviors that are rewarded or punished.

To uncover these behaviors, get specific. Ask for stories about how people treat each other.

That’s it!

As always, thanks for reading.

Hit reply and let me know how this post helped you. Your comments and feedback (good and bad) are pure gold!

If you are stuck in a mid-career crisis and are ready to start walking out of the fog, ask me about my 1:1 signature career transformation program.

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