I Got One of My Favorite Interview Questions from a Date…It Changed My Hiring Game

Chris Leithe
3 min readOct 11, 2022

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How one question can help you understand if an interviewee… or a date will be a good fit

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Years ago I was sitting across from a date, she was a badass. I was newly single and had been on tons of dates, and was always asked the same questions: “what do you do”, “what kind of food do you like”, “what does your family do”, etc. They’re fine questions but they’re routine and ordinary and don’t cut to the heart of anything.

So, I was stunned, excited, and INTERESTED when my date broke the frame and asked me one of her favorite questions. For a person to ask this question, they had to be a serious person, someone who takes their time seriously, honors it, and hopefully would therefore honor mine.

Her eyes narrowed, she leaned back and said, “tell me about your routine.” My routine! I’ve been waiting for someone to ask me this for years. My routine was meticulously crafted, not rigid, and always open to options for improvement. If you know me, or worked with me, you may know parts of it because I wouldn’t shut up about it (comment below and remind me of it when we worked together ;) ). But just because I would be excited about this question, doesn’t mean you will be, so let me tell you why it changed my game.

We’re all looking for people who are intentional and thoughtful to work with us: “A players” who will put their heads down and figure it out and deliver repeatable results. In an interview (or a date), a routine tells you about a person’s interests, their loves, their passions. It helps you find common ground and also helps you understand if they take themselves and others seriously. Not seriously in a prideful way, but seriously in a “I only have one life to live and want to make as much of it as possible” kind of way.

As a result of this date, I started asking this of interviewees. Sometimes they would ask me back and I would share. I always developed more empathy for the person across from me and I understood where and how they might fit into the organization I was a part of.

I knew that stable and structured routines lead to more repeatable days…I knew what I needed to do every day to be happy, healthy, and fulfilled, and doing those things routinely ensured my days would be better on average. Similarly, you can often expect the same thing from a person at work: If someone knows what goes into creating a successful day for themselves each day and they repeat it (e.g. it’s a routine), it often translates to repeatable success at work.

However, sometimes people will try to draw a wall between personal and professional life and don’t use the skills from one part in the other. If a calendar helps you be successful at work, shouldn’t it also help you be more successful at home? If date night helps you connect better with your significant other, shouldn’t one on ones or team outings help you connect better with your teams at work? The same is true about building routines for yourself at home and at work.

When you interview someone try to get an idea of both… “can you tell me about your routine? Feel free to start from the moment you wake up to when you go to bed.” It’s a great way to break the ice and understand the candidate more deeply. If they don’t have a routine, it doesn’t necessarily mean that they won’t be successful, but they just might not be the right fit for your role. Even creatives can benefit from routine (more on that later).

Many of my articles will aim to identify ideas and concepts that not only will impact your work but will also be beneficial at home as well. Drop some of your favorite interview questions in the comments or some of the things that are important to your home or work routines to inspire others!

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Chris Leithe

Hard won insights from failing and trying again. Startup, Entrepreneurship, Mindfulness, and Spiritual Enthusiast.