ECOSYSTEM by JD

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Interviews.

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Interviews.

My honest responses to six commonly-asked questions.

JD Dillon
Feb 26
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Interviews.

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I haven’t interviewed for a job in over 7 years. I’m fortunate. But that doesn’t mean I’m unprepared. 

An oil painting of a businessman surrounded by question marks | DALL-E

The game. 

I’m always thinking about the next stop on my career journey, even if I’m not actively job hunting. I evaluate my resume every six months. I’m constantly exploring new ways to boost my professional presence. And I practice my interview skills as often as I can. 

Interviews have always been a big part of my professional life. I started interviewing candidates as a hiring manager when I was 18. I’ve interviewed hundreds of people and been interviewed dozens of times. What have I learned from all of this interview experience? It's a game.

We’d love to think we’re having an honest, meaningful conversation. In reality, the people on opposite sides of the table (or Zoom window) are playing mental tennis. The interviewer has serve. The interviewee does their best to volley responses, stand out from the competition and secure the win. 

I know that sounds cynical. But I’ve also been through an application process with 14 … that’s FOURTEEN … rounds of interviews. I’ve had a few great conversations over the years. But more often than not, I was trying to figure out what they wanted to hear so I could check as many boxes as possible on a rubric I knew was there but had never seen. It’s no wonder my favorite jobs were the ones that didn’t require interviews. I was picked based on my ability to do the job, not how well I sold myself during a single appearance in front of a panel I’d never met before. 

Nonetheless, interviews are part of workplace reality. We can’t avoid them, but we can make sure we’re prepared for them. So I scoured the latest TA thought leadership to find today’s most commonly-asked interview questions. Unfortunately, they haven’t changed much over the years. Here are my honest responses to six questions that popped up the most. 

Tell me about yourself. 

This question is more about preparation than getting to know you. It’s used to quickly determine what kind of conversation this is going to be. If you struggle with this layup, the interviewer may cut things short. 

I’m obsessed with 4 things:

  • Back to the Future. I can recite every line of dialogue from the first one, which is a perfect movie.

  • Broadway musicals. Hamilton, The Book of Mormon and A Gentleman’s Guide to Love and Murder are my top three.

  • The Philadelphia Flyers. Sure we haven’t won a championship in 47 years, but … that’s all I have to say about that.

  • And helping people feel capable and confident in their ability to do a great job every day.

Thanks for reading ECOSYSTEM by JD! Subscribe for free to receive new posts and support my work.

Why do you think you’re a good fit for this role?

This one is a two-parter about expectations. First, do you understand the expectations of the job - what you’ll be expected to do day-to-day? Second, do your expectations align with the reality of the job? Misaligned expectations will result in quick turnover. 

I’m confident I’d do an exceptional job in the day-to-day performance of the role. Otherwise, I wouldn’t be here speaking with you today. But I believe fit goes beyond knowledge and skill. It’s really about culture - how we bring our values to life in the way work is done every day. So I reached out to a few people on the team to get a better understanding of how the company works. I love what I heard. (This is where I’d insert specifics). That’s why I’m confident this is a good fit for me as well as the organization. 

What’s your biggest weakness? 

This is a trick question. They’re not really looking for a weakness. Again, they want to see if you prepared a solid answer for one of the most easily anticipated interview questions in history. And please don’t say “I care too much” or “I work too hard” or anything like that! 

It’s the next thing I have to work on. And then the next one. And then the next one. I’m always looking for new, meaningful ways to contribute to my team. I never want to be the smartest person in the room or on the project. I must always be learning, especially through feedback from my peers and collaborators. I’m never going to be perfect, and I’m always going to have room for improvement, even in areas where I may be the local expert. If there’s one topic that sticks as my biggest weakness, that means I’m doing something wrong. 

Why are you leaving your current job? 

Frankly, this isn’t any of their business. They want to see if you’ll bad mouth your former employer - specifically your manager. If you take the bait and throw someone under the bus, they’ll mark it as a red flag (even if those people deserved to be under that bus). 

The truth is I’m always in the process of leaving my current job. That’s what professional growth looks like in today’s workplace. We don’t live in a world where people start and end their careers with the same companies anymore. Sure, some people may enjoy long, fruitful relationships with organizations uniquely aligned with their goals and values. But in most cases, growing means moving on, exploring new opportunities and taking risks. That’s how I have always approached my professional development, and I feel it benefits me and my employers along the way. 

Tell me about a time …

This is a process question. They want to get a sense of how you solve problems. Are you able to break down a simple scenario into clearly defined pieces to achieve a desired outcome? Prepare a shortlist of example scenarios that align with the role and include clearly defined steps. For example, if you’re applying for a customer-facing job, you need an answer for “tell me about a time you had to interact with a difficult customer …”

Listen to the audio version for my off-the-cuff, Disney-inspired response. 

Where do you see yourself in five years? 

I can’t believe anyone still asks this question. This just isn’t how careers work anymore, especially after the past few years. How would your response to this question in 2018 compare to where you are today? Still, prepare a response about your short-term career path. 

I’ll be doing meaningful work that I’m passionate about for an organization that aligns with my values. I’m certain about that. Otherwise, it’s my responsibility to continue expanding my skills and broadening my experience so I’m prepared to take on new projects and opportunities as they’re presented, even if they’re unexpected. 

Final thoughts.

What do you think? Would you hire me?

The ultimate goal is to find an organization that chooses not to rely on transactional interviews to determine fit and make hiring decisions. Those jobs exist. I know from experience. But most companies don’t operate this way. The job may be awesome, but there can still be an antiquated hiring process between you and it. 

Every interview starts with a choice. Tell them what they want to hear or be totally yourself. I vote for the latter - but sometimes you just need to get the job. 

Here’s one of the best articles I found on preparing for interviews. Let me know how I can support your job search - now or in the future. Follow #CoolLDJobs on LinkedIn for my curated lists of L&D openings every Monday, Wednesday and Friday. 


One thing this week.

Send a DM. Is there someone in your profession who you look up to? Someone who does amazing work that inspires your own? Someone who could make your day/week/month if you had a 15-minute conversation with them? DM them on LinkedIn this week. Now, if that person is Brené Brown or Ryan Reynolds (who actually has a LinkedIn profile), they’re probably not responding. But I’m always surprised by the number of people who assume they’d be bothering me (a person who is definitely not Ryan Reynolds) if they reached out for a quick chat. 

Bonus: offer to buy the person coffee or lunch as a thanks for the convo! 


Coming up.

In The Know. I’m sitting down with Shawn Kanungo, innovation strategist and the world’s best virtual keynote speaker, on this week’s In The Know. Shawn and I have lots in common. We both have awesome hair styles. We both get really excited when we talk. And we both published new books in 2022. We’ll explore proven ideas for managing disruption from Shawn’s book The Bold Ones, including how to help people embrace change rather than fear it. 

Join us on LinkedIn Live for ITK this Wednesday, March 1 at 1130am ET. Or catch the recorded episode on Axonify’s LinkedIn or YouTube channels. 


Next week, I’ll explain why I owe my entire career to PowerPoint.

Be well. JD.

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