It’s hard to believe, but I hit “post” for the first time in 2010. You subscribed at some point along the way, but it’s possible you don’t remember (it’s been so long), or you don’t want to hear from me anymore. If that’s you, no hard feelings. Just click below:

With that out of the way and hoping you made the right decision… let’s do this.

Ready to Level Up?

Last week, I was hiking, clearing my head, and tuning into the audiobook 101 Essays That Will Change The Way You Think. (Highly recommend.)

The author dropped a line that hit me right between the ears: while we might think other people have it all figured out, they don’t. They may look like they do, but it’s an illusion. And if someone tells you they do… they’re probably doing a great job faking it. And then she got into the vaunted “five-year plan.”

Five-year plan? Real talk: most people are just trying to get through today without spilling coffee on themselves or wondering why they walked into the kitchen. 🫠

The author went even further: if someone does have a crystal-clear five-year plan, they’re probably not dreaming big enough. WOW, OK. And then, as my brain often does, I jumped right to thinking about a shallow—and hypocritical—interview question I’ve heard far too often:

“Where do you see yourself in five years?”

Let’s look at the hypocritical element of this goofy question. Does the interviewer have a detailed five-year plan? Like, right now? Ready to share? Be honest. Is where they are today the result of a perfectly executed roadmap that landed them in this exact job, with the pay and title they planned all along? Highly unlikely. Life isn’t linear, and neither are careers. So why do we keep expecting candidates to deliver polished, forward-looking fantasies?

Most answers to this question are canned, rehearsed, or fluff, telling the interviewer what they want to hear. What do we learn from that? Not much.

Instead of forcing someone to predict the unpredictable, why not ask a question that sparks meaningful conversation and provides actionable insight?

A Better Way

Instead, try this:

What big goal are you excited about today, why is this goal important to you, and what steps are you taking to make it happen? 🤯

This question digs deeper, avoids asking for a made-up future, and uncovers factors like:

• How someone thinks

• What drives them

• How they approach growth

• Whether they prioritize personal or professional growth

• Whether they’re doing anything about it

• And more…

(See the “PS” below.)

There are other downsides to the “see yourself in five years” question. Imagine this: You ask this question, and they confidently reply, “Leading a team, making an impact, and buying a llama farm.” 🦙✨

What are you supposed to do with that? My guess is that llama farm ownership isn’t going to help your team (unless you’re in the llama business). Not super relevant, right?

One Other Super Important Thing

You’re not hiring top 5% talent with shallow questions. Top 5%ers know shallow questions when they hear them, and they see your lack of preparation. If you want top 5% talent, you need to put in the prep work to stand out as an interviewer.

What’s a shallow interview question you’re ready to say “goodbye” to in 2025? Reply or share it in the comments. I promise to respond with alternatives—ones we can all use for more insightful interviews.

Let’s make hiring better, one question at a time.

Go get ’em! 🚀

—Brenden

PS—Here’s one more tip to improve a question like this with thoughtful follow-ups (below).👇🏻