Hey folks, welcome back to my weekly newsletter.
If you’ve ever been asked the question “Where do you see yourself in 5 years?”
This newsletter is for you.
I was sitting on an interview panel last week and towards the end, one of my colleagues asked the candidate where she saw herself in five years.
She responded confidently with a great answer but she didn’t even pause for a second, making it clear that she had rehearsed this one.
And I noticed I trusted her a little less because I have asked this question hundreds of times, and the honest answers aren’t crystal clear.
Because the way most people prepare for this question is the opposite of what actually works on the person sitting across from them.
We as humans like knowing how things end: whether it be a movie, story or an interview.
Most startups don't know what they'll be building in 2 quarters, and the company interviewing you has probably changed direction more than once in the last couple of years.
The World Economic Forum projects 170 million new roles globally by 2030, most of which do not have names yet.
Here’s what we are trying to gauge:
We as interviewers are testing three things:
That last point carries more weight now more than ever because hiring and replacing people is expensive.
The weakest answers name a job title and sound like "I see myself as VP of Product in five years", or "I want to be leading a team."
The problem is you're betting on an org chart that may not exist by then.
It also makes the current role sound like just a stepping stone.
That answer still makes sense regardless of the company restructures / role changes / title update.
Most people give an answer that's entirely about themselves, make it about their growth, skills, and ambitions.
Not one line connects it to what we’re building.
If you sit in my shoes, you would want to work with a candidate that has clearly thought about where the company is going and not just about their life.
And in 2026, where AI tools can generate a polished generic answer in seconds, genuine interest is the hardest to fake and is a signal that you’ll actually stay at the organisation.
What not to say. Ever.
A few answers that will end your chances, even if everything else went well.
Naming a competitor, obviously. "I'd love to eventually work at Google" when you’re interviewing for Microsoft is not acceptable, even if you're laughing as you say it.
A goal that has nothing to do with the role.
If you're interviewing for a finance position and your 5-year plan is to start a restaurant, that's a personal conversation which is not relevant in that interview.
"I just want to learn as much as possible." is vague and lacks direction.
Learning is a method / process, it cannot be a destination.
Be specific about what you want to learn and why.
One last thing.
Notice that none of this is about having the perfect answer.
Everything I mentioned they all come back to the same thing which is that we as interviewers reward you for being honest about where you want to go.
Don’t craft an answer you think we want to hear.
Hit reply: what's the most honest answer you've ever given to this question, and did it help you or hurt you?
I read every email.
Swati