This is a part of a new series where I share snippets of learnings I've had in my 10 years of being a CTO! The topic today is getting honest answers between the little white lies of interviews.
I've conducted hundreds (maybe thousands) of interviews. One thing I've learnt is that it's all a game where you're trying to find out if someone would be good for the role, and they're trying to sound like exactly what the role asks for. This becomes a dangerous sport at scale because it can make it really hard to distinguish the bad, from the good, from the great.
This is especially true for Distru, we're doing over $13M ARR with 8 engineers as of 2026, so one wrong hire is >10% of the engineering team (yikes).
The reality is you can't ever fully stop little white lies. What you can do is make the honest answer the easiest one to give. I do that with three rules:
- Keep it casual
- Humanize and frame your questions
- Double-click into specificity
1. Keep it casual
For the candidate, an interview is already nerve-wracking, and that puts a wall up straight away. You want them comfortable enough with you that they don't see you as a judge or an executioner.
The obvious way to get there is to make the whole thing a relaxed chat. This doesn't however mean you should not have structured questions or purely go off of vibes.
Instead, keep the tone casual and the format structured:
- Open with 1 minute of quick chatter/intros
- Come with a good energy/rhythm
- Control the agenda right away. Never let the candidate run the schedule
Here's how I usually open:
“Hey XXX, how's it going? Thanks for taking the call! Where are you calling in from today? [...chatter for 1 min...]. I just wanted to give you a high level agenda for today. My goal here is to really understand who you are, learn a little bit about your past experiences, and I'll double-click in where I find things interesting. Near the end of the call, I definitely want to save some time for you to do the same for us as well. Going into any new position, I think it's really important on both sides to de-risk as much as possible and just try to understand as much as you can. Feel free to ask me any questions. There's nothing off the table on my end. I hope I can do the same for you as well! Does that sound good?”
This establishes the rhythm, controls the agenda, and also keeps it casual.
2. Humanize and frame your questions
The mistake I see most is people reading questions off a sheet like they're filling out a form. I hate this. As the person answering, I think “oh, they're asking me a scripted question, I need to give a scripted response.”
Don't get me wrong, planning your questions and taking notes is good; it's what makes the interview structured. Reading them out like a script is what makes the candidate throw their walls back up.
The key is to humanize each question and frame it with why you're asking.
Note: the framing should never tell them what a good answer looks like. They're already trying to sound like what the role asks for, so if you hint at the answer you want, you'll get it.
Here's an example of my favourite interview question I ask:
“What about your work gives you energy & what takes away your energy?”
Now if you ask this question as is, here are some responses you'll get:
- “Getting things done gives me energy”
- “Delivering value for the company gives me energy”
- “Endless meetings take away my energy”
- “Politics and red tape take away my energy”
The issues are that the question wasn't humanized, thus the answers are guarded, and the question wasn't framed, so the answers are generic/vague.
You might as well not have asked the question at all.
Now here's how I actually ask the question:
“Because Distru is a startup company, one of the really cool things is that everybody can truly work on things that they are energized by. With that being said, I'm always very curious about what gives someone energy and what takes energy away from them. Can you think of some products or features you've built in the past that truly gave you a lot of energy, and vice versa, some products or features you've worked on that you've noticed tended to take away your energy? This doesn't necessarily mean you were good or bad at them. I just want to understand where your energy naturally tends to flow, and this is different for everybody, and there's no right answer.”
This is the same question, but with a few things done better:
- You've given context as to why you're asking the question and how it applies to their role
- This is less of a test, and more genuine curiosity
Humanizing and framing questions like this disarms lies, because you can't script lies to an unscripted question.
3. Double-click into specificity
I see this mistake so often with recruiters and people who are new to interviewing. They ask a question, the candidate gives an answer, they jot it down and move on, because they want to churn through a list of questions or they're short on time. If you get surface-level answers to every question, you're going to have a surface-level view of the candidate.
I always double-click deeper, and into specifics. Specifics matter so much: names, numbers, dates, who did what.
Imagine a candidate tells you about a billing system they built with a team. A specific double-click could be:
“You mentioned you worked with a team on this. Can you break down for me exactly who was on the team, who did what, what was your part and what was theirs? How many people? I want to understand the logistics around this.”
This level of specificity is hard to make up on the spot. Maybe it turns out their involvement wasn't that much at all. Or maybe the team was way smaller than you thought, and what they meant by “a team” was that they really did everything!
Either way, you've got something concrete to check. In this example, “we” isn't a red flag on its own; what you're after is the “I” inside it.