Interviewing – Sasha Dichter's Blog

A job interview isn’t fundamentally different from a sales meeting—and, in both cases, we need to avoid two traps:

Reinforcing an unequal balance of power (by seeming desperate)
Talking too much and listening too little

Equalize the Balance of Power

I’ve mentioned this before, so I won’t dwell on it: there’s a subtle shift between showing up as:

An interviewee—someone who just answers questions well
A potential business partner—a meeting in which two people are working to figure out if there’s a fit between the person (attitude/skills), the job, and the organization (culture/need).

The vibe is one of mutual, respectful exploration. The interview is about much more than clearing the basic hurdles—that puts you in the top 5 or 10 group, but it doesn’t get you a job.

Listen More

The trap of any sales meeting is spending too much time talking about yourself and your product, and too little time learning about what your prospect is looking for.

It’s even easier to make this mistake in an interview: to think that if you earnestly answer every question, you’ll have gotten it right.

Instead, hold a mindset of genuine curiosity, and be as thoughtful about asking great questions as you are about giving great answers.

Don’t do this at the expense of answering the questions that have been asked of you. You must convey that you are a compelling candidate, that you are interested, and that you have strong answers to the interviewer’s questions.

Use Preparation to Ask Great Questions

But you also want to engage in meaningful dialogue, and you can do this with great preparation that’s far beyond the superficial glance at the company website. Things like:

Using AI to learn about the company’s strategy.
Finding articles or talks given by your interviewer.
Spending meaningful time on LinkedIn to figure out who you know in common.
Developing your own hypothesis about the challenges they are grappling with, and coming with solutions to those challenges.

Everyone is flattered by someone expressing deep, genuine interest in them. Your thoughtful curiosity shines a light on them, and it might even get them to drop their guard and share what’s really going on at the company.

You can ask questions like:

Could you tell me more about the division I would be a part of? What’s going well, and what are the challenges?

What would you say this group is best at and what are areas you’re trying to shore up?

Could you describe the culture of this team? Does it differ meaningfully from the overall organizational culture? How?

If I’m really successful in this role, what impact will I have had?

The goal of these questions is to find a jumping off point for conversation, so you have the opportunity to say things like:

“It sounds like you’re eager to have this team take more risks. Is that right?” And then share some thoughts of how you’ve seen that happen / helped make that happen in other places.
“It sounds like getting a better understanding of customer needs is a real priority. Have you thought about _______.”

Uncover a Real Pain Point They’re Trying to Solve

When you get the interviewer to put a real pain point in front of you, the two of you are suddenly working together to address that issue. This is both a more interesting interaction than the traditional interview, and a dry run of you working together with this person.

Once they’ve gotten a taste of that, they’ll instinctively put you in a different category than all the other candidates: they’ve interviewed everyone else, but they’ve gotten a glimpse of what it’s like to work with you.

And you’ve also gotten to see what it really will feel like to work together, so you’re in a better place to see if this is going to be the right place for you.

Everybody wins.

Other posts in this Series:

On Interviewing Well: Introduction

On Interviewing Well: Convey Deep Self-Knowledge (3-3-2)

On Interviewing Well: Owning Your Agenda

On Interviewing Well: Intention

What is the person interviewing you trying to accomplish?

We know what they are doing: posing a series of questions with the ostensible goal of figuring out who you are, what your strengths and weaknesses are, and how well you’ll fit culturally within their organization.

Knowing that, you have a choice.

Your first option is to play their game and answer every question as well as you can. When you do this, you are, bit by bit, handing them puzzle pieces that make up the picture of who you are. Your hope is that those pieces are accurate and complete enough that the picture they paint is a reasonable representation of you and of you in this job.

Unfortunately, this approach is flawed. First, it assumes the interviewer will ask enough questions, and the right ones, so they’ll end up with a good-enough set of “you” puzzle pieces—that’s leaving a lot up to chance. Worse, you’re setting yourself up to be compared in a like-to-like way with everyone else who answered that same set of questions.

Here’s a second option, inspired by the most creative interviewing I’ve ever seen. The interviewer had a list of 40 traits (e.g., data analysis, public speaking, sales, making new connections, coding), and she told the interviewee that she’d be reading down that list. She asked the interviewee to to rate their abilities on each trait on a 1 to 10 scale. She would go through the list quickly—the whole thing probably took two minutes—and then discuss.

So much is happening here. The interviewee quickly figures out there’s no gaming this system: they can’t credibly say they’re great at everything, so they are likely giving a more accurate picture. Plus, so much information comes across about the candidate beyond each individual answer: are they a tough or kind self-grader? How quickly do they answer on some traits (I’m confident about this) vs. others? How consistent are the answers? What does the overall picture look like? And how do they react to this surprising exercise?

Since most interviewers won’t take this approach, your option is to take it for them with the 3-3-2 approach.

With this approach, you are going to describe eight things about yourself:

Three that you’re solid at

Two that are weaknesses of yours—things that, if they’re core to this job, mean that this job isn’t right for you

And three things that are your superpowers

For example:

“Three things that I’m good at and would be a core part of any job I’d do well: managing large teams, handling stress/complexity, and selling.

On the other hand, two things that I’m really not great at are: creating PPTs to present my ideas; and living and dying by getting the last decimal point right. I’m good at details, but if that’s my whole job I’ll go insane.

And my three superpowers are: strategic thinking (figuring out the way forward from a bunch of complex options), coaching, and building community.

I’d be happy to give you examples of any of these if that would be helpful.”

You have to be really honest here—no “the thing I’m worst at is having high standards.” You’re intentionally stepping outside of the interview game and telling the interviewer what she really wants to know.

What’s powerful about this is the clarity and confidence you demonstrate by giving someone all the pieces to your puzzle. You’re saying “this is me, the whole story, both the good and the bad. If that’s a fit for what you’re looking for, great. And if it isn’t, that’s fine too.”

Of course, you can adjust as you see fit: how deep are you going to go with what you share? How long a list?

What matters most is that it’s genuine: you’re communicating that you’ve reflected deeply on yourself. You’re saying that you understand this is a matching game, not a “pick the best candidate” game. And you’re giving yourself the chance to say, without bragging, “out of everything you might be looking for, these are the areas where I really shine.”

This approach consciously rejects the cat-and-mouse game of interviewer question and answer. It demonstrates the kind of self-knowledge that itself will distinguish you from the pack.

Most of all, it’s breaking the mold, doing something memorable that says “I’m an open book, this is the information we both need to proceed. Let’s have that conversation.”