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Don’t Sell Yourself Short — Lessons in not F*cking up your job interview

I interview a lot of people for a lot of different roles at a range of seniority levels (many more senior than me). No matter who it is or what job it’s for, all of the serious job applicants have a pretty straightforward goal — get the job offer.

No sh*t I know. People don’t interview for fun.

Bear with me.

There’s a point to this diatribe (two really).

First, in order to maximize your chances of getting hired you need to come prepared.

I know, that seems obvious too.

After all, who doesn’t prepare for big moments like these?

The answer to that question is most people.

At least 75%+ of the people I interview seem extremely unprepared when they come in for a face-to-face interview (step 3 in our process at CBI). Perhaps most surprisingly, this seems to be true across all seniority levels.

So what does being prepared for an interview really mean?

Step 1: Being Prepared Starts With Knowing the Basics

There are questions you should expect to be asked and being surprised by them will leave you dead in the water.

For example if you don’t have good answers for:

  • why you’re applying to a company
  • why you are leaving/looking for something new
  • how you see this job/company contributing to your career growth

Then you’re not going to get hired very often.

And if:

  • you haven’t researched the people you might work with
  • you can’t ask good questions that are role and company specific
  • you don’t really understand the key success metrics/how the role is measured
  • you don’t follow up afterwards with a timely note that is personal and shows you listened

Well then I guarantee that you’re lowering your chances of getting the job (is it just me or do generic follow ups KILL you too?)

Step 2: Demonstrate you have the skills for the job

This is obviously job specific. Different types of jobs have different skills that get assessed through different types of interviews.

If you’re serious about getting hired then chances are you’ve spent time perfecting answers to the different types of questions or practical tests that you expect to see for your role. That’s harder to give general advice for.

So where are we?

At this point you know the company’s history and mission, you know the specifics about the role, you’ve thought about why this job in the context of your career and ambitions, and you are prepared to show that you can do the job.

Despite most people failing to do some (or even all) of this, we’re still just talking about the table stakes.

The rest is about playing the game the right way.

Step 3: Understand the Interview Game

You are not the only candidate for this job. You are not the only person with the skills and talent to do this job.

In fact, if the person interviewing you decides not to hire you it probably won’t effect their day-to-day. It’s not personal. They’re just busy. They will never be able to measure and rarely understand (let alone think too hard) about the opportunities/people they missed out on.

It’s a harsh truth.

It also has nothing to do with your abilities.

You really might be the best person for this role and team. You really might be the person who wants it the most.

But the person interviewing you isn’t a mind reader.

It’s up to you to show them the person they are looking for is you.

You have to sell yourself.

Your merits, your hunger, your drive, your fit. You have to sell all of this to a group of people, usually with less than an hour of face time with any one individual, and you have to make sure your impression holds up when they compare you against other people.

The good news at least, is that the person interviewing you wants (sometimes desperately) to find the right person. Show them you will make their life better.

What if you hate selling yourself?

Now the idea of selling yourself has probably made a few people cringe at this point.

I get it.

Sales can have a negative connotation. It can feel sleazy. You don’t want to talk about yourself. It feels disingenuous.

If you’re not in sales thinking of a job interview in this way can be uncomfortable.

Unfortunately it doesn’t really matter how you feel. Love it or hate it the job application process is the process of selling yourself.

Step 4: Play the Game the Right Way

Now there are a lot of useful analogies between a typical enterprise sales process and successfully interviewing for a job.

There’s getting noticed, there’s doing discovery, there’s establishing value by uncovering pain points and showing how you can solve them, there is strategically positioning yourself against others, there’s driving towards close and so on.

All of these analogies are valuable and are probably worth an entirely separate discussion.

But I’ve already written too much.

So I want to share just one last piece of advice that I’ve noticed from doing all these interviews in the last 2+ years.

The One Question to ask at every job interview

You see there’s one question that sales people consistently ask when they interview for a job that no one else seems to.

Now asking this question isn’t natural.

In fact it’s actually really uncomfortable. It makes you feel open and vulnerable. It feels like you’re opening the door to losing the job.

But sales people push past these feelings and ask anyway. I think that’s because they tend to recognize the value of the face-to-face meeting. They’re used to having a small window of time to position the value of what they are selling.

They’ve also been burned by NOT asking this question. They know that uncovering this information is too important not to take the risk.

So what is this question that sales people ask and no one else does?

They ask where they sucked during the interview.

That’s it. They say: “Hey man, did you think I sucked at any time while we were talking?”

Now of course they don’t usually say it like that.

It’s usually asked at the end of the interview and framed something like so:

“Do you have any reservations about my skills or what I’ve said here? Is there anything else I can answer that would help you evaluate whether I’m a good fit?”

There are countless ways to word versions of this question, and I’ll be the first to admit that a lot of people don’t really ask it “well”. But it doesn’t have to be an awkward standalone moment at the end of an interview. It doesn’t have to put the interviewer on the spot. You can weave elements of this into the conversation.

Besides, as long as you genuinely listen to what comes next it’s worth the risk. The reason why is simple.

Knowing what shortcomings your interviewer perceives lets you address objections that otherwise might have killed your job application without you ever knowing about them.

And that, along with being prepared ahead of time, should move you closer to your goal of getting hired.

Why did I write this post?

In case you’re curious about why I felt inspired to write this post, it’s because (1) too many qualified people don’t get the job because of dumb mistakes and (2) I interview a lot….

Over the last 2+ years alone at CB Insights I’ve interviewed hundreds of Candidates as we’ve built the company from ~25 people to 200+ including from less than 5 to more than 60 people in business development and customer success and from one counterpart in marketing to a team of 10+.

In general I’ve been really fortunate in the diversity of roles, seniority level, and background of people I’ve talked to. Whether interviewing a sales development rep (SDR) out of college, a seasoned Enterprise Account Executive, a key sales ops hire, a big company Director of Customer Acquisition, an SVP to take over a multi-million dollar PnL events program, or interviewing and getting interviewed right back by my eventual boss, every role and every conversation has been a bit different.

In this process we’ve hired great people, but along the way I’ve had some really terrible interviews and a lot of average ones. Some of this time was with Candidates who I’m sure would have crushed the job at CBI.

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