Hiring Manager to Job Seeker: I hate interviews just as much as you

Apr 12, 2024

I dread interviews.

90% of the time, the interviews consist of the same mundane flow. I ask the questions, the candidate responds. The candidate waits until the end to ask questions, but I can predict what those questions will be before the interview even begins.

On paper, many of these candidates look promising. Their AngelList profiles look compelling, they have a presence on LinkedIn, and their social media checks out. But once they’re on that first phone interview, it all changes.

They can barely articulate their experience, let alone showcase a strong personality. Most interviews last 15 minutes, although I can usually tell within the first two how the rest of the interview will go.

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For the sake of both parties, here are five ways to make interviews meaningful and worthwhile:

1. Push for conversation, not interrogation.

Most candidates will answer question after question. By the third question, I’ve already begun answering emails as candidates continue to talk about themselves without showing any interest in engaging with me.

On the rare occasion where an interviewee turns the interview into a discussion, they have my interest. When asked the typical first question, “Tell me about yourself,” everyone usually just reads their resume out loud.

But the interviewee that gets my interest is the one that brings up recent developments in our company, and ties their interest and value to what’s currently happening in our organization.

He or she asks thoughtful questions, begins a larger conversation about our goals and needs, and connects their skills and experiences as ways to contribute.

They immediately spark a two-way, meaningful discourse, instead of a mundane back and forth.

2. Take an interest in the interviewer.

Please don’t ask questions that you can easily google the answers to. Candidates often ask me why I started Skillify and Edvo. If they had done their research and gone to the Skillify or Edvo website, they would have seen the story published at length.

Or worse, they’ll ask me when Skillify or Edvo was founded, and then I’ll really want to end the interview.

It is so refreshing (although it should be the norm) when candidates use their research to ask thoughtful follow-up questions like “What was it like launching a company as a full-time student?” or “What was it like being raised in Palo Alto and witnessing the changes over the past few years?”

Take an interest in the person you are interviewing, not only because it strengthens the connection you two will build, but because it is an opportunity for you to learn about a potential colleague.

Thoughtful questions lead to meaningful conversations, and allow you to understand the values of the people that work in the organization you are applying to.

3. There is much more to preparation than just reading the company’s website.

Every applicant explains their interest in our company's mission, and connects their personal experience to it, but very few are prepared to answer questions related to the industry we operate in.

For example, since Skillify specializes in work-based learning and career-readiness, I ask applicants if they’re familiar with Career Technical Education (CTE) funding. More often than not, people say no.

I ask other questions related to our industry, and most candidates ramble, sharing opinions based on non-factual information. What’s worse is when I catch candidates lying about their knowledge. I recently had a candidate say yes to knowing about CTE funding, so I followed up with, “Great, what is your understanding of the trends happening to these funding sources?” She responded with, “Now that I think about it, I realize I may not be familiar with the funding.” Face palm.

4. Be aware of your words.

I’ve lost count of the times I’ve heard “That is so amazing” after giving a fairly simple or ordinary response to a candidate’s question.

When a candidate responds with such enthusiastic words, despite having no enthusiasm in their voice, I immediately sense a level of superficiality that takes away from a meaningful conversation.

It is normal to feel nervous during an interview, and that nervousness may cause you to go on autopilot. It is important to be aware of when this happens to you, so you can actively work on preventing it.

If you’re truly amazed by something, use the right words and tone to share that sentiment, followed by an explanation of why you feel that way. No need to hide your excitement - it’s flattering to know that my work elicits such a positive reaction. But help me see that sincerity.

5. Get to know the organization, not just the interviewer.

Interviewing is a two way process. The interviewer is evaluating you just as much as you are evaluating the opportunity. There are many reasons why you would not want to work for a certain organization, so make sure to understand the organization as a whole, and not just the interviewer.

I’ve heard from a few people now that they have been offered jobs before being invited to the place of work, and before meeting any colleagues. While this may be okay for completely remote positions, it is not recommended if you are expected to work in an office and have not had an interview or meeting in said office.

Request an in-person/in-office meeting, and a chance to hear from your to-be colleagues - this advice has saved quite a few people from horrific “new job” experiences. In one case, the employer approved this request, and the candidate was able to spend two hours at the office.

After doing so, she quickly realized it was not the place for her. Within her two hour visit, she overheard a group of six employees making racist remarks. When one noticed that she may have overheard, he yelled out, “Don’t tell the boss!”

If you’re going to commit to a job, make sure you’re ready to commit to every aspect of it.


As a regular interviewer, I crave authenticity and demand integrity. As a job seeker, you should too. Interviewing takes time for both parties and frankly much of that time is wasted. Let's make these conversations meaningful, and do meaningful work.