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  • Writer's pictureBenjamin

𝗥𝗲𝗰𝗿𝘂𝗶𝘁𝗶𝗻𝗴 - 𝗕𝗲𝘀𝘁 𝗜𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝗶𝗻𝗴

Updated: Dec 2, 2021


Effective interviewing parallels a successful startup – clear vision and values, objective criteria for success, and learning built on metrics.

To separate a strong candidate from merely a good interviewer, build a process based on a clear job description and effective screening.



𝗣𝗿𝗲𝗽𝗮𝗿𝗲 𝘁𝗵𝗲 𝗜𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝘀


It’s tempting as a startup to say that we’re too busy growing to spend time thinking through the recruiting process. Keep in mind, this process impacts the company’s future – adding people to apply today’s plans and to create tomorrow’s ideas.


Someone should own the process e.g. preparing candidates and interviewers with some information about each other.


Set expectations along the way e.g. How long you expect the interviews to last? Will they be a panel or one-to-one interviews? After each encounter, be clear on timeline and next steps.



𝗥𝗲𝗰𝗿𝘂𝗶𝘁𝗶𝗻𝗴 𝗠𝗮𝘁𝗿𝗶𝘅


At this point, I like to build a Recruiting Matrix which starts with high-level aspects of the role (e.g. Experience, Skills, and Culture) and then creates objective measures based on the candidates’ responses.


For each possible score there is an expectation. I usually use a range of 1-5 with criteria for each score. The point here is not to choose simply the highest ranked candidate for the position. The scoring helps to tier candidates. The criteria help interviewers know what to measure. Based on job-related criteria, this should help to remove hiring bias.


The recruiting matrix helps to divide questions among interviewers so the candidates do not hear the same questions repeatedly.


𝗥𝗼𝗹𝗲 𝗣𝗹𝗮𝘆𝘀

When the candidate re-enacts job-related conditions, you see how they would handle a realistic situation. Simultaneously, candidates learn more about your company during role plays. This is a useful and fun way to play out real scenarios.

Since role plays can be stressful, however, allow candidates time to collect their thoughts and frequent breaks.

𝗣𝗲𝗿𝘀𝗼𝗻𝗮𝗹𝗶𝘁𝘆 𝗧𝗲𝘀𝘁𝘀

Some companies hire for personality either consciously, to increase their diversity in ideas, or unconsciously as a conformity bias. There is a lot of research around matching different personalities for higher productivity and better management.

Without a trained expert, however, my concern is that interviewing for personality will devolve into rejecting someone on the grounds of “poor cultural fit”. Seek guidance to avoid any pitfalls here.

𝗠𝗼𝗿𝗲 𝗨𝘀𝗲𝗳𝘂𝗹 𝗧𝗶𝗽𝘀

𝘔𝘶𝘵𝘶𝘢𝘭𝘪𝘵𝘺: During interviews, you are clearly trying to learn more about the candidate. They want to know more about you too. I encourage questions at the beginning and the end of interviews.

𝘖𝘱𝘦𝘯𝘯𝘦𝘴𝘴: You want to emphasize the good parts about working there and also explain the tough parts. If you don't, when they discover you were holding back information, trust is broken.

𝘝𝘢𝘭𝘶𝘦𝘴: You want people who will push the boundaries and strive for new ideas. At the same time, you don’t want people who will cross the line and disrupt the team. Surface and discuss those distinctions.

𝘎𝘶𝘪𝘥𝘢𝘯𝘤𝘦: Be fair to everyone who applies. Make sure all questions are job-related and ask all the candidates the same questions. Give interviewers expectations and samples to ensure consistency.

𝗙𝗶𝗻𝗮𝗹, 𝗕𝗶𝗴 𝗧𝗶𝗽

Many startups are eager to immediately fill a position. This urge overwhelms hiring practices. Give in to the urge and expect the result of a bad hire and/or a new search just months later.

One obvious sign of quick-draw hiring is having only one candidate for the position. Under the guide of “this is the perfect person” the process stops and you are simply left to choose someone or no one. Don’t fall for this false dichotomy.


Insist on meeting at least 3 qualified people for a position.

When I’ve regretted hiring decisions, it's often from hiring too fast and/or having only one option. Don't substitute problems.

There's a lot to consider in interviewing, from consistent procedures to innovative questions. High yields come from great investments.

Attract and qualify the best talent to help you scale and grow quickly.


---- 𝐔𝐬𝐞𝐟𝐮𝐥 𝐚𝐧𝐝 𝐈𝐧𝐬𝐢𝐠𝐡𝐭𝐟𝐮𝐥 𝐐𝐮𝐞𝐬𝐭𝐢𝐨𝐧𝐬 ----

Almost no one enjoys the drone of following a résumé or LinkedIn profile to review each step in a candidate’s career. Also, those summaries may be incomplete or inaccurate.


These interview questions should liven up the interview and help you really understand the candidates' thought process and motivations.


𝗜𝗻𝘁𝗲𝗿𝗲𝘀𝘁 𝗶𝗻 𝗪𝗼𝗿𝗸𝗶𝗻𝗴 𝗮𝘁 𝘆𝗼𝘂𝗿 𝗖𝗼𝗺𝗽𝗮𝗻𝘆

  • What did you do to prepare for this interview?

  • What is something you learned about us since the last discussion?

  • What is one thing that could be better here (e.g. if applying for a marketing role, what could be better about the website)


𝗪𝗼𝗿𝗸𝗶𝗻𝗴 𝗦𝘁𝘆𝗹𝗲

  • 𝘓𝘦𝘢𝘳𝘯𝘪𝘯𝘨: What’s one critical piece of feedback you’ve received that was really difficult to hear?

  • 𝘔𝘰𝘵𝘪𝘷𝘢𝘵𝘪𝘰𝘯: What motivates you to work?

  • 𝘔𝘢𝘯𝘢𝘨𝘦𝘢𝘣𝘪𝘭𝘪𝘵𝘺: Who has been your best manager and why? Tell me about a perfect day at work.

  • 𝘚𝘦𝘭𝘧-𝘈𝘸𝘢𝘳𝘦𝘯𝘦𝘴𝘴: What are you really good at, but never want to do anymore?

  • 𝘔𝘦𝘯𝘵𝘢𝘭 𝘏𝘦𝘢𝘭𝘵𝘩: This job can be stressful. How do you manage stress at work?

  • 𝘊𝘰𝘯𝘴𝘵𝘳𝘶𝘤𝘵𝘪𝘷𝘦 𝘍𝘦𝘦𝘥𝘣𝘢𝘤𝘬: What is one way to improve our recruiting process?


𝗥𝗼𝗹𝗲

  • What professional achievement are you most proud of? What were the outcomes of that work?

  • What do you want to do differently in your next role?

  • What do you plan to get done in your first three months (for later interviews)?


𝗦𝘁𝗮𝗿𝘁𝘂𝗽 𝗖𝘂𝗹𝘁𝘂𝗿𝗲

  • What new things have you tried recently?

  • How do you facilitate your own career development at work?

  • Tell me about a time you took unexpected initiative.

  • What should our team do differently to yield a 10x improvement?

  • Why might we be unable to raise our next round of financing?


The point of the interview is not to scare the stuffing out of the candidate. It’s to learn more about them and their potential fit.


Done in a thoughtful and open manner, your interviews will set the tone for your future working relationship. These questions search for deeper understanding and authenticity. In many cases, there is no “right” answer.


Startups often have a charged and evolving environment where work relationships are they only constant. Let’s figure this out.

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