Your Interviews Are Boring

Make the hiring process entertaining for candidates… and effective for your team

Scott Lenet
Risky Business
Published in
9 min readOct 31, 2021


Image: Shutterstock

Have you ever participated in a series of on-site job interviews, moving from one meeting to another for a half day or even a full day of grill sessions? It’s exhausting, right?

For job candidates, these interviews can feel like Groundhog Day, being asked the same questions about their job experience over and over — by the end of the day, a job seeker is so tired of telling her own story that she doesn’t even want to be with herself.

I’ve thought about this problem a lot in my role as a venture capitalist, where hiring is usually one of the greatest challenges faced by my portfolio companies. When I hear people say, “Scott, you’re an investor, so you’re a Finance guy, right?” I tend to reply, “Actually, I consider myself more of a Human Resources guy.”

The “grueling interview” challenge persists because interviewers typically receive little training, few instructions about what to probe, and almost no coordination with those who have previously met the candidate. The result is an experience that’s uninspiring for the interviewer and a slog for the candidate. It’s why interviewers often fall back on trying to determine a vague notion of culture fit, which is an attempt to determine whether the candidate has an affable personality or would pass the “airplane test” that asks what it would be like to be stuck together for several hours.

In my experience, the philosophy behind an uncoordinated process is well-intentioned. Recruiters argue that by sharing information with the next interviewer, bias could be introduced into the hiring system in a way that may be unfair to candidates. While this can be true when interviewers take a forceful approach to prepping the next interviewer, the costs of siloed interviewing are probably too high: the hiring organization misses opportunities to gain deeper insights that inform decision-making, and the candidate experience is simply painful.

It doesn’t have to be this way.

Instead, interviewers can coordinate closely, building on information surfaced in each session to produce a dynamic and informative series of meetings that energize the best candidates and weed out those who would not be a fit for the organization.

Over the course of my career as a venture capitalist and entrepreneur, I’ve conducted more than a thousand interviews. Based on this experience, and borrowing best practices I’ve learned from multiple technology companies, I developed a sequential framework consisting of four ways to avoid boring your candidates to death:

1. The Diligence Interview

2. The Horsepower Interview

3. The Culture Fit Interview

4. The Functional Interview

Here’s how to conduct each type:

1. The Diligence Interview

This style is the closest to what most people would recognize as the standard interview, with a resume review that attempts to determine the extent of the candidate’s job experience.

However, where a “normal” interview mostly consists of a chronological review, the diligence approach more deeply investigates the candidate’s knowledge of what’s described on his resume. The name is borrowed from the venture capital process of due diligence, where a startup tells potential investors a story, and then we do our homework to determine what’s real and what’s fiction.

For example, if the candidate’s resume indicates having managed a marketing budget of $1 million, don’t stop there. Ask probing questions to see whether the candidate mastered the skill and learned from the experience: “How did you deploy the budget? What was the breakdown of the spend? What medium and messages performed the best? What did you learn? What were the results?” A candidate who has the skills you need will be able to answer these questions. A fraud will say things like “That was a while ago, I don’t really remember all the details.”

Strengths and risks uncovered with this interview approach can be useful to pass on to the next interviewer. If you are unsure whether the candidate truly performed the accomplishments listed on his resume, ask the next interviewer to follow up and provide a second opinion. These risks can also be addressed in subsequent interview styles.

To execute the diligence interview, it’s essential to have developed a job description that accurately matches the responsibilities of the role with the prior experience needed to perform the job successfully.

2. The Horsepower Interview

Most companies I’ve met want to hire smart people, but IQ tests are definitely a no-no as part of the interview process. How can a hiring manager determine if a candidate is smart enough to join the team?

Many interviewers use some form of brain teaser, a tactic that has been popularized by management consulting firms, investment banks, and technology startups.

Brain teasers can be divided into two main subsets: (a) the “a-ha” variety and (b) the “show me how you think” case. One is useful, while the other can create an unfair interviewing experience.

(a) “A-ha” brain teasers are the type that require a bolt of inspiration, and once you know the answer, you will probably never forget. “Why are manhole covers round?” is a quintessential example. If you’ve heard the stock answer, “so that they don’t fall into the manhole opening” it’s easy to remember the next time you hear the question. It’s certainly possible to ask a candidate to walk you through an analytical process to understand how he reached his answer, but the honest answer is probably that he knows or doesn’t. It’s more like using trivia knowledge as a substitute to test intelligence, and trivia isn’t a level playing field.

(b) On the other hand, “show me how you think” questions are specifically designed to test analytical capabilities. For example, “how many manhole covers are there in Manhattan?” provides a better look into how a candidate might break apart an unfamiliar problem. To answer this question, the candidate could calculate the number of street segments in New York using some basic estimate of avenues and streets on the island. With a guess of the number of manhole covers per street segment, the candidate can arrive at a solution. It’s not important to arrive at the correct answer, but to see whether the candidate can think on her feet and take a methodical approach to work through a problem.

To incorporate fair and consistent horsepower interviews, hiring organizations should articulate what types of analytical skills are most needed to perform on the job, and then develop a library of brain teaser questions that consistently test these traits. Many software development recruiting processes test the basics of debugging errors, for example. The horsepower interview needn’t be a stand-alone interview, and can be bundled into one of the other three types.

3. The Culture Fit Interview

In my experience, vague notions of culture fit sometimes provide excuses for lazy organizations to reject diverse candidates. Despite this risk, culture fit is important for any company to assess — the question is how to do so in a way that’s fair and consistent.

Understanding cultural fit is far more than deciding if a person has a fun personality or would be a good drinking buddy. It’s about matching the person’s work style to the values of the company and ensuring that the way each side works won’t create too much friction.

For example, my company truly appreciates responsiveness, and a client-service mentality is one of our core values. These aren’t reflected in job experience, they are personal characteristics that can be tested. In a culture fit interview, an interviewer can ask a candidate to describe tangible examples of exemplifying client-service, or how she addressed a difficult client challenge.

In one of my earlier startups based in Austin, Texas, we felt it was important for our team to be hands-on and not easily intimidated by messy experiences. At this company, my co-founder and I would take turns cleaning the bathroom, because we couldn’t afford a cleaning service. To test these traits, I would take a candidate out to lunch towards the end of the process at a seafood restaurant called The Boiling Pot. First I would make sure that the candidate ate seafood, and if not, we would pick another place to eat. But I liked the Boiling Pot because the restaurant prepared its shellfish and vegetables in one big pot, and dumped cooked crab legs and pick-and-peel shrimp onto a paper tablecloth that was changed between meals. I was frequently interviewing experienced executives who wanted to transition to a startup during the dot-com boom, and I wanted to make sure a candidate wasn’t too “fancy” to roll up his sleeves and peel his own shrimp.

To implement objective culture fit interviews, hiring organizations must have developed a job description that includes the personal characteristics needed to perform the job successfully, as well as an agreed upon set of company values that can be consistently tested. Cultural fit is also an appropriate subject for personal reference calls towards the end of the interview process.

4. The Functional Interview

This functional interview is also known as the case study, providing a practical test of whether the candidate can actually do the job. Functional interviews can be extremely valuable for both sides, since they give a true window into how the candidate works using real-world examples of what the job entails.

For example, if you’re hiring someone to work as a web developer, ask the candidate to code an example page in whatever language is used by the hiring company. There’s no clearer test of whether the candidate can do the job.

Functional interviews shouldn’t be undertaken lightly, because they can be a lot of work and pressure for the candidate. A case study is a good final, confirmatory step. If you don’t think a candidate has the expertise to do the job for which you’re recruiting, you should surface that during a diligence interview instead.

It’s also important to avoid using candidates as “free labor” by employing the functional interview in cavalier fashion. This is a real turn-off for job seekers and can be poison to your organization’s reputation. The idea is to test whether a candidate can do the job, not to take advantage of a potentially asymmetric power dynamic in the hiring process.

As with horsepower interviews, hiring organizations should articulate what types of core skills are most needed to perform each role, and then develop a library of functional interview case studies to test these traits consistently. For fairness, each candidate for a particular open role should be given the same case study, or one that is essentially equivalent. Candidates should be given the same amount of time to complete the requested task.

The company’s recruiting team and hiring manager should explicitly sequence these interview styles, informing each member of the interviewing team which type is being requested and why. Debriefing immediately after the interview can help the process build on itself, providing useful information and a more complete picture of the candidate’s potential fit.

While it’s critical to avoid unfair bias in the interview process by overly influencing the next interviewer, adopting these different “styles” can avoid redundancy when screening prospective hires. No candidate enjoys going from one meeting to the next, answering the same questions repeatedly. If your current process feels more like an interrogation than a two-way exploration of job fit, these tactics might engage candidates and build your company’s reputation as a challenging and interesting place to work.

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Scott Lenet is President of Touchdown Ventures, a Registered Investment Adviser that provides “Venture Capital as a Service” to help corporations launch and manage their investment programs.

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Scott Lenet
Risky Business

Founder of Touchdown Ventures & DFJ Frontier, USC & UCLA adjunct professor, father of twins, Philly sports Phan, Forbes & TechCrunch contributor