What I’ve Learned After Holding One Thousand Interviews

May 17, 2023

What I’ve Learned After Holding 1000 Interviews

How to hire in startups and big companies

the interview process

Hiring is one of the most important things you do as a manager or entrepreneur. It will make or break your startup, team or project.

In the past 10 years, I’ve been hiring and building teams for startups and big companies, and I’ve got some valuable tricks up my sleeve in keeping a good process and hiring great people. Hopefully, sharing them with you might help you do the same.

How did I reach the 1K mark? I was the engineering manager tasked with building engineering teams at a startup and then, after its acquisition, building a sizeable European engineering office. For every hire I made, I had to interview 6–7 candidates on average, and I hired over 150+ people with various expertise, functions, skill sets, and seniority.

I tried to split this article into two parts:

Part I is focused on the interview process, what to look for in candidates and things to keep in mind before, during and after the interview and

Part II is focused on pitfalls, my biggest challenge and most likely yours and the million-dollar question: “How do I know if a hire will work out or not?”

Let’s take them one by one.

The interview process

In the startup days, we had a lean process as I was tasked with building up the team, so there were very few engineers that I would split the interviews with.

In startups, you need to build the team that is assembling the plane while in flight

We couldn’t afford a long process because we needed to focus on building products and hiring great people fast. Also, as we were a no-name startup, we didn’t have candidates lined up at our door, so taking them through a long slow process was putting us at a disadvantage from other more established companies.

A good interview process has to fit the company’s needs.

How long should the interview take?

It depends on the company and the position. Interview length varies; it could be from one and a half hours in startups and range to four/five hours in bigger companies. Startups usually have smaller interviews for the reasons I have presented above. Large companies could have multiple interview modules with various people on various subjects that can be scheduled over multiple days.

I remember being “interviewed” for joining the founding team at VectorWatch. It was a lunch with the Founder where he asked me what I could do.

Founder: ”Can you build the backend?”
Me: “Sure! What else do you need?”
Founder: ”I also need a mobile Android engineer…”
Me: “You are in luck, I also do Android apps on the side, I can take that on.”
Founder: “We may also want to do Windows Phone.”
Me: “I can look into that… it’s still mobile, right?”

And that was kind of it. I got the job.

Truth be told now, the Founder was an adviser to my previous startup, so he knew me well and knew what I could do, which is more than you would get from a two-hour interview.

Working with somebody gives you the best picture of their skill. At that point, you know their capabilities; you just need to assess their fit and motivation for the opportunity you are presenting.

Startup interviews

At a startup, I was holding one-and-a-half-hour interviews.

The first hour was more to see if a candidate was smart and got things done. I would give them an algorithmic problem to solve and ask some technical questions to probe their understanding of past technologies they had used. The questions and difficulty were always tailored to the level of seniority of the candidate.

I would try to determine if the candidate was curious and searched for answers. Mix curiosity with a passion for technology, and you can get an incredible hire that can diagnose complicated root causes and bring innovation to the company.

The second half-hour was to see if the candidate was a good fit for the startup.

I answer my “no asshole” question.

I don’t care if the candidate is smart. If they are an asshole and impossible to work with, the answer is no.

I look for their collaborative nature.

Ask about how they collaborated in a previous project and their role, and keep an eye on interactions they had and probe for concrete examples.

How they handled disagreements and worked through it.

It’s good to see how the candidate approaches this; do they push for settling things out, back off easily, or are they aggressive?

If they’re self-starters, jump on things and run with them.

In a startup, you are looking for self-starters who can get the job done fast and want to learn fast and grow their career with the same velocity that the startup grows — fast.

Who decides if the candidate is a fit?

In the early days, if the position was very senior, it would have been me and the Founder. After I managed to hire more folks in the engineering team, it would be me and the engineers holding the technology interview. I based my decision on signals from them and my experience with the candidate.

Big company interviews

Here the process is more thorough as there are multiple people covering various modules that are holding the interviews.

Depending on the role, there are modules of about an hour long: Coding, System Architecture, Program Management, People Management, Cultural Add and so on. The questions and how to hold a session are better organized; there is extensive training for interviewers and guidelines on how to rate answers and conduct the interview. At a startup, you most likely have to create the process and guidelines yourself if you want to scale.

The typical interview is about 4–5 modules of 45 min-1h each. There would be around 3 or 4 modules probing job required skills plus a session probing cultural add and soft skills.

Who decides if a candidate is a hire or not?

At the end, there is a debrief session with all the interviewers. It is a good way to get multiple perspectives and reduce biases. Now who decides depends also on the company. Typically it’s the Engineering manager’s decision based on the feedback from all the interviewers. There may be an additional step, and the Engineering Manager may need another approval from a more central committee to proceed to the offer stage.

What should you look for in candidates?

Most of the time, I get a question from fellow managers: what do you look for when you hire?

Joel has a short answer I liked from the first time I learned about it: Smart and Gets Things Done. It universally applies to startups or big companies, and the interview feedback is the answer to the following question:

Is the candidate smart, gets things done, and is a cultural add for the team/company?

I will try to break it down:

Is the candidate smart?

This translates into possessing critical thinking and having the foundations needed to perform in the industry (tech in most of my cases); does the candidate possess algorithmic thinking?

In the past, companies used brain teasers to assess this part. I don’t necessarily agree with that; I typically use some known algorithm problem. The candidate has to take me through their logic for them to demonstrate their algorithmic thinking and process logic. I want to see when they get stuck, what they do, how they re-think, whether they ask good questions, etc.

I try to keep the problem as close to reality and something that maybe the candidate has encountered or something practical that exists around us. I stay away from magic dwarfs that hold hands in a circle and pass a ball between each other types of problems.

Does the candidate get things done?

Here I inquire about past projects. I try to ask about a difficult project and situation related to a project they had in the past because I want to see how they approached it and if they were the driving force to get it solved. How did they achieve it?

Some candidates use the “we” word a lot. “We have done X, we have done Y”. While it is good because it seems that they are thinking of the achievements as a broader team effort, it is important to understand what the candidate did for the achievement. So don’t be afraid to ask more specifically what their role was and to drill down on their experience.

Is it a culture add?

You may have noticed that I used the word “cultural add” and not “cultural fit,” as it is highly used in the industry. What I mean by this is that you have to be careful of biases and not create a team that is not diverse at all. I won’t go into the mechanics here of why a diverse team outperforms a less diverse one, maybe in a future article, but what you should look for is culture add and not just culture fit.

Culture add implies hiring somebody that shows similar core values that you are searching for, which are deal breakers. It also means that the hire is not necessarily like everyone else on your team, as they may bring a different perspective altogether. Even thinking of this from a cultural add approach and not a cultural fit will start reducing some of the biases due to awareness of the subject.

An important thing to keep in mind is that

Being a good fit within an organization is a two-way street

The candidate has to be a match for the company and vice versa. If the candidate wants a 9 to 5 schedule and your startup requires crazy hours and deadlines for the next 2 years until break even is in sight, then you must be transparent.

Another thing to look for is if the candidate shares or exhibited values that you care about in previous jobs. Be mindful here; maybe the candidate didn’t have the opportunity to exhibit them due to context. An engineer that has worked in a consulting company may not have been in a position to “push back to product” because the client would have canceled the contract and they could have lost his job.

The no-asshole rule is important and will save you from many issues down the road. Usually, assholes don’t change easily or at all. Believe me, I had my trials with some, and they would end up quitting, leaving the entire team frustrated or, even worse, having half of them quit as well. If you make this mistake, you have to manage the person back on track or out. There is no other way.

Before, During and After the interview

Before the interview

It is good to book a time to prepare a bit. It doesn’t matter how proficient you think you are in holding interviews. I usually reserve 30 minutes in my calendar before the interview to have time to choose the questions, map a rough draft of how I will guide the candidate through the questions, look over past experiences and projects from their resume and just hit pause to the busy day that I had and get into the interview mindset.

During the interview

My advice is to take notes. Let the candidate know that you want to document things as best as possible and that you’re not doing anything else on your laptop so the candidate does not see this as rude.

If you have the draft from the previous step, you should fill in the blanks with responses to your questions, plus any other things you may discover during the interview. The interview map you drafted will keep you on track and not end the interview without having all the answers to decide.

After the interview

Refine your notes. We live such busy, chaotic lives full of interruptions that affect our memory. What you have discussed is mostly forgotten in the next 2–4 hours, and the next day you can barely recollect the details of the interview. You will just remember your decision, and most likely, it will be hard to recall the data that pushed you to that decision.

I usually block another 30 minutes after the interview to polish the notes, give another thought on how things went and document my decision.

What are the trickiest roles you have to get right?

It depends on the company. I would say every hiring decision is important to get right. The consequences of a bad hire may impact the team, the projects or even the company.

Getting the right talent is critical for a startup in the early days. At bigger companies, leadership positions are more tricky to get right due to the big impact they may have on a large part of the company.

A rule of thumb to see how important the role you are hiring for is to do a worst-case scenario. Ask yourself this:

What are the implications for the business if I mess up this hiring decision?

Based on your answer, you will know the margin of error you are allowed and mitigations you can put in place to ensure the hire you do is successful and will work out.

Stay Tuned for Part II

This concludes the end of the first part. In the second part, we will go over pitfalls, one of the biggest challenges in interviewing that many seasoned interviewers face and how hiring managers could know if a hire will work out. If there are things that you would like me to touch upon in part II, please let me know in the comments below.

What I’ve Learned After Holding One Thousand Interviews was originally published in Entrepreneur’s Handbook on Medium, where people are continuing the conversation by highlighting and responding to this story.



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