The 20 most valuable lessons I learned in the first 20 years of my career …

Chapter V — Never Ask Leading Questions

Benjamin Wettlaufer
8 min readJan 11, 2022

2021 year marked my 20th working anniversary, including my three years apprenticeship. A fifth of a century and more than the half of my life. In these twenty years, I had different jobs and different roles. From apprentice to middle management. In the course of this year, I want to take some time to look back, share my journey and mostly, what I’ve learned so far.

Since I work in Berlin I did a lot of interviews. I don’t know the actual number, but it must have been hundreds. Especially the last four years have been quite intense. I believe I’m a decent interviewer. Not great, but there is one thing I’m good at: I’m authentic. I don’t like to pitch so much in interviews, out of a very simple reason: If you wheedle someone into a position, tell them what they like to hear even though that’s not the reality, sooner or later, they will see and leave in frustration and you gained nothing. Hiring is a marathon, not a sprint. Losing a new peer early on because you over-pitched, in the end cost you more than keep hiring. After some years where I didn’t really know what I was doing, I found my own style and I’m quite okay with it. These days I’m getting very positive feedback from both, peers I do interviews with and also candidates, even though we might not ending up working together. That’s pretty cool, especially as this was not always the case. It’s a process, like so many things else. So in this chapter, I want to share some of the things I learned so far.

Only practice, practise

I never really got any extensive interview training. So my first tip would be: get one, if you can. Or two. Or three. In general, if there is a training you can get, get it. What’s the worst that can happen? You lost some time — work-time! Conducting an interview is a challenging thing. It’s more than just asking question or listening, while I believe that the latter one is even more important. Because it’s people you deal with, an interview can always go in thousand directions. It can be useful to at least hear about some tactics, learn about some patterns that can occur and think about, what exactly you try to find out and how. Having at least an idea of strategy, can be useful. Don’t be so arrogant to assume, you are a natural talent at this. I’ve done quite some interviews meanwhile and I still fail from time to time miserably, not being able to unlock anything that the CV hasn’t told me already. I got some short, superficial training sessions over the years, but nothing really comprehensive. One thing stuck with me though and that is what’s given this article its title: never asked leading questions! This is an all too common trap, I believe. There is a person you like, the interview is going well and you give the person basically the things she or he needs to answer the question in way you like. Basically tell the person, what you would like to hear.

“And I assume one of your most important principles is not to repeat yourself, when you code, right?”

Don’t do that, let the person answer the question. Ask open questions, forgo the temptation to show the person the direction. Any kind of direction.

Cool, and then?

Another important thing is to ask follow-up questions. That‘s an easy one that especially fakers like to avoid. Depending on the role, it is very easy to thoroughly drop some buzzwords as a candidate to appear extremely knowledgeable and experienced. So try to connect these buzzwords to actual experiences, real life examples, to see if there is something behind that. Lying on the spot is difficult, only a few are capable of doing convincingly, without getting nervous or aggressive.

If I may …

Another trap, is the “I-just-talk-a-lot-while-not-actually-telling-you-anything” kind of candidate. They are very dangerous. They overtake the conversation by just talking the whole time. They are normally super likeable, you think you have a good conversation, except you don’t. The person is leading the conversation, filling the time with a lot of bla bla without giving you the chance to ask any tough questions and all of a sudden, time is up. As they are nice and funny, you don’t really dare to interrupt them. The most frustrating interviews are the ones, when I realise, that I haven’t learned anything about the candidate and that the person is as mysterious and unknown to me, as before. Maybe even more. This is not just on the candidate, I’m mad at myself, that I was not able to break the flow.

Where do you see yourself in …

Some like to ask some tough questions. While I do have some standard questions I’d like to ask (only when there is no flow to be honest), I don’t have an arsenal of tough questions. My goal is not to “break” the candidate or to make the person sweat, my goal is to see if she or he could be a good fit. If I’m sceptical if the person is who she or he claims to be, I will ask some direct and annoying questions, but most likely, we don’t even get to that stage. Although with me, we could, as I often invest the time for a first call, even though I’m unsure or sceptical. I don’t really like to judge people from a small piece of paper, when a personality is so much more. Maybe you are great, but you totally suck at maintaining a proper CV. For most positions, I’m after a certain mindset and not only a collection of skills. Skills can be learned, a certain mindset is there or not.

Preparation is everything. Or nothing.

To be honest, I don’t prepare much for an interview. The fact that we have an interview means, I studied your CV and found it interesting enough to get to know you personally. CV’s are boring, they don’t really tell me, what I need to know. So I screen them, check maybe some external links and write down some observations. Mostly for things that are interesting (like a very unusual or wild CV) or for things, that doesn’t make sense to me. I trust that if the person might be a good fit, we will have a meaningful conversation, where both of us learn enough to decide if this can be a match, or not.

Dynamic hiring

I was always interested in the bigger picture. So lately I got fascinated by the concept of a capability based organisation. In Germany, companies are still quite hierarchical, based on departments, thus silos. A capability map tries to break that, regardless of departments it makes visible what the company is made of and what the people are capable of. Such capability map can be turned into heat-map for teams, telling the leader in which areas a team is strong and in which, the team is weak. An interview is normally a one-on-one thing, but it helps to have in mind what the team needs and not just, which position is vacant. Every new hire is a new opportunity to not just fill a vacancy, but to bring something new to a team, the department or even the company.

Different kind of processes

There are various ways to perform an interview of course, but if you want to break it down, there are two kinds: You more or less only ask questions, hardly say anything and try to get as much information from the candidate, as possible. Mostly those, the candidate doesn’t want to share willingly of course. Or, you try to make this an honest conversation about what you are looking for, what the candidate is looking for, what are the challenges with the position you want to staff and if this is something, the candidate is interested in and capable of. I prefer the latter one. Not that the first one is not honest, but I believe, the latter one creates the better outcome. In my interviews I paint a very honest picture about what we are able to offer, who we are and what not and what are the challenges with the role, team, project or product. I am as honest as I can be about the obstacles with the offered position as I mostly look for a certain mindset. Simply put, I try to hire passionate problem solver. People, that are not just limited to their expertise, that doesn’t expect everything will be cool all the time, but that like to zoom out and take responsibility not just for the problem at hand, but that help me to create a great team, product or else.

For me that works quite well and I managed to make some exceptional hires this way, but you could also argue, that it is the candidate, that needs to convince me and not the other way around. That by not telling the person anything, she or he needs to ask the right questions to paint the picture on her or him alone and you only correct, what they assume wrongly. Maybe, but I don’t think that this kind of “interrogation” work anymore.

Tell me something new, please

Most candidates start to recite their CV, when I ask them to tell me something about them. Why are people doing that? I read the CV and found it interesting enough, otherwise we would not have this conversation. This question, this moment is your chance to tell me something, which is not in there, something a CV can’t tell, something unique, something I should know about you as an expert but mostly you as a person. I wonder, why so few take this chance an instead, start to read me their CV.

Only time will tell

One of the most important insights tough is, that no matter how tough your interview process is, you will only really get to know the person, once you work with them. That’s just a fact and a risk, both parties take. An interview gives you a glimpse at a person, an impression, the rest is choosing to believe that this could work. Also from both sides. People are too complex as that you can figure them out in a few minutes or hours. Best you can do, is identify if there are any red flags. The rest, is a matter of time in the end.

P.S. Originally I planned to publish the whole series in 2021 of course. Due to reasons, that was not possible. I was thinking to just change the title and make it 21 lessons, but I decided against it. Things do not work out all the time, plans change, that’s fine. The learnings are still valid, even if I’m behind my schedule. This year, I will be hopefully able to finish it.

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Benjamin Wettlaufer

Berlin based rascal working with #OetkerDigital, former #ZalandoTech. Passioned for #tech, #design, #politics and #movies. Opinions are my own. ENG / DE