Guidance for first-time leaders and managers
During the interview: Your first interview as a hiring manager

In my previous article on preparing for job interviews as a hiring manager, I mentioned that the battle is half won in preparation. Here is the other half of the battle, and the lessons I have learnt in the actual interviews.
We have all been there — the cold sweat, the waking up early to dress up smartly, arriving 30 to 60 minutes before the interview schedule, the 1001 ways we imagined failing the interview and more. Because we know how unsettling and uncomfortable it can be, as an interviewer now, aim to empathise with those whom you are interviewing. They are human just as you are, and they would really appreciate that all their worst nightmare did not come true. How do we show empathy?
Start with small talk to show you care

Compliment some details on their outfit (exercise discernment if the person is of the opposite gender) if it does stand out to you. Notice the little things and make genuine, small talk about them. If the situation allows, and the person is friendly from the start, you can also use their CV or portfolio to create small talk.
“That’s a really pretty pair of shoes!”
“Can I get you a cup of water?”
(Servant leadership in action)“Can I get you some tissue to make you comfortable?”
(If the person is sweating from walking to the office)“Would you prefer to have the air-conditioning turned off?”
(If the person is wearing a really thick jacket/appearing unwell because of the air-conditioning)“It’s so cool that you were working with National Geographic — can you tell me more about the coolest project you’ve worked on?”
(It doesn’t have to be a ‘middle of interview’ question)
This is important in building relationships. We should be interested in building and investing in relationships, and not just selfishly when a person is a “confirmed hire” or “confirmed employee”. Just as you are interviewing to identify if the person is a good fit as a team member, the person is also observing you, the ‘representative’ of the organisation, to see if they would like to work with someone like you in the future. There is no superiority in the interview process.
Genuine, small talk takes practice. If you are not in the habit of saying these things genuinely, practice it with a friend regularly so it does not come off awkwardly in the actual interview.
Tip: You know those “how are you’s” in the pantry? Practice waiting for the answer instead of walking off after asking, and practice answering the next “how are you?” personally rather than with “fine, thank you” (whether or not you feel the person is asking genuinely, do to others what you would have them do to you!).
Make sure the list of your interview objectives is nearby

This list can be either a physical list in paper (avoid using laptops during interviews where possible so you can focus), or a mental list.
I said in the previous article in this series that a list of questions might be irrelevant since every person may turn out differently in the interview. A chatty person might render your interview questions useless, for example. What I am referring to is a list of interview objectives, not so much a list of interview questions.
This helps you to stay on track with what you need to find out by the end of the interview, instead of being overly empathetic that you end up having a great chat with no interview objectives met.
The list could look like this (yours can look different):
- Find out the usual grind about job experience and past projects
- Ask required questions for this role (if already set by HR or the specific team)
- Ask about personal take/perspective on your industry
- Find out about self-awareness, collaboration skills, and personal well-being (I wrote about this in my previous article)
- Validate red flags found in CV/portfolio
Listen with empathy, talk less

As I said earlier, treat the person as a friend and a human like yourself. Just because you can be a potential ‘boss’ to the other person does not give you the right to act superiorly towards another person. This means avoiding asking questions without smiling, asking questions in a bossy manner, or making crude judgements.
Besides moving the conversation with your questions, try to listen deeply with empathy and interrupt as little as possible. Allow the person the chance to explore their thinking and share their perspective. Here are some good and bad examples:
BAD
Interviewee: “There was this project, a collaboration with a government agency that I really enjoyed. Although the project kickoff was messy, everyone was super onboard and we worked late each night till 3:00 a.m —
You: 3:00 a.m.?! That’s insane! What’s wrong with the project manager? Were you upset that they make you do that?
Tip: Don’t interrupt! You’ll never know what comes after and the depth you can explore about this person’s thinking.
GOOD
Interviewee: “There was this project, a collaboration with a government agency that I really enjoyed. Although the project kickoff was messy, everyone was super onboard and we worked late each night till 3:00 a.m for two weeks. I was very tired, but very happy, perhaps because we all wanted to give our best and nobody demanded it from us. I think work-life balance is a myth; what is work to a person could be life to another. Although I don’t believe in over-working, I don’t mind doing that when it is working for something I truly believe in.”
You: That’s an interesting take. Curious to know what would qualify as something you “truly believe in”?
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Notice that the interviewee went deeper when not interrupted suddenly, and it totally changed the direction of the conversation. Learn to listen deeply for their reasoning, reactions and guiding principles in order to go into depth. I first learnt this from Indi Young’s Advanced Training Course on listening deeply.
Notice reasoning, reactions, guiding principles

When the conversation contains reasoning, reactions and guiding principles, you would be able to go into depth. A quick definition by Indi Young, cofounder of Adaptive Path and respected problem space researcher:
Reasoning: Thought process, whys and wherefores, decision making, indecision
Reaction: Emotion, feeling, causes an action or decision or thought process
Guiding principle: Rule, philosophy, or foundational instruction for making decisions
Why is it important to go into depth? It helps you to understand a person deeper, better and more importantly, you can understand their purpose.
I once had an unfortunate incident with a person who reacted strongly when I asked this person, “What do you think is your weakness?” This was my all-time favourite question to get a sense of a person’s self-awareness.
The person got really flushed and shouted to me that even big companies don’t ask such questions and I should think carefully about who I am.
I had to calm myself down internally and remind myself that I need to handle this well, even though I was shouted at. I asked the person to calm down and explained gently that we often ask this question to understand people better, and we are in no way undermining the person’s abilities. The person later apologised for being emotional but walked out on me, admitting their disinterest in the job.
This person’s reaction allowed me an insight to their inner thinking and perhaps a not-so-good fit to the team and I am glad it came up in the interview rather than regretting that we hired the person.
Look out for questions from the interviewee

Most interviewees either have no questions or have basic questions such as working hours, and next steps after the interview.
Some of my best hires in the past ask questions that are thoughtful and strategic when I interviewed them, though this is not the main reason we hired them. There is something we can learn about the way they think, and where they are coming from in asking those questions.
“The mark of a really great designer is that every decision they’ve made has a purpose, has intentionality.”
— Julie Zhuo, Facebook VP of Design
Here are some questions I’ve got in the past (only three that I can recall, as most do not ask questions):
“May I know how I will be evaluated after this interview?”
This suggests that the person is not afraid of evaluation, is in fact confident of their evaluation and would like to know if the metrics would be fair.
“How is the process like for submitting content requests?”
This suggests that this person may have concerns for past processes they have experienced and would like to know details in order to ‘judge’ our process if it fits them. This is a fair question and we would do justice to answer them honestly.
“How is the culture like in this organisation?”
This suggests that this person considers culture as important and that is a healthy sign. More on this in the next point.
Answer questions about culture honestly

This is a question that I too have asked during my past interviews with my managers.
I consider this one of the most important phase of the interview when the spotlight shines on the interviewer and the interviewer would be tempted to make a sales pitch for your organisation.
You really don’t have to. I suggest that the best way is the truthful way. Be honest about the culture. Don’t hide things unnecessarily, but don’t gossip either. Take things on a collective level rather than on an individual level. Every organisation will have its issues and challenges, but what does matter is the spirit of working together to solve these challenges.
If you are not comfortable with the culture yourself, then you need to think about how to answer this in advance in a way that does not contain lies and yet does not betray your own convictions.
It is unbelievable that an organisation has everything sorted out. No organisation is perfect. To lie and paint a perfect picture is as good as losing the candidate — whether early or later during their probation when they discover the truth and leave.
Some people thrive in mess. I once met a person who preferred to work with an organisation that is messy rather than perfect, so that they can enjoy the challenge of straightening things up together. So don’t feel obliged to paint that perfect picture.
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If you have other tips for hiring managers during the interview process that is role-agnostic, please do comment below!
This is hopefully the first of many in the series of “My first try” at different things. I’m very thankful to God for the opportunities I had in the past years and looking forward to more learnings!