9 essential questions to ask your interviewer

As your job interview draws to a close, it is very common for the interviewer to ask whether you have any questions about the role or the company. This final part is just as important as the Q&A that came before, so you want to walk in with a few thoughtful, well‑considered questions ready. Asking smart questions signals that you are genuinely interested in the opportunity, and it also helps you picture what it would actually feel like to work there. In a city as fast‑paced as Singapore, this is your moment to sense check: is this really where you want to land next? At the same time, you need to do your homework — avoid asking about anything that is clearly stated on the company website, recent news coverage or easily searchable public information. 

We spoke to Nick Chow of Macleans Group, about the best questions he has been asked in interviews — and why they work so well. 

Here is what he shared. 

1. What would be expected in this position after six months?
 

“This question works for almost any role, especially when you are speaking directly to your future line manager. Nothing is more important than managing expectations early. In many local companies, the first six months are about learning the routine, understanding internal systems and getting to know the team and culture, and often this period coincides with the end of probation. The real ‘fun’ usually starts afterwards, when you are expected to add visible value. That is why it is crucial to understand what your manager expects from you at that point. Asking this shows you care about aligning expectations from day one and that you are already thinking ahead and planning how to succeed in the role.” 

2. Why has this position become available?
 

“This question tells you a lot about what is happening inside the company,” Chow says. A positive answer might be that the role is newly created because the company is expanding, which suggests growth and opportunity. If the previous post‑holder moved up internally, that is also a good sign that the organisation offers career progression from this role.” 

Say you are interviewing for an analyst role at a Central‑based bank. If the interviewer explains the role was created because the Singapore team is taking on more regional APAC coverage, that suggests growth and extra exposure, compared with a role that exists because three analysts have resigned within a year. 

3. What’s the future strategy of the company?
 

“This helps you understand what your longer‑term future there might look like, and what kind of projects or transformations you could be involved in. You can really impress by showing you have already researched their plans.For example, by asking about a specific growth initiative or market move you noticed in their annual report or media coverage,” Chow suggests. 

It is also important to check whether the company’s future roadmap fits your own priorities. If you value stability but they mention major restructuring over the next few years, that is something to explore further. If you are speaking to a local retail brand that plans to expand to other Southeast Asian countries via e‑commerce and pop‑up stores in Jakarta and Kuala Lumpur, you can ask how this cross‑border strategy will shape your role, from language requirements to potential travel. 

4. What do you enjoy most about working here?
 

“This is a warm, positive question that tends to open people up and gives you insight into company culture and what a ‘day in the life’ actually feels like. It helps you see whether their experience matches your values and motivations,” Chow says. 

For instance, a sales associate in a retail store might say they enjoy the fast-paced environment and the strong sense of teamwork on the shop floor, where colleagues regularly step in to help during busy periods and managers are visible and supportive throughout the day. You can then consider whether that kind of customer-focused, collaborative culture suits you. 

5. What would a typical day look like for the role being offered?
 

“This question can reveal a lot in a short time. It gives you a sense of how your time would be divided between different tasks — meetings, client work, internal coordination, admin — and what the company really sees as the core of the role,” Chow says. For professionals in Singapore, where long hours are common in some sectors, this also helps you judge whether the day‑to‑day rhythm fits your working style and energy.” 

If you are applying for an account executive role at a PR agency, a “typical day” might include morning media monitoring, client calls across different time zones, drafting press materials and attending evening events — a rhythm quite different from an in‑house role with more regular hours. 

6. How do you measure success in this role?
 

“This helps you understand whether success is clearly defined and recognised. You will get a feel for what the company prioritises, how strong its ‘performance culture’ is, and how mature its HR and appraisal processes are.  

Some companies are very KPI‑driven; others are more informal. Knowing how your performance will be assessed and celebrated helps you decide whether this environment will motivate you or frustrate you.” 

7. What does the company look for in employees?
 

“This question helps you gauge cultural fit. If the traits and values they mention — for example, collaboration, resilience, creativity, attention to detail — are ones you genuinely share, you can be more confident you will work well there. It may also give you a subtle read on how you have come across in the interview so far. Before you leave, it is a good chance to briefly highlight any of those qualities that you have but have not yet had the opportunity to demonstrate.” 

For example, a Singapore‑listed conglomerate might highlight “agility, bilingual communication and cross‑functional teamwork” as key traits, given their mix of local, China and overseas stakeholders. You can then respond by briefly linking your experience in Chinese–English projects or cross‑department initiatives to those qualities. 

8. Can you tell me a little bit more about the work culture?
 

This is an open‑ended question that does not assume what the culture is like, and it invites a more honest description, according to Chow. “It works better than something very narrow, such as ‘Do you dress down on Fridays?’. Sometimes interviewers struggle to define ‘culture’ clearly, so have a few follow‑up questions ready if needed, such as: How do you recognise and celebrate good performance? What behaviours are most valued here? How does the company encourage communication between managers and staff? “ 

Imagine you are interviewing at a fast‑growing fintech. The interviewer might describe a culture of hot‑desking, flexible hours and frequent product sprints, with most communication happening on Teams or Slack. You can then ask follow‑ups about how they support work‑life balance during peak release periods, which is a common concern for many working professionals. 

9. What do you look for in regards to people reporting to you?
 

“This signals that you are already thinking about how to work well with your potential manager, and that you are proactive about adapting to different leadership styles. It shows initiative, flexibility and a willingness to build a positive, productive working relationship from the start,” Chow says. 

For instance, a team head in a law firm may say they value juniors who flag issues early, manage deadlines across multiple cases. You can then echo how you usually update supervisors on progress and manage last‑minute requests, showing you already think about how to work smoothly with a busy manager. 

Asking strong, genuine questions will give you richer, more practical insights into whether a job is right for you — and at the same time, they help you leave a confident, professional impression as your interview wraps up.