Best Questions Executives Should Ask In An Interview

Cut through the fluff.


(15 votes, average: 4.2 out of 5)

Last updated: November 16th, 2023

questions to ask in an interview

Last updated: November 16th, 2023

Reading Time: 5 minutes

For a candidate, interviews seem to be a rather one-sided process. You field seemingly endless questions in a high-pressure environment, and the powers that be decide whether or not you are the right person for the job.

As a consequence, it may be easy to conclude that asking questions of your own is impertinent. Or you may find that when the inevitable ‘Do you have any questions for us?’ is asked, you are so overwhelmed that your mind goes blank.

Having sat on both sides of the interview table, I can say that the best interviews are the ones in which candidates ask questions.

Having a meaningful two-way interaction in which you ask smart, insightful questions makes the interview more valuable for you and your potential employer. You appear more engaged and prepared while gaining the opportunity to assess the company’s alignment with your personal brand and values.

The challenge, however, is to ask questions in a way that can cut through company spin and provide true insights into an organisation.

Here are the Top 10 questions to ask in an interview to both make a good impression and help you choose the right company.

(By the way, if you don’t feel 100% confident about your upcoming job interview, consider using our executive interview coaching services or our interview coaching services for mid-career professionals).

(Related: Why You Should Hire An Executive Resume Writer).

‘What will be my biggest challenges in the role?’

This question is intended to give you a broader understanding of the obstacles you may face, as well as their scale.

By gaining insight into factors not listed in the job description (e.g., internal politics, outdated IT systems or budget restrictions) you can see the role more clearly within the context of organisational dynamics and your abilities.

In addition to demonstrating to the interviewer that you are enthusiastic about addressing these challenges, it can also provide you with an opening to discuss similar challenges you’ve dealt with in the past, and how you’ve resolved them.

(Related: How To Prepare For A Psychometric Test).

‘How is success measured in this role? What are the KPIs?’

When you take on a new role, you want to be sure that the expectations are clear. Beware the interviewer who can’t provide a straightforward answer!

This question also pinpoints role priorities. Although a job ad or description may list multiple responsibilities, success in the role may actually only hinge on, say, four of them.

‘Can you walk me through a typical day?’

Knowing what you’ll be doing every day is important as it not only provides insight into the skills and strengths required but can help determine whether this is a job you actually want.

If you’re an executive who thrives in strategic, change-driven roles, it is better to know at the interview stage if the role is more BAU in nature before you accept a role you are ultimately unsuited for.

Also, if you receive a response along the lines of, ‘Every day is different’, proceed with caution. This could signal an ambiguous work environment where expectations are not clearly defined and could change on a whim.

‘What are you hoping the successful candidate will accomplish in the first 6 months?’

The answer to this question can give you a clearer picture of the learning curve expected in the role and the pace at which the organisation works. Do they expect you to slot into the role and start delivering immediately? Or do they anticipate you’ll need time to settle in learn the ropes before expecting tangible results?

Asking this question can give you a sense of the company’s vision for the role, and how it will develop over time. Additionally, it can reveal information about key projects you should know about before you sign the job offer letter.

‘Thinking back on the candidates who have previously filled the role, what differentiates the good from the bad?’

Asking this question enables you to get a better picture of where you stand in the hiring process without asking the question directly.

The answer also provides you with a more nuanced insight into what qualities the interviewer is looking for, and perhaps more importantly, what they are NOT looking for.

It actually cuts through to the crux of what a hiring manager is trying to achieve through the interview process. If handled tactfully, this question can also be an opportunity to steer the conversation to raise and address any concerns the interviewer might have with you as a candidate.

‘Can you tell me a story about something that happens here that wouldn’t happen anywhere else?’

Company culture is a major factor in job satisfaction. However, getting an accurate picture is not as simple as asking a straightforward question.

According to organisational psychologist Adam Grant, typical responses to direct questions tend to focus on company values but won’t provide meaningful insight into what it is like to actually work there.

By telling a story, however, interviewers reveal common themes around company culture. This could relate to leadership attitudes, how the company deals with conflict, big personalities or expectations around work/life balance.

In a market where a lot of companies can be all talk on culture, asking a more strategic question can help you understand whether they ‘walk the walk’.

‘What do you enjoy most about working here?’

Realistically, you are probably not going to get a completely frank answer to this question. However, you can get a sense of whether a response is genuinely positive or more reserved and tactful.

As it is a more personal question than most, it can also help you forge a more meaningful connection with the interviewer (particularly if they will be your direct line manager) and gain a better understanding of drivers and motivations.

‘Where do you think the company is headed in the next five years? What are its biggest opportunities?’

Gaining a bigger picture understanding of where a company is headed is critical to understanding your role within the broader organisation, particularly as an executive.

The answer should give you a good feel for whether the company is on a growth trajectory and whether there are opportunities for advancement. It can also give you a good idea of key priorities in the short to mid-term.

The level of detail in the answer is also an indicator of how company vision is communicated within the organisation. if the interviewer is clear on future direction and can provide details as to how the company is tracking to meet its goal, then this is a good sign. If not, proceed with caution.

‘What opportunities are there for growth? Do you offer any training or professional development programs?’

With the acceleration of digital transformation and a rapidly evolving workplace, the need for upskilling is greater than ever. Ideally, you want an organisation who is willing to invest in your development to ensure you can grow with the company and add value.

In a tight jobs market when salary growth is projected to be low, organisations are relying more on professional development programs as incentives to attract and retain talent.

Asking this question demonstrates you are keen to broaden your skillset and envision a long-term future with the company. It can also prompt the interviewer to highlight potential career paths and future opportunities.

‘What’s your timeline for next steps?’

Every company has its own recruitment process and providing timely answers to candidates is (unfortunately) not necessarily a priority.

Asking this question establishes a timeframe for when you can expect to hear back, and also gives you a good idea of a company’s protocols for follow-up. This will make it easier for you to check-in if a timeline passes with no response.

More importantly, asking the question can give the interviewer a sense of accountability, and prompt them to get back to you faster.

Final Job Interview Tips.

There’s no need to ask all 10 questions in an interview. You may find that some will be addressed in due course, so prioritise two or three questions to fill any information gaps.

It may help to ask questions strategically throughout the interview when the opportunity arises – you don’t need to wait to be asked. This demonstrates to the interviewer that you are engaged with the process.

Finally, although it does make a good impression to ask questions, be smart about it. Asking questions is not a substitute for thoroughly researching a company prior to the interview. For example, don’t ask anything that can easily be found via a Google search.

Accepting a role with an organisation and giving them the better part of your days is a big commitment. Ensure you make an informed decision by asking the right questions before, and not after, you take on a new role.

– Irene

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