We all know how important it is to ask your own questions during a job interview, regardless of role or seniority.

Though as you rise through the ranks, it becomes absolutely essential to ask your own exploratory, thought-provoking questions, especially when interviewing for an executive-level position. Asking the “right things” demonstrates your abilities as a leader, a strategist, and an asset to the organisation’s leadership.

Yet interviews are a two-way street – you are interviewing the employer just as much as they are interviewing you. Sure the employer wants to know what you are going to bring to the company, but you want to know what that employer will bring to your life.

The questions listed here are intended to give you crystal clear insight into how likely you are to succeed in that role and at that company. They’re also intended to position you as a proactive individual who asks thought-provoking, truth-seeking questions.

A Quick Preface

I want to share a few words of advice before we get on with the questions.

Always prepare 3-5 questions in advance for any interview, tailored towards the role and what you know about the employer. Therefore, don’t try to shoehorn all 10 of these bad boys into one interview!

Be ready to use all six senses when employers answer your interview questions, whether they are on this list or not. If you smell BS when the employer answers any of these questions (hopefully figuratively, but I suppose also literally), then there’s obviously something they are trying to conceal.

The best interviews are engaging, two-way conversations with a natural flow. So if an opportunity to ask one of these questions arises – ask it. Don’t wait for the interviewer to say “so, do you have any questions for me?”

If the role involves you implementing change, seeing a project through to completion, or managing a team – these questions are all excellent. However, if you’re aiming for more practical or entry level roles, these questions may not be as productive for you.

But with all that said, on with the questions:

1. What are your expectations within the first 3 months/6 months?

The answer to this question should give you a clearer impression of the role – but there’s more to it than that.

You’re effectively inviting them to state what they are expecting you to achieve in a relatively short period of time. Their expectations may be totally realistic. They may not be. But it gives you the opportunity to make that assessment.

After all, you’re the expert. You know what’s possible and what isn’t. If their expectations are a little too high (or even too low), that could mean that they aren’t 100% crystal clear about the role themselves.

Sales functions are a great example here. Say you’re applying for a sales-adjacent executive role – a Chief Revenue Officer, for instance. Sales is pretty notorious for its reliance on monetary goals and expectations. So if a hiring manager has very immediate, sky-high financial goals when long-term, sustainable growth would be a wiser bet, that’s something worth knowing now rather than later!

2. What budget will I command for this role?

Or alternatively, if it’s a position that isn’t in charge of a budget, ask “what kind of budget is there for me to carry out my role?”

Whether you have direct control over purse-strings or merely influence over them, the amount in play will dictate how serious they are in supporting you to meet the role’s objectives. Again, their answer might be reassuringly realistic – or it might show their lack of expertise.

Only you can assess whether a budget is realistic for that particular organisation and their needs. Budgets are relative, after all – a medium sized non-profit is likely to have a lot less available cash compared to a large private firm.

But if the budget being offered feels too restrictive when viewed in context, the role might require you to make some difficult compromises.

Either way, you’re better off knowing now.

3. Who are the key stakeholders that I will be liaising with on a regular basis?

Raise your hand if you’ve had this experience before: you get on well with the hiring managers, recruiters, and interview panel, only to be introduced to a less than pleasant person whom you have to work closely with.

So therefore it pays to ask the question, “is there anyone that I will be working with/under who I haven’t met yet?” Don’t be afraid to roll this one out if you know you’ll be working with someone who seems conspicuously absent from the interview process. Your interviewers might be keeping them away on purpose.

After all, people leave jobs because of people.

If you do suspect that a key stakeholder is being concealed from you, dig a little deeper after the interview. You’ve likely already taken a look at the employer’s Glassdoor reviews, but do any comments there make more sense knowing there may be a bad egg in the mix? Do you have any LinkedIn contacts at the organisation who could give you an inside scoop?

4. What are the key challenges I’m likely to face in this role?

This is a great question as it shows you are thinking realistically about the role, but also keen to tackle those challenges head-on.

After all, none of us can avoid workplace challenges. But forewarned is forearmed. When we know about an issue on the horizon, we can put mitigating factors in place asap – or just make sure everyone’s braced for impact!

Their answer to this question can be informative when taken with answers to other questions listed here. For example, if you know what you will be expected to achieve within 6 months, but also that there may be a challenging situation around month 4 that could derail that progress, how will you prepare? Will you have any budget to fall back on to bring things back under control?

And if the interviewer or panel doesn’t know (or appears unwilling to share) any problems that might arise in the role, that can also be very telling.

5. How would you describe the culture here?

As part of your research into the role, you will already have a taste of what the organisation’s internal culture and values are like. At the very least, you may have a certain picture of the organisation from their own careers page or social media presence.

But it’s worth remembering that these are all promotional materials that are there to get you thinking positively about the company as an employer.

Asking your interviewer outright about the organisation’s culture can be quite the eye-opener. Does the question elicit any uncomfortable squirming or hesitation? Or is their response confident, content, and open?

Be cautious if the interviewer starts spewing meaningless platitudes like “we’re like family here.” Seek further clarification by asking how exactly they are all like family – force them away from the script and more towards the truth!

6. As an employee, how would you rate this organisation out of 10?

Your interviewer’s response to this question can also be incredibly telling. Don’t just listen to their words – watch out for non-verbal cues as they respond, too.

No workplace is ever 100% perfect, so if an interviewer responds with an immediate “10!!!” with little apparent forethought, that should probably ring alarm bells. Either they’re suffering from Stockholm Syndrome, or they’re lying to try and keep your interest. Neither is particularly ideal.

It’s likely you’ll have a few powerful people in the room. If you are feeling particularly confident, ask those individuals how they would rate the organisation out of 10. If they do say “10,” ask “would your employees say the same?”

If that leader thinks their employees would rate the company equally highly without much of a supporting argument (and with all of their knowledge of the company’s internal finances, politics, firings, and failings) then I’d personally treat that answer with some suspicion.

On the other hand, if their rating out of 10 is a little more realistic, then simply ask “what needs to improve in order to make it a 10?” Again, this gives you a picture of what might make your employment there challenging and whether you want to be a part of it.

7. What are the team dynamics and personality like?

Regardless of whether you’re going to be a part of a team or you’re going to be managing one, this can be a highly informative line of inquiry. Again, we’re trying to unearth any potential issues before we sign on that dotted line. Observe both what they say and how they say it.

Even pleasant and productive teams have off-days and personalities that butt heads sometimes. So if the interviewers try to paint an overly idealistic picture of the team (and especially if it feels like they are repeating a script or a corporate party line) then there is likely something about the team worth concealing.

But also be on your guard for a more honest response. If they mention specific team members in a negative light, this gives you an idea of how much they tolerate toxicity. If the team is a (hopefully hypothetical) breeding ground for toxic people, and the company is doing nothing about that, then now’s your chance to run in the opposite direction!

8. What career progression and professional development opportunities are
there here/in this role?

It’s always worth thinking about your professional future, and a good employer will be thinking about your professional future too. If you are keen to progress – not just in terms of seniority but by learning new skills too – this can be a very attractive prospect for the interviewer.

This question will also give you an indication of how flat the corporate structure is. Flatter structures have fewer opportunities to climb the corporate ladder, but often have more leeway to develop employees in their existing roles, giving them more knowledge, experience, and (sometimes) power.

The interviewers’ response can also give you some insight into how much of an open, sharing environment the company is, and how crucial employee development is to their employer brand.

When asking this question, always mention “development opportunities” rather than “training.” “Training” might be interpreted as you needing further help to carry out the role.

9. What’s your management style?

Direct? Yes. Uncomfortable? Yes. Important? Absolutely.

Obviously this should only be asked to anyone in the room who will be directly managing you. How they answer can be just as important as what they say – but also pay attention to the reactions of those present who already report to that person!

In my experience, most candidates will ideally be looking for a leader who clearly communicates the results they are looking for but leave the team to use their own knowledge and initiative to get those results. Many candidates also appreciate leaders who are approachable, and not afraid to work alongside their team in times of crunch or crisis.

But by and large, your assessment of their answer will depend strongly on how you like to be managed. Many of us hate to be micromanaged – but some people thrive in that environment. So be aware of your own personal preferences.

Our final question is a big one, and one that requires some self-examination before you use it. I hope you’re sitting down, because the prospect of asking this at an interview might bowl you over.

10. Do you have any reservations about my ability to perform this role that you can give me the opportunity to address now?

Told you it was powerful. So powerful that it comes with a warning: before asking this question, do your research into what might be perceived as your weak spots. As well as extremely thick skin, you need to be prepared to respond – whatever their answer might be.

The interviewers are likely to have a list of things they want in a successful candidate. And you may very well tick nine out of their 10 boxes. But without asking this question, you don’t have the opportunity to turn that 10th cross into a tick.

Do your research, know your worth, and be bold!

In Conclusion
The value of these questions is two-fold: they will hopefully set you apart as a conscientious applicant, but they will give you an honest view of what the organisation is like to work for.

You may have been tempted to look elsewhere with the promises of a fatter salary, a sexier title, or a better bundle of perks, but the most important thing about a role is that you will truly be happy and fulfilled. And in order to answer that, you will need to see a company for its true self – warts-and-all – before you accept the role.

Questions like those above help you to see a company’s true colours before it’s too late.

Though we can’t eradicate all bad employers from the job market, we can help you identify the right cybersecurity leadership roles for your specific expertise, career goals, and outlook – throughout the UK and USA.

We’re here to help make your next move a positive one, so get in touch with the team at Bestman Solutions today!

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