5 Tough Questions You Should Ask Prospects

Marketing Intelligence 13th, Nov 2013


Despite being an essential aspect of growing your company, most people do not enjoy hiring new staff. The reason for this is simple: it can be a difficult and stressful process for you and your team to find, train, and get used to working with a new coworker. To smooth transitions and ensure your newest team member is the best possible fit for the position, it helps to start by asking the right questions during the interview. The more difficult questions will tell you the most about a prospect so here is a list of 10 great but tough questions to ask during your next interview. We’ve also included some ideas about what to look for in an answer.

1) What is your biggest weakness (that is actually a weakness)?

This question has been used for many years and in virtually all industries and many people have taken to turning it into another chance to self-promote and making it seem like a worthless question to ask. Make it clear you want a real answer and see what they say: we’re looking for honesty and self-awareness here. The best answers will include ways in which they are trying to improve upon an actual fault.

2) How would you handle a coworker or boss who consistently stole credit for your ideas?

Most people do not enjoy office drama and it is important to get an idea of how your prospects might handle difficult situations with their coworkers. The answer they provide can help to identify their attitude towards recognition and internal competitiveness. Good answers should include non-confrontational strategies but also demonstrate a desire to be recognized for their contributions. Prospects who appear too unconcerned with receiving due credit may be lying or simply demonstrating a lack of ambition.

3) Would you rather work for a boss with a hands-on approach or one who lets you take the reins?

Unless your prospect has inside information on the management style of their potential supervisor(s), the way they answer this question can be extremely telling. A good answer should emphasize flexibility and an ability to work with their supervisor in the way the supervisor desires. Good prospects will likely describe a strategy to identify the work habits of their boss and incorporate that in their own habits.

4) Describe your dream job. (Or describe your idea of job hell.)

Both of these questions really address the same topic and it is up to you which one you prefer to use. Asking a prospect about their dream job can help you establish how interested they are in the position and how committed they will be in the long run. It will grant insight into their motivations and goals and allow you an opportunity to judge how well their aspirations fit the role you are considering giving them in your company. Inquiring about the opposite can allow you to establish what parts of the job they may be averse or tasks they may baulk at. Try to read between the lines and see what they are really saying: an admission that they dislike monotony may be a sign that they grow bored easily, for example.

5) What if you work there for several years and do not receive a promotion?

Good employees will have a balance of ambitiousness and practicality. They will want to succeed and be recognized when they do a good job but they will not expect a gold star for each task or assignment. Establishing your prospects attitudes towards promotion is key to deciding if they will fit within your companies’ structure. An ideal prospect will be happy to grow in their position, learn new things and implement their learning for the benefit of the company; they will be less focused on rewards and more focused on their role in the success of the business. Ambitiousness and a drive to take on new responsibilities to better serve the company is great. Being motivated only by the possibility of advancement is not

These are only a handle of ideas to get you started. Think about what information you would love to have had about your current or past employees before you hired them and frame your questions to address those issues.

By: Steve Toth

2 thoughts on “5 Tough Questions You Should Ask Prospects”

  1. This is a great article Steve! However I did notice a typo in your last header. I believe the word intended was “receive” or “have not received”.

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