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Career Management: How to Ask the Right Questions

Updated on February 16, 2016

Learn to Ask Questions at the Right Time

When you begin a business relationship, either with a an employer or a potential customer, you want to ensure you are projecting your best you.

Questions seem innocent enough, but asking the wrong question at the wrong time can give your business associates the wrong impression. If you have a question, it's good to ask, but it's important to ask a question that will yield the answer you need. Also, you will want to ask a question that will ensure your question will not give off a bad impression to a person who might not know you very well.

First Impressions Do Matter

First impressions are pretty important in business. In order to manage your career effectively, you should build your verbal and written communication skills so you are effectively communicating throughout your business day.

In business transactions, you might only have one interaction with that person, and within that first five minutes, the person you're communicating with will form an opinion of you. In a sense, the person will be viewing you through a filter. Once that filter is being used, all of their interactions with you will be conducted under this filter. And, in business, this filter is very difficult to overcome.

Asking good questions at the right time is part of helping you project a good first impression. In business, it's not productive to ask questions like one would in a classroom. Asking the wrong questions at the wrong time could actually squelch your career ambitions.

Asking appropriate questions can help people develop great first impressions of you.

An Example

I heard this example from a literary agent I know. It's a great example of how asking the wrong question at the wrong time can flatten a growing business relationship before you even start.

Michael was communicating with a writer. The writer had a great start to his career. The writer had three books placed with small publishers, and had submitted a fourth to Michael for his consideration. Michael enjoyed reading all of the author's books and was considering offering the writer a contract.

The writer asked the agent a question before their business relationship had the chance to solidify. The writer sent this email to his prospective agent: "I disagree with the timing of the release of the book, and I am thinking of getting out of the contract. Can I buy my book back?"

Michael asked for more details regarding the nature of the relationship between the author and the publisher. The author stated that he likes the publisher very well, but he simply disagreed with the date of the book's release and wanted to know if he could get out of the contract, perhaps by buying the books printed from the publisher.

While this question seems innocent enough, Michael stated he learned a lot about the author from this question. "I'm very patient and understanding with inexperienced authors. It's tough to write and sell a book. The competition is fierce, and often, authors have to battle the specters of their own fantasies of how being an author is going to be. First-time authors don't really know what to expect and what they can realistically accomplish with their first books.

"However, this question put me on my guard. The author's question demonstrated to me, along with other facts I learned about the author, a few different things:

  • That he was willing to break contract and a good business relationship only because he disagreed with the date of the publication of his book. This is not a point to break an entire business relationship. This is a point to negotiate. What happens if I negotiate a contract with a publisher on his behalf? Is he going to do the same thing and look to break the contract?
  • How is he going to buy the book back when he shared with me that he was retired and living on social security? The two didn't seem to add up. Either the gentleman isn't operating in reality, or he's lying about his former career, or he's lying about being on social security. Either way, I can't present his work to a publisher when there is questions about his honesty or even his sanity and risk my own contacts or career in the process.
  • Self-confidence is one thing, but in the publishing world, any venue you can find to get your work out there is a good venue and not one to be taken for granted. Yet, here was this author, who had three other books that were in the process of being published, who was willing to throw away a perfectly good, well-established business relationship because he didn't understand that smaller authors had a better chance of success when their materials come out during the off seasons.

"There were so many ways the author could have asked this question, such as, 'I don't like the date my publisher picked for the release date of one of my books. What can I do to negotiate a better date?' That would have given me a better impression of the author because it would demonstrate that the author was willing to listen to the publisher's side and negotiate if necessary.

"This left me with no other option than to decline to take the author as a client."

This example is a good lesson. Asking the wrong question in the wrong way at the wrong time can squash your chances of success.

Are there ways we can ensure our questions are productive and not anti-productive? The good news is, yes, there are!

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Ways to Make Sure Your Questions Won't Harm Your Business Relationships

Here are some guidelines for you to follow if you feel like you need to ask a question during your business transactions and help you avoid pitfalls in asking questions.

Can You Answer the Question Yourself?

If you have a question, is it possible you can find your own answers? Many employers like employees who are independent thinkers and ambitious.

Instead of asking your employer or fellow employees questions, you can:

  • Refer to different manuals and resources your company has available to read.
  • Find the answer on the internet.

If you're trying to get a client to sign on with you, doing an internet search on your prospective client will help you avoid asking questions that your client might feel you should already know.

You may not be able to avoid having to ask certain types of questions. For these types of questions, the only way for you to know what the answers are is to ask the right person. Here are some examples of these types of questions:

  • Your employer's expectations for you.
  • Your prospective client's needs.

Ask Productive and Positive Questions

Unless you feel comfortable and have established a closer relationship with your colleagues, your employer, or your prospective clients, you want to use your words sparingly and choose your words wisely.

First, make sure your wording will yield the result you are seeking. If you don't know specifically what you want to say, you can ask a general question first, then narrow down your questions until you feel satisfied you have the answers you need.

For example, if you have a client, you could ask, "What are your business goals for this year?"

As he states his goals, you could ask questions that will help pinpoint and clarify the points the client is making. Base the questions directly on what the client states so you don't sound too intrusive. Sticking to the points the client brings up will help ensure you are not broaching upon a subject that the client cannot share with you.

If you are in a situation where you are not familiar with the people you are dealing with, ask questions that are merely to seek information. Keep them short, simple, positive, and direct.

You might want to take this approach if you are just starting a job and you're trying to seek out information so you know how to navigate your way around office politics. For example, you might want to find out which people to avoid in the office at a new job. However, asking this question directly might get you labeled as a gossip monger or judgmental.

Instead, you could ask, "Who do you like working best with in the office?" The question is a positive question. The people who appear on that person's list of best people to work with at the office speaks volumes, but the people who don't appear on that list is also a statement without it having to be expressed. If there is any negative information, the person you are speaking with might offer this information on his own. The impression you're leaving on the other person is still a positive one, because your initial question was a positive one.

Keep the Purpose of Your Questions Productive

If you're in the habit of asking questions to demonstrate how clever you are, you are walking a tightrope. You never know when someone might take these types of questions the opposite way of what you intended for them to demonstrate.

Moreover, asking questions of this type can cloud your thinking. It can demonstrate insecurity rather than cleverness.

Questions can often become tools of unproductive tendencies, such as, ways to establish superiority, passive-aggressive communications, and ways to needle a coworker you might not be fond of. This is where questions cease to be "just questions."

If you find that people are getting offended when you ask questions, rethink the way you ask questions. Their reaction to your questions can give you important clues as to the effect your questions are having on other people.


Asking productive questions can help your business relationships.

Asking the Right Questions Is a Smaller Part of the Big Picture

Asking productive questions in your daily business transactions is part of assertive communication. Asking productive, timely questions is a skill, and like all skills, it can be developed.

You might want to do further reading on assertive communication. Assertive communication, which means communicating in a nonaggressive and respectful style and maintaining an attitude of compromise and cooperation, and creating win-win situations, will help you in your personal life as well as your business career.

Not all questions are innocent. Think of the reason why you're asking the question.

Do you have a story of a question gone wrong?

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