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5 Times You’ll Need to Know How to Ask the Right Questions

5 Times You’ll Need to Know How to Ask the Right Questions
5 Times You’ll Need to Know How to Ask the Right Questions


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Have you ever really wanted to work with someone, maybe a potential partner, mentor or team leader, but you didn’t know how to make it happen? Maybe you want to become more of a “people person,” learning to make meaningful connections or step into leadership at work.

No matter what goals you may have, learning how to keep communication lines open will create new opportunities, moving you forward in achieving your purpose in business. Here are five circumstances where you can use the power of asking the right questions to open doors and lead you to new opportunities and connections.

Related: How to Ask Truly Powerful Questions as a Leader (and Why It’s Important)

1. Unlocking new opportunities

If you’re meeting a potential business partner, mentor or team leader, you should have a few key questions on hand that go beneath the surface. Oftentimes, it isn’t easy to meet new people. Icebreakers usually consist of comments about the weather, sports teams or the commute.

Getting others to talk about themselves rather than just the usual give-and-take is an art and a skill. You can start with the old “Who, What, Where, When and Why” format of journalism articles. For example, you can ask “Who is your mentor?” or “Why did you start your business?” If you are collaborating with another organization, you can ask, “What services do you offer that I might need?” Questions that focus on these categories can reveal more quickly whether certain networking relationships will yield results for you and your company.

2. Getting to know your team

In the daily grind of business, it’s easy to feel unseen and unheard. Creating a culture of asking the right questions opens up your ability to get to know the person behind your team members. Whether someone is valued for their knowledge of technology, their sales savvy or their writing ability, we are all much more than the total of our skills. It’s important to learn your team’s passions, their vision for their future and why they are working for the company at this time in their lives.

You may learn things that set a team member apart from the rest — they might assist seniors or disabled people on their days off — but you will only uncover this valuable information if you ask. You might find out they have an entrepreneurial spirit and have a fun side hustle or family business. Or you may discover they travel — which could open you up to new vacation spots or expand the way you do your work. The right questions create a culture of respect, helping people reveal more of who they are.

Related: Life’s Too Short to Work With Incompatible People — Follow These 3 Secrets To Building High-Performing Teams

3. Knowing your audience

When you begin to bring team members into your circle, it’s important to know your audience. In other words, learn who you are dealing with and be open and inclusive as you engage with them rather than shutting the flow of communication down. Don’t ask questions that put them on the spot. For example, don’t assume your team members want to talk about politics or that they all love sports. Be inclusive rather than expecting everyone to agree with your position or perspective.

It’s important to make sure the person you’re talking to is a good recipient of what you’re saying. Giving people the space to be themselves lets them know that you appreciate and want to get to know the person they truly are. Like many people, you may not feel comfortable breaking the ice and engaging team members you don’t know well, but you can find help.

There are plenty of online sources offering lists of possible open-ended questions you could use, such as, “If you had a superpower, what would it be?” or “If you were a time traveler, what time period would you go back to?” Asking them to explain their answer will allow them to reveal their character in ways that the usual patterns of communication would not.

4. Asking interview questions

Whether you are interviewing a candidate for a job or doing a discovery call in consideration of a collaboration, asking the right questions gets the other person talking in a way that reveals what you need to know. In business, there are drivers and passengers when it comes to having a conversation. The driver is not the one who talks the whole time; the driver is the one asking the questions that guide meaningful conversation.

Business leaders ask interview questions to quickly learn who is and is not a good fit for the company. I often ask why the candidate wants to work for my business. I learn right away whether they have done any research or know anything at all about what we do. Asking a question such as “What do you hope to get out of this experience?” can reveal a candidate’s purpose. You could also uncover the strength or resilience of a potential hire by asking about a challenge they had to overcome in life. Asking the right questions in an interview can bring out the true character of someone you only have a few minutes to assess.

Related: The One Interviewing Technique Guaranteed to Get You the Truth

5. Getting to know yourself

Effective questioning does not always have to involve another person. Sometimes the relationship you need to work on most is with yourself. Having sincere thought-provoking questions you ask yourself monthly, quarterly or even daily can open you up to growth. For example, it helps to assess your progress in a company from time to time or even your motivation to provide the kind of service your position calls for.

Ask yourself the hard questions: Am I living my purpose? Is the lifestyle of a business leader for me? Am I happy? Keeping a journal or making notes on your phone can help you keep your heart and mind in alignment, making certain your personal goals and dreams are not swept aside by the tide of business. If you find being this honest with yourself difficult, you might find an accountability partner, someone with compatible goals. You could also search for a mentor to guide you in planning how to navigate needed changes in your life, especially if your deep questions reveal that you have deviated from the path you originally set for yourself.

Putting these five strategies to work can be a true game-changer for anyone who feels they are missing the human connection. Engaging team members, colleagues and potential employees with respect and grace can open doors and make your company a place where everyone wants to work.

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