5 Critical Questions That Will Lead You to Business Success


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Recently, my company was exploring a business opportunity in Australia. I’ve been there more than 50 times but found myself puzzled over a real estate term. I could have pretended to understand it so I’d look smart to everyone, but I asked what the term meant – and the answer changed our direction completely.

The experience taught me, once again, that when it comes to business challenges, being willing to ask questions is often the answer you need to succeed. No one is an expert in everything, so questions are an essential part of running any business. By asking questions and then listening to the answers and acting on them, even if you reach a different conclusion than they have, you are telling everyone around you that they are important, and you value their opinions.

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Great salespeople are excellent listeners

The consequence of not asking questions is obvious: failure. When you neglect to seek critical information, you put your project (or your entire business) at risk of failure, and your reputation suffers because you look like a know-it-all who places your own ideas above all else.

Not enough people understand this. Great salespeople are excellent listeners — they hear what the customer wants and then give it to them. Poor salespeople, on the other hand, consistently misread people because they haven’t learned how to listen or ask questions — or they’re just too busy talking.

It’s essential to ask the right questions, but you can’t hold back for fear of looking like you don’t know anything. Being willing to admit what you don’t understand can be more valuable than showing your authority. No one expects me to know all about legal issues or be a technology expert; that’s why we have a legal department that hires lawyers and have an IT department that hires computer experts. But being honestly curious about areas you’re not familiar with will lead you to the answers you need, and if your experts give you clear answers you can understand, you can be more confident you’ve got the right team in place.

5 Questions that can yield the answers you need

As the saying goes, we don’t always know what we don’t know. That can make it hard to come up with the right questions. But it’s not that hard if you start with these five basic inquiries:

1. What do you think?

You might be surprised how many employees don’t think their ideas matter to senior leaders. Asking for a team member’s opinion gives them permission to speak up with an honest assessment you might never hear if you don’t ask for it.

2. If you were me, what would you do?

This is helpful if you don’t know much about the subject being discussed. It’s a stronger way of asking “What should I do?” because it requires the employee to put more thought into their answer and to imagine the consequences.

3. Is there something I’m missing here?

If you don’t understand an answer or it doesn’t make sense, this is a diplomatic way of getting clarity. It gives you the responsibility for understanding rather than making the team members feel they’re not explaining things correctly.

4. Who else can I talk to about this?

This gives you the opportunity to expand your resources and relieves the employee of being completely responsible for the answers you need. Don’t ask in a way that suggests you’re unhappy with their responses, however.

5. Is there a better way to do this?

If you’re not satisfied with the answers you’ve received, this is a positive way of asking for better ones without denigrating the first answer and the person who gave it.

But asking questions is just the first step in seeking the information you need.

Related: How to Ask the Right Question in the Right Way

Stop talking and start listening

I’m not always looking for new information when I ask questions. I’m also seeking to understand my teams’ rationale so I can evaluate their decisions. Sometimes I’m just looking to confirm my own thinking.

That’s why I believe listening is such an important part of communication; once you ask the questions, you must listen to the answers and be willing to go deeper – “peeling the onion” with two or three or more queries that will get you where you need to be. I even wrote a short book on the subject; You’re Not Listening to Me! Learn to Communicate Better by Improving the Listening Side.

If you go in a different direction, asking intelligent questions and listening thoughtfully to the responses can minimize the team’s resistance. When you base your decision on the answers they’ve given you and you can explain the decision rationally, they are more likely to feel valued and respected. If someone gets upset or doesn’t accept your decision, it may be because you behaved like a prosecutor interrogating them on the witness stand – looking for reasons to reject their ideas without fair consideration.

Not all my questions are directed at my teams. My most productive one is often something I ask myself: What changes would someone else make right away if they were sitting in my seat? It’s not always easy to hear the answer, but taking an observer’s perspective and trying to see myself as someone else might view me has led to some surprisingly honest appraisals.

Remember, however, that what you ask is not as important as the mere fact that you’re asking. It shows you’re willing to admit you don’t know everything and you trust your team to help you choose the right direction. But it’s not just about image; ensuring you understand issues surrounding your business and have accounted for possible problems will make projects more likely to succeed.



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