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4 Questions That Will Build Rapport and Boost Your Relationships Tired of asking, 'How are you?' and hearing, 'Good. How are you'? Here are ways to connect and possibly benefit your business.

By Jeff Boss Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

Conversation feels robotic at times. The same old question arises again and again, followed quickly by the same old answer:

"How are you?"

"Good. How are you?"

Now, that's a response that is about as entertaining as watching grass grow.

Related: 6 Smart Techniques to Connect With Influential People

But the thing is, you shouldn't let these opportunities slip by. Every interaction implies an opportunity, a chance to make a/another lasting impression, a chance to listen and be a good friend. Every interaction is a chance for the little social butterfly in you to flap its wings.

And, as an entrepreneur, every interaction throughout your day is an opportunity to network, build relationships and increase awareness about your brand.

But, along the way, remember that there is both an art and a science to asking powerful questions. In his latest book Triggers, long-time executive coach Marshall Goldsmith distinguished between passive and active questioning. Passive questions are those which warrant a yes/no response and feel professional in nature, Goldsmith wrote. For example, say you're in charge of marketing for your company and your boss comes to you asking, "Did you make any progress today?"

The answer (ideally) is "yes," and there the conversation ends. The question was professional in nature (much like a restaurant server asking, "Did you enjoy your meal, sir?"), but it doesn't give you, the respondent, the opportunity to speak about the effort you actually invested.

So, instead, consider this:. The same boss asks the same question, but now adds, "Did you do your best to make any progress today?" Now, that's an active question. By adding, "Did you do your best?" your boss has allowed you, when you respond, to take ownership for your effort.

The takeaway here is, try replacing that boring "How are you?" or "how was your day?" query with any of the four questions below, to seize the opportunity to build meaning into your relationships. You can even add Marshall's tips if you really want to make an impact.

1. 'What did you do today that was memorable?'

This is perhaps not the ideal way for you to start a conversation with a complete stranger, since it causes reflection -- and that may be uncomfortable. But when this question does occur, the encounter can go in one of two ways: exploratory and meaningful in a good way, or unusually memorable in a weird and not-so-positive way. However, the good news is the positive connotation associated with it: You're asking someone to remember a unique event which he or she will also associate with you. Boom. You're in there.

2. 'How did you challenge yourself today?'

This question is a little more comfortable to ask because it gives the other person a chance to brag. By that, I mean the person has the opportunity to talk about himself or herself. That supports the findings from a study on human conversational behavior which showed that people spend 60 percent of their conversations talking about themselves. Of course, the way in which you pose the question is important. Tone and word emphasis play major roles in assuring the message sent is the message received. Try repeating different variations of the question to yourself with a new emphasis on each word to ensure you're on the right track.

Related: 7 Essentials for an Elevator Pitch That Gets People to Listen

3. 'What did you learn at [event]?'

This is a good one because it not only causes the other person to reflect but also conveys interest in him or her (from which this person derives value which is then attributed to your now-worthwhile conversation. Bingo.). You might have to wait to get into the conversation a bit to discover the best "in" for when to drop this bomber of a question; so, make sure there's a situation or event to reference. Otherwise, you'll be back to that awkward place where talking stops and weirdness begins. Bonus: Follow up with, "How will you apply [insert learning here]?" in order to really ignite value in the conversation and claim your newfound supporter.

4. 'What did you like about [insert anything here]?'

Well, maybe not anything. Stick within the boundaries of the conversation so you don't come across as scatterbrained, given to daydreaming or just downright arrogant. Don't get me wrong, I like randomness; randomness is good, but only when you know how it will land (i.e., be received). This question helps you identify the other person's values because nobody is going to speak fondly about something unfun like sitting in a dentist's chair.

What's important here is that curiosity is everything. Actually, genuine curiosity is everything, because it's easy to fake the intention behind an inquiry. So, approach every encounter with a curious mind and make a positive impression with your relationship "stamp." All kinds of benefits may result.

Related: An Expert's Guide to Steering a Conversation

Jeff Boss

Leadership Team Coach, Author, Speaker

Jeff Boss is the author of two books, team leadership coach and former 13-year Navy SEAL where his top awards included four Bronze Stars with valor and two Purple Hearts. Visit him online at

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