• Richie Crowley

The 6 Types Of Questions You Need To Start Asking People

Animals are impressive. They have consciousness and have developed methods of communication, but what separates us, the humans, is how elaborate our methods of communication are. We are not limited to snarls, barks, and growls to ward off threats, and we don’t build nests to express an interest to mate.

We have language.

Human conversation is the most sacred use of our language skills. It enables us to verbalize thoughts and share them with others. With conversation we are able to express love, gratitude, fear, and concern, host debate, and so much more.

Conversation also builds bridges.

If eye contact is an invitation to engage, or an expression of interest, then conversation constructs the foundation that a relationship will be built upon.

It’s in conversation that we explore each other, hoping to find shared interests and common ground. Similar to how salespeople schedule “Discovery Calls” we use first conversations to qualify each other out, and determine if we will continue to nurture our relationship.

Bluntly put, we’re evaluating each other and deciding how much effort we want to put into the new people we meet.

But, there’s a darker side to this. Less common in grocery store or local post office interactions, is the conversation you’ll hear if you go out on a Thursday night in your “work clothes”: What do you do? Where did you go to school? Do you know (insert name)?

A series of questions, presenting as attempts to find mutual interest and connections, masking a self-serving exploration of your value. Don’t be fooled, the hosts of these conversations are only listening to respond, not to understand. To combat these interactions, what I propose is that rather than racing to identify the role a person will play in our lives, and estimating the value they add to ours, we work to find comfort as we tread the waters of the curiosity pool.

We can do this with inclusive questions and intentional conversation.

For those who see a list title, click, and quickly scroll through to extract quick bits of info, I’m going to drop the questions in here for you now, but know that simply scrolling through this chunk of text and moving on has no purpose:

  1. Are you in a partnership?

  2. Do you have a running list of your top 3 restaurants in the area?

  3. Do you have any food or drink preferences or restrictions?

  4. Have you read anything exciting lately?

  5. Are you a fan of podcasts?

  6. What is the next most exciting thing you have coming up?

  7. What are you struggling with most right now?

  8. Do you have a preferred email address?

Without explanations, these questions can’t be asked with intention and have no utility. This list is a script you don’t know how to read.

For those who are still with us, the curious, let’s continue.

I’ve had great experiences with offerings, though not in the spiritual realm, and believe when we lead with an intention of providing service, we will reap the largest return. It’s important to acknowledge that the return is not always income and that I measure life through fulfillment and contentment, not wealth or material. These offerings have been done in many ways.

Once it was offering a piece of my writing to a company and granting them permission to use my words for their own content or in an email without asking for payment because I trusted the engagement and response their audience would have, and they’d send over a contract. Other times it’s been helping friends navigate LinkedIn to find a new job for fun because my days at a recruiting start-up taught me the secret nuances of LinkedIn. This happens with personal coaching as well, and consultants. The free first call is an offering, a conversation to truly discover each other and see if the service offered is appropriate. Only a handful of times have I come across people who charge for discovery calls, a strategy I disagree with.

So these questions are to be considered offerings.

Yes, you are looking to extract information, but you’re doing it with pure intentions and curiosity. Rather than the line of questioning populating “drinks after work” like an animal ready to pounce on prey, you are offering questions that will fill the arena of your conversation with kindness, vulnerability, and exploration.


Subject: Family Ways To Ask: Are you in a partnership? Do you have family nearby? Do you keep community locally?

By using the word partnership we are respecting all relationships. When we say wife to a man we imply a sexual preference, and when we say spouse to a person we place a value on marriage that sits above other relationships. Continuing, by asking if someone has family nearby, we are inviting them to share what they feel comfortable with, free of implications, and the final suggestion using community broadly translates to who is in your life?

These questions are important because they allow us to get to know one another, and explore the identities of someone you might one day meet. But also they are strategic. If you find out a person has a young child, maybe the next time you see a brilliant children’s book, you’ll send it to them. Or, if you learn they have a cousin in college, or a family member working in the city, you have permission to share relevant articles should one come across you. Actions, that confirm you were listening. Subject: Dining & Social Ways To Ask: Do you have a running list of your top 3 restaurants in the area? Do you have any food or drink preferences or restrictions?

Selecting one restaurant is hard, and a person will usually decide between 2 or 3 when asked to select one. But, when asking for 3 recommendations, they’ll expand the selection pool which increases the probability of overlap. In the follow-up question, the adjustment to lead with preferences rather than restrictions asks the question in a more inclusive way, as opposed to asking: Is there anything you don’t eat or drink. There are stigma’s around sobriety, and dietary decisions, and asking the question with the structure of the latter, can be confused with the expectation you will eat or drink anything. Again, these questions are strategic specific to building a relationship. Learning of their responses, you might then try one of the recommendations and inform them once you have, or invite them to a similar restaurant you might think they’d enjoy. Because you liked that, I thought you’d like this.

The follow-up question addressing preferences and restrictions will surface if someone is vegan, vegetarian, gluten-free, lactose intolerant, or sober. This is good intel. You won’t want to be inviting a sober vegan to a brewery barbeque. As a sober vegan (aren’t we annoying?) when a new friend is accommodating to my preferences when planning an activity, it is incredibly meaningful. Subject: Continued Education Ways To Ask: Have you read anything exciting lately? Are you a fan of podcasts? If so, can you recommend me a new show to look into?

We ask the first question this way to avoid cornering a person. When we ask what are you reading right now, it may make a person uncomfortable or embarrassed because they simply aren’t reading anything, today. But, when we include the word lately, it expands the window of time that they can select from, and including the word anything invites a person to respond with an interesting blog, article, or poem, not just a book.

In a similar fashion, we ask if someone is a fan of podcasts to replace what podcasts are you listening to. Podcasts are a new technology that most of the world’s population has yet to begin enjoying. At no point in a conversation do we want to embarrass a person for not being hip to a new trend.

The final question seeking recommendations transforms our conversation partner into a thought leader. A flattering light to be seen in.

And we can apply the responses we receive in several ways. We now have the option to read something new and discuss it, we can share a piece of writing they may enjoy (same vein as restaurants) or discuss past and future podcast episodes if they do listen to a particular show. You now have common ground in leisure.

Subject: Goals, Projects, and Plans Ways To Ask: What is the next most exciting thing you have coming up? How can I support it?

This question is a personal favorite. It transforms conversations by removing the restrictions of only discussing “work”, and invites a person into a larger arena where they are encouraged to share anything that excites them. Often times, they’ll respond with something of incredible interest to them that you have limited knowledge of, so again they become a thought leader and now a teacher (bonus question #2).

What’s next at work, is tedious and small. What’s your next vacation implies a potential level of wealth. This is the most open-ended question we could ask and gives permission for our partner to get excited about something personal that they care about.

The supporting question is not always appropriate but use your judgment. If a person is excited about a new song, listening to it may be support. If they are publishing an article, share it around for them, and if it’s a trip of sorts, find out how to follow along.

Subject: An Offering Ways To Ask: What are you struggling with most right now? What are you working through that you could use support with?

This is the most human question on the list. It’s a question that doesn’t pry and is asked with empathy. It’s also not limited to any subject. It’s truly human to human conversation.

On the Rich Roll podcast, I heard the founder of Cafe Gratitude talk about how they use this as one of the two questions (the second is in the bonus below) all restaurant staff ask each other before beginning a shift. This question is a reminder that our friends are our fans and invites vulnerability into a relationship Subject: Continued Communication Ways To Ask: Do you have a preferred email address?

Okay, yes, this question does imply that the person you’re speaking with has email. If not, offer to help set one up for them because email is the best and most respectful method of communication we have. Its field box encourages us to go longer than text, and it's desktop or mobile app access respects our personal lives. Email is less disruptive than text or calling and lets us share links and attachments in a cleaner way. In a time where the lines between business and social have been blurred, email maintains a boundary.

BONUS: What are you grateful for?

BONUS:What can you teach a person?

Now, this list may not be anything new to you, but I hope that it helps you think of better ways to be more engaged in conversations and your follow-up. What all of these do is give you a reason to follow-up with conversation that stretches past the archaic, “It was great to meet you” email.

You now know each other’s interests and it’s appropriate to check-in with each other about a new podcast, article, adventure, or just life.

You may now be making 100 new friends per day because of your certificate of wizardry in conversation that you earned after reading this (Email me if you haven’t received your certificate yet) so I thought I’d add a few tips on how to manage new relationships with respect and intention. I keep all my contacts in two places: An organized google sheet and Mailchimp. Mailchimp, an email marketing platform, is free for anyone with less than 2,000 contacts and their landing pages can be built out to be more than a capture form. Google Sheets continues to be the easiest and fastest way to input and organize contacts. Google Sheets also has an email sending add-on, Yet Another Mail Merge, that enables you to send personalized email campaigns to 400 people per day (YAMM has totally changed my networking life). For Google Sheets I keep my relationships organized with the use of headers: First Name, Last Name, Email, Cell, Location, Extras (where I put the goodies)

These two free programs host my newsletter, website, contact form, and have become a scrappy CRM. Another quick action is to follow a person on Instagram to keep up with their life, and find them on LinkedIn (Google Search: “Person’s Name, City, LINKEDIN”) and send a request to connect. All in all, I don’t know if this will change your life, but I know it has the potential to. Since transitioning my career and becoming my own champion, authentic and well-intentioned relationships have amplified my life, not just my career. The point of difference often is not in learning and retaining new information like this writing, but applying it. Few will have the stamina to. Many won’t. I’m curious to hear your thoughts and you know I reply to every comment so light the response section up! Richie. Human.

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