LESSON 6: Outreach – Most Powerful Question You Can Ask Copy


The Most Powerful Question You Can Ask

Networking is a funny business, especially when you are in job transition. Depending how long you’ve been looking, the pressure to find something, anything, can feel overwhelming. And if you are a naturally shy person, contacting and connecting with people you have never met can feel extremely uncomfortable. But you press on, drinking oceans of coffee with people you don’t know and will likely never see again. The one question burning in your mind at each meeting is, “Do you know of an opening for what I’m looking for?”

It’s not the best question to be asking.

While it might be the most natural question to ask, it’s not the most powerful one. The single most powerful question you can and should always ask in a networking meeting is, “How can I be of help to you, either personally or professionally?” Why is this the case? Below are four drivers of this most important query.


Oftentimes when we are between jobs, our self-worth takes a major hit. When we are asked the dreaded, “So what do you do?” question, we can mistakenly hear, “So what is your value?” and No Job equals No Value. Not true! You have a lifetime of experiences and relationships to offer the other person.


Similarly, we can come into a job-search networking meeting feeling like we are imposing on them and begging for their help. Establishing early in the meeting that one of your goals for the meeting is to see how you can be of help to them recalibrates the power dynamic in such a way as to put you on an even playing field with the other person. 

Be Genuine

Probably the most important element of this question is it MUST be genuine. When it comes across as a rote line you know you’re supposed to say, it is quickly perceived as such. Conversely, when the other person knows you actually do want to be of help, regardless if they take you up on it or not, you have just built an incredible amount of trust with them. The mere fact that you sincerely asked how you can help them speaks volumes about who you are and your intentions.

Personally or Professionally

Depending on whom you’re meeting with, the obvious ways of being of assistance to them may not be clear. If you sell electron microscopes and you’re meeting with an accountant, there may be little overlap in a professional sense. However, they are real people with real lives and real passions too. Are they involved in any charities or causes? (I’d love to support you in your Ovarian Cancer 5K Walk fundraiser). Did you learn something about them or their families where you could be of help? See the section below, Rock’s Fab 5, for more on this.

Networking is about building real, long-lasting relationships. Relationships are two-way streets where both parties seek to add value to the lives of the other. Think about the people in your life who you would naturally, even enthusiastically, want to help if they asked you for assistance.  Most likely, they are folks who have made deposits in your life. Genuinely seek ways to make deposits by asking, “How can I be of help to you, either personally or professionally?” The paradox of offering to help is often the best path to receiving help.

Rock’s Fab 5

One of my most valued mentors is Rock Robinson, CEO of Rock SOLID Sales Consulting.  A key principle Rock preaches is that you have to create a Connection, that turns into a Like, and that builds Trust….ultimately creating the foundation to build a Relationship with someone.  In the sales world, relationships help build opportunities for business.

But you can’t like someone if you don’t know much about them.  The simple process below is applicable for any new relationship and is most definitely not limited to salespeople. We just saw that in the section above with the Most Powerful Question You Can Ask, that is predicated on actually knowing something about the person to whom you are asking the question.  This is presented in a networking context but is really a life principle.

The basic idea here is to learn a bit about the other person and find some common ground.  Those threads of commonality create a bond.  The stronger the bond, the stronger the relationship. So, let’s dive in to see how you can easily move from, “I’m not very good at meeting new people” to “Wow, I'm so glad I met that person!” 

Remember, it’s all about how you ask the question.  Listen with the intent to listen.  The topics are not new ones, so challenge yourself to see how much information you can learn about someone that builds the foundation of a relationship.  Also, once you’ve perfected these questions, you’ll start to observe if they ask any of them about you.  Finally, experience has led me to generally ask them in this order:

Rock’s Fab 5

1. “Where were you born & raised?” (or “Where did you grow up?”)

It’s amazing how people connect with a geographic question.  Finding where someone grew up offers opportunities at multiple connections versus where do you reside now.  Again, it’s about connecting.  Have you ever traveled abroad and randomly met someone from your home country?  It’s amazing how you have an instant connection with them.  You speak the same language, have the same cultural norms, eat similar food, etc.  Similarly, when we meet folks from the same part of the world as us, (country, state, city, whatever), there is an immediate connection. “Oh, you grew up in the South! Don’t you miss the slower pace sometimes?” “Which borough in NYC are you from? Mets or Yankees?”  If you're from Cincinnati, do you prefer Gold Star or Skyline chili? It’s such a simple thing to learn about but the deep connection we have with our roots is a great way to move past talking about the weather.

2. “Family?” (or “Tell me about your family.”)

They will tell you what is important to them...I’ve heard about their pets, siblings, parents, cousins, etc.  Open-ended questions give you what more opportunities to connect.  You’ll notice immediately the question isn’t phrased as “Are you married?” “Do you have kids, grandkids, etc.”   Obviously, we don’t know much about this person yet and it could very well be they have recently gone through a traumatic life experience (divorce or something else tragic) that could make them feel uncomfortable. Moreover, it allows for personal definitions of “family”, for example LGBTQ relationships or people who consider their pets as members of the family.  I’ve learned about people with special needs children where I was able to introduce them to agency resources they didn’t even know existed.  That’s the kind of connection that lasts a lifetime.

3. “School?” (or “Where did you attend school?”)

Again, this open-ended question is asked in such a way as to allow for some grace depending on that person’s education level.  It allows someone to possibly offer they went into the military out of high school, or they went immediately to work.  Asking, “where did you graduate college?” may feel like a natural question for those in a professional line of work.  In Cincinnati where I live, many people here identify very heavily with their high schools. For others, they may not have completed a four-year degree and feel ashamed that they never finished.  This allows someone the space to say “I attended the University of Wherever” and still hold their head high.  One time I asked this of a new prospect and he answered, “In Massachusetts.”   It wasn’t until I looked him up on LinkedIn later that it turns out the school “in Massachusetts” was Harvard!  I still think that is one of the classiest things I’ve ever seen someone do.

4. “Tell me about your work (career) journey?” (or “Work background?”)

This is probably where most of us go first - “So what do you do?”  For the person in a career transition this would generally not be a welcomed question (I don’t have a job therefore I don’t do anything therefore my self-worth is zero).  But when the question is posed as “And your work background?”, it allows the person in job search to describe what their desired professional role is, even if they aren’t currently doing it.  Look for work connections - type of industries, job roles, F500, Family businesses, Company names, etc.

5. “What are you passionate about?” (or “What do you love to do when you’re not ….?”)

This question is also a humanizing inquiry because it is more about the heart.  The response might be a hobby, a cause, or anything else that gives you a major clue as to what this person prioritizes in their life.  Clearly, when we connect with someone at a heart level, it is one of those relationships where we feel like we’ve known them our entire life.  

You’ll notice that each of these is designed to elicit information in such a way as to show respect and honor to the other person. Rock’s Fab 5 are a great vehicle to move past merely transactional or sub-optimized acquaintances to ones that seek to add value for both people in more meaningful ways.  Start building connections by asking these questions today.  You’ll surprise yourself how like, trust and quality relationships will follow.