Ever found yourself in a situation like this?

You’re in the middle of a great meeting with a new connection—let’s call him Michael—and you see the potential for a highly-valuable, mutually-beneficial relationship.

Wanting to make a good impression (and lay a strong foundation for the relationship), you wrap up the meeting with an attempt to uncover the challenges he’s currently facing to see if you can help. And despite the best of intentions, it’s at this crucial moment that you make the common (but grave) mistake of asking, “Hey, before we wrap this up … How can I help you?”

Wrong move.

Am I really saying it’s wrong to offer your help? Absolutely. Let me explain.

Don’t get me wrong: I understand your offer’s coming from a genuine desire to provide value, and there’s nothing wrong with that. In fact, that’s the heart of Positive Alacrity and the foundation of great relationships.

The problem is, most people go about offering help in the worst way possible and, as a result, end up not helping as effectively as they could (if at all).

If you really want to provide value to the other person, it’s time for a new approach; and that starts by recognizing the faults in using the “front door” “How can I help you?” tactic most people use.

Why “How Can I Help You?” Just Doesn’t Work

What is the “front door” approach?

In essence, it means taking the quick, easy, and relatively-thoughtless method of simply blurting out, “How can I help you?”

We all understand the intentions are good, but in this case the implementation is bad; and if you really want to contribute something meaningful to the other person, this isn’t the way to do it.

Why? Because most people have a two-fold reaction to this approach:

  1. First, they become a deer-in-headlights. Ever been asked a question you weren’t prepared to answer, and found yourself blurting out the first thing that came to mind? That’s what often happens here. The other person will either offer a knee-jerk “I’m fine, thanks,” (because they don’t know what else to say) or they’ll come up with some low-quality request just to answer the question.
  2. Second, they may protect their pride. When you ask someone how you can help them, you’re implying they need help in the first place. To them, accepting your offer means admitting both to themselves and to you that they need support. And if this is a relatively new relationship, you may find people simply aren’t willing to admit this (even—and especially—if it’s true).

Keep in mind: Most of this process is entirely automatic. They aren’t consciously choosing to subvert your offer, that’s just what they’ve been programmed to do. And when you think about it from their perspective, it’s pretty easy to understand why the “front door” offer of help often falls flat.

How to Offer Help in a Meaningful, Relevant, and Valuable Way

So what’s the right way to offer help?

The way to a) increase the likelihood that your offer will be accepted, and b) give you the opportunity to provide real, tangible value to the other person?

There are a few things you can do, both before the meeting and as you’re wrapping up. Let’s take a look.

#1: Know Your Value (in Advance)

Do your homework beforehand.

Never go into a meeting blind.

Spend a little time either a) creating an Icebreaker Profile (if this is the first time you’re meeting with the person), or b) reviewing your notes from past Meeting Debriefs.

How? Perhaps the best place to start is Accompany. Accompany will give you a bird’s eye view of the person you’re meeting with, showing you …

  • If they (or their company) have been mentioned in a meaningful way in the news,
  • If they’ve recently published any blog posts, and
  • Show you their most recent tweets.

Beyond Accompany, you can also scour their LinkedIn and Twitter feeds to see what seems to be most important to them right now.

With about 5-10 minutes of research (which could easily be outsourced to an EA), you should have enough context to identify potential challenges, passions, or interests.

Once you have that, ask yourself: How could I leverage my resources and network to offer something of value? Here’s a few examples of things you could offer:

  • IntroductionsWhen you offer an introduction, you’re not just making a connection; you’re delivering a positive experience and potentially even a breakthrough opportunity. Remember: The only way to reach your fullest potential is through relationships—and an introduction to someone in your network could be exactly what this person needs.
  • Value payloads. A value payload is any piece of content—such as an article, book, podcast, or video—that you find valuable and believe the other person will appreciate as well.
  • Experience-based advice. If you notice they seem to be facing a challenge you’ve recently overcome, consider offing your advice. For example: Maybe you see they linked to a job listing on Twitter for a VP of Sales. If you recently filled a VP of Sales role, share your experience and best practices.

A note on that final piece of value: 

Don’t offer unsolicited advice.

Even if you think you’ve got the perfect solution to a problem they seem to be facing, always ask permission. Here’s an example of what you might say:

“Hey, I noticed your listing for a VP of Sales on Twitter. I actually just filled that position in my firm about six months ago and, if you think it’d be valuable, I’d be happy to share what worked for us. Is that something that would be valuable for you?”

#2: Master the Second Dart

Assumptions are the enemy of value—and when you assume you know what the other person needs, you run the risk of appearing presumptuous and even totally off-base (especially in new relationships).

So even if you’ve done your research beforehand, use this meeting as an opportunity to confirm your findings and deepen your understanding of what this person needs—and be open to the possibility that it isn’t what you expected.

Perhaps the best way to do this is to lead the conversation through questions. The key here is to ask them in a way that leads to truly valuable, insightful answers. So instead of shallow yes-or-no questions, focus on questions that dig deeper into the professional challenges and personal interests. For example:

  • “What are your top 3 goals for the coming year?”
  • “What do you do to recharge and avoid burnout?”
  • “What have you found most difficult about your role?”

But don’t stop there. The first question, no matter how meaningful or genuine, often results in surface-level answers. After all, you’re just warming them up to the topic. That’s why I advise you …

Never fire off a question alone; they should always be asked in pairs (or more).

By asking follow-up questions—or what I call Firing the Second Dart—you move beyond surface-level answers to something more deep and meaningful. Let me give you a few examples of strong Second Dart questions:

  • “What makes you say that?”
  • “Why is that important to you?”
  • “What’s your favorite thing about that?”

You’ll know you found something truly meaningful to them when their eyes light up, their smile reaches their eyes (rather than staying confined to their mouth), their energy level increases, and their body language appears more open.

Wait: What Should I Be Asking About?

Broadly speaking, you’ll want to use questions to uncover two different types of information about the other person: Professional Challenges and Personal Interests/Passions. Let’s briefly talk about each.

Professional Challenges

Professional challenges are any career-related hurdles the other person is facing. For example:

  • Joe is trying to fill the CMO position at his firm.
  • Mary is currently working on improving her delegation skills.
  • Tom would like to grow his team from 10 to 50 by the end of this year.

By understanding someone’s professional challenges, you can leverage the vast knowledge and resources within your network to try and help them overcome that challenge.

Here’s a few questions you could ask to start to uncover someone’s professional challenges:

  • “What do you perceive as the most challenging aspects of your role?”
  • “If you could accomplish one thing on your list of things to do, what would that thing be?”
  • “What accomplishment would like to have achieved within the next few months?”

Personal Interests/Passions

Personal interests/passions are those things that someone is genuinely excited to talk about, and often something they have a wealth of knowledge around. For example:

  • Annie enjoys kitesurfing during the summer.
  • Rob travels to a new part of Europe at least once a year.
  • Amber is trilingual—English, French, and Spanish—and is actively working on mastering Swedish.

Understanding someone’s interests and passions allows you to connect with them on a much deeper, more personal level; and enables you to move this person from simply a “contact” to a genuine relationship.

Here’s a few questions you could ask to start to uncover someone’s personal interests/passions:

  • “What would you spend your time on if you had unlimited time?”
  • “What did you do this last weekend?”
  • “If I were to talk to someone who knows you outside of work, how do you think they would describe you?”

#3: Forget Active Listening—Listen Empathetically

We’ve talked about active listening before, and it’s an incredibly valuable skillset. But providing true value to someone requires something slightly deeper: Empathetic listening.

It’s about more than just hearing what they’re saying. Listening empathetically means feeling what they’re feeling; putting yourself in their shoes and asking, “In this situation, how would I feel? And what would be most valuable to me under these circumstances?” 

The ability to imagine what someone else is feeling—even if we haven’t experienced it ourselves—is critical to empathy.

Let me give you an example. Imagine you’re wrapping up a meeting with Erin Roberts, founder and CEO at Moogle. During the conversation, she mentioned she’s really struggling to keep up on her 1:1 meetings in her rapidly-growing team.

Through follow-up questions, you learned this bothers her because she feels like she’s losing the ability to build meaningful relationships with her team members. If you were listening empathetically and truly hearing her pain points, here’s how you might be able to respond:

“I think I get where you’re coming from but let me make sure I understood correctly: You’re feeling like your inability to consistently have 1:1 meetings with your team is causing you to lose touch with your relationships. Is that right?

“In a similar situation, I can imagine I’d feel the same. I actually read a really interesting article on how to overcome that type of CEO loneliness. If you think that might be valuable, I’d be happy to track down the link and send it to you—it offers a super-simple way to keep building those relationships in dramatically less time.”

Do you see how that might be more impactful and well-received than if you’d just said, “Yeah, that sounds hard. I read an article about that once—want me to send it your way?”

The Simplest, Most Important Relationship Habit to Adopt Today

If you only adopt one relationship habit from this entire post, make it this: 

Never leave an interaction without offering at least one item of value.

The key, of course, is to offer value that’s truly meaningful and relevant to the other person, and to offer it in such a way that it’s going to make the biggest impact. And that starts by never asking, “Hey, how can I help you?”

Want to start practicing these skills immediately? I recommend rekindling some of the relationships you’ve let fade away over the last couple months or years—these are a great “training ground” for new habits.

Not sure how to strike up a conversation with someone you haven’t spoken to in months? Download my Five Freebies eBook here for 5 ready-to-send email templates that allow you to access virtually anyone in your network at practically any time.