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3 Strategies to Avoid Awkward Catch-Ups

Keith Ferrazzi and I emphasize the importance of not just making connections, but nurturing them into genuine relationships.

Author

Devin Keane
September 06, 2023

Read time: 3 minutes

Hi Proactive Professional,

What's the fuel that keeps connections…well…connected?

Connections thrive on more than just occasional catch-ups. Rather, strong connections rely on continuous exchange of value. Whether it's sharing valuable information, doing favors, or offering advice, these exchanges keep the relationship warm and beneficial to both parties.

In most lasting connections, this value exchange becomes mutual over time. However, it often starts with one person reaching out and aiming to establish their worth to a potential connection.

Today, we'll refer back to Never Eat Alone and my personal experience to discuss:

  • Alternative outreach techniques beyond the usual coffee chat

  • The importance of understanding the motivations of your connections

  • How to add value even when your direct skillset doesn't seem relevant

The Paradox of Frequent Interactions

As I've begun to build a more meaningful network, I've noticed an interesting trend:

The more frequent catch-ups I have with a connection, the harder it becomes to sustain meaningful conversation over that 30-minute calendar block.

Initially, here's what would happen:

  • I identify people in my "high-impact" network: the ones most closely related to my goals

  • I set a regular check-in cadence (say, monthly)

  • The first interaction is rich with updates, advice, and discussions around future aspirations

  • Subsequent check-ins, however, often feel repetitive, with both of us grasping for topics to talk about

So I started thinking about how to push past this “connection plateau” I was experiencing. In other words, how to make these catch-ups less awkward.

Now, I space out in-depth check-ins and send "proactive nudges" between those check-ins.

A proactive nudge is a subtle way to reach out without expecting a response. It's not about selling or requesting anything. Instead, it's about sharing relevant information, like an article, podcast, or book recommendation, that’s fitting within the context of your relationship.

(for more on my proactive nudge method, see the bonus takeaway)

Let’s dive deeper into this approach and a few others to enrich your connections.

3 strategies for Proactive Professionals to avoid awkward catch-ups:

1. Figure Out Your Connection’s Motivation

  • Takeaway: "Try to find out what motivations drive that person. It often comes down to one of three things: making money, finding love, or changing the world."

  • Tip: Step one is understanding their motivators. Are they mission oriented, money oriented or driven by some other underlying passion? Figuring out what makes them tick puts you in the best possible position to add value—be it from your own skillset or through relevant introductions to others.

2. Stay Consistently Engaged

  • Takeaway: "If 80% of success is, as Woody Allen once said, just showing up, then 80 percent of building and maintaining relationships is just staying in touch."

  • Tip: Constancy matters a lot when it comes to outreach. Staying in touch is not defined in one way. It can take on many forms—proactive nudges, coffee chat, dinner, drinks, sporting events, etc. Each interaction should involve some value exchange. It can be as small as a thought provoking article or as big as snagging some tickets to Bruce Springsteen for a superfan.

3. Make Meaningful Introductions

  • Takeaway: "Successfully connecting with others is never about simply getting what you want. It's about getting what you want and making sure the people who are important to you get what they want first. Often, that means fixing up people who would otherwise never have an opportunity to meet."

  • Tip: We aren't infinite wells of information and knowledge and as a result, we sometimes can't directly offer value to certain connections. That's when we have the opportunity to dig into our network and find someone that can. Putting connections in touch with people they otherwise would have never met is one of the easiest ways you can contribute to their success.

BONUS Cheat Sheet: The Proactive Nudge Method
Available to Subscribers With at Least 1 Referral

Let's face it, without consistent nurturing, even the most promising connections can wane. By being thoughtful in your interactions and the value you offer, you not only strengthen your current relationships but also position yourself to reap benefits in the future.

*future me*

What I’m committing to this week for building relationships (time commitment ~2.5 hours)

  • 🌆 Attending Andrew Yeung's last Tech Rooftop Mixer of the season (~1 hour)

  • đź“ž Catching up with a connection considering making the jump into entrepreneurship (~30 minutes)

  • 🗣️ Interviewing the founder of a DEI Executive Placement firm to learn more about the art of connecting others (~45 minutes)

  • 🤔 Reflecting on my week this Friday: Am I focused on how to make myself successful or making the people around me successful when connecting? The latter is what pays dividends (~15 minutes)

What are you committing to this week? Reply to this email!

Best of luck building,

Devin