How to Reconnect the Right Way

How an intentional approach to reconnecting goes much further than "hey it's been too long.”

Author

Devin Keane
September 13, 2023

Read time: 6 minutes

Hi Proactive Professional,

A big part of what I am doing lately is re-connecting with the people that had a positive impact on my career trajectory.

However, when I (re)started my networking journey, and before I noticed the importance of intentionality in reaching out, I did a very poor job of reconnecting.

At that point, the name of the networking game was numbers. The larger my network, the more of an impact I could have. So my obvious first step was reconnecting with all the contacts I had let go “cold”.

Networking: gotta catch em all! (or so I thought)

So in playing the numbers game, I shot out an unthoughtful and vague: "Hey [Name], it's been way too long! I was reminiscing about the old [work/school] days. It would be great to catch up on how you've been since we last spoke."

I laugh when I look back at those messages I had sent.

  • "I was reminiscing about the old [work/school] days" - Ok…like what? The three weeks of all-nighters we pulled to get a pitch done or the fun we had during the closing dinner after a successful couple hours at the roulette table?

  • "It would be great to catch up on how you've been since we last spoke." - Well, that’s a lot to unload. We haven't spoken in 3 years. Would you like to hit on the engagement, the new house, the additions to the family, the last two job switches, or what I'm working on at the moment? Not even a fraction of that could be covered in a 30 minute phone catch up.

Their initial reactions were often pleasant (wow, haven't heard from Devin in years!) quickly followed by being perplexed (wait, but why is he reaching out now?). I'm sure they were all thinking the same thing: What does he need from me?

The aha! moment came after two very similar catch ups.

They both started with smiles over Zoom after not having caught up in 3 years. Then, I gave the 5-minute, speed dating version of what I've been up to. After, I asked them for their update, and finally it culminated in a few moments of awkward silence. Sometimes a rogue "how's the weather been" or "anything fun planned coming up" was thrown in, just extending the awkwardness. Then we end the call, not having accomplished anything by reconnecting.

What happened? I made it too ambiguous. Many things were hit on at a high level, but we didn't dive into a single one of them deeper. I didn't have a real purpose for the catch up, which likely left them frustrated and feeling they had wasted 20 minutes of their valuable time, only to exchange bland hellos and neither gained nor gave anything in the conversation.

I lacked intentionality. I had no reason for catching up with them or trying to initiate more frequent communication. So I came up with a different approach.

Strategy for Proactive Professionals to be more intentional in reconnecting:

1. Think About Areas of Improvement and Things to Accomplish

These areas can be urgent (advice on an upcoming interview) or less urgent (doing a better job of creating presentations), but they should always be specific. They can span skill development, breaking into new roles or industries, navigating difficult decisions, expanding networks, or seeking guidance in any particular topic.

What that looks like for me:

  • Advice on finding a technical co-founder for a new business venture

  • Navigating the landscape of incubators, accelerators, and venture capital

  • Understanding the most impactful channels I can use to scale this newsletter

What that could look like more generally:

  • Negotiating a new salary or title

  • Finding more effective approaches to presenting

  • Understanding a particular industries trends better

2. Make a List of Contacts Who Can Align With Those Areas

Be intentional about the contacts you want to reach out to. It should be easy to answer the “why” they align with your improvement area, but it should go further than just having crossed paths with the person. I like to make sure they have fallen into at least one of a few categories:

  • They had an impact in guiding me to where I am today

  • We had a close working (or academic) relationship

  • I left a positive impression on them

  • I had at least one positive shared experience with them

Start by picking just three contacts that check the boxes so far.

3. Choose the Right Method of Outreach

Method 1: Be specific and ask for advice

This works better for someone you have worked closely with and asked for advice from in the past. This can act as a way to reintroduce yourself to the person while calling out that they have expertise in an area and you would like to pick their brain on it (at their convenience.)*

*No, the message should not be that direct. See step 4 for crafting the message.

Method 2: Provide value

This is typically the approach I take with contacts I left a good impression on or had at least one positive shared experience with, although it works for any connection type. This can act as an intermediate step before Method 1, and is a way to ease into asking for advice in a genuine way. Two ways I try to do this:

  1. The mutually beneficial introduction: Offering to make an introduction to someone they should know. Maybe the connection will help them grow their business, has relevant expertise, is their next big client, or is in similar shoes but under different circumstances. The important parts here are getting buy in from both people before making an introduction and setting a clearly defined reason for why they could be mutually beneficial. Otherwise the intro'd duo may feel obligated to take a call that provides no value to either side. (thanks to Khe Hy for passing along one of his RadReads blogs on the topic here)

  2. Finding a topic or article that would be relevant and interesting to them. This is very similar to the proactive nudge approach, with slightly different messaging.

4. Craft the Right Message

Since this is the first message you will have sent their way in quite some time, it's important to approach it delicately. Here are the things I keep in mind:

  • Acknowledge the absence of contact: Mention that it's been a while since you last spoke and that you are working on doing a better job of keeping in touch with people that have positively impacted your career.

  • Reference tangible memories: Don't oversell (you're constantly on my mind!) or undersell (I don’t expect you to remember me). Instead, reference a shared memory from the relationship. Bonus points if it's related to the advice you may be asking for!

  • Compliment them: This could be on a relevant area of expertise if asking for advice, or on an area of interest if providing value through an article or mutually beneficial intro.

  • Show you have kept up from a distance: Mention you've been keeping up with their journey (i.e. social media) and congratulate them on any big accomplishments.

  • Make it specific: If your purpose is to get advice, ask to set up a call at their convenience. If it's to add value, send them the article and why it made you think of them.

5. Follow Up Promptly

Don't wait too long to respond if they get back to you. Otherwise, the opportunity to reconnect could be lost.

BONUS: Template for Reconnection Outreach
Available to Subscribers With at Least 1 Referral

Reconnecting without a purpose is a waste of time for all involved. Once you both get past the initial shock and awe of seeing each other after a long time has passed, you'll quickly notice there is little or nothing else to talk about. That very well could be the nail in the coffin for that connection, ghosting you on any future reconnection attempts.

Instead, take the intentional reconnection approach. There is so much untapped value in these former connections, it's just a matter of pointing the relationships in the right direction. These are people you've already worked closely with and laid the ground-work for mutually beneficial connections.

In other words, they know you already—if that’s a good thing, take advantage of it.

What I’m committing to this week for building relationships (time commitment ~3.5 hours):

  • 👋 Reaching out to three former contacts I haven’t spoken to in 2+ years (~30 minutes)

  • 🤝 Attending an entrepreneurs round table in NYC (~45 minutes)

  • 🥡 Going on Chinese food tour in Flushing, Queens with a former colleague (~2 hours)

  • 🤔 Reflecting on my week this Friday: what are the reasons certain important connections went cold in the first place? (~15 minutes)

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

Best of luck building,

Devin