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  • Writer's pictureHarshal

12 Learnings And Tips From Reconnecting With Social And Work Connections

I Messaged 920 People Last Year. Outcomes, How, Why, And Lessons Learnt.

I messaged 920 personal and work connections last year.

Thanks to moving across cities, across jobs, and staying 'connected' via social media, you know more people than your previous generation. But, sometimes staying in touch with your connections can feel like navigating a complex maze.

Here's what I learned about reconnecting with people I met, whether I met them a day ago or a decade ago.

In this post, I deep dive into:

  • Relationships,

  • Evolution of communications, 

  • Power of simplicity, and 

  • Use of ChatGPT (LLMs).

I spent 3 hours and 45 minutes writing this post.

What’s the correct term? Ex-colleagues, old classmates, acquaintances, friends, network, contacts, connections, relationships, people I know, folks, or something else? Julie Brown, in "This Sh*t Works," suggests work friends are friends too. So, she advises not to separate work connections from social connections. I’ve used a mix of terminology in this post.

Collage of many conversations.
Collage of many conversations.

Related posts:

Motivation: Why Did I Message 920 People?

1 - Good companions: I decided to keep in touch with people from work, school, or hobbies because I had enjoyed their company in the past. Ideally, if I could stay in touch with them with zero effort, I would do it.

2 - Overcome reluctance: But in reality, it takes effort. So, I decided to train my relationship-muscle to make staying in touch easier. Over the months, I reduced the barrier of fear, apprehension, and effort to reconnect with someone.

3 - Books on relationships: I read books about the power of connections and the opportunities they bring. I learned about the Dunbar number, The Good Life, This Shit Works, Four Thousand Weeks, and How To Host A Cocktail Party. I realized nurturing my relationships was important for my happiness and success. I was ready to put in the effort to nurture relationships.

4 - Consulting clients: I spoke to over 40 consultants. I learned most of them get clients from their connections. Even though I didn’t know how to get clients from connections, I knew I could strengthen my relationships. So, I did the latter and now I am figuring out how to find clients from connections. More findings from my chats with experts here.

Trend of contacting over 100 people every month.
Trend of contacting over 100 people every month.

From my data, I noticed:

  • Meetups: I had a peak in March 2023 because I attended several meetups where I made new connections.

  • Party hosting: My peak in May 2023 was my outreach for the cocktail party I hosted in June. I messaged 182 contacts in a day. I'll share more about hosting 100s of friends at my home in another post.

  • Family first: In September 2023, I messaged less due to a family injury. I reduced work and focused on family.

  • Holiday season: Like many, I focused on family. I cut back on messaging outside my family in December.

12 Learnings And Reflections From Connecting

Initial Contact

  • Even when I connected person A to B without asking B beforehand, every B still responded and helped.

  • Social media platforms like Facebook, LinkedIn, Twitter, and Instagram have helped us maintain a broader circle of relationships. More number of weak ties. This is because they allow us to see what the other person has been up to. This gives us common ground to connect right from the first message. If I didn’t have social media, I would reach out with my stale 10-year-old memory about them and start with very basic questions to understand where they were now.

  • My biggest challenge was overcoming my reluctance to spend time messaging people, versus work, writing, and other “deep work” activities. Each message leads to more messages, so I felt my time spiral away from deep work. I tried to limit all my communications to one hour at the end of my day. My hope was to do focus work the rest of the time. Yet, I usually message people throughout the day.


  • People remembered me, even if we last studied together in 6th grade and were now 10,000 miles apart.

  • People were happy to hear from me, a past connection.

  • People were happy to be wished on their birthdays, even if I only found out about their life events through social media platforms.

  • I forgot situations where I didn’t get a reply from someone I messaged. So, I didn’t feel bad about it. I moved on. But, I felt sad when I didn’t hear back from some, like a best friend from a previous job.


  • When chatting after such a long time, it was hard to reconnect and find topics we were both interested in. Yet, since I knew so little, everything on their LinkedIn, Facebook, or Instagram was new to me, giving us a lot to talk about.

  • I gave people the benefit of the doubt. If they forgot our previous conversations or context, I jogged their memory.

  • It was clear when some people used ChatGPT for their responses. I appreciated personalized responses over such canned responses. In a way, seeing poorly written AI-generated responses motivated me to chat in my genuine voice.

Communication and Relationship Dynamics

  • Maintaining a weak tie over social media through text messages was easier than reconnecting and strengthening the tie through coffee or virtual coffee. Sometimes, virtual meetings made us realize we had grown apart. It was obvious at the start of a call that we’d grown apart. Yet, it felt worse to acknowledge it.

  • People change over time. People who entered a meeting assuming they knew everything about the other person were often surprised. Those who approached the meeting with curiosity, eager to learn how the other person had changed, made the meeting better for both. For instance, an undergraduate friend treated me as if I still knew nothing more than the undergrad courses.

Ripple Effects: Impact From Reaching Out

Some impacts of reaching out and keeping up with both new and old relationships in 2023 included:

  • Making new close friends.

  • Enjoying reconnections with old friends.

  • Getting referrals for consulting jobs.

  • Feeling at home and surrounded by love, even in a new continent.

  • Getting a referral that landed a new job for my spouse.

  • Overcoming reluctance to talk to new people at parties.

Dan Wyks in his newsletter “Better Ways”, shared the impact he experienced from doing something similar:

  • The strength of weak ties.

  • People care. Even people you barely know.

  • I have more friends than I previously believed.

One of my goals in 2024 is to prioritize time for my important relationships. For example, I might follow the ‘My Social Universe” exercise from The Good Life to categorize my friendships on an 'energize - deplete' axis to better manage social interactions.

Sample exercise visualization as a bubble chart with the number of relationships at each point.
Sample exercise visualization as a bubble chart with the number of relationships at each point.

12 Tips To Strengthen Connections

Initial Contact

  • Your old connections from work or school (former colleagues and classmates) remember you. You won't hear "Who are you?" Don't be shy to send them a message.

  • If you know whom you want to message but are hesitant - realize that thinking about reaching out to someone is the first step. You’ve already taken the first step. Don't hesitate; just do it.

  • The book "How to be a Power Connector" teaches us to ask Person B if it's okay before connecting them with Person A. Don't surprise Person B by group emailing or texting them with Person A to introduce them.

  • If I could get over my initial reluctance to message someone, I would be more open to messaging more contacts the same day. David Fields taught this, and I drew the below graph for it. More thoughts on relationship-building strategies for consultants here. I sometimes gamify it by creating a to-do list on paper. I checkbox each name as I message them. Checking boxes helps me visualize my progress and so motivates me.

Difficulty of making calls is the hardest when you are getting started.
Difficulty of making calls is the hardest when you are getting started.


  • Give people the benefit of the doubt. For example, if someone doesn’t reply to your message, send a polite follow-up. Assume they got busy. They are not ignoring you out of malice or ego. If someone is late to a call, assume they had something unavoidable come up, not that they're playing power games.

  • A person might miss your message to them. If they are a high-stakes contact, follow up twice over the next two weeks. Otherwise, do only one follow-up. Set a reminder to follow up in a week. If there's no response, assume they're busy. Try again after 3 or 6 months. Or move on. Moving on helps you forget failed attempts and focus on the successes.

  • Don't copy and paste responses from ChatGPT directly. Use tools like ChatGPT to edit or draft your messages but be aware of the tone difference. ChatGPT might use "bolster" instead of "improve" or "ecstatic" instead of "happy". Make sure the words match your style, as I've mentioned in my "Thank You Notes" post and "Make ChatGPT Write in Your Tone and Style" post.


  • Check the life events of the person on LinkedIn, Facebook, Instagram, or any other social media you both use.

  • Julie Brown in her book "This Sh*t Works" advises giving people the benefit of the doubt that they might have forgotten you. Remind them of your past context and conversations to jog their memory.

  • If you notice someone's birthday or anniversary on social media, message them on the platform they use most. If they haven't been active on Facebook but it's their birthday, message them on LinkedIn or WhatsApp instead.

  • Personalize your birthday or anniversary messages by mentioning their recent activities. This helps you reconnect better.

Communication and Relationship Dynamics

  • Approach your conversations with curiosity and an open mind. Here's an opposite example: An undergrad friend treated me like I hadn't learned anything new since my undergrad days, 15 years ago.

Example Of Using ChatGPT To Write Messages

I’ve used John or Jane as a placeholder and removed any personal identifiers from these examples.

Reconnect with Contact

  • I want to reconnect with Jane. I looked up her LinkedIn updates and wrote a draft, then realized I should also use my notes from my previous chat with her. Here are the notes and my draft. Review the draft and suggest improvements.

  • Review my CRM notes and think of what to use to reconnect with John.

  • Review my earlier email to write a connection email between these 2 ppl.

  • Help me write to Jane. I want to ask whether I can introduce her to John. I'll paste 1. draft msg 2. earlier convos for context.

Write a Follow-up Message

  • Review the messages so far and my latest draft message. What makes for a good polite follow-up message? I'm Harshal. I got introduced to John. I'm following up with John. He did not email me.

Analyze Conversation Thread

  • Harshal (me) and John have an email thread. Parse it and tell me insights about John. Only John. Ignore Harshal.

Prepare for Conversation

  • Tell me some points to bring up in my convo with Jane based on past notes.

  • Review my notes on John. Suggest questions and anecdotes I should bring up to show him I remember our previous chat and that I value him.

  • Extract personal anecdotes from these notes to ask Jane about them when I talk to her today.

  • I'm talking to John. Give me some ideas for things to bring up in convo to build a strong bond relationship with him, based on my notes from earlier conversations.

Thank After Conversation

  • Here are my raw notes from talking to John. Give me suggestions on what to write in a 100-word thank you note to him.

  • Review my notes with Jane. Especially the latest one. Tell me 50 words to write to her to thank her for her time to chat (plus imply I paid attention, I recollect about her, I care about her future stuff)

General Help

  • Help me reply to a friend. his message below.

Process: How Did I Message 920 People?

I created a process to keep in touch.

  • My process included reminders for birthdays and anniversaries.

  • I also checked people's LinkedIn, Facebook, or Instagram before messaging them.

  • Over time, I became less hesitant to reach out. For example, when someone posted something on social media, I messaged them about their post. Before, I might have just liked the post and moved on. Now, I engage directly with the person, not just their content.

  • I made a note every time I messaged someone. My goal was to remind me to follow up or to reconnect after a long time. I could analyze my communication statistics because I had noted my actions.

Aggregate statistics of the number of times I message a connection.
Aggregate statistics of the number of times I message a connection.

Your Turn For Personal Reconnections

What have you seen work well to stay in touch with your friends?

Whom do you want to reconnect with? What makes you hesitate?



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