10 Lifestyle Hacks for Reconnecting with Work Colleagues After a Long Gap and Why They Work

Credit: Style My Soul, www.stylemysoul.com | Work Colleague Reconnections

Rebuilding professional relationships after time apart can feel awkward, but it doesn’t have to be complicated. Below are ten practical strategies that make reconnecting natural and meaningful, backed by insights from workplace communication experts. These approaches work because they prioritize authenticity over forced networking, making it easier to restore genuine connections with former colleagues.

Volunteer Side by Side
I run a multi-location aesthetic medical practice, and I’ve reconnected with dozens of former research colleagues from my Johns Hopkins days who I hadn’t spoken to in years. My hack is dead simple: I volunteer alongside them at organizations we both care about. When I wanted to reconnect with three former lab colleagues after nearly a decade, I didn’t send LinkedIn messages. I invited them to volunteer with me at Baltimore Animal Rescue, where I was already active. We spent four hours walking dogs and cleaning kennels together — by the end, we’d naturally caught up on life while doing something meaningful, and two of them later became referring physicians for my company.
This works because you’re eliminating the awkwardness of “we should grab coffee sometime” that never happens. You’re committing to a specific time and place, doing physical work side-by-side, and the shared mission gives you natural conversation breaks. I’ve used this same approach with the Better Business Bureau and Baltimore Child Abuse Center — about 60% of people I invite actually show up, compared to maybe 10% who’d commit to a vague coffee date.
- Scott Melamed, President & CEO, ProMD Health

Reference a Specific Moment
What’s helped me most is reaching out with a concrete memory instead of the usual “hope you’re well.” When I get back in touch with someone I haven’t spoken to in a while — usually from an old deal or a project that had some twists — I’ll bring up a moment we both remember. Maybe it was a fire drill we somehow pulled off or a client issue that turned into a running joke. I’ll say something like, “Every time someone mentions that client, I think about how we untangled that document mess in Gibraltar. I’d love to catch up — how are things on your end these days?”
For me, it works because it doesn’t pressure them to respond with anything big. It just lets them know I genuinely remember the work we did together, and there’s a bit of warmth baked into that. In international business development, people jump between roles and regions all the time, so those shared moments end up being the glue. Reaching out with a little context rather than a vague greeting has reopened more partnerships than I expected, and it’s kept a few important connections from fading away.
- Phil Cartwright, Head of Business Development, Octopus International Business Services Ltd

Suggest a Walk Together
A surprisingly effective lifestyle tweak I’ve found is to suggest a quick walk with a former coworker, rather than a formal meeting. Walking together eases the pressure, allowing conversation to unfold more easily, and sidesteps the potentially awkward, “So, what’s new?” that can arise when you’re face-to-face after a long absence. There’s no set agenda, no power dynamics at play — just movement and shared space. It’s effective because it recreates the easy rapport you once had at work: conversations flow naturally, silences are comfortable, and trust is rebuilt more quickly. Frequently, those twenty minutes prove to be more valuable than an hour spent over coffee. - Trond Nyland, CEO & Owner, Penro.co.uk AS

Start a Joint Project
Having been absent for some time, I encountered colleagues for the first time by initiating a project/discussion with a common objective. This method is preferable to starting with small talk for the very reason that it centers the interaction, refocuses everyone’s attention on the value of working together, and fosters a feeling of advancement as a unit. It diminishes discomfort, reestablishes interpersonal relationships, and shifts the experience of working together from coercion to synergy. Kicking things off with work contributes to a more pleasant first encounter, strengthening the relationship in the process.
- Ali Zane, CEO, IMAX Credit Repair Identity Theft Lawyer

Engage on LinkedIn First
If I haven’t talked to someone in a while, I’ll comment on their LinkedIn post before I send a message. For busy people, it reminds them who you are and makes the follow-up feel less cold. It’s a small thing, but it really does get the conversation going more smoothly and makes working together later much easier. - Brandon Brown, CEO, Search Party

Send a Practical Gift
I keep reconnections light and practical. After a long gap, words alone can feel forced, so I let an object start the conversation. I’ll send something they can actually use day to day, then add a short note. Nothing polished. No long update. Just a quick line that shows I thought about them. This came from reconnecting with a colleague who relocated and disappeared into a new routine. We hadn’t spoken in years. Instead of suggesting a call, I sent a work-friendly backpack that matched how they commute now. I added a note saying it looked like something that could survive long days and crowded trains. A few days later, they messaged saying it instantly replaced their old bag and made their mornings easier.
That approach works because it removes pressure. There’s no demand on their time and no awkward rewind of why the gap happened. The gift creates a shared moment in the present. Every time they use it, there’s a quiet reminder of the connection, not an obligation to respond right away. Once that door opens, conversation flows naturally. Catching up doesn’t feel scheduled or transactional. It feels familiar. Work relationships don’t usually break. They just go dormant. A thoughtful, useful item brings them back into motion and makes the next interaction feel earned rather than forced.
- Sahir Rajan, Managing Director, WrappUp

Recall a Shared Memory
For me, reconnecting after a long gap invariably begins with an exchange of greetings and then a little trip down memory lane to WHAT ORIGINALLY BONDED US TOGETHER. I often cite a shared experience that just the two of us recall, such as a difficult client, an impossible deadline or a high-maintenance manager. The idea of bringing them up sounds familiar to both of us, and it reminds us of times we have been under pressure before. It’s effective because it doesn’t lead to small talk, yet immediately puts the conversation on a shared plane. People are more likely to open up when they feel understood and the exchange feels ORGANIC rather than transactional or forced.
For example, I recently called a former colleague by saying casually, “I was talking to a client who wouldn’t make up his mind till most Fridays were ending.” Upon hearing that single mention, an instantaneous memory flooded back. We went from laughing to having a serious discussion about how we would each handle similar situations now and perhaps catching up more often.
- Jimi Gibson, VP of Brand Communication, Thrive Internet Marketing Agency

Schedule a Coffee Chat
Getting back in touch with old coworkers often works best when you use something that both of you know and feel good about. A simple “coffee catch-up” could be the way to go. You can set up a chat for 15 to 30 minutes. You can meet in person at a cafe nearby, or you can talk online through a video call. This gives both of you some set time to talk and share what is new. You don’t have to feel like it’s a serious meeting.
Coffee breaks are part of work life and can feel easy. When you set things up like this, it shows that you want to have a loose and easy talk, not some work-only chat or a meeting that brings pressure. It helps both of you feel at ease right away.
During the chat, focus on some easy questions — ask about projects they have worked on, new skills they might have learned, or any hobbies outside of work that match up with yours. A talk like this can help both of you feel connected again, build trust, and lead to working together in the future. Sending a short message or an article after you talk can help keep the connection strong and show that you value their time. This helps turn a long break into a good work relationship again.
- Richard Gibson, Founder & Performance Coach, Primary Self

Lead With Genuine Appreciation
Before reaching out to colleagues I haven’t talked to in a while, I take a moment to remember what I enjoyed about working with them in the first place. Maybe it was their problem-solving approach, or how they made stressful projects feel manageable, or just that we had good conversations.
When I reach out with that mindset, the conversation feels genuine instead of awkward. Instead of overthinking the gap or feeling like I need to explain why it’s been so long, I can just pick up where we left off and talk about what we’re both working on now. It works because people can tell when you’re reaching out because you actually value the connection versus when you’re just checking a box or need something from them. Starting from a place of genuine appreciation makes the whole thing feel natural instead of forced. - Nirmal Gyanwali, Website Designer, Nirmal Web Studio

Meet Face to Face
I still find myself drawn to the old-fashioned way: meeting up and having a good old chat face to face. There’s just something about being in the same room at the same time that cuts right through all that distance and time. What I really like about having a chat in the flesh is its ability to bring back some humanness to the relationship. You get a chance to remember just how that other person thinks on their feet, how they react to things, and how they actually listen to you. Jokes land a lot differently, and those pauses in conversation just feel right again. You pick up on all sorts of little things that never ever make it through in a message or a call. - Harry Morton, Founder, Lower Street