Reader situation
You’ve lost touch with a former colleague you respected. Reaching out after a long gap can feel awkward, especially if you need something. Many people put off the message until it feels too late to send.
Central idea
Reconnecting works best when you acknowledge the relationship and explain why you are reaching out now. A shared experience and a specific, low-pressure invitation make it easy for the other person to respond.
Worked example
Fictional example
The people and details are invented to illustrate an approach.
Fictional context
Grace and Omar worked on the same product team for three years. Grace left five years ago, and they haven’t spoken since, apart from occasional congratulations on career news. Grace is now considering a move into healthcare technology. Omar has worked in that sector for the past two years.
Shared reference
Grace thinks about what they shared. They worked together on a difficult product launch that ran late, and they often stayed after meetings to talk through problems. Omar once helped her prepare for a hard conversation with a senior stakeholder. That shared history gives her a natural way to open. She chooses the stakeholder meeting because it is specific and because it acknowledges something Omar did for her, rather than something she wants from him now.
Specific reason to reconnect
Grace’s reason is clear: she wants to understand what product work is like in healthcare technology before deciding whether to pursue it. She doesn’t want a job referral, and she decides to say so. She also considers whether Omar would want to hear from her. They parted on good terms and he has congratulated her on news over the years, so she judges that a message would be welcome.
Low-pressure message
Hi Omar, it’s been a long time. I still think about the launch we worked on and how much you helped me through that stakeholder meeting. I’ve seen that you’ve been in healthcare tech for a couple of years. I’m exploring whether to move in that direction and would love to hear what the work is really like. I’m not asking for a referral, just your perspective. Would you be open to a 20-minute call in the next few weeks? Completely understand if things are busy.
The message acknowledges the gap, names a specific shared experience, explains why Grace is writing now, says what she isn’t asking for and makes it easy to decline.
Possible replies and next steps
- Omar agrees. Grace suggests two or three times, prepares a few focused questions and sends a thank-you afterwards, along with an update if she makes a decision.
- Omar is busy but interested. Grace thanks him and asks if she can get in touch again in a couple of months.
- Omar replies warmly but suggests someone else. Grace thanks him, asks whether he’d be comfortable introducing her and follows the same respectful approach with the new contact.
- Omar doesn’t reply. Grace waits two weeks and sends one short note. If there’s still no reply, she lets it go and doesn’t take it personally.
Boundaries
- Don’t open with flattery or pretend the gap didn’t happen.
- Be honest about why you are writing. People can tell when a “catch-up” is really a request.
- If the relationship ended badly, consider whether reconnecting is welcome before you send anything.
Reflection questions
- Who have you lost touch with that you would genuinely like to hear from?
- What shared experience could you mention?
- What is your real reason for reconnecting now, and how could you say it plainly?
One practical application
Write a reconnection message to one former colleague using the five parts above, and send it within the week.
