Connect with one old colleague or boss

You want to start a conversation with an old colleague or manager, but you haven’t talked in years. How do you parachute into a long-lost acquaintance’s inbox?

It’s a delicate mission. To figure out the best approach, we talked to leadership coaches with experience helping midlevel employees and executives manage priorities and stress, and be more authentic.

Start by determining your “why," says Aimee Cohen, who’s based in Denver and runs ON Point Next Level Leadership. Ask yourself what you’re seeking. A new job in your field? Advice and leads on how to pivot to a different industry? Or a desire to develop new skills, find a mentor or generate more client referrals? The person you reach out to—and how—will depend on your answers.

1. Break the ice

Don’t dance around the fact that it’s been a hot minute since you spoke. You want an opening line that isn’t phony, says Michele Woodward, a Washington, D.C.-area executive coach. You can try an email subject line like “Blast from the past," or start your note with “You popped into my head this morning, which only means it’s time to catch up."

Woodward tries to share something more personal like, “Was just in that Chinese place where we used to get lunch and it made me think of you," or “Saw that your college is ranked in the top 10 this week—are you going to any games?"

2. Keep it real

Acknowledge that you don’t fully know what your onetime colleague has been up to. Sure, you may hdave scanned their LinkedIn profile before reaching out but take time to hear it directly from them. You can say something like, “I know so much has changed in the world since we last chatted. Are you still focused on environmental law?"

3. Be personal

No need to gush, say coaches, but detail what you miss about the person. “I still think about how valuable your perspective was in meetings," or “Remember our brainstorming sessions?" Then drop one or two shared experiences that made an impact: “I still appreciate how you handled that client at Company XYZ."

4. Be of service

This doesn’t need to be one-sided. Make clear you want to be helpful to them, too. For example: “I’d love to hear more about what you’re on the hunt for these days."

Keep your offer specific to their interests and expertise. News articles, blog posts, even job postings are fair game to send along, as long as you caveat that this person’s life may have changed since you last spoke. You want to show that whatever time has gone by, your old contact—and the person’s specific skills and hobbies—are top of mind for you.

5. Manage your expectations

Hopefully, you’ll hear back. The worst that can happen is a nonresponse. You can try following up once more after a week or two—people are busy, after all. If you’re still hearing crickets after that second note, move on.

When you get a response, there’s an art to keeping in touch, say coaches. Here’s a rough guide:

Close contact (former colleague, now friend): MonthlyMidlevel contact (your boss for a year): QuarterlyExtended contact (guy you joked with at the water cooler): Twice yearlyAcquaintance (one-time vendor): Annually, around the holidays

You can do this. Virtually everyone has at some point lost contact with someone or dropped the ball on following up, so your old contact will likely understand. Now, go reach out.

Write to Ray A. Smith at Ray.Smith@wsj.com