Here’s how to reach out to old colleagues…without feeling awkward

Let’s be honest: reaching out to someone you haven’t spoken to in a year (or more) can feel… weird.

Your brain starts running through all the “what ifs.”

• What if they don’t remember me?
• What if they think I’m only contacting them because I want something?
• What if it’s awkward?

This came up on a recent support call with a client who had applied for a dream role. She knew someone at the company but hadn’t spoken to him in over a year. Should she send that message or not?

She did. And the response was warmer than she expected.

Here’s why it worked, and how you can do the same.

Lead with Authenticity

The first mistake people make when reconnecting is treating the other person like a transaction.

Don’t just pop up with:
“Hey, can you put me forward for this job?”

That’s a fast track to being ignored.

Instead, start from a genuine place. Remind them how you know each other. Share why you thought of them. Make your message personal and gracious.

For my client, it was as simple as:

“Hi [Name], long time no speak! We met when I was exploring roles at [X company], and I really enjoyed our chat. I’ve just applied for a role at Red Bull and thought of you immediately — would love to catch up.”

Notice the difference? Same purpose, but it lands so much better.

Tailor Your Ask to the Relationship

Not all contacts are created equal.

There are really two types of people in your network:

1. Close contacts

These are people you’ve worked with or have a strong relationship with. You can be more direct. 

For example:

“I’ve just applied for [role]. Would you be comfortable connecting me with the hiring manager?”

2. Loose contacts

These are people you don’t know as well. With them, focus on asking for advice — not a favour. 

Try something like:

“I’ve applied for a role at [Company]. From your experience there, is there anything you’d recommend I highlight in my application or interview?”

Both approaches open the door. But one feels natural to a close contact, while the other shows respect for someone you don’t know as well.

In the Meeting, Play the Long Game

If the outreach leads to a meeting, don’t jump straight into talking about the job.

Front-foot the conversation with genuine curiosity:

• What have they been working on lately
• How are they finding things at the company?
• What are they excited about right now?

Only later, once you’ve reconnected, should you pivot:

“By the way, I’ve applied for [role]. Do you have any advice on what Red Bull looks for when hiring?”

That way, they know you’re not only there to “get something” — you’re building a relationship. And those relationships are often what create opportunities far beyond the job in front of you.

The Bigger Lesson

Networking isn’t about perfectly-timed coffees or smooth introductions.

It’s about showing up authentically, keeping the relationship human, and not letting fear of “awkwardness” stop you from reaching out.

My client could easily have talked herself out of sending that email. Instead, she did it. And the door swung wide open.

And here’s the kicker: even if this Red Bull role doesn’t come through, that contact is now back in her circle. Which means new doors could open down the line.

If you’ve been holding back from reaching out to an old contact because you’re worried it’s awkward — take this as your sign. Send the message. You’ll be surprised how often people want to help.