man reaching out

You’re determined to start the next chapter in your career, and you’ve psyched yourself up for the inevitable networking frenzy that will ensue. You’re ready for the cocktail gatherings, coffee meetings, and informational interviews. You’re armed with an elevator pitch on what you want next, and you’ve got the conversation art down to a science.

But before you can get to those in-person scenarios, you’ve got to first connect via email. And when sticky networking scenarios come into play, reconnecting gracefully can be a real chore.

Here are a few templates for tackling some of those tough circumstances.

1. The Person You’ve Reached Out to Too Often

You know that person in your network with all of the contacts, the one whose connections stretch far and wide and run deep? You do because you haven’t been shy about regularly checking in with him throughout your career. You find yourself circling back to him frequently because he’s the first person who comes to mind when you need a professional favor. Although he always seems happy to help, you’re starting to feel a little uncomfortable about approaching him again.

Instead of agonizing over it and delaying, just start writing an honest, candid email. Thank your contact for being so helpful, and acknowledge the repeat requests. It can be nice to mention something that doesn’t relate to your networking goals to remind him that you’re not only interested in his LinkedIn connections. Depending on your relationship, you might even suggest grabbing a drink and taking the conversation off email. Here’s how you might go about it:

Hi Joe,

I hope you’re having a great week. It was so much fun seeing you last week at Sarah’s party!

I wanted to thank you again for being so helpful over the last few weeks as I continue my job search. Since I last saw you, I came across a job opportunity at [Name of Company] that I’m really excited about, and I know you’ve mentioned that you’re in touch with the CTO there. I was wondering if you’d be willing to connect us via email. I’d really appreciate it.

Also, next time we’re at Mackey’s, drinks are on me! Thank you again, Joe. I’m really grateful for your help.

Talk soon,
[Your Name]

2. The Person You’ve Cancelled On

Now here is a sticky situation. Back when you were content at your company, changing jobs not even a passing thought, your former colleague, whom you were close with when you worked together, contacted you about meeting for breakfast or a beer after work. Twice, you had plans, and both times you flaked. It doesn’t matter why; the fact of the matter is that you proved yourself unreliable.

Suddenly, you find yourself ecstatic about a position at her company, and you know you have no other choice but to bite the bullet and reach out to her. She’s the best person you know who can speak to the company culture and the open position, but thinking about reaching out makes you cringe.

Once again, this is a time to remember that honesty is the best policy. Apologize sincerely for not making a better effort to meet up, but then move on. The initial email might be more about getting her opinions about her current workplace. If she’s open to sharing her advice, thoughts, and feedback about the organization, then you can move on to asking for assistance with your application. Start the first email like this:

Hi Lucy,

I hope you’re doing well. It’s been a while since we’ve been in touch, and it’s totally on me. I’m sorry that I wasn’t able to make our previous dates a couple months back. It would be really nice to catch up.

I’ve also got some interesting news: I started looking for a new job, and the [name of position] at [Name of Company] caught my eye. You seem to be pretty happy there, and I’d be interested in hearing more about your experience and general feelings on the organization and its mission. If you have the time, will you let me buy you a cup of coffee or a margarita? Thank you, Lucy. Looking forward to seeing you.

[Your Name]

3. The Former Colleague You Never Really Clicked With

Look, you can’t be best friends with all of your colleagues. When the co-worker you didn’t have much in common with announced he was leaving the company, you were far from heartbroken. You just never quite clicked. And although it was no walk in the park trying to chat with him, you didn’t dislike him. Though you have no idea what he thought of you.

But now, in researching jobs, you’ve discovered that he’s in a pretty senior role at a company you’re eyeing. Since he’s the only contact you have, you want to reach out, but you can’t figure out what to say. This is a time to really squelch the over-analysis. It’s quite possible he didn’t dislike you at all; maybe you truly just had nothing to talk about.

Instead of deconstructing ever interaction you ever had, sit down and write a professional message: Re-introduce yourself, update him briefly on the situation, and ask if he’d be willing to connect you to the hiring manager. Include a draft email for his convenience. You don’t have the relationship to support a glowing recommendation, but there is no harm in asking for the intro.

Hi Sam,

I don’t think we’ve seen each other since you left [Old Company Name], but [Name of mutual friend] tells me you love it at [New Company Name]. I’m glad you’ve found something you like so much. I’m contemplating finding a new job myself and I recently came across a position at [New Company Name] that’s really intriguing. Based on my research, it’s a different department than yours, but I was wondering if you might be willing to connect me with the hiring manager for the position. I’ve included a draft email to make it easier for you, and of course, feel free to make any edits. I’ve also attached my resume.

I really appreciate your help, Sam, and I look forward to returning the favor.

[Your Name]

Reaching out to networking contacts isn’t always straightforward; sometimes, there’s baggage. But that doesn’t mean that the situation is hopeless. Focus on being honest, direct, appreciative, and gracious. The worst thing that can happen is that the person doesn’t email you back or replies with a curt, unhelpful message. But wouldn’t you rather know you gave it a shot? Especially since the best case scenario is that you land your dream job at least in part because you faced a seemingly awkward situation.

Updated 6/19/2020