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How to Network With Former Bosses Without Being Awkward

You’re filling out your next job application when you read the daunting words: “Two references required.” While you have plenty of former supervisors whom you’ve impressed with your excellent intern skills, it’s been a few months since you last spoke, and you’re not sure how to approach them without seeming like you’re just using them for a job. Fortunately, we’ve broken the process down into three simple, effective phases with the help of our career experts, so you can be authentic and professional every step of the way! 

1. Reach out

If you’re looking for a job at that company


Tom Dezell, author of Networking for the Novice, Nervous, or Naïve Job-Seeker, suggests asking for advice rather than a favor. Everyone loves sharing good stories and talking about their interests, so focus on developing a mentor/mentee relationship rather than a purely boss/employee relationship.  

“People are going to be much more responsive when you’re asking them for advice on how to approach a situation, and they can respond within their own comfort range,” he says. “It’s a mistake at all levels to just ask for a referral or a job.”                          

Lesley Mitler, founder and CEO of Priority Candidates, Inc., a career coaching service for college students, says the best methods of communication are through a LinkedIn message or a professional networking email.

If it’s been a year or two since you worked at a company, start by reintroducing yourself with your name, the position you held during your time there and what you studied in college. If you’ve recently left and know your supervisor well, then start by asking how he or she is doing – that’s a point all our experts emphasize! Even though it might not feel like a big deal, simply showing interest in how someone is doing communicates a lot. Give a little background on what you’ve done since you left your position and why you’re interested in working for the company.

If you’re asking for a connection

If you’re looking for a job at a different company or in a different industry and you think your former boss would be able to help you, Dezell recommends making a connection between your former job and your new interests. For example, if you want to go into publishing but previously worked in online journalism, tell your old boss about what you learned from your job and why it inspired you to explore other options. You can also add a few long-term goals you have in mind just to show that you’ve done your research and know how the job will fit into your career path.

If you’re asking for a recommendation

Mitler says you should usually get a recommendation right after you leave a position, so be sure to follow this step-by-step guide to a killer recommendation letter! However, since most potential employers will want to get in touch with your references, it’s still beneficial to reconnect with your former bosses and let them know that you’re on a job hunt. Tell them what positions you’re applying for, ask if they would be willing to be a reference for you and, if they are, bring up any successful projects that you would want them to highlight.

“If you work for someone who is on LinkedIn, you should ask for a recommendation via LinkedIn,” Mitler says. LinkedIn recommendations are usually more convenient for people to write and will always be accessible to potential employers looking at your profile.

2. Arrange a meeting


Schedule a time

Lesley Mitler says it’s a good idea to schedule an office visit, coffee or lunch date with your former supervisor when you’re in town. She emphasizes face-to-face contact, which will give you a way to spend more time with someone and be more personable than you would be over the phone. If you’re not in the area, however, set up a time to talk on the phone.

If you don’t get a response, wait a few weeks (since some people might just be busy and forget to respond) and then follow up with a brief message saying that you’re still interested in getting some advice and you’d love to meet at his or her convenience.

Be sure to dress neatly, regardless of the occasion. Even though it’s not an interview, your former boss is a potential employer with a lot of connections and will be gauging your skills and aptitude the entire time. Since coffee or lunch will usually take place in a casual setting, it probably won’t be necessary to dress business professional, but make sure your outfit doesn’t include any jeans, sneakers, T-shirts or tank tops.

Ask the right questions

We’ve all had those relatives who told stories from their childhood filled with life lessons, and with your bosses, it’s not any different. Sometimes the best way to learn is by example – hearing anecdotes about real experiences. While you should do the usual research on your industry and ask technical questions, it’s also important to establish a personal connection with your former boss as well, says Stefany Fattor, director of career services at Fordham University.

Here are a few professional and personal questions to ask:

  • If you were in my position, what would you do?
  • What inspired you to enter this industry?
  • What’s your favorite/least favorite part of your job?
  • What are some companies you would suggest I apply to?
  • Do you know anyone in this specific field I’m interested in whom I could speak to?

Even though you’re talking about careers, you can also look for mutual interests that might not have anything to do with the job you want but can spark an interesting conversation and show who you are as a person. When an employer offers you a job, he or she is also investing in you as an important part of their company. He or she wants to know that you’re someone who’s genuine and trustworthy.

3. Follow up

Stay in touch


It’s easy to make the mistake of not reaching out at all when you’re afraid of bothering someone, or pestering them too much because you want to show enthusiasm. Make sure to maintain appropriate boundaries when keeping in touch.

Mitler suggests contacting someone no more than once every two months. “You can gauge their interest level in staying in touch by how often they respond,” she says.

Just as you stay in touch with friends by sending funny memes or videos you come across, you can also connect with your old boss through any relevant news articles or blog posts that you think he or she would enjoy, so take the time to forward a link once in a while! Mitler also recommends following professional Twitter accounts and retweeting any posts that you find interesting. If you’re worried about bothering someone too much, tweeting at him or her is a good alternative to a formal email.

Stay motivated

Getting a job solely through networking isn’t easy, but it’s important to keep showing interest, because that’s what will set you apart! Persistence helped Fattor land her job at Fordham Career Services, because even though she didn’t get a position the first time around, she continued asking questions and showing curiosity.

“The person who interviewed me recognized my passion for serving students and offered to help if I applied for any other positions at Fordham,” Fattor says. “Soon after, there was a need for an interim director of career services, and he remembered me.”

Fattor suggests updating your former bosses on what you’re up to throughout the rest of college. Maybe you got another internship, joined an organization or picked up a new hobby; all of these are great conversations starters that will set you apart from other interns who worked there.

“Always remember that networking is relationship building, and relationship building takes time,” she says.


We know it’s not easy putting yourself out there, especially when it might feel like you’re asking for a job or a favor. Instead, think of it as asking for an opportunity to grow and develop your career, and that’s especially easy if you’re genuinely passionate about your former internship and you’ve decided that you want to work at the company full time. But even if you’ve changed your goals and you’re looking to work somewhere else, your former bosses will understand that you’re following your passions and taking your own path. As long as you show that you’re interested in other people’s advice and respect their time, they’ll see your enthusiasm and be willing to help you invest in your success!

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