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How To Reconnect With an Old Colleague/Boss: 12 Tips

Apr 1, 2022

To help you reconnect with a previous colleague or boss, we asked CEOs and experienced business leaders this question for their best insights. From staying professional to personalizing your message, there are several tips that may help you reach out to a former colleague or boss and revive that professional relationship.

Here are 12 tips for reconnecting with a previous colleague or boss while networking:

  • Stay Professional
  • Bring Back Good Memories
  • Be Positively Assertive When Reaching Out
  • Offer Them a LinkedIn Recommendation
  • Stay in Touch
  • Be Genuine and Not Overbearing
  • Keep Assumptions Aside to Avoid Disappointments
  • Thank Them for Something They Taught You
  • Create An Interesting Subject Line
  • Send An Interesting Article
  • Be Tactful
  • Personalize Your Message

Stay Professional

If it has been a long time since contacting a former colleague or boss, you should be as professional as possible when reaching out and reconnecting. Even though you no longer work together, your impression still matters, so it never hurts to keep a professional tone of email or private message on Linkedin, for example. These old professional contacts serve as valuable resources as references or sources of advice, so be as polite and professional as possible.

Brandon Brown, Grin

Bring Back Good Memories

Starting a conversation is the most awkward thing in reconnecting with a former colleague. So let me share one helpful tip: remind them of something you experienced together. It’s the perfect icebreaker because you both will feel better when you remember your good times together. Also, a sentimental mindset increases the possibility of keeping the conversation going.

Bartek Boniecki, passport-photo online

Be Positively Assertive When Reaching Out

Reconnecting with an old colleague or boss can be awkward, yet, do not make it more so by making assumptions when reaching out to them, instead be positively assertive. There are many factors that play into one’s thoughts when getting a connection request from someone that you lost contact with, including the time lapse, status of the previous relationship, and where they are personally and professionally.

Beginning your email with “I hope you remember” or “you may not remember me” not only infers negative assumptions about your relationship, but can be insulting. By being positively assertive by making no memory references, and simply identifying yourself at the end, you are both signifying that they are still prominent in your mind, while not unintentionally implying ideas that can be misread, beginning the process off on the wrong foot.

Adelle Archer, Eterneva

Offer Them a LinkedIn Recommendation

If you’re aiming to reconnect with a former colleague or manager, the nature of how you can reconnect with them turns largely on how you left your previous company. If you left under less than desirable circumstances, reconnecting may be harder and take more work. But, as in most cases, if you left under amiable conditions and maintained strong relationships when you left, it won’t be as difficult. But regardless of the circumstances, one suggestion to make reconnecting easier is to offer your former colleague or boss a recommendation on LinkedIn. Write a short paragraph about your experience working with them on LinkedIn, endorsing their skills and being sure to include how they excelled in their role. No matter how you left things, good or bad, this is sure to warm things up for a recommendation. Everyone likes having nice things said about them, even the most humble of us.

John Ross, Test Prep Insight

Stay in Touch

It is always a good idea to keep in touch with past colleagues or employers; you never know who might be an important person in your life down the road. Find a way to maintain a relationship with them, and then when you reach out to reconnect, it will feel natural. Email is always a professional yet casual way to reach out. Check-in and ask how they are doing, what projects they have been working on, and ask them if they are available for a chat over the phone or coffee. If you maintain positive relationships, it will make reconnecting so much easier.

Sumeer Kaur, Lashkaraa

Be Genuine and Not Overbearing

Be genuine. Use professional social media, such as LinkedIn, to find previous colleagues, employers, and classmates. Look over their latest accomplishments or recent post and send them a message addressing one of these and briefly reminding them who you are. Leave the door open for future interaction.

Liz Hogan, Find My Profession

Keep Assumptions Aside to Avoid Disappointments

It may have been years or even decades since you spoke to one another, and the people you are trying to reconnect with may have very different lives, moving on to other jobs or even other countries. So one way to begin reconnecting on the right note is without expectations and assumptions. For starters, do not assume they will remember, do not expect an enthusiastic or even warm welcome, and do not expect them to set aside time for you. And certainly do not assume that they will accord you the importance you think you deserve. Begin with zero expectations and take it upon yourself to rebuild the severed relationship.

Eva Taylor, WP Buffs

Thank Them for Something They Taught You

When reconnecting with a previous colleague, thank them for something they taught you while you worked together. It might be related to your industry, dealing with people, or a computer shortcut they showed you. But when you appreciate someone for something specific, it jumpstarts the relationship on a personal and authentic level. A simple, “I remember you taught me about such and such, thanks for helping me learn that,” will go a long way as you reconnect.

Logan Mallory, Motivosity

Create An Interesting Subject Line

Be sure to create an interesting subject line. It could consist of your name and where you met the colleague, for example. People are receiving hundreds of emails per day, so it’s best to get right to the introduction. If you’re networking to discuss future opportunities, you can do so in the body of the email. But the subject line needs to stand out to draw attention. Not only is this helpful in networking, but helps with creative communication skills moving forward.

Lillie Sun, Three Ships Beauty

Send An Interesting Article

One way to reconnect with a previous colleague or boss for networking purposes is to forward an interesting article or website. This gesture starts the conversation off with creating value for the other party instead of immediately starting the discussion with an ask. Not to mention, this tactic presents the interaction as more natural rather than transactional. Your contact may be touched or grateful that you thought of them while reading the article, and may assume that you decided to reach out as a consequence of remembering rather than with an opportunistic agenda.

Carly Hill, Virtual Holiday Party

Be Tactful

If your purpose is to try to go back to working at a company where you worked previously, be friendly with your connections at this company. Do not ask about any open positions without being warm, grateful for your past work experience with them, and wishing them well. If you simply ask about coming back to work with them and nothing else, you may come off as too desperate or demanding. It is important to be gracious and polite during this process.

Matt Miller, Embroker

Personalize Your Message

When networking, show the other person that you truly want to reconnect with them. Personalize your message by providing specific details unique to the person, such as congratulating them on a recent promotion or bringing up a topic you have discussed with them in the past. If the email appears generic, they may think you are sending the same message to multiple people.

Benjamin Farber, Bristol Associates, Inc.

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Filed Under: Career Advice Blog Tagged With: career advice, career transition, Job Advice, Job Search

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I’ve attended a few of your events in Gilbert and Scottsdale since returning to AZ and being an active job seeker. I’m happy to report that I’ve been offered a job! I’m over the moon about the offer and couldn’t be more grateful after a long, three month search (that definitely felt much longer…. 🙂 ). I want to thank you for your programs. You have excellent speakers who always energized me when I was needing it most. And your resume reviewer was great. She was a tough cookie with a red pen y… Read more
Becky T.
I own a Leadership Company, and have enjoyed attending the Career Connector events. With gratitude I listen to the speakers you line up… they offer phenominal and practical information. What has struck me each time has been the audience. My heart hurts for them. They are in a desperate place in their lives. I have had the opportunity speak with a few of the people in attendance, and they have shared their stories… I walk away thankful to God for the opportunity to meet these people and they … Read more
Bonnie M.
After a company layoff thrust me into the job market, Career Connectors was exactly what I needed to develop my networking skills. Networking is a job in itself, and the skills I learned helped me to land a temporary position just three months later that is now permanent. I believe in the Career Connectors mission and continue to volunteer as a way of expressing my appreciation for their support during a very tough time…thank you Career Connectors!
Diane N.
I just wanted to reach out to you and say Thank you to you, Career Connectors and the whole Team! So let me explain why, while I’ve known of Career Connectors for many years, I never thought that I would need employment services or guidance before. On September 19th 2019 I found myself being let go from my job. I later the next day saw the Career Connectors event at Central Christian Church Gilbert Campus coming up on Facebook and signed up for it. While attending my first Career Connectors even… Read more
Brian P.
I took advantage of Career Connectors when I found myself unexpectedly out of work and back in AZ.  The ease in using their website to locate meetings and identify subject matter at their weekly meetings kept me informed and engaged.  Their meetings are interesting and provide relevant and useful information toward getting into the right job.  They say that a network event is what you make of it … with Career Connectors they create the events and provide the resources you need to land your next … Read more
Jennifer V.
I am profoundly grateful for all of the support Career Connectors has provided during my recent job search – from the exceptional speakers to the participating employers, LinkedIn experts (Ted Robison is amazing with his individualized approach), resume experts, photographers, and of course the great opportunity to network! I felt like I had an army of support with me every single day. I appreciate all the time and effort invested by many and am particularly grateful for Jessica! You have a fi… Read more
Cindy G.
When I was laid off last year from the company I’d worked with for over 14 years, I actually found I had an even BIGGER job ahead of me. With an outdated resume, no interview skills, and a huge feeling of displacement, I went searching for help. Career Connectors was my savior. The program and its’ leaders were instrumental in rebuilding my confidence, providing the necessary tools and resources, and ultimately responsible for my landing a great position with a company that was featured at o… Read more
Lynn S.
Thank you for all you do! I’ve been nine loooong months looking for a full-time position and Career Connectors was a real life-line. I was pretty discouraged by the time I found your organization on-line and first visited. The speaker provided some great information but most importantly, encouragement and hope. The panel discussion on resumes was incredibly helpful! Last month I had the opportunity to sit with Brenda and she suggested I really pare back all but the last 10 years of experience an… Read more
Robin C.
Navigating the world of career transition can be an overwhelming experience.  In addition to the mechanics of transition (updated resume, career search strategies), there is the deeper need to connect to people who are in the same situation as you are.   For me, all of this was answered by Career Connectors!  Had it not been for this organization, I might still be sitting in my house, wondering what to do next!  At just one Career Connectors meeting you can be inspired by great speakers, … Read more
Iris M.
Career Connectors is dedicated to bring the job seeker to reputable employers in the valley. I appreciate their professionalism and their consistency to continue to provide great leads.
Leslie B.
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