Keeping In Touch With Your Former Boss: The Importance of Staying Connected

Your former colleagues and supervisors are a certifiable networking goldmine: They know your background, they work in your sector, and they have their own set of professional contacts. They can put a good word in for you at a new job, write you a letter of recommendation for grad school, and introduce you to new contacts and opportunities. And at the very least, they can confirm to a potential employer that you performed tasks X, Y, and Z at Corporation ABC.

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So why are we so bad at staying in touch? Well, because it takes time, and because it can be awkward—if you don’t have a particular reason for reaching out, it can be hard to know when and how to do so. But periodically touching base, even when you’re not job-searching, means that when you do need to ask for a letter of reference or contacts in a new state, it won’t seem self-serving and out of the blue.

To help you out, we’ve come up with five easy ways to stay in touch with those old co-workers. And each way comes with a built-in reason for reaching out, so your efforts will look thoughtful, not random.

You can say “Best Wishes for the New Year” to anyone. It’s collegial, it’s professional, and it’s on your holiday to-do list anyway. Added bonus: Think about how you feel when you receive a holiday card—like someone really cares about staying in touch with you (at least once a year).

The most professional choice is a non-denominational card (unless you’re certain about what tradition he or she personally observes) that steers clear of humor, which can be seen as offensive.

Staying connected with former bosses and colleagues is an essential part of career development and networking. While the internship may be over, the relationships you built don’t have to end. Maintaining contacts can lead to future job opportunities, mentoring, letters of recommendation, and more. Here are some tips on how and why to stay in touch with former employers:

The Benefits of Staying Connected

  • Future job prospects – Your former boss already knows your skills and capabilities. When positions open up, you want them to think of you first.

  • References – Bosses and colleagues you stayed in touch with are ideal candidates to serve as references on job applications. Their glowing recommendations can give you a leg up.

  • Industry advice – Those in leadership roles often have their finger on the pulse of industry trends Keeping them as contacts allows you to seek their expertise,

  • Networking opportunities – Your former boss likely has many high-level connections. By staying in touch, you may gain access to their network and contacts.

  • Mentorship – Some former managers make great mentors that can provide ongoing career guidance and support But they can’t mentor you if you lose contact

The bottom line is that relationships matter. Put in the small amount of effort needed to maintain your professional connections. It can pay off for years to come.

How Often Should You Follow Up

There’s no exact science to the follow-up process. Every relationship is unique. However, a good rule of thumb is to check in 2-4 times per year. For example:

  • Once every 3-4 months
  • During the holidays
  • When you achieve a career milestone like a promotion
  • Before embarking on a job search

A quick email, LinkedIn message, or even mailed note lets them know you value the relationship. Be careful not to pestering them with constant contacts. Gauge their level of response to determine appropriate frequency.

Best Practices For Staying In Touch

Follow these tips to make your follow-ups meaningful and enhance the relationship:

  • Personalize messages – Avoid canned templates. Mention specific memories, inside jokes, or meaningful experiences you shared. This shows thoughtfulness.

  • Share career updates – Brief them on new jobs, promotions, internships, or other progress. But don’t make it all about you.

  • Ask insightful questions – Inquire about their job, new initiatives at the company, industry trends, or general career advice.

  • Express appreciation – Thank them for the skills you gained during your time working together. Bosses like to know they made an impact.

  • Offer assistance – Ask if there is anything you can help with, even informally. Making yourself useful strengthens the bond.

  • Connect on LinkedIn – Stay updated on their job changes and share relevant content. But don’t stalk excessively.

  • Suggest meeting up – If geographic proximity allows, propose meeting for coffee or lunch to catch up. Face time can reenergize the relationship.

Following Up at the Right Time

When’s the best time to initiate that first follow-up contact? Strike when the iron is hot:

  • At exit interview – This is a perfect opportunity to get their contact info and express interest in staying connected.

  • On your last day – Say you hope to keep in touch and would appreciate being considered for future opportunities.

  • 1 week after departure – Thank them for the opportunity and reiterate you’d like to maintain the relationship.

  • When major news breaks at the company – Check in acknowledging the news and ask how it may impact their work. Shows you’re plugged in.

The key is to reach out soon after departing when you’re still fresh in their mind. But don’t contact them constantly right away. Spread follow-ups out over time.

Following Up Without Being Annoying

You want to stay top of mind without becoming a pest. To avoid annoyances:

  • Don’t stalk excessively on social media – Occasional likes are fine. Commenting on everything is overkill.

  • Avoid frequent unsolicited messages – Emails/texts every week are too much. Gauge their level of response and adjust accordingly.

  • Don’t overshare personal details – Your former boss isn’t your therapist. Keep conversations professional.

  • Don’t always ask for favors – If every message asks to pick their brain or make introductions, it appears self-serving.

  • Respect their time – Keep communications focused and compact. Don’t expect them to devote extensive time to you.

  • Use proper etiquette – Address them by last name unless told otherwise. And avoid slang or sloppy writing.

You want them to look forward to your occasional check-ins, not dread them because you always want something. Keep that balance in mind.

Offering Help And Expertise

Successful networking relationships are reciprocal. Avoid making the exchange solely about you and your needs. Look for opportunities to offer your help and expertise:

  • Share articles or content – If you come across something relevant to their work or industry, pass it along.

  • Provide industry intel – Offer insights and trends you’re seeing that may impact their role or company.

  • Give advice – If they’re seeking input on a problem and your experience allows you to help, offer your thoughts.

  • Offer to guest post – If your former boss runs a company blog, volunteer to author a post. It’s a chance to showcase your expertise.

  • Spread the word – Where appropriate, promote their company to those in your network by sharing positive news and achievements.

  • Provide referrals – If you know someone who would be a good candidate for open roles at the company, make introductions.

Helping others builds goodwill and deepens the relationship. Just be sure your offers of help are genuine and not purely self-motivated.

Avoiding Burning Bridges

In rare cases, a boss relationship may end badly. Perhaps your personalities clashed or they behaved unprofessionally. Even in these situations, avoid burning bridges:

  • Take the high road – Don’t sink to unprofessional behavior in retaliation. Handle the situation with maturity.

  • Avoid public negativity – Refrain from bashing your boss publicly on social media. It reflects poorly on you.

  • Don’t make accusations – As difficult as it may be, try to give them the benefit of the doubt. Forgive and forget minor slights.

  • Keep interactions cordial – If forced to interact, kill them with kindness. You never know when paths may cross again.

  • Move on – Ultimately it’s best to move on and invest energy in more positive connections. Learn from the experience.

With effort, even strained relationships can potentially be salvaged. But forcing a connection that fizzled may be wasted effort. Focus on more promising contacts.

Other Key Connections To Maintain

While bosses demand focus, don’t overlook other valuable connections:

  • Peers – Fellow interns and entry-level colleagues make great lifelong friends and professional contacts.

  • Mentors – More-experienced mentors who’ve guided your career are invaluable to keep in the loop.

  • Senior leadership – Executives other than your direct boss are worth nurturing, as they may influence hiring.

  • Clients/vendors – Key business partners from initiatives you worked on together are worth cultivating.

  • HR staff – HR pros can provide references and keep you top of mind for job openings.

  • Internal champions – Managers other than your boss who appreciated your contributions make influential allies.

Reaching out to the full spectrum of colleagues strengthens your safety net. You never know who will end up at companies you’re interested in down the road.

Tools To Cultivate Your Network

Utilize these tools to build ongoing dialogue with all your professional connections:

  • LinkedIn – Your profile and activity keep you on their radar. Make sure yours is robust and active.

  • Email – Brief check-in emails on major events are often appreciated. Just avoid overdoing length or frequency.

  • Social media – Commenting on and sharing their posts fosters organic interactions and visibility.

  • Texting – More casual check-ins by text are fine for peers you worked closely with. But avoid overtexting bosses.

  • Phone/video chats – Occasional short chats are great for a quick catch-up. Just be respectful of their time.

  • In-person meetups – When possible, grab coffee, meals or drinks. Face time can strengthen dormant relationships.

  • Handwritten notes – For senior leaders, a thoughtful handwritten note can make a memorable impression.

Networking Is a Long Game

Staying connected with former bosses and colleagues is not a short-term play. To maximize your network:

  • Start early – Begin cultivating

staying connected to former boss

Major (Personal) Life Events

Are you moving and mailing change of address cards? Are your name and email changing post-marriage? Send a “here’s my new contact info” note to your old colleagues and bosses as you would to your friends and family. When you share that you’re getting married, going to grad school, or pursuing your life-long dream of traveling abroad and writing that novel, it not only shows that you’re interested in staying in touch, it fosters the personal aspect of your professional connection.

Major (Professional) Life Events

Did you just change jobs or get a promotion? Let your old bosses know, and thank them for the experiences they’ve given you that helped you get to this point. You can do this for non-job-change accomplishments, too. For example, if you’ve been chosen to throw a major event, send a note to the effect of “Im running a 500-person event, and it reminded me when you gave me a shot at throwing my first gala.” If you’re in the same city, even better if the note is enclosed with an invite.

This can work both ways, too—if you hear that a former colleague has changed jobs or won an award, send her a “Congrats” card or email.

Jordan Peterson, this is how you TALK TO YOUR BOSS. Bringing up problems without being one.

Why should you stay in contact with your former boss?

From professional development to receiving positive references, maintaining a relationship with your former employer can contribute to your future success. In this article, we discuss five reasons you should stay in touch with your former boss and offer tips to help you stay in contact.

How do you keep in touch with a former boss?

Here are five ways to keep in touch with those old employers without looking too desperate. Social media is the easiest way to stay in contact with a former boss or colleague after parting ways. There are many forms of social media but professionally, LinkedIn is the best way to stay in touch with a previous manager.

Should you have a relationship with your former boss?

“The best part about having a great relationship with your former boss is that they can also open doors outside your old company,” says Ginny Soskey, a marketing manager at Shareaholic who also presents networking workshops to collegiettes.

What should you do if your boss interferes with your life?

You also need to respect their personal and professional choices, and not judge them or compare them to your current boss or situation. Moreover, you need to communicate your own limits and preferences, and not let them interfere with your work or life balance.

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