The Five Emails You Need to Send Before New Year’s to Boost Your Career

Yes, you’re busy checking off your year-end, to-do list. But here’s an easy item to add that could pay dividends down the road: connect with five people who, in different ways, could boost your career in 2023.

There’s no better time of year than right now to power up that roster of professional allies. So many people have changed jobs, and entire careers, recently that even the strongest networks need some tending. And while the job market remains strong, the number of companies embarking on layoffs is climbing, and many business leaders predict more job cuts are coming.

It can be daunting to message someone you haven’t spoken to in years or develop a distant contact into a relationship. Here are five people to email, with scripts to do it gracefully.

1) A member of your inner power circle

These are the professional Samaritans for when you need urgent advice, job leads or referrals—and fast. Ask yourself who could help if you were suddenly laid off, and get results?

Try this quick exercise to figure out who belongs here: Imagine you’ve just learned your job is on the chopping block. Take five minutes to write the names of six to eight people you would email first for help.

These are folks who know you well—close colleagues, former co-workers, mentors. Focus your list on the half-dozen who are enthusiastic networkers and have a proven record delivering good intel on industry developments.

Pick one person to email. Remember, this is someone you’d have no qualms asking to tap his or her network on your behalf—so don’t sweat the email too much. Ask them to lunch or a drink in the new year, or a 20-minute catch-up call.

Be clear about why you want to connect. You’re considering ways to grow your career, and would love his or her advice. Or, you want to hear about his recent transition to a new field because you’re interested in a similar move.

2) The influencer

Next, pick a strategic contact you know could be helpful to your career…if only you had a more solid rapport.

Don’t waste valuable words in the opening on compliments or lengthy explanations.

Make your ask, quickly and politely. And please avoid the cliché phrase, “Can I pick your brain?” Instead, try one of the following:

• “I’d really appreciate your insight because you’ve been there.”
• “I heard you speak/enjoyed what you wrote/liked what you said at the meeting, especially___. I would love to hear more.
• “I’ve followed your work closely. What you did with____really resonated with me because I’m doing something similar.”

Point out any shared experiences, and be specific. You went to the same university, or are both women who trained in civil engineering. Mentioning commonalities might give them a better sense of how to help you.

“If you’re an Air Force Academy grad and you ask for time, I’m going to find it,” says Trier Bryant, co-founder of workplace consulting firm Just Work and an Academy grad who spent more than 15 years in the military.

3) The VIP

This is a higher-level professional with the ability to open the right doors, or get you to someone who can. It could be a fast-rising executive in your network. The former boss of your boss. That entrepreneur who commented on your LinkedIn post.

If you’ve never met, can a mutual acquaintance connect you? If so, offer to craft the note, or go ahead and send a brief paragraph on your bona fides and goals to guide them.

Get to the point quickly about who you are and what you want. The goal is to have your target respond “thoughtfully, in the moment, rather than delaying it indefinitely,” says Dorie Clark, an author who teaches executive education at Duke University’s Fuqua School of Business and Columbia Business School.

For example: “I’m looking to go in this direction in my career and would like your advice.” Or, “I’m interested in how you overcame this business challenge as I navigate this industry.”

Make it easy for them to accept your request. “If you ask for a phone call, make it a 10-minute phone call,” Ms. Clark says.

4) That long-lost contact

Cue the awkwardness! You haven’t talked to this person in years and suddenly you’re parachuting into their inbox, hoping they’ll remember you and, ideally, forget how much time has passed since you’ve been in touch.

Don’t dance around the fact that it’s been a while, just embrace it, says Aimee Cohen, who runs Minneapolis executive-coaching and leadership-development firm ON Point Next Level Leadership. She’s opened notes with “Blast from the past,” or “I know you might faint at seeing my name in your inbox but___.”

You can also play on the pandemic whirlwind of the past few years: “I know that it’s only been three years but it feels like 100 since we’ve last connected.”

Make clear that you remain clued into their interests and expertise, and could be helpful. For example: “I’d love to catch up and hear more about what you’re on the hunt for these days.” Or, “I know it’s been a while, but I saw this podcast about triathlons and immediately thought of you. Are you still competing?”

The classic error is to reach out after a significant amount of time with a direct ask, such as wanting help with a job search or a recommendation. You want to be approaching them, “from a position of power, not panic,” Ms. Cohen says. Explain that you’re not looking yet, but would love to learn more about their role and experience.

5) The departing co-worker

When a co-worker says goodbye, it’s an opening. “Leaving a job is a moment of vulnerability” no matter how fabulous their next step is, says Michele Woodward, a Washington, D.C.-area executive coach.

Reaching out immediately is best, but responding to a goodbye note from further back can work, too. Try starting with, “I made a note to ask you what the first 90 days was like,” Ms. Woodward suggests, or, “I made a note to ask you how work is going.”

You could also pose a timely question such as, “How are you all handling return-to-office over there?” The goal is to reconnect, picking up where you left off and moving the relationship forward.

Plan for the Future

Master the cadence of keeping up with different kinds of contacts. Here’s how often Ms. Cohen, the executive coach in Minneapolis, recommends touching base:

• Close contacts (your team colleague turned friend who left for a different company): Monthly
• Midlevel contacts (The boss you worked with for a year before they got transferred to another department): Quarterly
• Extended contacts (The guy from accounting you used to joke with by the water cooler): Twice yearly
• Acquaintances (A vendor you worked with once, years ago): Annually, sending them a note around the holidays, for example

Set a goal of contacting three contacts every week. They can be someone already in your network who’s due for their check-in, or someone new you’re adding to the rotation.

—Kathryn Dill contributed to this article.