The Best Time to Ask for a LinkedIn Recommendation Is Right After a Win

When's the last time you asked someone for a LinkedIn recommendation?

If your answer is "years ago" or "never," you're in good company. Recommendations are one of the most underused sections of a LinkedIn profile.

Recommendations are some of the strongest social proof you can hav. Everything else on your profile is you describing yourself: your headline, your About section, your experience. A recommendation is someone else confirming it, in their own words, with their name attached.

The good news is that getting a strong one doesn't take much. It comes down to three decisions: who you ask, what you ask for, and when you ask.

Why Recommendations Are Worth the Effort

Think about how a recruiter or hiring manager uses your profile. They're trying to answer a simple question: can this person do what they say they can do?

Your resume and LinkedIn profile make the case and your recommendations back it up. They work a lot like references that show up before anyone picks up the phone, giving a reader a preview of what the people who've worked with you would say.

If you're thinking about references, I wrote more about that in How to Choose the Right Job Reference: A Guide for Mid to Senior-Level Managers. The same thinking applies here. The right person speaking to the right thing carries far more weight than a long list of names.

Who to Ask

Start with someone who can speak to something specific and relevant to where you're headed next. A recommendation about a skill you're moving away from does less for you than one that supports the role you want.

Different people can speak to different parts of your work:

A former manager can speak to your growth and reliability. They saw how you handled responsibility over time and whether they could count on you.

A peer or cross-functional partner can speak to how you work day to day: how you collaborate, communicate, and handle the friction that comes with real projects.

A customer can speak to results and trust. This is especially valuable if you're in a customer-facing role or in sales, because it shows the impact of your work from the other side of the table.

Before you ask, look at the roles you're targeting and pick people who saw you do that kind of work. If you're moving toward project management, a cross-functional partner who watched you keep a launch on schedule will help you more than a general note from someone who simply liked working with you.

What to Ask

Skip the bare "Can you write me a recommendation?"

It's vague, and it puts all the work on the other person. They have to figure out what to say, which project to mention, and what you'd want highlighted. Faced with a blank box, the easy default is something general and kind, along the lines of "great to work with, highly recommend."

That's nice. It's also forgettable.

Instead, point them to a specific moment. Something like:

"I was really proud of the work we did on [specific project], especially [the outcome or challenge]. Feel free to use that, or anything else that stood out to you."

This approach reminds them of the work you did and gives them a great starting point. It also leaves room for them to write in their own voice, which is what makes a recommendation believable.

When to Ask

The best time to ask is right after a win.

When a project wraps up, a launch goes well, or you solve a problem someone else had been stuck on, the details are fresh. Fresh details lead to specific recommendations.

Compare that with asking a few years later, once you're in the middle of a job search. By then, the person doesn't remember the specifics anymore. They remember that you were good to work with, but not the numbers, the deadline you saved, or what made your contribution stand out.

Asking right after a win also feels more natural. You're not asking for a favor out of the blue. You're following up on something you both just experienced.

What a Strong Recommendation Looks Like

When someone does write for you, specifics are what make it valuable. Compare these two:

"Jordan is a great team player and a pleasure to work with."

"When we lost two engineers in the middle of our product launch, Jordan reorganized the schedule, kept every stakeholder informed, and we still shipped on time."

The first could describe almost anyone. The second tells a reader exactly what Jordan does well and what it looks like under pressure.

A Few Things to Watch Out For

▪  Don't let your newest recommendation be years old. A section that stops a decade ago raises questions about what you've been doing since. Aim for at least one from your current or most recent role.

▪  Don't ask people who barely know your work. An impressive title that can't speak to anything specific carries less weight than a peer who saw your work up close.

▪  Don't send the same generic request to ten people at once. A personal, specific ask gets a better response and a better recommendation.

▪  Do offer to write one in return. It's a generous gesture, and it makes the ask feel less one-sided.

Your Next Step

If you've been meaning to do this, consider this your sign.

Think of one person you worked closely with recently, on something you're proud of. Send them a short, specific ask this week, using the language above as your starting point.

If you'd like a second set of eyes on your LinkedIn profile, including where recommendations would strengthen it, take a look at my LinkedIn Profile Critiques or reach out to set up a call.

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