Step 4: Reach out · topic 1 of 5

Write an outreach message people answer

Most people put off outreach because they don't know what to say. I give clients the same four-part structure for email and LinkedIn messages. A connection note is too short for all four, so use the first two and save the ask for after they accept.

The structure, in four moves

1. Open with them. Name one specific thing the company or person is doing now: a launch, a hire, a talk they gave, a post they wrote. This shows you aren't sending the same note to 50 people.
2. Give one line about you, with proof. Put your role and one result in a single sentence, such as "I run customer operations (cut onboarding time 57% last year)".
3. Connect your experience to their problem. One sentence on why your background is relevant to what they're doing.
4. Make one small ask. Ask for 15 minutes of advice, or one question they could answer by reply. Avoid "do you have any jobs?"

Asking for advice is a respected request with hiring managers and people on the team. University career centers describe informational conversations as a way to get information and advice, not a job ^[1]. And a 2015 set of experiments found people see someone who asks for advice as more competent, especially when the question is hard and the person asked knows the area ^[2].

Keep it short

I aim for under about 100 words in an email. LinkedIn's own data on recruiter messages points the same way: InMails under 400 characters got a response rate 22% higher than average, and messages sent one at a time got about 15% more responses than bulk messages ^[3]. That's data on recruiters writing to candidates, so treat it as a guide, not a promise.

LinkedIn connection notes have hard limits. On a free account you can add a personal note to a limited number of connection requests each month, and each note can be up to 200 characters. LinkedIn's help pages give the monthly number as three on one page ^[4] and five on another ^[5], so plan on three. Premium members can add notes to all their requests, with up to 300 characters each ^[5]. A request without a note is fine for people who will recognize your name. LinkedIn also says connection request limits may still apply to Premium members ^[4]. The pace in this guide, about 8 people a week, is modest.

How to reach someone you're not connected to

On LinkedIn you can usually message only your connections, with a few exceptions ^[6]. Your options, roughly in the order I'd try them:

1. Email, if you can find or reasonably work out their work address. It has no character limit, and in my experience busy managers often read email more closely than LinkedIn.
2. A connection request with a short note (see the limits above). Once they accept, send the fuller message.
3. A free message, if the person has a Premium "Open Profile" ^[6].
4. A message through a LinkedIn group you both belong to ^[6].
5. InMail, which needs a paid plan. Premium Career currently includes 5 InMail credits a month, and LinkedIn gives a credit back if the person replies within 90 days ^[7].

Who to write to

Write to the likely hiring manager, a peer on the team, or a warm link, and skip the CEO or a general inbox. The page on finding the right people covers this in more detail.

Recruiters are the exception to the advice ask. Their job is to fill roles, so be direct: name the role or the kind of role, give your one-line fit with a result, and say whether you've applied. "Would you be the right person to talk to about it?" is a fine ask. This is my view from coaching, not a rule from a study.

Sound like yourself

Be curious, not needy. You're asking to learn about their work, and you have something to offer. If you draft with an AI tool, rewrite it in your own words before you send it, so it sounds like you and says something only you would say.

It helps to know that people are kinder than we expect. In a series of studies, people underestimated by as much as half how likely others were to agree to a direct request for help ^[8]. Those were small, face-to-face requests, so the studies don't prove the same holds for email, but it's a useful thing to remember before you hit send.

What to expect

Many messages won't get a reply, and that's normal. I don't have a reliable reply rate for job seekers' messages: nobody I could find measures it well. For a rough comparison, Hunter, an email software company, reported an average reply rate of 4.5% per email sequence across 31 million cold emails its users sent in 2025, for sales, marketing, PR and recruiting; recruiters' outreach averaged 7.5% ^[9]. A personal, researched message to one person is a different thing from a sales sequence, and in my experience it does better. Still, plan on writing more messages than you think you'll need.

When they say yes

Send a calendar invite for the time you asked for, and stick to it. Bring three or four questions about their work, such as what's hard about it right now, what a strong first year looks like, and what they wish people moving into the field knew. In the last two minutes, ask: "Is there anyone else you think I should talk to?" Send a thank-you the same day, and a short note a few weeks later saying what you did with their advice ^[1]. If a role opens on their team, that's when you mention it.

Worked examples

A LinkedIn connection note (148 characters):

Hi Priya, your post on scaling clinic openings was the clearest I've read. I run multi-site ops and I'm moving into healthcare. I'd like to connect.

If she accepts, send the fuller four-part message with your 15-minute ask within a day or two.

An email to a likely hiring manager, at a company with no matching role posted (about 85 words):

Subject: Your new onboarding team

Hi Daniel,

I saw that your team is growing its onboarding group after the spring launch. Congratulations.

I've run customer operations for software teams for nine years (most recently cutting onboarding time from 14 days to 6). Growing a team fast while keeping the handover clean is the problem I like best.

Would you be open to a 15-minute call in the next couple of weeks? I'd value your view on what makes onboarding hard in your market.

Thanks, [Your name] [LinkedIn URL]

If the role is already posted and you've applied, be more direct. The next page shows how.