The Long Game of LinkedIn: how to reach out without selling your soul

We help a lot of clients with LinkedIn outreach here at Chief. It’s something we’re seeing more and more, probably because it’s free, relatively easy, and when it’s done well, it’s genuinely effective and rewarding.

I’m not talking about becoming a thought leader. Most people don’t want that, and that’s fine. What they do want is to connect with others in their world. Maybe it’s finding potential leads for their product or business. Maybe it’s starting conversations ahead of a conference. Sometimes it’s just about building relationships now, so they’re there when they might need them later.

It’s the long game of LinkedIn strategies.

For those founders wondering what the hell they should be talking about online, in terms of content and posts etc, check out my previous article, 'Founders, You Only Need to Be an Expert in Your Own Product!

The problem with a lot of outreach these days is that it just feels... off. Too formal. Too forced. Too focused on trying to get something. Too many people treat it like a funnel. Or they overthink every message — trying so hard to say the right thing that it stops sounding like them at all.

Being thoughtful about what you say is a good thing. But many people end up focusing on the wrong stuff — like getting a response at any cost or sounding overly polished. Then there are those who don’t do anything at all. They leave their profile untouched and just hope someone stumbles across it and gets in touch. That doesn’t work either. What matters more is being clear, relevant, and easy to talk to.

Step one: don’t start weird

If you’re reaching out to someone, send a connection request. That’s the whole first step. You don’t need to say much, and sometimes, you don’t need to say anything at all. However, if you don’t have any shared connections or obvious overlap (no mutual contacts, no shared groups, no real context) then it’s worth adding a short note. Just a line or two. Without that, the request can feel random or, worse, automated. A little context makes it easier for the other person to say yes.

The most important thing at this stage is that your profile has to do some work. If someone checks you out, they need to understand (quickly!) who you are, what you’re working on, and whether there’s a reason to connect. Most people will make that call in a few seconds, so it needs to be clear at a glance.

Quick note: your connection rate depends on more than the message and your headline. Things like your profile picture, about section, and any shared context play a huge role in whether someone hits accept, so it’s worth making sure all of that’s in good shape first.

Your headline might just be your job title, and that’s fine. But it should be current and intentional, the one thing you want people to know about you right away. The same goes for your About section. It doesn’t need to be long or perfectly written. It just needs to show that you’re active, paying attention, and giving people some immediate sense of what you’re focused on. Not a résumé, just some context.

Assuming your profile’s in decent shape, a short message might help your request feel more personal, especially if you don’t have mutual connections.

Something like:

“Hey, saw you’re doing some great work in [topic] — thought it’d be good to connect.”

That’s enough. It shows you’re a real person and you’ve made a bit of effort without trying too hard. Don’t follow up straight away. Let them connect or not. If they do, then you can move on to the next part.

Step two: just be normal

Once someone connects, resist the urge to sell anything. Just say hi.

“Thanks for connecting — always good to find other people in this space [be specific about “this space”].”

That’s it. A small, polite acknowledgement. You might even find you don’t need to send it, because they do it first. If that happens, great, just send a friendly reply back.

Then leave it alone for a bit. This isn’t the moment to force a conversation. It’s time to start showing up in the background. To be visible in a low-key, consistent way. Like some posts that you genuinely like. Comment if you have something to say. The more thoughtful and consistent your comments, the more likely people will start recognising you. Passive engagement helps, but it’s the quality of what you put out there that builds trust and mental association over time.

Share thoughts or updates when they come to you — not every day, and not because someone said you should post 5 times a week. Just when it makes sense. It doesn’t have to be polished or profound, just something real. Even occasional posts can help people understand what you’re about, and create interest.

This kind of presence-building takes time. But it works. People start to recognise your name. They start to associate you with certain topics or ways of thinking. They see what you care about, and they start to care back. It’s passive, but not lazy. Quiet, but intentional. And it sets you up for better conversations later on.

And no, not everyone will engage. Some people won’t reply. Some won’t react. That’s fine. Don’t chase it. Don’t take it personally. Just keep going. You're not trying to win everyone, you're trying to stay visible to the right people.

Step three: speak up when it feels mutual

Eventually, some of your connections will warm up. They’ll like your posts more regularly. Maybe they’ll comment quite a bit, agreeing with you or complimenting your opinions or updates, etc. You might end up in a quick back-and-forth in the DMs. That’s your cue, not to pitch, just to start mentioning what you’re working on. Though not always, and that’s fine. A lot of outreach goes nowhere. It helps to periodically look at who’s engaging and focus your energy there. Cold connections that stay cold forever aren’t a reflection of you, they’re just part of the process.

But again, only reach out when it feels natural. No need to rush it. You’re just picking up on a bit of momentum (maybe a shared interest, a bit of curiosity) and offering something relevant in return.

Something like:

“Hey, I’ve been enjoying your posts around [topic] — I’m working on something that might overlap a bit. Happy to share more if you’re curious.”

That’s all it needs. You’re not pushing. You’re not redirecting the conversation. You’re just adding something in, gently. If they’re interested, they’ll say so. If not, no big deal.

The timing matters here. If you bring it up too early or come in too heavy, it feels like the connection was just a pretext. But if you’ve been around, contributed a bit, built even a small amount of trust, then this kind of message feels like the natural next step, not an awkward sideways move.

Some simple rules worth repeating…

Make your profile worth looking at.

It doesn’t have to be fancy,  just clear, up to date, and honest. Your headline should reflect what you do now. That could be your role, your focus, or just the thing you want people to know at a glance. Your About doesn’t need to be long, but it should give a good amount of context. What are you into? What are you working on? Where’s your attention right now? What do you want people to know?

Be consistent, not constant.

You don’t need to live on LinkedIn. But you do need to show up. If you see a post you like, hit like. If you’ve got something to say, leave a comment. If there’s a thought that’s been sitting with you, write it up. It doesn’t need to be long or polished; it's just something real that you care about or are an expert in.

What matters most is that you don’t disappear for weeks and months at a time. You don’t have to stick to a schedule, but consistency builds recognition. It shows you’re around. And yes, the algorithm tends to favour people who post, comment, and like things regularly.

Let conversations breathe.

Some people reply straight away. Some take a few days. Some never respond at all. That’s just how it goes. Don’t chase. Don’t hover. Don’t try to turn every message into something more. You’re not trying to close a deal, you’re starting (or continuing) a conversation. That means giving it space to grow, or not.

Don’t fake it.

People can sense when something’s being done out of obligation, or strategy, or box-ticking. And that’s the fastest way to make someone switch off. If you’re only engaging because you think you should, it’ll come across that way. So don’t. Be yourself. Be genuinely curious. That’s more than enough. Templates and prompts can be useful if they’re a starting point — just make sure the message still sounds like something you would say. The goal isn’t to avoid all structure, it’s to avoid sounding like you’re a robot.

Final thought

The best outreach doesn’t feel like outreach. It feels like a conversation between two people who are genuinely interested in the same thing, or heading in similar directions. That’s where trust starts, not in the message itself, but in the context around it. The timing. The tone. The intent. If it’s not just a tiny bit fun, you’re doing it wrong.

It’s easy to overthink this stuff. But the reality is simple. Be consistent. Pay attention. Be clear about what you’re working on and why it matters. Talk like a person. That’s what makes people want to interact with you.