How to Approach People on LinkedIn

Lola Oguntokun
8 min readSep 26, 2022


I received a LinkedIn message from someone asking for advice a couple of weeks back, and I am yet to respond. I nearly responded several, but not to answer the call for advice, but to give advice on how to approach people on LinkedIn. This article is for that person, and anyone else who may need guidance on how to approach people on LinkedIn.

Being a professional networking platform, LinkedIn is ideal territory to approach:

  • contacts at a company you’re interested in working for
  • contacts at a company you’re interested in partnering with
  • someone who specialises in an area of interest, to build your network or gain additional insight

If you’ve never approached someone on LinkedIn before it can be daunting! How do you even start and once you start, what else do you put in the message, how do you close it off?

When you finally build up the courage to type up a message, you stop yourself, worrying about how your message will be perceived on the other side and whether it will even be acknowledged. Does it make you look desperate or too eager? Will you be considered notable enough to receive a response or the type of response you’re hoping for? Why would they even respond to you? …Naaah, I’ll just leave it.

Having spent many years in Talent Acquisition, I’ve approached many people on LinkedIn in the past. Most of which were not actively looking, all of which did not know me, knew nothing about the company I was recruiting for and quite frankly, already had enough messages coming in from other Recruiters. Despite all this, I managed to crack the shell most of the time. Here’s how.

You have nothing to lose

Before attempting to send anyone a message, it is important to have realistic expectations of the results you will get. Whether you spend hours creating a message or seconds, no one is obliged to respond to you. They either will, or they won’t.

Even when you do get a response, it may not be immediate. It could be in 2 weeks or 6 months…. and even then, the response may not be in your favour or as you hoped.

There really are no guarantees so there’s no point overthinking things. You’ll need to learn to enjoy the process by reframing your perspective and not letting your pride get in the way. You’ll win some and you’ll lose some. In fact, when you start out, you may end up losing most — don’t be afraid to lose. If you send a message and don’t get a response, though disappointing, you haven’t truly lost anything. All it means is that you’ve attempted to create an opportunity and it didn’t work out — on this occasion.

You can’t hope to gain, if you’re afraid to lose. Once I understood this, I stopped overthinking and focussed on how I could make my messages stand out enough to illicit a response, any response.

Give Them a Reason

Whenever you reach out to someone, please remember, they are busy, have their own priorities and pressure, and their own lives to live. They may not have time to respond to you and they’re not obliged to. They don’t know you and they don’t owe you anything.

The person you are reaching out to also likely receive lots of — mostly irrelevant — messages from a range of people, what makes your message worth taking the time to read?

You need to give the person you’re reaching out to a reason to care enough to read and respond.

Get to know your sender

Take the time to read the profile of the person you’re planning to approach. Don’t assume things because the person’s profile matches some key words you’ve used to find them. Check the context in which these key words have been used to ensure they are inline with what you’re looking for.

The most frustrating and insulting messages are the ones where it’s clear the person has not taken the time to read and understand your LinkedIn profile. I’ve had someone refer to a previous role as if it’s my current, I’ve had someone ask me where I currently work… and my LinkedIn profile was up to date. This has happened both with people who I approached, and with people who have approached me. On both occasions, I could not take the person seriously. If you expect me to take time out of my day to read your message, show me you have taken the time to try to understand my journey and who I am.

On the other side of this, don’t be afraid to be wrong. I’ve approached people not being 100% sure they are the right fit. Rather than ignore this, I admitted this in my message and asked for clarification, guidance or recommendations… and it worked. Humility and honesty got me through the door.


There are a lot of tips on LinkedIn messaging out there that encourage personalisation. I recommend you use a measured approach when doing this. Looking at someone’s LinkedIn profile, seeing they follow Tottenham Hotpur and starting off the approach talking about football may work for some, another person may find this extremely corny and overdone, and another a little too intrusive. Everyone is different and will not take your message the same way.

This doesn’t mean you shouldn’t try to engage people in this way, I’m just trying to point out that personalisation is more than plucking random facts from a profile. Personalisation requires a blend of putting yourself in that person’s shoes to humanise the approach and showing your personality.

In a previous article, I shared that People buy into People. This doesn’t stop being true in this scenario. Don’t be afraid to show who you are in your messages, quirks and all.

Ask yourself:

  • What would I think of this message if I received it?
  • Why would I even read it?
  • Would I find this engaging?
  • Would I respond?
  • What would make me respond?

Use these questions to get creative and be more personal and personable. Address the person you’re approaching using their first name and don’t be afraid to use emotive language. You are trying to connect with a human being, so be human!

Start Strong + Punchy

When you’re able to send InMails, you have two opportunities to engage and lose a prospect. The first is the subject line of your message, the second is how you start your message. You can still lose people beyond this point, but if the subject line is good enough, it will encourage people to read the message and if the start of the message is good enough, the person will likely read the majority of the message, depending on the length.

The subject line

Choose a short yet bold subject line. Make it a question. For instance, rather than using: “I Have An Opportunity For You” …Yawn! BORING!

Try using: “Ready to do things your way?” … Hmmm… intriguing! 😄

Using a question in the subject line is a call to action that most people will unconsciously respond to. A question requires an answer, so the natural step is to continue reading.

The start of the message

If you’re not able to send an InMail message, you won’t have the ability to add a subject line, but this is also where how you start your message is crucial.

Don’t dilly-dally here. Get straight to the point. What do you want? Why are you asking them? When explaining why you have approached that person in particular, you do need to stroke the ego a little bit. Don’t go overboard, but mentioning some things you’ve noticed about the person’s profile or experience in a positive way honestly goes a long way. You are reaching out to a human being, and by nature, there are some things we want and need in many of our interactions, even a message on LinkedIn. Again, don’t overdo it. Make sure the flattery is measured, in context and feels genuine.

The rest of the message

Once you have your subject line and start of message down, add a little more detail. Tell me a little bit more about you or the company or whatever this message is related to.

LinkedIn recommends messages are between 200–400 characters. I personally don’t feel there’s a hard and fast rule when it comes to this, as long as you feel the content is strong and punchy.

However, I completely understand LinkedIn’s recommendation, and I do think it’s a fantastic guide to follow. You don’t want to underwhelm people with too few characters, and you don’t want to overwhelm people with too many characters.

Most people are scrolling through LinkedIn as they do other social platforms — fleetingly. They don’t want to think too much when they come across a message worth reading. On top of that, they’re busy — with work and personal matters — some obvious, others not. Bear this in mind when putting an approach together.

What are you trying to achieve?

I know I should have probably put this at the beginning but I feel this is the best way to end this topic.

You should definitely not start any message without having a clear idea of what you’re trying to achieve. Are you simply trying to add a connection on LinkedIn, or are you looking to connect with a potential sales prospect or to bring someone who does not appear to be actively looking for a new role into your business?

In any of these scenarios, what is the minimum result you’re looking for? A response rather than no response? A recommendation? A conversation. Understanding the outcome you desire will enable you to tailor your message accordingly. End your message with this in mind.

For instance, if you’re hoping for a brief discussion, be bold and presumptive. Here’s an example:

“I’d love to tell you more about X and why I feel this opportunity is so special.

We can have a completely confidential and informal chat. Even if X is not suitable at this point in time, it would still be good to connect with you… you never know! 😊

When works best for you?”

When you have finished writing your message, ask yourself what you were trying to achieve. Do you feel you have achieved it? Would you respond?

Be ready to learn

Your messages should improve as time goes on, based on the responses you are or aren’t getting from people. If your LinkedIn approach never changes, you are doing it wrong.

Pay attention to how people are responding, the parts of your messages that resonate most, the parts of your messages that require clarity, and the parts that aren’t adding any value, and update your message accordingly. You will notice your results improve with every tweak.

Right — that’s me done for now. I hope after reading this article you feel better equipped to take on approaching people on LinkedIn. 😊



Lola Oguntokun

I help build, shape and champion innovative companies and culture.