Subscribe to our newsletter to receive business tips, learn about new funding programmes, join upcoming events, take e-learning courses, and more.
Take the first step to successfully starting and growing your business.
Join for freePosted: Fri 30th Oct 2026
In this LinkedIn DM Roast, LinkedIn expert Jen Corcoran reviews real messages (with permission!) and shares practical ways to start better conversations, ask smarter questions and spot when it's right to suggest a call.
Because there's a difference between sending more DMs and knowing what to say, when to say it, and what to ask next.
Which common DM mistakes to avoid
How to send better connection requests
How to identify potential leads and move the conversation on
Jen is a multi-award-winning LinkedIn strategist and mentor on a mission to help driven midlife women in business toot their own horn with confidence and authenticity so they can create positive change in their own lives and in the world.
Her corporate client list includes industry giants like LinkedIn, Amazon, BT, London South Bank University, London Chamber of Commerce and the University of Exeter.
Watch more expert webinars
Access a growing collection of expert-led webinars covering marketing, sales, finance, growth and more – ready whenever you are.
Lightly edited for clarity.
Caitriona O’Connor: Hello, everyone, and welcome to today’s Lunch and Learn. My name is Caitriona, and I’ll be your host today.
For those of you attending a Lunch and Learn for the first time, Enterprise Nation is a vibrant community platform for start-ups and small businesses. I’m pleased to introduce Jen Corcoran, who’s a LinkedIn strategist.
In this session, Jen will review real messages, with permission, and share practical ways to start better conversations, ask smarter questions and spot when it’s right to suggest a call. If you have any questions throughout the webinar, please post them in the chat, and we’ll do our best to answer them at the end of the session.
Today’s webinar will be recorded, and we’ll send you a follow-up email with the recording and further resources later today. Over to you, Jen.
Jen Corcoran: Thanks, Caitriona, and hi, everyone. I’m super excited to be here. If you’ve been to any of my sessions before, you’ll know they’re a bit fast and furious, so grab yourself a pen and paper.
As Caitriona said, there’s going to be a replay as well, so don’t worry if you don’t get everything. What I’m hoping to get through today is a bit of best practice for connection requests and seven common DM mistakes, and I’m going to be doing a few mini roasts on the types of DMs that I get.
As I’m going along, if you’re thinking, ‘Oh, I’d love her to have a look at mine’, don’t be shy – you can stick it in the chat. I want to show you how to start better conversations on LinkedIn, because I know a lot of people avoid their inbox.
I chatted to one lady recently who told me her DMs were like a black hole. If this is you and you’re not sure how to get those conversations going – whether that’s for clients, collaborations or partnerships – I’m going to show you my framework, which I think is really going to help you.
If you don’t already know me, I’ve done a few sessions for Enterprise Nation. Today, I’m talking about the action part of my framework, which is about intentionally building a relevant network for you on LinkedIn, and of course DMs fall into the connect part.
If you’ve ever seen me speak before, you’ll know that there’s very much a holistic framework to getting success on LinkedIn, and you need to tick off presence, action, connect and track. If you like what I say today but you’re thinking you’re missing other pieces, do check out my training on Enterprise Nation.
I’ve got a training on profiles, one on content and one about how to get consistent clients, and they all tie in together. So off we go.
Earlier this week, LinkedIn announced that it now has 1.4 billion members. So if you’re saying that your clients or your people aren’t on LinkedIn, they are.
With that being said, I want to caveat that not everyone you connect with on LinkedIn is going to be your client. I’ve got lots of clients on LinkedIn over the years, whether B2B or B2C, and I’ve generated lots of PR, but you can’t have a copy-and-paste approach when you’re connecting on LinkedIn.
If you go away with one thing today, I’d love you to remember that even though there are over a billion people on LinkedIn, not everyone you send a connection request to is going to be your client, if that’s what you’re after. And not everyone is going to be ready for you.
At any given time, 3% will be ready for what you offer, so it’s quite a small percentage. 20% will be aware of the kind of problem that you solve as a business owner, but they might be quite passive.
All of you listening today are in this 23%. Some of you will be ready for action, and some of you will just want to know what’s going on with DMs. Then there’s the 77% who are not even aware that they have a problem.
So when we’re on LinkedIn, we really want to be targeting and chatting to the 3% and prequalifying, because not everyone is going to be our client. To add to that, some people are active on LinkedIn, some are semi-active, and some are passive.
So if you take away one thing today, remember that not everyone is ready for us, and it’s your job to prequalify – I’m going to show you that a bit later on. You can’t have a spray-and-pray approach to LinkedIn and DMs, and there’s no one-size-fits-all DM.
I’m going to show you a few examples today, but it’s very much a personalised approach for every business owner. I think the reason a lot of people hate or dislike their DMs is that people are using that spray-and-pray approach – that one-size-fits-all, copy-and-paste message – and I’m going to go into that when I do the roasts.
The first part of the session today is on whether you should personalise your connection requests. I know you’ll hear different answers from different trainers, so I’m going to give you my take.
For me, it’s a massive yes, because we’re living in a world of AI, with lots of fake experts online. It’s never been more important to show up as a human being and connect with intention on LinkedIn.
If you don’t personalise your connection request, even if it’s accepted, a week or two can pass if you don’t notice it straight away. Yes, you’re connected to that person, but neither of you is going to remember why you initially connected, so you’re essentially just collecting connections and not building relationships.
I get that if you’re on the free version of LinkedIn, you can only personalise three connection requests a month. For some businesses, it will be worth upgrading to Premium solely for the purpose of personalising.
There are ways of getting around that if you don’t want to do it. If you really want to connect with somebody, you’re on the free version of LinkedIn and you’ve run out of your three a month, I would go on to their profile, look at their latest content and comment.
Then I would send the connection request afterwards, non-personalised. That way, at least the person will think, ‘Oh, I saw them on my content earlier on.’
You have to do this in a very timely way. There’s no point in commenting and then sending them a connection request a few days later, because they will have forgotten – everything moves so fast on the LinkedIn feed.
So for me, it’s a massive yes. If you’re an unknown person reaching out, you have built zero trust with that person, and that trust needs to be earned on LinkedIn.
That’s why, when people reach out and spam us in the first message, we’re all a bit like, ‘Whoa, hold your horses. I don’t even know you.’ People are trying to rush.
I want you to think of the tortoise and the hare. The tortoise actually gets results on LinkedIn, because relationships take time to build.
You can’t fast-track them unless people are in that 3% I mentioned at the top and they’re saying, ‘Do you know what? I already know I need XYZ. I’ve just met you – let’s go.’
That doesn’t happen all the time – I’d love to say it does. This is the main reason I would say personalise, because I think we’re all bombarded with stuff online: notifications, different tech, different platforms.
So you need to get to the point quickly. Funnily enough, by being a human being, personalising and actually making an effort, you will stand out on LinkedIn, because a lot of people don’t.
If you don’t send a connection message, this is how the person will decide whether they’re going to ignore or accept your invitation. Firstly, they’re going to look at your profile and think, ‘Who is this person? What’s their name? Have they got a good headshot? Is it clear what they do?’
Maybe they’ll look down at your About section or your Featured section. They’re going to look at your recent content and activity, your mutual connections – who you have in common – and your recommendations, just to see whether this person is legit.
So yes, you could get away with no connection message if you have an amazing LinkedIn profile. If you’re thinking, ‘Right, I know my profile is amazing – it does the heavy lifting for me’, brilliant.
If not, as I said, give a bit of love to their content and comment, so that when you reach out, they will recognise you. Otherwise, I’m all about personalising.
That means personalising with context, telling the person why you want to connect with them and making it about the other person rather than you. I’ll go into this when we get to the mistakes, but that’s my take on whether to send a connection message or not.
Just to give you hope, this is a quick screenshot of one of my clients, Laurie. When she first came to LinkedIn, she didn’t have any content, so we focused purely on DMs, and she managed to build great relationships there.
By the time she had only 39 connections, she had converted two of them into clients and made £30k. So you don’t need to have a zillion connections on LinkedIn.
I imagine a lot of you have sent connection requests in the last few months and you haven’t followed up. I’ll go into that a bit later, because you probably have a lot of opportunities already connected to you that you’re not aware of.
These are the kind of good DMs that I want you all to receive, and I’d love to know in the chat box: do you get messages like this? This is what my DMs look like – speaker invites, intros to potential clients, potential collab invites and DMs from my clients.
So do you get this kind of message in your DMs? If not, this is what I want for you, because when you follow a framework that works in the DMs, these are the types of messages you will get.
If you don’t, you will get a lot of spam. In general, I find that if you’ve not fully optimised your profile, you attract even more spam.
You may not realise it, but going from connection to conversion takes a few messages. It’s not just wham bam, one message and we’re done.
I think too many people are trying to be like the hare, racing to the finish line, and they’re putting five messages into one. Ideally, this is the framework.
I’m not going to say you’re going to convert every person, because, as I said at the start, not everyone’s going to be a client. Maybe some of them will be referral partners down the line, maybe you’ll collaborate on something or maybe somebody will give you introductions.
But not everybody is going to be your client, so it’s on you to prequalify. For me, the first DM is always connecting with context.
The second DM is acknowledging that they’ve accepted and thanking them. I imagine a lot of you have sent out connection requests but not followed up, and the conversation has just disappeared.
The third DM is the transition, where the magic happens. There’s a framework and a formula to that, and I’m going to touch on it briefly today.
The fourth DM is usually when you prequalify, because somebody can reach out and say, ‘Oh wow, I loved your webinar today on DMs.’ But when I actually dig deep, they may not be an ideal client; they may not be ready to take action now, and they may have no intention of ever investing in LinkedIn.
It’s up to you to prequalify, and DM five is convert. The problem with a lot of people on LinkedIn is they’re trying to ram all five of these messages together into one, and they’re not prequalifying.
They think everybody is their potential client, and they’re sharing links to their calendar or their next webinar, and it’s like, ‘Oh my god.’ You need to qualify and figure out where that person stands in your network.
So it’s the tortoise and the hare – going a bit slower and following the natural rhythm of a conversation. Imagine if you went to a networking event and bamboozled somebody straight away: ‘This is what I do. This is why I can help. Blah, blah, blah.’
It’s like, whoa – you have to have a bit of back and forth, a bit of ping-pong. It doesn’t take too long, but I think most people have heard LinkedIn is good for getting clients, so they treat it straight away as somewhere they can just reach out with that one message, and they forget that it’s a social network where you have to actually build relationships.
Here are the seven most common DM mistakes that I see. There are a lot of them, but these are the most common.
The first is not using DMs at all – like I said, I just spoke to someone who told me her DMs are like a black hole. The second is no connection message, so the person is thinking, ‘Who is this person? Are they going to sell to me? Are they going to spam me?’
Starting with a pitch is a classic one. When you start with a pitch and you’re focusing on me, me, me, it puts up barriers for the other person and people just switch off.
Next is overfamiliar questions too soon, and I’m sure some of you can relate. I usually get them coming up to the end of the year or in January from a lot of coaches asking me what my goal is for the year, and then they go quite deep.
I think, ‘I don’t even know you. I haven’t even discussed this with my husband – why should I be telling you my biggest business wishes?’ So that’s overfamiliar questions too soon, fast-tracking the relationship.
Then there are long messages, like War and Peace. This is a social network – this is social media – so short and snappy is what you need.
You need to be willing to get into the flow of the conversation. I know it’s hard when you really just want to tell them about XYZ, and that’s why a lot of people condense everything, but it’s just too much.
Next is no follow-up system. Again, people connect, and then that’s it – silence, crickets.
Then there’s using DM automation, which is just really gross. People can tell when it’s automated, and you also risk your account being shut down without warning, because you should be a human being in your LinkedIn inbox.
So these are the most common DM mistakes. I’d love you to share in the chat box the numbers of the ones that you’re doing, so you can all see that we’ve all been guilty.
Some of us have sent long ones, some of us haven’t followed up and some of us haven’t sent a connection message. I’d love you to see amongst each other what your common mistake is, so don’t be shy.
I’m going to get into the bad DMs now and roast a few – just a quick sip first. These are screen grabs of ones I’ve received, and I’m going to break them down a bit more in the next few slides.
I’m sure some of you have got ones like this: just ‘Hi’ or ‘Hi, ring me’, and you’re like, ‘What?’ The first one I’m going to chat about today is a vague one, and it’s clearly automated.
You get something like this and it’s just so spammy, because we’re all time-poor. ‘Hi LinkedIn member’ does not make me feel special.
If you want to get results on LinkedIn, you really need to personalise and make it about the other person. If I get something like this, it’s like any of those cold, spammy emails I get in my inbox every day, and I can’t be bothered to engage.
On the flip side, as I said, you can get super-specific messages asking about your goals, your lifetime goals and what’s happening this week, and you’re like, ‘Whoa, I don’t know you.’ So you’ve got the reverse of this.
I think in a world of AI, sending anything like this is not really going to build any trust. Luckily, I don’t get too many of these.
This is a standard one: the overfamiliar intro pitch, where people cram the five messages into one. It’s not a terrible message, and it would be great if we were on DM three or DM four – it’s just too fast, too soon.
They want to connect and tell me all about them. But if your profile’s working for you, you don’t need to tell me you’re a professional graphic designer – I can see that.
So many people do that in DMs as well. Another annoying one is ‘Tell me about what you do’, and you think, ‘You’re the one that reached out to me – you should be able to see it from my profile.’
This is a typical one: it’s not a terrible length, but it’s too much, too soon. This next one is like War and Peace – way too long for a LinkedIn DM.
When you actually read this one, it’s tone-deaf, and I’m sure you’ve all had them. This is somebody telling me about their new service, Linkcredible, and how I can basically use automation on LinkedIn.
It’s like, ‘Hello? Have you looked at my profile? Have you seen what I do?’ The first thing that’s wrong is there’s no prequalification – it’s tone-deaf, and they’ve not looked at my profile.
The second is that it’s way too long. The third mistake is they’re asking to go on a call straight away, and it’s like, whoa – we’ve not built any relationship and you don’t know anything about me.
I’m sure you can relate to some of these. As Caitriona said at the start, if you’ve got any messages you want me to roast, don’t be shy – stick them in the chat. All roasts are done with love.
Now I’m going to tell you about my Doctor Method, which is what you need to be using on LinkedIn to generate opportunities, whether that’s clients, collabs, partnerships or anything else. It’s all about leading and prescribing like a doctor.
When you’re the doctor, people come to visit you, and that’s the approach you need on LinkedIn. You need people to come to you – you don’t need to go out chasing everyone.
I’m talking about warm leads and warm buyer signals in this session. If that’s not you yet, I totally get it, and don’t be shy to reach out and chat with me, because you need to warm your audience up to get them to the stage of having that sequence in the DMs.
I’m going to break this down into five warm buyer signals in your LinkedIn DMs. The first is people reaching out to you and mentioning that they’re struggling with what you do – for me, that’s anything to do with LinkedIn, such as algorithm reach.
The second is that they compliment you on something. For example, I’ll get a DM later on saying, ‘Oh, great webinar, I loved it.’
So that’s struggling or a compliment. They also seem very keen to chat, so they’re giving you lots of information, and they’re very engaged – it’s not just one-liners.
They’re sending detailed answers and they’re asking you lots of questions, just as you would engage with a doctor. These are the five warm buyer signals, and this is how you know this person is potentially a lead.
If you’re not getting these signals, you shouldn’t be trying to convert those people. These are the people you want to focus on – the 3% who are potentially ready to buy, or the 20% who know they’ve got that problem but just haven’t taken action yet.
We don’t want to be focusing on the 77% of people who haven’t got a clue why they would need what we offer. Now I’m going to show you how you can do an elegant pivot and get the conversation moving.
So what do you do next if you get any of those signals? There’s a three-part framework that you should follow – it doesn’t have to be word for word, but you do need to follow it in roughly this order.
The first is to acknowledge them. If Mary’s reached out and said she loved your webinar, I’d say, ‘Hi, Mary, thanks for that.’
Acknowledge what they’ve said first, because a lot of people don’t – they just go straight into what they do. The second part is pad to soften.
The reason I say this is that if you don’t do some kind of little padding on LinkedIn and you’re too direct, people can think it’s too much, too soon. A little bit of padding goes a long way.
Some people might say ‘just out of interest’. For example, I could say, ‘Hi, Mary, thanks for your kind words. I’d love to know…’ or ‘Just out of interest…’, and then you’ve primed them and you ask a question.
You use their language, and I’m going to show you in the next slide what that would look like for me after a compliment on a webinar. This is how I would pivot: ‘Thanks for the kind words, Mary. I’d love to know what exactly you found most inspiring.’
Say they said, ‘Your webinar today was inspiring’ – you have to use their wording back. When you do that, it will start a targeted conversation, and it’s going to show how that person sees you.
Then you can pivot the conversation accordingly. If you just say, ‘Thanks, Mary, have a great day’, the conversation goes flat.
If you don’t ask a question, it’s just going to go flat, so you need to be willing to get into that conversation flow. I’m sure a few of you will be feeling excited, confused, or maybe a combination.
LinkedIn DMs, especially if you’re using them for sales and getting clients, are nuanced. There’s a lot to it, and it’s one of the main things I cover with my clients.
So if you’re wondering how to do it in relation to lots of other things, don’t be shy to reach out and connect. I just want to remind you again, like I said at the very start, that when you’re unknown, there’s zero trust.
You need to earn it on LinkedIn and build that relationship – you can’t wham-bam it. If you do want to build that trust, these are my contact details, so don’t be shy to reach out and connect with me.
I’m going to check the chat box now and chat to Caitriona. Thank you for listening to me – I know it’s been a very fast one, but we only have half an hour and there’s a lot to this.
So I’m going to stop my share and look in the chat box to see what’s been happening. Hi, Caitriona.
Caitriona: Thank you. Let’s start with this question from Jonathan, who’s asking, ‘What do you think about offering a freebie in the relationship-building process, and when would you include it?’
Jen: Oh yes – once you’ve prequalified, so I wouldn’t be offering it straight away. I think that’s what people do wrong: ‘I’ve just done this, blah, blah, blah’, and you’re like, ‘It’s too soon.’
I wouldn’t be mentioning it until at least the third or fourth message, not in the first or the second. The first message has to be about them, especially if you’re reaching out – it’s why you want to connect with them, and you want to make them feel special.
The second is that acknowledgement: ‘Thanks, great to connect.’ If you’re lucky, the person starts chatting and says, ‘Yeah, great to connect’, and you’re already in a conversation.
With the freebie, I think years ago it really worked, especially back in pandemic times – it worked a lot quicker, and you could have put it in the first or second message. But now I think people are just inundated, so you really need to build that relationship first.
If you’ve got a great freebie, have it on your profile – put it in your Featured section for when people are looking down. You’ll see mine if you bring up my profile: my freebie is a free webinar.
So I know if people are checking me out and they’re a bit nosy, they’re going to click in there. That’s how I would lead with it – it is a good idea, but not straight away.
It’s asking for permission, really, isn’t it? It’s about saying, ‘Would you like that? Would that help you?’, and there’s no point in offering it to somebody who has no interest whatsoever.
Caitriona: Thank you. Do you think LinkedIn DMs are becoming less effective because people are receiving so many? And if so, how can we stand out?
Jen: I don’t think they’re becoming less effective. I think people are focusing more on what they’re receiving than on what they’re doing, and they don’t have a proper tracking system or a proper way to follow up with relevant people.
So I think they’re just getting flooded by what’s coming at them. I know it’s easily done – it’s the same with content on the home feed, where you can fall down the rabbit hole and scroll and scroll.
But when I go on LinkedIn, I’m very much in a strategic mindset. I give it half an hour a day, I have specific goals and I focus on what I need to do in the DMs, as opposed to what’s happening to me.
So I think it’s about taking control. If you had two or three really quality conversations in the DMs every day, that would be far more impactful than wasting your time on a post that just dies in the feed.
So I don’t think they’ve lost their impact. I think a lot of people haven’t had LinkedIn training, or they’ve never learned how to do social selling.
LinkedIn is a very different platform from Facebook or Instagram – it’s about relationship building. If you’re using it for client conversion, you’re going to need to learn sales techniques and social selling.
I didn’t have this at the start of my business, and I’ve been in business nine years. Before that, I was in corporate, and I loved LinkedIn and was chatting away, but I wasn’t trying to sell to anyone.
I was really good at LinkedIn; I built my brand, and it gave me amazing opportunities as an employee. But when I became a business owner, I thought, ‘[expletive], I don’t really know the nuances here.’
So there’s definitely sales training and social selling that needs to be learned, and it’s not something that comes naturally. It didn’t come naturally to me, and I’m a good connector, so I think not enough people know how to do it.
Caitriona: Thank you. Vaishali has a question in the chat. They’re asking, ‘When people send me a message and I don’t know them, I usually ask them, out of curiosity, why did you connect with me? Is that OK?’
Jen: Yes, that’s good. You might want to soften it a little and just say, ‘How did you find me?’, rather than ‘Why did you connect?’
I do it all the time. I’ll just say, ‘Hi, Mary, thanks for reaching out. How did you find me?’, with a smiley emoji or whatever.
Just keep it light and breezy – that’s an absolutely fine message. It’s absolutely your right to know why they’ve reached out, because it’s your network, and if they’re connected to you, they’ll probably be able to see all of your connections. So yes, absolutely – it’s a good question.
Caitriona: Thank you. We’re just coming to the end of the session now, but we do have time for one final question. What is one LinkedIn messaging habit you would encourage everyone to stop immediately, and one habit they should start?
Jen: Oh yes. The habit to stop is trying to pitch in the first message and trying to cram five messages into one.
The one they should start is the second DM, the acknowledge and thank, because I think so many people ping off these requests, the person accepts and then they just ghost them. It’s like, why did you send that person a message?
I’m sure you could all go through your DMs and the connections you’ve made in, say, the last three months – this is a good bit of homework. Have a look and see whether you actually followed up and said thank you for connecting.
It’s a good thing you could do today. We’re nearly at Halloween, so you could say, ‘Oh my god, I can’t believe it’s nearly Halloween – I’m so sorry I never came back to thank you. I can see where we connected.’
You could start a conversation and ask if they’ve got any good Halloween plans. Or just say, ‘I look forward to reading your content’ – something that carries on from the first message you sent them.
So that’s a good thing for everyone to do today. Have a look and see who you sent a message to and then never followed up with, because the magic really tends to happen from the third message on.
That’s an easy one to pick up. I think we’re all guilty of it – I’ve been guilty of it as well when I’m on the fly on my mobile and I ping off a request, because it’s not as easy to personalise on the mobile app, and then I’m like, ‘Oh god, how did I know this person?’
In general, if you’re really in client conversion mode, I would say do it from your desktop, because you’re a lot more focused and you can personalise a lot more easily. But we’ve all done the quickie, so it’s always worth looking back at those new connections, pinging in and seeing what the message was – and if there’s no message, definitely start one and say hi.
Caitriona: Thank you so much – it’s a good way to end the session. Thank you so much, Jen, for your presentation today, and thanks to everyone who joined us. We’ll be sharing the recording and further resources in the follow-up email this afternoon.
Jen: Thank you, and happy Halloween to everyone. I hope you all stop receiving horrible DMs and stop sending them. Take care, everyone, and bye.
Unlock more on-demand sessions designed to help you sharpen your skills, grow your business and stay one step ahead. Find more Lunch and Learn webinars
