The best LinkedIn outreach messages are short, personal, and sent right after someone accepts your connection request. They say why you noticed the person, and they offer one small next step, like coffee or an invitation to an event. That is how Andy Milligan, founder of Columbus Marketing Organization, moves new LinkedIn connections toward real conversations.
In this live session, Andy works through his morning LinkedIn routine in real time: commenting, answering DMs, welcoming new connections, and inviting Columbus marketers to his next in-person meetup. If you are still working on how to get clients on LinkedIn, the messages below are the part that turns a connection into a conversation.
"This is a right time to at least introduce yourself, send them a message." Andy Milligan
When to send LinkedIn outreach messages
Timing matters more than wording. Andy's tip (3:10): open your network, go to connections, and the list sorts by how recently people connected with you. Anyone near the top just saw your name and chose to accept you, so they are in what he calls "that awareness phase."
He sends at least one message to everyone who accepts a connection request, ideally right away. A connection that sits for weeks with no message is just a number.
His daily routine around those messages is simple:
- Leave comments first. "Try and leave at least 10 comments every single day," he says. Comments keep your name in front of people before you ever message them.
- Answer every open DM. Keep active conversations moving before starting new ones.
- Welcome new connections. Work down the most recent connections list and send each a short, specific note.
- Track the count. Andy logs his outreach in a simple tracker as he goes. That morning he had sent at least five DMs and two emails before turning on the camera.
One caution on connection requests. Andy says he uses an AI assistant to automate sending them, then follows up by hand. LinkedIn's own rules prohibit browser extensions and tools that automate activity on LinkedIn, so keep the habit but send requests yourself. The follow-up, which is where the value is, should always be manual anyway.
LinkedIn outreach messages you can adapt
Every message below comes from one Andy wrote on camera, with names removed. Notice what they have in common: one specific detail, no pitch, and an easy reply.
After a mutual introduction:
Hey [Name]! Glad that [mutual contact] introduced us. This week is pretty busy, but I would love to get you coffee next week if you're game for it. Do you have a favorite place here in Columbus?
When something on their profile stands out:
What's up, [Name]! I just saw your [podcast, project, or post] and wanted to say that's a great idea. [One honest line about why it caught your eye.]
For a local leader or organization you admire:
Hey [Name]! Hope this message finds you well. Just wanted to say I appreciate all you guys do for [Columbus or your community].
For a new connection you would like to meet:
You and I just connected on LinkedIn and I wanted to reach out personally. I've been building my business here in Columbus and host small, invite-only meetups for marketers and agency folks. I can tell you're great at what you do. What about the chance to meet in person?
For a connection you have not spoken to in a while:
Hope this week is going well, my friend! You and I have been connected on LinkedIn for a while, and I would love to finally catch up. Lunch or coffee sometime soon?
Short welcomes count too. Several of Andy's messages were just "Glad we connected" plus one personal detail. Not every message needs a request.
Moving the DM to a real next step
The goal of a DM is a next step that happens off LinkedIn. For Andy, that next step is usually coffee or an in-person event. Here is the event invitation he sent (12:26), lightly cleaned:
While I have you, I'm hosting a small marketing leaders meetup on Thursday the 29th at North Market in Bridge Park and would love to have you. These are relatively intimate and are meant to curate good connections with other high performers in the area. So far we have [number] in attendance and I think you would get a lot of value out of it.
Three things make it work. It is specific about date and place. It explains who the room is for. And it shares social proof with a real headcount.
When someone says yes, he sends the events page, adds them to the calendar invite, and logs them in his CRM pipeline.
He tracks that pipeline by status. At 31:05 his count was 17 confirmed, 3 tentative, and 12 contacted but not yet reached, for 32 in the pipeline, and he planned to reach 50 to 60 total invitations. His lesson from the session: "Next time, I'll prioritize these guys first," meaning the contacts who matched his ideal audience. Start your outreach with the people you most want in the room.
Relevance is the whole game. In a June 2025 Gartner survey of 632 B2B buyers, 73% said they actively avoid suppliers who send irrelevant outreach. A specific, local, no-pitch message is the opposite of irrelevant. For the broader daily system, see Andy's guide to LinkedIn outreach, his warmer approach to social selling, and how he uses short videos in video prospecting.
How the Columbus community fits in
Many of Andy's LinkedIn outreach messages end with an invitation to meet people in person. That is deliberate. Columbus Marketing Organization is a peer community for marketers, freelancers, and service providers in Columbus, Ohio, founded by Andy Milligan. Members share leads, introductions, and job opportunities, including the weekly Columbus Marketing Jobs newsletter.
An event gives your message a reason to exist that is not a sales pitch. If you want a room to invite people into, see the next Columbus marketing event or join the Columbus Marketing Organization community on Skool.
The takeaway
Good LinkedIn outreach messages are not clever. They are timely, specific, and generous: message new connections quickly, mention one real detail, and offer an easy next step like coffee or an event. Comment daily, answer every DM, track your count, and send everything by hand. The conversations that follow are where clients and referrals start.
This is a right time to at least introduce yourself, send them a message.
Frequently asked questions
What should my first LinkedIn message to a new connection say?
Keep it short and specific. Thank them for connecting, mention one real detail from their profile or how you were introduced, and offer an easy next step such as coffee. Andy Milligan sends at least one message to everyone who accepts his connection requests, ideally right away.
How soon should I message someone after they accept my connection request?
As soon as you can. Andy's view is that a new connection is in an awareness phase: they just saw your name and chose to accept you. Your most recent connections appear at the top of your connections list, so work down that list every day and welcome each person.
Can I use automation tools for LinkedIn outreach messages?
LinkedIn's rules prohibit browser extensions and tools that automate activity on its site, including sending messages and adding contacts. Andy admits he has automated connection requests, but the safer approach is to send requests and every follow-up yourself. Personal messages work better when a person writes them anyway.
How do I turn a LinkedIn DM into a meeting?
Offer a specific, low-pressure next step off LinkedIn. Andy invites new connections to coffee or to a small Columbus marketing meetup, names the date and place, explains who the room is for, and shares how many people have confirmed. Then he sends the event link and adds them to the calendar invite.
Read the video transcript
Kind: captions Language: en Hey, how's it going guys? Welcome to my daily marketing channel where I build and strategize in public and teach you what's working in live time. My name is Andy and I own a solo marketing business that has generated 394K to date in just the last two years. I own three different businesses if you guys are new to the channel. One is MMG Design, which is my web and SEO studio for healthcare brands. The second is the CMO, which is my in-person events, mastermind, and job board for marketers in Columbus. And the third is my podcast called Marketing by Design, very aptly named, interviewing other marketers and high performers in B2B, healthcare, and beyond. High on some pretty cool people like Andy Cresidina, Anthony Pier, JC, Tass, Brian, and Ryan. Nice little rhyming there. Uh, so yeah, though, that's a little bit about me. What we usually do on this channel is a I'm here to deliver as much facetime and value to you as I possibly can along your marketing journey. But we usually do do that and exercise that in a traditional format. We do a little bit of live lead genen. So we'll talk to you through my daily lead generating activities, everything that I do in this dedicated block. Then we'll go on to building and strategizing in public. Talk to you guys about some of my near-term goals, the things that I'm currently focused on in order to grow grow and move the business forward. And finally, we'll focus on updates and growth stats. So, I will mindfully log all the stats and places across my company that I'm focused on growing in order to create awareness around tracking growth and creating that reinforcement loop that keeps us motivated. So, without further ado, I'm going to get right into some live legion. Um, this morning, I did just create uh let me open up our CRM here. I did just go ahead and create a new event for our next meetup which is on the 20 9th of this month. So in 15 days exactly. We have 17 confirmed attendees and I'm going to invite a few more uh while I have it top of mind. Send out a few more emails and respond to a few as well. But I think I want to mix up the weed gen a little bit today in terms of what I'm taking you guys through and show you guys a little bit of LinkedIn and how I'm focused on there. What I usually do every morning is I use quad to automate the sending of connection requests [cough and clears throat] and then I will manually uh follow up, keep the pipeline moving and u making sure that we're having active conversations on the platform per all recommendations that I would always give to anyone looking to make the platform effective. So what I'm going to do here is I'm going to open up LinkedIn. Uh first what I'm going to do is I'm going to open up my homebased app. So, I have my handy little tracker live and then I can have a reinforcement mechanism to go in and answer these. But yeah, so I can go in and log these here. Um, I have I'm a little bit behind on progress, so I've sent at least five DMs and two emails today. I think that's right. So, all right, let's dive into it. I'm going to start with a few comments. Try and leave at least 10 comments every single day. Then respond to DMs and make sure that the pipeline's moving. A little bit of wisdom and ball knowledge for you guys. If you go to network and you go to connections, these appear in order in terms of how recently people connected with you. So, whenever people connect with you, it's a really you're in that awareness phase where they have seen your name, they've validated, they've accepted you into their network. This is a right time to at least introduce yourself, send them a message. Um, which is what I'm going to spend some time doing here. I always send at least at least one message to uh the people who accept a connection request because it's just prime time and I try and do it a little bit sooner, ideally instantly. But um yeah, without further ado, I'm going to go ahead and do some of that. And then once I'm move over to email and getting the events funnel put together, uh then I will check back in. Talk to you guys soon. Hey, Grace. Exclamation point. Glad that Claire introduced us. Period. This week is pretty busy, but I would love to get you coffee next week if you're game for it. Period. What usually works best for you? Do you have a favorite time or place in here in Columbus? Do you have a favorite place here in Columbus? What's up, man? Exclamation point. I just saw your podcast name and wanted to say that's a great idea. Laughing face emoji. I played golf in college and I'm yet to get back into it and love how you guys innovated on that format. Period. Hey Jason, exclamation point. Hope this message finds you well. I just moved to the Columbus area and love that everything that you guys do for the area. Keep pushing us forward. Just wanted to say I appreciate all you guys do for this place. Hey Natia, exclamation point. Glad we connected. Period. N A T A S S I A. I love that name, by the way. Exclamation point. What's up, Trevor? Exclamation point. Glad we connected, man. What I'm going to do is I'm actually going to try and curate some healthcare people and invite them to our event. Um, which I probably should have started doing because it's very high leverage, but I'm going to go in and use the API here and log in just to kind of double my efforts a little bit. Great. Sign in. I want to ask it to pull my existing network and find people who I am either already connected to that are in healthcare that are in our area and then put them in our events pipeline and send personalized emails to them. I think that is a great idea that I wish I had thought of sooner. By the way, I also just redid the settings on this mic, so I hope it's sounding pretty good. I definitely hope it is because it's a this is a $400 microphone and b I realized it's kind of echo in here, echoey in here naturally. So, I've been really trying to focus on speaking directly into it and using Tela's uh auto features to kind of help out a little bit. But anyway, it does I do hope it sounds better. Uh be sure to comment and let me know if you have noticed. Uh just share my entire password with you guys here. Great. Um from another way. Boom. Boom. Boom. Perfect. So 66333. Awesome. Okay. So, I'm looking to invite a few local healthcare marketers into the uh my next event here in Columbus. What I want you to do is pull my existing connections, find marketers that are in healthcare and based locally here in Columbus, and then put them into a list for me so that I can then add them to folk. Does that make sense? Don't send any connection requests. just find people that I'm already connected to based in Columbus here locally so that way I can get them in the pipeline work not. Okay, we have another lead for CMJ. I will add that. Send that to Roa for her to add. By the way, I feel like every time I log in, I always have my secondary email. That's the one that's accept. That's the one that pops up first, which is just so annoying. Um short Danielle.shortgmail.com. Okay. New CMJ subscriber short. Is it two T's? It is two T's. All right. We're getting a lot of event acceptances. So that's how we're looking. Here's how the event's currently looking. Um, two weeks in advance, 15 attendees, four. Yes, one maybe. I still have several I need to invite there. Hanging in there. Haha. Period. Hope you've been well also smiley face emoji. While I have you, I'm hosting a small marketing leaders meetup in on Thursday the 29th in Dub in at North Park at North Bridge Park in Dublin and would love to have you. Period. North Market in Bridge Park. Send them to the events landing page. Boom. [snorts] Great. Nothing coo. [sighs] These are relatively intimate and are meant to curate good connections with other high performers in the area. Period. So far we have 25 in attendance and I think you would get a lot of value out of it. Period. add you to the calendar invite exclamation point. So I should go ahead and add her to fork as well. is she a freelancer now. H interesting. I thought she had a full-time job. She would definitely fit in here. Definitely. Definitely. Definitely. [snorts] Something I've been thinking a lot about recently is the reverse engineer anything. So, I don't know if you guys saw that Adobe basically Oh, he he accepted an invite, too. Aaron Faulk. Um, but someone basically vibe coded all of the Adobe apps and open sourced them. Uh, I forget what they're called exactly, but Uh they are uh essentially someone took the existing apps and basically redid them with everything on their uh like every part of the software and they look exactly the same. I forget they're like open reverse engineered Adobe apps. I forget they were called the name of them. I just sent them to Jeremy yesterday, so I should look it up here. Um, art craft. That's what they were called. [snorts] Yeah, here they are. Links. I had it right here. [snorts] Hang on. Hang with me. Uh, yes. Yeah, it's called artcraft. Everything is open source now. Reverse engineer anything. Um, yes. So, this guy basically rebuilt all of the existing Adobe applications using AI and this process called decompiling, which I thought was just, you know, genius. It's like capitalism at its purest here, right? Um, but this is I'm trying to find the damn to it. Artcraft. Yeah, here it is. Getartcraft.com. So, all of these they, by the way, it's a horrible look. Like these, this is a very vibecoded website, everything like that. But if you go, they have like the entire uh all craft apps right here. There is I'll go through these one at a time just to kind of like explain them. But if the links would work. The hell is going on here? There we go. So 13 apps, one craft. Photocraftraft is basically Photoshop. Vector craft craft is Adobe Illustrator. Filmcraft is Premiere. Lightcraft is Lightroom. PDF Craft is like Acrobat. Effect craft that is After Effects. Design Craft I think is like a mother builder. Figraft is a UI tool. Wordcraft. Word. SoundCraft. Uh Adobe Audition. And then some other uh like word tools. I will tell you these from a UI standpoint, these look exactly the same. Like it is almost crazy how similar that these look. Um which is nuts. But I I've been wanting to try them out, but I heard the performance isn't isn't as great. But yeah, just kind of an interesting moral dilemma. I encourage you guys to check those out and let me know your thoughts on like if that's a viable thing or if that's like really unethical. I'm not really sure. So anyway, I'm going to go ahead and add Aaron Folk to the invite here. Um, [sighs] let me search Aaron Folk. He is a qualified contacted aaronverianhq.com. Go ahead and add him to the invite list. Boom. Boom. good thing. By the way, I don't know if you guys use Notion Calendar, but I have been loving this for a few reasons. One is because um it's just easier. Like you can literally drag and drop and create things faster. And you can also use AI to describe like how you want to create an event. And something that's so overlooked, uh another reason is that there's more calendar colors. So, this is awesome as well. And um I just like that for organization purposes. my OCD mind. And another one is that when you add a new invite or you change an invite, you can choose to send that update without an email. So, for example, if I add a new person here, I can say send without email and it won't update everybody else in the group, which is just so nice and an overlooked feature. And I'm a big UI guy, so I just love the way that this looks. You can switch between you can add extra time zones here. You can switch between day, month, and you can change the amount of days in each view, which is just awesome. And yes, shout out to Notion calendar. Great job. Fantastic work. I can also integrate it with my notion workspace, so I see what piece of content is going out on every single day here. So, yeah, really thrilled about this. Great stuff, guys. Great stuff, Notion. I know you're watching. Yeah. So, let's get back to our invites list here. Um, I'm going to integrate. Let's check over on claude and think. Okay, give us a CSV of people locally that I'm already connected to. Nice. Nice. Good stuff. Okay. Okay. respond in chat with all of these um people and their names. Actually, can you go ahead and add these LinkedIn profiles into the Columbus marketing leaders uh pipeline within folk and add a tag to them that says healthcare. I currently have a custom field built that says member status, but I want you to add another one that says healthcare and add these people to it. Let me know if that makes sense. Still have a lot more people I could invite that are already in here. Can I think of one? K. Wilson is another one. [snorts and sighs] Hey K, exclamation point. Just reaching out to let you know I have a date finalized for the next marketing leaders meetup. Period. We have 20 confirmed attendees for October 29th, which is a Thursday, at lunchtime in Bridge Park. period. If you're in, just let me know and I'll add you to the invite. My face emoji. I hope to meet you there. Looking forward to the chance to meet you. Exclamation point www.colusmarketing.org/events [snorts] Okay, back to folk K. She has been qualified, contacted. Erin's closed one already added her of this list. We probably have three or four that are still set to I reach out to her. I don't know. Supo. This guy would be a good one to invite. I'm gonna go ahead and invite him. Did I reach out to Mumi? Majumi, [snorts] I don't have her email. So, should be a good one to buy. we've connected with on LinkedIn. So, just give me a reason. Lunch with some Columbus marketing folks. Hey, Mumi. Is it Mumi? Is that her name? I think it is. You and I just connected on LinkedIn and I wanted to reach out personally. I wanted to reach out to just personalize the intro a little bit. Smiley face and also extend an invitation to you. Exclamation point. [sighs] I've been building my business here in Columbus since 2024 and more recently have begun hosting small invite only mastermindups for other marketers here other marketers and agency folks here locally. We're planning our second one for I have for I can tell that you are great at what you do and you come across as very authentic on LinkedIn. Period. What about the chance to meet in person? Exclamation point. Cheers, Karma. I'm falling in love. [sighs] lunch with some Columbus marketing folks. Question mark. [snorts] Hope this week is doing you well, my friend. Exclamation point. You and I have been connected on LinkedIn for a while. Nope. Contacted. Okay. So, let's look at where we're at. We have 17 confirmed, three tentative, 12 contacted and not reached yet. So that brings us at a grand total of 40 even. No, 32 even. I'm stupid. 32 even. Again, I I want to get that higher. So, I'll probably get to 50 or 60 total outreach. I still have several from last time I need to invite as well. But, um, Jess, I need I definitely need to invite Jess. HDSRX. I think I have a personal email. Jess fal [snorts] wasn't personal. [snorts] Rivera X. Ah, it's Rivera X. Just focus reconnect plus lunch with some Columbus marketing folks. Question mark exclamation point. Hope this email finds you fantastically well, my friend. period. I cannot believe it's already almost the end of the year. Dot dot dot. Hope work and life have both been treating you well. reaching out because I would love to invite you to a small get together I'm hosting on the 29th of October, a Thursday. at North Market in Bridge Park. Period. Oh, mine's for Oh, typo. Dang it. Subject of mine should have been quote lunch quote with some Columbus marketing folks face pal emoji. I seems like a way back who won't mind. [snorts] smiley face emoji. [ __ ] Smiley face emoji. There should be a good mix of in-house combat agency and solo people there, which is by design because I want to curate some great conversations and connections period. Either way, we're overdue for a reconnect period. If this day in particular doesn't work, happy to. I would love to get a coffee sometime soon just to chat. Keep being a boss, Karma. Marketing. Man, I really just don't have time to proofread every email that I send. Great. So, Jess has been invited. Fantastic. Um, [snorts and groaning] we are in the qualified, contacted. Uh, definitely need to invite Tass. I'm not as worried about her saying no, though. Um, John, that's who I want to invite. I'm just going to go ahead and bring over everyone that I want to invite over to the weed comm here. I'll invite Shimento, Jason. Jason will be there. [sighs] Catherine Nate. I met this lady yesterday. She isn't We definitely [snorts] Jos. I want to reach out to this guy Josh OG. Definitely Ryan. Yep. Carrie. Yep. Jeremy Craig. Yeah. Yeah. That should be a good list. So if I read out reach out to those 16, then that'll give us 17 20 50 in the pipeline and then that should easily close from there. So yeah. Yep. Oh, max as well. Okay, so it already added all of our healthc care ones, I think. Yeah, here we go. So, I'll check what quad did back succeeded. See what is the one that already has healthcare multiple select. Okay, let's go ahead and refresh this then to see if it tagged that. There we go. Boom. Look at that, guys. Okay, so it automatically added the healthcare contacts to our list here. I'll probably depending on how I'm doing here. Again, lesson learned. Next time, I'll prioritize these guys first. But yeah, we're in a good place. 17 confirmed. Confident we'll have at least 20 confirmed here soon. And then we have these people in flux. So that's a good little portion of outreach. I'm confident with that. I want to close out on some updates and growth stats. Um before moving on to our next one. Published a video yesterday. It looked like it was doing pretty decently. I recorded this one outdoors. That's the outdoor effect. The audio didn't come across great in that one, which is a little bit unfortunate because I was using the uh the Hollywood clipon mic on my collared shirt, which didn't convert the best, but um got 21 views there. Main channel, we are at 61 subs here. Nice. 427 over there, which is great. Let's actually start to log these while I have this open. Um I'm checking these every day. subscribers, 427 and 61. Uh, four new ones since yesterday, which is great. That's the good thing about having a low number of subscribers that you literally notice every accidental change. So, if you're a new subscriber to this channel, I appreciate you and I would love for you to reach out. Um, what I did build more recently on the CMO was this ask page. And this will give you a single direction for you to reach out to me to answer any questions that you want answered or ask any questions that you want answered. Marketing, freelance, lead generation, whatever. Uh I would love to feature that in an upcoming you know live raw walkthrough as I do my outreach and things like that for the day. So encourage you to reach out here. Again you can keep it anonymous. You're totally welcome to but go to columbusmarketing.org ask. Would love to reach out to you. Um thrilled that this is live and I'll put this in the description of this video. Next uh back on to brand stats. I kind of got distracted. Are we at 8,000 LinkedIn followers? Drum roll, please. No, we're not. 7963. 7963. Boom. X. Probably the same. I think we're at 250 newsletter subs, unless I am mistaken. But we do have Roa doing outreach in an effort to grow that. So, it should be up here soon. 252. Let's go. 252, guys. Let's go. Awesome sauce. Yeah, marginal growth over time. So, in the last 30 days, we've grown 85% on YouTube, 44% on the newsletter, 2% on podcast download, which is to be expected, and 3% on LinkedIn followers, and uh 3% on the main channel. So, slow but mighty growth. How did the We dropped a podcast yesterday. Not quite sure how that was doing last I checked in. Let me view my channel here real quick. 12 views on the podcast. Yeah, not great. The vlog is doing great. I'm actually editing a vlog that I recorded yesterday and um man 180. I edited this myself, guys, and it's a very low production value video. That just goes to show like how much I think the algorithm is rewarding authentic content. And I'm going to continue doing these because they get great engagement. If I look at like the amount of likes that I get on something like that, um me go over to YouTube Studio. like the amount of likes and watch time that I get on something like that is by a concentration base is far higher than uh a lot of other content types. So if I go to I hate you. I go over here to content and I go to this vlog and go to analytics 120 views browse feature 4.5 watch hours pretty not great retention honestly but reach engagement ment the zero hypes if I let me just actually go to the channel here seven likes including me so not bad also shouting out the second channel to make a little bit of a crosspollination there but um yeah steady growth as always I'll keep you guys posted on the events and the outreach next video I'll probably focus on the podcast pipeline now that I have some great advice that I got from Chase yesterday on how to make that more effective. Um, bought a ticket to a conference and exactly a month. I'm headed to do a conference tomorrow as well in Dayton. So, that'll be a fun stressful couple days of travel as I get everything organized here. But yeah, appreciate you guys tuning in. Check out the links in the description and I'll see you guys back tomorrow. Appreciate you. Love you. Bye.