Sales prospecting is the repeatable work of finding the right people, starting conversations with them, and moving them toward a sales call. The version that works for a solo marketer is not a burst of activity. It is a small system: a defined list, a fixed daily cadence, honest tracking, and follow-up that never depends on memory.
This playbook breaks down the business development routine Andy Milligan runs every weekday. Andy is the founder of MMG Design and Columbus Marketing Organization, and his solo marketing business has generated close to $400,000 in lifetime revenue over about a year and a half. In the video at the top of this page, he works his pipeline live for about 40 minutes. Below, that session is turned into a sales prospecting process you can copy, with time estimates, pitfalls, and a checklist.
If you are still working toward your first paying client, start with our guide on how to get your first client, then come back here to build the system that keeps the pipeline full.
"Obviously, I don't get there every day. That's the point of this accountability." Andy Milligan
Who this sales prospecting playbook is for
This is for freelancers, solo consultants, and small agency owners who sell services and have to generate their own pipeline. You do not need a sales team. You need about an hour of focused time on weekdays and a place to log what you do.
It is different from our playbook on how to generate leads, which walks through one hour of daily outreach activity. This page is about the system around that hour: who goes on your list, how you decide what to work first, what stages a prospect moves through, and how you review the whole thing each week.
The outcome: a prospecting routine you can run on a bad day, with every conversation tracked, every follow-up scheduled, and a clear weekly picture of whether your pipeline is growing.
Prerequisites:
- A written description of your ideal client profile (ICP): industry, role, company size, and location.
- A CRM or a simple spreadsheet with one row per person and a stage column.
- A daily activity target you can see. Andy tracks messages sent each day.
- An offer that is easy to say yes to as a first step, such as a short call or an invitation to an event.
Why sales prospecting needs a system, not more volume
Buyers have more control than ever, and they punish noise. In a June 2025 Gartner survey of 632 B2B buyers, 73% said they actively avoid suppliers who send irrelevant outreach. More messages to the wrong people make your pipeline worse, not bigger.
Deals also stall without steady contact. Forrester's State of Business Buying 2024 found that 86% of B2B purchases stall during the buying process. A prospecting system is how you stay present through that stall without chasing.
Trust is the other half. In a March 2026 SurveyMonkey and Reddit study of 1,202 U.S. business decision-makers, 73% named peer recommendations as their most trusted source when evaluating vendors.
That is why Andy's routine mixes direct outreach with introductions, comments, and community events. Prospecting is not only asking. It is also showing up where people already trust each other.
The sales prospecting process, step by step
Step 1: Define your list before you send anything
Time: about 60 minutes once, then 10 minutes a week to refine (estimate).
Andy's outreach starts from a written ICP. He gives his AI assistant "a reference of our ICPS" so that new connection requests go to people who match the same demographics. Whether a tool or a person does the searching, the rule is the same: nobody gets added to your list unless they fit the profile.
Write your ICP in one paragraph. Include the roles you sell to, the industries you understand, and the geography you serve. Andy's studio focuses on healthcare, and his community work is centered on Columbus, so both shape who he reaches out to.
Pitfall: a vague ICP. "Small businesses" is not a list. "Marketing directors at mid-size healthcare organizations" is.
Step 2: Set a daily connection cadence you can sustain
Time: 10 to 15 minutes each weekday (estimate).
Andy sends 30 new LinkedIn connection requests every weekday (2:35). "The reason I send 30 a day is because LinkedIn allows for 200 per week," he explains, adding, "I don't want to get too close to that 200 to where we could get flagged." LinkedIn does not publish an exact invitation limit, so treat that number as Andy's working rule, not an official cap.
Andy uses an AI assistant to send his connection requests so he can spend his own time on conversations. Be careful here.
LinkedIn's help page on prohibited software and extensions says it does not permit tools that automate activity on its site. If you follow this cadence, sending the requests yourself is the safe choice. Thirty requests to a well-defined list takes only a few minutes.
Pitfall: sending 150 requests on Monday and none the rest of the week. A steady cadence keeps your account healthy and your inbox manageable.
Step 3: Work active conversations before new ones
Time: 20 to 30 minutes each weekday (estimate).
Once requests are going out, Andy moves straight into LinkedIn messages, replying to people already in conversation. He asks where they are based, follows up on earlier threads, and invites the right people to upcoming events. His own explanation for this order is simple: automating the repetitive part lets him spend his time "actually communicating with people and sending messages and engaging in sales conversations."
This ordering matters. Active conversations are the closest thing to revenue in your pipeline, so they get your best attention first. For a deeper look at how Andy opens and continues these threads, see our guide to LinkedIn outreach and his approach to social selling.
Pitfall: spending your energy on cold lists while warm replies sit unanswered for days.
Step 4: Treat comments as a prospecting channel
Time: 10 minutes after each post (estimate).
Andy had nine comments on a LinkedIn post from the day before, and he worked through them during the session. His observation: there were "ICPS, referral partners potentially in our comment section."
Reply to every comment, and when someone fits your ICP or could refer you, move the conversation forward with a short, low-pressure invitation to connect. Andy's replies were casual and specific, closing with lines like "would love to learn more about you" when there was a real overlap.
Pitfall: treating comments as vanity metrics. People who comment have already raised their hand.
Step 5: Run follow-up across channels, not from memory
Time: 15 minutes each weekday (estimate).
A large share of Andy's session was follow-up. He asked his assistant to find the people who had not responded to an event invitation and draft friendly follow-ups, reviewed the drafts, and sent them. When the replies came in, his reaction was blunt: "That's another attendee right there. That's the magic is in the followup" (21:20).
He also used follow-up to create introductions, drafting an email that introduced two people who he thought would get along. Introductions are prospecting, too. They make you the person who connects others, and people remember that.
The key is that follow-up runs from a system, not from what you happen to remember. Every thread that needs a next step should have one logged. Our guide on how to follow up with leads covers timing and tone in more detail.
Pitfall: sending a single invitation and treating silence as a no. In this session, a follow-up to someone who had not replied turned into another confirmed attendee.
Step 6: Log every action against a daily target
Time: 5 minutes, spread through the session (estimate).
Andy tracks his daily actions in a simple dashboard that shows each day as a block, so he can see at a glance "which days I've been accountable to sending 100 total messages" (3:36). He is honest about it: "Obviously, I don't get there every day. That's the point of this accountability."
During the session, he logged the meeting he had already held that morning, the five DMs he had already sent, and the 30 connection requests once they were done. By the end, he was "almost halfway complete" with outreach for the day.
You do not need custom software. A spreadsheet with a date column and counts for connections, messages, follow-ups, and meetings works. What matters is that you log as you go, not from memory at the end of the day.
Pitfall: tracking only outcomes. Meetings and deals lag. Daily inputs tell you whether the system is running.
Step 7: Move every prospect to a clear stage, including "closed lost"
Time: 5 minutes at the end of each session (estimate).
Near the end of the session, Andy updated his CRM and moved one prospect from contacted to closed lost (34:43) after learning the timing did not work for them. He admitted the rejection stung for a moment, then reframed it: "That's a good thing because you're putting yourself out there."
Closing out a prospect cleanly is part of a healthy pipeline. Use a short set of stages, for example: identified, connected, in conversation, meeting booked, proposal, won, and closed lost. Every person on your list sits in exactly one stage, and you can see at a glance where things are piling up.
When a prospect does reach the meeting stage, our guides on how to qualify leads and running a sales call take it from there.
Pitfall: leaving dead conversations in "in conversation" forever. They hide the real size of your pipeline.
Step 8: Review the numbers once a week
Time: 20 to 30 minutes, once a week (estimate).
Andy closes his sessions with growth stats: subscribers, LinkedIn followers, newsletter signups, and podcast downloads, logged by hand.
Once a week, look at the same kind of picture for your pipeline. How many people entered each stage? Where did conversations stall? Which channels produced meetings?
This is where you adjust. If connection requests are not turning into conversations, tighten your ICP. If conversations are not turning into meetings, change your invitation. If meetings are not turning into proposals, revisit how you qualify.
Sales prospecting checklist
Copy this into your notes or CRM and run it each weekday.
Daily (about 60 to 75 minutes, estimate):
- Open your list and confirm today's targets fit your written ICP.
- Send your connection requests by hand, at a pace you can keep every weekday (Andy's rule is 30).
- Reply to every active conversation before starting new ones.
- Reply to comments on your latest post and invite the right people to connect.
- Send every follow-up that is due today, across LinkedIn, email, and text.
- Make one introduction between two people who should know each other.
- Log connections, messages, follow-ups, and meetings as you go.
- Update each prospect's stage, and close out anyone who is not a fit.
Weekly (about 30 minutes, estimate):
- Count how many prospects entered each stage this week.
- Identify the stage where most conversations stalled.
- Make one change to your ICP, message, or offer based on that stall.
- Invite your strongest relationships to a community event or a coffee.
Mistakes to avoid
- Prospecting without a written ICP. You will send messages that feel random, and buyers will treat them that way.
- Letting tools run your relationships. Use software to remember and organize, not to fake attention. Keep connection requests and messages within LinkedIn's rules.
- Measuring only revenue. Track inputs daily so you can fix the system before revenue drops.
- Following up once. In Andy's session, a new attendee confirmed after a follow-up, not the first invitation.
- Ignoring closed lost. Rejection is information. Log it, learn from it, and move on.
How the Columbus community fits into prospecting
A good share of Andy's session was not selling at all. He was inviting people to a marketing leaders gathering, introducing peers to each other, and checking in on people he looks up to. One of his messages summed it up: "My goal is always just to connect people that I look up to in the space."
That is prospecting in a relationship-driven market like Columbus. When you are the person who brings smart marketers together, opportunities tend to find you. 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.
If you want a system for choosing who belongs on your list in the first place, read about building a Dream 100, and see how Andy applies the Rule of 100 to keep his daily volume consistent.
Start your sales prospecting system this week
Sales prospecting works when it is boring and repeatable: a clear list, a steady daily cadence, follow-up that runs from a system, and an honest weekly review. Start with your written ICP and the daily checklist above, and run it for two weeks before you judge the results.
Then come meet the people who make prospecting easier. See the next Columbus marketing event, or join the Columbus Marketing Organization community on Skool to compare notes with other marketers building their own pipelines.
Obviously, I don't get there every day. That's the point of this accountability.
Frequently asked questions
What is sales prospecting?
Sales prospecting is the ongoing work of finding people who fit your ideal client profile, starting conversations with them, and moving them toward a sales call. For a solo marketer, it means a defined list, a steady daily cadence of outreach, consistent follow-up, and simple tracking so no conversation gets lost.
How many LinkedIn connection requests should I send per day?
Andy Milligan sends 30 each weekday because he works within roughly 200 invitations per week and does not want his account flagged. LinkedIn does not publish an exact limit, so choose a steady number you can sustain, send them yourself rather than through automation tools, and focus on people who fit your ICP.
How much time should a freelancer spend on prospecting?
About an hour each weekday is a realistic starting point, plus a short weekly review. Andy's live session ran roughly 40 minutes of outreach, follow-up, and tracking. The exact time matters less than doing it every weekday and logging what you did so you can see whether the system is working.
What stages should a prospecting pipeline have?
Keep it short: identified, connected, in conversation, meeting booked, proposal, won, and closed lost. Every prospect sits in exactly one stage. Moving people to closed lost when timing or fit is wrong keeps your pipeline honest and shows you where conversations are actually stalling each week.
Where do Columbus marketers find prospects and referrals?
Start with LinkedIn, your post comments, and introductions from people who already trust you. Columbus Marketing Organization, founded by Andy Milligan, is a peer community where marketers, freelancers, and service providers share leads and introductions, and its in-person events are a steady source of new relationships.
Read the video transcript
Kind: captions Language: en What's going on, sexy people? My name is Andy Milligan, and I run a solo marketing business that has generated almost 400K in lifetime revenue over the last year and a half. Um, you guys first time to the channel, this is my daily marketing channel where I take you inside the scenes of my business and how I'm growing, scaling, getting leads, developing my business, and the helpful lessons that you can learn along the way. What I usually do is I package each of these videos around a specific lesson and takeaway that I reveal to you as I'm going throughout my daily lead genen activities in order to help you on your journey. But if it is your first time, I run two businesses, technically three. One is my web and SEO studio for healthcare called MMG Design. The other is the CMO, which is an inerson mastermind events and job board for marketers here locally in Columbus, Ohio, where I live. And the third is my podcast which is one of the top 100 marketing podcasts in our space had on thought leaders like Tas Bober, Andy Cresadina, Anthony Perry, Jay Claus, etc. So if that all that goes way over your head, means nothing to you, just take from this that I'm happy to have you here and I my main goal is to be as valuable as possible with these every single day. So the format we're going to follow here is we're going to do a bit little bit of live lead genen. We're going to build and strategize in public. And then I'm going to do some updates and growth stats, share you over my shoulder while I manually track and log the things that I'm focused on growing like my followers on YouTube, followers on LinkedIn, and obviously pipeline and revenue stats as well. So without further ado, how about we get right into it? My normal little process that I follow here is I'll head into this amazing software called Quad Code and it allows me to take care of some of the outreach parts of my business that I um don't have to do manually. So what I will do is I will log in to LinkedIn via quad code here. Make sure that we do two off. And the cool thing is here is that we've actually gone in and we've given Claude, our friend, a reference of our ICPS so that then it can go out and send connection requests, people that, you know, follow the same demographics, etc. So, this allows me to spend my time actually communicating with people and sending messages and engaging in sales conversations rather than doing pressing a manual button of sending connection requests, which is just amazing because I love being mindful of my own time. So, without further ado, we are going to log in here. get a pretty little SMS message that we will use to sign into LinkedIn with. Boom. Boom. Command C, command V. Submit. And then literally all we have to do now that we're logged in and we're in our our network tab. I will say morning my friend. It is a new day. We need to send 30 new connection requests to our ICP. LinkedIn is open in your native browser. Can you go ahead and start sending? All righty. So, it will begin to send connection requests. And the reason I send 30 a day is because LinkedIn allows for 200 per week. And every weekday, I will send 30. Today is Wednesday, which is a weekday. And I want to make sure that I am not annoying our friend Claude and sending way too many messages to way too many messages. I don't want to get too close to that 200 to where we could get flagged. So, it's going to actually start doing that right now. And that'll allow me to go into actual LinkedIn and start talking to potential customers and engaging on posts. Something that I also do here is if I go to my homebased software that I've built where I manually track and log all of my stuff, uh, if I open up brand stats, go to trailing 30 days, daily actions, this loads like an actual GitHub repo so that I can see which days I've been accountable to sending 100 total messages. Obviously, I don't get there every day. That's the point of this accountability. But I will then open a new tab and link it. I'll have this handy little awareness pop up here in the bottom left where I can manually track everything and all the messages that I send, which is just amazing. So, we have a couple new leads come in for the newsletter. I will make sure that I send those over to my assistant. Uh, shout out to Roa who is very helpful and making sure I don't run myself off of a cliff here in terms of managing way too many things. [sighs] So, those should all be sent. Boom. Roa. Boom. There's one. And another from Kim. Wow. Boom. Here. And then another from I think that's both of them for now. So that's a good start. Go ahead and send this to her. Amazing. Shout out to Lori. I've already had I'm going to track my outreach. I've already done a meeting today and I've already sent at least five DMs. So, I'll go ahead and update that. My system will add you this afternoon. be on the lookout for an uh welcome email and don't don't hesitate to shoot over any particular roles you may be looking for so we can keep our eyes out. Period. Flexing emoji. I do have one new invite to send out for the uh event that we are hosting next Thursday. 8 t-minus 8 days. Ness best textm text. Dang. Boom. Boom. Wanted to follow up on this. If Thursday doesn't work, no worries. Comma happy to get down. It goes down. And the damn it goes down. Damn it. Go down. Goes Thanks for asking. Salute emoji. Starting to get a little bit chilly, but I just got the heating and AC track fix in my new place, so needless to say, I'm set. Haha. feel prepared for once. How long have you been in the seab bus area? I just moved here three months ago. Charisma just quad. How are you doing my friend? Let's check up in on you. 30 new cent. So what I will do is I will head over to my daily actions and I will add 30 LinkedIn connect requests which is just fantastic and gets me well on the road to riches here. Almost halfway complete with our outreach for the day. Amazing. In the meantime, let's still continue on conversations. Lauren, are you based in Columbus? Indeed, you are. Um, shout out [groaning] to Briion. It goes down and the damn go. Great. I got that. I got the song in my head now. All right. Let me before I forget add Jen to the invite for next week. Current J send invite. We now have 2319. Yes. Two may. Uh okay. Okay. I've sent a few recent outreaches for the event that I'm hosting next Thursday. Um, identify the people that haven't responded yet via email and help me draft a follow-up to go ahead and send to them. Be friendly, laidback, and potentially also include a smiley face emoji. Draft them in chat before respond what you with what you will say in chat before sending them [sighs] where you are. Also, there was a good amount of comments on my post yesterday that I should likely respond. Nine comments. It's Look at that. ICPS referral partners potentially in our comment section. Goat emoji. You were literally the person I thought of when the editor made that when the editor sent me the first draft of that edit. Laughing face emoji. Laughing face emoji. Seth, turn off. You look like one cool dude, man. What's up, man? an exclamation point. Appreciate the love on the podcast with Matt. Blue heart emoji flexing emoji. I think we have a good amount in common. Period. Open to connecting sometime. want to chat sometime. Question mark. Would love to learn more about you. [sighs] Where is my [ __ ] problem? All of these sound great. Go ahead and send all of them. That is what? Six new. Oh, come on now. What the hell? Quad stupid head. I love you so much. But this is what I'm kind of referring back to you guys about when you can kind of double the effectiveness and just your overall visibility into what is going on. [sighs] Um, for example, would I have gone in and found those emails regardless, even if I had them tracked within um my CRM? Maybe. But this is just a sure way to make sure we do so. So, six more emails. Four, five, six. Fan freakingastic. Uh, let's go ahead and keep making our way through these messages here. Completely no worries at all. Exclamation point. You're protecting your time, which is just which is important. Period. My goal is always just to connect people that I look up to in the space. Smile face emoji. We are running it back on October 29th if you are interested. Dot dot dot. It's at North Market in Bridge Park and I would obviously love to have you. Period. I So far we have about 25 people confirmed. doing another marketing weers meet up on. Plus, it's been a while and Obviously you and Dennis came to mind right away. It ended up being great and people made a lot of decent connections. and ended up getting a lot of good feedback and I just wanted to have as many marketing folks that I look up to meet one another and come together for a low pressure short gathering that a lot of people can make it to. The last one ended up getting a lot of good feedback. Exclamation point. www.colusmarketing.org/events How about that? Okay, let's go ahead. I want you to take the context of this conversation and use a lot of the same language and respond in chat with an intro that I can draft uh introducing Allison and Laura. Include int text links to their LinkedIn profiles. Also, I just want That was a quick response. Okay. Okay. I can hyperlink both names. Beautiful. [snorts] Beautiful. That's another attendee right there. That's the magic is in the followup, boys. I'm telling you. really looking forward to reconnecting my friend. Period. I'll go ahead and add you to the invite exclamation point. Beautiful. Beautiful. Beautiful. Beautiful. Beautiful. change. Jeez, every time I email Jackie, I get an out of office thing from her. Unfortunate. Um, fantastic. So, we have uh I need to up update the pipeline within folk here. So, Marsh is attended. Marshall's attending 22. Who all do we send invites to on the follow-up thread? I think a few that I think you missed. I think you missed um Bobby Jackson. Um, Ashley Recctor from Quimby Digital. Um, I need to add her as well. Um she's quest one [sighs] point. Do the same draft responses. Bro. Okay. Beautiful, beautiful, beautiful, beautiful [sighs] club in the club. Dude, I always This is just like a constant process of me just having these tracing my daily activities back to like old songs. Laura, you and I chatted on LinkedIn last week. Damn you. I hate I hate how Gmail formats this so that I can't seem to get it in there. I literally have to do this. And an overall incredible person and great at what she does. potential collaborations aside, I think you you both would get along incredibly well. Exclamation point. Hey, I [ __ ] that up. Almost. Laura at cypclub.com. Al almost disastrous. Almost disastrous. That's another email. Check back in on Clotty on number one to actually remove the last line. Starting with either way, no pressure. And then on Bobby, I met the latest message on Bobby's latest thread. Um, I sent the new invite to him this morning. Just recap that thread before getting to it. Yes, you are correct. Bobby J Ocso N. What the hell is wrong with you, Whisper Flow? I said jos and you literally typed the wrong thing. I got another DM there. I do have a couple followup emails to send also here. Check folk also Dara and Eric [sighs] Shadow estate. Hey, I need to respond to Eric Zabrowski. E R I K Z A B O R O S K I. And invite him to our next marketing leaders lunch. I know he responded about a camera, so tell him that he's a legend and ditto buying one and we'll keep him posted. And then also inviting also mentioned that I'm doing another lunch on Thursday with half the pe the people from our core group and half new people with some new agency folks and CMOs from around Columbus and love to have him. Do you have to reply here before texting it to them? I need to reach out to these peeps. Also, I need to respond to John Gimple. J O N G I M P E L making a joke about his last message and inviting him to the lunch. Ask him what he's doing next Thursday. When it comes to Eric's, don't say his name in the beginning. like his previous put a like reaction on his previous message and you spell his name E R I K dumbass. Also, jokingly say at the end, no photos required this time with a laughing face emoji. And then don't put my name at the end either. Beautiful. Two new emails sent. Fantastic. Angel perfection. Beautiful. Beautiful. Send the message to Eric. I just want to let you know that it's not new, bro. I might use you soon, though. Alrighty. Weeds analysis. Beautiful clan made us an artifact. I put in all my interesting. Putting together all of my information from last year and G asked it to give me a revenue analysis. Some of this is client information so I can't show it but that's really cool actually. So yeah cool beans I will make sure that that is hidden before I share anything else there. But that's cool. That'll be a concept of of a future video. Um, what I'm going to do now is I think we've been on we're at like 30 minutes now. That's a good length after I send this last message here to Oh jeez. I didn't know she was eight months pregnantio. Okay. Um, well that's the thing. You This is why like I get you guys see my initial reaction is when I get rejected it's like oh I get like a little annoyed. That's a good thing because you're putting yourself out there saying that to the version of me that needs to hear that. I hope that inspires you as well. So, what I'm going to do is um actually the last message from him was he didn't think he joked that he didn't think a one iron was for him. He goes and I want to jokingly say like, "What do you mean you can't hit a one iron tiger or something like that?" Also, in that message, don't say half the core group, half new faces. just say 25 agency and CMO folk from around the area. And he came to mind right away. All right, let's do some growth stats. While that's sending, I'll go ahead and track that text or DM there. And I'll move him over to al reached [sighs and gasps] contacted to close lost for him. 10 more in the pipeline. That'll get us to our 35 number. And I still have a few past attendees that I need to invite. Need to invite Michelle and Tass. Oh my lord. Okay. Stress. Send it. Beautiful. Yeah, she is a close lost on hers. There are so many other good people I could reach out to. just have not allocated the resources to do so. But check back to the calendar. We are uh I need to add Marsh now. Mars Williams at shout out studio. Send an invite. Beautiful. Amazing. 24 total. Still got to get the final few across the line and then we're going to have a killer second event. Then I will be moving on to getting all of the new attendees. The SOP is next Monday, the week of we'll send an invite email saying, "Hey, looking forward to seeing all of you next this Thursday. It's going to be a great time. Reminder, don't leave. This is your first time attending these. Don't leave beforehand. I have a little I have a little something for you. I meant uh John Gimple on text message. Delete the message to John Gimple on LinkedIn. [ __ ] me. Okay. So, let's do brand stats tracking. Sorry, I'm so hair brain, guys. Um, brand stats, 30-day growth. Let's check YouTube. And they're at 428 subscribers. So, up exactly the same. Uh second channelification second channel we are at 64. [sighs] So exactly the same. Uh LinkedIn we are at AI keeps getting LinkedIn we are at 8025 newsletter. We should have a few more. And I'll also track Spotify for creators here. No. Spotify for creators. Check those. Anatics 262. Do we get some unsubs? No, we didn't. Just one new one. We'll have a few more later today. Analytics on the podcast. New episode with Matt went out yesterday. How did that one do? Um, consumption time a little bit lower. Plays and downloads at 12. So that puts our total to 4596. 96 getting to 5K eventually. But uh, yeah, those are our brand stats I want to dive into. Stay tuned for our next video here. Uh, that's where I'm going to wrap it up. If you are a marketer focused on growing, connecting, and becoming an overall more capable person who's better at what you do, check out the links below. Thank you guys for watching, and I'll see you tomorrow. Adios.