They Replied – Now What? Turn LinkedIn Conversations Into Good Meetings

51:39 Wrap Up And Next Event

https://www.linkedin.com/in/jackiegiammara/
jackie@five3consulting.com
five3consulting.com

Transcript:
[00:00:00] Gary Ruplinger: All right. Welcome everybody to today’s session. we’ll be chatting about they replied now what? Turning LinkedIn conversations into good meetings. So, I’m gonna give everybody just about a minute here. I know I’m running a couple minutes late. Had some technical difficulties starting the stream today.

Of course, you know, I was, I was telling, telling Jackie here that, you know, normally we, we hop on 15 minutes early and we were all set. And at 1 53 I jinxed, it was my fault. I jinxed us. because I said, oh, we have like seven minutes, we’re all, we’re good. Sit back, relax, take a break. And then I went to push the button to, to put us live.

And, nothing, nothing. It’s like this has been deleted and we’re just, yeah. So anyway, anyway, I digress.

[00:00:47] Jackie Giammara-Strait: We’re gonna go against some of our own behaviors on this too, because we’re gonna talk about the importance of like being timely with responses to messages and stuff. So don’t do what we’re doing currently,

[00:00:58] Gary Ruplinger: Yes. Don’t be late for Don’t be late for your event. Alright, Carrie, can you take a quick look? Are we, are we actually live? Is it actually gone up this time? Sarah, just want to make sure that we are in good shape if you are. If you are on this, there you are. George, welcome. All right. I guess we are in fact live.

Thanks everybody for coming. So I guess with all that out of the way, it is 2 0 5. So let’s get this thing going. Welcome everybody to today’s session. This is the, they replied now what? Turning LinkedIn conversations into good meetings. And today I have a very special guest with me. Jackie Giammara from Five 3 Consulting.

Jackie, thanks for coming on with me today.

[00:01:49] Jackie Giammara-Strait: Thanks for having me, Gary. I’m a big fan.

[00:01:52] Gary Ruplinger: Yeah, I’m, I’m excited to get to talk to you because. I would say of all the people that we’ve worked with over the years, you tend to be the most successful of actually getting meetings. It seems like anytime I want to talk to you, you’re like, yeah, I’m not sure what I’m gonna fit you in, Gary. I’ve got like six meetings today.

so you’ve been, you, you’ve, you’ve kind of knocked it out of the park in terms of great. You build connections, but I see some people who fall flat with it and, you know, you are not one of those people. You actually turn them in there. I guess before we get into all that though, for anybody who’s not familiar with you or Five 3 Consulting, can you give us a little bit of background about you?

[00:02:34] Jackie Giammara-Strait: Yeah, sure. I’ve spent my career actually close to Gary’s best out in the Detroit area. I worked in automotive for a really long time. Still, still do dabble, in the business in auto. But primarily I’ve worked in the advertising and marketing space. I kind of dub myself as like an end-to-end advertising sales, specialist.

I’m a bit of a generalist, but I love helping smaller companies put their sales plans together, their client service teams, so that they can scale and grow their operations. But I’ve worked on all kinds of. Different projects, micro projects and things like that. And I work with a bunch of specialized partners, so, I often make recommendations for my clients and then I have a partner that can help carry out some of those specific suggestions.

[00:03:26] Gary Ruplinger: Well, very cool. So I think I, let’s, let’s kind of just jump right into it if you’re good with it.

[00:03:31] Jackie Giammara-Strait: yeah.

Thanks for having me. I’m excited to be on one of these. I’m used to going and, and visiting.

[00:03:37] Gary Ruplinger: I know you, you’ve, you’ve been in like the, the fan club in the stands the whole time, so this time we get to this time the spotlight is on you.

[00:03:44] Jackie Giammara-Strait: I love that I’m unleashed.

[00:03:47] Gary Ruplinger: So I know before we get into actually like message and talking to people, you had mentioned that before we do any of that, we want to think about. The LinkedIn profile itself, the person that they’re gonna connect to. I was wondering, can you kind of talk us through, I’ll pull up your profile on the screen so you can kind of talk through it as well.

But, would just love to kind of get your, your take on what makes a good LinkedIn profile and how you can turn into something that actually makes people want to meet with you.

[00:04:16] Jackie Giammara-Strait: Yeah, absolutely. And I want people to know that some of this feedback has come from Gary directly, so you’ll recognize it if you look at his profile too. and some of it’s come from LinkedIn masterclasses and just. Staying abreast of the algorithm on LinkedIn. but I will say in terms of specifically converting messages to meetings, one of the big, returning themes is, my Jackie of all trades moniker that I’ve included in my headline, as well as being a French Bulldog lover. And Gary is like a beer enthusiast and. You know, to be honest, was a little bit different. from what I’m used to, I’m a little more buttoned up or polished. I was out of my comfort zone. But it has started a lot of really great conversations with people. for example, with Jackie of all trades, for the first year of my consulting practice, it was all. Specializing. Everyone’s like, if you’re gonna be successful, specialize. And then I sort of realized my superpower was being more of a generalist and knowing a lot about a lot of different things that involved the, you know, sales and advertising ecosystem. And so I capitalized on that and it led to a huge uptick in meetings for me. Um, and then also people love dogs. They love connecting with you as a human being. So this is true of content that you post on LinkedIn while you’re building yourself as a business authority. People also want to connect with people and, those in my circle know I have three French bulldogs. They run my life.

and I have this business so that they can have a nice life. So I have inserted them on my website and then. Put them on LinkedIn and it resonates with people. People have specifically said, Hey, I’m talking to you. You caught my attention because I have, I love bulldogs, or I’m a dog lover, or I have Frenchies here.

And then we’re exchanging pictures. Um, and then as you scroll down, I have a ton of activities. So just sharing what thought leaders in your space are talking about creating original content. I can actually, if people DM me after this, I can send you, I have a one sheet of a hundred post ideas, but Gary is so right.

You know, you want to push and pull messaging. So the more you give, to LinkedIn in the form of posts and content, the more it gives back to you. It’ll show you the love, but you definitely want to reveal yourself as an authority figure. I can’t tell you how many times people will message me. With lead generation or asking for a meeting, and the first thing I do is go to their page.

If they don’t have a lot of contacts or they’re not in my immediate area, or it’s unclear what they offer or what they do, I almost immediately just decline an invitation. When people are really busy and you’re asking for time, you want them to know that you’re somebody that they can take seriously and that’s not going to waste their time.

[00:07:21] Gary Ruplinger: I think that’s a big one is just, is are, is it worth them taking time outta your day to meet with you? Are you, are you someone they want to meet with?

[00:07:30] Jackie Giammara-Strait: Yeah. Are you gonna let leave them better than you found them? 

You know? 

[00:07:33] Gary Ruplinger: Does your, and does your profile reflect that? because yet they’re, you, you, you know, people say it over and over. Don’t judge a book by its cover.

Guess what? People judge books by their cover and they judge people on LinkedIn, by their LinkedIn profiles.

[00:07:46] Jackie Giammara-Strait: They judge you by what we always called an old school journalism above the fold. So if you’re too busy to really dive into LinkedIn, just pay attention to what you’re putting in your headline. I have a pronunciation key. You’ll see the little audio button because my name’s pretty long and tough to pronounce. and then I also checked, I went through the. Checks screening process to legitimize myself as a person, and I think that’s really important to people.

[00:08:17] Gary Ruplinger: You know, in the, in the, in the space of, you know, AI automation bot stuff is, you know, the, that little check mark there can, can make a big difference. I know, just anecdotally, for me personally, I, I check that when I get invitations from people. I, I, you know, I get an invitation and if first thing I’m looking for, and the first thing I, because I’m trying to disqualify people.

I’ve got almost 30,000 connections and I’m constantly having to drop people. So to get a new person in my network means I’ve,

you know, it’s, it’s basically I gotta drop somebody else. So if I look at yours and it’s like, they are not a, nope, they’re probably not a real person. Gone, 

[00:08:56] Jackie Giammara-Strait: Yeah. 

[00:08:57] Gary Ruplinger: never. They never, they’re never even getting a shot.

[00:08:59] Jackie Giammara-Strait: And I’ll say too, people aren’t afraid to tell me that in a meeting. They’ll say, I am so busy and I get 30 some odd messages on LinkedIn a week, and I don’t listen to any of them, but I took a meeting with you. Um, And so I think that really confirms for us. you know, a lot of it is treat people the way you’d want to be treated, but I also think, you know, when you’re putting yourself in the shoes of your target prospect, if they’re a CEO or a COO, those people are really busy.

So, you know, spend the time on that. Do the easy things to make the hard things easy, you know.

[00:09:36] Gary Ruplinger: Gotcha. So I have a list of questions for you, but I also want to let everybody know if you’re watching, if you’re watching at home or watching from the office today, you can post your questions in the chat and we will, I will, I will read them off to Jackie. We’ll get an answer for you before the, before the end of the session.

So anytime something pops in your head or you want a clarification or you want us to go deeper on something, just post it, post in the comments here and, I’ll make sure, I’ll make sure we ask Jackie about that. Get her take on it. So my first question though is, you know, all these AI tools, like should, should we be using them to message people?

[00:10:16] Jackie Giammara-Strait: We should be using them to do our homework. especially if we’re getting messages back from somebody with a little bit unfamiliar territory, in their background or in their business. We want to be familiar with what they do. Um, but I would say be so, so careful and whatever you do, do not let ai. Interfere direct directly with anything that’s going in and out of your LinkedIn inbox. Just don’t do it. Um, even if you’re really careful, you’re not as careful as you think. And Gary, you and I tested the waters once and we were like, oops, we’ve been caught. So just don’t get, don’t do it. You know, people will send me messages just in simple conversation. Forget to delete the little, you know, this came from AI and it’s like, ah, it’s so sobering, you know? and I think that can be tough for people, especially if you don’t work in communications, and I get that because I’m on the opposite end of the spectrum. But I like to think I’m a good person. So I know that not everyone’s wired the same, but I would say AI Chat, GPT Claude, they offer awesome tools for organizing information, telling you how to position yourself in your messaging, telling you how to do a little follow up, but you want to be authentic and people know when you aren’t because I’ve got, I’ve received that feedback from people too.

You’re an actual person. Thank God, you know, so. Please be an actual person because you know. Especially when you’re a consultant or you’re selling yourself to someone. I have some of my, career search clients on here, and I give them the same advice. You know, you want to pre-sell yourself to people.

They want to know what it’s gonna be like working with you, and you’re kind of duping them. If you use these tools to start the interaction, it’s okay to be yourself. It’s okay to be a little nerdy if you’re a developer, that’s what they’re hiring you to do. So, you know, be yourself. But those tools are cool to organize stuff if you need a, like a roadmap.

[00:12:25] Gary Ruplinger: Yeah, lately I’ve been, I’ve been telling people that before you, you know, try and write a better prompt or go and research, you know, spend another, another evening at home, you know, with, with Claude, Claude code or, or whatever it is that you’re using, is just go outside. Like, actually go, go walk to the bar.

Go, go sit, go sit down and go talk to somebody.

Have a real conversation. Talk, talk to somebody you don’t know that it don’t, don’t go hit on people. That’s not what we’re talking about, but like, just, just go, go chat with somebody.

[00:12:57] Jackie Giammara-Strait: Break the ice. Break

the ice. It’s kind of like dating though, Gary. I mean, we talked about that too. Don’t do things that you wouldn’t do on a first date. You’re just asking for a little time with people here when you’re messaging them. So, you know, I’ve had these people that are like trying to go through the first five dates in one message.

It’s really offputting, you know, don’t assume you already know your prospect’s problems before they’re even talking to you. I get that a lot. Like, please avoid that. But I think, I do think pretending you’re, you’re, you know. You’re picking people up, respectfully is a good way to maybe practice your, your business prospecting.

[00:13:39] Gary Ruplinger: I think it’s, I think it’s be, I think it’s better than just asking AI how to do.

[00:13:44] Jackie Giammara-Strait: I, I do think it’s a good idea to ask, talk to people that are not in your industry because. I think something that’s a key differentiator is meeting people where they’re at. So for me, I reach out to a lot of owners, a lot of business owners, lots of deci key decision makers at the top, but a lot of them are not involved, per se, in advertising.

Sometimes they are. So you kind of want to be able to explain your business to somebody that knows nothing about you, so that you can connect with. Whoever your target prospect is, including if there’s multiple prospects who might play a different role at the organizations you’re working with, you really want to, you know, know who you’re talking to and change the cadence up too for those people.

Otherwise, you’re definitely gonna come off like somebody copying and pasting messages. So.

[00:14:39] Gary Ruplinger: So what, what is your approach if you’ve, you’ve got, you’ve got somebody you’ve connected with on LinkedIn, you’ve messaged them, they’ve responded, and, you know, maybe you’re chatting about French bulldogs or that they think you’re Jackie of all trades is funny. How, how do you pivot and turn that into a, a meeting?

How are you, how are you pitching it? How are you structuring it? I’m, I’m kind of really curious to kind of get the, get the, get the low down on how you, how you would do it.

[00:15:06] Jackie Giammara-Strait: Yeah, it’s different for everybody to be honest. or different for different, engagements. I have a couple different engagements that I’ve got, working, you know, sending outbound messaging. Um, but I would say the biggest theme, and this is going to come up throughout our whole conversation, is you have to start with them. you know, it’s, I’m big on relationship building and I’m big on. You know, knowing everything about the other person, asking them what’s going on. don’t make any assumptions. Do not assume you know what their business pain is. don’t assume that you’re the solution to that. Don’t assume that they’re a customer of yours.

They might enter into your professional life in a different way as a partner, as a referral source, as somebody you can help in a different way. but as a rule of thumb. I usually spend, I, I give myself one time period a night to go through all my messages and I have an important rule for how I do business in everyday life with everyday people. I respond to absolutely everybody that sends me. That takes the time to send me a message or respond to one of my messages, and if it’s a message I sent out to do prospecting, I do my homework. I look at their company website. I try to make some maybe personal connections. Maybe we went to the same university, we’re in the same city.

We can like link up on a couple associations past companies. You can find that out from somebody’s profile. But just know enough about them that you can bring these things up, because then it will naturally gravitate toward a meeting. And another important piece is, at least for me, but this is what, what works for me and what resonates with people. I do not ever. Ask for business. I, you never know how someone’s going to manifest in your professional life, so I don’t assume that they are necessarily even a business prospect. I think doing that can kill deals, so I am just asking for 20 minutes of someone’s time. For a virtual coffee, right? Or like a Zoom meeting, something quick.

And I try to be flexible. Hey, I know it’s really busy closing out the month, but maybe in July as things slow down for the summer, you have some time. Maybe we could catch up and connect on this thing. I noticed you were doing with the business. And, but you don’t even talk about yourself. You, it’s all about them. and truly that. Should be maintained throughout the meeting. You’ll know talking to them. If there’s an opportunity, it will come organically. and if not, you’ll be able to follow up later or send them a reference. I always try to leave people better than I found them, and I don’t sell on LinkedIn ever, ever, ever. But if you are a good person and you’re credentialed and you can expose that in organic conversation by doing your homework and getting back to people quickly and politely, I think that goes really far. I.

[00:18:25] Gary Ruplinger: How do you balance the, the persistence to get a meeting versus coming off without crossing that line into desperation? because I think there’s, there’s a fine line there. I’m just kind of curious how, how you approached that, because Right. Some you may reply to somebody and offer some times, or, you know, offer to meet with them and then crickets.

[00:18:49] Jackie Giammara-Strait: Yeah.

[00:18:50] Gary Ruplinger: how, how do you kind of take that to, to get the meetings you want with people without just constantly badgering and coming off as that desperate person who just, and I just would do anything to meet with you type of, 

[00:19:03] Jackie Giammara-Strait: Sure. Well, I’d say first, you know, you want to set yourself up in such a way that you aren’t desperate, you know, because if in any way you are, that will probably come off to somebody and. So I would say as much as possible, and Gary, you know, I had to work on this, like organizing your own business. I am a solo entrepreneur, a solopreneur, and it took me a while to organize meetings like I was booking a ton of. Stuff, five to eight meetings a day. I had to slow it down. I had to block out a couple days a week to do client work, to collect myself and get it organized. And so I would say if you, and you’ll know if you need to do that, but if you fall into that bucket, you know, keep the. Get the house in order first so that you don’t fall into the desperation trap. but I would also say, and you and I have talked about this too, usually in sales we say time kills deals. If it’s been a week and you don’t hear back, like you’re further from closing a deal. And what’s been really. Thing in the last year is that moniker has just not been true. I mean, I’ve closed deals that I’ve worked a year ago, six months ago.

People will want to take meetings after I kind of felt that they were falling out of favor with the process or they couldn’t make it work or they weren’t interested. And so I do think follow up, methodical follow up is really important. So I would just say keep track of when the last time you’ve reached out to somebody is, don’t follow up. As soon, the longer that it’s been since your last conversation. But definitely don’t consider people, dead leads until they flat out to give you a no. Like, Hey, I’m not interested. And your goal is to get to a yes or a no as fast as possible or diligently as possible. but I would say right now. Nothing’s dead until they, you know, they say so. And to keep track, I use, HubSpot offers a pretty good free CRM tool. It’s pretty simple. monday.com is another good CRM, even Excel, right? Depending on the volume of clients you take to just keep track of key conversations. People that aren’t nos, but they’re not right nows, you know?

And, but like, don’t blow people up. Like if you wouldn’t call. your friend, as often as you feel like you need to call a prospect to follow up, please don’t, please don’t follow up with them right away. You know, wait, give it some time, you know, because these are people too. So when in doubt, you know, do what you would do in a regular professional business engagement, you know, or with your, with your friends, you know?

[00:21:57] Gary Ruplinger: I appreciate you giving some love to, to the, the spreadsheet users out there. as, as one of those people who continues to have multiple spreadsheets around, right? We’ve, we’ve got the CRM, but some things are just so much easier to set up a spreadsheet, say, Nope,

[00:22:12] Jackie Giammara-Strait: Well, and. Honestly, I’ll tell you like I am not a huge fan of note takers. One for confidentiality purposes, but also because I remember stuff and people when I’m writing stuff down. So I’m a pretty active note taker. And with the old school Excel, like there’s nothing plugging into anything. So you have to type the notes, by hand, and then you remember them, you know, and you can organize people better. But if you’re high volume business, you, you might really want a good CRM. And if people need recommendations, that’s something I help my clients with. I’m happy to, to give you beefier suggestions. because that’s where AI can be really cool, and automate things and kind of tell you red, yellow, green, you know, for follow up and stuff.

But, uh, I know a lot of your clients are a little bit smaller in some cases. Like for me, that would just be overkill. You know, I’m pr, I’m. Doing pretty much all the follow up myself, and I’m taking all the meetings, so I want to be a little bit more in control, so

[00:23:20] Gary Ruplinger: Yeah, I’ll, I’ll, I’ll confess. I crossed over to the dark side and, you know, started bringing my note taker to all of my meetings with me.

Um, 

[00:23:28] Jackie Giammara-Strait: for a backup too. 

[00:23:30] Gary Ruplinger: it’s, it’s, it’s, it’s been one of those things where I’ve said, did we. You normally am. I’ll have, I have a notepad. I have it as a backup here, but I found it lets me, it lets me listen a little bit more actively and I can go back to the actual transcript.

And the one I use it, it just, Calendly, it’s nothing. It’s, it’s certainly not a fancy one, but I can ask it questions and say, did we cover pricing or terms or, you know, things like that. Boom. It just, it, it, it answers it. It tells me, here, you answered it. Here’s in the transcript where you did that. It’s like, oh, why haven’t I been using this 

[00:24:05] Jackie Giammara-Strait: Yeah, it’s nice.

Yeah,

[00:24:10] Gary Ruplinger: I have a, we have a question from the audience if you’re ready for 

[00:24:12] Jackie Giammara-Strait: Okay. Yay. 

[00:24:15] Gary Ruplinger: From, Rand Green, Jackie, would you mind walking us through your typical first meeting? What do you talk about? How do you guide the conversation?

[00:24:24] Jackie Giammara-Strait: I am glad they asked. because Gary, we talked about this. How far do we go? Do we get into the meetings? because there are some good tips. so thanks for the question. Rants. would say, again, keeping with the theme of everything being about them, my typical first meeting is I come prepared with lots of questions. And the target focus is the client’s pain points. What’s keeping you up at night? What consistently goes unresolved in your organization? And if you think about fixing or correcting those things. How much time or money would that save the organization? Or how much money could it make the organization?

Like what would that look like? Have them kind of visualize outcomes for stuff that is really tough for them right now. because you’re kind of putting yourself into. Shoes. And you’re also finding out, is this a client I can work with? Can I help them? You know, because you want to figure that out for yourself too.

Don’t take everyone as a client if you really don’t think it’s gonna work. Or there are blind spots, like the polite thing to do is, you know, offer an alternate tool or recommendation. but you’ll find that people have their, every organization has that thing that just won’t go away and. People are not going to, be shy about telling you what that is in detail and explaining all the tentacles and. It will organically guide a conversation. In order to have a good conversation though, you really need to do all your homework. And I would also say be really careful about letting the meeting go on too long, because if your prospect is a high level person or anybody, you know, right? We want to respect people’s time too.

So I like to keep meetings. My first meeting. Under 30 minutes. I usually say about 20, and then prepare to wrap up in case they might have a meeting next. And so just come prepared, make it about them. And at the end of the meeting, one of three things will happen. Either there’s a follow up of some kind.

Let me put a propo, like let’s talk more about this. I think I can help you. Would you be open to seeing a proposal or I can help you, but maybe not right now. And so then you’re gonna keep track of them, uh, in your CRM or your Excel spreadsheet or your napkin, however you like to do your, keeping track of prospects. or they are not a good prospect for you. It’s a no, but leave them better than you found them. So give them some other resource. an important point I want to make is, as much as possible, people are very busy. Do not forget what I’m about to tell you. Book your next meeting while you are on your first meeting. I mean, if you have to put BOLO on the top of your computer in big letters on a post-it note, do it because once you hang up, you’re on the clock. And who knows what kind of problems this person is running into in their organization or, you know, rushing to fix or their next meeting. And I also want to also, I also want to say the follow up is so important. Send a note. It was nice to meet you with a point or two about what you covered. Give them a one sheet for your business. At minimum, leave them with something so that even functionally you’ll show up in their email history somewhere and or if you follow up, they’ll be able to remember who you are.

because they’re probably talking to a million people a day. So just keep that in mind. You want to like help keep your. Prospects organized too. And then they’ll visualize you working with them too, so they’ll appreciate that.

[00:28:15] Gary Ruplinger: Yeah, I think I, I remember learning that one, probably a couple years ago from, from another, another. A client, one, you know as well, Scott Smith there. Excuse me, Scott Moss.

[00:28:25] Jackie Giammara-Strait: God’s our favorite. Scott, if you see this, we love you.

[00:28:29] Gary Ruplinger: because I know he had, he had, told me is that, you know, how, you know, how do you make sure you get the next meeting?

Well, you schedule while you’re talking to him. And what if they just ask for a proposal? You schedule a proposal review. You don’t send the proposal until like 10, 10 or 15 minutes before, so that you know they’ve got it and you can review it with them. But you’re, you’re not just because right? Some people will ask for a proposal as a way of getting you off the phone 

[00:28:55] Jackie Giammara-Strait: And whatever you do, Gary, I feel like we have to say it. You know what I’m gonna say? Do not talk about pricing at all. That is not, the New York is coming out of me a little bit, but. No way at all. That meeting, that first meeting is for them to talk about what’s going on with them and try to help them, even if they ask as much as possible for a first meeting, I would love to set up another call to talk about it, give you some options, and you know, ask if they have a budget, but you need to be. Conscientious too, in doing business, you know, of being polite. you you don’t want to be over or under budget too. You want to, make sure that this is a good alignment. So. Even if they mean well, or you mean well just avoid that at all costs. You really want to gather more information than you, you are going to get in this first meeting based on what we’re talking about and, and my suggestions. So you don’t have enough information. And definitely don’t put pricing in an email. You want to deliver that on your next call, um, because it’ll be the number one reason they can just like dismiss you.

[00:30:09] Gary Ruplinger: No, thank you. Thank you rants for the question. I think you, thanks for breaking the ice, by the way. because now, now I can see we’ve got a bunch of them. So Jackie, you, you ready? You ready for some more?

[00:30:19] Jackie Giammara-Strait: Yeah, let’s go.

[00:30:20] Gary Ruplinger: Alright, this one’s from, Dr. Michelle Pipes. Can you walk us through your funnel on LinkedIn?

[00:30:24] Jackie Giammara-Strait: Sure. so I want to clarify funnel, Gary, we think that’s end to end, like starting with your messaging all the way through to closing a deal. I.

[00:30:37] Gary Ruplinger: maybe just the approach to get the, get the meeting. I feel like once walk us through the approach to kind of, you know, find the people on LinkedIn and get the, to, to get them, get them to the meeting. That’s probably.

[00:30:48] Jackie Giammara-Strait: Yes, totally. and actually this is a good question. Hopefully I’m addressing the, the, the points she would like me to make and if I’m not, send us another note. But, you know, Gary and I talked about this too because I’m a relatively new business owner. So when I began my business, I casted a wide net.

So I would actually say though that the variety of lead gen that Gary and I have done has been sort of my superpower in my business. What I mean by that is, I do media advertising, sales, client service, kind of end-to-end, you know, the whole sales process. I do e-commerce and website and all of that for people. And so. That’s kind of a tall order and different people could prospect be prospected for my business, or in my case, even partners, because I’m so small and I started to realize my clients I was taking on needed some stuff that I needed to get extended help with. So I would say at the beginning of the funnel, Gary and I put together really good messaging. That’s highly targeted that he AB tests, that’s unique that I, we write ourselves, it’s not AI generated and we have it slightly different for different audiences, and him and I run a couple different campaigns. If you did advertising, it would be. very similar where you have, like if we’re talking automotive, Chrysler has a bunch of different brands.

You know, you have the truck brand, you might have Chrysler, Jeep, all the different ad campaigns. We do the same thing for LinkedIn outreach, right? Like I target, you know, PR professionals, small ad agency owners, but then I target like CEOs for startups. But we’re looking at. You know the size of startups.

You want to really think about your business, all aspects, and who you should be growing an audience with, not just who you should be reaching out to, because again, you’re connecting with all these people first on LinkedIn, and then you’re serving them content, right? Because after we start running these. Like these messaging campaigns, I’m trying to create and share content as much as possible. So I show up in people’s feeds after they connect with me. We don’t send messaging until after people have accepted a request. And then the message cadence is what Gary like one message after they accept, and then the second message three days later and then seven days.

[00:33:22] Gary Ruplinger: I believe, I believe yours is said at, after, after somebody connects with you. It’s, it’s one day, three day fi or eight days, if I’m remembering right. 

[00:33:33] Jackie Giammara-Strait: And sometimes we’ll do like a message, Hey, just checking in later, or it’s a new year. Or we’ll have special messaging to just do general outreach. but what I would say is that has been. Quite effective for all different audiences because it’s warm and connected and we’ve been pretty diligent in who we want to build an audience with and serve as well as pull in. I had another thought too. I lost it. Maybe we will, it’ll come back as we talk, but, I would say, yeah, we’ll come back to it if I think of it. Is there anything you can think of, Gary, on that?

[00:34:18] Gary Ruplinger: I mean, I think, you know, that usually, kind of structurally, I’d say from, from yours is that, you know, you don’t, you don’t need, you don’t pitch them right away on the, on, even on the meeting. It’s, it’s really

just, just be friendly and say hello to them, is you, you know? Can be kind of folksy and funny about it or however you want to do it, but even something as, Hey, hello.

Nice to connect with you is better than well. Hi Jackie. It’s nice connecting with you. You do. You fancy a cup of coffee right away. It just, it comes across as crosses a little aggressive. If you 

[00:34:48] Jackie Giammara-Strait: And I would say too, I, I can’t tell you Gary, I wish I had kept track. because I know you keep data on all this stuff and I’m less good. Like I know mentally kind of these themes, but I don’t know the details. But I have booked quite a few meetings on a third message. So usually my sales brain is going, Ugh, this is dead.

Like I’m bothering them, but people are busy and I’ll get those messages too. Hey, I’ve been out of the office, I’ve been crazy. I didn’t go on LinkedIn, but I, but they are still just as engaged as somebody that’s always on LinkedIn and, and connected with you after the first message. So I would say if we’re talking end-to-end funneling of messaging to get meetings. Stick with it because, time isn’t really killing deals or meetings in this case, like I’ve seen, in other contexts, I’ve noticed lots of, especially tech. More people are on LinkedIn and using it as like an alternative even to business email. So, don’t necessarily make assumptions about the, the accuracy or the quality of your outreach based on what’s coming back and when it’s coming back to you because, I’m booking meetings across the board with all different cadences.

[00:36:09] Gary Ruplinger: Perfect. Alright. And then another one here we have from Lauren. Oh, I’m gonna say it wrong, but I’m gonna try. cut.

[00:36:18] Jackie Giammara-Strait: Ano, I know her. She’s famous in Fort Wayne. Baby.

[00:36:22] Gary Ruplinger: Alright,

[00:36:23] Jackie Giammara-Strait: Go Lauren. stay relevant.

[00:36:26] Gary Ruplinger: so then the question is, how do you stay relevant after the meeting without coming across is too salesy.

[00:36:34] Jackie Giammara-Strait: You know, this is a good question. because Lauren, is an excellent copywriter. She’s amazing and also works in media, but she has not been in the sales space. And so, this is a good question because even though I’m in sales, I don’t want everybody to feel like. I, you know, they have to be salesy, right?

Like the best salespeople, in my opinion are consultants, right? They learn about your business and providing solutions. And so the way I stay relevant and put bugs in people’s ears is, is if I connect with somebody that would be good for them to know in their industry or space, or I see an article that reminds me of them, and it, this happens all the time.

Like it’s an ecosystem. If you’re putting content out and. Dedicating yourself to an hour of LinkedIn a day to read, share, and reply to messages. This will come up. You will find things that are useful to the people you’ve had meetings with, and it’s a great way to just pop off a follow up. Hey, I was thinking of you.

I saw this. How are things going? Like, what kinds of stuff are you seeing? And honestly, that’s how I’ve reengaged a lot of people. So it’s a good question. You know, treat them the way you’d treat your friends. If, if you would come off as too much to your friends or like a date, don’t do it. Like we’re not in the business of being creeps, you know, generally speaking.

[00:37:58] Gary Ruplinger: Good deal. And then got one more here. And if that anybody else has more questions as we’re going along here, please feel free to throw them in the chat. we do have a few more minutes yet, but we’ll get this one here for, for you. Jackie. Is, are you seeing, and this one comes from, Shaik. And the question is, are you seeing a higher conversion rate from text to meetings if you switch to drop a quick personalized 32nd voice note in the inbox, or does that sometimes feel too invasive for a cold, warm prospect?

Have you tested voice, voice notes at all?

[00:38:32] Jackie Giammara-Strait: No, I haven’t.

[00:38:34] Gary Ruplinger: Okay.

[00:38:34] Jackie Giammara-Strait: has me outside my comfort zone, Gary.

because there’s, and he might be on this call, but I know a fabulous salesperson here in New York City and he sends me little voice notes in my text and I’m like, dang it, I really need, I tried to send him one back and it just did a voice to text, text message, and I was so annoyed with myself. I’ll be honest though, I get them in my LinkedIn inbox and they do come off as too invasive if it’s like a first outreach. But I think they’re great for ongoing follow-ups and communications. The problem is depending on your prospects, you know, like if, if I were one and you know, they don’t know how to hit the thing, or like oftentimes I’ll, I’ll. Grab the, you know, I’ll rec, I’ll, I’ll hear it or, you know, hit play, but then I forget to reply back or I’m not sure, should I reply in a voice message or a text? You know? Message of some kind. So that’s, um, for our next meeting, after we do some market research and get back to you on the voice to message. but I would say, you know, I started my career as a professional broadcaster And so that’s something we should deep dive into. because I was gonna say too, like. With LinkedIn, please have a headshot. Please have a professional picture. We can all look good, you know, we can all look professional. but I think that goes really far and I do think if you have an executive presence and we all have it, if we put some work into it and we, you, you know, it’s so inexpensive now to get really nice quality microphones and lighting and all of that for at home, for your home office. I definitely think it is worth it to do like a video message. I don’t know if it would be my first outreach, just because it’s really hard to know what to say because you want to be pretty. You want it to be organic, you want it to be customized and you just don’t know enough about your prospect when you’re trying to get the first meeting. So that would be my feedback. But I do love it. I love it. I think the closer you can get to in-person, awesome. Like, I don’t know Gary if I told you this, but I take people, anybody in New York, I’m like, want to go for a real coffee, want to go to lunch? And I get huge kudos because everyone’s like, nobody’s taking anyone to lunch.

I am a little old school and that’s how I learned to do business and it works. So, because nobody else is doing that. So, I’m a fan, I am a fan of the medium. Having like a recorded message or a video message or in person. I just think the timing, it might be. Beyond your first getting to know you unless you did that, like as a coffee, but when you’re asking for it, probably just good to leave it as a back and forth.

[00:41:30] Gary Ruplinger: Yeah, I’ll, I can add a little bit to the, the video message side. We, we’ve actually never tested the voice notes because nobody, nobody’s ever asked about them. and personally, like, just, just me personally, no data to support this whatsoever. I don’t like them, I don’t want them, this, this, this is very much at, this could have been an email and I could have read it silently.

I had somebody. I was on, on a trip, last week. my wife and I were out in Minnesota, you know, nice, you know, on the river. And somebody popped in my notification, said they sent you a voice note that that didn’t get read all listened to all weekend. because I just wasn’t at a place to, to listen to it.

whereas if I had seen the message, I could have replied back to him right away, but I didn’t know what it said. 

[00:42:15] Jackie Giammara-Strait: Same Now? 

[00:42:16] Gary Ruplinger: communication standpoint, it was like, it made it, I had to put a lot more deliberate effort into it, but I remember 

[00:42:22] Jackie Giammara-Strait: Yes. Now I will say, because this goes into other advice I give people with regard to selling and client service, more importantly, when you’re building a long-term relationship, and that’s really what we’re doing here, is building a relationship. You do want to meet people where they are, and that includes their mode of communication.

So if a prospect is sending you a video note out in response to one of your messages, and that has happened before and now that I’m recalling this, you should send them one back. because you’re gonna start working with people. Some people like text, some people like voice to text, some people like phone calls, some people. Like e Yes. And it’s your job to like know your, your people and like, you know, meet them where they’re at, you know? And to me that’s like a professional thing that’s like being a good, uh, business person. And I think it’s become challenging, you know? Like I, I don’t even know if I could use a Snapchat right now.

I haven’t opened it in like a decade, you

[00:43:30] Gary Ruplinger: Are they still 

[00:43:30] Jackie Giammara-Strait: that a thing? Yeah. Like. Is that what, I don’t know what like the young people are doing, but I, I tell people that too. Like you, you know, try to kind of learn what people in your industry or target market are doing and try to match that. because you really do want to make it easy for them to communicate with you so.

[00:43:52] Gary Ruplinger: Gotcha. And then a follow up here from, from rants. So, Jackie, in your first response to someone who has accepted your invite, will you often ask a targeted question about them or their business to get the conversation going? Or do you keep it simple and thank them for the connection, then follow up with them.

[00:44:13] Jackie Giammara-Strait: actually, so Rands, thanks so much for this question, and as per. The direction I received from my Sagely lead here on this call, Gary, I don’t do anything until my first message after they accept, and that’s part of our messaging cadence. I don’t do anything before that.

[00:44:35] Gary Ruplinger: Yeah. So basically, yeah,

keep it, keep it, keep it simple. Thank them for the connection. The next message is can do a little bit more of the lifting, but 

[00:44:44] Jackie Giammara-Strait: I’ve started to feel like now when people do that, that they are gonna sell me and it makes me, you know, the blood pressure just goes up a little. So I would just refrain. I don’t feel like it was always that way, but I’m just speaking as a user and as somebody that also is prospected by other people and who deeply respects the process.

You know, I respect everybody that reaches out, but. It’s like, yep, if I accept you and then I get a message, or you’re sending me a message inside of a connection request and it’s not for something specific, like, I want to be an intern for your business, or, I saw that you had a job posting, or, I saw that you worked at this company and they had a job opening, and it’s, but that to me is unrelated to prospecting. That is like the only time I think it’s appropriate for people to send and receive messages before. Somebody accepts them on LinkedIn as a connection.

[00:45:45] Gary Ruplinger: Very good. I think that really kind of hits most of the questions I have. I know we’re kind of getting close to time. Is there anything, Jackie, is there anything I haven’t asked you yet that I should have?

[00:46:01] Jackie Giammara-Strait: I think we went through everything. Should we, oh, did we talk about, Don’t book a me don’t send your Calendly booking meeting, booking link out in any of these correspondences, right? Like you, I feel like this is your reminder from Gary Ruplinger not to use your link. because you bring it up on every call, but it serves to be. brought up. Again, it’s great to have that. You should have that to build authority and you should make it impossible for someone to find you and have a booking link and all your emails have a signature with all the ways to reach you. That’s very important. However, it’s. Kind of rude to ask for a meeting and not even do the effort of, the minimum effort of asking when a good time for them to meet is and then sending them a meeting invite.

Right? 

[00:46:56] Gary Ruplinger: I I, think you’ll find that even for people that, that logically pragmatically, they understand that this is the easiest way to get the meeting booked. Is it just, it just feels a little. Disrespectful and that you aren’t important enough for them to even bother to even bother looking at their calendar.

Now that flips totally on its head. If you are the one doing outreach and they reply back with, Hey, here’s my calendar. Like, find some time for us, you, as you as the person trying to initiate that, you jump on that, you get that meeting book, but if, 

[00:47:31] Jackie Giammara-Strait: Or if they ask you Hey, do you have a booking link? You definitely want to have it. So you’re prepared if they do ask

you, but never ever volunteer it. Yeah. 

[00:47:41] Gary Ruplinger: Like, yeah, ask for that. Ask for there.

[00:47:45] Jackie Giammara-Strait: Yes.

[00:47:46] Gary Ruplinger: If you’re like, oh, we can’t find a time, Hey, do you have a calendar link? Way better that that’s gonna get that meeting booked. You know, five times better than you sending their, Hey, it looks like we haven’t been able to connect. Here’s my calendar link. That is your throwaway.

You’re never talking to that person again. Message. That was it. That was your, that. If that was your Hail Mary, it, the ball was dropped.

[00:48:07] Jackie Giammara-Strait: Yep.

[00:48:09] Gary Ruplinger: game over.

[00:48:11] Jackie Giammara-Strait: yep.

[00:48:12] Gary Ruplinger: no, I think that’s a good, that’s a good one to end on is don’t send calendar links, please.

[00:48:18] Jackie Giammara-Strait: That’s how you should sign off all your meetings.

[00:48:22] Gary Ruplinger: Okay.

[00:48:22] Jackie Giammara-Strait: But the other thing I want to say is don’t be nervous. I feel like people who don’t work in sales don’t understand that the people who are really good at it, even better than me, you know who you are. Biz dev people that I love and hire. because I don’t do this like you guys do, but be okay hearing no like no’s refreshing too, because it’s gonna get you closer to your yeses and most people are pretty cool.

And if you are polite and put that out. To people, it will come back to you like most people are awesome. So just keep that in mind, like don’t be afraid. Be yourself. Like it’s very hard to screw this up, and even if you do, everything can be fixed. So just sort of keep that in mind when you do all of this.

And don’t take no from someone who can’t tell you yes either. Like if people decline a meeting but they’re not maybe a primary decision maker, I would reach out to somebody else connected to them who may. Be able to. but I would say like, don’t overthink it. Don’t overthink it. I think people are just so afraid of things that never even happen and then they don’t, um, do lead gen to its full potential.

Like, I’m not even the best, but I give it a hundred percent effort. And then I’ve been getting, you know, decent results. And PLE people are very respectful and I try to show that too. Because there’s a lot going on out in LinkedIn world as we know Gary a lot

[00:49:50] Gary Ruplinger: Absolutely.

[00:49:50] Jackie Giammara-Strait: on.

[00:49:51] Gary Ruplinger: If somebody’s, looking to get in touch with you needs some help, what’s the best way for them to do so?

[00:49:58] Jackie Giammara-Strait: they can send me a message on LinkedIn. They can email me jackie@five3consulting.com. and then our website is five3consulting.com. there’s a variety. Call Gary. message Gary, or any of our common contacts, I’m impossible to not get ahold of. You know, come find me on the Upper East side of New York.

I’m the woman on the street with the dog, uh, the little French bulldog. I mean, I’ve talked to some designers out here who are trying to market their products. You know, business happens everywhere. It’s kind of fun. So, you know, and even if you have a question or need a resource, you know, please don’t hesitate to reach out.

I have an awesome network of amazing partners and people, and Gary is one, I can’t say enough great things about him. He single-handedly helped me, like, help my business go and helped me get off my, Get my feet off the ground. And, and I’ve met some incredible, incredible people, business partners, clients, because of the good work that he has done for me.

So, I, I do want to leave everybody with that too. There are so many solutions out there. he does such a good job and follows a method that I’ve always used that’s tried and true in business for decades. So.

[00:51:23] Gary Ruplinger: Thank you Jackie. I appreciate that.

[00:51:25] Jackie Giammara-Strait: Of course, and I really mean it, Gary, I don’t go on these with too many people. I’m just kidding. I’m not that popular. I, I’m very privileged that you would invite me to this, but.

[00:51:39] Gary Ruplinger: Good deal. I think we’ve answered all the questions. Thanks so much for everybody for coming on today. really appreciate it. And, we’ll be, we’ll be back here at the end of, end of July with another, another event I think. I don’t think we’ve actually locked down the topic yet, but hopefully, look for an invite in your notifications and we’ll see you then.

Jackie, thanks so much for 

[00:51:58] Jackie Giammara-Strait: Thanks Thanks so much