The Intentional Engagement Experiment: Tracking Conversations That Grow Your Business

What happens when you stop letting good conversations get buried in your DMs and actually start paying attention to them?

In this episode, I’m joined by Jayci Trujillo of Happy Girl Marketing to kick off Season 10’s first experiment: intentional engagement. We’re talking about tracking conversations on purpose, not to be salesy or weird, but to understand what’s actually helping your business grow.

We dig into why being strategic about conversations doesn’t cancel out being human, how tracking helps you stop losing connections you genuinely care about, and why relying on memory or the algorithm is a losing game. I also share why this experiment hits one of my biggest avoidance patterns and what I’m hoping to learn by committing to it for 90 days. 

If you want more clarity around where leads, collaborations, and opportunities actually come from, this experiment is for you.

What We Covered:

• What intentional engagement actually looks like in a real business
• Why tracking conversations doesn’t have to feel transactional
• Which conversations are worth tracking, even when they start casually
• How tracking helps you see patterns in leads and opportunities
• What I’m testing in my 90-day intentional engagement experiment

Jayci Trujillo is the founder of Happy Girl Marketing, a boutique social media agency helping business owners reconnect with social media in a way that feels fun, human, and sustainable. 

You can find Jayci at:

Website: happygirlmarketingco.com

Instagram: @happygirlmarketingco

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Transcript

Jacki Hayes

Welcome to season 10 of Here's What I Learned. I'm Jacki Hayes, a systems and ops strategist, romantasy reader, and D&D nerd who's endlessly curious about what makes a business actually work. This season is about experiments.

Big, small, accidental, and transformative. Because every business is built on trial and error, noticing, and iteration. If you're growing a business that changes with you and you're tired of one-size-fits-all advice, you'll feel right at home.

So let's get into it. Welcome back to Here's What I Learned. And this season is going to be so much fun because I have brought in experts to assign me different experiments for my business to run for 30 to 90 days.

And today I have with me Jayci Trujillo of Happy Girl Marketing, which is a social media management agency. And full disclosure, they are my social media managers on Instagram. Jayci, welcome back again to Here's What I Learned.

Jayci Trujillo

Thank you. I'm really excited to be here and to chat through this new season. It's going to be great.

Jacki Hayes

Great. So we of course have had conversations in the background about the experiment that you're going to have me run. So can you tell folks what that experiment is and why you decided that's what I should run?

Jayci Trujillo

Absolutely. The experiment that I have really pinpointed that I think is going to be beneficial to run is really intentional engagement and lead generation through Instagram specifically. It can also be done on other social platforms, but I've written it for Instagram and threads.

And so essentially it is a lot of times we think we're being intentional with our leads. We're following up. Oh, I remember so-and-so.

I need to, yeah, I need to get back to sending them an email or whatever it is, but intentional tracking of conversations, even if it doesn't seem business related in the beginning, intentionally checking in with people who you might want to work with, starting conversations to get to know that person, to see if they might be a really quality lead for you or a business referral, or even somebody you want to have on your podcast or catch up with and get coffee.

Tracking all of these over the course of a 30, 60 or 90 days, I think it can be implemented for a lifetime essentially in your business. And so checking in with those people, posting regular content and keeping track of all these conversations that you're having. And so I've written out different items that I recommend tracking if you're ready to get into that.

Jacki Hayes

Definitely. Let's go dive deep into that.

Jayci Trujillo

Awesome. Okay. So some items that I find helpful to track are their name, their Instagram handle, their email, whatever kind of, wherever you're having these conversations, keeping track, preferably first name, last name.

If you have it, the more information, the better. If you get in there and you had a conversation with Jill and who's Jill, what's their Instagram, what's their business, what's more about them. Next I like to keep track of their status.

And so in my personal tracker, I have new lead. So when you're warming up a friendly conversation, a sales conversation, a follow-up, and then I indicate, okay, have I sent a call link? Was the call booked, not booked?

Have they booked as a client, not a good fit or ghosted? So I think you can really assess these and kind of cater them to your individual process. However, those are the ones that I use.

And then I like to track the lead source. So platform that they have come from. If it's in-person, a cold pitch, virtual networking, in-person networking, all of these different places that leads can come in for your specific ecosystem, tracking that.

Because it's going to be really beneficial to find out, okay, where have the most of my leads and actual conversions come from? Shows you where to spend more time. And then we have notes on the interaction.

And so I like to log the date and a general synopsis of the conversation. You don't have to copy and paste it, but when you're going back to follow up, keeping track, okay, kind of where did we leave off? And then a follow-up date, plan to follow up a couple of days after the initial message if they don't respond, or if it's just kind of like swiping up on their story, okay, if they don't respond, maybe finding another way to interact with them.

And then I like to log objections as well. And so gathering data for future offers, for messaging, why didn't they choose to move forward with me? Was it pricing, timing?

They found somebody else that was maybe better suited for the job. What are the different objections? And then a couple optional things that I think are valuable to track or to add, automations.

And so adding automations in your Airtable tracker, ClickUp tracker, Google Sheet tracker with Zaps, whatever you choose to use, adding automations to ping you when a follow-up date has arrived. This way you're not scrolling through hundreds of leads. You can have a lot all at one time to figure out that follow-up date.

Next, update the notes section when you change statuses. So something that I find helpful is to identify, okay, how many call links have I sent? And sometimes if you only change the status and not the notes section, it can be confusing to remember if you got on a call with that person, if you didn't, kind of what the general overview was.

If you use ClickUp, I love their AI section for this. You can ask the bot, hey, how many leads were in this status during this time period? And it'll let you know.

So those are the things I recommend tracking.

Jacki Hayes

Now, I know that some of my listeners are going to hear this and they're going to have a couple of questions, maybe objections. One would be this idea of interacting with people for the sake of leads or collaborations or things like that, as opposed to just being social, quote unquote, just being social. And I think you and I have both had a conversation about this because neither one of us are wanting to be out there to just be transactional in a gross, icky way.

But we've talked that all relationships are actually transactional in whatever way it happens to be. And also we're business owners. So we are spending our time in our business being strategic about the people we want to reach out to and talk to, whether that's for collaboration or they look like potential leads.

What are your thoughts on that?

Jayci Trujillo

I agree wholeheartedly. I think all relationships are transactional, whether we're cognizant of that. And I think that if you're one listening to this podcast, you are somebody who is in business, who is interested in being better in business, or curious about how others are participating in their businesses.

And so when you are showing up in your business, you come to these roadblocks of it feels icky to sell. It feels icky to have these conversations and to track. Okay, well, that's the equation to sales or to make money.

Or I think by chance, yes, you could probably never post your offer or sell and make a few sales. However, the people in your industry, industry leaders, or people that you look up to, they're selling and they're selling actively and are tracking their conversations. You don't have to do it in an icky way.

It doesn't have to be robotic. Every three days, you like someone's story, you're trying to get them to have a conversation. But it's keeping track of Jackie reads that book, I read that book to that that's immediately connection we have between us, I'm going to swipe up and tell her what I thought or ask her her opinion, different things like that.

And so you're not going out and seeking these conversations like a robot. But it feels very organic. But it's intentional with the opportunity that there's going to be a transaction, whether it's monetary, a friendship, whatever the transaction is.

Jacki Hayes

Yeah, I know that some of my best connections, whether they have been clients, or they've been collaborators, podcasts, guests, etc, has usually started because they posted something on their stories or in their feed that really spoke to me. And a lot of times that wasn't business related. That was they were reading a book that I have on my TBR list, or I have already read and now I want to talk to somebody about it, or they're going to be in my hometown.

And I'm like, Hey, if you need some tips on places to eat, or whatever it happens to be. And I have found that if I don't do a good job of tracking those conversations, they end up clear down at the bottom of the DMS. And I never I'm like, I know I talked to somebody about XYZ book. Who was it?

I don't know. And I don't have the time to scroll through my DMS to figure out who that is. Because as business owners, we need to be strategic about how we spend our time, including about who we're having conversations with.

Jayci Trujillo

Agree 100%. And I think a lot of people want to build an organic, engaged community. That doesn't happen, in my opinion, without intention.

intentionality is really the root of it, in my opinion, because just like you said, if you don't follow up, it's at the bottom of your DNS. And what if they stop posting? What if everyone likes to talk about the algorithm, but if you're not engaging with their content, it's probably not showing up first thing for you.

So you might not see them again, and you might have lost that connection. But if you continue to rekindle that connection and keep it warm, for lack of a better word, anytime something might come up, you think of them, they think of you for whatever reason, podcast guest, they got a new book, they want to share it with you, whatever it is, it doesn't always have to be sales related.

Jacki Hayes

I think you make a good point with the algorithm that we all want to complain about, because Hello, it's not fun. Today, I had something and we're recording this on November 11. And at the top of my feed was something that was posted in October 30, for an event that had already happened.

So it's not always helpful. And if you find somebody that you enjoyed having a conversation with, you're gonna lose them in your feed. And if you want to know what they're doing, what they have going on, the best way to do that is to be in constant conversation with them.

Absolutely.

Jayci Trujillo

So yeah, that's kind of the gist, the overall, I realized I didn't tell you some specifics of the exact experiment. So I want to backtrack if that's okay. But what I've written down is first to log all business conversations.

We talked about that as a general overview. Second, spend time intentionally every single day, engaging with your current audience, as well as new audience members. Now, every day, that can mean something different for everybody.

For me, it's Monday through Friday, and it's 15 to 30 minutes a day. I find that the best. You don't want to be scrolling Sunday afternoon when you're trying to hang out with your family, or five in the morning when you're trying to get to the gym, whatever you're doing.

So pick a time that works best for you and the amount of days. And then posting regular content. I think it's great to engage with people, but put out things that are conversation starters.

And a lot of times, the easiest way to do that is to post regular content. So my recommended, if you're somebody who right now doesn't post at all, would be two posts per week, and then three selling stories per week. Talk about your offer.

Talk about what you're selling. Talk about the value that you add. All of the things that you have going on, talk about them, because people want to hear it.

Jacki Hayes

So when it comes to my experiment, I'm going to be honest. When you suggested this, I was like, yes, because I am horrible at this. One, at starting conversations, and two, at tracking those conversations.

I have gotten better about tracking some things when it comes to the coffee chats that I'm having and the networking events I'm going to, but I have not tracking the conversations I'm having on social media, mostly because I haven't been having too many of them. Because a lot of times they feel inconsequential when I say, hey, I'm reading that book. But in reality, some of those folks I'm now continuing to talk to for two years, with a conversation that started with, I'm reading that book too.

So it makes complete sense that I need to be like following up on those conversations. Because if they read the same book as me, or they had a problem in their business that I could help them with, whatever it happens to be, these are people that I want to engage with on a regular basis. So this is my way of making myself do the thing that I always put off as that's not that important.

When in reality, I know it's one of the most important things for me to do is to have conversations and track these conversations. Because not only do I not lose touch with people, but I'm also figuring out, like you said, is it a specific networking event that is providing me with a lot of great context, or not any context? Is it a certain platform that works better for me than another one?

I'm not going to know that without numbers, without data to look at.

Jayci Trujillo

Absolutely. And something that I'm continuously working towards that now, it's not an exact science, but the goal is to find out your number of conversations that you need to have in order to X, Y, Z, make a sale, get on a podcast, whatever your goal is of this intentional engagement, learning, okay, I need to have a hundred conversations if I want to sell one thing, or if I want to get on one podcast, whatever it is learning that number, because then it comes down to, okay, I want to make this amount of money. I want to be on this amount of podcasts, whatever your goal is. Okay.

I need to have at least this many quality conversations. That number is going to look different for everybody. And it's not exact, right?

You're not going to hit a hundred conversations and boom, the Stripe notification is going to go off, but it gives you a pretty good estimate. And I think that that's really beneficial for people who, one, are limited on time. Business owners who have clients who are running a business are limited on time.

So it shows you where to spend your most time.

Jacki Hayes

Yeah. And I know a lot of us just hate this idea of it's all math, but in reality it is. And as you're talking, I'm thinking this also gives you data about when you're getting better and better about your messaging and about selling your offer because you can start to see the conversion rates go up.

You can see the conversations getting shorter. All of those things are going to be in there and it's going to be like, Oh, wait a minute. I talked to so-and-so and I use these words.

Let me try those words again. Or it's because it worked with that person. Let's just keep trying something along those lines.

Jayci Trujillo

Absolutely. And that's something you put in your tracker, right? You could add tags, you could add different, just tracking items for whatever you might be doing.

A launch, change in your messaging, a sale, all of those different things you can keep tabs on. And then you have a whole bunch of data for, to answer all the questions that you might have moving forward.

Jacki Hayes

Excellent. Well, I am looking forward to kind of, sort of, because it's pushing me out of my comfort zone as all of these experiments are going to do. I'm looking forward to seeing how this goes.

And for everybody listening, I will be doing real-time updates as I'm in this experiment. I'm going to go for 90 days to really see the kind of traction I can get with this experiment. But stay tuned.

You'll be hearing midway experiment updates. And then we'll have Jayci back at the very end, after 90 days, for us to analyze the results that I got. I hope that you join me, everyone, in doing this experiment and seeing what kind of results you get.

But before I let you go, I've got two questions for you. One, what is an experiment that you are going to try in your business? Now, before you answer that, I want everybody to know, not only is Happy Girl Marketing my social media manager, but I work with them as a strategic ops partner.

So I know the inside of your business. So we've had this conversation. So what is an experiment we're going to be working on?

Jayci Trujillo

Yes, we are going to be working on time tracking. Essentially, it is the revenue reality. And so I am going to be tracking every single hour, minute, ideally, that's worked in my business.

If that's client work, admin, meetings, scrolling, tracking these conversations, I'm tracking it all. And then I'm going to categorize it by client or project. So it's all categorized and then record the total monthly revenue and then estimated operating costs to really figure out, okay, this is the formula of my true hourly rate.

And I think it's also going to show where the heck am I spending my CEO time? You know what I mean? Because man, I blink and the day is over.

And so it's going to tell me, am I wasting time? Can I maybe outsource some additional pieces? Where am I hanging out?

Jacki Hayes

I love that you're going to be doing this experiment. It is one that I've done with myself recently. And I was very sad to see what my hourly rate was when I broke it all down.

And I'm looking at not just the time I'm spending with my clients, but the entire amount of time I'm spending in my business, because that's really my hourly rate. And it was also shocking to me to see where my time was being spent and how much of my time was being in certain buckets. And then thinking if I'm putting that much time in that bucket, is there an ROI?

Am I getting something out of that? So it's a great experiment. I can't wait to see what kind of results that you get.

Jayci Trujillo

I'm excited. Thank you.

Jacki Hayes

And where can the listeners find you?

Jayci Trujillo

Ah, listeners can find me on Instagram at happygirlmarketingco. That's where we hang out the most. We're also on threads at happygirlmarketingco.

Jacki Hayes

Definitely go check them out. They've got great content, but also great social media managers. So thank you so much for being here today.

Jayci Trujillo

Absolutely. Thank you for having me.

Jacki Hayes

We'll talk in 90 days. Yes. Thanks again for spending time with me on Here's What I Learned.

If this episode gave you something useful to try, rethink, or explore, the best way to support the show is to follow and lead a review. That helps more curious business owners find their way here. And if you want more real talk about the experiments that shape our businesses, plus practical, doable system ideas, join my email list.

I send one to two emails each week with stories, insights, and strategies that help you build a business that supports your life, not the other way around. You'll also get updates on workshops, new offerings, and the things I'm learning as I experiment alongside you. Until next time, keep experimenting, keep paying attention to what those experiments tell you, and keep building a business that fits you.