Developing Thought Leadership Using Roundtables and Workshops

Jessica Lackey stands on a wooded path wearing a black top, black leather jacket, and red skirt. Green trees line the path in the background.

We’re a few episodes into this mini-series on thought leadership, which means its just about time to address the fact that a person isn’t born with thought leadership or a particular sense of expertise on one niche topic.

It’s actually quite far from that: Thought leadership is created, developed, recreated, curated, potentially recreated again, and then built upon over time.

And one way to develop your thought leadership and strengthen it over time is to offer workshops and roundtables to an interested audience. When you’re in front of a live audience, you’ll be better able to determine what hits, what falters, and then make changes to adjust and improve your thought leadership in ways you can’t do with other mediums.

Today, I’m joined by Jessica Lackey, and we’re going to talk all about using roundtables and workshops as a form of developing thought leadership and providing value to your audience.

Copy says: Listen in to this episode of the Talk Copy to Me podcast

Here is what Jessica and Erin want you to know about developing thought leadership

  • How roundtables allow you to test ideas and grow your thoughts on a subject over time
  • Why testing different presentation types and methods is important
  • What to do when you feel as if you have nothing to share and no thought leadership of your own
  • The role curiousity plays in thought leaderhsip
  • The virality versus depth concept
  • Why Jessica doesn’t charge for her monthly roundtables and workshops
  • Whether there’s a possibility that you may “give too much away” as you’re developing thought leadership
  • How to determine the direction your thought leadership will develop into the future

Other podcast episodes and resources mentioned in this episodes:

Podcast Marketing Trends Explained, a podcast by Jeremy Enns and Justin Jackson
Check it out on Apple, Spotify, or on YouTube if you prefer video to audio

Want some action items from my interview with Jessica Lackey?

If developing thought leadership is important to you, here are some of the things you can do now to strengthen your thought leadership presently and for the future, as well.

  1. Develop the next roundtable topic based on client needs and gaps in your existing content
  2. Continue researching positioning and thought leadership development from industry experts
  3. Use the roundtables and workshops as source material for your other forms of content, such as writing a book, developing courses, and any other forms of content marketing.
quotes from this episode of the Talk Copy to Me copywriting podcast

Quotes about using roundtables and workshops to develop your thought leadership from Jessica and Erin

  • “It gives you the opportunity to try out your thought leadership and learn yourself what your audience needs, what they appreciate, and how to develop your thoughts further and use your curiosity to create other forms of thought leadership.” – Erin Ollila

  • “So in the conversation, I’m teaching for about 30 minutes answering questions. And then every question I’m like, oh, this didn’t land. Or, like, I wasn’t clear here.” – Jessica Lackey

  •  “Forcing myself in the best possible way to put things down on slides — that’s that’s how my brain works. I think in frameworks. That’s really valuable for me.” – Jessica Lackey

  • “Thought leadership comes when I get really curious about a specific subject.” – Jessica Lackey

  • “So I’m only benefiting myself if in a selfish way by presenting all of the information that I have because the people who will not work with me will be better served to serve themselves, and the people who want to work with me will feel so much more confident about that decision.” – Erin Ollila

  • “There are fewer people that are potentially interested when you deepen your thought leadership, when you go beyond the surface level, when you go and you start to niche, quote, unquote, because you start going down the arcs of curiosity that really are gonna hone your thought leadership.” – Jessica Lackey

Meet this episodes guest expert on Talk Coy to Me

Jessica Lackey is a strategy and operations advisor who blends business strategy, practical application, and a human-centric approach to create sustainable businesses. With a background in corporate leadership, McKinsey & Company consulting, and a Harvard Business degree, Jessica knows a thing or two about hustle culture and what it feels like to judge success by the bottom line…at all costs.

Now, she combines her deep experience in consulting, Fortune 500 operations leadership, and coaching to help businesses grow without sacrificing the well-being of their clients, team, and community.

Check out Jessica’s website and then connect with her on Instagram and LinkedIn.

Take her free Radical and Rooted Business Lifecycle Assessment, and learn about her services here.

Get to Know the Host of the Talk Copy to Me Podcast Erin Ollila

Learn more about your host, Erin Ollila

Erin Ollila believes in the power of words and how a message can inform – and even transform – its intended audience. She graduated from Fairfield University with an M.F.A. in Creative Writing, and went on to co-found Spry, an award-winning online literary journal.

When Erin’s not helping her clients understand their website data or improve their website copy, you can catch her hosting the Talk Copy to Me podcast and guesting on shows such as Profit is a Choice, The Driven Woman Entrepreneur, Go Pitch Yourself, and Counsel Cast.

Stay in touch with Erin Ollila, SEO website copywriter:

Here’s the transcript for episode 123 on developing thought leadership with guest expert Jessica Lackey

NOTE: This podcast was transcribed by an AI tool. Please forgive any typos or errors. Episode 123 Jessica Lackey Thought Leadership Roundtables Erin Ollila: [00:00:00] Hello, Jessica, I’m so happy to finally have you on the podcast. I love hearing you on other people’s podcasts and I’ve always thought you’ve had such intelligent things to say. Erin Ollila: So I’m happy to finally have you on my show. Welcome. Jessica Lackey: Thank you. And I’m hoping I can say more intelligent things on this podcast. Erin Ollila: Oh, I have every belief that you will. No pressure. No pressure. Let’s start off by talking about what your definition of thought leadership is. Jessica Lackey: My definition of thought leadership is having a defensible point of view about the world and people in that direction. So I’m very much in the West Cal school of thinking of having a spiky point of view. And, , Defending that point of view, learning about it, crafting, , content around that to really, , galvanize people to a better future. Erin Ollila: I love how you describe that. And I think it’s so interesting that, like, you mentioned, [00:01:00] like, it’s developing the thought leadership because a few of the episodes that we’ve had already, we’ve kind of just jumped into having thought leadership and then taking that thought leadership that has been developed and producing it into something, like a speech, like a book or things like that. Erin Ollila: But I think one thing that’s kind of been neglected in these episodes was to talk about the idea that thought leadership does need developing. , you’re not inherently born with a thought that is, wildly intelligent and also wildly popular, right? And now you know how to,, share that thought. Erin Ollila: That is the farthest, I think, from the truth. I think thought leadership takes practice, and I think thought leadership takes, , Questioning of Your Own Thoughts. So, I’m excited to talk about that today in the larger picture of how you take the monthly roundtables and classes that you offer to your audience as a way to develop your thought leadership and also repurpose it as part [00:02:00] of your content. Erin Ollila: , when did you start doing The Roundtables and the Monthly Classes. Jessica Lackey: So I started doing what I call monthly planning sessions. I realized that for a lot of my clients, , we’re swimming in a sea of shiny sheds and trying to move 15 balls up the hill at once and we’re moving none of them and so I said, needs to be a space and time for people to come together and plan what the next project is that they’re going to work on, , working on. Jessica Lackey: I was in a productivity phase at the time, but those started morphing to, well, now I get together with people on a regular monthly basis is this all started around two and a half years ago. , but I have things I want to say. I want to have. And I have an audience, a small, very small audience at the time, who was like, Jessica, you consume so much content and you’re thinking so much. Can you like talk on this? And so I started, , officially [00:03:00] 2020 or two years ago, 2022, a monthly dialogue. Essentially, I was coming up with a monthly teaching topic. Sometimes it would be teaching. Sometimes it’d be just more question and answer. Sometimes it’d be guest speaker, but a monthly. conversation round table about something that I was learning about myself. Erin Ollila: Yeah, so , not only were you motivated by the people within that audience that you have, but you’re taking their feedback and then developing it for something like what I think is key that you said, that you were learning yourself. So this isn’t necessarily something that, you know, you had studied for an extensive period of time and that you’re then just disseminating to people. Erin Ollila: This, While you may have some obvious, like, history or education or experience in some of these topics, these are things that you’re kind of diving into personally. How, how was that process for you? Because I would say most people tend to err on the side of thought leadership with their, within their own, like, built up experience Jessica Lackey: well, I [00:04:00] think I, I’m usually teaching things that I’m learning about, but I have some foundational background in, Erin Ollila: Mm hmm. Jessica Lackey: doing is thinking about all of my background can serve the audience, but also what am I missing in, um, so I, I did a two part and ended up being two parts. series on the systems of sales and marketing. everyone talks about, you know, social media is marketing. I’m like, well, sure, but not really. And I was, for myself, I was interested on, in getting off of the, the social media content hamster wheel. And so I started, , I started for myself, I started thinking about this topic in like September of 2023. And I was like, well, why, why don’t I see a whole lot more about B2B sales process? I see marketing as like a broadcast neutral list. , I’m like, well, well, I don’t, that’s not how I get my clients. I do other things. And then I started reading everything I could get my hands on for my own [00:05:00] business, but also for my client’s business being like, I don’t see us talking about this thing. Jessica Lackey: I don’t see a lot of people talking about this. I don’t see talking about X, Y, and Z. So I think I read like 15 different books on the systems of marketing and sales and the structures behind it and I framed it to my audience I’m like you’re you’re getting this like I’m Basically forcing myself to distill all the things I’m learning about and reading into something That’s that’s useful for my audience. Jessica Lackey: But even since I presented it in January and we’re now talking April I’ve changed the wording I’ve like so they all got a rough draft but I’m like that rough draft was honed by some detailed study over the previous six months and like detailed working in my business for the prior couple of years. So I’m kind of framing it as like, this is like hot off the presses. Jessica Lackey: This is my initial thinking on things. And my audience loves it. They’re like, there’s no way we could do all this work to like distill things and read all the books and listen to all the podcasts. So can you just tell us what you’re finding? Erin Ollila: Yeah, and their feedback helps you [00:06:00] develop your own thoughts on the process, which I promise I’m going to get to for a second, but I think maybe let’s back up for a second to talk about what the actual, like, experience is like for someone who attends one of these events, you know? Are you teaching and then there’s questions? Erin Ollila: Like, how, how does it work if someone shows up? What, what would they expect to gain? Well, not to gain, what would they expect from the experience? Jessica Lackey: Yeah, so there is a component. So for 30 minutes, unless I’m verbose, which happens. , so I’m teaching a framework or a point of view for roughly 30 to 45 minutes. Asking questions to, , generate dialogue, but what’s interesting about this is because I have a lot of people that come back on a regular basis who have maybe never worked with me before, but I know enough about their business to start making connections and thinking about how, if I was in, , this, this person’s shoes, how might I, you know, Apply this. Jessica Lackey: And so I’m actually on the spot thinking about, not just for my own clients, [00:07:00] but anyone who I have some like passing knowledge of their business with how this might be applicable in their situation. So in the conversation, I’m teaching for about 30 minutes, answering questions. And then every question I’m like, Oh, this didn’t land. Or like, I wasn’t clear here. Oh, this needs its own 30 minute conversation. Those are all helpful for me to both demonstrate what I’m, I’m learning, provide value, but also. of get paid an attention to develop my own ideas. And I’m like, Oh, this is, that’s the next, next one of these I need to do, which is going deeper on this particular topic or clarify my thinking here. Erin Ollila: Yeah, and I, I think that is such a valuable thing for you as a business owner. If anyone’s listening to this and they’re considering the idea of like doing their own regular event where they are able to develop their thought leadership, know that this is probably one of the biggest takeaways that you can have is that opportunity to have that live audience who can, , you know, you focused on the things that you could develop better. Erin Ollila: But also, you [00:08:00] can see what does hit, right? So if you are then taking, , all the cultivation of everything you’ve kind of put together and the experience of how people received it, developing that further into something like a talk, like TED Talk or a keynote speech, then you are, you’re gonna know, okay, you know, this was something I can go a little bit harder on because it was really well received. Erin Ollila: Specifically, like you’re saying, you know, they get the benefit of seeing themselves potentially within the examples when you know their businesses and you can You can develop the examples using, , their own needs, but then you’re able to also kind of learn more about your audience based on that, right? Erin Ollila: So it is a very co beneficial thing for the audience and for,, the person who is leading the round tables. And I think that it gives you a chance. I mean, just from hearing how you’ve kind of described it to determine your own level of interest and how much you want to go forward. with whatever it is you’re teaching about, Erin Ollila: because I’m sure that, you know, in the two years that you’ve been doing this, [00:09:00] you probably have had some topics that you did some decent research on, thought you have had a lot of interest in, and then just found maybe either after teaching it or how it was received that it wasn’t something you wanted to pursue. Erin Ollila: Would that be right? Jessica Lackey: Yes. And no, I think what I’ve discovered is that there’s like levels Jessica Lackey: Hmm. That’s , usually I find I do , a one on one type topic. , I’ll give you an example of like, Task Management, Time Management. I would say that my initial teaching on the topic was, I don’t want to say a rehash and a regurgitation, it’s all cited and it’s all quoted, but it’s kind of a, I’m teaching what I have learned from others, right? Jessica Lackey: So like there’s the curation. I’m still going to package it in a way that makes sense for my audience. But then the next time I teach on that similar topic, it’s,, , what was missing from. the information I curated from others that I have been thinking about since the last time I taught the series. Jessica Lackey: And that can tend to be like the 201 level of conversation where, , some topics get a 101 and [00:10:00] I don’t move on because I’m like, oh, there’s not much meat on the bones, but, , the 201 topic. And then there’s a 301 topic. And then of course, what you find is that there’s the course material, the template that goes along with the 201 material, but I’m only knowing that because I’m like of teaching. this topic, and then I get more interested in learning more about it. And then I teach the detailed version. And then I teach, then I come up with the template and all the questions come after teaching it a couple of times, going deeper on the topic. Jessica Lackey: . And it really depends on kind of, again, what type of thought leader you’re trying to cultivate. , for me, myself in like the best possible way to put things down on slides. Erin Ollila: Mm Jessica Lackey: That’s how my brain works. I think in frameworks, , that’s really valuable for me. And it also informs the next project, which is, , my YouTube channel. Erin Ollila: hmm. Jessica Lackey: I’ve discovered that I write, but I also, this process to discover that like my work is relatively visual. Jessica Lackey: Like, it’s really hard in a podcast format, I think, to say, well, we have three different topics and three [00:11:00] subtopics, Erin Ollila: Mm hmm. Mm hmm. Jessica Lackey: slides or on a, on a visual medium. So, um, I don’t know what my podcast is going to be, but I certainly know that on, that my work requires visuals, which has informed, now my thought leadership has to have visuals Erin Ollila: Sure. Jessica Lackey: an illustrator and things like that. and it’s a circular process by thinking through the frameworks that are going to go on the slide then forces me to like come up with the visual framework and when the visual framework isn’t holding together then I have to go back to my slides Erin Ollila: Yeah. Jessica Lackey: it really informs the body of where my thoughts show up Erin Ollila: Mm hmm. Jessica Lackey: which mediums I go for and which mediums I don’t go forward in. Erin Ollila: . Oh, I think that’s, that’s such a good point, cause that, a lot of that. It skates up on the developing, ? So, you’re mentioning the idea that, like, you can find gaps in different periods, right? Like, if you’re, , In the process of brainstorming, or, , I think what you were suggesting when you talked about writing initially was that when you write, you sit down, you [00:12:00] kind of get everything else at once, but now that you’ve introduced this visual element, your brain is also working differently to kind of find gaps and, and, and go further into things, and I find that that has brought As I’ve matured, as I’ve gotten older or grown in my business, that’s something I had to adjust to, maybe? Erin Ollila: Like, as a writer, someone who has multiple degrees in writing, I’ve just been so used to outlining and then just getting everything down on paper. But I don’t actually think that that is the best process for me. And it reminded me of when I did all my student teaching, that that wasn’t actually what I did for student teaching at all. Erin Ollila: If anything, for student teaching it was more gathering outside, not sources, but , Materials, where I could bring them into the classroom, and then in the process of the materials I collected, I was then able to like, build the connections, right? And then get the lesson out based on the outside things I was bringing in. Erin Ollila: So, I [00:13:00] find with my own thought leadership, as I’m growing, and I’m gonna jump sideways for one quick second. Thank you, ADHD. , having children really threw my confidence in my thought leadership quite in a spiral because I had, I didn’t have child care, purposefully, chosen didn’t have child care while I was running a business and, , It basically truly 100% meant that for about 20 hours out of the day, I was 100% on and required to perform at my best, whether it was with my kids or at work. Erin Ollila: And I think that in taking care of my children myself, which I was very grateful to do, I only had this tiny percentage left of intelligence to serve my clients as a service provider. Not to develop my thought leadership. So was I intelligent? Was I able to perform? Yes, but I was constantly, and this is pre podcast, I was constantly thinking like, I don’t have anything to say anymore. Erin Ollila: And it [00:14:00] was a little existential crisis of sorts, because I am someone who enjoyed teaching. I am someone who really just. Loves to read about things and learn new things and have conversations. And suddenly it felt like I just didn’t have the ability to do that. So, you know, friends, if you happen to be in those shoes right now, your children get older, it gets a little easier. Erin Ollila: I will say that. I, but I, I mentioned it cause I think it’s a vital point of me. Knowing whether I could step up into a thought leadership place, right? Like, do I have these capabilities or am I at my max right now? And I think that what I found, to bring it back to your original point, was When I approached my own thinking in a very different way, not just sitting down and trying to type into the computer, but from A, I’m going to stand on a stage and talk to people. Erin Ollila: I am going to go lead, um, workshops within a business for like small groups. When I approached it in a very different way, that’s when I was actually able [00:15:00] to Create and cultivate my own thought leadership. So it wasn’t just taking the things I’ve learned and like Processing them and sharing them. It was having my own opinions on them You like, you know the spiky thoughts like you say at the beginning so I think that if anyone’s struggling like if they’re at that point where they’re like What do I have to say? Erin Ollila: Maybe just take it from a completely different approach and, build some slides, right? , maybe have, like, an infographic, do videos, do speaking, and, and you’ll see that it does adjust. And the repetition and practice, I think, really makes it a lot easier to, , approach into now and into the future. Jessica Lackey: One of the things you may cover this on some of your other shows but my thought leadership comes when I get really curious about a specific subject. Erin Ollila: Yeah. Jessica Lackey: Of the, so some of the, the rationale for doing these like live trainings and teaching is because I’m like, I’m going to get curious about this for a given period of time. Jessica Lackey: And I’m going to I’m going to consume, [00:16:00] I’m going to curate, I’m going to my own analysis spin on it and by deepening my analysis, but it’s,, I’ve. Come up with something new. And I’m like, this is what I see as the gaps, but I think it comes with something that you’re learning about. Like, maybe it’s like learning about you’re growing your business, , different things that used to work no longer work, , why things that are really working well, like what about them is working well, but I think there has to be for a thought leadership. Jessica Lackey: I think there’s an always an overarching, like learning curiosity, either about the subject at hand or. How to get your thought leadership in front of more people. I think there is a learning about how to do that actually sharpens your thought leadership it’s, you know, like sharpening it for a presentation is different than sharpening it for a keynote, which is different than sharpening it for a, you’re like, you’re thinking about different things to hone in those scenarios. Jessica Lackey: And so I think thought leadership, for thought leadership’s sake, is really hard, but having like a focused, [00:17:00] Reason for sharpening your thoughts and communicating them better changes the nature of like how you spend your time and energy. Erin Ollila: Yeah, we actually haven’t really talked about that in any of the other episodes, and I think it’s really important, ? Because I think that’s kind of what separates, , a good speaker from a thought leader, ? Or, no, it doesn’t have to be speaking. A good, creative, or someone who is able to actually kind of like, you know, I don’t, I don’t mean this in a generic way, but regurgitate the information that they have, ? Erin Ollila: I think curio curiosity, heh, why can’t I say that word? Curiosity is what gives,, a thought leader the upper hand of being able to captivate their audience. Whether it’s because of a book that they’re reading, a podcast episode that they’re listening to, because, you know, I think everyone’s so, , Able to get surface level things. Erin Ollila: I say this all the time when it comes to marketing, and I’m not trying to, you know, take anything away from the work that I I do. You can Google anything that you want to find the answers for copywriting, marketing, anything like that. Like they are all Googleable. But will that [00:18:00] teach you how to do it? Erin Ollila: No. Will it give you the skill? No, but I don’t think that there are big secrets in this world, ? So thought leadership and being curious about things. . allows you to explore different avenues. So if you are listening to someone on a stage, if you’re in a roundtable like experience, or taking a course from someone, and you can see that their curiosity has kind of taken shape, that’s, I think, where they’re, where you’re going to get the best results. Erin Ollila: You know, people will trust you more, they’ll be more excited to keep coming back for more. of your takes on things, because they can see that it’s not just that surface level, easily , Google abled thing. That it’s something that you’ve taken the time to kind of consider and shape your thought process in order to share with them. Jessica Lackey: And that’s where I think this, , virality versus depth concept comes in as well. , there are fewer people that are potentially interested when you, when you deepen your thought leadership, when you go beyond the surface level, when you [00:19:00] go and you start to niche, quote unquote, because there’s so much You, you start going down the arcs of curiosity that really are going to hone your thought leadership. , there might be less people there, but those people are interested in a , they’re often more valuable as customers and they’re interested in a higher depth of the conversation. And so they’re potentially less 79 course as an example, but they’re more apt to buy a 10, 000 consulting package. And so, , there are some quote unquote thought leaders in the. So the partnership space that I look at their content and I’m just like, I can’t even with this because it’s so, for me, it’s not thought leadership. It’s just a regurgitation of things that they happen to get hot on a particular platform before everyone else did. And I’m like, well, that’s not thought leadership. Jessica Lackey: That’s just timing. , and then there are some people who I read everything they write. I listened to everything they do and I will throw money at them. , You [00:20:00] know, hand over fist all day long. Like, this is off topic, but , Jeremy Enns and Justin Jackson have a podcast called Podcast Marketing Trends Explained. Jessica Lackey: And then they have a roast episode. I don’t even have a podcast. I mean, I have a YouTube channel that’s like very new, but I don’t have a podcast. And they. Posted about the work they were doing. And I listened to every single episode. It’s the first one I listened to every Tuesday morning. I’m like, where’s the episode? It’s so good. It’s so valuable they’ve obviously been doing this for a really long time and it’s so applicable. Um, but it’s not, how do you start a podcast? It’s, um, how might you spend 10, 000 in, if you had a budget for that? And like, what would the nuances be around that? I’m like, that’s like fascinating stuff. Jessica Lackey: Of course, they only have like a couple hundred downloads an episode, but I bet. They have actually thriving businesses. So it’s like, you know, this is very off topic, but it’s like, how do we think about moving beyond that surface level solution? And I think the only way you can do that is actually by [00:21:00] having a purpose for thought leadership in a form that you’re regularly producing for that requires you to shape it and go beyond. The viral snippets that everyone can Google. Erin Ollila: Yeah, no, , one, I just, I say this is serendipity because immediately before our conversation, I was actually listening to their most recent, uh, YouTube video. I, I love Jeremy N’s, um, new fan of his co host, because he’s new to me. But, they are incredibly valuable, and they have such great marketing lessons, regardless of, like you mentioned, being podcasting. Erin Ollila: And, what I love about The Roast, in particularly, is that they’re so fair., when I first started my business, forever ago, I had a lot of people who were like, You should do a YouTube channel, and like, roast different websites, or content. And I’m like, I’m not the roasting person. I do see value in showcasing what’s working and what’s not working. Erin Ollila: But, from The [00:22:00] examples of audits or roast like things that I’ve seen myself, I don’t want to join those ranks. And I think that what I’ve, one of the things I find fascinating about them specifically is that their roasts are direct. And kind and helpful. And I think if anyone is interested in creating a type of marketing content for their business, where they are analyzing other businesses, it’s, it’s an excellent use case of it being done well and not done poorly. Erin Ollila: , the other thing that. It’s funny that you mention about, like, I don’t know, did you read today’s thing about how he was trying to get to a thousand downloads an episode within ten weeks? Jessica Lackey: Oh, I already listened to Erin Ollila: Okay, cause I was gonna say, I haven’t finished that, so I don’t know how many, , downloads that they’ve gotten. \ , but I’ve talked with Jeremy, cause one of the clients that I have is Descript, and I do a lot of writing for them. Erin Ollila: And I’ve interviewed Jeremy after the first, \ , report came out last year. I am a geek in the sense that if you give me stats in a report, like, I am never going to be the person to develop [00:23:00] stats or understand them until they are presented to me. But the second you present those stats to me, that’s kind of like where my curiosity, specifically, we mentioned about, like, wanting to delve deeper and develop thought leadership, you know, \ , one of the things that my editor, and I had kind of talked about was only, there’s only about a 2 percent chance Growth of podcast in a month over month based on the stats of the 2023 report, which is Because if you think about that, , and actually this is what Jeremy and I talked about in one of the articles I wrote for this, is that there’s no growth. Erin Ollila: 2 percent is no growth. Yet, podcasters continue to show up week after week to create content. And the other ironic part of this is podcasting is growing at a record rate within the past couple of years. So there’s this dynamic of you’re putting in so much effort and work for something that may not grow, yet they have the wildest opportunity for growth. Erin Ollila: And [00:24:00] I think that the way that I’ve come to feel so much more comfortable about that is what you were mentioning about the idea of like quote unquote niching. You’re going to, the people who come to you and want to consume your content, learn from you, are the right people. So you do not need a 200 percent growth on podcast episodes. Erin Ollila: Like for me, you know, like just having a, knowing a couple hundred people listen to each episode is just, it’s, it’s an honor, I would say, you know, and, and obviously podcast downloads are an interesting thing. Do those amount of people listen? I don’t know. But just having a small group who do share feedback. Erin Ollila: It’s really, truly, um, a motivator to keep going, but also, you know that what you’re creating is benefiting them. So, while that was a side story that you share, I actually think it’s very relevant to what we’re talking about. You know, it’s just a different medium. For them, it’s podcasting. But for you, in doing the roundtables and presenting monthly, it’s [00:25:00] knowing that , your curiosity, the content you’ve created around that curiosity, is something that you’re developing for your own needs as, you know, intellectual person, as a business owner, as well as benefiting the audience that comes and consumes that. Erin Ollila: You know, one thing, You might have mentioned it in the beginning, but one thing we haven’t really talked about that I think is pretty fascinating about your approach is that your roundtables are actually free events Erin Ollila: How did that decision come about for you to not charge for people to come to these events? Jessica Lackey: , there was the selfish and then the, the Dharmic. , the selfish is, I find that, , putting these things behind any kind of low ticket, , price, it decreases the number of people who can come. And I was using it as a marketing material. I didn’t have a big audience. So I’m like, well, , why not share what I know and it as a marketing tool. Jessica Lackey: But I think as I’ve gotten, as part of my cultivating my thought leadership, , I’m starting to realize. I have a position about democratizing [00:26:00] access to education. I into the business at an interesting time because I quit my job in 2021 after having gone to Harvard Business School in McKinsey and had education, , engineering training and, you know, like worked at Nike, big business, all big business. , and I came into the quote unquote online space around 2020, 2021. And this was the height of like. The 30, 000 Mastermind, where it’s a graveyard of courses content that worked pre 2020. And maybe some people that would help you in a Facebook group. Like I got really tired of it. And I, I saw people I knew, I actually enrolled in one, , a mastermind that was by someone that is more in the ethical space. Jessica Lackey: And then I also, but I saw that there was. Lack of implementation support. And I’m like, there’s, I’m like, these people are going in debt and they’re wasting money., and I, I really started to think why are we doing this? Why are we pretending that there’s some [00:27:00] secret? Like I have all of these, I you know, I have a husband with health insurance I, , own my home, right. Jessica Lackey: I, I have all these, Privileges. I don’t have children, which means I can consume podcast on podcast on podcast. And the fact that people are putting this shit behind a five figure paywall designed for business owners that are never going to, you know, they eventually might make that much money. They may recoup it, but this is just, it’s, it’s exploitation. It’s extractive and it is anti to the feminist principles that a lot of these Business owner say, and I’m like, well, you know what? Fine. I will teach you everything I have to know at a, at a reasonable level for free, because the, I believe that it’s democratizing access to education. It’s helping everyone rise, but it’s also knowledge is, I don’t say knowledge is cheap, but knowledge is cheap. Jessica Lackey: And so, , implementation is hard and how can I, Say, I don’t have secrets. You want to know something? Come to my free thing. I will tell you everything. I give you ideas. I will help guide [00:28:00] your business, , at an investment level. And if you want to work with me, you can. If you don’t, probably tell a friend. Jessica Lackey: As part of my own thought leadership in this space, , I’m like watching, particularly women charging extraordinary prices for generic information and leaving people in debt without actionable things to move it forward. Teaching one lens on the world. And I’m like, that’s my, that’s my mission in the world is to like make it easier for people to build sustainability into their businesses. Jessica Lackey: So, Erin Ollila: One thing, my favorite compliment for the podcast is that when people say like, Oh, Erin gives so much away on her show, ironically, some of the people who have made that compliment, whether they’ve done it through like a review on the podcast or, you know, um, they’ve said it in their own communities, are the people who have privately told me that they think They worry that I give too much away on my podcast. Erin Ollila: But I find that so fascinating because what my answer to that always is, is you know, my [00:29:00] providing information is not my like, strategy or implementation. They’re vastly different things. So, in the marketing world, I can give you all of the information and that does nothing to hinder you from working with me. Erin Ollila: If anything, um, the people who can’t, um, Afford at this time or who should not be hiring me because they have some decision makings to make within their own business They’re able to consume the content and make educated decisions for themselves on their own Without the help of like a strategist and then when people are ready to work with me, they know my takes on things So they’re going to know if they’re if we align on our own our own marketing beliefs, let’s say, and then they’re going to just immediately have trust in me to do my job and do it well. Erin Ollila: So I’m only benefiting myself if, in a selfish way, by presenting all of the information that I have because the people who will not work with me will be better served. [00:30:00] And the people who want to work with me will feel so much more confident about that decision. So, it’s a win win in that regard for me, and I can see the same thing working, you know, in your case of doing the roundtables, because you’re able to, , Build that trust, I think, from the people who come to the events. Erin Ollila: And like you say, you know, they don’t have to be clients, in your case, you know, it’s also giving you the opportunity to develop those thoughts. And, and that’s a wonderful win in its own right. I think a question that I have for you is, is pre event, pre monthly roundtable. How are you deciding what it is that you’re going to, , Study, like, not necessarily for the next month, but into the future. Erin Ollila: Like, how are you developing your thinking about what you’d like to continue in your thought leadership? Jessica Lackey: so I have two ways that I come up with my future thoughts. One is, , what are my clients dealing with? And so what is that [00:31:00] evergreen education or insights or something that I need to develop for my clients? So it’s like, again, a multipurpose thing. I’m like, I’m getting paid an attention to develop things that are part of my coaching and consulting practice. , and two, I’m writing a book, , about these similar concepts. It’s funny, like my brain is always wrestling with frameworks. And so I’m like, where. Just like in like the coaching, you’ve seen the coaching wheel of life where it’s got all the eight aspects of, of, of life. Jessica Lackey: And you kind of spider chart where you are on each of the dimensions. And I’m like, okay, I have these six pillars of the work that I do. And this is where my learning is curation and regurgitation. And this is where my work is analysis. And this is where my work is, , a transformative, unique piece of work that I think is, is different and, , and unique. That’s where I’m like kind of expanding those, , at those frameworks and saying, what are my clients really needing right now? Again, the systems of marketing and sales. , most of my clients that came from many of my clients saying, I want to get off [00:32:00] social media, but I don’t know what else to do. Jessica Lackey: So I went on a, you know, a couple months search on that. My last one was about time. It’s not about time management, but it’s about information management, because I realized that how I even prepare for these. Roundtables was and different because of how I store information and how I prepare for that. So I’m, what do my clients need and what do I need to flesh out as I’m writing my book and developing my body at work? And I’m looking and saying, how, where am I leaning on not enough background in history that I need to go,, dive some questions. Erin Ollila: Yeah, hearing you explain that, especially like the idea of like, here are the frameworks, right? And like, where does this fall within that level? I find it really interesting that even in developing what it is that you’re talking about, your, , You’re putting them on different levels, right? Erin Ollila: Like here is the unique only to me thought and not everything has to be that in order to have true thought leadership. You know, I [00:33:00] think that part of the reason I decided to have this, , series is cause it’s just that those two words thought leadership are, I kind of hate them. Like they’re just so, it’s one of those vague, , everyone can talk about them. Erin Ollila: No one knows what it really is. And it’s so mis, and, interpreted into be something like, let’s be on social media. Let me share my thought leadership. by posting things on social or by talking about the same topic. Not so much that it is your own individual take on things, but I actually, I think if I were to kind of define, which I haven’t done yet in these interviews, my own take on thought leadership, I think that it is kind of a tiered approach, right? Erin Ollila: Like it’s taking the thought leadership of people that in the past that you’ve learned from that, , inspire you. It’s being curious about. Topics that they’ve said about things that maybe, , hold true to you based on your own personal or professional experience. Going further into them and then again developing your own thoughts on that [00:34:00] process where it is that one unique thing. Erin Ollila: So I think it is pretty fascinating how you’ve described it in a sense that like, Your work and developing what you will use in the future is slightly tiered in that same perspective of,, not just how you plan, but like how it grows based on these round tables and things that you’ve done. Two kind of go for sides, just so I can get this in the episode. Erin Ollila: Cause I actually think this is really important for everyone. One of the things we talked about, or you had mentioned to me about this episode was that these events, these teachings that you do are actually cornerstone to your. Content creation or like the rest of your thought leadership and you’ve touched upon that for things like how you’re using You know the videos and the graphics that you’re creating in your YouTube channel But can you kind of give a little explanation about how the roundtables in particularly are? Erin Ollila: Setting up what you’re doing with the rest of your marketing Jessica Lackey: So I’m deciding on the, the [00:35:00] different round tables. I’ve got the next handful planned in my mind, again, as I’m doing the research and I’m doing the learning and I’m, I’m, I’m cure, I’m listening to the podcast again, like you’re, I’m turning my reticular activation system on to like a particular topic I’m, using that instead of like writing all these newsletters and social media copy that are unrelated to the topic. Jessica Lackey: I’m pre selling the workshop by talking about all the things I’m learning inform the round table. , and so people are getting, you know, we’re leading up to the round table and coming after the round table. So, , right now I’m in a, realize I was going to be, but, , because of some books that have come out recently, , I’ve been like devouring like couple of different positioning books. And of course my next handful of newsletters are going to be about positioning and thought leadership development and the elements of expertise. Jessica Lackey: , because I’m, I’m curating all this content, I’m pulling out the snippets and, and, and things like that. I’m testing [00:36:00] it. I’m refining the language around it. And then it goes into the blog. The teaching, which then again, goes into potentially the next revision of the course or a second course. So,,, I’m using them as fodder for each other because I’m like, that’s what I’m learning about. Jessica Lackey: That’s what I’m researching. That’s what I’m thinking about. So that informs all of the content that is in the rest of the ecosystem. Erin Ollila: Which allows you to not waste your time trying to create a ton of marketing content around things that aren’t actually relevant, you know? This is, I think, my biggest struggle after working with the big, huge brands and coming into the small business world is just seeing people spin their wheels. Like, I don’t think anything drives me more crazy than sometimes listening to people explain what they do for their marketing and hearing how irrelevant so much of it is. Erin Ollila: To Their Actual Immediate Goals. You know, you mentioned, did you write your book or are you in the process of writing your book? Jessica Lackey: , that has been the thought leadership engine that has like started all of this Erin Ollila: Yeah. Jessica Lackey: , book, what I’m thinking about for the book dictates the of the [00:37:00] teachings that I do, which it’s like a Erin Ollila: Mm hmm. Jessica Lackey: review Erin Ollila: Sure. Mm hmm. Jessica Lackey: thesis is like, you know, what’s the hypothesis. Jessica Lackey: And then you do the literature review and then you test the hypothesis and then Erin Ollila: hmm. Jessica Lackey: kind of what we’re doing here. Erin Ollila: Exactly what you’re doing, right? Which is like, in some sense, it’s like, can we get this girl another masters or something here with all this effort , Jessica Lackey: Writing the book has been the project. Erin Ollila: Yeah. Jessica Lackey: the roundtables has been the project that me into thought leadership versus thought leadership being a push. Jessica Lackey: And so I would, , I’m very much on the, like some people, I’m like, how do you write a book in 90 days? because you’ve been doing this for like 15 years and now we’re documenting it. Erin Ollila: Hmm. Jessica Lackey: my thought leadership as an exploration. Erin Ollila: Yeah, , , so it’s taking me much longer than I’ve thought, but also, , that’s why I have developed expertise because I’m doing it on purpose. Erin Ollila: I would actually kind of stay here for one more second, too. And there’s absolutely nothing wrong with doing something for an extremely long time and like, [00:38:00] you know, preparing thought leadership more quickly, like in the sense of someone who’s been a practitioner for a long time and they write a book in 90 days. Erin Ollila: That being said, the one way I would suggest that’s not the best approach is the idea that they haven’t done it before. ? So, like, in your approach, like, you’re exploring, and that’s, like you mentioned, it is taking longer, but that’s the process, is uncovering all of those potential, , talking points, things that might not have gotten addressed. Erin Ollila: And I think that,, the one downfall to being an expert who is presenting their body of, of knowledge is that they’re not considering Other perspectives very often and in the professional writing world like truly like working with a publishing house for a book Erin Ollila: they’re Totally brokenhearted when they get their first draft back and they realize that they need to have some significant edits Not because the book isn’t good But because it’s, it is either too focused in on something or it’s, , extremely [00:39:00] repetitive of the same point where a good editor is going to, , really not, I would say encourage isn’t the right word, but like force you to do the work then. Erin Ollila: So I think in the process of the way that you’re working by exploring and being curious and, , Crafting as you go is one way to know that you’re not putting, you’re not setting yourself up for that one individual perspective. So I don’t think either way is the right way. I think that they’re both really good ways. Erin Ollila: I would just suggest that if you are at the point in your career or your thought leadership where you’re ready to just jump right into something like a book or like keynote speaking and things like that, just to make sure that you’ve explored all the perspectives in order to truly be the most dynamic. Erin Ollila: And not someone who is, , using your own education and experience as the only example. Alright, Jessica. That’s it for today. \ at this point, I’m just jumping on soapboxes. So we’re gonna say thank you so much for your time. I [00:40:00] really appreciated having you here. Everyone who’s listening, I will put the ways that you can get on Jessica’s mailing list so you can kind of see what it is she’s exploring. Erin Ollila: , join her roundtables and just get to know her better because it’s a resource for you . So thank you for being here. Jessica Lackey: Thanks.

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