Mastering Content Strategy, Delegation, and Creative Efficiency

Callan Harrington 0:00
I wanted this to be very, very highly curated, and have a group there that, if they connected and heard something interesting, they could follow up organically afterward. I did not want a situation where people saw who was there and immediately tried to sell them something. Because I mentioned one time at a dinner, I saw probably at least five situations where people were like, "Okay, that's really interesting. I would love to connect after this and talk about that further." That was really cool.

You're listening to That Worked, a show that breaks down the careers of top founders and executives, pulling out the key insights that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here.

Sullivan Finlay 0:50
Sullivan, welcome back.

Callan Harrington 0:55
Instead of doing Hot Off the Press, because I feel like everybody on LinkedIn is doing Hot Off the Press on a daily basis, we're gonna switch it up and do Hacks. I hate the name, so if anybody has anything better than calling this segment Hacks, let us know.

Sullivan Finlay 1:11
Any branding specialists, feel free to reach out and give us a total rebrand for this segment. But hey, minimum viable product—do you want to kick it off first?

Callan Harrington 1:17
Okay, so my hack this week is having, as a creator, some sort of visual planning tool or board to plan out your content calendar. And I think you actually turned me on to Asana, specifically with the podcast, and then I started using it for my content. And I should say, this is not sponsored by Asana. I wish it was sponsored by Asana. I'm trying to have something with Asana, because I love their products, but Asana has been really great. Or if you use Trello or Monday or anything like that, just to be able to see different areas of production for content—whether you're making content for social, for podcasts, if you're writing a book, like really, any form of content—it allows you to plan out your content calendar and also see, "Okay, this is each stage of production for any given thing."

So in my board on Asana, for example, I have:

• Ideas – These are just plain premises that might become something or might become nothing at all.

• CH (Callan Harrington) – I need to run this by my writing partner.

• Written – These are things that I like and will eventually do something with.

• To Shoot, Shot, Edited, and Posted – Literally from an idea to posted, it's all there.

I also tag it with different categories:

• Branded Content

• Pillar Content – Things I know people like and that I will always do.

• Experimental Content – High-risk, high-reward content that I don’t want to do a lot of but mix in to try new things.

• Pillar-Adjacent Content – For example, if I have corporate characters that are pillars for me, but it's still in the corporate world without being one of those characters.

This system allows me to track what's coming up, what I’ve done a lot of and might need to back off from, and what I want to do more of. It also helps me avoid doing five experimental things in a week and tanking performance. It’s really, really helpful as a hack for me as a creator.

Callan Harrington 3:10
I had always used Asana just for business-related items—like a content calendar for a company—because there are so many moving parts, multiple people, internal and external vendors. Especially as we've launched the creative agency and do a lot more content creation, content strategy, and content planning, it's impossible to run a sophisticated, highly targeted content strategy without it.

But I found the same thing you did—I was like, "Why can't I use this for stand-up?" Chris Rock is known for this. A lot of stand-ups do this. This isn’t groundbreaking, but Chris Rock, in his newest stand-up special, showed a clip backstage where he had a board that looked like a Kanban board, where he was ordering his jokes, moving things around. My system in comedy was similar:

• Here are the jokes that are working.

• Here are the ones that need work.

• Here are the ones I haven’t tried yet.

• Here’s a five-minute set.

• Here’s a ten-minute set.

It’s amazing how much of a difference moving one joke in a set makes. And I found that LinkedIn was the same way—it was super helpful. You can also start repurposing old content. I got this from Justin Welsh. He has a million followers and says only a small percent of your audience actually sees what you post. So I started doing that, and it’s amazing how well it works.

Sullivan Finlay 4:37
Repurposing content is so interesting. Even if a video reaches 3 million people, when I repost or slightly tweak it, most people don’t even recognize that I’ve done it before.

Callan Harrington 4:59
That’s a solid one. My hack is the 10-80-10 Rule of Delegation from Dan Martell’s Buy Back Your Time.

• The first 10%: Set the stage—define what "done" looks like, create an outline, etc.

• The 80%: Someone else (or AI) does the bulk of the work.

• The final 10%: You refine and approve before it goes live.

I try to think about this constantly. Maybe you can’t delegate 100%, but 80% is a significant chunk. It’s made a huge impact on how I approach things.

Sullivan Finlay 5:59
That reminds me of hiring a video editor. A candidate mentioned website design, and I thought, "I don’t want to do that. That’s part of the 80%."

Callan Harrington 6:21
Of the services that I have offered—like creative services, RevOps services—those were big for me personally because I'm not a designer. I can't actually do that work, so by nature of that, it forces me to bring in really, really good people. That has helped a ton and helped unlock my goal of getting this business to 100% run without me.

Alright, do you want to kick off What Are You Working On?

Sullivan Finlay 6:47
A big thing for me lately has been strategically thinking through the projects that I would say are bigger in scope. They are medium-term projects, and I’ve been planning out what each of those looks like. I started doing this with a few key projects, and then I was listening to the most recent episode of Seth Godin on Comparisons podcast. They were talking a lot about early-stage business through the lens of value proposition—what is it that you're bringing to the consumer? That helped me think through where I can provide value.

I’m very visual, so I literally whiteboarded out five main ideas:

1. My working theory – What I believe to be true and want to test.

2. Key partners and process – Who is involved and how things will get done.

3. Value proposition – The core benefit to the consumer.

4. Desired end result(s) – The impact I aim for.

5. Actions needed – Concrete next steps.

This framework helps me see everything clearly and stay focused. Now that I’m auditing my time more, it allows me to dedicate time efficiently to each project.

Callan Harrington 8:01
Do you find that creating those guardrails actually allows you to be more creative?

Sullivan Finlay 8:07
100%. It’s like recess—there’s a fence around the playground so kids don’t run into the street, but inside that playground, they can do anything. It’s the same concept. Having structure actually allows me to be more creative within those boundaries.

Callan Harrington 8:21
Yeah, I found the same. For me, I finally picked up the book Influence by Robert Cialdini. I could be pronouncing his last name wrong, but he talks about the Rule of Reciprocity. Essentially, if you give somebody a gift or do them a favor, they feel compelled to return it—and often in a much bigger way.

One example: There’s a company in the space that sends giant chocolate bars to prospects, and they’re converting at a ridiculously high rate. Another company sends a book where the pages are blank, the prospect’s face is on the cover, and the back has fake quotes from celebrities like Oprah and Ted Turner. The message is, "Your story is yet to be written, and we'd love to be part of that." It’s clever.

The more customized the gift, the better. I’m thinking about applying this in small-group dinners—getting in front of executives by sending them something unique. I’ll test it and share the results.

Sullivan Finlay 9:57
Is this something where you want to be really creative with what you send, or are you scaling it over time?

Callan Harrington 10:06
I'm not 100% sure yet. In the past, I’ve done highly customized things. For example, at a previous company, we were going after a massive enterprise account. We finally got the key person on a call. He was super nice, but he said, "I hate to do this, but I have to push our follow-up call back a few weeks—we're taking our kids to Disney for the first time."

So, instead of just rescheduling, we sent a small package of Cars movie toys to his office. We didn’t hear anything until after their trip, but then we got an email saying, "Hey, we’d love to get this next meeting on the books. My son loves the toys you sent him—thank you so much."

A little research goes a long way. The challenge is figuring out how much research to do and how much you want the prospect to know you did. But when it’s done right, it’s incredibly powerful.

Sullivan Finlay 11:05
That reminds me of receiving gifts from brands I’ve worked with. A snack company once sent me a package, but instead of a regular box, they put their snacks inside a fancy silver serving platter. It looked like a high-end dinner setting, and when I lifted the lid, there were just snacks inside. It was ridiculous—it made me laugh, and I probably told ten people about it. That’s the kind of thing that sticks with you.

Callan Harrington 11:36
Exactly. To schedule big meetings, this kind of thing works—for now. Eventually, executives might just have piles of random gifts stacking up. But if it’s thoughtful and personalized, it still stands out.

Callan Harrington 14:37
Win: We had our first Insurance Executive Jeffersonian Dinner. I wanted it to be highly curated, where attendees could connect naturally without feeling like they were being sold to. It worked! I saw at least five moments where people said, "That’s interesting—I’d love to connect and talk more." That was the goal.

Loss: I underestimated the need for a strong theme. Our CEO Dinners always have a theme, but since those attendees come from different industries, the conversations stay broad. This insurance group, however, had strong opinions, and the conversation sometimes went off the rails. Lesson learned: we need a theme and need to stick to it.

Sullivan Finlay 14:37
Win: I got a great response when searching for a video editor. I put a story on Instagram and within hours had 35–40 responses. I quickly realized too many choices is a problem, so I took the story down. I filtered it down to three candidates, had great conversations, and now I’m choosing between two.

Loss: A recent collaboration video flopped. The video was longer than usual, sound balancing was off, and audience engagement dropped. I should have trusted my gut and fixed those issues before posting. Seeing comments about the sound imbalance was frustrating because I knew it was an issue but posted it anyway.

Callan Harrington 17:57
80% of the time, nobody comments on production issues. But that 20% of the time when they do, it really sticks with you.

Sullivan Finlay 18:08
Yeah, it put me in a dark place for a second. But ultimately, it’s one video. I learned from it and will do better next time.

Callan Harrington 18:41
Alright, putting this in ChatGPT. I haven’t seen it yet. Give us a new spicy hot take. Tech startups are overcomplicating growth. Everyone’s obsessed with AI automation and data-driven funnels, but real money is still in relationships and partnerships. Instead of fixing how people actually buy, most just add more tech debt. Want to win? Solve the people problem, not just the process problem.

Sullivan Finlay 19:13
I mostly agree. AI plays a role, but relationships will be even more valuable as tech advances.

Callan Harrington 19:41
Biggest deals will still come from relationships. Trust is at a premium as AI takes over. But ignoring AI entirely? That’s not an option. Businesses need both AI and relationships to survive.

Callan Harrington 20:41
That’s a wrap! Leave a review on Apple Podcasts or Spotify. If you have feedback, send it to Sullivan.

Sullivan Finlay 20:44
I'll take it. See you all next week!