The Biggest AI Unlock for 2026: Scheduling Tasks in Claude | Episode 104

Ever felt like you're constantly playing catch-up in customer experience? What if you had an AI assistant working proactively for you, around the clock? In this episode we dive deep into the game-changing potential of agentic AI, specifically highlighting the new scheduling feature within Claude Cowork.

Until recently, true agentic AI was largely reserved for technical experts. But with Claude Cowork, it's now accessible to the masses, allowing you to automate repetitive, insightful tasks – from daily health reports to weekly QBR prep and churn signal digests. Alex explains how this isn't just about simple automation; it's about spinning up a full agentic loop that reads context, calls tools, and adapts its output. While some limitations exist (hello, Mac desktop app!), the ability to schedule recurring, complex tasks in natural language is a massive unlock for anyone in CX. Get ready to shift from reactive to proactive and reclaim your time!

Download our Digital CX Claude Plugin Suite: shop.digitalcustomersuccess.com

If you're a new Digital CX leader looking to fast-track your onboarding, an individual contributor wanting to learn more about Digital or a senior leader looking for ways of enabling your team - look no further than the Digital CX Masterclass: visit https://digitalcustomersuccess.com/masterclass.

Transcript

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Agentic AI For Everyone

SPEAKER_00 0:22

We've been talking about agentic AI for a while now, and for the masses, that hasn't actually been a thing until recently, because Claude Co-Work has made that insanely accessible, and we're going to talk about how scheduling in Claude Co-Work is your big unlock for this year. Stay tuned. Once again, welcome to the Digital Customer Experience Podcast with me, Alex Turkovich. So glad you could join us here today and every week as we explore how digital can help enhance the customer and employee experience. My goal

Show Setup And Why It Matters

SPEAKER_00 0:55

is to share what my guests and I have learned over the years so that you can get the insights that you need to evolve your own digital programs. If you'd like more info, need to get in touch, or sign up for the weekly companion newsletter that has additional articles and resources in it, go to digitalcustomer success.com for now. Let's get started. Hello, and welcome back to the Digital CX Podcast. My name is Alex Turkovich, and uh I'm so glad to have you back uh for this episode of the show that I'm insanely excited about because we have been playing with artificial intelligence tools for a long time, and a lot of us are using them in a lot of different cool ways. Uh, I talk with you all basically on a weekly basis about some of the great things you're doing with artificial intelligence. And um, you know, make no mistake, there's a lot of great things happening in artificial intelligence, but when you look at the landscape today, up until really a month or two ago, maybe three months now, uh there have been very kind of incremental small steps towards what I'll call a gentic artificial intelligence that is democratized or available for the masses. But until now, we've kind of all been playing, to be honest with you, and that has been the advice until now is like if you're in chat, you know, use Chat GPT and play with it and all that kind of stuff. And I think that's that's still great advice. If you're if you're in, you know, if you're in artificial intelligence tools, you're playing around, you're doing some prompting, you're using it on a day-to-day basis, you're kind of playing around, you're you know, you're getting used to the idea of working with artificial intelligence. I think that's phenomenal. Puts you ahead of like a whole mess of people. It puts you in the top percentile of people that are actually doing this stuff, right? So pat on the back. Now, with Claude Co-work, things are changing a bit. Until a few weeks and months ago, truly agentic workers

What Claude Co-Work Changes

SPEAKER_00 3:10

or agents that do stuff for you on a regular basis has been reserved for kind of people on the high echelon of technical expertise and artificial intelligence know-how and all of that kind of stuff. And it hasn't really been a mainstream thing. What has changed over the course of the last few months is a while ago we saw this thing come out called Moltbot, and it changed names a couple times to you know Clawbot, and now it's OpenClaw, which is now owned by OpenAI. It's like the whatever, forget the names for a second, but basically it's this you know, the first kind of agentic thing that you would install locally on. A bunch of people went out, they bought like Mac minis to host this thing on and set a bunch of stuff up, and there's security implications, blah blah blah. I won't get into the details of it. You can Google it if you want. Anthropic was crazy smart about this whole thing because they saw people flocking to this because it was this kind of truly first agentic woodwork 24-7 AI partner and started in a hurry building the stuff into Claude. Okay, so we're today we're gonna talk about Cloud Cowork a little bit, but we're gonna talk specifically about scheduling, which is a new feature in Cloud Cowork that allows you to set up tasks and schedule them on a regular basis. Um, so we're gonna talk about the benefits, some of the drawbacks, some of the gotchas, uh, and then I want you to go play with it. So, first off, um, if you're listening to this currently in March of 2026, um, if you're a PC user on Claude, I hate to break it to you, but you're probably gonna have to wait for this a little bit because as of right now, scheduling is only a Claude co-work situation, and that is only available on the Mac desktop app, not on the web app, not on the mobile app. So, sorry, but I would imagine it's coming soon. I don't really know. So, uh right out of the gate, that's a big, big gotcha, right? Um, that doesn't mean if you're a PC user, you should stop listening. But um, it is something to be aware of. Now, if you're familiar with Claude or your Claude user, this will be kind of old hat. But those of you who are just getting into it, Claude is kind of divided into three different functionalities, really two. One is chat, like your your basic um kind of chat that we're all used to with Gemini and ChatGPT and all those, it's very, very similar. Uh, the second is code, which software engineers are using to actually write code, and a lot of, you know, a lot of people, not just software engineers, are using it, you know, to create basically uh and build cool stuff. Cowork sits kind of in the middle of it. It uses Claude Code as its engine to build things, but it uses basically the the language models of chat um to make it more accessible. So you don't have to really be in at the code level and and really understand what's happening under the hood. The re another reason why cowork is so powerful is because it gives you access to a

Connectors Skills And Plugins

SPEAKER_00 6:34

bunch of apps, bunch of the apps you already have in your ecosystem via connectors. So you can connect your Google ecosystem to it, you can connect gamma to it, or linear, or HubSpot, or just basically anything. There's a lot of stuff that already has these uh these connectors for Claude, new ones coming every day, also via MCP servers. Um, you can get access to a bunch of apps that don't like officially have a connection, but you can connect to a lot of existing apps in your ecosystem, which is insanely powerful. The second thing with cowork is that by using skills and plugins, which is essentially a collection of skills, you can give co-work these really prescriptive instructions for how to complete a certain task. That's super important if you are very a very niche user. Uh, one of the things I talked about in a previous episode is um I put together a whole collection of skills specifically for customer success and bundle them. There's a CSM one, there's a CS Leader one, a CS ops one. You can actually go download these if you want. It's at shop.digitalcustomer success.com, shameless plug. Um, but go grab them and play with them. But it's essentially a collection of skills that you want to curate for yourself. Um so you can install these and grab them from a variety of different places, including Anthropic itself. But what we're gonna talk about today is the scheduling functionality. Because what you can now do is you can set up regular recurring cadences of tasks that you do on a regular basis. So if there are things that you do daily or weekly or monthly that you want to automate with artificial intelligence or make easier with artificial intelligence, Clot will now do that for you without having to think about it. So you're you're giving it the instructions once and you're having it run in perpetuity until you don't want it to run anymore. You think about that. That's insanely powerful to be able to schedule these things in advance to run for you and to, you know, kind of be your secretary or your assistant or your your virtual assistant,

How Scheduling Works In Practice

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if you will, to do a variety of tasks that include pulling data from all your different tools and running certain tasks and skills automatically. Now, what happens is every every time that uh a scheduled task spins up, it does start a new cowork session in Claude with access to all the tools and plugins and MCP servers that you have connected to it. And you know, you can set these schedules up um in a couple different ways. You can you can do it in the scheduled section on the sidebar of Claude, um, or you can just run the slash schedule command inside co-work, which will then allow you to essentially set up that schedule with Claude itself. Now, what's cool about that? I mean, we've we've we've had scheduled automations forever, right? Um, what's different about this is you're spinning up a full agenc loop every time you this scheduled task runs, which means it can read context and call various tools and reasoning uh around, you know, maybe shifting dynamics that happen depending on what it is you're doing. So it's not just like a very, it's not a it's not a super prescriptive thing that it's doing every time. It it is it is changing its output based on what its findings are every time. So the real benefits here are that you are shifting from reactive to proactive. You're not asking it to pull stuff together in the nick of time before something is due. It's doing it for you in

From Reactive To Proactive

SPEAKER_00 10:30

advance of you having to get ready for a board meeting or a QBR or you know, whatever it may be, employee reviews, those kinds of things. You can schedule those things in advance so that you're ready for them and you have the resources at hand when you need them. You know, and then when it's done, uh the you know, the output is just waiting there for you. You don't have to babysit the work. It is essentially a it's a fundamentally different relationship with artificial intelligence. The other big real tangible benefit of this is that um, you know, this this compounds upon itself. Skills have taught Claude how to work, what you want it to do, and how it should do it. Plugins have bundled those skills together along with the apps and commands, um, you know, so that you can essentially have it handle entire processes on its own. Now, scheduling those tasks puts all of that together on repeat. And again, there's no code, there's no APIs, you don't need technical understanding of you know, cron jobs and syntax and all that kind of stuff. It's just natural language task delegation in the artificial landscape. So sounds great, sounds awesome. There are some drawbacks, right? So I mentioned at the beginning, right now this is co-work only, so this is Mac only at this time. There's a couple of other things to hear. Now, these scheduled tasks really only

Mac Only And Awake Requirement

SPEAKER_00 12:00

run when your computer is awake and if the claw desktop app is actually open. Because of the nature of claw, it is hosted on your computer, it's not in the cloud somewhere. Um, and so it does need to be on to be able to run those scheduled tasks. So if your computer happens to be shut down or asleep or in your bag when you have scheduled a task, it's not gonna run it. Okay. Now it so you know, so it'll skip the task and then run it automatically once your computer is awake. Uh, you know, once you've once you've booted your computer back up or whatnot. But it does have that limitation that you have to be active in the app for it to run that. Now it's you know, it's early days on this stuff, so it's not perfect just yet. Um, and in fact, you may find that when you first run a scheduled job, it may not work. It'll probably work, but it may not work entirely the way that you want it to work. And so a lot of times it takes a couple of iterations to get this perfect. And that's why prompt quality really, really matters and being very specific with what you want it to do and how you want to do it. Um, but then also, you know, adjusting and iterating as you go based on how it completed a task. One example is I had I had a scheduled task set up to you know look at a certain spreadsheet and give me a summary off

Prompt Iteration And Auto Rewrites

SPEAKER_00 14:59

of it on a daily basis. And turns turns out right out of the gate, it didn't have access to the sheet that I wanted it to look at. And so what it actually did, because I have the Chrome extension installed, it tried to basically pull up the spreadsheet and read through it and the super time consuming and kind of dumb, right? So um I went and modified the prompting for that scheduled task to make sure that it actually had access to the document that I wanted it to. So you do need to review the first few runs of this to make sure that it's actually doing what you want it to do. Now, another thing that you'll likely notice is that the prompt that you send to this scheduled task initially likely won't stay exactly as you wrote it. And that's because when it runs the first time, Claude will actually rewrite it based on what it learned, which is cool. And I think that is a you usually a very good thing. But like I just mentioned, you're gonna want to monitor how it's actually doing it and what the rewrites are so that the task stays true to what the intent is. And in fact, you should probably be very specific with that intent when you first start with that prompt, just to make sure that it's clear on what the actual goal is. One thing that you likely should consider is having Claude actually write these scheduled prompts for you and have it ask you clarifying questions for what it is you want to accomplish. Um, and then actually have it go validate that that prompt is actually executable before you go schedule the task. Save you a little bit of headache down the road and probably reduce you know some of the cycles until it gets it perfectly right. Okay, so I think you get it. Um it's a huge unlock. I I did come up with a short list of like 10 CX use cases that you could use scheduled tasks for. Um I'd also love to hear what your use cases are if you're currently using scheduled tasks, but here's the few that I came up with. Um, first one is like a daily health

Ten CX Scheduling Use Cases

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report. Let's have Claude on a daily basis pull data from your CRM or your CS platform if they're connected, and summarize accounts that are at risk or have no activity for a long time, um, open escalations, anything that needs your attention, hopefully before it actually lands in your inbox as an escalation. Uh, another one might be a weekly QBR prep. So every Monday, uh have a GoPoll account activity or calendar activity and go look at your QBRs for the week and help you help you get prepared for them or help you as a leader maybe help your team prepare for those upcoming QBRs. Another one might be churn signal digest. So you can set like a daily or a weekly task to scan for patterns across your account set. Uh you can look at things like uh support ticket volume spikes or login drops or feature adoption gaps or anything like that and compile that into kind of a prioritized list for CSMs uh so that they know where to focus on. Number four would be an onboarding milestone tracker. Every weekday uh or maybe once a week, check which new customers are getting ready to start onboarding or which ones are behind on their milestones, uh, you know, which ones seem to have gotten stuck in the process, which ones are graduating from the process. Uh so you know, have it give you a rundown of that. Uh number five would be a renewal pipe monitor where you can do a weekly scan of the renewals that are due in the next, I don't know, 30, 60, 90 days and give you a sense for uh you know, certain ones where you know an executive might need to get involved, for example. Number six, let's look at a competitive intel brief. Why don't you have it on a weekly basis? Research um competitor announcements, press releases, product updates, pricing changes, product reviews, anything like that, app store reviews, you know, whatever, whatever gives you your competitive intel today, point it towards that and have it give you a weekly rundown of what your competitors are doing. Guarantee they're probably doing it for you too. Number seven, uh, voice of the customer synthesis. Let's pull some NPS responses or support ticket themes or uh you know, call summaries where recurring themes were surfaced. Maybe break that up by segment and by tier. You know, try to listen for what is breaking right now, what are customers loving, what are they hating, just what's the sentiment overall? Clock can do that for you as long as you have it connected to the right data sources and tools. Gong is a perfect example of that. Number eight, CSM activity audit. Uh, run a weekly summary and see what accounts haven't had a touch point in 30 days, or which CSMs have had the most or least engagement activity. Uh, this is awesome for CS leaders who just need visibility without having to ask and without having to micromanage and get into people's weeds and also not having to spend time looking at calendars and those kinds of things. Uh, number nine, an escalation recap. So end of day summary of active escalations. You know, who's owning them, what's the last update, what's blocked. Just because when when these kinds of things pile up, things tend to fall by the wayside. So this allows you to kind of build some checks and balances and a peace of mind that nothing is you know falling through the cracks. Last one I have on the list, which is you know, more digital oriented, let's do a digital motion performance overview. Uh if you're running scaled digital CX motions, weekly automation checks, or checking in on automated journeys and how they're performing, uh things like email open rates or task completion, you know, feature adoption sequences. With that kind of insight, you can use that to optimize instead of just digging through execution logs manually and all that kind of fun stuff. Have Claude do that for you. So 10 use cases for every one of these 10, there's probably 10 more, right? So you are really only limited by your imagination and maybe data availability and quality. But I hope you can see that uh if you are using Claude, you are on a Mac, you do have access to cowork, and you're not scheduling tasks for yourself today, you're ignoring a really powerful and capable tool that you can use to own your business. I mean, like never before. So, you know, if you're one of those folks who are you kind of feel constantly behind the eight ball, maybe you don't have a good feel for what's happening uh within your book of business or within your team or whatnot, set some of this stuff up because we all have dashboards. We love dashboards, we hate dashboards. I think dashboards are honestly starting to be a thing of the past because of things like this, where you are getting briefed. This is, you know, I mean, think of this as like the White House giving the president a briefing every day. Not gonna get political, I promise. But like, you know, this stuff happens, and there's

Replacing Dashboards With Briefings

SPEAKER_00 22:48

hundreds of people pulling this briefing together for the nation's leaders every day. And um, guess what? You can do the same thing in your own little microcosm, whatever that may be, whether you're a CS leader, whether you're a CSM, whether you're, I don't know, uh a small business owner, uh, you know, you're running a services business, whatever, whatever the thing is that you're that you're either doing regularly that you need to get off your plate, or the thing that you're not able to get to because you're doing other things, let's start scheduling those tasks. Okay, so I hope this has been helpful. I've had so much fun digging into this, and uh it's been it's changed the way that I think about my day-to-day routine because now I'm not necessarily thinking about the tasks that I'm doing as oh, I gotta do this, but I'm thinking about my tasks as hey, I bet I could get Claude to either do this for me or at least help me execute on this to a high degree of success. So that's That's the episode for today. Let me know what you're doing in Claude Cowork. Let me know if there are some use cases that are super cool. Would love to get an email from you, Alex at digitalcustomers.com. And again, if you want to go check out those uh those Claude plugins that I published, just go to uh store.digitalcustomers.com or go to the website and click on store and you'll

Contact Links And Closing Asks

SPEAKER_00 24:18

be able to download those. I hope you have a great week ahead. It's always great talking to you, and we'll see you next week. Thank you for joining me for this episode of the Digital CX Podcast. If you like what we're doing, uh consider leaving us a review on your podcast platform of choice. If you're watching on YouTube, leave a comment down below. It really helps us to grow and provide value to a broader audience and get more information about the show and some of the other things that we're doing at digitalcustomer success.com. I'm Alex Drogovic. Thanks so much for listening, and we'll talk to you next week.