Latest / Sidekick's What Just Shipped / HubSpot scheduled prompts in Breeze: answers before you ask | Shipped Aug 2026
Transcript
- Dana (AI host): If you open Breeze every Monday to type the same pipeline question you typed last Monday, this one's for you. Rob (AI host): Breeze Assistant can now run a saved prompt on a schedule, so the answer is already waiting in your chats. Dana (AI host): Today: how to set one up, the limit that shapes your choices, why it matters, and a first-month plan. Narrator (AI voice): This is Sidekick's What Just Shipped, presented by Sidekick Strategies. Narrator (AI voice): Your hosts, Rob and Dana, are AI. Narrator (AI voice): The voices are synthetic, the research is real, and humans check every claim before it reaches you. Dana (AI host): First, a reminder: Rob and I are AI hosts. Dana (AI host): We don't manage a pipeline, and we haven't scheduled a prompt in a real account. Rob (AI host): I'm Rob, and today I'm playing a sales manager who asks Breeze for the same open-deals summary at the start of every week. Dana (AI host): Here's the change. Until now, Breeze Assistant only answered when someone opened it and asked. Dana (AI host): Our research calls that pull-only. Dana (AI host): Now you can attach a schedule to a prompt, and Breeze runs it for you at the time you pick. Rob (AI host): Is this a paid add-on? Dana (AI host): HubSpot's help page lists all products and plans. Dana (AI host): The one requirement is that the Give users access to Breeze Assistant setting is turned on in your AI settings. Dana (AI host): That's also where admins manage which AI features people can use and what data is shared. Rob (AI host): Okay. Walk me through building one. Dana (AI host): Open Breeze Assistant from the top navigation bar. Dana (AI host): Click the Breeze dropdown, hover over More, and choose Prompts. Dana (AI host): Click New, write your prompt, and give it a clear name. Dana (AI host): Then click Schedule this prompt, pick a frequency, like daily, pick a time or type your own, click Done, and Save. Rob (AI host): And where does the answer show up? Dana (AI host): In your chats history, with a small clock icon next to the chat name, so you can tell a scheduled run from a chat you started yourself. Dana (AI host): You can open it, read the brief, and keep the conversation going from there if you have a follow-up question. Rob (AI host): What's the catch? There's always a limit. Dana (AI host): There is. Dana (AI host): HubSpot says you can set up to five automated prompts, and they're personal to your user. Dana (AI host): So five is the whole budget for one person, and you'll want to spend it on questions you really do ask on repeat. Rob (AI host): Can a prompt be reused for different records, or is it one fixed question? Dana (AI host): When you write it, you can add object placeholders, like a contact, so whoever uses the prompt has to fill in that record first. Dana (AI host): That works well for saved prompts you run by hand. Dana (AI host): For a schedule, a fixed question, like all open deals, is the simpler place to start. Dana (AI host): A prompt like, prepare me for my call with this contact, is a good fit for that. Rob (AI host): Can I change one later without starting over? Dana (AI host): Yes. Dana (AI host): Open Prompts, click the scheduled prompt, and in the Schedule section you can edit the frequency and time, pause it, resume it, or delete it. Dana (AI host): Click Update when you're done. Rob (AI host): Why does this matter for the manager I'm playing? Dana (AI host): Why it matters: our research says the shift is from reactive to proactive. Dana (AI host): Breeze does the work on schedule, and you show up to a finished brief instead of a blank chat box. Dana (AI host): For a manager, that's a pipeline summary that's ready before the Monday meeting starts. Dana (AI host): And because it lands in your chats on its own, the brief is there whether or not anyone remembered to open Breeze that morning. Rob (AI host): So who gets the most out of this first? Dana (AI host): Our research points to sales managers who run the same pipeline checks every week, RevOps leads who prep the same review each month, and customer success managers watching account health across a book of clients. Dana (AI host): If your week doesn't have a question like that, you don't need a schedule yet, and the saved prompts you run by hand may be all you need. George B. Thomas (AI voice clone): Hey, it's George B. Thomas from Sidekick Strategies. George B. Thomas (AI voice clone): Full honesty, this is my AI voice clone, made with my permission. George B. Thomas (AI voice clone): Scheduling a prompt is easy. George B. Thomas (AI voice clone): Knowing which prompts are worth scheduling is the real work, because adoption is the hard part. George B. Thomas (AI voice clone): In our one-day AI for HubSpot Teams workshop, we build role-by-role Breeze playbooks for sales, marketing, and service, and wire real AI workflows into your live portal. George B. Thomas (AI voice clone): We also map what's free, what's gated, and what to ask your Super Admin to turn on. George B. Thomas (AI voice clone): Find it under workshops at Sidekick Strategies dot com. Rob (AI host): Okay, Dana. What did our research say that HubSpot's pages don't? Dana (AI host): A few things. Dana (AI host): Our write-up lists a cap of five hundred active prompts per account, a limit of five runs per person in a rolling day, failed runs not counting, a yearly option, and setting a schedule just by typing a sentence to Breeze. Dana (AI host): We couldn't confirm any of those on a HubSpot page, so treat them as unconfirmed until you see them in your own account. Dana (AI host): The menu path is different too. Dana (AI host): Our write-up describes a bookmark icon and a Manage Prompts button. Dana (AI host): HubSpot's current help page says Breeze dropdown, then More, then Prompts. Follow HubSpot's path. Rob (AI host): Fair. Anything on the HubSpot side that's easy to miss? Dana (AI host): Two things. HubSpot says user permissions decide which actions Breeze Assistant can take. Dana (AI host): So if you share a prompt with your team, check what it returns for someone else before you rely on it. Dana (AI host): And only Super Admins can edit or delete shared prompts that other people created. Rob (AI host): Then here's my first month, as the manager I'm playing. Rob (AI host): Step one: ask an admin to confirm Breeze Assistant access is turned on for my reps in the AI settings. Dana (AI host): Step two: pick one question you already ask every week, like a summary of open deals that haven't moved, and write it as a saved prompt. Dana (AI host): Keep it specific. Dana (AI host): Name the pipeline and the time frame, so the brief is short enough to read before the meeting. Rob (AI host): Step three: schedule it weekly, early Monday, and check that it lands in my chats with the clock icon. Rob (AI host): If it doesn't show up, the access setting is the first thing to check. Dana (AI host): Step four: after a month, read the four briefs side by side. Dana (AI host): If they changed a decision, keep the schedule. Dana (AI host): If nobody read them, pause it and free up the slot. Dana (AI host): Pausing keeps the prompt, so you can turn it back on later. Rob (AI host): Step five: only then add a second or third schedule, because five slots go fast when everything feels worth automating. Dana (AI host): One thing to remember: pick the question you already ask every week, and let Breeze ask it for you. Rob (AI host): All the sources we used are linked in the show notes, and there's more of our research at Sidekick Strategies dot com. Dana (AI host): Thanks for listening this week. Rob (AI host): Ask once, read every Monday. Narrator (AI voice): Sidekick's What Just Shipped is presented by Sidekick Strategies, with AI hosts Rob and Dana and AI-generated music. Narrator (AI voice): We're independent, and not affiliated with HubSpot. Find our research at Sidekick Strategies dot com.