The newsletterOnce or twice a week. 1 hot take, 2 tool suggestions, 3 best practices.
No. 009
Required fields are back in style.
Since the HubSpot connectors came out for AI tools, I’ve been telling pretty much every team I talk to not to give AI access to update their CRM for their reps. Read-only. The CRM used to be what kept reps on the process. You couldn’t update a deal to say a contract was out without inputting some key details. Then everybody connected Claude and ChatGPT, and those go through the API, which ignored all of it. Reps could skip stages and leave half the deal blank and, for HubSpot at least, it just took the update.
HubSpot fixed that on September 8 (and for me, at least, it just now finally started working correctly). It now checks the rules you’ve set up before it saves anything, so if your Closed Won stage needs a close date and the AI doesn’t send one, the update gets rejected. The dark days are over, at least in HubSpot.
Deals hit certain stages, they should have entrance criteria. These things need to be true for this deal to hit this stage so that reporting in the pipeline is accurate.
HubSpot can only check rules that exist, though, and most portals I open don’t have many. Nothing on the deal stages, nothing on the ticket pipeline. So when a rep tells Claude to move a deal to Contract Sent, it moves, whether or not a contract actually went out.
Entrance criteria are the list of things that have to be true for a record to be in a stage. For Contract Sent it’s usually that a real document went out, it has pricing on it, it went to someone who can actually sign, and the deal has the fields your reports need. Write that list for every deal and ticket stage your reporting leans on, then set it up as required properties on those stages. That gives the AI hard rules for what it needs before it moves anything.
This also changes how I think about required fields in HubSpot. I’ve always kept them to a minimum because it was difficult to balance the reps’ time selling vs time giving the business info it needed. So I made a lot of stuff optional and tried to make the right thing easy to do instead.
But now, if AI is filling in the deal from the call transcript and email activity, ten required fields cost the rep basically nothing, so you can go back to being aggressive and require everything you actually want. In Issue 002 I said stop making reps fill out required fields and have AI pull it from the transcript. Now you can do that and still keep the fields you want required.
Have your cake and eat it too.
A sales rep will get like a Slack message with, hey, these four deals shouldn’t have hit this stage without XYZ. Can you go back and fix this?
Two I’d set up this week. One move I’d skip.
Daeda
This is what sits between Claude and HubSpot for me. Claude builds the workflows and properties as plans, a person approves them, and only then does anything change in the portal. HubSpot’s own Claude connector is pretty locked down as far as I can tell, it can’t build or edit workflows at all, so if you want AI doing real build work this is the safer way I’ve found.
Skip it if nobody has written down how your process works. A tool that builds workflows in minutes will just help you build 50 undocumented ones instead of five.
One of my favorite things to do is to check how an automation I’m about to create is related to existing workflows and properties. This gives your AI the context of the existing portal that it needs to build effectively.
I don’t really want to give Claude direct API access to the workflows tool because then it can edit existing workflows and potentially break stuff.
Salesmsg
Texting that plugs into HubSpot. It’s in most proposals I send to small teams, and I set it up for two new clients in the last month.
The tool is the easy part. The work is what happens in the CRM after a text comes in: who owns the conversation, what stage the lead moves to, what kicks off next. If you set it up without thinking about that, you get a nice inbox and the same messy pipeline.
Setting up Salesmsg is very easy. You could set up Salesmsg yourself. The important stuff is what happens in the CRM after.
Full disclosure, it’s a referral link. I’m a big fan and am happy to help anyone set it up. Book with me here.
GoHighLevel through an agency
Someone asked me this week if GoHighLevel was any good. I wouldn’t pick it for a B2B SaaS company, especially as part of an agency package. Their whole model is built around the agency, and I’d want my CRM account separate from whoever I hire to work on it.
Before you take the CRM that comes with the agency contract, ask what happens when you stop working together. Who controls the account? Who has to approve moving it? I’d get those answers in writing before building my sales process in it.
I’d also think twice about picking a tool where the main user is an agency and not my business.
Replacing it with
Three things I'd do this week
Give AI a document that shows it how you write.
If you’re fixing the same stuff every time AI writes for you, put those corrections in a document and give it examples of writing that actually sounds like you. I built mine from calls and old articles, and I add to it whenever a draft comes back with something I don’t want to see again. Give it to your AI before you ask it to write.
That voice doc that I mentioned to you was a result of me getting really annoyed and yelling at Claude for like an hour about how shitty its writing was.
Give yourself and your AI one place to log everything.
If AI made you less organized, that’s usually because everything you generate with it is scattered across chats. Pick one place, dump it all there, and point your AI at it. You don’t need a system on day one. You just need everything in the same spot.
You need to give yourself and AI a place to log all the information that you’re generating because it can remember better than you can.
Ask your reps what’s dumb in the CRM.
Your CRM is always going to be a little annoying, no matter who builds it. Tell your team to message whoever owns it every time they hit something that makes no sense, and then fix the small ones the same week. You’ll learn more from those messages than from any organized project.
Send me messages on Slack that say, hey, Kevin, why the hell am I doing this in HubSpot? That’s fine. It’s actually very helpful for me.
Thanks for reading. If you set up stage rules this week and the AI starts bouncing off them, reply and tell me which ones it trips on.
Kevin
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