092: Train the System, Then the Person
8 Dec 2025 · 19 min
Jenny Blake explains how to build business systems that work without constant training. She walks through email management: create a guide for the system itself, use Notion cards for recurring message types, and automate labels in Help Scout and Gmail so new hires find answers without asking.
Chapters
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Training the system means how do I make the system so smart that anybody new coming in can figure out what to do? And that also makes the system and your business so much more resilient because it's not reliant on you to answer everybody's questions. The more you get things out of your mind and create labels and automation and process guides like the email guide and the manager manual, everything will start to get smarter and smarter. Your team will know where to look before bugging you with their questions. Not that anyone's ever a bother, but it's just always pointing out, hey, you have a gap in your systems here.
This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
There's a somewhat grim saying about automation that involves a dog, a machine and a man. I couldn't find the exact quote, but why do you need all three? Well, you need the machine to stay running, the man to feed the dog, and the dog to make sure that the man does not touch the machine. Now I do not take nearly such a grim view on humanity, but if you've read Freetime, you know that I'm obsessed with systems automation and documentation so that we can free the people up on our teams, ourselves included as business owners, from doing repetitive work that's in the weeds. I recently had a major revelation as it relates to email management process and not having to repeat myself and I'm so friggin excited to share it with you by the end of this episode. If you stay with me through some of the more technical stuff, you will have a solution that you do not have to keep repeating yourself as you teach other people on your team, vas, assistants and so on to jump in and help you out. If it involves email, as I say in free time, business stress is a systems problem. I know that when I get frustrated or stressed, it's usually no one person's fault. If anything, it's my fault. As the owner, I know that there's a systems opportunity. I've had more turnover in my business in the last few months than I have in over 10 years of running it. I think that's partly due to the nature of the times that we're in. It's also me navigating a book launch and trying to fill gaps leading up to the launch and then realizing how exhausted I was at the end of the launch and needing to take take a step back, regroup, reconsider. The long story short of all that is that I have been repeating myself over and over as I've had different team members coming in and out of the business trying to restructure who goes where, who's helping with what projects and programs. I don't have it nailed yet, or at least I didn't. And I learned some things the hard way that I've shared privately in the BFF community. One of the things that I realized is that when I'm in the midst of a book launch, onboarding is not my strength. And I didn't yet have good enough onboarding systems to really give people a fair shake at learning their way around the business without getting overwhelmed. One of the areas that I find myself repeating myself too often is helping people get up to speed with email. Email is particularly vexing because as I've talked about, it's not one thing, it's every aspect of the business. And for me that means looking at my personal Gmail account. And then we have two accounts in Help Scout. That's the service that we use to manage team inboxes for pivot and for free time. And I'll put a link to Help Scout in the show notes if you want to check it out. Let me walk you through this big revelation through the lens of one single email, and I'm picking one at random. But it happens to be one where I've answered the same question about how to handle it multiple times in the last few months. And as I realized again, that's no one person's fault. But every time the baton changed hands, it's as if the system didn't grow any smarter and I realized that I could not keep repeating myself. This doesn't make any sense. This is a systems flaw. So for example, let's take an email from Speakpipe. That's the service that I use if you want to leave me a voice memo for this podcast, you would go to itsfreetime.com ask. There's a plugin there from a service called Speakpipe. So when a listener, maybe you submits a question or a comment through that interface, we get an email. Several years ago, I realized that I was the bottleneck for these emails. At the time they were coming into my Gmail account and they were sitting there. They were lingering for longer than they needed to. I realized that it's not an email, it's a task. So whether it was me or someone else, I needed to write a process for what happens when a Speakpipe email comes in. We need to one listen to the audio and make sure it's for the right show. As I'm sure you can imagine, for the Pivot podcast, which I've had since 2015, I get all kinds of submissions for the other Pivot podcast with Kara and Scott, So I get a really funny peek into what people are asking them. So one, we need to listen. We need to make sure it's for the right show. If it is, we download the audio, save it into Dropbox. Then I'd like for somebody on my team to create a card in notion called Listener Question. They transcribe the audio either manually if it's a really quick question, or using a service called Description. I'll put that link in the show notes as well. And then they assign that Notion card to me. That way, the next time I'm in the studio, I can listen to that listener question, have the transcript right there in front of me. That written transcript allows me to also plan maybe that content would go well with another episode on my roadmap that I'm set to record. Ideally, my team member would also reply to the person who submitted via Speak Pipe and say, thank you so much for your submission. I'll make sure Jenny gets this and we'll let you know if and when it goes live on the podcast. So you can see that this one email from Speakpipe does involve a little bit of discernment and a few steps. As I said, we had documented this in our manager manual. However, over the last few months, as I had email inbox responsibilities, switching from one person to the next to the next to yet another, I realized that everybody was asking me, what do I do with this kind of email? And I kept saying, okay, it's in the manager manual, it's in the manager manual, or here's how to do it, here's what we do with these. So just having A manager manual is a great start. Having a process documented is good, but it's not great. And here's why. Because people didn't know where to look in the manager manual. Of course they could have done a search in notion, but that's next level if somebody's entirely new to the team and they don't even know notion that well yet. And that, my friends, is when I had the revelation I need to train the system, then the person. With all of this turnover, it showed me how I was still relying too heavily on training the person and that even though the process was documented, there was something getting missed where I was the one pointing out I still carried the knowledge about the process in my mind. So what does it mean to train the system then the person? It doesn't mean that we're leaving people on the team high and dry, but it does mean this. This is where I'm going to walk you through the flowchart that I wrote down furiously by hand as this came to me. I need to create an email guide just like the manager manual. I couldn't have instructions about email buried within different sections of the manager manual of how to run the entire business because it was too hard to find. So step one, I separated out the manager manual from the email guide and I thought to myself, I used to teach customer service reps at Google how to support our products. This was my job, teaching them how to respond to emails. And I realized that if I were a big company like Google, I would have an internal help center that exactly described how to handle all manner of emails. So step one I split out the manager manual and I created a separate email guide that is just about email. So all the same business areas apply. But now the email guide can have a lot more specificity. It's in a board view of notion so that you can easily look and jump around at different cards and see what point of entry. Where do you want to dive in to get more information on something? That's just step one.
We'll be right back just after this.
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Step two is to actually train the system to point people to the correct page of the email guide. Here's what I mean by that. I am going to now, as I document specific processes in the email guide in Notion, I'm going to start creating workflows in Help Scout and filters in Gmail that will automatically apply a short link that tells people where to go to get help answering that type of query. That brings me to another tool in the mix here. I'm using textexpander so that I can create a section in textexpander called Email Guide and create little shortcuts. So now I have a text expander that's called Apostrophe Speakpipe and I'm using apostrophe because I want the email guide to all have apostrophes so that it doesn't get mixed up with the rest of our textexpander which are actual guided canned responses. So for example, we might already have a canned response called Speakpipe that says hi name, thank you so much for submitting this voice memo for Jenny. I'll make sure she gets it and we'll let you know if and when your query goes live. Something like that. That's an actual guided response and that gets a semicolon Speakpipe. However, for the email guide, I created a card on our email guide board called Speakpipe. I got the link to that Notion card and I created a short link. This one is Apostrophe Speakpipe. So now I can create a workflow in Help Scout and my Gmail that every time an email comes in from Speakpipe, it will automatically be labeled Apostrophe Speakpipe. Then whoever on my team is checking the inbox that day, even if they're brand new, that message will already come in with a label appended to it that says Apostrophe Speakpipe. They'll type that short link into their browser and it will populate a URL that takes them to the Notion card. With the process, I could even take this a step further and auto assign emails that come in with Speakpipe to the correct person once I have that person hired on my team. So I know this might sound overwhelming and a little confusing, but let me highlight the key part of training the system then. The person training the system is that documentation exists in a separate email guide. You have a specific link to the right page of the guide and then you automatically label and filter and create workflows for inbound emails. That trains the system over time to properly label. Here's where you go to find information about how to answer this now they may still have questions. They might go look at that whole process and say what the heck is Descript? Or where do I save this in Dropbox? And you know what happens then? Every question lives three lives. This is another chapter in free time. If somebody new asks a question, if they are confused about what to do, it means our Help center guide was not specific enough so they need to ask the question. Jenny, what the heck is description? Okay, well then if I answer it, they should update the email guide. They should update that entry that says descript is really powerful audio editing and transcription software. You need to download it for your desktop to have the best user experience. Here's the link and the question lives a second life because it then goes into the documentation right on that Speak Pipe entry. Sometimes a question lives a third life, which means you're posting it publicly for customers or future community members to interact with. In this case, that's not as relevant, although I do mention all the recurring software services that I use when you sign up for the Time well Spent newsletter. In addition to that, I also just created a page itsfreetime.com tools where I'm going to publicly talk about some of the core tools to run. My business notion is definitely one of them. Descript is probably not in the top five, but I do really love it and what it's capable of with this system in mind. I'm also training my Gmail to get smarter. So I'm teaching certain messages to be automatically labeled scheduling or automatically be assigned to somebody. I have all kinds of labels that I'm getting more and more specific. Like to decide yes, no, not sure, JB to draft, JB to reply, or someone on my team's initials to draft. And that way when I'm sorting through my Gmail, I'm actually assigning not just what is this about but what action do we want to take and can I create a label with my decision? So let's say someone invites me to their podcast. I could label it Podcast scheduling and yes. And then if someone from my team goes into my inbox. They actually know what to do with it. They don't have to ask me. Oh I see this came in. Do you want to do it or not? It's already labeled yes. And then in this case the next action is scheduling. Let's return to the Speak Pipe example. Let's say it still came into my Gmail because I actually do have an account that goes to Gmail. I would set up a filter that all messages from Speakpipe automatically get labeled Apostrophe speakpipe. The reason that I'm using textexpander, the reason that I want that quick link apostrophe speakpipe is so that I can actually create a label that's short enough and not have to have this huge long URL string that would actually be pointing to the notion card with the Speakpipe process entry. I also want to be able to answer team members when I'm on the go. So let's say I'm checking Help Scout and I see that somebody left me a question. Well now I. Jenny will remember. Oh, okay. Well that's the Speakpipe process and I know that all email process are tagged in textexpander with the apostrophe. So while I'm on the go, I also won't have to go look up the page, get the link to Notion, type that link into Help Scout. The system can get smarter and we have these shortcuts. Could you do all this without Textexpander? Probably, but you'd have some unwieldy URLs that are just not that nice to look at. Although you could do that in something like Help Scout. That allows you to write a larger note that's behind the scenes to the email thread itself. It would be a little harder in Gmail. I think in Gmail you'd still need some shorter labels to indicate what to do. The point of all of this is not that we're going to neglect training the people on our teams, but think about how you can train the system first, then the person. Otherwise you're going to be doing what I was doing, stuck in this never ending loop of answering the same questions over and over each time a new person enters that area of the business, that is a systems failure. That is a bottleneck. That means that information about your business is leaving as people leave your business. Training the system means how do I make the system so smart that anybody new coming in can figure out what to do? And that also makes the system and your business so much more resilient because it's not reliant on you to answer everybody's questions, so you get to relinquish your role as all seeing question answer. As I talk about in free time as Chief Everything Officer, the more you get things out of your mind and create labels and automation and process guides like the email guide and the manager manual, everything will start to get smarter and smarter. Your team will know where to look before bugging you with their questions. Not that anyone's ever a bother, but it's just always pointing out, hey, you have a gap in your systems here. This has been helping me so much. Team members who are helping me in email are already excited to keep trying this out and that's what I've found. Rather than it being insulting to anybody, it's kind of a relief. It's like, oh, everybody's relieved. There's a better way to do this, there's an easier way to find the information they need and team members don't have to feel bad being confused because of the complexity of everything that's going on. And then me as the owner, I get to design a system to answer the question so that the system can be my little helper. I hope you found this helpful. I'll put the summary and all the links in the show notes. I can't wait to hear. If you try it out, please do report back. You know where to go. It's freetime.com ask. Thanks so much for being here. Listening everybody. Have a beautiful rest of your day.
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