054: Ten T's of Successful Delegating
8 Dec 2025 · 18 min
This is a podcast episode by Jenny Blake (Freetime Cafe) focused on delegation for heart-based business owners. Blake presents a "5T's audit" to identify tasks to delegate (Tiny, Tedious, Time-consuming, Terrible-at, Time-sensitive) and a second set of five T's for successful delegating (Trust, Training, Technique, Time, Transition/Turnover). The episode includes promotion for Blake's BFF community, FreeTime book pre-order and toolkit (with a delegation task tracker), one mid-episode ad, and practical advice for documenting tasks and designing clear specs for delegation.
Chapters
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.
Do you already have a word or theme for 2022? If not, or if you want to add another one, I encourage you to join us in the private BFF community as we work together in 2022 to create more free time. This is a private community that I run with and for fellow heart based business owners. It is one of my favorite places to hang out online. Everybody in it is so smart and generous and resourceful. I I host a live monthly Q and A where you can ask questions about your business, get feedback, do hot seats, brainstorm with fellow business owners. There's a private podcast feed where I release bonus content that does not go out live on this podcast. And we have a community forum where we engage in what I call brilliant barter. Take a penny, leave a penny Getting feedback on new ideas, things that you're launching, sales pages. Whatever it is that you're up to, this community can be part of your beta testing group to give you feedback on your ideas, help you launch, celebrate wins and work through challenges. I encourage you to join us. The grade is currently 50% off leading up to the launch. It will never be this low again, so lock it in now. You can cancel at any time and we are going to work together through 2022 on the themes of the book. So Q1 will be dedicated to the Align stage of the free time framework. Q2 will be about design, ideal outcome, impact process and then Q3 will be all about assign, creating and optimizing your delightfully tiny team. These quarterly themes are divided into monthly themes based on the book, weekly prompts, daily thought provoking questions, and resource exchanges with the community. So we've designed something totally incredible for you right now. Again, the rate is 50% off. It will never be this low again and you can cancel at any time. So you've got nothing to lose. If you want to join a brilliant community of fellow heart based business owners, we would absolutely love to have you. Just head on over to itsfreetime.com BFF that's itsfreetime.com Bff see you inside.
I have 10 delegation T techniques for you today. The first half are five T's it's an audit to determine what to delegate next and the second half are the five T's of successful delegating. Only the first half made it into the book before I sent it off to the printer. The second half came after I turned the book in and I was trying to identify why am I still experiencing friction around what I'm delegating to whom or how the work's gonna get done. Speaking of the book and this list of 10 Ts, you are gonna get a kick out of the very first review to come in for free time. This is from Kirkus Reviews. I don't know if they genuinely liked the book or they were just trying to write something that would sort of let me down easy and not throw me under the too hard, but this is what they have to say about free time and you're gonna laugh. Given the topic of today's podcast, these two things just happen to come together at the same time. Kirkus writes a comprehensive efficiency guide for solo entrepreneurs and small business owners. All three parts of the book are well written, applicable, and actionable. Stylistically, Blake is a master of alliteration and rhyming. She's also adept at employing numbered and bulleted lists. Overall, she delivers an entertaining, instructive reading experience. An invigorating and informative time management manual. How funny is that? She is also adept at employing numbered and bulleted lists. I never thought this would be in my list of accomplishments. And then the fact that they said a master of alliteration. This came in yesterday and today is the day I'm recording 10 T's of delegation. So just a little funny haha. Side note, and it's so nerve wracking and yet exciting to have these early reviews coming in. If you haven't yet pre ordered the book, please do. I would be so grateful for your support. And once you do that, you can get early access to the audiobook within just a day or two. So if you haven't already, submit your proof of purchase@itsfreetime.com Bogogo that's my keyword. My secret phrase for buy one get one, give one. That's the pre order campaign. That's itsfreetime.com Bogogo B O G O G O All right, let's get into it. 5T's audit. This can help you determine what to delegate next. Number one Tiny get rid of tiny tasks on your plate. If they're tiny, you most likely don't need to do them. And the other thing I like about identifying really tiny tasks is that they're easier to delegate because you can more clearly provide instruction around what completion looks like. Number two Tedious. Look for areas in life and work that you find tedious, that even if they are not hard or don't seem like they should be hard, you find them tedious. They drain your energy. You don't look forward to them, you procrastinate on them. Number three Time consuming. What is taking up the bulk of your time? For example, we've had transition with podcast producer and editors and it's been a bit of a journey to try to land on the right team and the right setup. Even though I actually like editing podcasts like this one, it's very time consuming. So sometimes 30 minutes of recorded audio can take up to two hours depending on the level of editing or how sloppily I recorded the solo. Usually solo episodes don't take that long, but if I have a guest there's more complexity. There's two tracks, maybe we talked, we spoke for 45 minutes. Then that can easily take two hours of editing. So it's time consuming. And even though I enjoy it, that's two hours that I could have been building things that no one else can create that come from my head and my head alone. Sometimes I get precious about oh well, will an audio editor know exactly what to keep and what to cut and not overly cut, but not leave it too sloppy. And this is where it's important that even with time consuming, tedious or tiny tasks, we just be specific and the next time you are doing one of those tasks, imagine that you are going to delegate it and every single micro thought that you have or step that you take, write it down. Number four tasks you are terrible at. So number four is terrible at. Look at anything you're doing that not only is it tiny, tedious or time consuming, you're not even good at it or what are you still holding onto that you are terrible at? Number five time sensitive. Sometimes you like doing certain things. Let me go back to the audio editing example. Maybe I really enjoy audio editing, but it's time sensitive. Or I have another time sensitive deadline coming in and I just can't do both at once. So look for things in your business or currently on your plate where they are time sensitive and would benefit from you delegating them in order to free up your time at a crucial moment in time. So Those are the 5T's audit to determine what to delegate next. I encourage you to track this, even get out a piece of paper or wherever you take notes online on your phone in a notes app. I use Notion and you can even create columns. Maybe you don't need all five columns but really be tracking over the next week or two. What is tiny, tedious, time consuming, you're terrible at or time sensitive? I have been tracking While I respond to email I have been keeping something that I call a Delegation task tracker. A template for this will be in the FreeTime toolkit and you can get early instant access to the toolkit whenever you pre order the book and submit your proof of purchase. But I have this delegation task tracker set up where as I'm processing email I'm actually noting all of the tasks that that follow email. You know, I joke I think I wrote this in the book, but I've certainly said it on the podcast that treating email like a task is almost akin to saying run business as a task. It's so complex. Email is not one task. It actually encompasses dozens if not hundreds of decisions, processes, tasks and projects. So next time you're processing email or looking at your calendar, write down anything that falls under those five T's or conversely, write down everything you do and eventually then you can like a coin sorter, sort things into the work that is energizing and your highest and best use that you and only you can do. And then everything else later you can determine, okay, who you would assign things to, what are some examples of these types of tasks, and any additional notes. But the first step is just capturing it. I'm a big fan of collection buckets as you know, as I shared in my three part notion walkthrough series, I'll link to those episodes in the show. Notes Just the collection bucket alone is a good way to raise awareness and start the path toward problem solving.
We'll be right back just after this.
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Now let's shift to the second 5 Ts 5 Ts of successful delegating. If these 5 Ts are not in place, it's likely that you will experience friction or you won't do it at all. So let's go through them one by one. One trust. Do you trust the team member or the person that you are delegating to? If not, you probably will hold things back. You're not going to give the assignments or something that you perceive as more complex or more high stakes. So it's not just do you trust this person to be a good person, it's also do you trust their ability? And of course you can create trainings, you can design process. There's a lot you can do to enhance that trust. It's not a one way street. But I can tell you right now, if you don't trust or there's a misalignment between person and task, you're most likely going to continue hoarding those things. Number two, training. Does your team or any team member or outside vendor, contractor, even a freelancer you hire on a place like Upwork, do they have the proper training? I encourage you, as you are training somebody, record it, capture it, document it, ask them to document. Every single time they ask you a question during your onboarding process, write it down. That way none of this training goes to waste. You're not recreating the wheel every time you bring on a new person. So do they have the right training a for your organization? And that's where I'm hoping the free time book can be helpful, but also the right training for this task. Do they need to learn more about the tools that are involved or the way you want it done to be up to par?
The third T of successful delegating is technique. This really goes to the second stage of the free time framework is design. And it's really important that before you delegate. The design stage is all about designing your ideal outcomes. You know, what will this project look like when it's complete? The ideal impact. What will be the impact on your broader community, the customers, the people who are receiving this, but also designing the process? How are we going to work on this together? When will you check in with me? When do you need my approval? And when can you just keep moving without it? So this is the technique piece. Technique is so important because you don't want friction to arise with miscommunication or misalignment or misunderstanding around the how of working on any given task or project.
The fourth T is time. In order to delegate successfully, there's a couple elements around time. You need to take the time to draft a clear spec. And I think as I'm saying this, I'm going to create a sample task template that I'll put in the free time toolkit so that you have a baseline. I mean, many of you may be great at this already, but I think it takes time to craft the right kind of assignment so that it's clear and you get back what you want. If you get something back, that's not what you were looking for, that's on you. It means you didn't. You weren't clear enough. Also, does the person that you're delegating to have the time? Sometimes we don't realize. You know, I spoke at the last solo episode about our own personal capacity. Whether it's our perceived capacity or actual. And that's not just what we have on our workplace. Sometimes personal things take over. And so our capacity is oscillating at any given time. Step four is really determining and making sure how much time will this task or project take and does the other person have sufficient time? 5th and final 5t of successful delegating, turnover and transition. And this is less about any one task, but it is about thinking in advance about turnover. Every time I create anything in my business, I am imagining, what if this person, myself included, is not involved moving forward, how. How much clearer do I need to be? What else do I need to get out of my head? What else do I need to document? Because turnover and transition on a team is inevitable. It's inevitable. I mean, the times that we're in, that's what pivot was all about. The whole mantra of pivot was, if change is the only constant, let's get better at it. And I was saying that the average employee tenure, this is back in 2016, was when that book came out, that the statistics showed the average employee tenure was four to five years. But now post Covid, during COVID still the long haul of it all, there's so much turnover and change in our businesses and our teams, in people's lives, in how we're working, when and where we're working, Turnover is inevitable. How can you design your systems and your documentation and your delegation to address this in advance and not be out of your mind? If someone on your team is transitioning, but rather proud that they have helped create really clear documentation that makes it super easy to transition to another person? And sometimes I've had this many times. And I talk about in the book how to have design your role conversations, sometimes team members get bored. I mean, this happened to me at Google. I hit a wall. Didn't know it at the time, but I call it now a pivot point or a plateau. It's normal as people get used to the work, sometimes they hit their own plateau on your team and they're ready for new and different projects. So even if they're not leaving and transitioning out of your business, sometimes they want to transition their role or what they're working on. So thinking about and if you could get the book, it's see more about the design your role conversations. But that's really about as well. The better the documentation, the easier it will be for them to drop some of their draining projects and take on more projects that are exciting and expansive and in the ways that they are excited to grow. So to recap the five T's of successful delegating trust training techniques, time and transition or turnover, I hope you found this helpful and that you have a beautiful rest of your day. Everybody.
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