The Do’s and Don’ts of Delegating

The Do's and Don'ts of Delegating for Entrepreneurs

As I’ve mentioned a time or two, I wanted to experiment with other formats of posts (including audio posts)…this is my first go at it! Let me know what you think!

Do’s & Don’t’s of Delegating: the transcript

Hi guys, this is Michelle Nickolaisen with and today’s audio post is about delegating. Delegating is a sticky spot for a lot of business owners, especially if you’re operating as a one-person business because it is really, really crucial to grow in your business. Even if you don’t ever want to expand past one person, getting started delegating is crucial so that you don’t wind up with a super-low income cap and just so that you have more time and ability and energy to do the things that you want to do in your business instead of getting bogged down with other stuff. Right?

The potential catch-22 in getting started with delegating

The problem though, is that there’s a lot of issues that come up around delegating and one of them is that to start delegating, you need to get ahead. If you’re always operating on a really tight deadline, then you don’t have time to delegate to someone else. That’s a common excuse and sometimes it’s actually true. Because if you’re used to being able to assign things out and have them done 12 hours later because you’re the one doing them, then you actually don’t have time to delegate. You need to have, if you try to hire someone and start working with them like that, you’ll have them running around like a stressed-out headless chicken, which is not good, right?

How do you get ahead without delegating? That’s the problem and there’s a potential catch-22 to get stuck in there. What I’ve found really, really helpful is being really organized and productive, obviously. But that’s like, that sounds like a really pat answer but it’s very true. So, things like systems. Things like blocking your time. I have a post that I’ll link to in the notes that’s all about blocking your time and about how I increased my productivity by quite a bit (50% or something like that, on a daily basis measured by word count). [Here’s that post!]

And something that I do that’s been really, really helpful and has been super crucial in this, is setting aside Mondays and Fridays. So the way I have my business set-up and this might not work for you depending on what kind of business you run, or your model, but there might be a way that you can modify this framework.

Build in padding (or: how I block out my weeks)

Mondays are my administrative days. So Mondays are entirely internal business. That’s when I do things like data entry or reviewing things, looking at the work my assistant did last week, all of the stuff like that. Pitching, like if I’m pitching agents for the non-fiction book that I’m working on, that’s on Monday. All of that stuff, or follow-up, invoicing, is on Monday. Right?

Fridays are more about business development. So that’s when I work on internal content or marketing, or scheduling things out for next week. It’s less, it’s still internal work but it’s less of administrative and more with a focus on business development and marketing and strategy and things like that. And also just my internal projects, right? So like working on my NaNoWriMo book, or working on the non-fiction book proposal, things like that.

And that way Tuesday through Thursday are slated out for client work. This gives me a bit of padding. Because if I need to have my assistant do something for client work that’s going to happen on like Thursday, then I already know that I’ll be assigning it out on Monday and she can get it done on Tuesday or Wednesday. So having your week set-up so that there’s already a little bit of padding built in can be really helpful.

Learning curves & onboarding

And it just, it does, there’s definitely a learning curve involved in delegating. The onboarding time and process is going to take more time than you think and it will probably be more annoying than you think it will. Right now I am using Zirtual; it’s just like “virtual” but with a Z like Zebra instead of a V like Victor. During the first month–I’m on their 8-hour a month plan–during the first month we tore through that eight hours so fast that I had to buy an extra three hours and a big part of that, like honestly, I’m not going to lie, I was pretty annoyed about it.* A big part of that was part of the on-boarding process and now that we’re in our second or third month together, I actually had to go back through my project list (which I’m going to talk about in a second) and send her more stuff because we were on like week two, we are on the last week right now and at the end of last week we had four hours left.

Once you get into a groove, if you can make it past that initial learning curve and that initial on-boarding process, then it will take way less time than you think and they’ll learn and they’ll be getting it done faster.

It’s taking stuff off your plate and freeing up your time and energy to work on the things that you want to work on, and they’re doing it faster and faster. A couple of ways you could get started delegating, even you can get ahead and build in that buffer time, so it takes less time to teach them when it does get to on-boarding because if you’re trying to delegate and do your normal workload and on-board at the same time, like there’s going to be a couple of weeks where you work way too much, and you want to avoid that, right?

The work before the work (or: preparing to delegate)

One of the things that you can do is that you can make a note of what can be delegated; as you go throughout your week, just have a note in Google Docs or in Evernote, something like that, and make a note of what can be delegated.

And then once a week, (on like for me it would be on like Monday or Friday, it would be on a Monday really), record how-to videos or write documentation for those. Or you can do the opposite method and instead of batching it so it’s once a week, you can do like one thing a day. Because we always think it’s going to take us a long time to create this documentation that’s so necessary to delegating effectively, but if you’re just recording a video, instead of trying to write out this long comprehensive document, it doesn’t really.

You can either batch that weekly and work on that for like 2-3 weeks before your assistant starts, or you can do 1 or 2 of those how-to videos a day. At the other option, which is pretty effective too, is recording it as you do it.The only thing with that is that for the video to be effective, you need to be talking as you’re recording it. Right? And if you’re prone to working in public spaces, then you’re going to look like a crazy person because you’re going to be sitting there in the corner talking to your laptop all day as you go through your normal workflow explaining what you’re doing. So that might be better left for a day when you’re working at home or working in your office.

Another thing you can do is create a document that has project-based work as well, for after that time gets freed up and after you get past the onboarding process and you find that even though you have the same amount of hours, they’re moving slower. So that way when, especially if you are on a retainer plan like I am, I pay $200 a month for 8 hours a month and if I only use two of those hours, the other six don’t roll over from month-to-month. So, and a lot of assistant agencies have that sort of set-up, right? So if you start to reach Week 2 or Week 3 or Week 4, and you’re not going through things as fast, then you can turn to that project-based document and you can get those things done that are more back-burner, maybe very back-burner, just something that would make your life a little easier but not so easy that it needs to be prioritized right now, and you can start handing off those projects to the assistant.

Creating how-to videos & documentation without hating it

A couple of times here I’ve referenced how-to videos. My favorite tool for how-to videos for delegating is Jing. It’s really good; the only catch with Jing is that it’s for videos up to 5 minutes in length. The thing that makes Jing more usable than the other alternative that I’m going to talk about in a second, for this specific purpose is that when you record the video, up to 5 minutes, and then you just click a button, and it uploads it to their servers and gives you a link.

My set-up is that I have a folder in Google Drive called Bombchelle Internal Documentation, and then I have a folder in there that has the how-to videos and I just have one document so that it’s searchable and it says like the title of the video, what it’s for, like “How-to video for uploading a newsletter into MailChimp,” and then a link to the video. Then that way if my assistant gets confused or lost or something, she can search for it in the folder and that document will pop up that has the master list with the link to all of them. And the process is really streamlined with Jing.

The alternative is ScreencastOMatic, which is a cheesy name, but it’s a really great product. It’s very accessibly priced. They have a great free version that I don’t think has a time limit. Then they have a paid version that’s $12 a year, $12 or $15, something crazy low like that. For the free version, there’s going to be a ScreencastOMatic watermark on it but if you’re just using it for internal purposes that doesn’t really matter, right? That’s not a huge deal-breaker. The only thing is that I don’t think they have something like Jing, where you can just upload it and get that link, but they might. [Note: they totally do, for both the free & paid version.] They do also integrate with YouTube and Vimeo, Dropbox, GoogleDrive; so if you wanted to, you could just upload it to any of those venues from inside ScreencastOMatic. ScreencastOMatic is what I use for all of my video reviews and I love it. The YouTube uploading is totally seamless, it’s wonderful.

That’s a little bit about getting ahead while delegating and it does take some getting used to. One of the things for example, is that I have a newsletter that goes out Fridays for my business. And what I used to do was write and schedule the newsletter on Thursdays. Now, obviously scheduling the newsletter inside MailChimp doesn’t take a huge chunk of my time, but like it’s 15 or 30 minutes, even after I’ve written it. So that’s one of the things that I delegated. The thing is though, that for her to get the newsletter scheduled on Thursday, I need to get her the content on Wednesday. And the first couple of times, I just totally blanked on that somehow. I had it tasked out to her to schedule it on Thursday and then she’d hit me up like 10:00 AM on Thursday and be like “hey, where’s the content for this?” And I’d be like “oh yeah! I need to write that!”

I had to adjust my internal schedule a little bit and that’s something that I have to plan for when I’m doing my marketing activities. All of this is a learning curve, and you might drop the ball a couple of times, but it’s just really important to stick with it because like I said, if you stick with that first month or two of on-boarding, then you’ll find out that it’s really worth your time because it saves a lot of time and energy and things just get done automatically.

Once you get past the onboarding process, once you have all that documentation, things get done automatically and it just takes this huge weight off your shoulders that you didn’t realize was there as a business owner or as an effectively delegating freelancer.

Be like Elsa, guys. Not with the snow castle and abominable snowman. Just with delegating. 

Last but not least: Let it go

The last thing that I want to touch on is that you need to learn how to let it go. This is really hard for all of us to learn, especially because the people who tend to be business owners are high achievers and perfectionists. We just really don’t want to hand things off to other people and we’re really concerned that it’s not going to get done, and that it’s not going to get done right. And this, it’s hard, it’s hard to deal with, it really is.

You do want to make sure that whoever you’re working with is competent, hopefully that’s being addressed during your hiring and onboarding process. But the best way to address it is just to jump in with both feet and hand off everything that you can and give them feedback as you go along. Don’t expect perfection the first time and don’t be hyper-critical, but because it is important for people to know that they can make mistakes. If you create a super high pressure work environment, it’s not ideal for anyone, right?

But you do need to be able to give them feedback and be like, “Hey, I liked the way you did XYZ. Next time make sure to double-check and do blah-de-blah-de-blah.” Or whatever, right? Just make sure you’re keeping them conscious of what you want without being hyper-critical or that micromanaging boss/client that we’ve all had and all hated.

So, that’s my tips on delegating: how you might be doing it wrong and how you could be doing it better. Let me know if you have any questions. You can hit me up at the blog which will have the transcript and notes for this. I’ll put a link in the audio description. Or you can tweet at me.  Thanks so much for listening and have a great day!

*Sidenote: since recording this post, I had kind of an awful and incredibly frustrating experience with Zirtual customer service and would definitely not recommend them for a typical VA workload.