How To Get Out Of Your Own Way

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How do I get out of my own way and let my support handle things without me? There are many reasons someone might struggle with this, from communication issues to staffing issues to just plain old control issues. We’re going to dive into ALL of it, and chart a path to being able to happily delegate tasks with confidence!

    • 00:00 Introduction
    • 00:58 Get really clear on expectations
    • 02:05 How to create a process for clear communication of tasks
    • 03:18 Delegate outcomes rather than tasks
    • 04:21 How to build a process designed around outcomes
    • 05:15 For the micro-managers! Weigh the cost/benefit
    • 05:55 Questions to discover where the real problem is
    • 07:38 What if their work is poor quality?
    • 07:56 Shifting out of micro-management mode and into a more productive process
    • 09:11 What if you’re missing information?
    • 10:00 Structured check-ins
    • 11:00 Dealing with repeated questions
    • 13:56 Summary of all the steps


The transcript is below if you would prefer to read this yourself instead of watching the video!


Hey! Welcome back to or, Welcome to, Sidekick COO. I’m Sandra B your Sidekick COO and today we’re gonna be answering the question:

“How on earth do I get out of my own way so that my support can handle things without me trying to take over”? 

This is a great question and it’s definitely something that a lot of people struggle with when they bring people into their team or onto their team to help them out. Especially if you’ve been burnt before, especially if you don’t really know what the person is capable of and especially if you just have a hard time trusting people or if you really think that your way is the only way. 

There are lots of things that lead to this and if you’re a micromanager and things like that. So it’s definitely something that you do need to address because you really need to be able to trust the person you’ve hired to do the work without you getting involved. One of those things that you can do to help that situation is to get really clear on expectations. Especially when you are outsourcing to somebody like a subcontractor or a contractor coming in and doing the work for you rather than an employee. Somebody who has the autonomy to work whenever they want rather than somebody who works a schedule that you set. Getting clear on those expectations is really going to be key here because if you assign a task and you have no idea when they’re gonna get back to you about it or when it’s gonna get done and all of that, it can be a little frustrating. 

I know that one of my clients really struggled with this when we first got started. I did set the expectation with them as to how quickly I can turn things around and when they’ll hear back from me and all of that stuff but what kept happening is, they would assign me a task on a Friday afternoon and I wouldn’t see that until Monday morning. In the meantime, between Friday afternoon and Monday morning, they had just gone ahead and done the work anyway because they didn’t wanna wait.

Getting clear on those expectations so that you know:

  • when you’re gonna hear back from them,
  • how quickly they’re gonna turn things around,
  • when they are available,
  • when they are gonna actually be online and available to talk to, 

Things like that and then being okay with those expectations, that’s going to be kind of step one. 

It’s really hard to just let somebody do the work when you don’t know that they’ve actually got the task and that they’re actually going to do the work. So have a set time frame for like, okay, I assign a task, here is how those tasks get assigned for one, where does that information go? How does that information get to them? Two. Some Sort of acceptance on their end. Some sort of, “yep, I got it. I’ll take care of it” or “I don’t have any questions” or whatever. Especially if you’re not meeting on a regular basis. If they could just like say, you know, do a thumbs up, anything to acknowledge that they saw that task. 

Once they have that task, they should also be looking at whatever due date you assign, what tasks, what all is involved, and making sure that they’re gonna be able to meet that due date and let you know in advance if there’s gonna be any problems. Having all that set up to your expectations will really help that whole process go a lot smoother.

The other thing you can do to get out of your own way and to kind of help you let go a little bit more is to delegate outcomes rather than tasks. Just getting clear with somebody as to what you expect the outcome to be of the work they’re going to be doing with you rather than delegating every single task to them. So what that might look like?

Maybe you have a project management tool? (which you really should have). Put all of your tasks in there, assign it to them, and then you might say, “Okay, so and so, you’re gonna be dealing with my customer service inbox. My expectation is that everybody gets responded to within 24 hours. Here is our brand voice guide so you know how to answer people and here’s where we keep our email templates for questions that we’ve had. Here’s an FAQ for you”.

So that kind of thing where you’re giving them that overarching information rather than saying, “Hey, can you go in and answer so and so? She asked this, here’s how to respond”. “Hey here, can you answer so and so? Here’s how to respond”. The same with putting an email out. If somebody’s gonna help you with loading emails, you can say ‘the outcome is that I’m going to be sending an email out every Tuesday and I want them going out at 9:00 AM eastern to my entire list”. 

If they know that that’s the outcome, then they can help you build a process

  • making sure that you have that email written
  • making sure that they don’t have any questions in advance
  • making sure any images that need to be done are ready
  • making sure that it’s loaded and checked and all that stuff

And then adding to your outcome (the thing I missed) was that you expect that it’s going to be going out

  • with all of the merge tags correct
  • any information that is needed to be filled in is correct
  • all of the information is correct with no spelling mistakes

So whatever your outcome is, assign that to them and then just give them the tools needed to produce that outcome. Hopefully, that makes sense. 

Now, if you’re the type of person who really just gets your hands in things and you have a hard time letting go, you really are that micromanager. You like standing behind people watching them type. Or you know, if somebody is working in your inbox, you have to be in there and double checking everything they’ve sent. I want you to really think about what it is that you’re doing in the grand scheme of things. If you’ve assigned a task to somebody for say your customer service inbox and then you insist on even a year later double checking every single email that they’ve sent, you have a problem. And not that YOU specifically have a problem, but I mean like you have a problem in your business. You should be trusting that person to do the job.

You need to ask yourself why you are doing that. Are you doing that because you don’t trust that person to do the job well? Or are you trying to gather some information that you’re not getting in another way? Or are you just like really, you just really don’t trust people? Being unsure if somebody’s gonna do a good job, could be because they haven’t done a good job and you just haven’t let them go yet. So that’s one thing. Or if you just have trust issues that you just can’t seem to let go of, that’s another thing. I want you to really think about why it is that you’re constantly doing that. Because when you do that, you’re actually one, telling that person, regardless of what why you’re doing it, you are showing that person that you don’t trust them. That’s the feeling that they get. Also, you’re making it harder for them to do their job. Nobody likes to do work while they’re being watched and nobody wants to have to second guess everything they’re doing. So when somebody is doing work and they know, “oh my gosh, so and so is gonna be looking at this I bet” it is so much harder to do your job if you think that somebody is watching you. You’re really creating a stressful situation for that person and you’re making it very difficult for them to do the job well. 

You’re also saying no to things!

That time that you are using to double-check their work?  That means you’re saying NO to something else in your life. You’re saying no to something else in your business or something else in your life because you don’t have the time to do it because you have to double-check all this person’s work. If the reason you’re double checking somebody’s work is that the work is actually poor quality, they make errors all the time and it’s a problem, nothing seems to get them to do it well, then you need to get rid of that person. That person shouldn’t be on your team. That’s it.

If you find that feedback you’re giving them is, “well I wouldn’t have said that word exactly or I would’ve said it like this” when really it doesn’t change the outcome, it doesn’t really change the tone, (I’m speaking about customer service in particular) if there’s really no actual change to the outcome, then you are just micromanaging. You’re not allowing the person to do their job. If you have somebody working in your business and they’re doing customer service, all they need to know is the policies that are in place for certain situations and the general tone that you’re going to be speaking in and if there are any specific things that you would never, ever, ever say, then they need those things at the beginning. You don’t need to be looking at every single email and then correcting them on, “well, you probably should have said ‘all the best’ rather than ‘talk to you later’. It doesn’t really affect the outcome. It’s not worth mentioning, just let them serve your clients. You’re paying this person for their expertise, one would imagine. So let them implement their expertise.

Same with if you hire somebody to do web design, or if you hire somebody to do copywriting, or if you hire somebody to fix your sink, let them do their job and you just step back, okay? Really think about why you’re double checking. Then if it’s that you’re missing some information, you’re trying to gather some information that you’re not getting, (just going back to the customer service example) maybe you’re trying to figure out how many people are replying to your emails or maybe you’re trying to get an understanding of what people are interested in or whatnot. If that’s the case, again, that’s not something you should be doing. Just ask the person who’s helping you to get that information for you. Say, “Hey, something I really would like to know on a regular basis is how many people are replying to my emails. So can we find a way for you to give me that information on a regular basis in some sort of report would be really lovely”? 

So yeah, so it’s really important for you to understand what you are getting from doing that extra oversight and also what you might be losing and what you might be giving up from spending time doing that extra oversight.

The last way I’d say for getting over, like just being able to let the person you hire do the work. In addition to like setting clear expectations, setting a clear outcome, and understanding the potential gain or loss from micromanaging them, or overseeing seeing their work, is to actually just have a structured check in. You want to be checking in with your team on a regular basis. I would say at the very least, you should be checking in with your team monthly. Or SORRY! Weekly!  Oh my gosh, not monthly, weekly! You should be checking in with them weekly. 

If you are just starting out with somebody brand new, you should be checking in with them daily and you should be double-checking their work on a regular basis like daily cuz you wanna see where they’re struggling, where the errors are so that you can then correct them and see if they improve. When somebody first comes on your team, it does take a little while for them to onboard and for them to understand what their role is and the full spectrum of their responsibilities and exactly how you like things done and exactly the timelines and things like that. It takes some time and people, when they come into a role, everybody’s different. 

Some people, they’re gonna come into the role and they’re just gonna do the work. They’re not gonna ask a lot of questions cuz they’re looking stuff up, they’re looking up the answers, they’re figuring it out and they’re just doing the job. Other people are going to ask the same question a few times until it drills into their head because the question comes up when they hit this one spot, you tell them the answer and then two days later they come across it again. But it is slightly different, just slightly different enough to make them think, I wonder if it’s the same thing. And then they will ask again until they realize. 

Just know that people act differently and somebody asking a question more than once is not necessarily a problem. Asking five times. That’s a problem. If they ask the same question or roughly the same question two or three times, you know, in the first two to three weeks, I would say that that’s okay. If they ask the same question five or more times, that’s a problem and they’re probably just not gonna get it. 

Checking in with them on a regular basis and checking their work on a regular basis when they first start out, is going to be key. You really want to be in it during those first three weeks or so because that’s when you’re gonna really know and get an understanding is what, whether this person is the right fit for you or not. Basically, in the first three months, you’re working with somebody, you’ll know typically by the end of the three weeks if you’re checking in with them regularly if they’re gonna be a good fit. Definitely by the end of three months. If you’re checking in with them regularly. The old adage of higher slow, fire fast, still stands.

If you’re like after three weeks this person just isn’t getting it and you’ve spoken to them and you’ve talked to them about what’s happening, you’ve corrected the issue, you’ve asked them what they think they can do to make sure it doesn’t happen again. Get them involved in the process. That’s the other thing I see people do is business owners will just go in and correct the issue and not say anything. Or they’ll say, “oh, I saw that this was a problem, I went and corrected it”. Stuff like that doesn’t stick in people’s minds. If you go in and correct everything, they’re not learning. Okay. So if you see an error, you go back to them and say,” this is incorrect, can you please fix it”? And you open that conversation up. If it happens a second time, you say, “Hey, this is the second time I’ve noticed this issue. How do you think we can make sure this doesn’t happen again in the future? Is there some sort of process we can implement? What do you think”? Getting them involved in the solution will help make sure that they are invested and understand and can ask questions. Having them involved in the process of solving any problems that come up is really key to onboarding a new person successfully. 

Hopefully, that helps you out in regards to making sure that you can actually delegate to people and not feel like you have to be in it all the time.

  • Make sure you know what the expectations are and they know what the expectations are.
  • Make sure that there’s a process involved in all of that.
  • Make sure that you’re delegating those outcomes instead of just tasks so they actually know the grand scheme of things and how everything’s connected. You really want them to understand how A leads to B leads to C. 

Delegating those outcomes is gonna help with that. Understanding what your gaining or losing when you are double-checking people’s work constantly will help you be able to let go of that piece a little bit. Also making sure you have those structured check-ins so that you know as quickly as possible whether somebody’s gonna be a fit or not. Opening up those conversations and making sure that they understand what’s required of them and what is going really well and what is not going really well. And getting their buy-in and getting their input as to how to fix any issues that have arisen.

All right, so that’s it. Hopefully, you have a good starting place now. If you’ve liked this video, please don’t forget to like and subscribe. Also, why not share this with a friend, peer, or colleague who needs to hear it? 

Don’t forget. Together we thrive. 

Have a great one.

Meet your host

Sandra Booker, Founder of Changemaker Inc. (home to Sidekick COO and The VA Studio) and creator of Scale Society and The Advisory Board, is a mentor, Fractional COO  and growth strategist. She specializes in helping overworked, overwhelmed, multi-hatted entrepreneurs become the CEOs of sustainably scalable, and powerfully profitable businesses. 

After helping local businesses thrive, and receiving accolades in her community (like the 40 Under 40 award) Sandra turned her attention to the world of online service providers, and her clients include familiar names like Chanti Zak, Tarzan Kay, and Laura Belgray.

In her (efficiently used) spare time, she teaches others how to build and grow their own 6-figure virtual assistant practices and is on a mission to create a million jobs by helping her clients and students scale their businesses.

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