3 things you must do when assigning tasks to your team

When you hire someone for your team, it’s a huge relief and easy to start assigning all of the things you don’t want to do yourself anymore.

But almost every entrepreneur forgets that even the best employees need training to do things the way you want them done!

Welcome to our new video blog for She’s Got Systems – where entrepreneurs get more done in less time with systems that actually work.

How to be a kickass boss

The delicious irony of entrepreneurship is that while you might have escaped the hierarchy and politics of a corporate office, there’s a lot to learn from the humble manager who you might assume is an a) waste of overhead spending, b) useless clog in the machine or c) an annoyance you’re glad to be rid of.

Here’s the thing… the second you hire anyone for your business, you become a manager as well as a boss. Which means that even if you hate managers in theory, you’ve got to learn how to be a better one or risk screwing up your company, overpaying for help and much, much worse.

Should you keep training or fire?

Welcome to our new video blog for She’s Got Systems – where entrepreneurs get more done in less time with systems that actually work.

Today we’re tackling the biggest question that entrepreneurs worldwide face after hiring a virtual assistant or team member when mistakes happen:

How do I know if this person needs more training or should be fired?


It’s a challenge every time because while we often want to believe the best of people, sometimes you need to cut the cord and move on. If you fire too quickly, you’ll get the reputation for being difficult and impossible to please, but the flip side of dealing with an incompetent team member is frustrating! This video will cover:

How to Establish a Great Relationship with your Team

Tens of thousands of online entrepreneurs every year decide that it’s time to get some help and hire an assistant to become more productive and outsource tasks. The challenge is that a new team member means managing their time, output, and nurturing a relationship that will last for years. Recently someone asked me:

“How do I create good relationships with my Virtual Assistant so I can make the most of her time?”

It’s a great question because it’s so relevant to freelancers, entrepreneurs and business owners worldwide.

First up, we’re assuming you already have a VA or local assistant in your business. If you’re in need of one then our Headache Free Hiring ebook is a great place to start (it’s free) to learn how to identify what you need, how to get the word out, where to look and how to select the right person for your business.

Knowing that you want to make the most of your relationship with a VA, or any employee, indicates that you not only care about growing your business but also (hopefully) the people you work with on a daily basis. And so I’m going to tell you that the biggest enemy you face is apathy.

It’s the voice that says you can bookmark this and come back to it later or not worry about this until things get “really bad.”

I want you to imagine my serious face along with a supporting hand to tell you: take the time now. Don’t let this fall to the wayside, because there’s so much more to risk than losing your VA.

Why do most Virtual Assistants quit or get fired?

Having come from those hallowed (virtual) halls of support workers, I can tell you that good VAs are getting harder to find and can therefore be selective about who they work with and why.

Here are the top 3 reasons I find Virtual Assistants turning in their notice:

  1. Inconsistent work and communication
  2. Unhappy with the work environment
  3. Overpromise and Underdeliver

“They just went quiet”

Maybe you’ve experienced this in hiring but the problem flows both ways and when you stop hearing from your boss on a regular basis, worries multiply. Especially in a virtual position when you don’t know if you’ve missed an email or a call, you’re wondering what went wrong. Or if you made a mistake, you start to worry about hours and paying bills and then – might as well find another client.

We all get busy; maybe you’re focused on another project or took a vacation from email. Not communicating with your team is just as bad as poor communication. Maybe you’ve said:

“I’ll get back to you” and then went silence for weeks,
“Let me look this over and I’ll let you know” then never followed up,
or, “Okay, when we’re ready for the next project I’ll email you.”

All of these are bad bad communication and the reason why your VA might have moved on. First of all, these statements do communicate that you’ve a) not got your shit together and b) want them to wait around while you sort it out. Unpaid, mind you.

Instead, you need to make the relationship a priority. Because it is a relationship. Imagine how well your dating life would have gone if you didn’t respond to calls or texts for weeks at a time. This kind of apathy screams “he’s just not that into you!”

[Side note from the annuals of online dating: if someone tells you they’re busy and then doesn’t reply within an hour, do not, under any circumstances write “are we going to do this or not” because I, er, she might be prompted to respond “no, because I don’t date work with rude, impatient assholes.”]

Even if the work is steady, your VA might look for greener pastures if she’s unhappy in the work environment.

How can there be a bad work environment if there’s no physical office? It’s even more important to create a proper environment that can be experienced virtually.

Because if you know Sue from HR and understand that she hates email, getting a reply with “ok, fine” just sounds like Sue is busy and will stop by your desk later to clarify any questions she may have for you. But online, it sounds like “ok (I don’t care about you at all), fine (do whatever you want, I’m not paying attention).”

We read into things. We overreact. We assume.

This isn’t about creating my ideal work environment, this is about finding a match between the environment you have and the environment your VA wants to be in.

Maybe your VA has a child, and because you want to be friendly with your team members, you spend a couple minutes each call discussing how the kids are doing. The point here isn’t if your VA has children, but what matters is if they want to discuss their family during a business call or not.

Neither approach is right. It’s simply a matter of environment and culture.

It’s the reason why some people flock to apply at the company with squishy bean bag chairs in the board room and others only to the companies with leather seating for the executive board.

The challenge is to honestly convey your style in the job description and then back it up. Check out this example from the Rocket Company founder Casey Graham:


Do you think they find the people who are the right fit with that level of specificity? Of course! Because they know who they want to hire and being honest will repel the wrong people.

Unfortunately, there’s not much you can do to salvage the relationship with a VA who doesn’t want to be there, but you can identify and replace these team members pronto. Because * shocker * those who don’t enjoy their environment, typically don’t thrive.

You gotta keep your word

It seems that all anyone wants to harp on is keeping your word to your clients. Over delivering to them. Surprise and delight.

Okay, fine, clients pay the bills. But you know who enables you to serve those clients? Your team. So you can’t say one thing and do another. It’s the fastest way to lose respect and ruin your relationship with your VA.

We already covered saying you’re going to get back to your VA on a project or task and then going silent.

Let’s add to the list of no-nos:

  • Dangling the lure of more hours and never increasing hours
  • Never giving positive feedback
  • Changing your mind about a project, especially after they’ve been started
  • Giving unclear directions and getting angry with the results
  • Emailing or asking for support after hours or during a vacation
  • Sending every task as a rush job and guilting them into doing it
  • Paying invoices late


Do you hate me yet?

I promise, even if you’ve committed some of these relationship sins it doesn’t mean your VA will quit. The challenge is that you need to take responsibility from this moment further and make sure it doesn’t happen again.

And you – sitting off to the side nodding sagely because you’ve never done any of this before? You need to ensure your business has the proper systems in place because the busier you get, the more you grow, the more likely it is to happen.

Honestly? I’ve been guilty of these mistakes too. And learned from it.

So, why should you even care if your Virtual Assistant stays for years or quits after a week?

This is so simple it hurts.

For one, hiring takes time and energy – something that’s in short supply when you get to the point of needing to hire some help.

Two, your reputation is on the line. Trust me, Virtual Assistants talk and they know who is difficult to work for, the businesses that don’t make payroll, and even those who are nice and professional to the public but treat their team like shit.

You don’t want a bad reputation in this business.

And finally, it’s more cost effective to work with the same team who know your business, clients, systems, preferences and style. It takes less of your time to manage them and reduces your expenses long term.

Okay, okay, I know I’ve got to create a better relationship with my assistant. How?

Well, I’ve got 3 simple strategies for you and a bonus swipe file so keep reading to the end (even if you’re feeling a tad overwhelmed).

Strategy #1 Check in weekly

It’s simple: you can’t know if your relationship with a VA is strong or on life support until you check in and find out.

If you have a team of less than 10 people, you need a weekly appointment with every single one of them every single week.

This is non-negotiable.

Now, I get it, you’re “location independent” and “free spirited” and all that but I do not care if a call gets moved every now and then. I do care if you are so focused on your own freedom of schedule that you do not invest in the team you’ve hired to run the business that grants you that freedom.

Every week. On the calendar. By phone or Skype or in person.

[Worried about how to introduce this to your team without sounding like the principal calling students in for detention? Keep reading, I’ve got something great for you!]

Oh, and the call can’t just be catching up and “how are yous” and such. You need an agenda. Don’t worry, I got you covered here too.

On the rare weeks that I can’t hold a call with my assistant, we simply discuss the agenda by email on the same day we were supposed to talk. Every week, without fail.

Strategy #2 Give SMART feedback

There’s a famous story from Harrison Ford about being directed by George Lucas in the Star Wars film where George would reshoot a scene and say to the actors, “do that again, but better.” It always makes me laugh because it sounds like something an entrepreneur would say.

I hate to be the one to tell you but there’s not a single virtual assistant in the world who can read your mind, so you’ve got to give SMART feedback.

We all know about SMART goals (Specific, Measurable, Actionable, Reachable, Timely) but applying the same criteria to feedback is critically important.

Let’s say your assistant has posted a blog with 3 spelling errors and an incorrectly sized photo. Do you:

a) go into WordPress and fix it yourself, internally cursing their ineptitude,
b) tell them to fix it and never find out if it’s done,
c) tell them exactly what to fix and look over their shoulder,
d) convey your expectations and keep a closer eye on their work

The clear answer is d) but before you self-flagellate let me say, again, I’ve done all of these myself.

Nowadays instead of the screaming or cursing, I might send the following email:

“There were 3 spelling errors in the most recent blog post, they were: (list them here). I need you to go into WordPress and fix this immediately as well as to resize the image. Directions are located in our team wiki. Please email me when this is complete. Please remember that the content is written and edited but always needs a final, detailed check before posting and I rely on you for this final look. Please check the previous 2 blogs for any misspellings and add this to our agenda for this week’s call so we can come up with a solution to ensure it doesn’t happen in the future.”

Is it specific? “go into WordPress”
Is it measurable? “email me when this is complete”
Is it actionable? “check the previous 2 blogs”
Is it specific? “add this to our agenda”
Is it timely” “fix this immediately”

Whenever you send directions to a team member you need to take a step back and ask if your communication conveys what you want to happen, not just what you’re upset about.

Consider this email in contrast: “I am so upset that there were multiple spelling mistakes in that blog post and it’s so embarrassing. This is supposed to be YOUR JOB and if you’re not going to do it then why should I bother? I don’t have the time to be double checking everything you do and the image was wrong too! I can’t believe this is happening!”

Uh, okay then? Note: this is how you vent to a friend or spouse, not how you communicate with your team. There’s nothing in there about what should be done, what was wrong specifically or what expectations you have except “don’t do that.”

While compliments are important, my email doesn’t include them. Personally, I find those in the middle of a constructive email to be less sincere.

For me, if you say “you’re so good at finding the right image, now just size it correctly, thanks for sending this on time” then I just see “you did something wrong.”

Instead of incorporating the compliments into the first request, I usually wait until I receive notification that they’ve completed the task. Here’s a sample draft:

“Thank you for fixing the blog typos and image resizing, I really appreciate how prompt you were in getting this done. You have great attention to detail, (VA name), and I know that when we talk on Friday and update this system it won’t happen again. I really value your support, even on seemingly insignificant things like a typo, and am so lucky to have you on the team.”

Gushy? Maybe.
Sincere? Absolutely.

The funny thing is, most entrepreneurs are way more likely to send the scathing email rather than the complimentary one.

Strategy #3 Encourage talking back

At about this point, you may be thinking that the perfect VA is just around the corner waiting, ready to do whatever you want all the time.

But I want you to encourage your assistant to talk back.

Now we like to think that “back talk” is when children scream about a curfew but there’s a big difference here because you want your team to engage in a genuine back and forth discussion when it comes to hours, pay, workload, tasks, the future and expectations.

This might be assumed, but most of the time an assistant will not feel comfortable having this discussion or initiating it, which is why you have to be persistent.

This is not a one time “you can talk to me” speech. This is a culture of encouraging feedback and not reacting negatively to news you don’t want to hear.

Imagine your assistant says “I’d like to do more challenging tasks” and you respond with some version of “ungrateful, demanding, money-hungry, pain in the ass” – do you think she’s going to open up again?

Or maybe your assistant requested a long weekend off for a family event and you groused about never getting a day off and having to cover emails and gripe, gripe, gripe.

Not only should you be encouraging feedback about what’s working and not (because how else would you know?), but you have to moderate your response.

I’m not saying bend over backwards to accommodate every whim or request. I am saying keep the lines of communication open. Your assistant wants to be heard even if every request can’t be fulfilled. And if you make the business all about me, me, me and fulfilling your wants and needs, then you can be sure your assistant will be moving on.

[Need help knowing how to say “come talk to me” without sounding insincere? Good news for you below.]

Your action steps

I’m a big believer in getting shit done, so below are your 2 action steps. Copy and paste these right into your calendar, Trello, Asana, whatever. Get them done.

  1. Schedule time to talk with each employee every week and create an agenda of discussion items
  2. Find one area to give SMART feedback and one area to compliment each team member

So here’s the thing…

I know this takes practice to say the right thing with the right tone. And I know that those little details can keep these actions steps stuck on your “to do list” for way too long.

To help you, I’ve created a swipe file of some of my favorite relationship oriented resources, and it’s full of templates you can use to make your relationship with your team stronger. Sign up below and you’ll receive:

Working Well Together Scripts & Templates

  • Let’s Talk: How to Schedule Team Calls without Freaking Them Out Email Template
  • It’s Not Me, It’s You: How to End a VA Relationship and Contract with a Clean Break Email Template
  • Pow-Wow Agenda: What to Discuss with Your VA on Weekly Calls Template
  • Back Online: How to Come Back from “Going Quiet” and Re-establish a Relationship Email Template
  • Talk to Me: How to Solicit Honest Team Feedback with 3 Email templates

Get my swipe file now!

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Back to School Shopping for Entrepreneurs

It’s time for most students to begin the school year, and there are some great deals to be found in the back to school sales. Here’s my list of 8 favorites you can get deals on:

  1. Compressed Air – you’ll find this in the college/dorm section and since everything is on sale for cash-strapped college students, you can find some good deals on these little cans to keep your electronics in working order. Every time I pick up a new can, it’s a good reminder to give my computer and printer and good cleaning