In response to a recent newsletter about Project Obstacles, I received a boatload of emails about help managing your team (whether it’s a team of one or ten).

So today, I’ll be walking through some of the challenges that you, my lovely readers, face when leading your team. I’ll then give you some quick tips to easily nip them in the bud!

Based on your responses, here are the two most common challenges:


  1. Not utilizing your team to their full capacity, because you don’t have the time to manage them.
  2. Difficulty with a team member not performing in the way you expected.

The good news is that you, beautiful lady, have full control over both situations.

And it comes down to this…

The key to being a successful manager of your business (and life) is to take full ownership of every experience.” 

The experience in this case being — team performance.

I don’t have time to manage my team (even if it’s just one person).


Ok, I get that there are only so many hours in the day, but managing your team should be moved to the TOP of the list and here’s why…

The point of having a team is so that you have more time to do other things, but with that comes a pretty big time commitment at first. The key is “at first.” In the beginning it will take more time because you are learning how to work together. You must commit the hours to train, be available for questions, and give feedback and reviews. The more work you put into the relationship at the beginning, the larger the payoff. Over time, you will develop a nice flow and find that you can spend less time teaching and more time tweaking.

Here are some quick tips to get you started!

Get Organized: Block off an hour of totally uninterrupted time. Go through your to-do list. Group it into sections. Mark what could be done by someone else, even if it requires some training.

Training Tip: Use ScreenFlow to record your screen as you perform tasks. Save them as a private video in Vimeo for your team to access. This way, you train once and your team can watch it as many times as needed.

Schedule Weekly Team Meetings: Review the big picture vision with your team and then dive into detailed tasks. Discuss what is on the agenda for the week and when items are due.

Sanity Tip: Know that things are not going to be perfect the first time. Your team is learning how to work with you, and part of that is knowing how you like to work (frequency of communication, method of delivery, writing style, etc). Make sure to give lots of feedback, both positive and points for improvement.

System Tip: Use a shared Task Management tool and keep it up to date. One of my favorites is TeamWorkPM. This is crucial for the success of your collaborations.

Dealing with a Difficult Team Member


Again, this comes down to ownership.

If a team member isn’t performing, then it’s your responsibility to give them feedback, figure out what’s going on and overcome it together. And don’t worry — I’m going to give you some tips on how to do this with ease.

Now, I’m sure some resistance will come up. You’ll tell yourself that you don’t have enough time, that you’ll “let it go this once,” or just do it yourself. Let me tell you something — you will NOT save time doing it yourself. Sure, maybe the first time, but the point is to find and train someone well enough so that you don’t have to spend any time on it at ALL! Like I said before, everyone has a learning curve and the more effort you put into training, the larger the payoff down the road.

So now let’s get down to the nitty gritty on how you can structure difficult convos with your team.

Let’s say you notice that your VA is not meeting deadlines, not communicating with you as frequently as you’d like or had a typo or two in your last few social media posts. This is what you can do:

  1. Schedule a 30 min phone call letting them know that you want to catch up on a few items.
  2. Start the call casually, be yourself, speak from your heart.
  3. Let them know that you want to check in because you’ve noticed a few things slip through the cracks and wanted to bring it up. State what you’ve noticed – missed deadlines, typos, lack of communication.
  4. Let them know that you want to figure out how to support them because you want them to grow along with the company.
  5. Invite them to speak and explain.
  6. Be prepared for them to provide constructive feedback and be OPEN to it. Perhaps they need information delivered in a more timely fashion, or maybe they need more face time (or Skype time) with you to better understand your working habits.
  7. Note: there is a difference providing feedback to you and making excuses. Be aware of the blame game — it is crucial that every person in your organization (including you) take ownership of every task that is performed. If they are blaming, ask them what SOLUTIONS they have come up with to fix the problem.

The most important thing is that you maintain your cool.

The best employees will take what you’ve said and show you that they want to make changes to improve their performance. Be ready to provide guidance and tips for them. This is your opportunity to be a leader and a mentor. If it’s appropriate, share past experiences of mistakes that you’ve made and how you’ve learned from it. This could be a HUGE opportunity to form a more meaningful connection with your employee.

If you enjoyed this post, I made a free cheatsheet for you to help manage your team like a BOSS. Enter your info below and I’ll send you a copy right now! 

xo Nicole


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