Confidently Build a Winning Team to Compliment Your Business Needs (with Sandra Booker): 267

Sandra is an online business manager and founder of Any Old Task, a small but mighty group of passionate peeps who love getting stuff done and helping people run their business like a lean, but never mean, fightin’ machine.  In her (efficiently used) spare time, she teaches women how to get to $50K a year in their own virtual assistant practices, even if it’s their first year in business. Her clients include familiar names like Tarzan Kay and Laura Belgray. She’s received accolades in her community like the 40 Under 40 award and she’s on a mission to help her clients generate the same kind of raving clients she enjoys in her own business.

*This post may contain affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through a link on this blog. I would never recommend a product I don’t use or love myself!


  • Sandra shares the difference between a Virtual Assistant vs. a Business Manager:
    • Virtual Assistants are more general administrative assistants:
      • On-boarding clients
      • Scheduling
      • Handeling contracts
      • Invoicing
      • Sending out emails
    • Business Managers help with high levels of your business:
      • Manage projects
      • Manage team
      • Help you know big goals
      • Tracking metrics
  • Sandra says VAs cost anywhere from $20-40 an hour vs. an OBM which generally cost $50-125 an hour. She says some OBMs will be lower end because they are in a transitional period, moving into the Online Business Manager work.
  • When your business is in the low 6 figures, that’s when Sandra recommends hiring an OBM. She says it’s not driven directly by an income level, more so your team. When you feel it’s starting to get big enough where you can’t manage your whole team, or all the projects, then it’s time. 
  • Sandra talks about how in an interview, she ties in little tests and tricks to see what they can handle. If you ask specific questions, like their DiSC profile, or their enneagram, then you will seed out the people who didn’t take the time to find that out, the people who are not detail oriented, who are not planners, etc.
  • You should be looking to hire someone who will step in and help grow their role, and help you delegate to them.
  • In the on-boarding process, paint out the whole picture of what will be expected of them. What is that big picture? You want them to know that so they can help guide the work. So instead of just delegating task by task, give the whole picture, the whole goal, so your team members can help.
  • Sandra says that if your VA isn’t performing, don’t worry about blame–just try to fix the process. When you’re delegating, delegate the outcome, not the task.
  • Time is everything with VAs. Sandra suggests using terms like, “Can you spend 20 minutes on…” instead of just asking for a task to be completed so they have a reference of how long they think it should take. She says however long she thinks a task will take, she’ll normally times it by 1.5 when asking (30 minutes = 45 minutes) Set guidelines so you communicate your expectations.
  • Some of Sandra’s warning signs that you didn’t hire the right person:
    • Late to calls
    • Continuously missing deadlines
    • They don’t look put together on calls
    • If they’re not asking questions
    • If they’re asking questions they could google
  • Sandra says that by checking in with your people once a day, asking what they struggled with, asking what they got to today, you can see right away if they’re getting it or not. She says that within the month of hiring, you’ll know for sure if they will be a long term good fit.
  • Are you ready to hire a VA: Your first VA will probably cost you $500 a month. (10-20 hours) If you can afford to pay that for the first 3 months, go for it. Do a test project or two before hiring, and then make sure to do those checkins once they’re hired for the first month. “Make sure you are slow to hire, fast to fire.”


  • (1:31) A little more about Sandra Booker.
  • (2:10) What’s the difference between a Virtual Assistant and an Online Business Manager?
  • (3:40) Price point between a VA and an OBM.
  • (5:58) At what point in your business should you hire an OBM?
  • (6:56) How many team members should you have?
  • (7:41) Sandra’s tips and tricks for hiring.
  • (12:03) What you want to make sure you’re doing in the on-boarding process.
  • (13:20) Why you should have a mission statement.
  • (14:06) What to do if a VA isn’t delivering.
  • (16:17) How to phrase tasks/how long tasks should take for your VA.
  • (17:39) Warning signs that you didn’t hire the right person.
  • (20:44) What Sandra would say to someone who doesn’t think they’re ready to hire a VA?
  • (24:02) One of the best books Sandra’s read?
  • (24:33) What does it mean to Sandra to make an impact?
  • (25:12) Where you can connect with Sandra Booker?


“You can’t wear all the hats.”

“Your mission statement should drive your business.”

“When you’re delegating, delegate the outcome, not the task.”

“Find the balance.”

“A good VA should help you grow your revenue.”

“Make sure you are slow to hire, fast to fire.”


Connect with Sandra:

Instagram: @anyoldtask

Books mentioned in the episode:

Who Moved My Cheese?

Watch Full Episode:

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Hey! I’m Rachel. I’m a former Big Ten volleyball player turned entrepreneur and professional cheese taster (kidding–but that would be a sweet job).

I’m a Pinterest strategist for female entrepreneurs who are sick of struggling on Facebook & Instagram and want to automate their traffic and get more leads on autopilot. I’ve used Pinterest to increase my blog traffic by 34,000/month…for free!

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