Onboarding Isn’t Just for Employees—It’s for Every Member of Your Team
- bryan6708
- May 30
- 6 min read
How to Set Up Contractors, Freelancers, and Vendors for Success (and Save Yourself Time, Stress, and Rework)
Why Onboarding Matters—Even When You’re Not Hiring “Employees”
Most people think onboarding is just for full-time staff.
But as a serial entrepreneur who has worked with everyone from internal teams to outside contractors, I can tell you this:
📌 If someone contributes to your business—they need to be onboarded.
That includes your:
Virtual assistant
Bookkeeper
Web developer
CPA
Podcast editor
Social media manager
Ad strategist
Graphic designer
Business coach
Paid media team
If they touch your business, they impact your results.
And if you skip onboarding?
You’ll spend more time explaining things, fixing mistakes, and redoing work that should’ve been right the first time.
The better you onboard, the better you leverage.
Let’s break down exactly how to build a lean, simple, and scalable onboarding process for every member of your extended team.
The Big Shift: From Task Management to Strategic Delegation
You can’t build a scalable business if every task has to go through you.
But here’s where most entrepreneurs get stuck:
They hire help… but still feel buried in communication, clarification, and “just checking” follow-ups.
Why? Because they don’t onboard properly.
They hand off tasks—but not the context.
They give assignments—but not expectations.
They assume things are clear—when they’re not.
📌 Delegation isn’t just about asking for help—it’s about setting someone up to succeed without constant oversight.
Step 1: Document the Basics—Before You Need Them
The best time to document your processes isn’t when you bring someone on board.
It’s before.
If you’re thinking “I don’t have time to document everything,” let me tell you this:
If you don’t document everything, you are making more work for yourself later… Put in the time now to save more of your time down the road.
✅ Where to Start:
List Recurring Tasks
What are things that need to be done regularly? Every Day? Every week? Every month?
Outline Client-Facing Processes
Anything that touches a client needs consistency and clarity, and a comprehensive guide for how the company deals with clients. How are issues handled? Who makes what decisions? The more you can spell out in advance, the less of your time it will take later to trouble-shoot or worse, make amends.
Tools and Access
Create a checklist of which tools people need, what permissions they need, and where to find the necessary information. Having a centralized filing system for all company resources is a real time-saver…. It could be housed online for maximum efficiency and accessibility.
✅ Keep It Simple:
Use a Google Doc or Notion page; store all in a central location, perhaps online
Break tasks down step by step
Use Loom to record yourself walking through the process
Add screenshots if visuals help
📌 The more you document, the easier you’re making it for your business to run without your constant oversight.
Step 2: Create a Simple Onboarding Flow for Every Role
You don’t need a complex HR system to do this well.
You just need a clear, repeatable structure.
Think of onboarding like a guided tour:
Here’s where to find things. (logistics)
Here’s how we do things. (processes and procedures)
Here’s what success looks like. (spell out expectations)
✅ What to Include in Your Contractor Onboarding:
Welcome message – Share your vision, values, and communication style
Tools & tech – Provide links, logins, and training (if needed)
Expectations – Define timelines, turnaround standards, and review process
Who’s who – Let them know who they report to and how to reach out
Scope of work – What they’re responsible for, and what they’re not
Success indicators – What does a “win” look like in this role?
📌 Example: Onboarding a Virtual Assistant
Send a welcome email with a quick Loom video introducing yourself and explaining your goals.
Share your SOPs for inbox management, social media scheduling, or calendar booking.
Provide access to Gmail, ClickUp, Canva, or wherever they’ll be working.
Set up a weekly check-in for the first 30 days.
Clarify your expectations: turnaround time, preferred communication method, working hours, etc.
Step 3: Use Technology to Simplify the Process
You don’t have to manage onboarding manually.
Let tech take the weight off your shoulders.
✅ Tools That Make Onboarding Easier:
Google Drive – Create shared folders with docs, templates, and SOPs
ClickUp / Asana / Trello – Assign onboarding tasks as a checklist
Loom – Record quick training videos once and use them again and again
Notion / Trainual – Create a centralized team handbook or knowledge base
Slack – Create a dedicated channel for new contractors or teams
Zapier – Automate onboarding steps (e.g., when you add someone to a CRM, send a welcome doc)
📌 Automate once, use forever.
Step 4: Communicate Early, Clearly, and Consistently
Communication breakdowns don’t happen because people are lazy—they happen because expectations weren’t clear.
A solid onboarding process reduces the guesswork.
✅ Best Practices for Communicating with Contractors:
Use one main channel for tasks (ClickUp, Asana, or Trello—not email threads + texts + Slack + Messenger)
Give context with every task: What’s the goal? Who’s the audience?
Ask for confirmation when assigning something new: “Does this make sense?”
Create regular check-ins based on project length (weekly, biweekly, or monthly)
Document questions and answers so you don’t repeat yourself
📌 Pro Tip:
Use this simple communication formula when assigning a task:
Task: What needs to be done, and how
Context: Why it matters / what it’s connected to
Deadline: When it’s due (schedule interim check-ins)
Success Criteria: What a great outcome looks like
Step 5: Build Accountability Into the Onboarding Process
Accountability doesn’t mean micromanagement.
It means everyone knows what’s expected—and what happens if it’s not met.
✅ How to Build Accountability Without Overwhelm:
Use checklists so nothing is missed
Assign ownership for every task or deliverable
Set up milestones for larger projects
Give feedback early to course-correct fast
Use shared dashboards so progress is visible to everyone
Recognize wins and reinforce what’s working
📌 Real Example:
A marketing consultant was juggling 4 contractors but felt like she was still doing all the work.
To gain clarity and increase efficiency, she:
Created SOPs for each contractor’s role, defining the goal and purpose for each
Used ClickUp to assign and track tasks
Implemented weekly review calls
Built in quarterly check-ins tied to results
Result? She gained back 10 hours per week—and her contractors were more engaged, consistent, and reliable.
Bonus: Re-Onboard Your Long-Time Contractors
Even if someone’s been with you for years, they may still be operating on outdated expectations.
A lot changes in your business over time. New offers, new workflows, new tech.
📌 When you update systems, re-onboard your team.
Ask:
Are we still aligned on goals?
Are our communication rhythms still working?
Does everyone know how success is measured today?
Re-onboarding helps people recommit, refresh, and reconnect to your mission.
The ROI of Contractor Onboarding
Here’s what happens when you onboard your extended team the right way:
✔ Fewer mistakes
✔ Faster turnaround
✔ Stronger relationships
✔ Better results and lower costs
✔ More freedom for you
Getting Started: Your Contractor Onboarding Checklist
✅ Define the role (scope, responsibilities, success criteria)
✅ Create a simple welcome doc or video
✅ Set up access to tools and files
✅ Share relevant SOPs or Looms
✅ Assign onboarding tasks in your PM tool
✅ Schedule a kickoff call or check-in
✅ Communicate expectations early and clearly
✅ Review progress and offer feedback at key milestones
📌 Repeat for every freelancer, contractor, and vendor you bring in.
Final Thoughts: A Great Team Doesn’t Have to Be Big—It Has to Be Aligned
You don’t need 50 employees to build something amazing.
You need a lean, trusted team that’s clear on their role, equipped with the right tools, and set up to win.
📌 The best businesses aren’t just built on talent—they’re built on systems that bring out the best in that talent.
And that all starts with onboarding.
Action Step
Who’s on your extended team that plays a vital role in your business?
Give them a shout-out in the comments—I’d love to see who’s helping you grow!
🚀 P.S. Want more support building smarter systems and tracking what drives growth?
Start with my free webinar: https://www.ralwest.com/get-webinar
💼 Ready to go deeper with other like-minded entrepreneurs?
Join me in the Livin’ the Dream Mastermind—it’s designed to teach you to shift from being the Operator to the Owner of your business. https://programs.ralwest.com/mastermind
📺 And don’t forget to subscribe to my YouTube channel for weekly insights on business systems, leadership, and entrepreneurial freedom: https://www.youtube.com/@RalWest
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