Everything I Got Wrong About Outsourcing in My First 10 Years
I run one of the fastest-growing outsourcing companies in the country. Inc. 5000 number 326. Over 500 staff. Clients across 85 industries.
And I am here to tell you that I made almost every possible mistake along the way.
Not small mistakes either. Fundamental, structural, “how did I not see this” mistakes that cost me clients, cost me great people, and cost me years of growth I’ll never get back.
I’m sharing them because I think the business world has too many highlight reels and not enough honest post-mortems. And because every single one of these mistakes taught me something that eventually became a core part of how we operate today. The systems that make OA work…the ones our clients love…they all came from things that went wrong first.
Mistake #1: Treating VAs as Cost Savings Instead of Capability Building
This was my biggest early mistake, and I see other business owners make it every single day.
When I first started outsourcing, the pitch was simple: “Why pay $50,000 for a domestic hire when you can get someone overseas for a fraction of that?” It was a cost play. Pure and simple. And it worked…for a while.
But here’s what happens when you frame outsourcing as cost savings. You set the ceiling at “good enough.” You’re not investing in the person’s development. You’re not thinking about how they could grow into a strategic asset. You’re just looking for the cheapest way to get tasks off your plate.
And “good enough” is a terrible standard for anything.
The shift that changed everything was when I started thinking about VAs as capability builders. Not “how do I save money?” but “how do I add capabilities to this business that I couldn’t afford any other way?” A dedicated specialist who becomes an expert in your industry-specific software. A researcher who builds competitive intelligence you’d never have time to compile yourself. An operations person who creates systems and documentation that make your entire team more efficient.
When you stop buying cheap labor and start building capability, the ROI changes completely.
Mistake #2: Not Investing in Onboarding
For years, our onboarding process was essentially: “Here’s the client. Here are the tools. Figure it out.”
I cringe writing that. But it’s the truth. And I wasn’t alone…most companies doing outsourcing were operating the same way. Throw the new person into the deep end and see if they swim.
Some did. Many didn’t. And the ones who didn’t…that wasn’t their failure. That was ours.
Because here’s what I eventually learned: the quality of the output is directly proportional to the quality of the onboarding. A brilliant VA with bad onboarding will underperform. An average VA with excellent onboarding will exceed expectations. Every single time.
When we finally built a real onboarding system…structured training, clear SOPs, defined communication cadences, and a dedicated team leader managing the transition…our client satisfaction went through the roof. Retention improved dramatically. And the VAs themselves were happier because they weren’t set up to fail.
The lesson: if you wouldn’t throw a new domestic hire into the deep end with no training, don’t do it with an offshore team member either. The geography is different. The human needs are exactly the same.
Mistake #3: Hiring Generalists Instead of Specialists
Early on, we marketed our VAs as “general virtual assistants.” They could do a little bit of everything. Admin work. Social media. Customer service. Bookkeeping. Data entry. Research. A jack of all trades.
And the result was exactly what that saying predicts: a master of none.
Clients would hire a general VA and then be disappointed when that person couldn’t also do advanced graphic design, complex financial modeling, and enterprise CRM administration. We’d set expectations that were impossible to meet because we were selling breadth instead of depth.
The turning point came when we started matching VAs to specific roles and industries. Instead of a “general VA,” we’d place a VA with experience in pest control operations who already knew FieldRoutes software. Or a VA with a background in restaurant management who was familiar with Restaurant 365. Or a VA with real estate experience who understood CRM workflows for commercial brokers.
Specificity is everything. A generalist can do many things adequately. A specialist can do one thing exceptionally. And clients don’t need adequate. They need exceptional.
This shift is also what led us to start building industry verticals within OA…dedicated teams that focus exclusively on specific industries so the expertise compounds over time. Every client in that vertical benefits from everything we’ve learned across all the others.
Mistake #4: Not Building Systems First
This one haunts me the most because it was so preventable.
For years, we’d place a VA with a client and then…hope for the best. No documented processes. No standard operating procedures. No structured communication framework. Just two people trying to figure it out in real time.
Sometimes it worked beautifully. The client was a good communicator, the VA was highly proactive, and they built a great working relationship organically.
But more often, it was messy. The client would give vague instructions. The VA would make assumptions. Work would get done incorrectly. The client would get frustrated. The VA would get demoralized. And both sides would conclude that “outsourcing doesn’t work.”
Outsourcing works. What doesn’t work is outsourcing without systems.
That realization is what led to what we now call the OA Playbook. For every single client engagement, we build a custom playbook that documents processes and workflows, communication protocols and escalation paths, tool access and standard procedures, quality standards and review cadences, and the specific goals and KPIs for the role.
The playbook isn’t a nice-to-have. It’s the foundation. Every successful client relationship we have today runs on one. And every failed relationship I look back on…I can trace the root cause to a missing or inadequate playbook.
The Meta-Mistake: Thinking I Had It Figured Out
If there’s one overarching mistake that contained all the others, it was arrogance. Not the loud kind. The quiet kind. The kind where you’ve had some success and you start assuming your approach is right because it’s working…without asking whether it could work ten times better.
I was building a fast-growing company. Clients were signing up. Revenue was climbing. It was easy to look at the growth and conclude that our systems were solid. But growth can mask a lot of problems. You can grow despite bad systems if the market demand is strong enough. Eventually, though, the cracks show.
What finally forced the change was listening. Really listening. To clients who churned and told us why. To VAs who left and told us what was broken. To team leaders who flagged issues we’d been ignoring. That feedback…the uncomfortable, honest, sometimes painful feedback…became the blueprint for everything we rebuilt.
Today, our management structure…dedicated team leaders, operations managers, and account managers for every client…exists because of those failures. The playbook system exists because clients told us they needed more structure. The industry specialization exists because generalists weren’t cutting it. The onboarding process exists because we lost good people to bad first impressions.
None of our best systems were designed in a boardroom. They were all born from something that went wrong.
Why I’m Telling You This
I could write a blog post about how great outsourcing is. I could give you the highlight reel…the revenue growth, the Inc. 5000 ranking, the 500+ staff. And all of that is real. I’m proud of it.
But if you’re a business owner considering outsourcing for the first time…or if you’ve tried it and it didn’t work…I think the failures are more useful than the wins. Because the wins are easy to copy. The failures are where the real learning lives.
Every mistake I made, you can avoid. Not because you’re smarter than me, but because I’m handing you the playbook that took me a decade to build.
Your Next Step
The complete system…the OA Playbook framework, the onboarding structure, the delegation methodology, and every lesson from every mistake I’ve made across 25 years of entrepreneurship…is in my upcoming book, Automate and Delegate: The Modern Leader’s Guide to Scaling and Living in Your Passion Pockets, launching May 30, 2026.
This isn’t a theory book. It’s a field manual built from real failures and real fixes. Pre-order at bradstevenstraining.com/book, and join The Full Potential Dispatch newsletter for weekly insights at bradstevenstraining.com/newsletter.
