So you’ve decided outsourcing might make sense for your business. Smart move – but hold on before you start interviewing candidates or signing contracts.
The real question isn’t just how to outsource – it’s when to outsource. Many companies rush into the process too soon or wait too long. The key is knowing when your company should outsource and making sure you’re ready when that time comes.
This isn’t about creating bureaucracy or making things complicated. It’s about having your ducks in a row so that when your new team member starts, they can actually be productive instead of sitting around confused about what you need from them.
Successful outsourcing doesn’t happen by accident. It happens when you do the prep work before bringing someone on board. Skip this step, and you’re setting everyone up for frustration. Do it right, and you’re setting yourself up for a smooth, productive relationship that actually helps your business grow.
At Connect, we’ve seen hundreds of companies go through this process. The ones who prepared properly had great experiences. The ones who winged it… didn’t. So let’s walk through exactly what you need to do to get ready — and how to know what to outsource before you start.
| Step | What It’s About | Key Actions | Time / Cost Notes |
|---|---|---|---|
| 1. Define Your Goals | Clarify what role you need and what success looks like. |
– Write a detailed job description – Set measurable outcomes – Determine experience level – List must-have vs. nice-to-have skills |
~1–2 days of prep time |
| 2. Set a Realistic Budget | Understand actual costs and commit to at least 3–6 months. |
– Research market rates – Calculate total budget – Compare outsourcing vs. local costs – Ensure long enough commitment |
Junior: $1.5–2.5k/mo Mid-level: $2.5–4k/mo Senior: $4–6.5k/mo |
| 3. Clarify Your Processes | Define how work gets done and who manages it. |
– Document workflows – Choose project tools – Set up accounts – Define reporting & communication structure – Create templates/examples |
2–5 days to organize properly |
| 4. Security & Compliance | Protect company data and IP. |
– Ensure NDAs & IP contracts – Set data access levels – Use VPNs, 2FA, password managers – Document offboarding steps |
Usually handled by Connect; minimal extra cost |
| 5. Plan Your Onboarding | Prepare for a smooth start and early productivity. |
– Create a week-one schedule – Assign mentor/buddy – Prepare onboarding docs – Schedule early check-ins – Set 30-day goals |
Takes 1–2 days to prepare |
Read also: Understanding the Risks of Outsourcing (and How to Avoid Them)
Step 1: Define Your Goals. What Do You Actually Need?
This is where most people start too vague and pay for it later.
What This Looks Like When Done Right
Define the specific role, not just “I need help”
Bad: “I need someone to help with marketing”
Good: “I need a social media manager who can create 15 posts per week for LinkedIn and Instagram, engage with our community, analyze performance metrics, and coordinate with our content team on campaign messaging”
Identify the outcomes you’re trying to achieve
What does success look like? Be specific:
- Reduce customer support response time from 4 hours to 1 hour
- Complete financial close process by day 5 of each month instead of day 15
- Launch two new features per quarter instead of one
- Increase social media engagement by 30% in six months
Determine the level of experience needed
Junior, mid-level, or senior? This matters because:
- Junior: Needs more guidance, costs less, good for well-defined tasks
- Mid-level: Can work independently with occasional check-ins
- Senior: Can make strategic decisions, might cost 50-70% more
List must-have skills vs. nice-to-have skills
Must-have: Can’t do the job without these
Nice-to-have: Would make them even better but not dealbreakers
Your Action Items
☐ Write a detailed job description including specific responsibilities
☐ Define what success looks like in measurable terms
☐ Determine required experience level
☐ List must-have vs. nice-to-have skills
☐ Identify the main problems this role will solve
☐ Estimate how much time this work should take weekly
Pro tip from Connect: The clearer you are here, the better match we can find.
Step 2: Set a Realistic Budget: Know What Quality Actually Costs
Let’s talk about money. Because nothing derails outsourcing faster than budget mismatches.
What This Looks Like When Done Right
Research actual market rates for your region and role
Eastern European rates for skilled professionals typically run:
- Junior roles: $1,500-$2,500/month
- Mid-level roles: $2,500-$4,000/month
- Senior roles: $4,000-$6,500/month
Factor in the total cost, not just salary
When you work with Connect, your monthly rate includes everything: salary, our service fee, employment overhead, ongoing support. No surprise costs.
Compare to your local hiring costs
A mid-level developer in the US might cost $100,000+ in total comp. Through Connect, you’re looking at $36,000-$48,000 annually for equivalent expertise. That’s 60-70% savings.
Plan for a 3-6 month commitment minimum
Month 1: Onboarding
Months 2-3: Becoming productive
Months 4+: Delivering real value
Your Action Items
☐ Research market rates for your specific role
☐ Calculate your total available budget
☐ Compare outsourcing costs vs. local hiring
☐ Ensure budget allows for at least 3-6 months
☐ Get approval from whoever needs to approve spending
☐ Understand what’s included in the monthly rate
Read also: Eastern Europe Software Outsourcing: Why This Region Became Our Strategic Choice
Step 3: Clarify Your Processes. How Will Work Actually Get Done?
How will your new team member know what to do, when to do it, and how to do it your way?
What This Looks Like When Done Right
Document your key workflows
Clear answers to:
- How do tasks get assigned?
- Where is work tracked?
- What’s the approval process?
- How do we handle revisions?
- Where do completed deliverables go?
Define reporting lines and communication structure
Who does this person report to? Who do they collaborate with? What meetings will they attend?
Choose and set up your tools
Decide on:
- Project management: Jira, Asana, Trello?
- Communication: Slack, Teams, Email?
- File sharing: Google Drive, Dropbox?
- Time tracking (if you want it): Toggl, Harvest?
Set up their accounts before day one.
Establish meeting rhythms
Daily standups? Weekly check-ins? What time works for both time zones?
Create templates and examples
Show what good looks like: report templates, code style guides, design standards.
Document your company context
What does your company do? Who are your customers? What’s your tech stack? What are current priorities?
Your Action Items
☐ Document key workflows and processes
☐ Define reporting structure clearly
☐ Choose which tools you’ll use
☐ Set up user accounts and access
☐ Decide on meeting schedule and format
☐ Create templates and examples
☐ Write a brief company/team context document
☐ Designate an internal point person
Pro tip from Connect: Companies that document processes well get productive team members in 2-3 weeks. Companies that don’t can take 2-3 months.
Step 4: Security and Compliance. Protect Your Data and IP
You’re sharing sensitive information with someone outside your organization. Handle it properly.
What This Looks Like When Done Right
Legal agreements (Connect handles these)
We ensure every team member signs:
- Non-Disclosure Agreement (NDA)
- Employment contract with IP assignment
- GDPR compliance
Define data access levels
Apply the principle of least privilege: people should only access what they need for their specific role.
Set up secure access methods
Use:
- VPNs for secure connections
- Two-factor authentication (2FA) on all accounts
- Password managers for secure credential sharing
- Encrypted communication for sensitive discussions
Establish security protocols
Clear rules about:
- No downloading company data to personal devices
- No sharing credentials
- No discussing work details publicly
- Reporting security concerns immediately
Plan for offboarding security
When someone leaves: revoke all access immediately, retrieve company equipment, confirm data deletion, change shared passwords.
Your Action Items
☐ Confirm NDAs and IP agreements are in place (Connect handles this)
☐ Define what data/systems this role needs access to
☐ Set up secure access methods (VPN, 2FA, etc.)
☐ Document security protocols clearly
☐ Create an offboarding checklist
☐ Ensure compliance with your industry requirements
Step 5: Plan Your Onboarding. Set Them Up for Success
Day one shouldn’t be “here’s your login, figure it out.”
What This Looks Like When Done Right
Create a week-one schedule
- Day 1: Welcome meeting, tool access, company overview
- Day 2: Deep dive into role and responsibilities
- Day 3: Introduction to team members
- Day 4: First real assignments (small tasks)
- Day 5: Check-in on progress, answer questions
Prepare onboarding materials
Have ready: access credentials, process documentation, work examples, contact list, FAQ document.
Assign a buddy or mentor
Someone on your team to be their go-to person for questions and support.
Schedule regular check-ins early
First month:
- Daily 15-minute check-ins
- Weekly 30-60 minute deeper reviews
- End-of-month comprehensive feedback
Set clear first-month goals
What should they accomplish in 30 days? Make these goals specific and achievable.
Gather feedback both ways
Ask them: What’s unclear? What information do you still need? What could we improve?
Your Action Items
☐ Create a detailed week-one schedule
☐ Prepare all onboarding documents
☐ Assign a buddy/mentor
☐ Schedule first month check-ins
☐ Define clear first-month goals
☐ Prepare welcome materials
☐ Plan introduction meetings with team
Pro tip from Connect: Good onboarding shortens time-to-productivity dramatically.
Before You Move Forward: When You Should NOT Outsource
Real talk time. Sometimes outsourcing is the wrong move.
We’re not here to convince you into something that won’t work. We’d rather be honest now than have you waste time and money on something destined to fail.
If you’re still unsure when you should outsource, this section will help clarify whether it’s the right moment or not.
Deal-Breaker #1: You Don’t Actually Know What You Need
If you couldn’t complete Step 1 because you genuinely don’t know what role you need, you’re not ready.
Signs this is you:
- “I just need someone to help with… stuff”
- “I’ll figure out what they should do once they start”
Why it won’t work: Without clear direction, even the best professional will flounder.
What to do instead: Spend a month documenting what actually needs to happen. Define the problem clearly. Then look at outsourcing.
Deal-Breaker #2: You Need Someone Physically Present
Some work genuinely requires in-person presence.
Signs this is you:
- Role involves physical equipment or facilities
- Regulated industry prohibits remote work for certain functions
- Need someone at office every day
Why it won’t work: We provide remote professionals. That’s the model.
What to do instead: Hire locally.
Deal-Breaker #3: You Can’t Commit to At Least 3-6 Months
Outsourcing is not a short-term fix.
Signs this is you:
- “Let’s just try it for a month”
- “I need this done by next month, then we’re good”
Why it won’t work: Month one is onboarding. Month two is getting productive. Month three is when real value starts.
What to do instead: For short-term needs, hire freelancers on project platforms.
Deal-Breaker #4: You’re Not Willing to Manage Remotely
Remote work requires trust and different management practices.
Signs this is you:
- You measure productivity by hours logged, not work delivered
- You need to see people working
- You don’t trust people you can’t see
Why it won’t work: You’ll micromanage and make everyone miserable.
What to do instead: Shift your management style to focus on outcomes, or stick with local hires.
Deal-Breaker #5: Your Budget Is Unrealistic
If you’re expecting senior-level expertise at junior-level prices, we’re not the right fit.
Signs this is you:
- “I can only pay $500/month but I need a senior full-stack developer”
- “I found someone cheaper, can you match that?”
Why it won’t work: Quality costs money. Even in lower-cost markets.
What to do instead: Adjust your budget to realistic levels, or adjust expectations about experience level.
Deal-Breaker #6: You Have No Processes or Documentation
If your business runs entirely on tribal knowledge, outsourcing will be difficult.
Signs this is you:
- Nothing is written down
- Every task is done differently each time
- You’ve never documented a workflow
Why it won’t work: Remote team members can’t absorb information through office osmosis.
What to do instead: Spend time documenting how things work. Build that foundation first.
Deal-Breaker #7: You’re Looking for Magic Solutions
Outsourcing won’t fix broken processes or solve strategic confusion.
Signs this is you:
- “I’ll just hire someone and they’ll figure everything out”
- You expect immediate results with zero investment of your time
Why it won’t work: Outsourcing is a multiplier, not a miracle. It makes good operations better.
What to do instead: Fix your internal operations first. Then use outsourcing to scale.
Deal-Breaker #8: You Need Immediate Results (Like, This Week)
Quality recruitment takes time.
Signs this is you:
- “I needed this done yesterday”
- “Can’t you just assign me whoever’s available?”
Why it won’t work: Good matching takes 1-2 weeks. Onboarding takes another 1-2 weeks. Becoming productive takes another month.
What to do instead: Handle the immediate crisis with contractors. Then implement proper outsourcing for long-term capacity.
Ready to Actually Start?
If you’ve worked through this checklist and none of those deal-breakers apply, you’re in great shape.
Knowing when a company should outsource is all about timing and preparation. If your goals are clear, your processes defined, and your budget realistic, then you’re ready to move forward confidently.
What Happens Next
1. Free Consultation (30-45 minutes)
We discuss your specific requirements, timeline, budget, and whether Connect is the right fit.
2. We Start Recruiting (1-2 weeks)
We search our pre-vetted talent pool and present 2-3 strong candidates who match your needs.
3. You Interview Candidates
You talk directly with each candidate and make the final hiring decision.
4. We Handle Logistics
Employment contracts, payroll, HR administration, IT setup, we manage it all.
5. Your Team Member Starts
Day one begins with your planned onboarding. You manage their work, we handle the operational backend.
6. Ongoing Partnership
Regular check-ins, support for issues, help with scaling, performance management assistance.
What This Costs
Transparent pricing:
- Junior roles: $1,800-$2,800/month all-in
- Mid-level roles: $2,800-$4,500/month all-in
- Senior roles: $4,500-$7,000/month all-in
Compared to $8,000-$15,000/month for equivalent US-based talent.
Why Companies Choose Connect
- We focus on quality over volume (top 3% acceptance rate)
- Eastern Europe advantage: strong communication, cultural alignment, reasonable time zones
- Complete transparency: clear pricing, honest assessments
- We stay involved: ongoing support throughout the relationship
- Proven track record: hundreds of successful placements
Read also: How to Outsource Work Overseas: A Step-by-Step Guide to Foreign Outsourcing
One Final Thought
You’ve made it through this entire checklist. That tells us you’re serious about doing this right. Most companies don’t do this level of preparation. They jump in unprepared, hit problems, and blame outsourcing.
You’re different. You’re putting in the work upfront. That’s exactly the kind of client who succeeds with outsourcing. You’ve got the checklist. You know the deal-breakers. You understand what it takes.
Now it’s just a matter of taking that next step. We’re here when you’re ready.
Questions about this checklist? Reach out through our site or book a consultation. We’re happy to help you figure out if outsourcing is right for your business, and if not, we’ll tell you honestly.