How to Hire Your First Employee or Contractor (Without Making Expensive Mistakes)

The First Hire Decision Framework

Before you hire, you must be ruthlessly honest about one question:

What is the one thing that, if someone else did it, would free up the most valuable hours for you?

Not the thing you hate most. The thing that, when freed from it, creates the most growth.

A founder who hates admin but is world-class at sales should hire an admin assistant. A founder who spends 20 hours/week on customer support but only 5 hours/week on product development should hire a support person — not a developer.

The Three Hiring Tests

Before posting any job, answer these:

Contractor vs Employee: The Real Difference

Recommendation for first hire: Start with a contractor on a 3-month contract. Evaluate performance. Extend or hire permanently based on results.

Where to Find Great Remote Contractors

Global Platforms

African Talent Platforms

Direct Community Hiring

For many roles, the best talent comes from communities, not platforms:

• Twitter/X DMs to developers or writers you follow
• LinkedIn searches for specific skills + "open to work"
• Slack communities for your specific technology stack
• University groups for junior talent in Nigeria, Kenya, Ghana

Writing the Job Post That Attracts Top Candidates

Most job posts repel good candidates. Here's why:

Bad job post structure:

• Company description (nobody cares until they know if it's relevant to them)
• Vague responsibilities
• Keyword-stuffed requirements
• "Competitive salary" (translation: we don't want to tell you)
• "Fast-paced environment" (translation: chaotic)

Good job post structure:

TITLE: [Specific Role] — [What Makes This Different] — Remote

THE CONTEXT (2 sentences):
We're [what you do] serving [who you serve]. 
We're at [stage] and [one specific exciting thing about this moment].

THE ROLE (3 sentences max):
You'll own [specific outcome], specifically by doing [main activities].
This is different from most [role] jobs because [one specific differentiator].

WHAT SUCCESS LOOKS LIKE IN 90 DAYS:
- [Specific measurable outcome 1]
- [Specific measurable outcome 2]
- [Specific measurable outcome 3]

YOU'RE GREAT AT:
- [Specific skill 1 with context]
- [Specific skill 2 with context]
(Keep this to 4–5 things that are truly non-negotiable)

NICE TO HAVE (but won't rule you out):
- [2–3 things]

WHAT WE OFFER:
- [Specific salary range — always include this]
- [Working hours/timezone expectations]
- [Equipment policy]
- [Other specifics]

HOW TO APPLY:
Send an email to [address] with:
1. Your 2–3 minute Loom video answering: [specific question relevant to the role]
2. 2 examples of relevant work
3. One question you'd ask in an interview

Applications without the video will not be reviewed.

The Loom video requirement filters out 80% of low-effort applicants. Everyone who sends a video is genuinely interested.

The Interview Process

Stage 1: Async Assessment (15 minutes of their time)

A small task related to the actual work. Not a trick. Not a 5-hour project. A 15-minute genuine sample:

• Writer: "Write a 200-word LinkedIn post on [topic]"
• Developer: "What's wrong with this code? [small bug]"
• Support: "Write a response to this customer complaint: [real complaint]"
• Designer: "Describe how you'd approach this design problem: [real problem]"

This tells you more than 10 interviews.

Stage 2: 30-Minute Video Interview

Four questions only:

• "Walk me through your best piece of work in the last 6 months." (Shows what they're proud of and how they communicate)
• "Tell me about a mistake you made and how you handled it." (Shows self-awareness and accountability)
• "What would you want to know about this role before accepting?" (Shows research, thinking, and priorities)
• "What does 'done' mean to you?" (Reveals standard of quality)

Stage 3: Paid Trial Project

Two weeks, paid at their hourly rate, real work. This is not unpaid "spec work" — you pay for their time. But the work is real and you evaluate both output and working style.

What to observe during trial:

• Do they ask clarifying questions or just start without enough context?
• Do they communicate proactively or only when you ask for updates?
• How do they handle unclear requirements?
• Is the quality of work what they suggested in the interview?

Onboarding: The First 30 Days

Week 1 Goals

• They know the tools and have access to everything they need
• They understand the top priority for their first 30 days
• They've met (video call) every person they'll work closely with

Week 1 Checklist

• [ ] All system access granted (email, Slack, Notion, etc.)
• [ ] First project brief written and shared
• [ ] Daily 15-minute check-in call for first 2 weeks
• [ ] One shared document: "What I need to know to succeed in this role"

The 30-60-90 Plan

Define specific, measurable outcomes at each stage:

Managing a Remote Team: What Actually Works

Communication Stack

Rules That Prevent Remote Team Dysfunction

• Default to async — don't schedule a call if a Loom or written message works
• Document decisions — verbal agreements disappear, written ones don't
• Celebrate publicly, feedback privately — never criticise in a group channel
• No ambiguous tasks — every task has an owner, a deadline, and a definition of "done"
• Respond within 4 hours during working hours — this is the baseline expectation

When Things Go Wrong

Performance Problems

90% of performance problems are caused by one of three things:

• The hire was wrong for the role (skills or cultural fit)
• The expectations weren't clear enough
• The person doesn't have what they need to succeed

Before concluding it's a performance problem, ask: "Did I give this person a clear outcome, the tools to achieve it, and feedback along the way?" If the answer to any part is no, fix that first.

The Feedback Conversation

Frame: "I want to share some feedback and I want this to be a two-way conversation."

Observation (specific, not evaluative): "Over the last 3 weeks, I've noticed [specific behaviour/output]."

Impact: "The impact of that is [specific consequence]."

Question: "What's your experience of this? Is there something I'm not seeing?"

Request: "What I'd like to see going forward is [specific change]. Does that make sense?"

Support: "What do you need from me to make that easier?"

This framework — observation, impact, question, request, support — handles 80% of performance conversations without becoming adversarial.