In this episode, Karla Singson pulls back the curtain on how outsourcing really works: beyond the hype, beyond the buzzwords, and beyond the unrealistic expectations many founders have when they hire their first remote professional.

Karla takes you behind the scenes of Proximity Outsourcing’s systems, explaining why most outsourcing relationships fail not because of skill issues, but because of poor onboarding, unclear expectations, and zero communication structure. She breaks down the exact processes, forms, scorecards, and communication frameworks that have helped hundreds of founders scale faster, manage less, and avoid the classic “VA nightmare” stories that flood the internet.

Whether you’re hiring your first remote professional or scaling your 10-person offshore team, this episode gives you the mindset and infrastructure needed to make outsourcing work smoothly from Day 1.

In this episode, you’ll learn:

• Why onboarding determines 70% of your success with an outsourced hire How most companies skip this step entirely, and how Proximity structures it so both sides hit the ground running.

• The three documents that make or break your hire:

  • The Job Description + Success Metrics

  • The Client Chemistry Form

  • The Customer Avatar Form

  Karla explains how each one prevents misalignment, misunderstandings, and unnecessary headaches.

• How to set deadlines realistically, and why most founders unknowingly set their RPs up to fail Plus: When to use time-tracking tools and when to absolutely avoid them.

• Why urgent tasks need explicit communication, not just a Trello card drop And how to insert surprise tasks without destroying your RP’s workflow.

• How to give clear instructions that produce better results with less back-and-forth Karla shares simple tweaks, like using Loom, giving templates, and describing the “ideal outcome,” that instantly improve output.

• The real role of your CSM (Client Success Manager) They’re not just support; they’re the advocate for both you and your remote professional. Karla explains how they can prevent issues, fix problems before they escalate, and save your relationship with your hire.

• Why positive reinforcement works better than pushing harder, especially with Filipino professionals Karla explains cultural nuances many Western founders miss, and how small acts of acknowledgment lead to massive loyalty and performance.

This episode is quick, practical, and built to help you avoid the common pitfalls founders face when outsourcing for the first time. If you want your hire to feel aligned, supported, and successful, instead of confused, overwhelmed, or underperforming, this is the episode to listen to.

Listen now on Spotify: https://open.spotify.com/RichandRemote

Follow Alex and Karla:
Alex Booth: LinkedIn: Alexander Booth - Huckleberry Consulting | Facebook: GetCSM
Karla Singson: Instagram: @karlastefan | Facebook: Karla Singson | LinkedIn: Karla Singson

Big thanks to our sponsors ​Proximity Outsourcing​,

• (00:00:01) - Remote Rockstars
• (00:02:29) - Onboarding
• (00:05:36) - 5 tips for task management on Outsourcing
• (00:08:23) - What is a CSM and Do Filipinos Need Them?