How to Hire Well: A Founder’s Guide
Hiring is one of the most critical skills for any founder. Get it right, and your company takes off. Get it wrong, and you spend months (or years) fixing costly mistakes.
Why Hiring Well Matters
As founders, our businesses are only as good as our teams. Hiring isn’t just about filling roles; it’s about setting the foundation for your company’s culture, performance, and future growth. Bad hires are expensive, not just in dollars, but also in lost momentum, cultural damage, and lack of execution. The earlier you get this right, the better.
The Three Key Hiring Stages
From our experience coaching founders and scaling startups, hiring needs shift as companies grow. We see three major hiring phases:
Your First 10 Hires: These people set the DNA of your company. You need versatility, alignment with your mission, and a deep commitment to building from the ground up.
Building Beyond Your Network (10-50 Employees): At some point, your friends-of-friends pipeline runs dry. This is when process and structure become essential.
Hiring Executives & Scaling (50+ Employees): Bringing in leadership that can manage teams. scale operations, and hire independently requires an entirely different approach.
Common Hiring Pitfalls
Many founders struggle with hiring because they:
Hire based on resumes: A polished resume doesn’t always translate to real-world skills. Relying on work samples, trial projects, or practical assessments can reveal more about a candidate’s actual abilities. In the early stages, it often works to sign a short-term contract for a specific project as an extended trial period.
Avoid tough conversations and keep poor performers too long: Letting underperformers linger because of your own discomfort or optimism drains morale, slows the team, and creates hidden costs. Addressing issues early saves time and frustration.
Overpay or underpay, leading to long-term resentment or churn: Competitive, fair compensation is key to retention. No matter how much you tell them compensation is private, people will talk.
Focus too much on skills and not enough on chemistry and culture fit: A highly skilled hire who clashes with your team’s values can do more harm than good. Especially at the beginning, you really have to like these people.
Fail to create a structured hiring process, leading to inconsistent results: A clear, repeatable hiring framework improves decision-making, reduces bias, and helps scale hiring effectively.
Let’s Build Great Teams
Hiring well isn’t just a nice-to-have; it’s a fundamental skill for building a successful company. Over the next few months, we’ll share insights, strategies, and proven frameworks to help you hire smarter. Stay tuned!