Contractor Cuts

When Should I Hire?: The Chicken or The Egg Problem


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Is it better to hire when you're swamped with work or to bring someone on board proactively? This question haunts many contractors, and today on Contractor Cuts, we promise to help you find the answer. Join us as we weigh the pros and cons of both hiring strategies, backed by our extensive coaching experiences and real-life examples. You'll walk away with a handy checklist to help you decide the best time to expand your team without sacrificing your business's financial health.

Rushing to hand over significant responsibilities to new hires can be tempting, especially under client pressure. But are you setting them up for failure? We'll share personal stories that emphasize the need for structured training plans, even if it means short-term sacrifices. Learn the strategies that ensure new employees are well-prepared, ultimately contributing to your long-term success without putting your business at risk.

Due diligence in hiring is non-negotiable, and skipping it can lead to costly mistakes. We recount a sobering tale of bypassing thorough background checks and the resulting challenges. This episode underscores the importance of a financial runway and a structured hiring process. From crafting comprehensive job descriptions to setting clear accountability standards, we'll provide practical tips for evaluating candidates effectively. Don't miss this essential guide to growing your contracting business sustainably.

Join us January 11–13 in Nashville for the Chart the Course 2026 Planning Retreat. Sign up now and get three free coaching sessions before the event to finish 2025 strong and hit 2026 with a clear game plan. At the retreat, you’ll tackle systems, hiring, marketing, and leadership alongside ambitious contractors, leaving with a blueprint for growth. Spots are limited—visit prostruct360.com to learn more!

Have a question or an idea to improve the podcast?
Email us at [email protected]

Want to learn more about our software or coaching?
Visit our website at ProStruct360.com

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Contractor CutsBy ProStruct360

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