As a coach, I'm always looking to synthesize wisdom on leadership and management from diverse sources into insights to share. In this spirit, today I’ll be exploring guidance on one-on-ones with contractors inspired by the invaluable Manager Tools podcast. Their perspective has profoundly shaped my own approach to effective management.
As a manager, one-on-one meetings represent your most powerful tool for building trust, fostering transparency, and empowering your team. But what about contingent, contract, or freelance workers who are not permanent employees? Should you invest the time and effort to meet with them regularly too? In most cases, the answer is a resounding yes.
They Directly Influence Results and Outcomes
At the end of the day, anyone who does work that significantly impacts your department’s outcomes warrants your attention and relationship-building. Contractors produce key deliverables and services your team relies on to hit targets and achieve success. So taking time to understand their challenges, surface concerns early, and improve collaboration will naturally yield better collective results.
One-on-one meetings exist fundamentally to foster effective, two-way communication and greater understanding between managers and their people. This in turn leads to increased engagement, more nimble problem-solving, higher quality output, and ultimately better performance.
Therefore, don’t view one-on-ones as a “perk” to dole out selectively or exclusively to privileged full-time employees. They simply represent an essential management practice to align the resources you depend on - all the resources - in service of shared goals.
Tailor the Approach Thoughtfully, Not the Overall Principle
When implementing one-on-one meetings with contract teammates, tailor the execution and formatting appropriately without compromising on the underlying commitment to inclusive leadership:
Roll them out simultaneously with permanent employees to signal equal importance and investment in their success, regardless of status. Avoid any visible favoritism.
Use a balanced 15 minute - 15 minute agenda split rather than 10-10-10, since you likely won't have long-term career development and goal-setting discussions. Keep the focus on near-term work.
Establish clear boundaries around inappropriate topics like pay, benefits, promotions, and future career trajectory that should strictly involve their employer, not you.
Focus the bulk of your one-on-one interactions on near-term work deliverables, processes, timelines, and constructive feedback to improve output and results. Content will differ but candor and care need not.
Get to know them as people too - there is no need for impersonal, all-business interactions. Find common ground as fellow professionals even if not under the same legal employment.
At the end of the day, you manage their work output, so take time to proactively manage the relationships enabling that work, rather than just reactively addressing problems as they arise. Delivering this respect and inclusion thoughtfully demonstrates your commitment to leading all team members well, without overstepping legal bounds.
Investing in Consistent Communication Pays Real Dividends
Above all, consider how consistent one-on-one meetings with contract employees establish open flows of communication and opportunities to surface concerns early, before frustrations boil over or issues spiral. This allows both of you to course correct quickly when needed, or capitalize on emerging opportunities in an agile fashion.
You also build relationships where people feel valued as individuals, not just interchangeable contractors. This motivates discretionary effort, knowledge sharing, and willingness to go the extra mile when crunch times inevitably hit.
If you need any guidance instituting more inclusive, empowering one-on-ones, I offer management coaching focused explicitly on relationship-building, feedback excellence, and other core leadership skills vital for unleashing any team’s potential. Please reach out anytime to discuss how we can collaborate. Thoughtful communication and leading by serving will reinvent what your team can accomplish together.