Why One-on-Ones with Contractors Make Sense

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.

How to Schedule One-on-Ones for Maximum Impact

One-on-one meetings are a cornerstone of great management. But with packed calendars, it can be challenging to find time for meaningful connections. Proper scheduling is key to making one-on-ones work. Follow these strategies to set up a cadence that demonstrates your team is a top priority.

I learned the importance of dedicated one-on-ones from an influential mentor of mine who followed the wisdom of Manager Tools, an invaluable resource for leaders. Now I pass on their guidance to help managers develop critical relationship-building skills.

While demands press in, one-on-ones create essential space to guide employees, exchange feedback, and foster growth. Done right, they boost trust, morale, and performance.

A 4-Step Process for One-on-One Scheduling

Scan your calendar first. Block off times for standing meetings and other commitments. One-on-ones take precedence as your most important meetings.

Offer at least 1.5 times slots as you have direct reports. Don’t just provide the exact number of slots - you need wiggle room.

Allow employees to choose the best time for them from your provided options. This demonstrates you value their needs.

It’s okay to request 1-2 time changes if certain slots end up overbooked. But overall, defer to employee preferences.

This balanced approach enables you to steer the ship while empowering your team to find optimal timing.

Key Considerations For One-on-One Scheduling

While there’s no single perfect way to schedule one-on-ones, keep these factors in mind:

Avoid Monday mornings and Friday afternoons due to common conflicts.

Earlier in the week allows more flexibility to reschedule if needed.

Standard meeting times tend to work better than off-times.

Morning, mid-day or afternoon slots have pros and cons - choose based on your and your team’s preferences.

Scheduling them all in one day provides focus, while spreading them out increases flexibility.

Some like back-to-back scheduling for efficiency while others prefer breaks between.

The priority is establishing consistent touchpoints, not finding an elusive ideal time. Test different approaches to see what works best.

The #1 Rule: One-on-Ones Are Sacred

Above all, once you commit to scheduling one-on-ones, make them a firm calendar commitment. Never cancel without immediately rescheduling. Defy attempts by others to schedule over this sacred time with your team.

Making one-on-ones a consistent presence demonstrates their immense value to your employees. It also reflects clear priorities on your part as a manager and enables the trust-building relationships that motivate great work.

Invest in Your People and Your Leadership

By dedicating time for one-on-one meetings and actively listening during them, you develop your team and strengthen your own emotional intelligence and coaching abilities.

If you want additional support for your management journey, executive coaching provides immense value. We can work together to refine your one-on-one approach and other leadership practices. Please feel free to reach out if you would like to explore coaching for yourself or your team. Developing leaders develop their people.

The Power of One-on-One Meetings: A Key Tool for People Leaders

As a manager, few things are more important than building strong relationships and trust with your team. But it’s easy to get caught up in the endless cycle of tasks and meetings, with little time left to connect. That’s why the most effective leaders consistently make one-on-one meetings a priority.

I first learned the power of dedicated one-on-ones from a director I worked for years ago. He structured our meetings based on guidance from the invaluable Manager Tools podcast, which has shaped my approach as a coach. Now I pass this wisdom on to help other leaders develop critical management skills.

While meetings proliferate and time disappears, one-on-ones provide consistent space to listen, exchange feedback, provide guidance, and demonstrate each employee’s value. Done right, they transform relationships and results.

Why One-on-Ones Are Essential

It’s tempting to view one-on-one meetings as just another item on your endless to-do list. But they offer immense benefits that impact your team’s performance and morale:

- Develops trust and stronger connections from quality focused time together

- AllowsSurfacing concerns early before they become major problems

- Provides a regular forum for delivery of praise and constructive feedback

- Keeps you closely in touch with the status of projects and any roadblocks

- Creates a space for brainstorming solutions and providing coaching

- Demonstrates the employee’s importance by giving them your undivided attention

Without regular one-on-ones, you miss critical opportunities to provide clarity, resolve issues early, and guide your employees’ growth and development. Don’t let the urgent undermine time dedicated to understanding your team.

How to Structure Effective One-on-One Meetings

To maximize the impact of one-on-ones, Manager Tools recommends this simple but powerful structure:

- Schedule them for 30 minutes once a week with each direct report

- Block them on your calendar to preserve the sacred time

- Give employees the first 10 minutes to talk about anything on their mind

- Use the next 10 minutes to address your agenda and questions

- Spend the final 10 minutes on coaching and discussing future goals

- Hold them in your office or a neutral space with no distractions

- Never cancel without rescheduling that same week – they are a top priority

This format enables your team to share ideas and concerns freely, knowing they have your full attention and support. This transparencybreeds loyalty and innovation.

Making One-on-Ones More Natural

At first, one-on-one meetings may feel awkward as you develop rapport. Here are some tips to help the conversations flow:

- Ask thoughtful, open-ended questions and listen deeply

- Focus on understanding, not immediately solving problems

- Share your own relevant experiences to find common ground

- Follow up on action items week-to-week to provide continuity

- Note key points and summarize conversations to show you were listening

- Find informal spaces like coffee shops to vary the scenery

As you learn about your employees’ needs and build understanding, the meetings will become more relaxed and valuable.

Why Investing in One-on-Ones Pays Off

Consistent one-on-ones clearly demonstrate that developing team members is a top priority for any great leader. The benefits include:

- Employees feel valued, heard, and invested in

- You gain critical insights into morale, challenges, and goals

- It keeps you connected to the team’s real experience day-to-day

- You strengthen coaching skills through practice and repetition

- Trust increases as people know they have direct access to you

- You quickly address frustrations before they become problems

- It allows recognition of achievements that might otherwise go unnoticed

- Your whole team gains confidence in your leadership and concern for them

By spending time in one-on-ones listening, learning, and connecting, you empower your staff to grow and do their best work. You also build vital management and communication abilities that make you a stronger leader.

Taking Your Leadership Development to the Next Level

While I firmly believe one-on-ones are a foundational management practice, executive coaching can provide immense value in augmenting your skills. Coaches work with leaders to:

- Set up scheduling systems and one-on-one best practices

- Develop strong listening and empowering feedback skills

- Learn to provide guidance while maintaining autonomy

- Improve executive presence and leadership communication

- Implement ongoing methods for relationship-building and mentorship

Everything rises and falls on leadership. Developing yourself is the highest-yield investment you can make, both for your own growth and to inspire your team to bring their best.

I encourage you to check out the Manager Tools podcast and community for more wisdom that has shaped my approach to management excellence. And please feel free to reach out if you would like to explore executive coaching for yourself or your leadership team. Helping leaders grow and serve their people well is my passion.