How to Set Independent Talent Up for Success (Guide)
15 MIN
This guide covers best practices for a company and its managers to set up their independent talent for success. These practices are part of building an optimized workforce. It also includes self-assessments that help identify what’s working and where improvement is needed.
GATE
Introduction
The U.S. business environment is entering an exciting phase as new ways of working have taken root. The COVID-19 pandemic challenged long-held beliefs about optimizing productivity in the workforce and opened the door to a variety of work style options for employees and contractors. While some enterprises have moved back to the pre-pandemic work style—or at least attempted to—others are adapting. They are initiating or expanding remote work policies, accommodating digital nomads, and laying the groundwork for workforces that include both full-time employees and independent professionals.
An optimized or blended workforce is the winning strategy for many enterprises across all sectors. The competitive benefits of a workforce that includes a significant percentage of independent talent working alongside employees include operational cost savings, increased productivity, and access to skills not readily available on the job market.
The total number of full-time, part-time, and occasional independents rose to 72.7 million in 2024. This diverse independent population enhances flexibility, enabling hiring managers to fill short-term and long-term roles with expert contractors.
Having access to such a large talent pool is one thing: Setting yourself up for success means engaging the right independent professionals and motivating them to re-engage with you over time.
How well does your organization, and you as a manager specifically, create an environment that supports the success of high-value independents and motivates them to continue their engagement?
Best Practices As an Enterprise
How hard is it to find a contract role at your company? Is there a clearly defined page on your website to find opportunities and submit proposals? Or does your company use a talent network or online marketplace? Once a manager has identified someone they want to hire, how streamlined is the vetting process? How long does it take for the contractor to get to work? Is the work fulfilling for them?
Setting up your independent talent for success begins with the right processes, technologies, and strategies across the enterprise. Review these five best practices and use the self-assessment template provided below to note how your company stands with each. This can help you create a plan to help set up you and your independent talent for success.
1. Engage the Right Talent
Setting your independent contractors up for success starts with having the right talent in the right role. Mastering this practice makes a big difference in your team’s productivity and project outcomes. These tips can help you get started:
- Put a talent network in place
Implementing a talent network is an effective strategy for proactively sourcing and managing groups of highly qualified independent talent. This pool of vetted on-demand independent professionals enables hiring managers to directly source candidates for project roles across the enterprise and serves as an excellent resource for shortlisting talent for future projects. - Use marketing principles to attract talent from outside the network
Your talent network is not static. As your enterprise grows and adapts to changing markets, your talent needs will similarly change, so you’ll need to attract new talent on an ongoing basis. Create one or more campaigns targeting independents with necessary skill sets, using social media, content marketing, email, webinars, or live chat sessions. - Implement policies that address independent work styles
Along with mitigating risk for the enterprise, certain policies can help make it easier for independent talent to determine if their work style aligns with your company and clarify what will be expected of them. We recommend implementing policies such as a remote work policy, a digital nomad policy, and a cybersecurity policy that covers work done on contractor devices. - Offer a variety of compliant engagement options
Because independent contractors operate as their own businesses, they cannot be treated like traditional employees and must be classified according to IRS regulations. While it’s important to put a process in place to ensure all independent workers will be properly classified, their working situations are not “one size fits all.” Independent contractors have different levels of self-employability as well as individual needs and requirements. Providing flexible engagement options will help your organization attract and retain high-value talent while remaining compliant. - Review insurance requirements
The type of insurance a contractor must have will vary depending on their role. Check with your company’s legal advisor about which type of insurance an independent contractor requires. At a minimum, consider requiring general liability insurance.
2. Clearly Define Deliverables and Scope
The completeness and clarity of your contractor engagement has a significant impact on the quality of the work and the results you achieve. Taking the time to go beyond standard templates and documents is essential for setting up your talent for success. Keep these tips in mind to make this practice most effective:
Tailor your standard contract for each independent professional
A written contract outlines the independent professional’s role, the type of work they will be responsible for, and the general terms and conditions required to do business together. Use the contract to define your ongoing engagement rather than to focus on a specific project—the scope of work will be the best place for these details. Start with a standard contract template and work with your talent to add or modify it to fit a particular engagement. A good collaboration can help set the groundwork for a positive working relationship as you work through items like terms of engagement, project resources, and confidentiality commitments.
Use a scope-of-work template and modify it on a project-by-project basis
The scope of work—or SOW—defines the details of a specific project. Elements of the SOW include budgets, timelines, milestones, and deliverables. Again, start with a standard template and enter the details as thoroughly as possible.
Make scope changes as easy as possible to put into place
The procedure for making scope changes should be detailed in the contract and can be repeated in the scope of work. It’s beneficial to make the change process simple and efficient. Just be sure to capture the right information so you’ll have all the proper documentation.
3. Ensure That Onboarding Is Fast and Efficient
The onboarding process generally involves these steps:
- An independent contractor filing a compensation or disability claim
- An independent contractor filing for unemployment compensation
- A whistleblower reporting worker misclassification
- Dual classification
A significant part of the process can be automated, and most if not all of it can be accomplished online. You can implement technology and tools with the right capabilities and hire third-party services for steps like background checks and enterprise-mandated training courses. The benefits to you and your talent include smoother onboarding and the ability to easily and accurately track completed actions.
Talent re-engagement should be easy to accomplish, for you and for your contractor. It may be as simple as creating a new scope of work for both of you to sign.
4. Make Payment Processing Easy
A fast and efficient billing and payment process can greatly support your talent’s success. This is another area where automation is valuable. Online invoice submission is extremely useful to your contractors as it minimizes the time necessary to tender bills. Ensure accurate terms are entered into the system, so your independents are paid promptly according to their contracts.
5. Define Communication Channels
“Communication is key” when it comes to achieving success in managing people. While this is particularly important when it comes to your independent contractors, there are many modes of communication in a business. Many of these are manager-specific and are discussed below.
On an enterprise level, channels that suit different communication forms can greatly enhance productivity, primarily due to time savings. For example, an email platform such as Outlook is a ubiquitous form of messaging, while Slack and Microsoft Teams allow for fast, real-time chat between team members and others in the organization. Meanwhile, online collaboration spaces like Google Docs and SharePoint let people embed comments and conversations directly within a shared document.
Enterprise Assessment to Identify Strengths and Weaknesses
This self-assessment is an opportunity to take some time to consider where your enterprise stands regarding these best practices. Called a “spider diagram” for its likeness to a spider web, one practice sits on each of the five points. The levels of effectiveness range from 1 (doesn’t exist or is ineffective) to 5 (highly effective).
Consider each best practice and assign a score for each, then connect each point with a line. This should result in a visual representation of how well your enterprise is situated to support the success of your independent talent. Using your self-assessment can help you plan and prioritize initiatives to improve enterprise effectiveness.
Download the enterprise self-assessment template
Best Practices As a Manager
The extent of your interaction with your contractor will likely depend on the nature of their engagement. At one end of the spectrum, you may engage them for a short-term project with straightforward deliverables. On the other hand, you may be bringing them on board for a long-term and complex project. The closer you are to the latter, the more significant your management approach becomes. Regardless of where you fall on this spectrum, your support is essential. Each practice is connected to communication in some form—back to that all-important “communication is key” assertion. The more effective you are at each practice, the better you’ll set your talent and team up for success.
1. Build Rapport
Rapport is crucial in any great working relationship. Sharing common interests with others instantly forges a connection. A strong rapport cultivates a motivated and productive work environment.
Before you engage an independent contractor for the first time, review their background to see if any items resonate for you. Details such as schools attended, hobbies, and volunteer work are examples that could serve as excellent conversation starters. Also, spend time talking with them and asking questions about anything that piques your interest.
Keep in mind that independent professionals are business owners who have goals they wish to achieve, including the growth of their business. Talking to them about business or the skills they offer clients can go a long way towards building rapport.
2. Receive Periodic Updates
Set up a formal update milestone. The timing will depend on the project and the contractor’s specific role. In some cases, once a month or biweekly may be ideal, while in others, weekly or even more frequently might be preferable. You can request a live update or simply ask for the information via email. One obvious benefit is that you’ll be able to stay up to date with their projects. A more subtle benefit is the sense of connection you will both feel, which helps keep the work interesting and productive.
3. Have Regular 1-on-1 Meetings
Regular 1-on-1 meetings can produce a high return on investment in your independent contractors. These meetings provide an opportunity to highlight successes, discuss challenges, offer feedback, and ultimately build a stronger relationship. The frequency of your 1-on-1s will depend on the nature of the engagement. At a minimum, have one at the start and one at the end of the project. When it comes to the meeting agenda, create a general outline and then ask your contractor to provide further recommendations. Let them take the lead in the discussion while you ask questions and address any concerns they may have.
4. Give Feedback and Coaching
Provide useful feedback to your contractors, going beyond the notion of feedback as strictly “corrective.” While it’s important to identify any necessary improvements, it’s equally crucial to acknowledge a job well done and highlight what’s working. With the rapport you’ve built, your feedback will likely help your contractors in their own businesses and with other clients.
Coaching is also key, but it’s different from the type you’re giving your full-time permanent employees. Independent talent, especially those who are new to your organization, will need education about navigating processes and procedures as well as your organization’s unique culture. Empower them to get up to speed on “the way things work around here,” and you will likely have a contractor who is well set up for success!
5. Solicit Feedback
Soliciting feedback from high-value independent talent can be highly constructive. Your contractors may be in an excellent position to see where you can make improvements to processes and other activities. These meetings are an opportunity to build rapport and discuss any challenges they are facing. Active listening can provide you and your team with valuable information. Ask for feedback during your 1-on-1s or as part of your periodic updates (or both).
Self-Assessment to Gauge Your Effectiveness
This self-assessment can provide insight into how effective you are in your working relationship with contractors. Called a “spider diagram” for its (very) rough likeness to a spider web, one practice sits on each of the five points. The levels of effectiveness range from 1 (I don’t do this or I’m ineffective) to 5 (I’m highly effective). Consider each best practice and assign a score for each, then connect each point with a line. This should result in a visual representation of how well you are supporting the success of your independent talent. Using this as a guide can help you decide where you want to improve your contractor interactions.
Download the manager self-assessment template
Setting your valued independent talent up for success in 2025 is a win for everyone. With the inclusion of contingent labor in an optimized workforce and the development of successful working relationships, the potential for business growth—both for the enterprise and for your independent talent—is significant.
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