Cyber-Ready and Contractor-Wise: The 2025 Enterprise Playbook

Cybersecurity Is the New Litmus Test for Enterprise Trust

Part 3 of Our 3-Part Series Contractor Expectations Series

Contractors today are choosing clients as carefully as clients choose them. And heading into 2025, one of the biggest deciding factors is how seriously an organisation takes cybersecurity.

Our latest State of Contracting report confirms it: data protection is no longer just an IT issue - it’s a major influence on contractor decision-making. When asked about the importance of a client’s approach to information security, contractors rated it 87 out of 100. That’s up there with flexibility, culture, and pay. And it makes sense.

Most independent professionals work across several organisations, often using their own devices and networks. That level of autonomy also introduces risk. From phishing threats to unsecured file sharing, they’ve seen how quickly things can go wrong. Many worry they’ll be seen as the “weak link” if something happens, especially if the company hasn’t provided clear protocols or protective tools.

Cybersecurity: A Deal-Breaker in Contracting

It may not have been on the radar five years ago, but today, contractors rank cybersecurity among the most critical elements of a successful contract engagement.

In a world of escalating cyberattacks, professionals are closely scrutinising how enterprises manage digital risk. Contractors want to know their data—and the data they work with—is safe. And they’re actively choosing to avoid clients who appear unprepared.

Beyond placing a high value on a client’s security posture (87/100), contractors are also carrying their own concerns into assignments. The report showed a 78/100 average concern score around data risks. Many are anxious about breaches, data loss, and unclear boundaries of responsibility if something goes wrong.

The reality is that many contractors operate solo: no corporate IT department to fall back on. They use their own tech, manage their own access, and often juggle multiple clients. Without a strong security infrastructure and clear guidelines from clients, they’re exposed and understandably cautious.

The Key Concerns Contractors Raised:

• Outdated or insufficient internal policies, such as weak access controls or legacy systems

• Lack of investment in protective tools, including VPNs, secure devices, and antivirus software

• Unclear expectations around roles and responsibilities in the event of a breach

• Risky collaboration practices, like unprotected file sharing or unsupported cloud platforms

Contractors don’t expect perfection, but they do expect partnership. That means shared accountability, clear protocols, and a working environment that doesn’t leave them vulnerable.

The bottom line? Strong cybersecurity practices are now a key component of contractor experience. And if your systems aren’t up to scratch, you might be losing out on top-tier talent before you even realise it.

How Enterprises Can Respond

1. Make security a selling point
If your company has solid security measures, don’t be shy about letting contractors know. Include a line in your contract job postings or interviews about the security infrastructure (“We use industry-leading security practices to ensure our team, including contractors, can work safely and securely.”). This signals to candidates that you take it seriously.

2. Provide the tools and access they need
Whenever possible, equip contractors with company-managed devices or secure access methods. For example, if a contractor is handling sensitive client data, providing them a company laptop that’s pre-loaded with necessary security software and VPN access can alleviate a lot of worry. If that’s not feasible, ensure that they can access systems through secure cloud platforms or remote desktops rather than exposing data via unsecured channels.

3. Onboard them on security protocols
When a contractor starts, include a quick orientation on your security policies. Tell them what they should do (e.g. always use the company VPN, use approved cloud storage for files, enable MFA) and what not to do (e.g. don’t use personal email for work files, don’t install unapproved apps). Make it easy: maybe a one-page “Contractor Security Cheat Sheet” with dos and don’ts. Contractors will appreciate the clarity. It also shows that you’re proactive about protecting both them and the company.

4. Establish shared accountability
This one is cultural as much as procedural. Communicate that security is everyone’s responsibility, and back that up by creating an environment where contractors feel comfortable reporting a potential issue or asking for help. For instance, if a contractor suspects a phishing email, they should know exactly whom to alert and trust that they won’t be scolded for it, but rather thanked. And in the unfortunate event of a security incident, conduct blameless post-mortems. The goal should be solving the problem, not scapegoating. When contractors see that approach, it builds trust.

5. Keep security practices up-to-date
Contractors, especially those who bounce between companies, will notice if your tech and practices feel antiquated. Regularly update your software, patch your systems, and stay current with security trends. If you’re lax, word might spread that your company is behind the times or a risky place to work. Conversely, a reputation for strong cybersecurity can become a competitive advantage in hiring contractors (and, frankly, employees too). It’s one more way to show you run a professional, competent operation.

Bottom line: Treat cybersecurity as a partnership between you and your contractors. By investing in strong security measures and actively involving contractors in your security culture, you not only protect your organisation but also make contractors feel safe and respected. In 2025, that can absolutely be a deal-maker for whether a top contractor chooses to work with you or with someone else.

Building a Contractor-Friendly Enterprise

As we’ve seen through these insights, the world of contracting in 2025 comes with its own set of expectations and opportunities. For enterprise organisations, the message couldn’t be clearer: if you want the best contract talent, you need to meet contractors where they are in terms of flexibility, culture, technology, and support. The days of treating contractors as interchangeable stop-gaps are over. Today’s contractors are looking for mutually beneficial partnerships, not just transactions. They expect to be treated as valued professionals who bring critical skills to your organisation (because they do!).

To wrap up, let’s summarise what enterprises should do about these insights in practical terms:

• Embrace Hybrid Work Norms: Make flexible work arrangements your default. Set up your policies and infrastructure to support remote and hybrid contractors. By doing so, you cater to the 64% who prefer hybrid setups and demonstrate trust in your talent. This will widen your talent pool and keep contractors happy and productive.

• Prioritise Flexibility & Autonomy: Structure contracts and projects to allow some freedom in how the work gets done. Focus on outcomes rather than micromanaging hours. When contractors feel trusted to manage their time and methods, they’re more engaged. Remember, flexibility was ranked the #1 value for contractors—honour that, and you’ll be a preferred client.

• Offer Competitive Pay and Purpose: Don’t rely on a paycheck alone to attract talent (though it should be fair!). Highlight aspects of the work that bring purpose or growth. For instance, if a project has a meaningful impact or uses innovative tech, make that known. Contractors are increasingly purpose-driven and looking for fulfilment alongside pay. Show them they’ll find it with you.

• Integrate Contractors into Your Culture: Welcome contractors as part of the team. Communicate openly, include them in relevant meetings, and give feedback just like you would with any team member. Also, ensure a smooth onboarding—it’s a simple thing that speaks volumes about how you operate. Contractors value a culture of transparency, collaboration, and ethical leadership, so cultivate that environment. When contractors feel respected and included, they’re more likely to go the extra mile for you (and to come back for future contracts).

• Invest in Tools and Tech (like AI) that Empower: Provide access to the latest productivity tools—whether that’s AI software, project management platforms, or other tech relevant to the role. If you expect contractors to use new tech, offer guidance so they can hit the ground running. This not only boosts efficiency but also signals that you’re an innovative organisation. Contractors largely see AI as a positive tool, so help them leverage it, and you’ll both reap the benefits.

• Double-Down on Cybersecurity and Trust: Make your security protocols rock-solid and make sure contractors know it. Have clear policies, share them, and provide the necessary secure tools (like VPNs or secured devices) for contractors to do the job safely. Given that many contractors worry about data security, addressing this upfront builds trust. In practice, this could mean briefing contractors on security in onboarding, giving them a point of contact for any security questions, and fostering a no-blame culture around security issues. A contractor who trusts your systems is one who can focus on delivering great work instead of looking over their shoulder.

• Treat Contractors as Long-Term Partners: Even if a contract is short-term, think long-term in how you treat people. Provide honest feedback and ask for theirs. Keep in touch with high performers for future gigs. If you can offer some continuity (like first dibs on a contract renewal or next project), do it. Contractors notice which companies value their contributions and career. Those are the companies they prioritise working with. As the report noted, contractors want transparency, honest communication, and fair treatment—they want to be seen as partners, not just resources. If you can build that kind of relationship, you’ll have a reliable network of go-to contractors who are eager to work with you again and again.

  
  

Work in 2025 is all about flexibility, mutual respect, and smart adaptation. Enterprise organisations that understand what 550+ contractors have told us hybrid work is expected, flexibility and autonomy are king, culture and communication matter, AI is a tool to embrace, and security cannot be overlooked - will be the ones best positioned to attract top talent in the contractor market. By acting on these insights, you’re not just checking boxes to keep contractors content; you’re building a more agile, innovative, and resilient workforce for your own business.

Let’s Take Action

Cybersecurity isn’t a checkbox - it’s a pillar of trust in the contract workforce.

Want to know how your contractor experience stacks up? Let’s assess your model for security, flexibility, and trust.

Talk to Oncore today.