The Key Qualities to Look for When Hiring an IT Contractor (Includes Hiring Checklist)
30/09/2025
Navigating the latest technology and web features can help your business stay ahead of the curve. As of 2024, over 25% of business is conducted online, so the importance of managing these features is clear.
In many businesses, contractors play a critical role, not because in-house teams are too expensive, but because the required skills fall outside the company’s core strategy, or because the team needs to scale quickly for specific projects.
Likewise, hiring a permanent team member can sometimes limit a business’s options and flexibility. Many companies are drawn to the added expertise and agility that a contractor pool provides.
Contractors are often expected to integrate seamlessly, sometimes working hybrid or onsite alongside internal teams. But preferences can differ. Some contractors prefer to work 100% remotely, while the client might expect them in the office 2–3 days a week.
That’s why it’s essential to have clear conversations early. Discussing expectations around onsite presence, travel time, and ways of working helps avoid friction and ensures both sides are set up for success.
But how can you find the right fit? What should you be looking for when considering IT contractors? In this article, we’ll detail what you need to know to confidently navigate the IT contractor market. From important skills to professional conduct and hiring checklists, we’ll help you identify the right candidate.
Whether you’re an IT contractor aiming to work smarter or a business in search of proven talent, Umbrella Club connects Australia’s top IT professionals with the companies that value them most.
The Importance of Choosing the Right Contractor
Choosing the right IT contractor can have a significant impact on your business, influencing everything from day-to-day collaboration to long-term performance.
In some roles, communication is critical. You need someone who can clearly explain what’s happening behind the scenes, keep stakeholders informed, and work effectively within your team. In other roles, it’s deep technical expertise that makes the difference, whether it’s solving complex problems, navigating legacy systems, or delivering upgrades with minimal disruption.
Often, it’s a combination of both. A well-rounded contractor brings the right mix of technical skill, adaptability, and collaboration, reducing the need to hire multiple specialists and helping your systems run smoothly, now and into the future.
That’s why working with a pre-vetted professional, someone backed by a trusted peer network, can reduce uncertainty and help you build reliable, long-term partnerships.
The ideal IT contractor has the skills and knowledge to back up their work. They can work with your teams and help you navigate a range of IT problems. Here, we’ll help you identify these different qualities.
Technical Skills: Finding the Right Expertise:
Ensuring your IT contractor has the right skills might be difficult, especially if you lack an understanding of IT services. However, if you can build a minimal understanding of each of these qualities, they will be easier to identify.
Programming Languages and Frameworks
To get the best results, your IT contractor needs to be fluent in the programming languages and frameworks most relevant to your environment. Whether it’s building with JavaScript, maintaining a legacy system, or navigating modern frameworks like React or .NET, the right contractor will have the versatility to work across different stacks.
No two roles or transformations are the same, and neither are the tools required. A strong contractor understands how to choose and adapt the right technologies to suit your goals, ensuring your systems are built to last and easy to evolve. These languages and frameworks aren’t just technical choices, they’re the foundation for scalable, secure, and sustainable delivery.
Certifications and Experience
Ensuring your IT contractor has the right qualifications is a simple way to check that they have the knowledge that you can rely on.
Most IT contractors will at least have a Bachelor’s degree in Computer Science. This demonstrates that they can learn technical skills as well as illustrates the experience they have cultivated throughout their degree. However, real work experience is invaluable and should never be
Likewise, contractors who have different certifications illustrate a commitment to specialised learning. If your IT contractor has these achievements, they likely have valuable learning and adaptability skills.
Niche Skills and Technologies
As technology continues to develop and adapt, so too should IT contractors. Likewise, hiring IT contractors with unique and specialised skills can help your business stand out. For instance, AI is a developing technology that AI experts can use to create useful data management algorithms.
Working with a contractor who’s part of a forward-thinking network, one that stays ahead of emerging trends, ensures you’re not just hiring for today, but building capability for tomorrow.
Communication and Collaboration: Beyond Technical Know-how
While technical skills make up the core of what IT contractors need, additional soft skills are integral to getting great results
Client and Team Communication Skills
An IT contractor’s communication skills are integral to their work. They need to be able to communicate with your team and understand their needs and expectations. Likewise, they must be able to clearly convey what their work entails and how it will affect your business operations.
Without these soft skills, your IT contractor may work on areas you do not want to be touched. Likewise, any changes they make may make operations harder for the rest of your team. The right hire will be able to navigate these communication problems with ease and deliver great results.
At Umbrella Club, communication isn’t just encouraged, it’s expected. Our community is built on peer-driven support, which fosters clarity, shared success, and smarter collaboration.
Adaptability in Different Work Environments
Depending on your needs, your IT contractor should be flexible with different working arrangements. Working from home and collaborating in an office environment are both very different.
An ideal IT contractor should be able to navigate the differences with ease, fitting into your workflow without disrupting it.
Similarly, they need to be able to adapt to different processes and systems. Without this flexibility, they will struggle to make an impact on your outcomes.
Reliability and Professionalism
The right IT contractor should also be professional and reliable to reflect positively on your business. While this may involve personal conduct, there are also key qualities you can identify to ensure they are the right fit.
Meeting Deadlines
IT contractors need to be able to manage projects effectively and meet designated deadlines. A late update could set back your business and cut into your profits. Ensure your IT contractor has great time management skills along with a history of completing projects with specific deadlines.
However, while deadlines are important, sometimes the scope of a project can balloon. When this happens, your IT contractor needs to be able to communicate clearly with you about expectations and delivering results. This can help mitigate deadline issues before they worsen.
Problem-solving Under Pressure
IT contractors should also be adaptable and creative, they need to be able to solve issues. Throughout a project, market factors could change, or assignment problems could develop. Being able to address this quickly, efficiently and effectively can help your business stay on track. Likewise, it can eliminate the need for future IT costs.
That’s why Umbrella Club only connects clients with contractors who have demonstrated excellence and resilience through real-world challenges, backed by references and peer endorsement.
The Hiring Checklist: What to Assess Before Making a Decision
While understanding each of these features is important, it can be difficult to distil them into identifiable skills. Resumes and interviews can help you gain a deeper understanding of your potential hire, but if you are not sure what to look out for, you could miss important details.
Here, we’ll list different checklists you can use when assessing hires to find the right fit.
Technical Assessment
☐ Proficiency in key programming languages – JavaScript, Python, Java, C#
☐ Years of experience
☐ Experience with different frameworks – React, Angular, Node, Swift
☐ Able to navigate mobile frameworks
☐ Unit and integration testing and debugging experience
☐ Experience with Cloud platforms and infrastructures
☐ Understanding of basic security principles – data encryption, authorisation checks
☐ Specialised skills – AI, data analysis, software engineering
Soft Skills Evaluation
☐ Verbal skills
☐ Written skills
☐ Able to adapt to changing situations and responsibilities – do they have a relevant example?
☐ Can work as part of a team
☐ Can give and receive feedback
☐ Self-management skills – time management, task prioritisation
☐ Consistent record keeping – tracking changes
☐ Analytical skills – addressing problems logically
References and Past Project Reviews
☐ Recent references – 2 to 3 years
☐ Confirm role responsibilities and contributions
☐ Check communication history
☐ Assess project relevance
☐ Documented project contributions
☐ Project challenges and solutions
☐ Evaluate short-term contributions and long-term contributions
☐ Check evidence of different technical skills
Making the Right IT Hire for Your Business Needs
There are several factors every business should consider before hiring an IT contractor. With our provided checklists, you can distil these skills and qualities to make them easier to identify. However, the IT industry is complex and constantly evolving.
That’s why Umbrella Club is more than a hiring platform; it’s a partner in your success. We connect you with pre-vetted, proven professionals who are backed by a high-performing community and committed to long-term results.
If you’re looking for a reliable IT contractor who has the skills you need, partner with us to find the right fit.
Walter is the Founder and CEO of Umbrella Club.
He emigrated to Australia in early 2018, bringing with him years of experience building a successful company in the Netherlands. Drawing inspiration from community-based staffing models that had thrived in Europe, he adapted these concepts to fit the Australian market. This led to the creation of Umbrella Club, a unique solution tailored to meet the needs of IT contractors while fostering a strong sense of community.
