How to Hire the Right Contract Instructional Designer: A Smarter Checklist for L&D Leaders

Hiring a contract instructional designer can feel like a fast way to get learning projects moving, but the true advantage comes when you bring in someone who can elevate the work, not just execute it. 71% of L&D leaders struggle to hire instructional designers with the right mix of skills and experience.

Whether you are building a foundational technical course or refining leadership development modules, finding the perfect instructional designer can feel like searching for a needle in a haystack. The challenge is not just about technical expertise, it is about finding someone who combines creativity, learning psychology, and project management skills to enhance the learner’s experience and align training with your business needs.

With so many freelancers on the market, how do you know who is truly qualified? What separates a dependable contributor from someone who can help drive measurable outcomes?

Let’s walk through a framework that experienced L&D leaders use to make strong hiring decisions, plus a checklist of criteria to keep close as you evaluate candidates.

Why Hiring the Right Contract Instructional Designer Matters

Instructional designers are often the backbone of your learning initiative. They do not just build content—they translate strategy into learner experience. The challenge? The freelance economy is booming. In fact, 64 million Americans freelanced according to Upwork, and the L&D freelance market has grown by more than 50% since 2020, based on Training Industry research.

This increased access to freelance talent can be a major advantage, but it also introduces risk. The difference between an average contractor and a strategic partner can make or break timelines, budgets, and even the credibility of your training function.

First, Define What Success Looks Like

Before you begin reviewing portfolios or writing a job description, pause to clarify what your project requires. Instructional design is not one-size-fits-all, and skipping this step can lead to costly mismatches in skills, style, or scope.

Start by outlining what success looks like for your learning initiative. That includes asking:

• What specific knowledge or skills need to be developed?
• What should learners be able to do differently as a result?
• Who is the training for, and what are their learning preferences or constraints?

This clarity not only informs the job scope, but it also shapes how an instructional designer will structure the content itself. If your learners are distributed field teams with limited time, you will want someone who can design efficient, mobile-friendly microlearning. If you are training on a new internal system, you will need an instructional designer with technical fluency and the ability to work closely with SMEs under tight timelines.

Consider developing learner personas—representative profiles that capture the real-world context, habits, and challenges of your target audience. This gives your contract instructional designer a stronger foundation for aligning tone, pacing, modality, and interactivity.

Finally, involve stakeholders early to validate learning goals and ensure they tie directly to business needs. A beautifully designed course that does not support measurable outcomes will fall short, no matter how polished it looks.

What to Look For: Five Key Traits That Matter

Here are five traits to assess when evaluating contract instructional designers. These go beyond resume buzzwords and get to the heart of what makes someone effective in real-world L&D environments.

1. Industry experience that aligns with your environment
   Context matters. An instructional designer unfamiliar with your industry may miss nuances that affect everything from tone to compliance.

• • Have they supported initiatives in regulated sectors like healthcare, finance, or insurance?
  • Do they understand the constraints and challenges specific to field-based or customer-facing roles?

2. Fluency across modalities and tools
   Look for versatility. Whether you are using Storyline, Rise, or designing for virtual ILT, they should be comfortable navigating multiple formats.

• • Can they design for both digital and instructor-led environments?
  • Are they skilled in the tools your team or LMS relies on?

3. Evidence of impact, not just output
   Strong instructional designers should be able to articulate how their work made a difference.

• • Can they share outcomes, metrics, or performance improvements tied to their content?
  • Do they have client feedback, evaluations, or data that demonstrate effectiveness?

4. Soft skills and a collaboration mindset
   Even the most talented instructional designer will struggle if they cannot communicate with SMEs, project managers, or stakeholders.

• • Do they ask clarifying questions during intake?
  • Are they comfortable giving feedback or navigating ambiguity?

5. Knowledge of learning science
   This is what separates a content creator from a learning strategist. Great instructional designers understand how adults learn—and why that matters.

• • Can they justify their design choices based on instructional theory or learner behavior?
  • Do they focus on knowledge transfer and behavior change?

Beyond the Checklist: Assessing Strategic Thinking

It is one thing to check off tools and technical skills. But what truly sets apart a high-performing instructional designer is how they think. Strong designers see the bigger picture. They understand business drivers and can connect training back to performance.

Ask questions that reveal how they’ve:

• Led or contributed to a needs analysis
• Collaborated with stakeholders to align content to goals.
• Adjusted strategies midstream based on learner feedback or constraints.

You are looking for signs that they can flex with the project, not just follow directions.

The interview stage is your best opportunity to make this distinction. This is where you separate candidates who speak well about design from those who can drive learning impact. Come prepared with a structured approach, not just a conversation. Develop scenario-based questions that let candidates demonstrate how they approach real-world challenges, not just describe their skills.

Ask them to:

• Walk through a project where they had to pivot midstream due to stakeholder input or learner feedback.
• Share a time when a course did not meet expectations, and how they diagnosed and addressed it.
• Share how they navigate partnerships with SMEs who are stretched thin or focused on other priorities.

Structured interviews help you cut through polished resumes and get a clearer picture of how someone works under real-world conditions.

Fit Is More Than a Buzzword

When a contractor seamlessly integrates with your team, things move faster. Communication flows better. Feedback loops are tighter. You need someone who feels like a natural extension of your internal L&D function.

That kind of fit shows up in subtle ways:

• Are they proactive with communication?
• Do they adapt to your team’s style and tools?
• Are they curious, not just about the content, but about the context behind the project?

When you find someone who hits the right balance of skills, style, and strategic mindset, the partnership tends to expand naturally, sometimes across years and multiple projects.

What Seasoned L&D Leaders Do Differently

Many experienced L&D leaders use a structured selection process that goes deeper than resumes and portfolios. Here are a few practices worth adopting:

• Use real-world scenarios during interviews. Ask candidates to walk through a project and explain their design decisions.
• Evaluate alignment with business goals. Assess their ability to turn vague stakeholder input into measurable learning objectives.
• Check references with intention. Ask about how they handled ambiguity, managed feedback loops, or helped salvage a difficult initiative.

These small shifts create a higher standard for talent and better learning outcomes overall.

Final Thoughts: From Role Clarity to Learning Impact

Hiring the right contract instructional designer is one of the most important decisions L&D leaders make to ensure learning success. When done well, it sets the tone for every learning deliverable that follows.

It starts with clarity on goals, audience, and business alignment. It is strengthened by structured interviews that assess more than software skills. And it is reinforced by a consistent process that evaluates communication, adaptability, and strategic thinking.

The right designer brings structure to ambiguity, connects learning to performance, and collaborates seamlessly across roles. With the right approach, you can build a trusted bench of talent that elevates the quality, reach, and relevance of your learning programs.

Want to go deeper?

Listen to Instructional Design Strategies for Organizational Growth, an episode of our podcast, Bring Out the Talent, featuring Dr. Kate Hixson. Tune in here for practical insights on engaging learners, scaling teams, and using AI in instructional design.

Looking for the right fit? Request your next instructional designer through TTA Connect and align the right expertise to your next learning initiative.