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Master The Flexible Talent Search: Seven Critical Questions To Ask When Building A Competitive On-Demand Workforce Selecting the right independent professional is not just about matching skills to job descriptions though; it is about understanding the individual's potential to contribute meaningfully to the company's culture and the project at hand.

By Azeem Zainulbhai

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In today's rapidly evolving business landscape, the demand for deep expertise has intensified the need for agile and specialized talent. A McKinsey Global Institute survey underscores this trend revealing that 87% of companies anticipate a skills gap, potentially leading to project delays, decreased productivity, and compromised competitiveness. This challenge is particularly pronounced in the high-growth MENA region, where the right talent can make all the difference for long-term project-based work.

Selecting the right independent professional is not just about matching skills to job descriptions though; it is about understanding the individual's potential to contribute meaningfully to the company's culture and the project at hand. To this end, we at Outsized have curated seven pivotal questions that can help companies identify the ideal freelance talent, ensuring they align with the dynamic needs of the business. Here's what they are:

1. UNDERSTANDING AND INTEREST: What do you know about our company and this specific role/project?

This question helps companies gauge the candidate's commitment and research skills, determining if they have thoroughly understood the company's work and culture. A well-prepared candidate will articulate how their skills and experience align with the role, showcasing their potential. This is the difference between someone who would be good at the role versus someone who would be great.

2. ACHIEVEMENT ANALYSIS: What's the biggest highlight of your career in the last two years?

This question allows companies to assess the candidate's ability to discuss past achievements, revealing their honesty, communication style, and involvement in past projects. A smart candidate will tie their learnings into the current role, or how those learnings are beneficial for this project. Responses lacking detail or relevance may indicate a mismatch between the candidate's experience and the job's demands.

3. PROBLEM-SOLVING ABILITIES: Case-study analysis

Case interviews are the ultimate test of problem-solving and communication skills. Challenge candidates with real-world client issues, evaluating their problem-solving, communication, and innovation skills, prioritizing originality and analytical depth. Success here is a strong indicator of a candidate's ability to handle complex project challenges. Candidates who not only demonstrate originality, but also actively engage by asking questions during these rounds, exhibit a candidate's comprehensive grasp of the subject matter, and their adeptness at tackling intricate project dilemmas with acumen.

Example case study questions can include:

  • Imagine our company is planning to expand into a new market with a unique product. How would you conduct market analysis and strategy development to ensure a successful launch?
  • How would you reinvent our digital marketing strategy to boost engagement in regions where our performance has lagged?

Fast fact: originality over standard methodologies significantly influences hiring decisions- 80% in the first round, and 50% in the second.

4. CAREER MOTIVATION: What are you looking to do differently in your next role?

This question provides insights into the candidate's motivations and career aspirations, understanding their career trajectory, and whether their goals align with the company's culture, values, and the role's demands. It differentiates between thoughtfully planned career moves and impulsive decisions, highlighting potential red flags like only money-driven motives or unprofessional attitudes.

5. UNIQUE STRENGTHS: What is your superpower, and how will you leverage it to make an impact here?

Asking about a candidate's "superpower" enables companies to assess how individual talents can enhance team performance and contribute positively to company operations. This inquiry delves into self-awareness, and sifts through generic responses to truly uncover distinctive abilities. It also is a chance to understand how their strengths can influence team dynamics and operational efficiency, providing insights into the candidate's future growth and value to the organization.

6. RESILIENCE AND LEARNING: Describe a significant mistake you made. How did you handle it and rectify the situation?

This question sheds light on a candidate's maturity, resilience, and willingness to learn from their mistakes, offering a glimpse into their problem-solving skills and attitude towards risk and failure. With only 27% of traditional employees showing high resilience, and over a third displaying low levels, it's crucial for company success to find independent talent who can admit weaknesses, take responsibility, and demonstrate problem-solving skills.

7. CULTURAL FIT: What aspects of your previous company's/projects' culture do you wish to bring or avoid in your next role?

This is a great question to evaluate the candidate's cultural preferences and adaptability, as these are crucial for ensuring long-term satisfaction and retention, especially in a flexible workforce. Given Robert Walters' finding that 73% of professionals quit jobs over cultural mismatches, this is key to preventing sudden capability gaps. Candidates should exhibit a learning mindset that aligns with the company's values, rather than solely focusing on negative aspects of past experiences.


In addition to the above questions, companies can consider probing a candidate's approach to remote work or fostering a diverse and inclusive environment. These aspects are crucial in today's global workforce, especially for on-demand talent that often operates in remote or hybrid settings. This will also offer insights into a candidate's self-management skills, which are indispensable in today's workforce settings.

Building a competitive on-demand workforce is about more than just filling skill gaps; it's about finding candidates who can thrive in your company's culture and contribute to its growth in a meaningful way. By incorporating these refined interview questions into your talent search, you can ensure a more holistic evaluation of potential hires. Platforms like Outsized facilitate this process by connecting businesses with a global pool of vetted skilled independent professionals, ready to meet your project's unique needs.

Remember, the right questions can lead you to the right talent, transforming your workforce into a dynamic and agile force ready to tackle the challenges of tomorrow.

Related: Managing Your Modern Workforce In The MENA Region: The How-To

Azeem Zainulbhai is the co-founder and Chief Product Officer at Outsized, a leading talent-on-demand platform for large enterprise clients and consulting firms.

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