Expert tips for mature jobseekers: A career coach addresses the 5 most asked questions

Navigating job hunting in the AI age can be daunting, especially for mature jobseekers.

You haven’t updated your resume in years, and your job interview is a distant memory.

Furthermore, having to plough through the multitude of job portals and career resources, as well as numerous AI tools like ChatGPT and Deepseek for resume creation can be overwhelming.

According to a poll released by professional networking platform LinkedIn in January 2025, about six in 10 workers found that the job search process had become more challenging.

The survey with over 1,000 Singapore workers showed that the most frequently reported issue was finding a job that matched personal criteria. This was followed by negotiating salary and benefits and making the job application stand out from the crowd.

Meeting employers’ evolving hiring standards is another common challenge.

Half of the 500 hiring professionals LinkedIn polled said it has become more difficult to find qualified individuals in 2024. Employers revealed that only 3.4 per cent of applicants made the required and preferred qualifications for a job opening.

If you’re struggling with the job hunt process and changing hiring expectations, consider seeking the expertise of NTUC’s e2i (Employment and Employability Institute) career coaches like Sandra Sim. They possess a wealth of experience to make the process more effective and less overwhelming.

The past six months has seen Sandra meeting many jobseekers from the manufacturing and tech sectors. Manufacturing workers are typically laid off due to increasing adoption of AI and the outsourcing of cheaper labour overseas. Meanwhile, tech executives are often displaced due to the industry’s pivot to leaner, more agile workgroups and cautious technology adoption.

The Labour Movement Annual 2025, which outlines NTUC’s achievements and efforts for 2024, stated that e2i facilitated over 29,000 successful job placements during the year.

In this article, Sandra addresses five of the most asked jobseeker questions that can ease your journey, boost your confidence, and increase your chances of landing your desired job.

#1 Should I make my resume Applicant Tracking System-friendly?

Yes, it is useful if you are applying online, especially through major job platforms.

Think of an Applicant Tracking System as a digital recruitment gatekeeper that allows employers to easily manage and track applications, hiring processes and the communication between applicants and recruiters.

Therefore, if your resume is not optimised, it might never be seen by a human recruiter.

Tips:

• Keep the format simple: Use clear headings, stick to standard fonts, and don’t include tables and images.

• Use keywords from the job ad: Mirror the language and skills listed in the posting, so that the system picks up your relevant experience.

• Try the e2i AI Resume Builder: It tailors your work history and summary to the job you want and gives you real-time feedback. It is a smart way to make your resume stand out to the ATS and hiring managers.

Visit the e2i AI Resume Builder to boost your application.

#2 Which tools are better for mature PMEs—job sites or LinkedIn?

Use both! At your level, many opportunities arise through connections rather than cold applications.

Job sites help you cast a wide net while LinkedIn is a powerful tool for networking and personal branding. After applying for roles on job sites, find the hiring manager or team member on LinkedIn. Send a short personal message to mention that you’ve applied for the job, why you’re interested, and how you’re a good fit. This shows initiative and helps you stand out.

Both job sites and LinkedIn are important. However, don’t forget about the hidden job market as many roles are often not posted. Tap into it by:

• Reaching out to your network, including former colleagues, mentors and clients.

• Joining professional groups or alumni associations.

• Attending industry events or webinars.

• Working with career coaches or recruiters who may have insider information.

The key is to be proactive and visible, online and offline.

#3 Should I apply to jobs that list more years of experience than I have?

Yes, if you meet most of the must-have requirements and can show real impact.

Job descriptions often describe an ideal candidate as someone who blends non-negotiables, like key skills or certifications, with nice-to-have experiences that help you stand out but aren’t critical.

Even if you don’t tick every box or have fewer years of experience, your relevant achievements and transferable skills can matter more than working years.

Tips:

• Highlight the must-haves in your resume and support them with specific examples.

• Use metrics and results to show your value clearly.

Don’t self-eliminate; you may be closer to the ideal candidate than you think.

#4 During an interview, how do I explain a short tenure at my previous job and the reasons for leaving?

This is one of the most frequently asked questions I receive from clients. A short stint can feel awkward to explain, but it need not be.

What matters most is framing it with maturity, clarity, and a focus on your growth and future direction.

During coaching, I guide clients using the H.O.P.E approach. The approach is more than just a framework; it is also a mindset that helps jobseekers respond with clarity and confidence while staying true to their values and future goals.

Here’s how to make the H.O.P.E. Framework work for you:

• Be Honest

Start with a genuine explanation. There’s no need to go into every detail, but you must be authentic.

You can say: “When I accepted my previous role, it felt like a strong match based on the job description and conversations during the hiring process.”

• Stay Objective

Stay neutral and professional. Avoid using blaming or emotional language.

Try this: “Once I was in the role, I found that the scope and expectations differed significantly from what was initially communicated. I quickly realised it wasn’t the right long-term fit for either side.”

• Use Positive Reframing

Focus on what you gained from the experience.

You can say: “That experience gave me valuable insights into how I work best, and I developed skills such as [for example, adaptability, communication and project coordination]. It helped me understand the kind of culture and leadership style I thrive under.”

• Radiate Energy

End the interview by showing enthusiasm for and alignment with the role.

Consider saying: “That’s why I’m genuinely excited about this opportunity. It aligns with my strengths in [X] and my passion for [Y]. I’m eager to contribute meaningfully to a role where I can grow and make an impact.”

A short tenure does not define you, but how you talk about it does. Use the H.O.P.E. framework to show that you’re not running from something but intentionally moving toward a better fit with clarity, self-awareness, and motivation.

#5 Can the interviewer ask for my last-drawn pay?

This question can be tricky. In some workplaces, it’s expected. In others, it’s discouraged.

You are not obligated to share your past salary if you are uncomfortable. Instead, you can politely shift the focus by saying: “I would prefer to focus on my salary expectations based on my current skills, responsibilities, and the value I bring to this role rather than my previous pay.”

Do your market research. Before the interview, check platforms like MyCareersFuture, Jobstreet, or Payscale to find the average salary ranges for the role, industry and experience level. Then confidently share a salary range that reflects your value, not just your past salary.

Need more guidance to navigate tricky interview questions, improve your resume, or prepare for your new job? Visit e2i’s career resources or book an appointment with our career coaches.