If the thought of reaching out to a stranger for career advice makes you cringe a little, you're not alone.
Many people know that networking matters, but the idea of asking someone for their time can feel uncomfortable. You might worry that you're bothering them. You might feel like you're asking for a favour. Or you might simply dislike the feeling of "selling yourself" to people you don't know.
This is exactly why so many people avoid doing an informational interview, even when it could be one of the most useful things they do during a job search or career change.
The good news is that informational interviews don't have to feel awkward, forced, or transactional. In fact, when done well, they often feel like nothing more than a thoughtful conversation between two people.
Let's look at how to do an informational interview in a way that feels natural, respectful, and genuinely helpful for everyone involved.
An informational interview is simply a conversation with someone who works in a role, company, or industry you'd like to learn more about. It is designed to help you learn about an industry, organisation, or career path through genuine curiosity rather than asking directly for a job.
The purpose is not to ask for a job. The purpose is not to convince someone to hire you. The purpose is to learn.
You might speak to a product manager because you're considering a move into tech. You might talk to someone in a company you're interested in joining. Or you might connect with someone who has successfully made the same career transition you're trying to make.
On paper, it sounds straightforward. In reality, many people hesitate because they feel like they're imposing.
They think:
These concerns are understandable. But they're often based on assumptions that aren't entirely true.
The reality is that many professionals genuinely enjoy sharing their experiences. Most people remember what it was like to be early in their career, uncertain about a career move, or trying to understand a new industry. Helping someone navigate those challenges can actually be quite rewarding.
When approached respectfully, an informational interview is not a burden. It's simply a conversation.
The goal isn't to convince someone to do something for you. It's to learn from their experience.
That shift in mindset alone can make the process feel much less intimidating.
A lot of networking advice focuses on outcomes. Build connections. Get referrals. Find opportunities.
While these outcomes can happen, focusing on them too early is often what makes networking feel uncomfortable.
Instead, approach an informational interview from a place of genuine curiosity.
You are not reaching out because you want something from the person.
You are reaching out because you want to learn something from them.
That distinction matters.
Generic messages often feel transactional because they could have been sent to anyone.
A more thoughtful approach is to explain exactly why you're interested in speaking with that specific person.
Maybe they successfully switched careers. Maybe they work in a company you're curious about. Maybe their career path resembles the direction you're considering.
People are far more likely to respond when they can see a genuine reason behind your request.
One reason people hesitate to reach out is that they worry they're asking for too much.
You can remove that concern by being specific.
Instead of asking if someone can "chat sometime," ask whether they'd be open to a 15- or 20-minute conversation.
A short, clearly defined request feels manageable.
This is perhaps the most important principle.
Don't ask for a job. Don't ask whether they're hiring. Don't ask for a referral in your first message.
Focus entirely on learning from their experience.
For example, someone exploring renewable energy may request a short conversation with an experienced project manager simply to understand the industry, not to ask for employment. Those genuine conversations often lead to unexpected future opportunities.
Ironically, when people feel you're not trying to get something from them, they're often more willing to help.
Many people assume job searching starts with job boards.
In reality, a significant number of opportunities are discovered through conversations long before a role is publicly advertised.
This is often referred to as the hidden job market.
Companies may identify potential candidates through referrals. Hiring managers may have upcoming needs they haven't formally announced yet. Teams may be expanding before job descriptions are even written.
This is one reason why tapping the hidden job market in Singapore can be such a powerful strategy for job seekers.
Informational interviews help you gain access to information that isn't available through a standard application process.
You learn:
Perhaps more importantly, people get to know you as a person.
A CV can show your experience.
A conversation can show your curiosity, professionalism, and potential.
This doesn't mean every informational interview will lead directly to a job opportunity. Most won't.
But over time, these conversations create visibility, trust, and relationships that can significantly improve your job search outcomes.
Even Workforce Singapore encourages job seekers to begin their search within their existing network and professional connections before relying solely on job advertisements, highlighting the value of relationship-based job searching. For readers who want additional guidance, refer to Workforce Singapore's guidance on starting your job search within your network.
Australian job seekers can find similar, government-backed direction in Workforce Australia's official job search guidance, which encourages strengthening your search through connections and conversations rather than relying on online listings alone.
One of the biggest reasons people avoid this interviews is that they don't know what to write.
The good news is that your message doesn't need to be complicated.
Short is usually better.
Hi Sarah,
I came across your profile and noticed that you transitioned from marketing into product management a few years ago.
I'm currently exploring a similar move and would love to learn more about your experience. If you're open to it, would you be available for a 15-20 minute conversation sometime in the next few weeks?
No pressure at all if your schedule is full. I completely understand.
Thank you for considering it.
Best regards,
[Your Name]
Hi Daniel,
I've been researching companies in the fintech space and came across your profile at [Company Name].
I was particularly interested in your experience working within the payments industry. I'd love to hear more about your role and what it's like working at the company.
Would you be open to a brief 20-minute conversation when convenient?
Totally understand if now isn't a good time.
Thank you and have a great day.
Hi Priya,
I'm currently exploring opportunities within sustainability and noticed you've built your career in this space over the past several years.
I'd love to learn more about your journey and any insights you'd be willing to share with someone considering a similar path.
If you're available, would you be open to a short 15-20 minute conversation?
No worries at all if you're unable to.
Thank you for your time.
These messages work because they're clear, specific, and respectful. They don't create pressure. They simply invite a conversation.
Once someone agrees to meet, many people worry about saying the wrong thing.
The quality of your questions often determines the quality of the conversation. Focus on understanding experiences rather than collecting facts you could easily find online.
You don't need a perfect script. You simply need thoughtful questions.
Some useful informational interview questions include:
Focus on understanding their experience rather than trying to impress them.
Curiosity is often more memorable than expertise.
The difference between meaningful networking and transactional networking often comes down to what happens after the conversation.
Many people disappear until they need something again.
That's when relationships start feeling transactional.
Instead, think about building genuine professional relationships over time.
A simple follow-up message goes a long way.
Thank them for their time.
Mention one specific insight that was helpful.
Show that you genuinely listened.
Reciprocity doesn't mean repaying someone immediately.
It simply means contributing where you can.
Perhaps you come across an article related to a topic they mentioned.
Maybe you attend an event they might find interesting.
Small gestures help transform a one-off conversation into an ongoing relationship.
You don't need to message every month.
But if you make a career move, complete a course they recommended, or achieve a milestone related to your conversation, consider sharing an update.
People generally enjoy seeing that their advice made a difference.
This is one reason why networking matters for landing a new job. Strong professional relationships are built through ongoing connection, not one-off requests.
Over time, these relationships become far more valuable than any single job application.
If the interviews feel awkward, you're not imagining it. Reaching out to people can feel vulnerable, especially when you're already navigating uncertainty in your career.
But done well, informational interviews are not about asking for favours.
They're about learning, building genuine relationships, and discovering opportunities that may never appear on a job board.
The challenge isn't usually knowing that networking matters. It's knowing how to do it in a way that feels authentic.
That's where support can help.
The Happy Mondays Co.'s Job Landing programme helps professionals develop effective networking strategies, create outreach scripts that sound natural, and build confidence in hidden-market conversations. The goal isn't to turn you into a salesperson. It's to help you have better career conversations that lead to meaningful opportunities.
Because often, the opportunities that change your career begin with a simple conversation.
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Founded in 2016, The Happy Mondays Co. empowers individuals, companies, and communities to achieve success on their own terms. Awarded top career coach in Singapore and Melbourne, we pride ourselves with an evidence-based approach grounded in empathy, candour, and confidentiality.
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