I’ll always remember the moment when I decided that I wanted to jump to the tech industry.
It was 2015, and Twitter had invited us, as clients, to their new Singapore office on Cecil Street. It was filled with colourful lamps and beanbags and Peranakan tiles. It might have looked conventional by today’s standards, but back then, I was blown away by such a beautiful space. It’s dumb to base a career decision on something as superficial as an office, but from that moment on, I knew that I had to find my way into the tech industry.
The problem? I had zero experience in tech. At that time, I’d been working for an airline for 5 years, focusing on admin tasks like writing minutes and organising events. I had no idea what an API or a conversion rate was, nor did I speak in the pseudo-American accent that all my tech vendors seemed to have. Compared to all the cool kids in tech, my own experience seemed hopelessly quaint (writing minutes?!) and mundane (picking out check-in carpet materials?).
Do Research As A Baseline, But Don’t Overdo It
Like most areas, my first instinct was to do research: I’d Google around randomly, read books like The Lean Startup, and even took some Coursera courses. However, everything I read seemed way too theoretical, and weren’t helpful in helping me understand the fancy terms that my tech vendors were throwing around, like programmatic, and trading desks, and second-price auction.
In the past few years, I’ve spoken to several friends who’ve also wanted to do mid-career switches. Like me, they convinced themselves that their work experience was irrelevant, and figured they needed to overhaul their skills. Many of them dropped $200K on an expensive MBA program, or spent 6 months doing a coding bootcamp, only to find that those didn’t get them any closer to switching industries.
Of course, doing some baseline research is important – you have to know the “shape” of your new industry – but what I’ve found is that you don’t need to spend thousands of dollars or months of effort to change careers. Instead, there’s a far less expensive and better-ROI approach that’s worked for me: Simply talking to people.
Personal finance expert Ramit Sethi calls this an informational interview. In a nutshell, it involves reaching out to people in the industry you’re interested in, and simply asking them questions about their experience.
After Googling around for months without any progress, I tried out informational interviewing. The results were great (I landed a tech role within 3 months), so I wanted to share how I approached it here:
- Reach out sincerely
- Ask good questions
- Respect their time
Reach Out Sincerely
First, I used LinkedIn to reach out to different people working in tech and asked if I could find out more about their jobs. I sent out messages saying, “Hey I’m really interested in this industry, and if you’re open I’d love to meet for a 30-min coffee to find out more about what you do in XX“.
I was really nervous about doing this at first, but it turned out that a surprising number of people were willing to talk about their jobs. Not everyone responded, but I managed to secure several coffee chats or phone calls with people working in tech. Why are people so open to sharing? I don’t know for sure, but my guess is that it’s an opportunity to talk about work without any agenda. It’s fun to reflect on the lessons, the challenges, the quirks about your job, and share them with someone who’s actually willing to listen (unlike your friends who’re probably sick of you talking about work).
Now, LinkedIn has become really cringey in the past couple of years. One reason is because everyone who DMs you wants to sell you something or get a job referral. That’s why it’s even more important today to be sincere. You’re there to learn, not to solicit a job referral. And trust me, people can tell when you’re being transactional.
It also helps if you ask people in your network to introduce you to people to talk to. One night, I was seated across an ex-schoolmate at a wedding dinner and I told her I was interested in switching to tech. She offered to introduce me to her ex-colleague who was working at Tripadvisor at the time. That warm introduction helped me to establish trust when I met her ex-colleague for coffee, and it eventually landed me my first role in tech.
Ask Good Questions
However, my first few meetings were absolute disasters. I was nervous, and I peppered my interviewees with random questions with no direction. I thought I had to sound smart, so I asked them about strategy, or the latest news on share buybacks. My questions were often met with confused silences or generic answers.
I later learned that it was more effective to ask questions about their personal experience working in their role. Some example questions I asked:
- What does your role actually look like every day? What are some of the underappreciated aspects about your job? –> This encourages them to talk about the honest stuff that people don’t write about online. Their answers also helped me to decide if similar roles would be a good fit for me.
- Besides <A,B, and C>, what are the biggest challenges that your team faces in APAC? –> This gives me an idea of the pain points to address if I decide to interview for the role. Saying “besides A,B,C” shows that I’ve done my research beforehand, instead of simply fishing for interview answers. (More on pre-research in the next section)
- What kinds of people tend to do well in your company? What behaviours are generally frowned upon? –> This is more effective and specific than “what’s the culture of your company?” which usually evokes generic answers of happy hours or team-building events. It also gives me a flavor of whether I would fit into the culture, and what kind of experiences I should emphasise more on if I decide to interview for the role.
- Given the areas I’m interested in, is there anyone else I should talk to? –> This helps to point me to someone who is working in a role that’s similar to what I’m interested in. It also acts as a warm introduction.
Asking questions like these is way more effective than only doing research online, for two reasons:
First, I got to hear their first-hand, boots-on-the-ground experiences. This helped me to concretise what it was actually like to work there, and dispel my own assumptions. For example, I had always assumed that it was hard for Singaporeans to succeed in tech firms (again, this was in 2015 when not many of my friends were in tech). Yet, meeting several true-blue Singaporeans thriving in tech (and speaking Singlish!) helped me to gain confidence that this was an industry I could assimilate into.
Second, I learned about the unspoken norms and values of their companies. After I narrowed down the list of companies to interview for, I already knew how to frame my answers in a way that would align with those values. For example, I knew that the firms I was interested in prioritised scrappiness and resourcefulness – so I framed my own experience in say, organising a travel agent dinner, into one where I had to be scrappy and get more for less. It taught me that my “mundane” experiences could be transformed into something worthwhile.
Respect Their Time
Lastly, I did my best to make full use of the time of everyone I met. These were busy people with lots of things on their plate, and I calculated that if they earned $10K / month, my 30-min meeting would cost them over $60. Maybe even over $100 if you account for the time taken to travel to meet me. Not insignificant!
My first choice would always be to meet them in-person to establish a better connection, but I was always open to a phone call if they were busy. And I’d go out of my way to work around their schedule, meeting them at cafes close to their office, etc.
I also chose my questions carefully: I didn’t ask them anything that I could’ve gotten from Google or Glassdoor. I did all the pre-research (which also helped me ask more targeted, specific questions), and kept my questions focused on their personal experience, which I wouldn’t find online.
And lastly, I kept them in the loop about my progress. I had a running Google Sheet of all the people I met, and I’d occasionally update them about how my job search was going. When I finally landed my first role in tech, I sent emails to everyone thanking them for their help.
On the flip side, now that I’ve spent 9 years in tech, I’ve also given dozens of (maybe even a hundred?) coffee meetings over the years, I can tell you how rare it is to find a person who actually follows up. Most people just ghost me after the meeting. But there are some who do keep the relationship strong even when there’s no immediate benefit for them – and these are the professional relationships that I cherish the most.
In Conclusion
Will informational interviews guarantee success in switching careers? Of course not. It’s true that many jobs require specialised knowledge like coding or building financial models. And it’s true that sometimes, you might need to build up more relevant experience.
But instead of immediately jumping into an expensive course, bootcamp or MBA, try taking 2 hours to do some pre-research, and then STOP RESEARCHING, and schedule a bunch of coffee meetings. You might be surprised by what you find.
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I know I’ve been MIA again the past 3 weeks! But I finally managed to publish after finding a block of free time today. As you know, I’ve been doing David Perrell’s Shiny Dime challenge, and this week’s writing prompt was Write about a time you overcame an obstacle and achieved something you’re proud of.
