Interviewing Diaries: The Search for a New Beginning

Olmo’s mission has always been to help pay it forward. The founding team of Olmo had the goal of democratizing access to knowledge and career advancement, and to help people rethink networking.

It all sounds fine and dandy, aspirational even, until it comes time to actually do it. Beyond just struggles with developing and growing the app – which is a large topic in and of itself for another day – how does one actually take the ideas of “reinventing networking” to life?

As I revisit my own approach to finding a new role to land in, I had a chance to practice what I used to preach. I would say, “network your way to a new job!” but in reality I would also go to job boards and apply for positions the old fashioned way. Sadly, it’s hard to just get away from the allure of just filling out a simple form (which LinkedIn could even fill out for you) and then submitting it to the void. It’s anonymous, easy, and similar to when you applied to colleges; just fill out a common college application form and then just see who reaches out for an interview or just accepts you on paperwork alone. So now, how do I change the way I’m looking for roles and getting a new job?

One important exercise I absolutely had to do first was take stock of my career. Where am I now. What have I done. What do I want to do next. Rewriting my resume and refreshing it along the way really helped me take stock of where I’ve been and craft a better story about my career pathway. It takes a mental shift for sure, because depending where you are in your job search, it is likely coming from a place of unhappiness: You’re unsatisfied at work, you’re looking for a change or for more money, or you’ve just lost your job. Few are actively looking while also happy – though that could be a future for folks in other places in life.

Once that was done, it was all about reaching out. Reaching out to closer contacts who are at other companies that you want to enter via text or email, and simply asking:

“Hi (name), I am looking for new opportunities and found one at your company! Any tips about it? / Are you happy there? / Can you let me know how I can get an interview there? / Are you still looking for someone in this role?”

Most of the time, you’ll get a response. It may be helpful, it may not. But not all leads are dead ends because at this point one thing is for certain: “Name” just learned that you’re looking for a new job. There’s nothing embarrassing about that; people are always looking for one reason or another. But what’s great is it’s a seed in their head and if they learn of anything and know what you do, they might just be able to suggest things and help.

Then it’s about reaching out to some of the more tenuous connections. Sometimes they’ll reply, sometimes they won’t. It’s okay if they don’t; it’s usually nothing personal. Sometimes they’ll provide a lead, and sometimes they won’t have one. Again, the goal accomplished is that people know that you’re looking.

“Hi (name), I hope you’re doing well! I am looking for new opportunities at your company and I am interested! Any tips about it? / Are you happy there? / Can you let me know how I can get an interview there? / Are you still looking for someone in this role?”

Another tip I had received and definitely followed up on was joining the new job matching services: Hired, Vettery, Workbridge,,, etc. All it usually takes is filling out a form or profile. Mind you, most of these job boards are for tech roles. There are probably similar ones for other industries, and there’s even one for remote female workers. They do all the work for you – most definitely. Note that this process is also slow, not necessarily guaranteeing an interview. But if you know who you are and how to present your story, you are more likely to get a view and a match.

And then finally, it does not hurt to keep applying to places. I have seen the constant grind of applying to places work for some people. I have also seen how networking your way to a new job by constantly talking to people, meeting folks at other companies and cold-messaging on LinkedIn work for others. To be very honest, I can’t give a good recommendation on which way works better because I have not yet gotten an offer. (Once I do, I can share a bit more findings from personal experience.) Regardless, I think it’s helpful to do both. If you can apply and also reach out to someone in that company through a tenuous connection, do it. Why not?

Everyone works on their own timeline, and some have to be on an accelerated timeline more than others. But regardless, remember that it’s not a competition. It’s not a race. It’s about knowing yourself and presenting the best version of yourself for the next role. How you choose your next role can be very personal (i.e. money vs. work/life balance?) and not to be judged. But the most you can owe yourself is to feel like you can learn something at your new job. Regardless of your position and title, if you feel like there’s one thing you can learn more than at another place, then wouldn’t it be a worthy place to go? The work may not be sexy, but it’s all about a matter of perspective.

As Meghan, Duchess of Sussex recently said (and I paraphrase), it’s not just important to live life to survive, but also to thrive.

And so I throw it back to you – what have you done as you search for a new job? What has worked better for you? What didn’t? What would you redo if you could do an interview over again?

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