How to find your next dream job or mentor: two strategies to supercharge cold outreach

January 2, 2021
4 min read

Cold reachouts are an important skill to have. When thinking about learning and careers, it’s easy to get caught up in classes, qualifications, and applications. But the most powerful opportunities and connections often come not from a conventional progression, but by serendipity, or intentional reachouts to those in new domains or higher levels. Reaching out to startup CEOs, especially early on, often leads to much better jobs and more meaningful connections than grinding through leetcode and traditional interviews. Reaching out to researchers in a field you’re passionate about can lead to much better mentors and insights than classes you’re taking at school.

Cold reachouts often feel intimidating. Why would a busy CEO, or an accomplished researcher, reply to an inexperienced student like me?

The way to overcome this fear and make cold reachouts work (i.e. get a response, call, job, etc.) is staring you right in the face: answer that question. Give that CEO or professor a reason to reply to you.

In general, there are two ways to do this.

One is to ask for help with a specific problem. People are naturally inclined to help others: you feel good about yourself when you help an elderly neighbor or teach something to a younger kid, for example. One outreach strategy, then, is to make yourself that elderly neighbor/younger kid, and appeal to the person you’re reaching out to’s intrinsic drive to help others. It’s important to share that you have a specific problem that you’re seeking their help with. That little bit of perceived vulnerability and trust provides a last ego boost to encourage someone to help.

If you’re young or a student, you have added credibility that you’re reaching out for genuine learning or self-growth purposes rather than for something less heartwarming like pure financial gain.

For my wireless power transmission research project, for example, I reached out to several researchers. If I had simply said, “I’m working on this research project and I want to call to get information from you,” that’s not a very convincing email. Instead, I briefly shared the research I had already done, and asked for specific guidance on the latest progress in the field and recommendations on specific research directions to pursue, as I had struggled to answer these two questions in my own research. One of the professors I reached out to was a leading researcher in the field who had recently given several keynotes on WPT, and he was happy to answer my questions and share his resources with me.

The second cold reachout strategy is to demonstrate value to the person you’re reaching out to. While the first strategy appeals to an indirect value gained from intrinsic motivation, this second strategy is very straightforward. Think from the perspective of the person you’re reaching out to. What would be helpful to you? What would you want in your life? A video or blog post providing a comprehensive overview your own work or philosophy? A concept for how your product could be improved? Once you’ve identified such a thing, do it as part of your reachout!

I connected with one of my earliest mentors in tech and entrepreneurship, for example, through an email I sent in response to a post he made on an entrepreneurship forum. I was impressed by the app he had built, so I wrote an entire blog post about it and sent it his way. He sent a long email in reply with advice for me regarding school and entrepreneurship; today, I have GPT-3 access because of him, and I’m building the MVP for his new startup. He had been impressed with my blog post because it “explained the philosophy of the app better than I could,” he recently told me.

Ohter reachouts have gotten me job offers, even unexpected ones. One of the most important jobs of a startup CEO is recruiting, after all, so if you show a CEO that you’re passionate about their vision and have something valuable to contribute to the team, you’re likely to get on their radar. After building Updately, I discovered Sunsama (YC ‘19) and emailed the CEO with a few screenshots, reflecting on how we had tackled the same pain points with quite different approaches. My understanding of the problem and product/dev competency immediately caught his eye, and he replied saying he wanted to hop on a call with me as he thought I might be a good next member on the Sunsama team.

A last fun example: a friend of mine, Sigil Wen, reached out to Justin Kan – the founder of Twitch – after going to a Q&A with him. Justin had posted somewhere that he was looking for a content creator, and Sigil concisely plugged his own growth marketing experience. And guess what? He’s now connected to and working with the founder of Twitch.

There are plenty of other tricks and nuances to cold outreach. Follow ups, for example, are extremely important for building meaningful connections. If you asked for help from someone, do what they asked you to and let them know – show that you took their advice seriously, and strengthen their confidence in you. Another simple framing/phrasing trick: instead of asking “would you be available for a 20 minute call?” ask “would you be willing to have a 20 minute call?” Make it easy for them to think, “well, yeah, maybe I would be.” A third detail: for emails, make your subject lines attention-grabbing (“17yo researching biotech industry”, I wrote when reaching out to industry experts for a consulting project) and your messages short. Save the details for a follow-up, or the call.

It takes time to get comfortable with cold outreach, and of course the situation changes depending on who you’re reaching out to. But these two general methods – ask for help, or provide value – have been a useful framework for me.

If you find the framework useful as well, or find success using it, I’d love for you to let me know!1

  1. follow me on Twitter @wwsalmon, or email me at hello@samsonzhang.com