In my last post, I argued that digital platforms and resume screeners are likely to filter out even mildly unconventional applicants, since recruiters are forced to optimize on criteria that are readily available to them at that stage of the process. Even if they recognize that these criteria are neither necessary nor sufficient for excelling at the job, the constraints of the hiring funnel leave them little choice.

For candidates whose strengths lie in less easily quantifiable areas, or whose experience doesn't map neatly onto the "preferred qualifications" checklist, this presents a challenge. How can you convey your potential to excel in a role when your resume doesn't fit the standard mold?

The solution, as I alluded to previously, is finding ways to bypass the initial screening process altogether. And the most powerful tool for doing so is to use networks outside the normal recruiting channels to convey this information. You can either find someone who’s already willing to vouch for you or you have to start a process that will make it increasingly likely that one of the people you come in contact with will recommend you for an interview. A trusted referral acts as a de-risking mechanism for employers, providing insight into crucial intangibles that a resume alone could never convey.

Connecting with the “cringe” in networking

For many, the idea of "networking" conjures up images of awkward happy hours and transactional small talk. I want to make two claims:

1. Going to events with "networking" in the name is likely one of the worst ways to network.
2. Unlike most others who write about this, I won't give you "pickup artist" advice to "overcome the cringe." A lot of "networking" is cringe, and you should be mindful of sabotaging your reputation. But if you're worried about this, you should worry less. Your hesitation is precisely why you should feel more confident about doing it.

It's worth reflecting on why we find networking cringe. Part of it lies in why we find some forms of self-advocacy cringeworthy. We have norms against bragging, for example. But there are nuances to understand.

Firstly, it's easy to misunderstand this as a norm against self-promotion altogether. If someone whips out a guitar and plays excellent music at a party or seems to know a lot about an obscure topic, we're generally impressed. We don't mind that they've communicated that information implicitly. However, we're not so amenable when someone tells us how smart or good they are at their job because words are cheap, and subjective judgments only carry weight when a trusted third party says it. These are cheap signals, and it's in your interest to send them, but why should others let you use up their time for unreliable information?

The second problem is adverse selection. While sleazy bullshitters are a small proportion of the general population, they are overrepresented among active networkers. This means the person you're reaching out to might be wary of your intentions.

Two stages of networking: Informational (testing fit, gathering intel) and Evaluative (pursuing opportunities, showcasing value)

In general, there are two broad categories of people you'll want to connect with, falling along a spectrum from informational to evaluative networking.

Informational Networking: Early on, you'll want to focus on gathering intelligence, testing your fit for the field, and refining your understanding of what it takes to succeed. This might include reaching out to junior to mid-level practitioners, thought leaders, professors, researchers, alumni, or former colleagues who have made a similar transition. Your primary goal is to learn and explore, not to immediately ask for a job or pitch yourself as a candidate.

Evaluative Networking: As your job search progresses, you'll want to shift towards impressing and persuading hiring managers, recruiters, and other decision-makers to take a chance on you. When engaging with these individuals, your goal is to demonstrate your value and potential while still maintaining an attitude of curiosity and openness.

The key is to gradually shift your networking efforts from informational to evaluative as you gain confidence in your fit and readiness for a role.

Three Tactics for Reaching the Right People

1. Targeted Serendipity: This pertains to actions that increase the probability that you'll meet people who are likely to be of interest to you. It could be going to parties or conferences frequented by some target demographic. It could also mean attending meetup groups or discussion groups, for example.

2. Thinking Forward from Your Existing Network: This starts with taking stock of where you are and who you know - friends, family, professional acquaintances, former colleagues, etc. A big part of this is just meeting and keeping in touch with people and giving them updates on your career. Some people will just offer up help or introductions. But if you're sure enough about wanting to explore something, cash in your chips and ask, "Can you think of anyone you can introduce me to?

   A word of caution: I've received these types of emails from some people who barely knew me, asking if I can introduce them to x or y person and no other context. I refused to respond - I didn't want to bother someone I didn't know very well for someone else I didn't know very well. So with people you know well, they probably don't need a reason to do you a favor and introduce you to someone. But if you don't know them well, I guess it can't hurt to ask, but your chances are a lot better if you ask in a way that lets them know (1) they don't owe you anything, and you don't expect them to do anything they're uncomfortable with, (2) you're open to them helping connect with someone else if they think someone else is a better fit, and (3) you're generally asking for their advice and put. I'm sure there are some pushovers who will introduce you to anyone if you just ask assertively, but that's not me, and I don't think that's most people.

3. Working Backwards from Your Goal: You can reach out to people in a targeted way, selecting people who are likely to have relevant information or opportunities for you down the line. If you don't have warmer ways to reach these people, it's totally fine to cold email them.

   Cold emailing is actually not as bad as people make it out to be. This strategy will never have a hit rate that's above 50%, but you can certainly manage a double-digit response rate if you remember the fact that what you're looking to do is give the person a reason to give you more of their time. If you get an intro from someone, the fact that you were introduced might be reason enough for them to talk to you. If you're writing to someone cold, you want to give them a clear reason.

   This reason needn't be explicit. If you're asking someone for advice, it's unlikely that right after giving you advice, you'll be able to help them in some other way. But if you take a more strategic view towards things, you can notice that most people want to be connected with smart, thoughtful people. If you really are an interesting person and can leave a mark, they want to be the one that knows that type of person - the type of person that will make them look good should they connect you to someone else. So in these interactions, you want to signal two things: that you're a generally competent person worth knowing and that you're a generally competent person who has a reasonable chance of being in their network/field/ambit. .

Sending Hard-to-Fake Signals While Communicating

In a world of language models and AI, simply knowing random facts about an organization or using industry buzzwords is not enough. Instead, you need to find ways to showcase your knowledge and expertise with plausible deniability for showing off.

One way to do this is by understanding the value chain or mechanics of the industry you're interested in. For example, if you're talking to someone from a digital lending company in Malaysia, you could ask, "Do you lend off of your own balance sheet, or do you have partnerships with banks?" This demonstrates that you understand the different business models in the industry and are genuinely curious about their specific approach.

Similarly, if you're talking to a program manager at a non-profit working on malaria, you could ask, "Do you have boots on the ground, or do you work with a local non-profit?" This shows that you understand the different ways non-profits operate and are interested in their specific strategy.

These questions aren't hard to come up with if you've done your research and spent time conceptually understanding the industry. They demonstrate to the other person that you know your stuff without explicitly stating it. In contrast, a professional networker might say something generic like, "Oh great, that's an exciting space to be in. Have been hearing lots about it." The difference is clear.

Generally, your questions should fall into one of two categories: they should either be actually useful in a practical way for you (in which case you should make sure this question isn't easily answered by just googling it), or they should be questions that people can only come to once they've put in some legwork.

Sending Hard-to-Fake Signals Through Actions

Another way to circumvent this problem of cheap signals is to do something substantive that reflects your intent and/or intellect.

One way to do this is to put your thoughts and comments on a related area out there in the form of blog posts, for example. Now, it wouldn't be a good idea to start a different blog every time you want to superficially explore something. This is probably best saved for when you've made a reasonably firm commitment towards transitioning into a new career. Writing is obviously a more relevant way for showcasing abilities in some fields than others. One of my professional acquaintances, who leads a think tank in DC, said writing relevant articles on Substack is probably an underrated way to demonstrate interest and showcase skill.

Even if this doesn't help you get noticed, this is evidence for you to point to while reaching out to someone - it proves you're not a fly-by-night operator, you know more than the typical outsider, you're interested enough to articulate your thoughts, and hopefully, that you articulated your thoughts eloquently. A rookie mistake one can fall into here is to write confident editorials about something you barely have a grasp over. If unsure, it's better to stick to things like explainers/primers where you can help people understand something as you go about understanding it yourself.

Another way to accomplish this in a more targeted way is to try and get an opportunity to demonstrate your capabilities in some way that's not expensive for the other person to assess. You could do an interesting mini-project and getting feedback on that can potentially be a way to get in touch with someone. You could also offer to do pro bono work for people in the space. Even if the work itself doesn't directly lead to a job, you can probably get people in the same industry to vouch for you now or introduce you to someone who is looking to hire.

Avoiding the Sleazebag Vibe

To avoid coming across as a sleazy networker, steer clear of behaviors that people just trying to gain influence often resort to. For example, sleazy networkers tend to name-drop a lot while knowing very little about the substance of what they're discussing. This leads them to rely on vague statements or excessive flattery to make conversation.

Generally, indulging in hyperbole like "Your article on consumer goods was profound" is inadvisable if you want to connect with serious, thoughtful people. Those who respond positively to such flattery usually aren't the ones you want to associate with professionally.

Also, avoid anything that might make you seem overly status-obsessed, like trying to get introductions to unreasonably senior people at an organization while talking to more junior employees. This is a classic mistake that can make you appear overly ambitious in a graceless way.

Most importantly, give people an out and don't come across as overly demanding. Make it clear that you value their time and don't expect anything from them. Politely offering a reason for them to connect with you or help you is fine, but pushing too hard will only alienate people and cement your reputation as someone to avoid.

Conclusion: Embracing the Positive-Sum Nature of Labor Markets and Overcoming Psychological Barriers

When you invest in your own growth and seek out opportunities to connect with others in a genuine, mutually beneficial way, you're not just helping yourself, you’re helping create positive sum dynamics that drive the engine of growth and progress . Networking done right is both selfish and pro-social, and that's exactly the kind of win-win dynamic that has driven human civilization forward for centuries.