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How To Explore Careers & Find A Job By Talking To People

A Comprehensive Guide To Succeeding At Interviews & Networking

By Grace Chao

In my last post, I discussed the importance of talking to people when trying to figure out what career is right for you. In fact, career chats – also known as informational interviews, informational meetings, coffee chats, and more generically, networking – are useful not only for career exploration, but job searches as well. While you should never make landing a job the purpose of a conversation, it’s not uncommon for conversations to lead to opportunities (based on one report, 1 in just 12 informational interviews leads to a job offer).

Yet, despite their proven ability to deliver both career-advancing information and opportunities, career chats are an underutilized tool. People aren’t taking enough advantage of them, in large part, I believe, because they find them challenging to execute. This is a real shame, because all it takes is knowing a few techniques and a little practice. Today, my goal is to lay out everything you need to know to successfully wield this powerful tool. (Note: the next 6 pages are densely packed with information, so be prepared to spend a bit of time reading through them.)



A friend of mine graduated from an Ivy League university several years ago and needed to figure out next steps. He decided to reach out to his college alumni network and proceeded to painstakingly pen numerous detailed and lengthy emails to alums he hoped to chat with. The result? Crickets.

The first thing to keep in mind when requesting conversations from people who don’t know you is to be concise. Attention spans are short, so you must get to your point quickly. In general, emails shouldn’t be longer than 5-8 sentences, and they should be formatted for easy readability. If you present a wall of words to people, many of whom read their emails on a small mobile screen, your note may well be ignored, or left to later and then forgotten.

Your email should cover 4 things:

(1) who you are

(2) why you’re reaching out

(3) what you’re requesting (typically, a quick coffee meet-up or 15-20 minute phone chat)

(4) something to pique your target’s interest

This last item is what distinguishes a good outreach from a great one. Research your target and try to incorporate something that would captivate their attention, such as something you and your target have in common, a fact about yourself that your target may find interesting, or a reason why your target could benefit from a conversation with you.

For examples of well-written emails, check out these articles:

Students: for a real-life example of successful outreach by a student, check out this article and actual cold email by a rising college senior I met recently, Michael Riley. Michael has deftly leveraged career chats starting his freshman year to figure out what career to pursue, land two sought-after internships as a sophomore and junior, and continually explore career options.

Emails are not the only way to reach out. Phone calls, while less popular nowadays, work too. As with emails, the key with calls is communicating a concise and compelling request. Aim to introduce yourself and make your ask in 20-30 seconds, whether you reach your target on the phone or leave a voicemail.

You can also of course request career chats in person. There are many situations that could present an opportunity to do so – networking events, meetups, gatherings of friends and acquaintances, chance encounters, etc. You will have to use your judgment on when it’s appropriate to make an ask, but as long as you’re courteous, you will be in good stead, regardless of whether the person is ultimately able to grant your request.

Finally, an often-overlooked channel for outreach are online forums and other social networks, through which you can effectively reach out to many people at once. With online posts, feel free to provide more details around what you’re seeking to learn. Sometimes even if people are not available to chat, they will offer insights in writing. (Recently, I saw a post on Reddit by someone who was interested in becoming a pilot. He listed 13 questions he had about this career path, and within a month, had received 6 full sets of thoughtful, written responses to his questions.)


There is no one way for how a career chat should be conducted, because it all depends on the particular circumstances of the conversation and who you’re talking to. However, the starting point for any successful conversation is having the right mindset and attitude, and on that front, here’s what I suggest:

#1: Be curious and open-minded. The point of career chats is to get information and trigger new ways of thinking, so seek to learn as much as you can from the other person.

#2: Be honest. Besides being the right thing to do, people tend to share more with people they find are trustworthy.

#3: Be appreciative. Don’t forget to express your thanks for the time and insights shared with you, and if there is an opportunity, try to return the favor.

#4 Be relaxed. Not every conversation is going to go as expected. Awkward conversations do happen — just take them in stride and remember that the not-so-great experiences sometimes prove to be the most valuable ones.

For in-person meetings, bring a pen and paper in case you want to take notes. And dress professionally. Professionally means whatever fits in with the style and industry of the person you’re speaking with. If you’re meeting a banker, a suit would likely be appropriate, but if you’re meeting someone who works for a tech startup, business casual could be more fitting.

Now for some conversation techniques:

#1: Prepare a mental list of the key things you’d like to discuss and ask.

Conversations may not always flow in the way you expect them to, and a list will help you keep them on track.

#2: Plan out how to kick off the conversation.

If you’re speaking with someone you’re meeting for the first time, it’s typical to start with a quick (under 2-3 minutes) self-introduction, during which you can share relevant facts about your background, where you are in your career exploration or job search process, your career ambitions, and what you’re hoping to get out of the conversation. You should invest some time into crafting, even scripting, your self-introduction (or, as some say, your “story”), so that it conveys what you’d like the other person to know about you in a succinct and, ideally, interesting way.

If you’re speaking with someone you know, obviously you don’t need to introduce yourself, but think about whether there are things you should update them on (e.g., new career developments, life changes) and how to set the stage for discussing the topics you have in mind.

#3: Listen more than talk.

(Pay extra attention to this, extroverts, as you tend to listen less than your introvert peers.) How much listening should you do? There’s an excellent talk entitled “How To Sell” by the CEO of Clever, Tyler Bosmeny, that gives us a clue. In it, Tyler discusses how the best salespeople spend 70% of their time listening and only 30% speaking when conversing with potential clients. If sales conversations call for 70% listening, then career chats, whose main goal is not selling but information gathering, should have even more. New York Times best-selling author, career expert and entrepreneur Ramit Sethi recommends 90% listening.

#4: Prepare open-ended questions that relate to your career needs.

If you’re to be listening 70-90% of the time, you need to prompt your conversation counterparts to do most of the talking by asking questions that will elicit detailed responses. A good way to start is by asking them about their professional background (e.g., “how did you choose your career path?”). People generally enjoy talking about their own experiences, so you’re likely to learn quite a bit just from this. If you’re at a loss as to what to ask after this, think about what’s important to you in a role and a career and prepare questions that will yield insights in those areas. You can ask about almost anything that is relevant to career decisions as long as the questions are phrased appropriately. (For example, if you wish to ask about the sensitive topic of compensation, Harvard Business Review article “How to Get the Most Out of an Informational Interview” suggests saying something like “I’ve done some research online, and it seems that the typical salary range is this…”.)

There are two kinds of questions, however, that you should refrain from asking. The first is any question whose answer you can easily find on your own through some research. These questions are a waste of time and will reflect poorly on you for not having done your homework. The second is asking for a job. If the other person knows you’re looking, these questions are unnecessary and can create awkwardness. However, you can certainly ask for job search advice (e.g., “how would you go about conducting a job search in this market?” and “how should I position myself for a job in this field?”).

For ideas on other questions to ask, check out the articles below. To their suggestions I will add just one more, a question someone once shared with me that I haven’t seen on any published list: “How do you measure success?” (I love this question because you can take it in so many directions and reap insights on a variety of areas, including corporate goals and strategy, industry culture and trends, performance evaluation and personnel qualifications.)

#5: Practice “show, not tell” when promoting yourself.

Though career chats are centered on information acquisition, they are also opportunities to soft sell yourself and impress the person you’re speaking with. If you wish to do so, use the “show, not tell” technique. I learned this term from a very wise friend of mine who after successful careers working for companies from Silicon Valley to Wall Street wrote a book that helps students enter into the real world. In “Landing Internships and Your First Job” (which I recommend not only for students and recent graduates, but anyone who would like to brush up on their job search skills), Jerry notes that the best salespeople “show, not tell” because they know that getting people to feel like they’ve come to their own conclusions is more powerful than telling them what to think or do.

Jerry also explains how to “show” versus “tell”. If you say “I’m a hard worker,” that is a “tell”, or a claim without any evidence. However, if you say “I worked 15 hours a week while carrying a full course load during the school year”, you would show that you are a hard worker without flat out saying it. So, when promoting yourself, instead of asserting that you possess certain qualities, share experiences and anecdotes that demonstrate them. A good place to work those into the conversation is right at the beginning, during your self-introduction.

#6: Wrap up the conversation at the scheduled time and ask for final advice and referrals.

Respect the other person’s time by ending the conversation on time. Thank them for the conversation, ask if they have any final advice, and if it feels right, ask if they can recommend someone else for you to speak with. Not everyone will be able to, but it’s worth checking if you think it may be possible.

Lastly, once you’ve finished a conversation, jot down what you’ve learned and reflect on the conversation. Not every piece of advice, however well-meaning, will be suitable, nor every piece of information accurate. Come to your own conclusions as to what to act on, what to give further thought or research to, and what to set aside.


Always send a thank you note within one to two days after a conversation. Along with expressing your gratitude, you can address any next steps that may have arisen from the conversation (such as sending over information you promised to send). Check out these articles for good sample thank-you notes:

After the initial follow-up, if the other person had made an introduction for you or given advice that you had acted on with significant results, be sure to send an update about that. And down the road, if you come across a way to be helpful or information that could be valuable or interesting to the other person, let him or her know. That is how relationships are built.

Separately, besides following up after conversations, you should also follow up if you don’t hear back on a request for a conversation. It is not unusual for people to forget to respond, so you should follow up at least once, some say twice. Give it a week or so between emails, and acknowledge their busy schedules. If you still don’t hear back after two follow-ups with someone you really want to meet, you’ll need to judge whether continuing to follow up makes sense. Persistence could irritate your target, but it could also work, as many successful people can attest. If you do decide to keep at it, think hard about whether there is a different angle you can use to get the person interested in speaking with you.


The short answer to who to approach for a career chat is anyone who you believe could provide valuable insights and will make time for you.

This can, in fact, be absolutely anyone – your family, friends, friends of friends, acquaintances, alumni from your alma mater, fellow members of a community, social or religious organization, people you haven’t spoken to in a long time (check out organizational psychologist and University of Pennsylvania professor Adam Grant's article about dormant ties), former co-workers, partners and clients, professional contacts you have some weak connection to, even total strangers, including industry leaders. Career educator Paul Binkley, who has served in the career services departments of George Washington University, Johns Hopkins University and the University of Mary Washington, once shared with me an informational interview guide he wrote that included this story: a student whose dream job was to run a Fortune 500 company called the president of Levi Strauss & Co., asked for an informational interview, and got it!

In general, the stronger the tie between you and your target, the more likely you’ll get a positive response. According to LinkedIn, almost 70% of working professionals would help someone they know find a job, while 10% would help someone they don’t know. The weaker the tie, the more you’re going to have to work on piquing their interest in speaking to you. That said, I also want to pass along an observation by a friend of mine who had methodically reached out to something like 100+ people during a job search: “Sometimes the people you expect to respond won’t, but the people you don’t expect to respond will.”

As for contacting people with whom you have no ties whatsoever: some of you may be wondering if it’s worth the effort. Indeed, it will take a lot of effort, but it could also deliver incredible results, as it did for a former co-worker of mine.

After suddenly losing his job right before Christmas one year, my former co-worker found himself at crossroads in his career. He wasn’t sure if he wanted to stay in the high-pressured world of finance or switch to more of a “lifestyle” job. He was also wondering whether to keep living in the Midwest or go somewhere else. So he began reaching out to a lot of people for career chats. One of those people was a gentleman whom my co-worker had zero ties with. Long story short, this gentleman connected my co-worker to my boss, and that’s how my co-worker landed a job at my firm in New York. The best part? My firm wasn’t even looking for someone with my co-worker’s background.

Cold outreach is a numbers game. You must reach out to a lot of people to score a connection, but when you get one, you just might strike gold, because unlike your strong ties, weak/zero ties are more likely to have information you don’t have, since they tend to travel in different circles from you. As a classic study by sociologist and Stanford University professor Mark Granovetter showed, people were 58% more likely to get a new job through weak ties than strong ties.

With perseverance, you can win at the numbers game, particularly with the aid of technology. There are many tools that can help you locate people’s contact information, send bulk emails while personalizing each one, and remind you when to follow up. Check those out. And check out the platforms that can help you identify who to talk to, including LinkedIn, Facebook, Twitter, and of course, KIP101, whose platform was built for the express purpose of connecting people for career chats and other 1-on-1 conversations that drive professional growth.


We live in a world where it’s becoming harder and harder to keep up with changes in the workplace brought about by technological progress, increased global competition, and now a worldwide pandemic. To make the best career decisions, you must have the best information on not just the jobs and careers of today, but those of the future. Talking to people is an indispensable tool for information acquisition, and it is very much a skill that can be acquired, as I hope this article has shown. So invest time in career chats. Talk to as many people as you can, whenever you can (not just at critical career junctures), and reap the benefits of accessing a full range of insights, perspectives and opportunities.

Wish you all the best in your professional journey. May you achieve a fulfilling career that is worthy of your talents and aligned with your interests and values!

Grace Chao is the creator of KIP101, a new, free app that connects people for 1-on-1 conversations the drive professional growth. To try out the app, use the invite code "KIPblog".


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