Reach Out, Stay in Touch and Deepen Your Connections with This Essential Networking Advice
People & Culture

Reach Out, Stay in Touch and Deepen Your Connections with This Essential Networking Advice

Networking isn't a race to rack up contacts — it's a practice of cultivating authentic connections over time. We've rounded up six tactics from the most well-connected people in the business on cutting past the small talk, nailing the follow-up and investing in relationships that thrive.

Mention the word “networking,” and you might conjure repressed memories of awkward handshakes, disingenuous small talk and the utter dread of opening an email from a stranger who wants to “pick your brain.” Yet despite its unpleasant reputation, most people understand that networking is important, even vital. Connections are the steady undercurrent that powers the tech world, supercharging the careers of the founders, operators and investors who excel at cultivating them.

It’s when we’re actually tasked with putting “networking” into practice, with cementing it into our everyday routines, that we have to navigate around the social landmines. We want to be sincere, not smarmy. We need to reach out deliberately, but in authentic way. We should create relationships that thrive, not just last. We need to stay in touch, but not overwhelm or overstep our welcome.

In search of insight and direction, we dug through the archives for wisdom from six of the most well-connected people in the business, two of whom are self-professed introverts. They universally agreed that the conversation around networking direly needs to be reframed.

It’s not a race to rack up contacts, nor is it a license to give your elevator pitch to everyone within hearing range. Think of networking as the practice of cultivating authentic connections over time. Lead with gratitude and a genuine desire to get to know someone — along with a few handy tips in your pocket — and you’ll be ready to move past handshakes and forge lifelong connections.

Now for those tips. The six tactics that follow are useful for setting a healthy mindset around networking. From a 10-minute routine you can use rekindle connections, to questions you can ask to take small talk beyond the superficial, these tips shed light on how to make strong first impressions and land even stronger follow-ups. They include targeted, tactical advice on doing networking differently, sharing the inside tricks of just how they’ve earned their reputations as masterfully authentic connectors.

There’s no time to waste, either. In the words of Chris Fralic, First Round board partner and consummate “somebody who knows everybody”:

There’s time beyond this fundraise and even this company. Relationships take years to build. Start now.

1. Avoid the two mistakes that stand in the way of really getting to know people.

To forge truly authentic relationships, you need to move people from being strangers to becoming your acquaintances, then friends, then close connections.

Each stage brings its own set of concerns. The journey from stranger to acquaintance is often filled with awkwardness, ice breakers and uncomfortable settings. But the perils of the acquaintance zone are of a different sort: exchanging pleasantries, sticking to shallow conversations and attempting to escape the endless loop of “We should get together sometime.”

In short, there’s a difference between knowing someone and knowing someone — and most networking advice falls flat because it fails to make this distinction.

But that can’t be said of Mike Steib. His approach to networking is of a different mold — and it’s a key reason why his thoughts on building a meaningful network was some of the best advice we featured on the Review last year. To overcome the anxiety that many of us experience when it comes to networking, the current CEO of Artsy and former leader of XO Group has developed a targeted approach for turning the strangers who populate our lives into valuable and cherished connections. Steib likes to think of people moving up through four nested concentric networks: Unfamiliar → Familiar → Intimate → Meaningful.

Your Unfamiliar and Familiar Networks are straightforward enough — people you don’t know at all and acquaintances you know a little, respectively. But that’s where the demarcation is drawn, where you need to shift from light networking and “knowing” people to truly connecting and going deep. For those of us looking to land the leap from small talk to meaningful conversation, Steib’s lightweight yet highly tactical advice is perfect for really getting to know a subset of people with whom you’d like to have a closer connection.

Here it is in his own words:

You bring people from your Familiar Network into your Intimate Network by getting to know them well, understanding your commonalities, and finding ways you can be helpful to them. Just about everyone gets this next part wrong. When faced with an interesting new person in our Familiar Network, we tend to make one of two fundamental mistakes: talking about yourself and committing conversational cowardice.

Mistake #1: Talking about ourselves.

We go into overdrive to convince them that we’re interesting and likable, too. Most of us have developed the ability to pivot any conversation back to ourselves. After 5-10 minutes of conversation, we know very little about our new friend.

We make this mistake because it feels good. There’s an innate human desire to be appreciated. When we do all the talking, we rob our new friend of the opportunity to perform this essential act. How did you feel the last time someone you just met kept talking about how wonderful and successful he is? You likely developed, at minimum, a low-grade envy and dislike for this person. What a sad missed opportunity. We expend all this energy trying to get someone to like us, when all she really wants is the opportunity to get us to like her.

So don’t talk about yourself. From now on, use every interaction as a chance to appreciate someone else by investigating their work and interests. “How long have you been doing CrossFit? What are the results? As a vegetarian, is it hard to get enough protein to support all that weight lifting?”

Approach conversations with the mindset of a batting practice pitcher in your new friend’s home run derby of personal greatness.

Avoid temptations to talk about yourself by pivoting their questions about you back to them. Watch how eagerly this person takes the chance to tell you more about his or her passions. As famous adman David Ogilvy said, “If you want to be interesting, be interested.”

Mistake #2: Conversational cowardice

We also tend to keep discussions safe and limited to the surface. Small talk is a fine way to break the ice with your Unfamiliar Network, but you’ll never get to know someone until you move into conversations of substance. Consider the difference between these two interactions with the same person:

Exhibit A

“Have you enjoyed the event?” “Oh, yes, it’s very nice.” “Do you go to many events, Margaret?” “Three or four a year.” “How nice.” “Yes, it’s nice.”

Exhibit B

“So did you hear anything at the event relevant to your work, Margaret?” “The piece about consumer drone tech was interesting.” “Do I remember right that you work for a defense contractor? How do small drones fit into the broader national security picture?” “Oh, it’s a big deal. Imagine a network of internet-connected drones…”

With the first approach, we learned that we both thought the event was nice; in the second we got to learn all about cutting-edge new technology. We are often afraid to have deeper conversations because we don’t want to look ignorant about things we don’t know about.

“Todd, you said you work at a Swiss bank — what do you do there?” “Debt capital markets.” “Oh, cool.”

And then you spend the rest of your life not knowing what debt capital markets are and what your new friend does for a living because you’re too afraid to ask. But if Todd is worth getting to know, he won’t care that you’re not familiar with his work. He will probably take your silence to mean you’re not interested in him. So why should he bother getting to know you? Liberating yourself from this fear will open the door to thousands of fascinating conversations.

Here’s a set of questions that are always applicable to someone’s work, and that will encourage them to open up more:

  • Tell me about the business model — who pays whom and who is delivering value to whom?
  • What advantage do you offer over your competitors that get customers to choose you?
  • What drew you to work in this particular industry?
  • How big a piece of the overall business is your division?
  • Are there new technologies affecting your business?
  • It sounds like you’ve been successful? What makes someone unsuccessful in the role?
  • What’s your favorite part of your job and why?

Now that you’ve gotten into mutually fulfilling conversations, each subsequent time you connect, there’s a flywheel effect. You can get more detail and ask more insightful questions: “How have you been, Todd? I just read in the Financial Times that bond prices have been erratic, did that affect you in any way?”

There’s another hidden benefit of this approach: you become more knowledgeable and interesting to other people based on all the fascinating things you’re learning from your new friends, and you never know where the knowledge you glean might come in handy.

Your success at building a network is founded on one very important mindset: that you’re doing it based on your desire to know, appreciate, and help other people.

Read Steib’s tips on how to bring people across your Familiar, Intimate and Meaningful Networks here.

2. Tune up your follow-ups — and make them a part of your routine relationship maintenance.

Once you’ve made a strong first impression, it’s up to you to turn that one touchpoint into a connection that has mutual purpose and positive impact. Chris Fralic has found that this is where a lot of people fumble: They get too busy, disorganized, nervous or pessimistic to follow up the right way. The result: too many high-potential relationships fizzle for no good reason.

Fralic’s responsible for First Round’s investments in Warby Parker, Roblox and HotelTonight (now acquired by Airbnb), among others, and he’s penned a landmark Forbes piece on nailing email introductions. He attributes his professional success to the thesis on networking he developed as a young man selling Oracle software:

The best way to be highly influential is to be human to everyone you meet.

With that mantra in mind, he shares two simple tips for the care and keeping of professional relationships.

DO: Follow up and follow through

It sounds so easy — just follow up after meetings and complete any deliverables you promised. But a shocking number of people don’t, Fralic says.

Actually doing what you say you're going to do will put you in the top quartile.

“I met with Kenny Herman, who used to work for a First Round company and is one of the best business development people out there. In a meeting, he kept coming up with ideas for people to introduce me to and said he’d send over a list that I could choose from,” Fralic says.

“Afterwards, he actually did send me an email with LinkedIn links to all of the people he’d brainstormed and one-line details on who they were. With it came a short note offering to make introductions. That's the perfect follow up. Nine out of 10 people don't do that. Instead, most people just drop off or forget. Not only does the relationship stop there, but I’ll never use the word reliable to describe them.”

These days, there’s tons of chatter about building one’s personal brand. Ironically, your brand actually comes from you doing great, consistent work on time — not from investing in social media or a website or marketing your work, says Fralic. You have tools at your disposal to surprise and delight: speed and polish. If you can follow up fast, that’ll get you noticed — even better if your content is perfectly proofread and detailed.

DON’T: Reach out only when you need something

Furthermore, make sure your follow-up is valuable, not solely a series of requests. This can happen by accident, or if you feel like you have no other choice.

“Check your ‘Sent’ folder to see when’s the last time you reached out to someone and in what context before you fire off that note asking for help,” Fralic says. “It becomes obvious very quickly when someone just wants to use you. Don’t be one of those people. This is a quick way to suffer single-digit response rates. If you’re just asking people for things without thinking about what you’ve done for them recently, or without any context for why you’re asking, people will feel imposed upon. And they won’t respond. Your reputation takes a hit and everybody loses.”

Christ Fralic, board partner at First Round

Read more of Fralic’s manifesto on how to become insanely well-connected here.

3. Set the stage for opportunity by making “low-lift value payloads” a habit.

A strong network can be your eyes and ears in the field when you’re looking for a new opportunity. Patrick Ewers, early LinkedIn director and relationship-building expert, breaks down the anatomy of an opportunity: “Opportunities come to you because someone was thinking of you at the exact time they came across something that was relevant for you — whether it’s a job, or a deal, or an introduction, or a technology that could help your business.”

You can't control when people see great opportunities. But you can make sure they think of you first.

“I call this the notion of mindshare — how top of mind you are for someone at any given moment,” says Ewers. “The more mindshare you have with someone, the more likely they are to say, ‘I know the perfect person for this opportunity.’ You want to empower people to think of you when they come across needs that you can meet.”

That doesn’t mean forcing frequent interactions, but rather focusing on high-quality, relevant and valuable interactions. “If you can do this, you’ll constantly win,” Ewers says.

It’s easier than you think, too. “You don’t need to be investing a ton of time determining how to be valuable for people. No one expects this. We all have day jobs,” says Ewers. “This is where people struggle the most, they don’t know how to break things down into lightweight actions.”

It is possible to deliver awesomely high value to people at extremely low costs to you.

This is usually just a matter of changing your behavior during in-person interactions (i.e. focusing more on others’ needs), and adding one simple habit: low-lift value payloads.

“I love the term value payload because it sounds so tangible,” says Ewers. “Value payloads are anything you provide to people that could help them — even if it doesn’t pan out, 90% of the perceived value is intent. They could be introductions to people they want to meet, articles about a problem they are trying to solve, a note saying you saw their work and sent it to someone else. Most of the time it requires sending one email, which is easy to make a habit.”

Whenever you take this type of action, you’re telling someone, “I thought of something very specific to you and did something about it.” It’s hard to imagine that going unappreciated.

“The easiest value payload — it literally costs you nothing — is the emotion-based value payload,” says Ewers. “All it requires is giving people positive feedback in the moment. Many people have this odd tendency to be overly careful when giving out compliments or positive feedback. How often is someone talking in a meeting and you think, wow that was really smart, but you never say it out loud? Or even to them after the meeting?”

To change this mentality, he has one simple rule people can apply to ramp up the value they deliver across the board:

If you think it and believe it, say it.

“If you really believe something positive about someone else, you have nothing to lose. You can stand by it, and it will make them feel good, especially if it’s expressed in front of their peers. Just like dashing off an email to someone, this is easy enough to make habitual if you try.”

As granular as these tasks are, Ewers says he rarely sees people taking advantage of them. “It’s a function of being human. We’re not hard-wired to take risks. We react 5 times as strongly to negativity as positivity, so we don’t want to risk even a small chance of rejection, even if we’re trying to help someone else.”

He has talked to a number of people who say they are so anxious at work that they don’t have the time or awareness to even offer positive feedback. But, as Ewers says, this makes it an even riper opportunity. Just think how soothed and delighted someone else who is as anxious as you will be if you say something nice about them. It has the potential to vastly improve their work environment.

Other people fail to deliver value payloads because, whether they know it or not, they see success as a zero-sum game. If someone else succeeds, they feel less successful. To be an effective networker, you have to be honest with yourself and ditch this belief immediately. Replace it with the tenet that making others successful will do the same for you. It’s not only more positive, it’s more accurate.

Aside from this, there are two things you can do to strengthen connections and supercharge your value payloads:

  • Establish common ground: This might sound like common sense, but there’s some powerful science behind it. Everyone has this instinctual urge to be part of a tribe, and out of that comes an “us” vs. “them” dichotomy. “Whenever you interact with someone, you want to end up in their ‘us’ bucket. You want to be part of their tribe,” Ewers says. Fortunately today, this is as inconsequential as saying you like the same app or read the same blog. “When someone hears this, their reptile brain makes a calculation that says this person is like me. And research has shown that thinking 'I am like you' instantly translates to 'I like you.' It’s how we process likability."What’s your favorite part of your job and why?
  • Be authentic: Replace “fake it till you make it” with another mantra. “Instead of faking confidence, be genuinely curious,” Ewers says. “When you’re curious, you’ll ask people about themselves. You’ll find out what they want and how you can meet their needs. People love talking about themselves, and they love people who love to learn. It’s more honest and you’ll make a better impression."

4. Take 10 minutes a day to craft casual hellos — it goes a long way.

Luckily, creating “low-lift value payloads” doesn’t have to be a Herculean undertaking. And according to Karen Wickre, tending your network doesn’t take more than 10 minutes a day. The key to making meaningful connections, she argues, isn’t going to a marathon of cocktail hours. It’s staying in “loose touch” — what she defines as “the care and feeding of your networks over time.”

As the former editorial director of Twitter, Wickre is both incredibly well-connected and a self-described introvert. She even wrote a book for her fellow quiet, limelight-avoidant observers. In Taking the Work Out of Networking: An Introvert’s Guide to Making Connections That Count, Wickre shares a 10-minute trick for maintaining loose touch, and five FYIs you can send keep your relationships thriving.

Karen Wickre, author and former Editorial Director at Twitter

Here she is in her own words:

No one likes to feel used repeatedly, especially when it’s one-sided. The best connections you can make are those where you have mutuality: sometimes one of you needs something, and sometimes neither of you does, and you continue to give your time and attention either way.

This is my guiding principle for no-pressure networking: Nurture it before you need it.

Start by spending 10 minutes a day building your loose-touch habit. That’s a small amount of effort for what is potentially a lot of payoff, in good feelings if not in immediate outcomes. Whether you’re the giver or the receiver in need, you’ll get a sense of satisfaction either way. Here’s how I fit it into my day:

  • Make it a morning warm-up. My morning ritual of checking email and my news feeds is a way to limber up for the workday. As I scan the headlines, I’ll share a story or two that I know are of interest to people I haven’t been in touch with along with a short note: “This made me think of you. What’s your take? And how are you?”
  • Keep a running to-do list. Part of staying in loose touch is simply following up on encounters you’ve had. After your conversation or meeting, think about what you wanted to pass along, and who came to mind that you’d like to reach out to. Add them to your list and get the satisfaction of crossing that task off later.
  • Close out the day with gratitude. Send out a couple of “thinking of you” notes to people you’ve enjoyed meeting or would like to catch up with, or to even start a new conversation with someone you’ve just met. It’s a nice way to plant the seed of connection that might yield a response as soon as the next day.

Use these five FYIs to say hi.

The nice thing about a “Just FYI” message is that there’s no real obligation involved on either side, and you are top of mind for a moment with the recipient (which helps solidify your ongoing relationship).

Apart from the link or attachment, your message is essentially along these lines: this confirms what we talked about; I wonder what your reaction is; reading this reminds me of you. Here are five types of ‘Just FYI’ notes to add to your rotation:

  • 1. Send a relevant article to someone who interviewed you for a job you didn’t get. Even though it didn’t work out, you liked that person you met, and want to stay in touch. Show that you’re a good sport and still attentive to the company and industry. (Just don’t revisit the job interview.)
  • 2. Say hello to someone you met at a conference last year with the just-published agenda for this year’s event, asking if they’ll be attending.
  • 3. Share interesting news about your old company with a former colleague. Former coworkers are sometimes the best weak ties — you may not have known them well, but there’s a feeling of kinship. A simple note asking what they’re up to along with a story can keep the connection going, or even strengthen it.
  • 4. Show you’re paying attention to your weak ties by sending them items (news, event, commentary) related to their interests. For someone you don’t know well, this will give a moment of delight and appreciation. What you send is based on what you know: are they presenting at a conference, doing research, passionate about a project, focused on an emerging trend?
  • 5. Reinforce a connection you just made by following up with relevant information. If you just met someone and talked about mobile phone usage, send the news story you spotted on this with a brief note (“This made me think of our conversation”).

Here’s an example of a no-obligation “Just FYI” note I sent recently to a friendly professional contact in the field of autonomous cars. I thought of him after seeing a tweet about an upcoming workshop on that topic.

Subject: Do you know about this conference? (The subject line should tease the information you’re sending instead of being a generic “hi”.)

Hi Jimmie, I hope you’re faring well in these fun times. Just ran across this [link] and thought of you.

Happy Monday,


Even this short note accomplishes quite a lot:

  • “Fun times” is a reference to the surge of news about autonomous cars, which is sometimes wacky, negative, or inaccurate. This mention conveys a bit of sympathy about what Jimmie deals with.
  • You don’t have to explain a lot if you include an informative link. In this case, it was the home page for an upcoming workshop for policymakers working on issues surrounding self-driving vehicles. Note that it was the site for the event itself, not a news story about the event — the former is more useful and direct.
  • Even the closing line, “Happy Monday,” says “I’m not looking for anything from you. Do what you like with this information.”

Read more of Karen’s highly tactical advice on how to make connections that count, from a Silicon Valley veteran and introvert.

5. Vanquish the fear of rejection — and embrace possibility instead.

When it comes to cold outreach, the anxiety that commonly plagues the networking-resistant is the fear of rejection. The enthusiastic pitch email gets drafted, and the cursor hovers over the “send” button... only to back away at the last moment.

As someone who’s pitched creative work in the past, Liz Fosslien is no stranger to the feelings of fear and doubt that often holds people back from hitting “send.” In 2014, the current Head of Content at Humu started working on a side hustle: a little volume of her sketches and gathered career wisdom that eventually turned into her bestselling book, No Hard Feelings: The Secret Power of Embracing Emotions at Work.

She offers the flip side of rejection: “There’s a rush of emotions you feel when you make that leap. Instead of letting the fear of rejection hold you back, let the possibility motivate you,” says Fosslien. She offers two tactics for pushing past the fetters of fear and embracing the promise of putting yourself out there.

Pitch yourself as a human being

As a low-stakes way to start making connections and publicize her work, Fosslien emailed three economics bloggers that she admired. “I approached them as someone who followed their work and was excited about economics. They ended up reposting my illustrations,” she says. Eventually, one of her projects, 14 Ways an Economist Says I Love You, was circulated among publications including The Financial Times and, of course, The Economist.

“Don’t be afraid to be honest about your admiration over email,” she says. “Open up by saying, ‘I love your work for X, Y, and Z reasons. I did this thing that I think you might like. If you enjoy it or want to repost it, I’d be thrilled,’” says Fosslien. “That’s it. Pitch yourself in a human way, and you’ll find that people will often respond to that authenticity.”

My advice for putting yourself out there is: Just send the email. Don’t overthink it. The best-case scenario is that it opens an amazing door for you. The worst thing that can happen is that nothing happens.

Share your works in progress

If you’re working on a personal project, you don’t have to toil away in solitude and emerge, years later, with your one masterpiece. Share your sketches and doodles along the way, too.

“Whether you’re working on a side hustle or assembling a portfolio, take the smallest piece of output and put it online somewhere,” says Fosslien. “Or even document the process in a low-lift way with a blog, or photos.”

The benefit of leaving artifacts of your creative work is twofold: “First, you get the project outside of your own head, so you can process it a little more objectively. Second, you have physical evidence that you can share with others,” says Fosslien. “While I was working on the book, I’d sometimes show my partner semi-completed illustrations, both to get his feedback and for the little boost of motivation when the drawing made him laugh.”

See more of Fosslien’s tips on the seven deadly emotions we encounter at work (and how to make them your secret career superpowers)

6. Add some strategy and direction to your coffee chats.

The coffee chat, or the informational interview, is one of the best-known tools in the networking toolkit. But most people underestimate the careful preparation it takes to set them up for success. Even if you do land the spot on a new contact’s calendar, it can be easy to let the chats meander aimlessly — effectively wasting your and your contact’s precious time.

You might say that Sasha Orloff has some expertise on the art of the coffee chat. Over the course of a few months, the founder and former CEO of LendUp had 100 coffee chats with founders, CEOs, entrepreneurs, investors, coaches, executives and other business leaders.

Sasha Orloff, founder and former CEO of LendUp

Here’s how it all began: When Orloff decided to step down from his position as CEO of LendUp, he took a hundred-day hiatus to reset and reflect. By the hundredth day, he was ready to start exploring something new more seriously, which meant activating his network to mine for opportunities.

One tactic that helped Orloff generate inbound leads was crafting a short LinkedIn post that announced his departure. His post, which was initially meant as a simple update, led to a pile of responses and requests to connect. “If you share with your network that you’re moving on, folks might naturally reach out to ask after you, or to offer their help,” he says. Orloff’s vulnerability ended up leading to greater opportunities.

At first, Orloff said “yes” to everything. Before long, he focused on prioritizing meetings that could help him think about his next steps. So, he set a goal for his coffee chats. “I wanted to ask people how they managed transitions from one job to the next,” says Orloff. “I also wanted to focus on talking to people who would help me find inspiration about new ideas and new problems to tackle.”

Here’s how Orloff strategically narrowed his contacts list:

  • Inbound contacts: “Some people reached out after I announced my stepping down on LinkedIn. That ranged from colleagues who wanted to catch up and reflect on our time at LendUp, to friends.”
  • Operators who had been in his shoes: “Here’s where I got more tactical: I focused on people who had been in my situation and would be able to give me guidance on how they navigated their own transitions. I reached out to CEOs I was at least loosely connected with. I prioritized people who had left the company they had founded, or had taken over as CEO after the original founder.”
  • Investors: “While I viewed my own career transition at close range, VCs have a unique perspective. They have an aerial view on these situations, and they’ve seen and analyzed plenty of them, too. I thought they’d lend a helpful perspective on the market and opportunities and what that might mean. So, I started with my own investors in LendUp. I also wanted to ask them how they thought about the market and what new opportunities there might be.”

As Orloff gained more perspective, his vision for next steps came into greater focus. At this point, he realized that before he could leverage his network, he had to be able to succinctly articulate what he wanted.

People want to help, but they can only help so much if you yourself don’t know where you’re headed. With a more specific objective, you can much more effectively maximize your network,” he says.

In order to get to further hone in on his own goals, Orloff made three lists, under three major buckets:

  • Skills you want to build
  • Industries you want to work in or experiences you want to have
  • Non-negotiables

“Once you’ve listed this out, you should be able to articulate what you want in one sentence: Once you can tell people, ‘I’m interested in exploring role X in industry Y, and my must-haves are Z,’ then it will make it much easier for your network to help you get to the place you want to go,” says Orloff.

Read more about the career wisdom on transitions that Orloff learned over 100 coffee chats.

Photography from Getty Images, Michael George, Helena Price and Bonnie Rae Mills.