How I Get 1 out of 10 LinkedIn Connections on The Phone


High on the list of entrepreneurial expletives. It’s uncomfortable, intimidating, and stigmatic. Getting started, sales was almost as uncomfortable to me as speaking to an acquaintance in the grocery store and then trying to avoid eye contact with them for 3 or 4 aisles after saying goodbye.

Like, seriously, how can any one but myself need both a cheese grater and anti-hairball cat treats.

Dirty word though it may be, sales are VITAL to any business in a growth stage, especially early startups. The bottom line is that B2B companies who don’t have sales just don’t get business. At least, not the kind they really want.

Take, for example, your average single bar-goer. He can wear nice clothes, drive a cool car and master the effortless-just-out-bed-woke-up-like-a-catalogue-model hairstyle, but if he doesn’t ask his dream girl out, he’s never gonna get the date.

The same applies here. You can build an awesome website. You can put out great content. You can write copy like a mofo. But unless you’re reaching out and asking for connections to your ideal clients, you’re getting a lot less business than you should, and probably not the kind you’re looking for.

Enter LinkedIn.

Yes, I said LinkedIn. That awkward platform that tried to be Facebook for professionals, yet somehow has an even more childish and meme-filled newsfeed. If you can ignore the poorly-lit happy hour selfies and some objectively untrue political memes reminiscent of your grandmother’s chain emails, there is actually a lot of value in LinkedIn’s best feature: search.

I’m going to take you through the steps I refined to get 1 out of every 10 of my new (cold) LinkedIn contacts on the phone. These phone calls were intimidating in the beginning, but I made some incredible connections through them. I spoke to people on the other side of the world, closed clients on the opposite coast, learned a lot about who I thought my ideal client was, and even ended up giving people MY business! One connection liked my info so much that they asked me to speak at an entrepreneur event in Costa Rica. You never know what sorts of opportunities might show up.

The Process

1. Search.

First thing’s first. Acquire your target. You’re going to need filters from the Advanced search feature so you may as well start there.

Search 2nd/3rd+ connections only: this keeps people you’re already connected with from showing up in your search results. That being said, if you haven’t reached out to current connections yet – maybe you should start there!

Use Boolean searches: LinkedIn uses powerful web-browser search features like “AND,” “OR,” and “NOT.” These can save you a lot of time and keep you from configuring and saving 16 different searches.

  1. OR: Helpful when there are different ways to phrase what you’re looking for. Maybe your targets will use “funding,” or maybe they’ll use “investing.” By searching “funding OR investing,” LinkedIn will show you both.
  2. AND: Use when you need multiple terms. If you want a startup investor, you can search “investor AND startup.”
  3. NOT: Can’t be used by itself, but is great for filtering out people you don’t want to see. If searching “investor AND startup” brings me a lot of people from Fox Rothschild, which is a firm I’m already connected with, I could search “investor AND startup NOT Fox Rothschild.
  4. Parenthetical searches: Now let’s get crazy. You can combine these options with parentheses in one search. For example, “(funding OR investing) AND (startup OR entrepreneur) NOT Fox Rothschild”

2. Connect.

Sweaty palms be damned, it’s time to hit that connect button. This should go without saying, but before you get here, make sure your profile is up-to-date, professional, and you have a decent photo. Don’t be a weirdo.

Also, NEVER click connect from the search page. It doesn’t allow you to customize the message. It also means you didn’t take the time to browse their profile and see if they’re actually who you think they are. Shame on you.

Take a few minutes to look at their profile. The first thing you’re looking for is a connection/communication policy.

Some people (rarely) will actually put right at the top of their profile that they won’t accept connection requests from people they don’t know. Close tab, end game, don’t pass go. This person will not think you’re being plucky if you send a request anyway. At best, they will ignore you. Even worse, they may flag you as someone they don’t know. Enough of those gets you put in LinkedIn jail as a spammer. Don’t be a spammer.

On the other hand, some people will say straight up that they connect with anyone. Some of these folks will add “LION,” which is a strange cultish acronym for LinkedIn Open Networker. I’ve even seen some people go as far as to put a Calendly link right in their summary for you to schedule a call right from their profile! Personally, I would follow protocol as opposed to going straight for the kill, but that’s up to you. You already know this person is going to be more receptive.

While you’re browsing their profile, see if there’s any way you can connect personally. Read: DO NOT cyber stalk these people. I’m not asking you to find out where their mom’s hairdresser went to college. Just browse their page and see if there’s anything you could bring up as a personal connection. Maybe they went to the same school. Maybe you used to work for sister companies. Maybe, as in one case with me, you were both really into guitars. Anything that makes you more of a kindred spirit is a good find.

Also, see if there are any mutual connections. The more people you connect with, the more likely mutual connections will be. Unless you have permission, don’t say that you were referred, and you don’t have to go crazy emailing your mutual connections before requesting. A quick “hey, I saw we had some mutual connections,” is one step closer to familiarity.

Lastly, and most importantly, see if this is someone you’re actually interested in. Sales is somewhat of a numbers game, but increasing your numbers with dud connections is going to be a waste of time. Only send connections to people you think may add value to your network.

Once you’ve crossed all those Ts, go ahead and send a connection request from their profile. Always customize the message with something friendly and personable.

3. Track

I’m a number person. I get positively giddy when I get a chance to build a spreadsheet of shit like this. YOU don’t have to track things to the extent that I did, but my Google sheet is >>here<<, just in case you want to.

Even if you don’t track everyone that you’ve sent a request to, you should have a list of people who have accepted. One low-effort way is to keep these in your email inbox. If you go to Privacy & Settings > Communications > Email Frequency > Invitations Details you can set your preferences to email you with each individual person who accepts your invitations (otherwise it only sends you “recommended” or group notifications). This way, every new connection is in your inbox so you can take action on them individually.

4. Ask

Now the real fun begins. Email outreach.

For me, this meant a 3 – 4 email sequence that asked for a quick phone call. I sent the very first email a few days after they accepted. Then I sent follow-ups every 3 business days or so (Tuesday – Thursday are actually best for getting responses) until I decided it was time to call it quits. Then, I ended it with a friendly sign-off and an open invitation to get back in touch if they changed their mind. It’s VERY important not to act sassy or snubbed. I can’t tell you how many people would email back after that last message with something like

“I’m so sorry, I’ve just been so busy! I was meaning to get back to you – would this Thursday work for a phone call?”

Ultimately, these messages should take on your own style and personality, but I’ve put together some scripts that I found effective.

get the email scripts

The Tools

The great thing about this system is that it’s completely scalable to your workload. If you’re only sending 10 or 15 requests a week, you may not need these tools. As you start scaling up, though, it will save you a lot of time to automate some of your steps.

Excel/Google Sheet

Cheap. Easy. Your best friend. In case you missed the link above, >>here<< is the template I used.

GMail Canned Responses

Another godsend. Canned responses are a beta feature in the Labs settings in Gmail. You can create each of your messages with placeholders for name, company, personalization, etc., and pop them in for each email you send out. No Ctrl+C / Ctrl+V or forgetting to change the recipient’s name before hitting send (been there… super embarrassing).

LinkedIn Sales Navigator

You can use this system with the free version of LinkedIn. No problem. If you’re looking for a boost, though, LinkedIn Sales Navigator might be what you’re looking for. It has the benefits of unlimited 3rd+ connection searches, it allows you to see everyone who has visited your profile, and it has a pretty cool back-end module that allows you to tag and track people as leads. I used Sales Navigator when I was really going HAM with the LinkedIn networking, but I’ve dropped it since my outreach has slowed down.


A souped-up addition to canned emails. Gmass not only allows you to use templated messages, but it also automatically sends your follow-up messages for you. You can send the original message and schedule follow-ups with X amount of days in between. If you really want to go crazy, you can connect it to a Google sheet with your recipients and it will send it to whichever rows you tell it and customize your message with meta tags like [NAME], [COMPANY], or [PERSONALIZED INTRO].

I used Gmass back when it was free, but they switched to a paid model. At the moment of this writing, the subscription with auto-follow-ups is $12.95 per month.


The big guns. If manually customizing and sending connection requests is creating a bottleneck, LinMailPro can do it for you. You’ll need to have a premium version of LinkedIn, and I still recommend you browse each profile you plan to send to. If you use this app, however, instead of inviting, you can add each profile to a queue and then sent out a long list of connection requests at once.

Another warning about LinkedIn flags – if you’ve never sent more than a few requests in a week and all of a sudden send 50 in one afternoon, you WILL get flagged. Gradually increase the number of people you reach out to, and don’t take it past 20 or 30 per day.


Not gonna lie, this process can get time consuming. It will also be uncomfortable in the beginning. I have slowed down from this type of outreach substantially, but it was an incredibly growing process for me, and I made connections that I still collaborate with today.

Step out of your comfort zone. Ask the girl out. Get the business you’re actually looking for!

Your Thoughts?