The Fine Art of Cold LinkedIn Prospecting

The Fine Art of Cold LinkedIn Prospecting

The most important thing throughout this process is personalization.

What do you do when you find a prospect on LinkedIn and can’t get an introduction? Do you give up based on the seemingly vast digital distance?  Or, do you have a strategy for building cold relationships on LinkedIn and transitioning them into real-life business opportunities?

We’re going to share with you our three-step strategy for taking your LinkedIn prospects from freezing to warm.


The "Commonality Connection Request"

Run Advanced Searches on LinkedIn to not only find people who fit your ideal prospect profile, but who also have commonalities with you.  If you went to University of Michigan, search for Alumni. If you used to work for a tech company, search for people with a similar career.   If you are an avid cyclist, search for the keyword “cycling.” 

Personalized Connection Request

Now you are ready to send a personalized invitation to connect to your cold prospect.  The keyword here is – personal. So, scrap the generic “I’d like to add you to my personal network” language. Remember, you are reaching out to someone you’ve never met.  Your goal is to start a conversation based on a commonality:

  • Mutual contact
  • Alma Mater
  • Location
  • Work history
  • Hobbies/Interests
  • Charities
  • Groups

You only have 300 characters to work with, so, keep your invitation short.  If you cannot determine a commonality, mention at least one specific item from their LinkedIn profile.  For example, if you notice they spent 20 years at Pfizer, mention it. This tells the prospect that you aren’t just machine-gunning connection requests. 

Here’s an example:


I know we’ve never met before, but I noticed we have multiple connections in common, including John Smith – he’s a great guy.  I also see we both went to UCLA. Want to connect on LinkedIn?


Build Rapport Through Brand Expressions

Once your connection request is accepted, your focus should shift to building rapport. Nothing is more annoying than someone who connects and immediate pitches. Look for opportunities to naturally engage your prospect.  We like to refer to this concept as “brand impressions.” Essentially, these are actions you take that increase a prospect’s awareness of you.

Think of “brand impressions” as a point system. Every time you create awareness about yourself and services, you earn a point.  Your goal is to accumulate enough points to increase the probability of your prospect having a business conversation with you (Step 3).  Think 4-6 points as a general rule.  Here are a few easy “points” you can score:

Send a “Thank You” Message

The moment your prospect accepts your invitation to connect, immediately follow-up with a short message thanking them.  Why?  The fact that they accepting your invitation is reason enough to reach out and generate some awareness.  Also, very few people do this!  You’ll immediately differentiate yourself from the pack. 



Thanks for adding me to your network. I look forward to chatting at some point.



View their Profile

Next, your objective is to view the prospect’s profile in transparent mode a few times (so they can see you’ve viewed them).  This is a great way to create awareness and a bit of mystery.  Assuming they are checking LinkedIn regularly and they have the proper profile settings, there is a chance they see you before you even ask to connect. That’s a good thing.

Send a “Giver” Message

After a week or so, follow up with another message that positions you as a “giver.”  Essentially, you want to be seen as someone who is a serious relationship builder. Take a look at the profession of your prospect and determine anyone you know in your network that they might benefit from meeting.  


Thanks again for connecting with me.

I was thinking… you’re in the tech industry and I have a lot of contacts in that field, particularly at Company Y and Company Z.  If you notice anyone in my network you’re interested in meeting, let me know. I am happy to try and make the connection.  That’s what LinkedIn is for right?   



Comment, Like, Share

People are starved for attention on social networks. If you notice your prospect posts an interesting article, you commenting, liking or sharing that article earns a brand impression.  Look for triggers on LinkedIn that give you an opportunity to engage.   You can also send a direct message to your prospect mentioning an interesting post from them.

Send Something of Value

Look for ways to add value without being salesy – this is not your marketing propaganda!  Always be on the hunt for helpful information you can send to them. For instance, if you run across a great article on the state of the airline industry, send it to your prospects who are pilots or frequent travelers.

Post Regularly

Regularly posting on LinkedIn is a great way to earn brand impressions.   Your objective is to post when your prospective client is on LinkedIn.  According to LinkedIn, their most active times are Monday through Friday mornings and midday.  Put out content to your connections on a daily basis – get in their newsfeed.

Close for the Offline Conversation

To transition this digital profile to a living, breathing prospective client, you’ve got to get them on the phone.   If you can’t get a phone conversation, your previous effort was futile. Therefore, the message to ask them to connect via phone is your most important one.  Don’t blow this!

Keep it short, direct and pertinent to them.  Drop names (get permission from your client first!) or examples of other similar professionals you’ve helped.  Lastly, keep your call-to-action easy.  Don’t send a list of times you are available, instead, get permission to call them!  End your request with an easy response question. 

Hi Kathy,

Hope you are doing well.  I’ve been meaning to reach out to you. We’ve helped many business owners, like our mutual connection Stephen Boswell, with their retirement and benefit options.

I was hoping we could chat briefly to see if we can be of assistance.  Would you mind if I give you a quick call this week?  I would really appreciate it.




Our most important advice throughout this process is personalization.  If any of your messages feel like a “copy and paste” you’ve missed the mark and you’ve set off your prospects sales antenna.  This process takes finesse and skill, but with the right strategy, it is highly effective. 


If you enjoyed this article, you’ll love our new video show and podcast The Stephen and Kevin Show.  Submit your question via Twitter or Instagram with the hashtag #AskStephenAndKevin. We hope to hear from you soon! 

Stephen Boswell and Kevin Nichols are coaches with The Oechsli Institute, a firm that specializes in research and training for the financial services industry. @StephenBoswell @KevinANichols

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