How to engage social selling prospects – 4 techniques & real examples

By Ollie Whitfield, Social Selling Executive (@OllieWhitfield_ ) My process for social selling starts with the time spent prospecting, finding who you want to reach out to. Are …

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By Ollie Whitfield, Social Selling Executive (@OllieWhitfield_ )

My process for social selling starts with the time spent prospecting, finding who you want to reach out to. Are they socially active? Are they the decision maker, or at least in their team or downline – a change-maker if not a decision maker. Once I have found my prospect, they are added to my CRM so that I can keep track of the interactions and engagements I have had with them. Finally, it’s now time to get on social and get some interaction going with your prospects.

It’s easy to say “go and engage with your prospect”, and for some it comes naturally. For others, especially people new to social selling, there is confusion as to how and where you should do it.

I’m going to share my methods, tactics and hacks that I have learned from leaders in the social selling field – Jack Kosakowski and Kevin Thomas Tully. I’ll use them as examples too…

Personal connection

I find it is easier to engage with someone on a personal level, compared to on a professional level. This is for the simple reason that people care about their interests, hobbies and what they are doing – we are people before we are professionals. For example, in my Twitter bio I explain I am a Liverpool football club fan, which is a good nugget of personal information you could use to speak to me about something I care about.

I know Jack Kosakowski is a Chelsea football club fan through his tweets and Instagram posts. See below how I have spotted this in his Twitter feed and crafted a tweet that I made with the intention of making him reply.


I have tried to share my opinion, and ask him to provide his in my reply tweet here. As a Chelsea fan I am sure he believes they can win the league, so I would fully expect him to reply to me saying that. I deliberately made the tweet quite simple, and provocative in that way – not to offend or upset, but to tease and draw out a response from the prospect.

The art of engaging is to actually forget the reason you are doing it, and to talk to somebody in the way you might in person. It is tricky where you must remember they are a stranger, the correct tone is important. You can’t go crashing in telling Jack that Chelsea are a bad team and that you wish them bad fortune (if you genuinely do) because as anybody in a face to face situation would do, the prospect can take offence.

They say “be human” and that is so true, spot something that you actually have something to say on. If you don’t like football (soccer), you don’t need to talk about it just because the prospect likes it. If they have not given any indication they like or want to share any other personal hobbies and interest’s information, then use the football topic.

As long as you try to actually be yourself, you’ll be doing just fine.

Professional connection

Sometimes the personal connection isn’t possible and you have to go to the professional connection first. For professional connection, I tend to find a LinkedIn publication, blog post, or curated tweet sharing content relevant to the prospect’s industry.

The example below is a comment I have made on Kevin Thomas Tully’s LinkedIn publication The Only Simple, Scalable Social Selling Workflow You Will Ever Need


There are 4 small but key techniques I have used to make Kevin want to reply to my comment and notice me:

  1. Praise – everybody likes it
  2. Tagging – to get noticed you need to give the person a notification, commenting is one, tagging them creates another
  3. Opinion and feedback – My opinion is what makes me different to others, so sharing it is a good way to build the connection between the two of you
  4. Question – asking an insightful question is a good way to get a reply, questions need answering

Alternate engagement

The principles remain the same across social media. The 4 techniques I used to comment on Kevin’s LinkedIn post are key and should be used across any other social channel you want to engage your prospect on. For example, Jack and Kevin both use Instagram daily. I often leave a comment using the 4 techniques outlined above on their posts. The same can be done on YouTube or Facebook, which of course is quite similar to LinkedIn in how you can like and comment on posts.

To tell the truth, the only reason I use these 4 techniques is because they are the polar opposite of how I feel the seller is acting when I am cold called. Cold callers get a lot of negative press, but it’s really their company who it should be aimed at, and even then, if it’s working for them nobody can knock them. What I’m getting at is, keep in mind the right techniques for speaking to your buyer in the way they want to be communicated with. Many, many businesses and people are now loving social media, and that means social selling has become very, very big. The 4 techniques really are applicable to any form of sales, but work so nicely in social selling.

It all starts with a tweet, comment, or share!

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    […] in sales or marketing today. The best marketing has shifted to include an outbound strategy, using engagement to create 1-1 conversations proactively vs reactively. Modern sales teams are no longer going all-in on cold outbound activity […]