There are lots of ways to have success with social selling, and there are a lot of ways to do it badly and actually damage your chances of hitting quota regularly.

Much like regular sales emails and calls, mistakes can be costly but even more so with social where you are playing in a public arena. I have seen some sales reps called out on LinkedIn for sending a very poor inmail with personalization that has gone wrong.

To be fair to them, it was probably an outsourced job but that’s even worse, outsourcing social work and having it done so bad, prospects feel the need to share it.

It’s not all doom and gloom, quite the opposite. But to help bring the level of social selling skill and practice up a notch I wanted to point out 5 key failings that will dramatically limit the success you will have on social.

Bad Preparation

If you read the content I write regularly you will know that I nearly always talk about strategy first. Naturally, I find that you can have a stab in the dark and you might hit something, but the best way to work is to map out the best route to success and plan for how you will get through each stage along the way. Failure to prepare is preparing to fail, as the saying goes.

You MUST know how best to take a conversation with anyone offline. In your sales process and cycle, is there a demo you need the prospect to have? If yes, you MUST have them on a call where you can show them the product at the very least. So plan for this, think about the value you need to provide the prospect with so that they realise the need and value of having a demo with you. What do you have content-wise or even simpler than that, in your brain that you can use to help a prospect toward discovering the solution (yours) to their problem (if it is the right solution of course).

Once you understand what the ideal “CTA” is when you go to take the conversation offline, you can work backwards from that to understand how you will initially engage and warm up the prospect.

Social sellers who do things on the fly, making them up as they go often block their own routes to success. If you do not know what your messaging is going to say, if you do not know what type of call to action you will offer the prospect then you will not provide something really valuable when you go to take the conversation offline. You’ll offer something that sounds logical to you, and sounds like a waste of time for the prospect.


Once you actually have a strategy and goal in place, you need to be productive and get your processes working well.

Tools are the best way to do this. If you are trying to find the people to reach out to, you need LinkedIn Sales Navigator. You must have this to be efficient with social selling. Aside from this you obviously need a CRM which will allow you to track progress with prospects and the touches you make on them both on social and with calls and emails. I am using a great tool, which acts as what I call a “social activity CRM”. It is a twin of LinkedIn Sales Navigator, but works for Twitter only. I like this because I can get emails from LinkedIn when my leads are active and sharing content on LinkedIn, aswell as Nudge telling me that they are tweeting and I can engage them this way too.

It is also a nice tool for making “to-do” tasks that remind me to make another touch on a prospect without me clogging the Salesforce or other CRM with lots and lots of actions like this. Get the eBook I wrote with Jack Kosakowski to find out a lot more on how I use Nudge in my own social selling…

Not having the right tools in your social selling stack will hold back any progress and success you will have.

If your company is not supportive of social selling you do need to make the payments for any tools yourself so that you at least can shoulder the cost and prove management wrong when you succeed. You can pave the way for other social sellers in the team and when other reps see your success, they will be asking management to let them have a try and have the tools you have.

At worst, if you don’t want to pay lots of money there are some free tools and some very cheap ones, which will be worth the investment so that you can get started social selling. Think of it as investing in your sales career and skills, future-proofing.


Salespeople are often given bad press for this, but the numbers and stats in reports that are published so often do show that if you just personalise your approach even a little bit, your success rates go up significantly. For every rep who sends out 1000 emails per day and cold calls 200 people, there is a rep who sends 25 emails per day and calls 2 people per day but has a ton of context for their calls and outreach – and it makes their calls and emails much warmer leaving the prospect in a better state of mind to respond.

One of the most immediate things that any sales person in the world can do to get better results is to not be lazy. It’s do the extra hour in the morning prospecting, make the extra calls after 5PM. Make the 5 minutes less at lunch count when researching before your next call.

This all becomes even bigger when social selling because I can connect with anyone on LinkedIn and get ignored afterwards. People get blank LinkedIn connection requests all the time, actually I find 99% of requests I get are blank without a note as to why the person wants to connect. On the flip side if I wanted to connect with a prospect, I can spend a few minutes looking at their profiles and who they are, what they do and then send a message that is much more likely to get responded to. It’s more likely simply because there is relevancy.


The great thing with social selling is that it’s relatively new. Email has been a practice in sales for a long time now, phone calls even more so. People have worked out how to make a good call, a good email. People are working out even now, how to do social selling really well. There are new features added to the major social networks regularly, which gives you as good of a chance as anyone else in the world to figure out how best to use these features. There is almost a level playing field, where if you email a prospect who has dealt with your company before in some way you could get discarded before they even read a word you’ve written in your email. No matter what you say in your email, your company name is there in your signature and that can be enough to get your email discarded.

With social it is different, you are acting as yourself. It is person to person, not a business person acting on behalf of a business, talking to someone doing the same thing. The personal connection is key with social selling.

That is why I find Neuro Linguistic Programming very interesting. It helps me understand how to make a personal connection, so that I can further a relationship with a person. I can build a relationship with the business later on, but the person comes first.


This is absolutely key, and every sales person should care immensely about this. Of course in sales you cannot throw your pitch out there to as many people as you possibly can manage and hope for success, it will not find you. You do have to reverse your mindset and think first of the prospect and be there for them to help and push them away from problems toward goals and achievement. Your messaging has to reflect this.

I have been reading Hacking Sales by Max Altschuler of Sales Hacker. In the book, he mentions that your first touch is absolutely vital – if your prospect is going to read or listen to anything you have done to help them they will look back to the first touch.

Why are you making contact?

That should be conveyed in the first touch, and that makes it vital.

Again I revert to NLP, this is really helpful for messaging. You can pick up on how your prospect wants to be spoken to. Look at comments they make on LinkedIn and their posts, look at their tweets.

How do they speak?

Are the working away from problems, are they looking toward goals?

This can angle your messaging, and build rapport for you if you simply find this out and tweak what you say to the prospect on your first touch.

Lazy and ineffective messaging is spraying and praying. It’s not personalising, it’s not thinking about how you can do everything possible to help out the prospect. It is, however, thinking about how you want to make them say a certain phrase that will trigger your pitch. It is, how you will call them 9 more times in the week and not want anything other than a date and time for an appointment.

So hopefully you have read this post and not found any of your own practices listed. If you have, please let me know and I will happily give you some advice on how to go about improving your work. If you are finding your social selling is working nicely, still get in touch and tell me what you’re finding works. I’d love to hear from you. I’m Ollie Whitfield on LinkedIn and @OllieWhitfield_ on Twitter.