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The Winning Approach to Outbound Lead Generation

By Tzakhi Freedman

The moment when you first make contact with a potential lead can make or break your relationship with that person. Whether you’re reaching out via email, LinkedIn, or another platform, it is so important to have a clear and direct ask. Being transparent about what you are looking for sets you up for a productive conversation with your leads, rather than causing confusion. 

Because this initial ask is such a pivotal moment, it’s very important to take your time when crafting this initial message. Here’s what you should say to put together an effective ask – and what you should avoid.

What Not To Do

Before we discuss how you should approach new prospects, it’s important to understand what you shouldn’t do. Many of today’s sales “experts” will recommend that you start a casual conversation with a prospect and try to build a friendly connection with them before telling them what you’re looking for. They often recommend searching for a commonality to discuss, such as a shared alma mater or former employer. Sometimes they even recommend that you find a post they liked or commented on and use as a reference to start a conversation.


Another potentially misguided strategy that many people use here is offering “hooks” like a free video or PDF to their prospects. While this can work well as an inbound lead generation strategy, it’s not going to be successful with outbound lead generation where you already have the prospect’s contact information. It ends up reducing your conversion by adding an unnecessary buffer between you and your leads. What’s worse, sending a free piece of content  assumes that the recipient has the time or desire to use these free items, which is unlikely to be the case. 


These experts often compare business relationships to social and personal relationships. The logic behind this is that if you were looking for a new friendship or relationship, you wouldn’t approach them out of the blue on the street. Instead, you would get to know them first in a social setting. However, this just doesn’t apply in a business setting. Business professionals expect to receive sales pitches and might take interest if the offer is relevant enough. They don’t expect to get into an unfocused chit-chat with a total stranger. 


Most businesspeople and high-level employees are busy managing their careers and working toward their goals. If you approach them with casual or vague questions, it assumes that they have the time or energy to spend talking with you, which they might not. You also aren’t giving them a chance to efficiently qualify themselves as a lead. It’s very possible that they cannot buy your product or invest in your company, but you won’t find that out until you let them know exactly what you are looking for.

How To Write A Successful Ask

Instead of using this circular approach, it is much more effective to be direct. You don’t need to ask your prospect to make a purchase or investment right off the bat, as this can come on very strong. Instead, politely introduce yourself, thank them for their time, and let them know exactly what you are looking for. Be clear and specific, and avoid vague pleasantries whenever possible. Finish out the initial message by asking them if they are interested in learning more. Don’t be rude, of course, but show that you are a professional by getting to the point quickly enough so that their time isn’t being wasted unnecessarily.

If this prospect isn’t interested, they may simply refrain to respond even after a follow-up email or two. At this point, they’ve indicated that they aren’t a good fit, and you can move on to other prospects. However, if they are a good fit, it’s very easy for them to respond and you can both move forward.

Increase Your Chances With Proper Preparation

To increase your chances of finding a good match, make sure that you’re doing your research beforehand. Before sending a message, find as much information as possible about your prospect online. Look at their LinkedIn and any personal websites they may have, as well as profiles on other sites like CrunchBase and AngelList.

The more you know about your prospects, the easier it will be to determine if it’s a good match rather than just guessing. This can also indicate which platform is going to be most effective. For example, if they aren’t on LinkedIn much, reaching out via email may be a better technique.

It’s also important to make sure you’re presenting yourself in an effective way. Give your email or LinkedIn message a clear title that indicates what you will be discussing. You should also make sure your LinkedIn and other online profiles reflect what you’re currently working on. Think of it as a form of courtesy. Make it easy for your prospects to understand what you do and what you are after, so that they can easily and quickly decide whether they are interested to engage with you. This will save time for your prospects, as well as for you

Final Thoughts

Putting together an effective ask starts with doing your research to make sure you’re targeting the right people. Once you’ve found an interesting prospect, it’s important to be clear and direct. Not only is this a more effective strategy for generating leads, but it also shows that you respect the recipient’s time.


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