persistent prospecting

Hello, It’s Me… Again: The Art Of Persistent Prospecting


Do you know what one of the most successful sales techniques is? It’s also probably the most underrated. Pure and utter persistence. Some may call it bloody-mindedness, but the fact of the matter is most salespeople tend not to follow up properly.

Sales guru and icon Chet Holmes stated that while most prospects are not ready to buy immediately, most salespeople fear “No.” It feels icky and goes against every single fiber of our primeval brain. Rejection of any form leads to “social death,” which in the Stone Age meant being cast out of the village and, thus CERTAIN death.

Getting comfortable with people saying no, or even the threat that they may say no, is a chance not only to overcome many preconceptions in sales but also could be your golden ticket to hitting quota faster and more easily.

And while that may feel pie in the sky, the thing to tell yourself, your team, your entire sales department is (and this is 100% true)…

Every NO brings you closer to YES.
“No” is GOOD

Hot take alert, but someone saying “NO” and giving you a reason means you, or whoever is selling, is doing their job properly. The only thing is the job hasn’t been finished yet. More digging is required.

The Art and Science of Persistent Prospecting

When discussing sales and the impact of a persistent approach, it’s vital to understand what we mean by persistent prospecting. It’s not just a matter of dialing the same number or sending the same email over and over until you get a response. Instead, it’s an art and science that involves understanding the psychology behind sales, maintaining respect for the prospect’s boundaries, and leveraging technology effectively to enhance your sales efforts.

Persistent prospecting and follow-up is the dedicated pursuit of a potential client until they respond positively, indicating a willingness to engage. But it’s more than simply bombarding a prospect with calls or messages. It involves reaching out with relevant, valuable, and personalized content that resonates with the prospect’s needs and pain points, establishing trust and building relationships.

It’s the understanding that every ‘No’ brings you closer to a ‘Yes,’ a mantra that should echo in the minds of every salesperson. This perspective is grounded in the psychology of sales, which emphasizes the importance of resilience and persistence. The key is to view ‘No’ not as a rejection but as an invitation for further engagement and an opportunity to refine your sales approach.

Also, before we get deep into prospecting and calling, we need to really make sure that we have done our homework. How would you feel if you kept getting calls from someone trying to sell you a snowplough but you lived in the Middle East. You would probably think “Wow, this person is totally wasting their time!”

Doing a bit of research on your prospect before you start reaching out to them is a really important step. By understanding your prospect’s industry, company, role, and even their professional interests, you can truly tailor your approach to their needs and pain points. Use tools like LinkedIn and other social media platforms to learn about your prospect’s career and what topics they’re engaged with. Find out what news and content their company is pushing out to the wider media. Learn as much as you can without getting creepy. Liking an Instagram post of a burger they had three years ago is a bit of a red flag!

Professionally though, even the smallest detail, when used appropriately, can strengthen your connection. This could be anything from a shared interest, a common acquaintance, a past project they worked on, or a recent achievement they had. The more personalized your outreach, the better chance you have at capturing their attention and building rapport. And also, spending time engaging with them in places such as LinkedIn and social media, even if it’s the odd “like” or comment helps to build familiarity. Top tip? It’s a fantastic way to spot them voicing a need or requirement you may be able to solve. 

Another critical element of successful persistent prospecting is respecting a prospect’s boundaries. This means understanding the fine line between persistence and intrusion. Repeatedly reaching out at inappropriate times, or with irrelevant information, can risk alienating the prospect. It’s essential to strike a delicate balance, using intelligent engagement strategies that respect the prospect’s time and space. This might involve sending an informative article related to their industry, or a case study demonstrating how your product or service has helped a similar business.

Also, in the digital age, technology plays a pivotal role in persistent prospecting. A range of tools are available to automate and streamline the prospecting process, saving time and increasing efficiency. For example, Customer Relationship Management (CRM) systems can track all interactions with a prospect, reminding the salesperson when to follow up and providing insights into the prospect’s behavior and preferences.

Robin Williams in Jumanji asking what time zone is this

Asynchronous communication tools offer another powerful resource for salespeople. Unlike traditional communication methods that require both parties to be present at the same time, asynchronous communication—such as email or messaging apps—allows for communication at any time, providing convenience for both the salesperson and the prospect.

Video call recording tools provide valuable data for review and analysis. By listening to calls, salespeople can understand where a conversation went wrong or right, learn from their mistakes, and continually refine their approach. Call recording tools also provide opportunities for sales coaching, allowing more experienced team members to give constructive feedback and advice.

Using Async Communication in Prospecting

Being Async is an exchange of information that doesn’t require all parties to be present simultaneously. This means that we can be persistent without actually taking up “core time” from our prospects, thus being LESS ANNOYING!

In sales, asynchronous channels such as emails, recorded video calls, and collaborative platforms offer flexibility that respects the prospect’s time and caters to differing schedules and time zones.

A salesperson can share necessary information, presentations, or proposals at their convenience, and the prospect can absorb and respond to this information when it suits them. This approach removes the pressure of immediate responses, providing prospects with time to thoroughly consider the information and respond thoughtfully.

One awesome application of asynchronous communication is the use of recorded video calls. This method combines the dynamism and personal touch of a live conversation with the flexibility of asynchronous communication.

Recorded video calls featuring tailored product or service presentations can effectively articulate your unique selling proposition, address anticipated objections, and highlight how your offering delivers superior ROI. Prospects can watch the video at their convenience, pause, rewind, and re-watch as necessary, ensuring they fully grasp the information provided. The recorded call also serves as a tangible resource that can be shared with other decision-makers within the prospect’s organization, reaching a wider audience and increasing the chance of a successful sale.

Async comms is especially useful in reducing the logistical challenges of needing all decision-makers on one call. Given that B2B sales often involve multiple stakeholders, aligning everyone’s schedule can be a daunting task. With recorded video calls, the sales pitch can be shared and viewed by all relevant parties at their convenience, ensuring everyone is on the same page and streamlining the decision-making process.

Global remote working trends have further bolstered the use of asynchronous communication in sales. With teams spread across different time zones and working flexible hours, synchronous communication is often not viable. Asynchronous methods cater perfectly to this shift, offering an efficient way to connect and communicate.

Finally, asynchronous communication allows for more strategic follow-ups. By reviewing recorded calls, salespeople can note points where prospects had questions or objections, and craft personalized follow-ups to address those specific points. It ensures each communication provides value and nudges the prospect closer to a ‘Yes.’

Solid Strategies for Persistent Prospecting

Alright, let’s dive in. If you’re a sales manager, sales director, or senior leader, this one’s for you. Let’s talk about selling persistent prospecting to your team. Not in the cold, impersonal, textbook style, but more like a chat over coffee. It’s time to discuss strategies that can help turn those elusive ‘Nos’ into satisfying ‘Yeses’.

First off, let’s talk about understanding your prospects. Your team must personalize their approach every single time. They shouldn’t think of prospects as sales targets but as individuals with unique needs and challenges. When your team can tailor their pitches to solve their problems, that’s when you really start to see results. In an industry where terms like “numbers game” are thrown about and volume has always been praised over quality, it can seem like time wasted (particularly to the old school). However, time spent honing and building relationships that mean something and very rarely wasted efforts.

Timing and frequency of follow-ups is another critical element. The aim is to find that sweet spot—persistent enough to keep you top-of-mind, but not so frequent that you become a nuisance. A thoughtful email here, a quick call there, a snippet of your last video call, an informative article in between—it’s all about providing consistent value. While we want to encourage teams to be following up be mindful that they are speaking to the prospect and if they push back it’ll typically be for a good reason. Go over the communications and learn which members of the team have a good judgement and those who need a little extra encouragement to call back.

Now, let’s talk about recorded video calls. They’re a game-changer. Sales cannot only have personal, interactive conversations, but recordings also provide a resource that can be revisited, shared with their team, and dissected at leisure. And the best part? Everyone—whether they’re decision-makers or team members—gets the same clear message directly from you.

And here’s where it gets even better with tl;dv, a tool designed to ensure you never miss a sales opportunity. When you share a recorded call with a prospect and their team, tl;dv will notify you as soon as someone views it. That’s not just a notification—it’s a sales signal. It’s an alert that someone is engaging with your pitch, creating a perfect opening for a follow-up.

But what if the response isn’t what you or your salesperson hoped for? That brings us to feedback. Each ‘No’ is a goldmine of feedback. Use it to refine your approach, hone your pitch, and make your offer even more irresistible next time.

Knowing When to Move On: Navigating the 'Hard No'

While persistence is crucial in sales, it’s equally essential to understand when a ‘No’ signifies a clear end to the prospecting process. Not all prospects will transform into customers, and recognizing a firm ‘No’ can save time and resources, allowing you to focus on other promising leads.

Understanding when to move on requires discernment, emotional intelligence, and a keen understanding of your prospect’s reactions. Here are a few signs that it’s time to respectfully step away:

Anger or Frustration: If a prospect becomes agitated, angry, or explicitly asks you to stop contacting them, it’s essential to respect their request. In these cases, persistence can be perceived as harassment and may damage your brand’s reputation.

Lack of Fit: A prospect may not be the right fit for your product or service. Perhaps their needs don’t align with what you’re offering, or their budget doesn’t meet your pricing. If the gap is too significant to bridge, it might be best to move on.

Lack of Decision-Making Power: If the person you’ve been talking to doesn’t have the authority to make a purchasing decision, and they’re unable to or reluctant connect you with someone who does, you may be hitting a dead end. When doing your initial research and calls, it’s important to ascertain who the decision-makers are. So many sales reps end up in a long process of selling to someone without the authority, budget, or sway to make that call.

Persistent Disinterest: While initial disinterest isn’t a definitive ‘No’, if a prospect consistently displays apathy or disinterest, despite your best efforts to engage them with tailored content and solutions, it may be a signal to step away.

In sales, it’s critical to understand that ‘No’ is not always the enemy. Sometimes, it’s a guide that helps you navigate towards prospects who are more likely to convert into valuable customers. However, learning to identify and accept a ‘hard No’ is just as important as the drive to turn other ‘No’s into a ‘Yes’.

Keep On Coming Back To Them

Phew, that was a lot to take in, but every word worth it if it helps you elevate your sales game. To sum up, persistent prospecting—the art of intelligent follow-ups, the relentless pursuit of ‘Yes’—is a key to sales success. It’s not about sheer determination alone but about leveraging smart strategies and innovative tools to provide consistent value.

Async communication and video call recordings are your strategic allies in this pursuit. They offer the flexibility to engage with prospects effectively and the power to learn, improve, and accelerate deal closures. The modern sales landscape is teeming with opportunities if you know how to seize them. Tools like tl;dv can take your sales process from good to great, keeping you alert to the perfect moments for a follow-up.

So, to all you sales leaders out there, it’s time to roll up your sleeves and embrace these strategies. Equip your teams with the right tools, cultivate a culture of persistence, and watch your prospecting efforts pay off. Remember, every ‘No’ is just a stepping stone on the path to ‘Yes’. So, persist, innovate, and prosper!

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