Episode #408: Lester Sydney

Lester Sydney firmly believes that you need a multi-threaded approach when it comes to prospecting. Cold-calling must be a part of your overall prospecting toolkit. So how do you prepare for cold-calling? How do you keep a cold call engaging and reach your objective of scheduling a follow-up? Lester shares his fun strategy in this episode of Sales Reinvented. 

How Lester prepares for cold-calling

Lester emphasizes that everything starts with mindset. You need to be in the right mindset before you have any conversation in the sales process. Lester will put on his favorite music to get amped up. Then he puts a big smile on his face. Why? Because it has a chemical reaction in the body. If you’re in a bad mood and you smile, it’ll instantly change how your body is feeling. He won’t start making phone calls until he’s done this. 

Lester’s unique opening technique

When you cold-call people, they tend to revert to defensiveness immediately, so you have to disarm them quickly. How does Lester do it? He playfully says, “Fair warning, this is a sales call. Are you sure you don’t want to hang up?” 9 out of 10 people start laughing.

Then he’ll say, “When I talk to people in your role, I find 2–3 reasons why someone like you might want to have a conversation with me. Are you open to spending a few minutes with me to see if they resonate with you?” 

But what happens if you immediately get “Not interested” when you make a cold call? Lester doesn’t accept that type of rejection. He’ll say, “What aren’t you interested in?” They’ll take a mental step back and often give him a few minutes to share why he reached out. 

How Lester keeps a cold call engaging

Lester believes that you need a playbook for cold calls. Just like in football, without the playbook, how are you going to be effective with anything you do in that game? Your script should outline your overall goals and the steps you need to accomplish. 

He keeps his calls at 3–5 minutes. He shares 2–3 pain points that he’s heard from his ICPs. He’ll share the challenges he thinks they’re facing, confirm whether or not they’re facing them, and then ask some follow-up questions. 

Lester’s top 3 cold-calling dos and don’ts

• Make sure you’re standing up. Why? You’ll project the right tone.
• Match the tonality of the person you’re cold-calling.
• Secure a follow-up meeting if there’s a level of interest.
• Don’t call someone and ask them “How are you doing?” You don’t know them, why would you care?
• Don’t jump in and vomit all over the prospect by telling them what you do. You need to find out if it’s of value to them first.
• Don’t do all of the talking. Ask questions, provide a pain probe, and get the prospect talking.

Lester sells database support and professional services. Oftentimes, when he cold-calls a VP of IT, he’ll share that database administrators often run into challenges and bottlenecks they can’t uncover. Then he’ll ask if it’s something they’ve experienced and how they’re managing it. 

What else helps Lester find success with cold calls? He shares more in this episode! 

Connect with Lester Sydney

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Learn More About Lester Sydney

What was a pivotal moment or experience in your career that shaped your approach to cold calling, and how did it change your perspective or strategy? A pivotal moment in my career that transformed my approach to cold calling occurred while I was at Black Duck Software. Our CRO brought in Steve Kraner as our sales coach, and his training completely shifted my perspective. Instead of immediately explaining what we do to prospects, I learned to first ask for permission to share three reasons why someone in their position might be interested in a conversation with me. This change was a game changer, moving my outreach focus from being centered on me and our company to addressing the insights and feedback we’ve received from others in similar roles.

Can you share a specific tactic or approach you’ve used in cold calling that significantly increased your success rate? Please provide a brief example or case study. In my humble opinion, disarming your prospect during a cold call is essential. One tactic I use is to be upfront and say, “This is a sales call—are you sure you don’t want to hang up?” It’s important to say this in a playful tone. Nine out of ten people will laugh because it’s rare for cold callers to be so candid, which often makes people uncomfortable. This approach, or similar ones, works well to disarm the prospect since their guard is usually up when a salesperson calls.

Cold calling often comes with its set of challenges and rejections. Can you share a particularly tough challenge you faced while cold calling and how you overcame it? There are numerous challenges individuals face with prospecting, but one that consistently arises is prospects saying they aren’t interested before you even explain why you’re calling. Personally, I don’t accept this initial dismissal. When a prospect says this, I respond with, “What in particular are you not interested in? I haven’t shared anything with you yet.” I then add, “I’ve been speaking with many individuals in your role, and they often mention facing this common challenge. I can’t imagine you haven’t experienced it too.” This approach has often helped me turn initial resistance into meaningful conversations, as prospects see that I understand their role and the common challenges they face.

What are the top three tools or resources (e.g., software, books, training programs) you consider essential for someone looking to improve their cold calling skills and outcomes? Top three things sales people should do to improve their cold calling skills are 1.) Practice role-playing cold calling daily 2.) Read Fanatical Prospecting by Jeb Blount 3.) Network with as many other sales people who cold call and learn from them.

How do you foresee the practice of cold calling evolving in the next few years with advancements in technology and changes in buyer behavior? What advice would you give to sales professionals to stay ahead of the curve? I know it might sound cliché, but I genuinely believe that AI technologies will significantly enhance every aspect of a sales professionals performance. In particular, there are numerous AI tools for cold calling that sales professionals can use to practice in the comfort of their own homes. Those who practice the most will see the greatest improvement in their skills. My belief in the future of AI in sales is so strong that I have joined RNMKRS as a Strategic GTM & Sales Advisor. RNMKRS is an app that sales professionals can use on their phones to improve their skills in conducting impactful and effective discovery calls. Buyer behavior has already changed drastically over the past decade, with many buyers conducting extensive research on products and software. It’s crucial for companies to enhance their marketing efforts and embrace product-led growth. I strongly recommend that all sales professionals embrace AI, learn how to leverage it, and become experts in its use.