How to Master the Art of Cold Calling

July 14, 2020

“We’re not interested.”

“How did you get this number?”

“Take me off your list.”

These are just a few of the phrases thick-skinned sales reps are used to hearing when cold-calling. For them, these types of reactions are positive: receiving a hard “no” means reps can focus on other prospects. Every “no” is one step closer to a “yes.”

Done successfully, cold-calling can result in new business, lasting professional relationships and recurring revenue. However, it takes more nuance than dialing.

“You can make 200 calls a day but if you don’t have a strategy, then you are setting yourself up for failure,” Shannon Heidloff, a senior strategist at DoorDash, said. 

Expect plenty of rejection. A recent study from Topo said it takes an average of 18 calls to reach a buyer. Heidloff said ample research and preparation are essential to each call, and urged fellow sellers not to fall into the trap of a blanket pitch. 

Buyers don’t like “being sold to,” Heidloff stressed. Conversation and personalization go a long way. Researching the caller, identifying their needs and inserting your product are the first steps to closing a deal. 


Shannon Heidloff
Sr. Strategic Merchant Lead-Midwest

Know Your Industry. 

Know who you are calling and research the industry. Take time during non-selling hours to study trade publications, recent legislation that impacts their industry or community and trends. Google “buzzwords” or industry lingo that you can pepper into the conversation to build credibility. Skim the news to see if anything major is going on that could impact the call. Stay informed and knowledgeable. This might sound time-consuming but it will build instant credibility and lead to a more efficient sales cycle in the long run. 

Have a strategy for your day, down to the hour. Do research, get organized and find a place in your home or office that lends itself to a productive and efficient work environment. Then start dialing.


Identify Key Decision-Makers.

The first thing is to know who you are calling and if the time of day makes sense based on their industry. Business owners and operators have to actually run their business during the time you are calling and these cold calls, as opposed to scheduled meetings, can be a nuisance. For example, if you are calling on restaurants, avoid calling up to 30 minutes before a shift starts, which would be their lunch and dinner hours. This “pre-shift” time can be stressful and the last thing someone wants when they answer the phone is to hear an overeager rep. Set call blocks for 60-90 minutes in the morning and in the afternoon when you know there is a bit of downtime and you will most likely get a better reception. 

Spend 10 minutes studying their online footprint to figure out where to call and who to ask for. If this isn’t obvious from their website, social media or a quick Google search, write down a few questions to ask before you call. 

Make sure you know the goal of the call and the key decision-makers, as a one-call close is rare. Let whoever you are talking to know that their time is valuable and you appreciate it. 


Know When to Move On.

Know when to move on. Have a short list of questions prepared in advance that you can quickly reference based on a number of scenarios that you might encounter, but remember not to take anything personally. Any person who is cold-calling any type of business needs to know that there will be hundreds of calls they will make that end with some sort of a let down. It might take 15 calls at different times of day to find the actual decision-maker and then once you reach them, they might instantly dismiss you. 

However, persistence is crucial and so is a tough mindset. Move on from the hang-ups and agitated gatekeepers. Realize that you have no idea what they are dealing with in that moment or in their personal life. You are interrupting their day and their job and possibly taking them away from paying customers. If you sense that it is a bad time, end the call in a polite and professional manner. Ask a quick question about when would be a good time to try back or glean any sliver of information that you can. Reach out on a different day of the week or time of day. If you get the same gatekeeper every time you call and they shut you down every time, then reach out via social media, LinkedIn, etc. 

Always Be Prepared.

Once you’ve got someone on the phone, what strategies have you found to be most effective for keeping the conversation going and turning that person into a customer?

Be ready to pitch. We have all made a dial during a cold-calling block of time, not expecting to reach anyone and suddenly the decision-maker happens to be available and will give you five minutes. Be prepared! The worst thing you can do is to actually reach the person you’ve been looking for and stammer or stumble into a pitch. You need to make a good impression or you will lose credibility. 

First and foremost, ask them for their direct email and cell phone number, as having the correct information for the future is key. Have questions ready that will directly speak to their services and align with what it is that you are selling. It will show that you have done your research and will open up the conversation. The more they talk, the more you can learn about what their needs are and how you fit in. Gain agreement along the way and make sure to ask open-ended questions. 

Once you hit the allotted time-frame, ask for more time or a better time to continue the conversation. Thank them for their time and acknowledge how busy they must be. Earning trust early in the partnership will set everyone up for long-term success. If they are buying in, make sure to be enthusiastic but not over eager, and create a sense of urgency without sounding desperate. 


Establish Next Steps.

Ask them how they prefer to communicate going forward.

If you happen to end the call with a “yes,” then clearly define what comes next. Follow up within a few hours with detailed next steps and most importantly, a “thank you.” Guide them through the onboarding process and don’t falter with the follow-up communication. The initial stage of a partnership is still part of the sales process in many organizations, with the ultimate goal being their success. This can bring you referrals and a solid reputation in the long run.

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