The Main Challenges of Appointment Setting (and How to Overcome Them)


Appointment setting calendar on a desk

Reaching out to prospective customers to set appointments can be a rather arduous task for some businesses. Depending on which industry you operate in and the markets that you target, the challenges that you face when attempting to organise sales appointments will differ from other companies, however, there are challenges that all companies have in common when appointment setting.

This article delves into these challenges, the impact that they can have, and how you can plan your strategy to overcome these appointment setting challenges.


Call Timing


High-level decision-makers are busy people, and they often don’t have the time (or patience) to take every marketing or sales call that comes through.


Depending on which day of the week that you are calling on, and the time of day that you are calling, you could see a big difference in how decision-makers you are reaching and have a full conversations with.



The time being displayed on a clock and calendar

According to a study conducted by CallHippo in 2017, Wednesdays and Thursdays are the best times of the week to call a prospect, and Friday is the worst day of the week to call prospects.


The results of this study aren’t particularly surprising and can be explained quite simply.


On Mondays, especially in the morning, decision-makers are getting back into work mode, and are likely planning out their week and replying to emails that have come in over the weekend.


Halfway through the week, on Wednesdays and Thursdays, the prospect has likely cleared some of their heavy workload and your call won’t be as much of an interruption to their day.


Of course on Fridays, particularly in the afternoon, businesses are winding down for the week and decision-makers won’t be wanting to get stuck on a call with a telemarketer.


If you are dedicating a couple of days a week to your appointment setting strategy, make sure you are going for the days that will give you the best contact rate to maximise your appointment opportunities.


Getting Past the Gatekeeper


Gatekeepers are a hurdle that every salesperson or telemarketer has to overcome daily, and some are easier to get past than others.


It’s important to make a good first impression when talking to a decision-maker, and this goes the same for the gatekeeper too. If you get through to a gatekeeper and come across as pushy or rude, it could result in a swift end to the call and make reaching the decision-maker on further calls more difficult.



Telemarketer placing phone down while at desk

It’s important to remember that if a gatekeeper is asking you questions about who you are, what company you are calling from, and the reason for your call, they are simply doing their job, so being impolite or rude isn’t the answer and could damage your professional reputation.


The best way to approach a gatekeeper is from a position of authority. This doesn’t mean being rude or aggressive, but it does mean being assertive, quick to the point, and giving as little information as possible.

See the example below of what to do and what not do when first reaching a gatekeeper. In the first conversation, the gatekeeper seems to have the authority, whereas, in the second conversation, the caller is assertive from the start.


Impressing the Decision-Maker


Getting through to the decision-maker is one thing, but impressing the decision-maker and generating genuine interest is another.

Decision-makers will receive dozens of sales calls each week, some of which could be from some of your competitors, so just delivering the same ‘salesy’ pitch as everyone else will get you nowhere.


Decision maker in written in chalk with a clock

When trying to impress a decision-maker, one of the biggest mistakes that some telemarketers make is talking too much about themselves and their company.


Sure, your personal and business achievements may be interesting, and mentioning experience in their industry is relevant, however, the decision-maker would be far more impressed with the way you interact with them, provide value to them, and actively listen and respond to their queries and concerns.


Doing your research into your prospects is also a great way to impress the decision-maker. Most telemarketers will pitch their offering and talk about how well it works for other companies and the results that they have seen. The decision-maker doesn’t want to know how it works for OTHER companies; they want to know how it will work for THEIR company.


Researching beforehand, you can tailor your pitch to talk about how your offering will benefit that prospect specifically, after considering their business type, the industries they operate in, the products and services that they offer, and the current climate of their industry/market.

All of this is going to be far more impressive to a high-level decision-maker, and help you to secure more quality appointments than a pushy, irrelevant, ‘me, me, me’ sort of pitch.


Missed or Cancelled Appointments


Once you have secured an appointment, the challenge is still not over; you now need to ensure that the appointment goes ahead without any delays or cancellations.

So how do you reduce the chance that a prospect will cancel the appointment that you have worked so hard to organise?


Timing When Booking Appointments


One of the biggest factors that can impact appointment cancellation rates, is timing.


When setting appointments, you need to be wary of how far in advance you are setting your appointments. If you set an appointment for four weeks’ time, for example, your chances of the prospect cancelling this appointment increase drastically. This can vary depending on the industry and level of interest generated with the prospect, but this is generally the trend that we see on almost every campaign that we run.


Setting appointments as soon as possible, ideally within a few days or up to a week from the call, you can see a huge reduction in appointment cancellations and start to get the ball rolling with clients as soon as possible.


Telemarketer holding up appointment setting calendar.

Appointment Reminders


Another way that you can reduce the chance of appointment cancellations, is by sending meeting reminders. After you have successfully booked an appointment with a qualified prospect, the first thing you should do is send across a calendar invite. This ensures that the prospect knows exactly when the meeting is taking place and reminds them every time they open their calendar.


In some cases, this can be enough to prevent appointment cancellations, but if your appointment is set for one or two weeks’ time, then it’s important to send a reminder email to the prospect 24 hours before the appointment.


This is just a friendly reminder email that says ‘Hi [Prospect Name], I’m just emailing to confirm that we are still on for our meeting tomorrow. I’m looking forward to meeting you and your team. Kind regards …’.


Be careful when wording your reminder emails, as you could be giving the prospect a perfect opportunity to cancel. For example, writing ‘Hi [Prospect Name], I’m just emailing to make sure you are still available for our meeting tomorrow. If you need to reschedule, please let me know. Kind regards …’ may seem like you are being considerate and polite, but in reality, you are shooting yourself in the foot by handing the prospect an excuse to cancel or reschedule your meeting.


In the New Year, we’ll be going in-depth with a full article on this topic, to help you minimise your appointment cancellation rate.


Lead & Data Management


A big challenge that a lot of new businesses face, is managing their sales leads and their campaign data.

With an appointment setting campaign, managing your appointment leads and prospects and correctly maintaining your database is vital of an efficient and effective campaign. Without a well-structured CRM system, you will likely struggle to achieve proper management of your leads which could result in lost opportunities.


Your CRM (Customer Relationship Management) system is where you will manage and keep track of all of your interactions with your prospects. Using your CRM system to its full potential (writing in-depth call notes for each interaction, correctly marking hot and warm callbacks, NFAs (No Further Action) and GDPR removals) helps you to prioritise who you should be contacting, keep track and remind yourself of previous interactions, and correctly manage record removals, maintain data compliance.


CRM system connecting multiple contacts together, keeping track of leads

When prospect interactions/relationships are not properly managed, this is when the real mistakes begin. This is when you start to lose track of what has already been discussed with different prospects, who the correct decision-maker is within different companies, whether other members of your team have already contacted a certain prospect, and most importantly, whether you are contacting someone who has previously exercised their data protection right to removal.

So to sum up, not correctly using your CRM system not only results in getting your wires crossed with other members of your team, impacting the success of your appointment setting campaign, but it could land you in hot water with data protection authorities if the issues also affect data compliance.


Final Thoughts


There are a lot of challenges that you will face when setting B2B sales appointments, some of which are just part of appointment setting and must be overcome, others that you can create for yourself and that require proper planning and maintenance of your strategy to be avoided.


Putting in place a strategy that considers all of the above, you could start to see an increase in quality leads and appointments and a much higher conversion rate from your appointment setting campaigns.


Does your business need help generating fully-qualified sales leads or appointments?


If you would like to know more about our B2B Lead Generation and Appointment Setting services and how we can help your customer acquisition process back on track, then please get in touch on 01329 277558, or drop us an email to enquiries@inspiredb2bmarketing.co.uk