The Easiest and Hardest Prospects to Book Sales Appointments With

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Justin Franklin
Justin Franklin



There are many challenges that come with any part of a sales process — and prospecting is no exception. Weathering relentless rejections and spending hours pursuing a prospect just to find out they aren't actually a good fit for your product or service can be annoying at best and soul crushing at worst.

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The amount of time put into content creation, emailing, cold calling, and other lead generation activities can seem tedious. Especially when results created by these activities lean towards the lower end. 

That’s probably why 42% of sales professionals say prospecting is their least favorite part of their job. So when a potential customer responds to your efforts, all the pain and stress of the process can seem worthwhile. But even though finding a prospect who appears to be a good fit to your offering might feel like a slam dunk, there's no guarantee they're willing to buy.

Over my career spent as a lead generator, I have come across several different kinds of campaigns. Here is a breakdown of the easiest and hardest campaigns I have taken part in to book sales appointments with various clients. This information is compiled from my time at TRO Lead Generation and Cobalt Iron using email marketing, social media, digital ads, and other strategies to book sales appointments.

1. Current and past customers (the easiest).

As far as sales is concerned, no potential customer is easier to close than someone you have already sold to before. Ideally, you have already built trust and loyalty with this prospect. This means getting an appointment should be as easy as a quick call or email.

If your relationship is really strong, you might just be able to instantly upgrade them on the first call or email simply because they trust your expertise.

If you’re in the B2B services space like me and you do weekly check-ins, try upselling your clients while recapping your work. You’re already talking to them and any opportunities can be discussed right then and there. You can check out some other ways to upsell current customers by checking out this blog post.

2. Client referrals.

If current and past customers are the easiest to book appointments with, then their recommendations are easily the next best thing. This is why word of mouth is one of the most powerful and cost effective ways to generate new customers.

When it came to acquiring new clients at TRO, a larger percentage of referral clients would convert to customers than customers that never heard of us before. This trend is aligned with metrics that say referral customers convert at about 13%.

Not only do referrals convert at a higher rate, but a lot of the outreach is done for you by your customers giving the referrals. If you aren’t utilizing referrals or a referral program you are missing out on a great opportunity.

3. A direct end user with influence, but no decision-making authority.

Prospects who haven't interacted with your business are tougher to register with. These are targets that are typically worked by a sales or marketing person to bring into the sales pipeline.

Your product or service might be something a decision maker needs, but for some reason you can’t get in contact with them. Even though they might understand your offering, they aren’t the ones ultimately using it.

On top of this, they most likely have other activities they have to prioritize over considering new offerings. They might be managing their teams, interacting with vendors, determining budgets, or taking on other similar responsibilities. If you are encountering prospects like this, it might be easier to reach out to direct end users that have some influence on the decision-making process.

This is because your offering impacts them directly. Additionally, since they don’t have decision making authority, they are less likely to be preoccupied with tasks and responsibilities unrelated to your offering.

A real-life example of this was a software campaign I ran while at TRO. We had a client who offered property management software that automated maintenance alerts as well as the assignment and cancellation of job tickets.

Our first approach was to go after decision makers directly by targeting building and real estate company owners. However, lead trickle was slow. To fix this problem, we started to target end users directly by engaging with the property managers themselves. Instantly, our sales appointments increased for this client.

We achieved 5 times the average appointments we were getting within the first week. This helped create a steady lead flow for our customer, enticing the end users to bring the real decision makers on a follow-up call. At one point, we even had to turn off the campaign just for our client to catch up with the demand for appointments.

Examples of these prospects include property managers, assistant managers, business development managers, recruiters, and architects.

4. Small business owners with no middle management.

These are the last of the relatively easy prospects to get sales appointments with. Small business owners with few to no employees and no middle management are great customers to go after.

They might take a bit longer to get to because of all the hats they are wearing, but they are also more likely to tell you yes or no and not waste your time. This is because small business owners with no middle management don’t have to consult with others in their business to make a decision.

These business owners know the ins and outs of their businesses. They don’t have to drag out the sales process by bringing in others like a CFO or CIO for input. This means you can often get an appointment by repeatedly asking or having killer ad copy to book a demo or consultation.

At TRO, these were the primary people I would target. Using one simple email campaign, I could often book 2-3 appointments per email. The best part? I only had to send to about 200 prospects to get these appointments.

Examples of these types of clients include consultants, personal accountants, public speakers, business coaches, and mom and pop shop owners.

5. Small businesses that have multiple owners.

Small businesses with multiple owners face the same challenges as small businesses with one owner. However, you now have to take additional steps to repeat the sales pitch you already did for the first owner.

It can be rare to get both decision makers to agree to an appointment at the same time. One can take the time to go to the meeting while the other takes the time to run the business while the meeting is taking place.

Worse yet, the business owner that you do end up booking an appointment with will often say they will just relay the information onto the other owner, lowering your chance to convert and increase your sales cycle length.

For this type of business, make it clear that all decision makers need to come to the meeting at the same time to equally hear your pitch. This way you can have an equal chance to answer everyone’s questions and not risk something important being left out.

6. Small to medium sized businesses that have middle management.

Here is the thing about middle management — they often have experience with the problem you fix but aren’t actively dealing with it on the same level as lower employees. They also don’t have decision making authority, but they can still be influencers to ones that do. This poses two possible problems.

The first problem is that if you go after decision makers directly, they will pass you off to middle management as a way to get rid of you. This means that, because they most likely don’t directly deal with the problem you solve, you have to try that much harder to convince them to see why what you're offering matters enough for them to take the appointment.

The second problem arises when you try to go directly to the person that feels the pain of the problem you solve. Instead of just two levels of appointments — the end user and decision maker — you now most likely have to convince at least three levels of involvement to listen to you, the end user, middle management, and finally the decision maker.

This means you’re adding an additional layer to your sales cycle. This makes the close take longer with a chance you might not get to even book the needed appointments to close. Expect sales processes like these to be on the longer end of the spectrum.

7. Medium to large sized businesses that have director level decision makers.

As you grow in company sizes, you can get more specialized with your departments. For a salesperson, you would think this would make things easier. After all, if departments are specialized, that means you just have to find the title of the director that handles the problem that you solve, right?

The problem is, job titles are often vague, and multiple directors and VPs can have the same job title. This means not only do you have the problems associated with middle management, but your prospecting process takes longer simply to find the appropriate contact or department.

This means, if you don’t have appropriate targeting, you can spend a good amount of time chasing the wrong prospects, which wastes everyone’s time and gets expensive.

8. C-Level executives of enterprise level companies (the hardest).

We have come to the hardest of the hard to book sales appointments with. C-level executives of enterprise companies have a lot on their plates. Connecting with them offers all the difficulty that the previous examples listed:

  • They most likely aren’t actively involved with the problem you solve.
  • They have to bring in multiple perspectives to determine how a solution will impact the business.
  • They are constantly receiving ad and sales material from several other companies for various solutions, so it can be hard to stand out.
  • Their days are packed with different activities, so their time is limited.

All of this amounts to the longest sales cycle of any prospect — with a good majority of the time spent just trying to get in front of them. And when you finally do, they can easily pass you off to one of their subordinates to start the process all over again

If your product or service requires you to go after executives like CIOs, CFOs, CEOs, or presidents of large organizations, understand you're in it for the long haul. Expect needing multiple touchpoints from both your sales and marketing team to be effective.

In my experience, it can take several months — sometimes even years — just to get in front of these decision makers to simply set up a first meeting. That's why when you do finally set up that meeting, be prepared with a tailored solution that fixes their specific problem.

For Cobalt Iron, our value proposition talked about how we made data backup easier to manage with automation while simultaneously cutting costs. Additionally, we would attach case studies that were relevant to the target company’s industry and have a brief pdf description of our offering.

We would then highlight three to five individual snippets from this material in the email response or landing page to make it easier to read.

How to Book Sales Appointments with Hard-to-Read Prospects

The key factor to reaching these prospects is persistence. Keep trying and experiment with your marketing and sales tactics to see what works best. Here are some tactics and mindsets I have used to get in front of these prospects.

1. Don’t be intimidated. 

Mindset is a key factor to success. When reaching out to C-level executives of enterprise companies, it can be easy to feel intimidated. After all, these prospects could have hundreds to thousands of people directly under them and can influence a company’s direction with one email.

You might be thinking: "Somebody with that level of authority won’t talk to me." You’re wrong. C-level executives are people with problems  — just like everyone else — and they are looking for ways to solve them. If you happen to have a solution to what they are looking for, they will talk to you.

This doesn’t mean they will buy from you, but they will at least listen. The reason these conversations aren’t happening though usually arises in the pitch to these prospects. A bad opener is what gets 99% of sales people ignored.

2. Talk about the problem you solve, not what your offering does.

When it comes to pitching to decision makers, we tend to think they already know everything. Salespeople think that if they just pitch the problem they have without listing details, that the executive is just going to ignore them. This is what salespeople think C-level execs are like:

“I already know what my problem is and how to solve it, tell me your features so I can see if it fits the solution I’ve already thought up.”

From my experiences let me tell you, very few if any executives think like this. They are constantly bombarded with different fires to put out every single day. Do you really think they want to take the time to dissect your offering right off the bat?

They don’t. Instead, pitch a simple solution while highlighting outcomes of what your solution has done. Additionally, you can use audience segmentation to talk about specific insights related to your prospect.

For example, at Cobalt Iron, we use a combination of cloud and automation to provide backup. However, if I was to simply state that to a prospect, chances are they are going to ask me “Okay, so what?”

Instead, I have seen success pitching how, using automation, we have helped cut backup times for companies by upwards of 90%. Now instead of providing just a feature, I’ve established a cause and effect, which will resonate better with prospects.

3. Use specific insights, but don’t overdo it.

Making yourself stand out from the crowd is critical. If you want to get through the barrage of noise that plagues C-level executives, it would be wise to tackle a specific piece of information related to that target.

Mention seeing them in the news in an email or LI Message. Target your ad copy for specific landing pages prospects looked at using a web pixel. Follow up with webinar signups addressing specific points in the presentation they deemed important.

What you don’t want to do is spend more time researching than doing. Perfection is the enemy of progress here. Why would you waste your time researching a prospect for hours at a time, only to find out they aren’t qualified when you engage with them?

Using email, I was able to book a meeting with the head of infrastructure at a Fortune 500  — just by talking about the problem I solve. Sure, I could have done a bunch of research on the company and talked about the specifics. The problem with that approach is that it's hard to scale, and most of the time, it can run the risk of turning into fluff.

Get to the point as quickly as possible to make sure they get what you’re offering as soon as they can. Otherwise you risk losing their interest. So, try and narrow the company insight down to less than 15% of your copy.

For instance, If I saw that a CIO was on a TV interview, I wouldn’t mention the interview and then talk for 2 paragraphs about the specifics of the interview. Instead I would pick one topic point and address it, then go into my pitch.

Each business is different and has unique approaches. Company size, product offering, location, and price can all impact the likelihood of closing prospects. If you take the time to know the kind of prospects you should be going after ahead of time, you can save yourself future headaches and wasted time.

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