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There are many challenges associated with selling and prospecting is no exception. Receiving countless 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.

That’s probably why a large number of sales people say that prospecting is their least favourite 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 success, there’s no guarantee they’re willing to buy.

So which type of leads are the easiest to book appointments which and which are the hardest?

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. 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, try upselling your clients while recapping your work. You’re already talking to them and any opportunities can be discussed right then and there.

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.

Not only do referrals convert at a higher rate, but the initial contact is done for you by your customers giving the referrals. If you aren’t using 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. 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 prioritise over considering new offerings. They might be managing their teams, dealing with suppliers, determining budgets, or taking on other 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.

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 approach.

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 conferring with other senior execs.

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 still, 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 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 take longer.

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

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

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 huge 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. And that’s because:

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 sales material from other companies, so it can be hard to stand out.
Their days are packed, 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 or CEOs, understand you’re in it for the long haul. Expect to need 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.

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.

If you’d like to learn more about the techniques you can use to approach new prospects, then get in touch.

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