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Optimizing Your Time for Less Painful Prospecting Activities

strategic sales prospecting training


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Prospecting is one of those activities that you either love or hate. For most people in sales, it’s unavoidable.

Those who hate it generally suffer from “prospecting procrastination,” which is when a person will seek out any kind of busy work in an effort to put off and avoid the dreaded task.

Perhaps it is loathed because it rarely (if ever) yields immediate gratification. Others can’t handle the hang-ups and rejection. Whatever the reason, sales reps must realize the importance of prospecting to building and sustaining a pipeline that will pay off down the road — depending on your sales cycle length.

Whether you’re gung-ho or reluctant, when you dedicate time to prospecting, you want to choose prospecting activities that will give you the greatest payoff. The best way to start is to view the world from your prospect’s perspective. Put yourself in their shoes to see just how likely you would be to respond to your own inquiry.

Making Quota: What’s Your Number?

There are few if any sales reps that don’t have some target to achieve. If you’re going to make your quota, then you need to critically and objectively examine your pipeline from start to finish to determine how many prospecting calls eventually lead to sales. Consider these broad steps:

  • w number of calls
  • generates x number of leads
  • which leads to y number of opportunities
  • and z number of sales
Of course, some have the benefit of marketing teams to help generate leads and opportunities. Whether you’re dialing yourself or receiving leads, you need to know how much pipeline you need to generate yourself in order to hit your number.

Get Your Timing Right

The next factor to consider is timing. You could have the best pitch for the best product at a perfect price. If your timing is off, your prospect might not only turn a deaf ear, but you could turn them off completely. When is your prospect most likely to respond to you?

Getting the timing of your calls right by better aligning your prospecting activities with your target's likelihood to take your calls will help improve your efficiency and productivity.

The nuances of timing can be examined by the hour of the day, the day of the month, or the month of the year. As an example, imagine your prospect is a CFO. Most CFOs have intense time pressures to close the books at the end of each month, quarter, and fiscal year. They also have tax season to contend with (which is pretty predictable), as well as audits. During these times, they probably won’t be very responsive to you — they’re just too busy.

However, they do have planning and budgeting seasons when they are more likely to be thinking about the investments they need to make and plan for the following year. You want to be planting the seeds leading up to those periods so that you have sufficient time to make your pitch, hopefully sell your product or service, and have it purchased and in place — ready to use when their cycle calls for it.

The bottom line is to realize that this is about them, not you, so choose your time wisely, and balance your message to fit their business cycle.

Modes of Prospecting

Once you have your timing down, you next must think about how your prospects prefer to communicate. There is no shortage of ways to reach someone these days, which makes it more challenging than ever since each person is different. Here are common ways to consider connecting with your prospects:

  • E-mail/Desktop — A more formal approach that lends itself to long and detailed messages; many people want a paper trail and thus everything in writing.
  • E-mail/Mobile — If your prospects are always on the go, they likely skim their e-mails on their phone, which isn’t a great medium for lengthy messages. Your e-mail might be scanned quickly, in which case, the prospect could overlook a key point. It is also likely to generate quick, terse responses.
  • Phone — If you’re a charmer, then this is the best way to get your charm across. Once on the line, you have less than 90 seconds to make your mark, so be prepared.
  • Administrative Assistant — Some prospects require that you pass through these staunch gatekeepers, which can again be a target of your charm. (But remember, this isn’t Mad Men!) Will you sound like someone their boss wants to do business with or just another cold caller to ignore?
  • Voice Mail — Some prospects never answer their phone, so practice the art of leaving a poignant, not rambling, voice mail, and promise to follow up by email if possible. Make it as easy as possible for them.
  • LinkedIn — If you’re active in LinkedIn groups and discussions, connecting with a prospect that way or through common connections can be fruitful; it’s always best to have an introduction whenever possible.
  • Social Media — This can be tricky, but it isn’t unheard of. Like LinkedIn above, having someone else help broker the connection is better than reaching out cold, which is likely to be ignored (or viewed as creepy).
  • Live Events — Pressing the flesh is still a great way to stay connected and look for prospects. There are plenty of networking opportunities, happy hours, conferences, alumni gatherings, and other events at which to meet people to find out first-hand what’s on their minds.
You could try some or all of these tactics. What’s most important is that you once again walk in your prospect’s shoes (like the CFO we talked about earlier). How do they prefer to communicate? Is there a combination approach that you should try, such as an e-mail followed by a phone call (or vice versa)?

The big takeaway is that you need to align your time and prospecting activities with your prospect’s behavior. This often takes trial and error to refine and optimize. I encourage you to initiate a process, test and track your results, and then revise your process based on what you’ve learned.

Prospecting Skills and Personalization

With prospecting, time and brevity rule. You need to communicate a crisp, clearly spoken value proposition in less than 90 seconds. Similarly, any prospecting e-mail that you write needs to be easily understood and answered with a simple “yes” or “no.”

Many sales reps fail to personalize the value proposition for each prospect, but it’s a critical step that can either get the conversation you seek or send you scurrying back to your prospect list. This is especially true for e-mail. We’re all so inundated with e-mail that I call it “Death by content marketing.” I can see right through a bulk message – I have no interest in it whatsoever.

The same can be said of cold callers who are clearly in over their heads and haven’t spent even three minutes researching me or my company. It doesn’t take much to engage them for a moment just to point out how hopelessly unprepared they are.

Your value proposition must demonstrate clear and compelling value for me to meet with you. As with most things in life that are worthwhile, building these skills requires you to test, practice, and revise in order to perfect them.

Sales prospecting skills are vital to the successful execution of the larger sales process. There are lazy spray-and-pray approaches that can make you look busy, but the best outcomes are most often the result of careful preparation and execution on the part of the sales rep — even ones who start the prospecting process reluctantly.

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