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Qualifying your candidates quickly will result in more efficient conversations and ultimately lead to more closed sales. This series, “Asking the Right Prospecting Questions” is designed to help you ask the right questions to qualify prospects. We will take you through examples of technical, business, and personal questions.

As some of you will notice, this series is loosely based on the tried-and-true Sandler Methodology of Sales. These questions are only a jump-off point and are meant to be customized to your target audience and personal style.

Here are five questions that will provide you with the necessary information to help you identify the nature of your prospect’s problem and start to determine whether or not your solution is an appropriate fit.

1. What challenges are you trying to address?

Prospecting isn’t only about qualifying leads. It is also about finding out the challenges and needs of viable prospects. Once you have become intimately familiar with your prospect’s pain points, only then can you evaluate if they are a good fit or not.

Follow-up question: What impact does your challenge have on your business?

2. How have you been dealing with this issue up until now?

First, you want to know whether or not they have a current solution. By knowing if they are working with a competitor, it gives you greater depth to their challenge statement. Second, this question provides additional insight into their priorities.

Follow-up question: Have you made a similar buying decision before?

3. What are the risks or downfalls involved in not solving this issue?

One key to selling is removing or mitigating risks, both on your side and the prospect’s side. By identifying a prospect’s risks (or perceived notion risks), you can easily and quickly determine priorities and pain points. And knowing their priorities will help you know what to lead with during the sales process.

Follow-up question: What are the risks involved in solving this issue?

4. What other stakeholders are associated with this challenge?

Not only will you find out who else will be involved in the process, but this question should give you a good idea of what the process will look like, how many other people you will have to pitch, who your prospect will need to pitch, etc. By knowing all of this information upfront, you can save loads of time, plan more effectively, and make the selling process faster.

Follow-up question: What does your timeline look like?

5. What is your criteria for evaluating solutions?

This question will reveal the qualifying elements. As important as qualifying leads is, it is equally important to disqualify leads. If a prospect isn’t the right fit, you don’t want to find yourself chasing a white rabbit--wasting both your time and your prospect’s time.

Follow-up question: What alternatives are you considering, if any?

By asking deep and probing questions, you will not only have established a better relationship but will have hopefully learned all that you need to help your prospect with their problem. Be sure to stay tuned for our next post on “5 Business Prospecting Questions You Should Always Ask.”

We know that prospecting can be a lot of work--but it doesn’t have to be! Take the grunt work out of sales with prospecting automation. Prospecting automation, like CoPilot, removes the manual work from prospecting so that your cold leads are just a bit warmer when you first make contact.

It is the holy grail of the sales world: how do you find people who want your product? While there are the traditional methods of finding prospects such as in-person networking events, webinars, client referrals, and email lists, sometimes you have to get a little more creative. Here are five undervalued methods for mining for prospects.

1. Communities and Online Datasets

Clever sales reps use communities and online datasets for clues about the needs of their prospects. For example, one of our senior account executives, Joe Moore, uses sites like Crunchbase, AngelList, Glassdoor, and to look for early-stage and startup companies, or companies looking to hire sales reps. If a company is growing, they are prospecting more. By approaching discovery from the prospect’s perspective, Joe has been able to contact with the right people at the right time.

2. Live Chat

Live chat is a powerful way to capture unaware prospects. They can be people who don’t want to be pressured into talking to a salesperson yet, and are most likely just using chat for general questions. Whatever the reason is, they are interested in your company or product, which makes them a potential prospect. Live chat can either be passive or assertive. Proactive live chat allows you to track a visitor’s progression through a website and automates a chat window when they have gone through a predetermined journey. By completing a predetermined customer journey, they have almost qualified themselves--leaving what else there is to qualify a little easier.

3. Slideshare

Did you know that Slideshare is one of the top 120 websites in the world? By attracting 60 million unique visitors a month, it should come as no surprise that Slideshare is a fantastic lead generator. What makes this community stand out as a sales generator are the features available in the PRO version. The PRO version offers presentations to be gated, so viewers are required to provide contact information to access it. Provided that your content is in line with your qualification factors, this is passive yet powerful method to prospect.

4. LinkedIn Groups

Most sales reps are using LinkedIn to do some type of prospecting, but not all are utilizing the full power of the social network. While you are probably using LinkedIn to capture information about your prospects, utilizing LinkedIn Groups is extremely powerful in generating strong leads. Contributing to these groups is sure to bolster your reputation and relationships.

5. is the world’s largest online network that helps people with shared interests to plan meetings and clubs around the world. While it can be argued that Meetup is the same as in-person networking, it is so much more. By providing you with preceding knowledge through online profiles and RSVP lists, you can see who is attending an event. While Meetup is certainly an upgrade to traditional in-person networking, there is definitely a right and wrong way to attend Meetup group events. The wrong way is to be pushy, self-serving, and only driven by business card accrual. The right way is to be helpful and act as a resource. By opening up a two-way street, you will have established another fruitful prospecting channel.

These are just a few methods we use to find people who we can help. What are some creative ideas you have tried to find or engage with prospects?

For salespeople, CRM and prospecting go together like summertime and fog - it’s hard to imagine one without the other (at least, if you live in San Francisco). But for the modern sales development rep, CRM isn’t enough anymore. You need automation, too.

If you’re not quite clear on the difference between CRM and prospecting automation, you’re not alone! Read on to learn why it’s so important.

CRM Wasn’t Meant for Large-Scale Prospecting

There’s a good reason salespeople rely heavily on CRM. It’s a powerful tool to manage customer information, report on pipeline, and forecast revenue. It’s even OK for sending occasional one-off emails. But therein lies the problem: in a hypercompetitive business landscape, a “one-and-done” email blast out of Salesforce is a sure-fire recipe for spam filters and low response rates. CRM just wasn’t built to run the targeted, large-scale, multi-touch prospecting campaigns that are essential to success today.

stressed-and-overworked_sepia_sm.jpgTo compensate for CRM’s shortfalls, salespeople have traditionally turned to task-driven applications to help them keep track hundreds and often thousands of contacts, touches, and email templates, all at different stages in the prospecting funnel. The result, as Autopilot CEO Michael Sharkey stated in a recent 

VentureBeat interview, is that salespeople have “become so busy being taskmasters they hardly focus on creating opportunities, qualifying and having conversations with engaged prospects.”

More Time on Selling, Less Time on Tasks

Luckily, there’s a simple solution to the task management time drain: automate the tasks. That’s where prospecting automation comes in. Sales automation applications like CoPilot can automate many of the biggest CRM time wasters, freeing up your time to focus on activities that actually drive results.

Here are just a few of the CRM-related tasks you can automate with CoPilot:

  • Follow-up Emails. If your idea of sales automation is sending one-and-done mass emails from Salesforce, consider this: CoPilot lets you create multi-touch email drip campaigns that go out automatically at a cadence set by you. Automate second, third, and even fourth follow-up emails based on the prospects’ behavior. You’ll receive alerts when a prospect responds, so you can spend your time following up with only the most engaged prospects.

  • Logging Activities. CoPilot automatically logs your activities in Salesforce, so you don’t have to. No more follow-up tasks. No more email reminders. No more wondering whether someone clicked your link or opened your email.

  • High-volume Prospecting Campaigns. CoPilot makes it easy to scale your prospecting campaigns way beyond the daily limits set in Salesforce. You can add thousands of prospects to a single campaign, and it’s easy to manage multiple campaigns at once. CoPilot also comes with a pre-warmed IP, so you don’t have to worry about hurting your personal sender reputation score.

Does the rise of prospecting automation mean that CRM is irrelevant? Far from it! You still need CRM systems like Salesforce for all the reasons we listed above, but we need to call a spade a spade: Salesforce is CRM. CoPilot is a true sales automation tool.

While CRM still matters, only prospecting automation will help you spend less time on tasks and more time doing what you do best: selling.

Driving top-of-the-funnel growth is an obstacle a majority of companies face—but once they are in the funnel, then what? How do you treat leads once they have entered the funnel? What does the internal structure look like? Craig Rosenberg, author of Funnelholic Media and co-founder of TOPO, is an expert at turning ordinary companies into revenue-generating machines. Here is what he had to say:

One tip you offer salespeople looking for ways to avoid the “dark stage” (i.e. when we don’t hear any response from prospects), is to figure out the WIIFM factor while defining when prospects need to be called. What is WIIFM and how does identifying it help salespeople reduce the likelihood of entering the “dark stage” with prospects?

"WIIFM" is an acronym for “What's in it for me?” One of the biggest reasons prospects don't respond is because the salesperson does not offer any value. The perfect example is the "check-in" request when a seller tells the buyer they want to "check in." The "check-in" call is for YOU—that is, an opportunity for YOU to get an update on THEM. They don’t gain anything from coming out of the darkness and talking to you. If you are working on a deal, you first need to understand their buying process and then create a set of mutually agreed-upon next steps. The next meeting should be focused on something you both agreed to and has meaning to the buyer. That meeting should be set while you are still on the call with the prospect. If it's a longer buying process and there aren't clear next steps, approach the buyer with something meaningful to them. One organization I recently worked with leveraged a trends report to ask for a meeting. While most companies use research to generate leads, this particular company’s sales reps offered the report as an opportunity to talk about their findings. The offer is something that only benefits the buyer and allows the salesperson and organization to establish credibility as a trusted advisor.

You’ve noted that “young salespeople are building their career on the phone with inbound leads and don’t understand how to triangulate on a deal in an organization.” Help us understand what it means to triangulate on a deal and why it’s important.

Triangulating on a deal means you identify, reach out, and sell to multiple stakeholders in a particular deal—especially the decision maker. In the old days, we weren't even allowed to talk about deals in forecast meetings unless we talked to the decision maker. Granted, today’s internal influencers are much more powerful in deals. That being said, the influencer is going to have to internally sell to a committee. A good salesperson will know who the committee is, what their interests are, and then sell to the key players to win the deal.

You’ve said that in order to optimize qualified lead follow up, it’s important to pay attention to the way leads are transitioned from marketing to sales. What is the most effective and efficient way marketing teams should hand off leads to sales?

Well, first and foremost, we recommend a sales development function. Sales development is a phone-based team whose job it is to follow up, qualify, and set appointments for sales. Organizations need to agree on a qualified lead definition that states the demographic (company, role) and psychographic (business pains and drivers) requirements sales development needs to gather before passing a lead to sales. When sales development identifies that a lead is qualified,  then they pass it to sales. If you send raw leads directly to sales (closers), they won't put the necessary time and effort needed to reach out and your marketing programs will fail.

You believe that in today’s market “one of the most important factors in creating a scalable, repeatable revenue machine is sales and marketing alignment”. Walk us through why this is the case.

It's pretty simple. High-growth companies have a demand generation function that generates and nurtures leads. When these leads are deemed ready to talk to someone, they are passed to sales development who qualifies them and passes them to sales. Salespeople then close qualified opportunities. All of this is trackable and as a result, optimizable. If you don't build the machine, your competitors will.

What do you predict the biggest challenge will be for salespeople in 5 years and how can we start preparing for it now?

In five years, salespeople will continue to face the problems they face today—the ability to have the right to actually talk to people to later sell to them. Our only solution is to continue to make the role of sales one of incredible value to the buyer. Salespeople who act as credible, trusted advisors to their customers are the top performers today. Tomorrow, they will become the norm. The old "book ‘em and cook 'em" rep will go by the wayside.

About Craig Rosenberg

craig-rosenberg.jpgCraig Rosenberg is the Funnelholic and a co-founder of TOPO. He loves sales, marketing, and things that drive revenue. On his popular blog, Craig tackles topics of interest across sales and marketing including buyer personas, content marketing, demand gen, inside sales, lead qualification, marketing technology, and social selling. Follow him on Google+ or Twitter

It is not marketing automation, it is not CRM, it is the unserved gap in between the two. What closes the gap is prospecting automation.

Think of prospecting automation as the sales use case of marketing automation. We have taken the overly complex process of sales prospecting as it is today and simplified it into an intuitive and repeatable system.

It works a little like this: whenever a prospect engages with an outbound campaign, an automatic and personalized response is sent out based on that person’s actions. Those who respond with interest are then directed into the salesperson’s inbox while the rest continue to receive automated nurturing--allowing salespeople more time to do what they do best: SELL.

The right prospecting tool will also provide real-time data, seamless integration with CRM, and data provider tools.

By automating most of the prospecting steps, the first time a salesperson actually has a conversation with a potential client, it’ll be about closing a deal. Prospecting automation is a good fit for those who identify with any of the below situations:

  • You can’t accomplish what you need with your company’s current marketing automation tool or CRM.

  • You are spending hours a day manually following up with email and logging tasks and activities.

  • You use a variety of task driven applications to manage your day-to-day activities.

  • You have a hard time knowing when is the right time to reach out to prospects.

  • You would like to measure what type of messages are resonating with people i.e. A/B testing

Do any of these situations sound familiar? Give prospecting automation a try with this 7-day trial. Still not clear on what prospecting automation is? Sign up for a 20-minute overview for a closer look


“It’s the power of marketing automation, designed specifically for a sales rep.”

-Matt Childs, Vice President of Sales and Strategy, Vidcaster


With over 500 million users, getting past Gmail’s notorious spam filters is an obstacle most sales teams face. Gmail’s spam algorithms can be so effective at filtering that legitimate emails can sometimes find their way into the junk folder. Gmail isn’t the only one. Many traditional email clients experience the same issue, making them unreliable sales prospecting tools. Here are six other reasons why you should avoid Gmail when sales prospecting.

Lack of Reporting

Sales teams need insights into how their campaigns are performing so they can make informed and intelligent decisions about which campaigns are driving the best results. Traditional email clients just don’t provide the reporting tools that sales professionals need. We need at least these key metrics to track our success:

  • Delivery rate

  • Unique opens

  • Unique click

  • Unsubscribe rate

  • Bounce rate

Multi-Touch Automation is Absent

Traditional email clients are old school. Given that a majority of salespeople are sending hundreds of emails a day, manual follow-ups can seem like a daunting task. Gmail lacks the necessary ability to send personalized email drip campaigns.

No Prospect Tracking

Sales teams need real-time activity feeds so they can monitor exactly how their prospects interact with their campaigns. By monitoring a prospect’s behavior, it is possible to know exactly when they are interacting with your campaigns. This is incredibly useful when your prospect is engaged, and they just so happen to receive a call from you at the same time.

Missing Research Intelligence

As meticulous salespeople, we invest a lot of time into researching each prospect. Most traditional email clients lack the prospecting tools needed to obtain simple information like job title, company, industry, location, employee count, or even LinkedIn profiles. A simple prospecting automation tool will automatically pull this information and save you hours of time.

No Email Delivery Window

Every sales professional has a preference of when to send emails--whether it be early on a Wednesday morning or late on a Thursday afternoon. Custom delivery is crucial when prospecting for sales. Gmail and other traditional email clients don’t provide the custom delivery options you need.

Spam Indifferent

For having one of the most advanced spam filters, Gmail certainly doesn’t help their users out when it comes to sending emails. It would be immensely beneficial if there was a tool that can scan emails for common problems that lead to being dumped in the junk folder. Wait a minute--there is a tool that does just that. It is called Spam Checker.

Spam Checker is available through CoPilot, our prospecting automation tool built from the ground up. We are constantly working behind the scenes to ensure CoPilot’s emails have the best chance of landing in the prospect's inbox. Some other advantages include being assigned a pre-warmed IP address for a higher deliverability rate, having a built-in spam checker, handling unsubscribes seamlessly, and generally making sure ISPs love your content!

CoPilot is a sales professional’s best friend! It takes all of the manual work out of prospecting so you could generate more qualified leads and drive higher response rates. KISSmetrics increased their response rates from 6% to 32% with CoPilot!

Ready to start prospecting more efficiently? Get started now.

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