How to Manage a Sales Team With or Without a Crisis (Part I)

Are you a small business owner struggling to manage the sales team…?

How to Manage a Sales Team With or Without a Crisis (Part I)

Wendy Weiss, The Queen of Cold Calling™

I have been wondering about the challenges small business owners face when they manage a sales team. I set out to interview some business owners to see what they had to say. Between the time I came up with this idea and actually executed it, COVID19 arrived on the scene. That made me curious to find out whether the challenges faced by business owners in managing a sales team has shifted due to the virus. They had so many interesting observations that I had to create two articles! This is Part I…

Brian Lambert
President and Chief Performance Officer
Growth Matters

Brian’s sales team consists of 2 salespeople. He described them both as hunters. Brian said that his #1 challenge in managing a sales team is, “Can they deliver the message and are they passionate about it?”

He went on to say, “Our hiring process is rigorous, so they have the skill, but what do they say? The space we’re in is very new to people. It’s also highly intangible. We are selling our know-how, smarts, methods, frameworks, consulting and services that are not necessarily productized. A lot of sales people struggle with that.”

Brian went on to say that his company tries to figure out how to help people work differently and to simplify business processes. That’s hard for sales people to articulate and there’s often a messaging gap, around the business case for working differently and/or the business case for simplifying. His sales people need to be able to connect the dots in the customer’s organization.

When I asked Brian if his #1 challenge had changed post-coronavirus he said, “Now we are getting meetings, but when we have those meetings, we are struggling to get everyone in the prospect company on the same page. So, the #1 challenge now is, once we have the meeting, how do we continue the momentum? There are usually 8-12 people involved in making the decision and it’s difficult to get people to want to fix the problem and agree on the solution. This is worse now with COVID19.

Gadi Binness
Relocation Insurance Group, LLC

Gadi’s sales team consists of 2 Sales Admins, 2 producers and a Director of Sales and Business Development who manages the 2 Sales Admins and the 2 producers and who also does business development. Gadi is also involved in sales.

Gadi said that his #1 challenge in managing a sales team is technology. He said that they are still doing some things manually and that cuts down on their efficiency and productivity. The challenge is to upgrade and update the technology they use in order to be more productive. Interestingly, the company has always worked remotely and so they were not affected, the way many other companies have been, by having to make a major shift in how they work.

I asked Gadi what he sees as his #2 challenge in managing a sales team. His answer, “Bringing more leads and accounts into the pipeline. Bringing in more business.” He said that for his business, “The challenge moving forward, if this crisis continues, will be bringing in business.”

Ron Clevenger
Mustard Seed Financial & Insurance

Ron’s sales team consists of 10 insurance producers. They are all 1099, independent, commission-only, contractors whose focus is to go out and find new business.  Once an account is closed, there is a customer service team that manages that account. This allows the producers to continue to sell and find new business.

Ron said that his #1 challenge in managing a sales team is to have visibility into the early stages of the sales funnel, pre-quote and pre-negotiation. His blind spot is having a strong indication, at the highest level, how the early stage sales funnel looks. He does not have an easy way to know if the sales funnel is shrinking or if it is expanding.  It is difficult to have a measure of what the producers are doing in terms of meetings scheduled and/or in-depth conversations with prospects. Ron said that It’s easier to understand what the funnel looks like once producers get into the quoting process because then there is a good paper trail.  Ron says that the current pandemic has not had an impact on this challenge.

In thinking about what has changed since the current crisis began, Ron said, “Momentum and the learning that happens when the team can come together face-to-face.” He went on to say that, “When you have traditionally been a sales organization that operates under a brick and mortar roof and now, you’re operating remotely, your level of engagement is not as great. There’s less discussion of successes and failures, what’s working and what’s not working. It’s not the same as when everyone was sitting around a conference table together.

Ken Dawson
Mindrover Technology LLC

In the past, Ken had a sales team but right now, he is the sales team. Ken says that his biggest challenge has been, “Finding the right person in the company to talk to. It’s a matter of getting your message to the right person.”

Ken also experiences a conflict between outbound marketing and inbound marketing and determining which one is the better approach. Ken is trying to do both at the same time. For outbound he’s working on a mix of cold calling, cold emailing and text messaging. For the inbound piece he is implementing a content marketing strategy in order to be seen as a subject matter expert by the prospects he’d like to meet.

When I asked Ken, what has changed for him since this crisis started, he said, “Now everyone is shut down and the message isn’t getting out. I’m having to rely on inbound marketing; people coming to me looking for technologies or strategies to work remotely. I was lucky, however, because I had just put up a landing page on my web site about strategies and products for working remotely and how my company can help. I did this one week before the quarantine hit.”


We help business owners that are sick of micro-managing their sales team turn their team into efficient, effective qualified appointment-setters. If you’re a business owner managing a small, not-producing-at-the-level-you’d-like, sales team, let’s talk. Simply click here to schedule a time for a New Appointment Breakthrough session, give me a little background and we’ll talk.


Independence Day?

I was never supposed to be The Queen of Cold Calling… I was supposed to be a ballerina.

If you’ve ever been on one of my webinars, you may have seen the picture of me when I was 5 in front of the house where I grew up in Pittsburgh, PA before my very first recital.

When I was 17, I moved to New York City (where I still live and work) to dance. I studied at the Joffrey Ballet School.

Eventually, like every artist in New York City, I needed a day job. I got very tired of waiting on tables, so then I got a job with a telemarketing agency that did new business development. It turned out that I was good at it. Who knew? Because ballet dancers do not talk—we dance we don’t talk.

I did that day job for a while and then I started my own business doing business development on behalf clients. It was one of those first clients that dubbed me, “The Queen of Cold Calling,” because I found so many new opportunities for him.

After that beginning, I segued into the business that I have today. For the past 20+ years I have helped business owners, entrepreneurs and sales professionals use the phone and all of the tools that are available to develop new business.

My own business thrives and I never worry about where the next sale will come from because I know how to prospect. I am independent. My clients have gone on to have successful businesses and sales careers. They also do not need to worry about where the next sale will come from. They now know how to prospect. They are independent.

Here’s the point that I would like to make today: What gave me my independence (and what gives my clients their independence) was learning this all important skill of prospecting and connecting with prospective new clients.

You may have heard that in order to be really successful in sales you need to be a “born salesperson.” This is not true. I was never a “born salesperson,” I was a ballet dancer. I was simply really, really lucky because early in my career I learned this skill and learning the skill enabled me to find clients and grow sales.

True independence, financial independence and spiritual independence, comes from not having to worry about where the next sale is coming from.

On this day of independence, if you or members of your team are struggling or if you simply want to take sales to the next level, there is help available. It is unlikely that you will figure it out on your own. Luck may or may not strike. The really good news, however, is that prospecting is a communication skill and like any communication skill, you can learn it and you can improve on it.

Stay tuned for more…

Burnt Out

By Wendy Weiss, The Queen of Cold Calling™

Today I’m sharing a question from reader who writes:How do I keep from being burned out while prospecting? My job is to call current customers and to also call new business prospects. I have a quota of 60–80 calls to make per day, but it seems as though I cannot stay focused long enough to make even 50 phone calls. By the time I get finished calling my current customers and servicing their accounts, I am mentally burned out. I am in no state to begin calling for new business. What advice/strategy do you recommend to keep me “pounding the phone” and “dialing for dollars”?


This is an excellent question, and one that comes up for many people who conduct business over the telephone. Phone work can be exhausting. It is an intense experience. You must stay focused, listen carefully, assess prospects and respond quickly.

That said, 60 – 80 calls per day is a lot unless you are using some kind of efficiency tool like a dialer. Quality is always better than quantity. (For recommendations on prospecting efficiency tools, see Wendy Recommends below in this newsletter.)

Make your new calls first. Schedule a specific time every day to make new calls and only new calls. When the time that you have scheduled is up – stop. Then, go on to your customer service calls.

Be sure to give yourself breaks throughout the day. Get up every hour and stretch. Walk around your office. Drink plenty of water throughout the day, so that you aren’t dehydrated.

Give yourself incentives. For example, every time you complete a predetermined number of calls, put some money ($1, $2, $5…) into an envelope. At the end of the week, take that money and treat yourself to something—even if it’s only an ice cream cone.

Find a “buddy” in your office (or outside your office) to whom you can go to for a pep talk now and again.

Gather testimonial letters from customers. Make copies and post them prominently near your desk. Take a yellow highlighter and highlight all the really good parts. This way when you feel a little burnt; you can remind yourself of all the wonderful things customers have said about your offering.

Recognize that what you are doing is difficult, and give yourself credit for what you accomplish. Remember that all of your current customers were once new customers, and before that, they were probably new calls. Think about the all benefits you bring to your customers. You will bring those same benefits to the new calls that you turn into customers. Make a list of those benefits, and also post that list prominently, so that you can look at it when you need a boost.


Are you missing Step 1?

I was recently working with a new coaching client. His mission is to set up appointments on behalf of his manager. My new client was stressed and frustrated and having no success.

He told me that he was reaching and having brief conversations with some prospects but those conversations went nowhere. He said he was trying to be consultative, to elicit details and to drill down on prospect objections. But no matter what he said or did he would hear, “I’m not interested,” and a click as the prospect hung up.

This new client is not a beginner. He has been in sales for many, many years. He told me that he believes in a consultative approach to prospecting and selling yet he was struggling schedule even one appointment.

Here is the fundamental problem: Consultative selling does not work for prospecting. You cannot consult with someone that will not engage with you. You cannot get answers to your questions, elicit specific details or drill down on anything at all until a prospect agrees to speak with you. Step 1 is getting the prospect’s agreement to have an in-depth conversation.

Many sales professionals that are prospecting want to set an appointment with their prospect. That appointment might be a face-to-face meeting, it could be an online meeting or the entire process could be by phone. That appointment is your prospect’s agreement to have an in-depth conversation with you. Get the agreement first.

Once a prospect has agreed to an appointment everything changes. It means that they are willing to talk to you. They are willing to give you time. They are willing to engage with you. You can ask open-ended questions, gather in-depth information and even offer solutions when appropriate. Prospects will answer your questions, give you concrete, specific information and even ask you questions – once they have agreed to speak with you.

Prospecting versus selling is the difference between asking to have a conversation and actually having that conversation.

Prospecting and selling are two totally different skill sets. Unfortunately, the two are often taught as though they are exactly the same. They’re not. When you use the wrong skill set for prospecting it is a struggle. Get the appointment first–then consult. That’s the only way it will work.


“I Just Called to See How Things are Going”


This is a sad story. Sad but true. It was a real conversation, ostensibly a sales conversation. This sales conversation, and many others just like it, are happening all over the world. I recount this sad sales conversation here in the hope that everyone may learn from it…

Sales Representative: “I just called to see how things are going.”

Wendy: “Things are going fine. Why are you calling?”

Sales Representative: “I just called to see how things are.”

Wendy: “Things are fine.”

Sales Representative: “OK. Well I’m here if you need me.”

Wendy: “Why should I need you?”

As it turns out, the company this young man represented was supposed to be scheduling a demo of a product for my staff and for me. My wonderful assistant, Kim, usually takes care of scheduling for these types of events. When the rep called, I was working on a program that had an approaching deadline. This company’s demo was the last thing on my mind. I didn’t make the connection and I had absolutely no idea why this rep was calling me. Clearly, neither did he.

“I just called to see how things are going” has to be the lamest follow-up question of all time. Although, it is running neck and neck with, “I just called to follow-up.”  Neither question elicits any information, neither moves the sales process forward and both are frequently annoying to your prospect who often has absolutely no idea why you have called.

Now in all fairness, this rep was not the original contact and perhaps the original contact did not give him all of the background. Or perhaps that original contact did not have good notes in the CRM. Either way, this rep should have tried to get some basic information from someone, the original contact or perhaps his manager: “What is the purpose/goal of my call?” “What is the history here?” “Where are we with this prospect?” “What is the next step for this prospect?” Any of these would have sufficed. Then this representative would have had a focus and a goal for his call.

The rule is: Never make a call to your prospect without having a goal in mind. When you hang up the telephone, what do you want to have accomplished? Do you want to gather information? Do you want the prospect to commit to some action? Do you want agreement on the next step in your sales process? Once you have your goal in mind then determine the appropriate approach. (Hint: “I just called to see how things are going” is not it.)


“Call me in January…”

Many, many business owners and sales professionals believe that the holidays are a bad time for prospecting. Not true. The holiday season can be an excellent time to prospect. While it is true that some decision-makers are on vacation and others are out holiday partying… many are still hard at work, reachable and willing to engage with you.

December can be a slow month in many industries, some people are on vacation and in most offices things do tend to slow down.  What this means is that prospects may have more time to speak with you and/or to meet with you. And, because things are slower, prospects are frequently less harried and stressed out. This is always good news.

One objection that you’ll encounter in December and no other time is the objection: “Call me in January.” While some prospects will be willing to engage with you others will not and they’ll ask you to call in January or after the New Year.

At one time, this could be an insurmountable objection. People actually had physical calendars and in December many of them had not yet purchased their next year’s calendar. This made it impossible to schedule appointments in January. Even with prospects that wanted to schedule an appointment, you’d still have to call back because they literally did not have a calendar.

Today, of course, this is a nonissue. Prospects have calendars for next year, the next 10 years or the next 20 years…. So as you are prospecting this holiday season, when a prospect says to you: “Call me in January” or “Call me after the New Year” this is what you say:

“Let’s pencil something in for January (for after the New Year). It’s not chiseled in stone, I’d be happy to give you a call to confirm. Is (January date) good or is (different January date) better?”

This way you’ll be able to hit the ground running in January with a pipeline full of solid appointments and qualified opportunities.

Happy holiday prospecting!

It’s the Holidays!

Thinking that you should cut back or give up on prospecting altogether during this time of year? What to do when…  

It’s the Holidays!

By Wendy Weiss, The Queen of Cold Calling™
  1. No one’s doing any work. It’s the holidays.
  2. Nothing gets done till January. It’s the holidays.
  3. No one sets appointments till the New Year. It’s the holidays.
  4. Too much to finish up to take the time to prospect. It’s the holidays.
  5. Prospects are taking time off. It’s the holidays.
  6. I’m taking time off. It’s the holidays.
  7. My assistant is taking time off. It’s the holidays.
  8. Their assistant is taking time off. It’s the holidays.
  9. No one wants to be bothered. It’s the holidays.
  10. No one is thinking about work. It’s the holidays.
  11. Prospects leave the office early. It’s the holidays.
  12. Prospects go to the office late. It’s the holidays.
  13. Everyone is having office parties. It’s the holidays.
  14. No one’s thinking about business. It’s the holidays.

Ha!Prospects do conduct business, even during the holidays. Years ago it was possible for a prospect to say, “I don’t have my calendar for next year, call me after the first of the year.” Today prospects have their calendars on their computers, tablets or phones and can schedule appointments for next year or even several years out if they are so inclined.

Prospects make appointments before, during and after the holidays, just as they do at other times throughout the year. If a prospect asks you to call back after the holidays, suggest that you “pencil in a meeting for after the holidays.” Promise that you will call to confirm it. Do so.

Happy holidays!

Are You Selling?

Many sales professionals believe that they are not actually selling. So that is the question for today’s article… 

Are You Selling?

By Wendy Weiss, The Queen of Cold Calling™

I looked up the word “sell” in the dictionary. This is what it said:

“To persuade (another) to recognize the worth or desirability of something.”

This definition assumes value. The concept of worth or desirability is inherent in the definition of the word.

I also looked up “salesperson,” “saleswoman,” “salesman,” “sales clerk,” and my favorite, “sales talk.” The definition for “sales talk” was, “a line of reasoning or argument intended to persuade someone to buy something.”

I often ask clients, “What are the words that come to mind when you hear the word, ‘salesperson’?” Invariably, I hear back words like, “manipulative,” “dishonest,” “unethical,” and “sleazy.”

In the dictionary, however, when I looked up all of the above sales words, none of the definitions referenced “manipulative,” “dishonest,” “unethical,” “sleazy,” or anything particularly negative. The language in these definitions was actually quite neutral and several of them spoke of value.

Unfortunately, the words “sales” or “sell” no longer simply mean to persuade someone of the value of your offering. Instead they carry the baggage of images of untrustworthiness and deviousness. This is a misconception that does an enormous disservice.

Far too often, sales professionals believe this stereotypical image of sales and see the activity of selling as negative. They feel that if they are selling (or being perceived to be selling), they are doing something that is not quite right or that has the potential to be not quite right. This puts them, in their own minds, at a disadvantage and on a lower level than their prospects and customers. This is a difficult place to be. And it stops many from taking action.

Since the definition of the word “sell” used the word “persuade,” I looked up that word in the dictionary. It said:

“1. To prevail on a person to do something, 2. To induce to believe; convince”

Again, nowhere in that definition do we find the words, “manipulative,” “dishonest,” “unethical,” “sleazy,” or anything particularly negative. As with the word, “sell,” the language is quite neutral.

The bottom line: Selling is persuading and convincing people to buy your offering. That persuasion is based on value. If you cannot persuade and convince people to buy then you do not have a business.

If you believe that selling is “manipulative,” “dishonest,” “unethical,” and “sleazy,” this belief will not support your ability to sell successfully. It is very difficult to sell (persuade and convince) while believing that selling (persuading and convincing) is wrong. It is time for sales professionals to change their beliefs about the words “selling” and “sales.”

The truth is that most sales professionals are honest, ethical and believe in the value they have to offer. And that is where the focus should be.

Here are some questions to ask yourself:

  1. Do you believe in the value of your offering?
  2. Does your offering provide a value to your customers?
  3. Are you doing the best you know how to ensure that your customers receive that value?

If you have answered “yes” to the above questions, then you are proceeding with integrity. If you are proceeding with integrity, then obviously you are not being “manipulative,” “dishonest,” “unethical,” and “sleazy.” You can persuade, convince and sell with your head held high.

If you answered “no” to the questions above, then get out of the business. It’s not a fit for you. Find something else to do in which you can believe.

Let’s reclaim the words “sell” and “sales.” Let’s redefine the words to mean, “To persuade and convince with integrity.” Let’s remember that value is inherent in the definitions of those words. Then hold your head high and go out and sell.

If you feel like you could use some help and support to hold your head high, sell with integrity and fill your sales funnel with qualified opportunities that are likely to become customers then I invite you to fill out the application for the 2017 Prospecting Jumpstart program where you will coach directly with me, one-on-one, to achieve and exceed your goals. I am looking for only a handful of people who want to knock it out of the park in 2017. To see if the 2017 Prospecting Jumpstart program is right for you, I invite you to begin the application process.


Are You an Amateur or a Professional?

Recently I had a conversation with a friend, a former, highly successful model, who is now building a successful business. We’re both entrepreneurs so we discuss our businesses, we egg each other on, give each other advice, we commiserate…

My friend was feeling frustrated. “Amateurs,” she said. “I’m tired of dealing with amateurs.”

I knew what she meant. A professional is someone who shows up, no matter what. A professional is someone who gets the job done, no matter what. A professional is someone who does what she needs to do, when she needs to do it, no matter what. An amateur is someone who lets circumstances, other people and emotions get in the way.

As my friend put it, “When you’re a model, if you have a saggy butt, they tell you that you have a saggy butt. Then they tell you to go away. If you want it enough, you fix your saggy butt and go back.”

I grew up in the ballet world. It’s very much the same. You take class everyday with a teacher whose job it is to criticize you. The criticism is to help you improve, but some times it just feels like criticism. You dance in front of a big mirror. This is so that you can criticize yourself.

As an adolescent and even a young professional, I’ve been called “a cow” because of a few extra pounds. I’ve had teachers hit an errant arm or leg with a stick because that arm or leg was in the wrong position. (No, they weren’t singling me out, they hit everyone.) I’ve lost dance jobs because I was too tall, too short, or had the wrong color hair. I was not accepted into the renowned Harkness Ballet School (I was 13 at the time) because my back was too long. (They told my dad I was a very good dancer, but…) When I cut my hair short (it used to be down to my waist so that I could put it up in a classical ballet bun) I never again, got another job as a ballet dancer. And by the way, when you go to a dance audition they don’t let you dance. They simply line you up and look at you and then start eliminating dancers. Once they’re done eliminating, the dancers that are left get to actually dance.

When I first started doing sales training and clients would talk to me about rejection and fear of rejection I had no idea what they were talking about. While those feelings can be very real, it’s how you handle them that makes all the difference.

Sales is tough. Everyone will not love you or your offering. Everyone will not say “yes.” The stark reality is that some prospects will say “no.” A career in sales is not for the weak.

The key to success is what you do with that “no.” You can allow it to stop you, or you can put it aside and continue on. The power is entirely yours. If there are people in the world having success doing exactly what you want to be doing, there is no reason that you cannot do it too.

Being a professional starts with your mind set, that you believe in what you are selling and that you do not give other people, circumstances or even your own thoughts and emotions the power to stop you. Or as my friend put it, “If you want it enough, you fix your saggy butt and go back.”

4 Reasons that Your Follow-up Fails

Why is following up so difficult for so many? Why do so many prospects fall through the cracks? Why does every sales professional know they should follow-up and why do so many fail to do so?


4 Reasons that Your Follow-up Fails

By Wendy Weiss, The Queen of Cold Calling™

1. Lack of prioritization

If you’ve been in sales for a while it is impossible to touch everyone personally by telephone. You simply don’t have the time.Many sales professionals, however, treat every prospect exactly the same way. They follow up with every prospect in exactly the same manner. They follow up with teeny tiny opportunities the same way that they follow-up with huge opportunities.

The harsh reality is: All prospects are not equal.

All prospects do not require the same follow-up. Spend the bulk of your follow-up time with those prospects that are most likely to buy from you.

2. Lack of organization

Following-up effectively takes organization. You need to know which prospects you are following up with, what has already transpired and what the next step is in your sales process. Appropriate software solves many of these problems. Today it is simply too difficult to rely on Excel spreadsheets or your notebook.

3. No system

In order to follow-up effectively, you’ll need to determine: How will you follow-up (phone call, email, etc.)? What are your goals for each communication that you have with a prospect? How often should you contact your prospects? When should you let a prospect go? These questions, along with many others, need to be answered before you even begin. Too many sales professionals do not take the time to develop their process and so are left winging it every time. When you have a process in place with scripts and templates it is much easier and far less time consuming to reach out to the prospects you need to contact.

4. Fear

Fear of rejection can keep sales professionals from following up adequately, or at all. Many worry they are being “too pushy” or think, “If the prospect is interested, they’ll call me.” Some fear the anticipated devastation of having a prospect say, “No.”

Prospecting and follow-up are business transactions. Prospects may say “no” to your offering. They are not saying “no” to you.

Failed follow-up can be fixed. Eliminate these reasons that your follow-up is failing and see the results in your bottom line.