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How Overcoming Obstacles in Life Applies to Sales

Posted by Steve Bookbinder on Mar 23, 2017 7:45:54 PM

Today’s salespeople must be versatile.

On one hand, you have to be great at classic sales skills like prospecting, verbal and non-verbal communication, as well as time management.

On the other hand, you have to be willing to adjust and reinvent your approach to incorporate new skills and technology. Your own company’s products, services, marketing support and competitive advantages will continue to evolve in order to keep pace with the rapidly changing marketplace.

Everyone is now selling more complex solutions and they are selling across many platforms to a growing number of influencers and decision makers.  And guess what? Your competitors are working hard to beat you and they are targeting your customer’s budget. 

So, this means we have to be innovators and pioneers too, especially when it comes to reaching bigger goals and overcoming obstacles along the way.

That’s why I’m sharing my story about how success in sales is a lot like successfully swimming the English Channel, which is the world’s hardest open water event.

In 2008, I successfully swam the English Channel as part of a 4-man relay. In 2009, I had my next English Channel. This time it was to launch a successful company in the middle of a recession after losing my job. In both the real and metaphorical English Channels, I was determined to succeed, but had an even stronger desire not to fail. 

Selling is filled with English Channel challenges. And it’s a metaphor you can apply to any challenging goal that you don’t want to fail at achieving.

Here are the 3 things I learned about overcoming English Channel challenges and how it applies to sales:

How to overcome obstacles in sales and life

#1 Getting in Shape

As soon as I agreed to join the 4-man relay, I knew I was out of shape but I wasn’t quite sure what type of “in shape” was needed?

What I learned was the importance of crafting the right description of your goals. Anyone can get “in shape” but if you’re going after a specific goal, then you need to be as descriptive and specific as possible.

Lessons applied to sales

Know Your Starting Point

Be honest with yourself by assessing your current position. What are your strengths? What are your weaknesses? Are there risks involved in going after this goal? Or are there more opportunities available? Your starting point will help you determine how to take your next steps.

Commit Yourself to the Goal

When you’re committed to a goal with relentless focus and determination, it makes the inevitable roadblock more bearable. This is because if you hold yourself accountable, then you will take responsibility to think of every possible idea or path to make it to the finish line.

Organize Yourself around a Task

If you’re focused on achieving a big goal by a certain deadline then you have to align and organize your time, your activities, and your resources. If you’re trying to get X number of appointments each week, then you need to ensure you’re organizing yourself around this goal or task.

Develop a Dashboard to Track Progress

If you want to improve, then you have to establish benchmarks. This is so you can compare your current position to your progress along the way. Let’s say you want to improve your customer retention rate, then you need to track how many clients renew at the end of each contract. When you see yourself improve, you are more motivated to keep going.

Leverage the Power of Negative Thinking

Imagine you’ve missed your goal. You’ve failed to successfully cross the Channel. Now what? Well, when those feelings of disappointment creep into your mind, they will trigger ideas and insight. All of a sudden, the things you should have thought of or didn’t know become clear. This is especially helpful when applied to sales because you now know what you would have done differently. But usually it’s too late. So, before a situation like this occurs, consider leveraging your feelings of disappointment to generate ideas about what you “should” have done in advance of missing the goal.

#2 Jumping into Cold Water

The thought of it is worse than it actual is, but fear of the unknown is an element that often stops people in their tracks. When you’re navigating obstacles, you will experience a lot of cold water that you’ll have to dive in head first. But when you prepare and anticipate you’ll be well positioned to face this type of obstacle and overcome it.

Lessons applied to sales

Take Small Steps

Break down your goals into small steps. No matter how unpleasant the thought of doing something may be, if you break down a bigger task into smaller steps, you can think in terms of minutes or days instead of hours or months. Adding one more minute of training, or one more prospecting call to the end of the day, you’ll be one step closer to reaching your goal.

Do Your Research

The more you know, the better off you’ll be. When you do your research and consider the information available, you can interpret and apply what you’ve learned to inform your decisions. In sales, it’s now standard operating procedure to be knowledgeable and prepared prior to every meeting.

Know Your Weaknesses

Mostly everyone would succeed in an ideal setting under perfect conditions. But what matters is how you react under pressure or difficult circumstances. In sales, there are many instances that lead to stress or uncomfortable situations that need to be dealt with professionally and proactively. That’s why you must acknowledge your weaknesses and work towards improvement.

#3 Avoiding Jellyfish

What is your personal kryptonite?  When you fear failure, what does that fear look like? When you brain is yelling: DANGER! How can you stay relaxed enough to recognize the fear while remembering and practicing your new reaction.

Lessons applied to sales:

Reinvent Yourself

When you’re set in your ways and have established patterns or habits, nothing short of shaking things up by trying something new will help you face your personal fears. Everyone has a fear of change, to an extent. But when you’re on a constant mission to break old habits, you begin training yourself to change. This takes time, but once you get started you’ll have renewed energy and enthusiasm for the goal you’re trying to accomplish.

Keep Training

When you’re constantly training and engaged in ongoing development, you become very good at absorbing information and then applying it to your own situation. If you stop learning, just like exercise, your muscles will atrophy. Consider finding yourself a mentor or coach who will advise and guide you on an ongoing basis.


Both life and sales are full of uncertain obstacles and rough waters, but when you have a willingness to learn and reinvent yourself as well as make an effort to prepare, anticipate, and hold yourself accountable you can pioneer your success.

Tune in to the DMT YouTube channel for weekly tips.

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Topics: sales tips, sales training, overcoming sales challenges

Selling Complex Solutions and Why Conventional Sales Training Won’t Work

Posted by Steve Bookbinder on Mar 9, 2017 8:15:00 AM

Your technology or solution fits the client's needs but they are currently using another solution. While selling against the competition is a common problem for salespeople across all industries, advertising and marketing technology or software solutions challenge salespeople in a way that conventional sales training and product training doesn’t address.

Selling innovative technology requires a new multi-platform approach to training that goes beyond just building confidence to providing the right understanding and resources needed to win the first few sales.

Now, some people would like to believe that technology just sells itself, but consider the key element in closing every sale: interaction with a salesperson.

The relationship between the buyer and seller as well as their respective organizations is a major competitive advantage when selling technology.

While the buyer has most likely conducted their own research to first understand, frame, and give a name to their problem or opportunity, their motivation to buy really comes down to whether your solution is a good business and personal fit.

The buyer makes a decision based on how well the salesperson is able to connect the dots between the customer’s needs and how the solution will be the right fit to address those needs.

If it were just the technology, you wouldn’t need the salesperson. 

But since that’s not the case, here’s why you should kick conventional sales training to the curb and focus on winning more sales with these ideas:


Be an Expert

Traditional sales training is typically built on the premise that you must memorize and regurgitate facts, figures, features, and benefits of your products and services. While yes, salespeople must know this information, the problem is that a lot of companies lump “selling skills” and “product knowledge” training together when they should be completely separate programs. Selling skills training is all about how you communicate your message. But the first step is having a solid understanding of the product and market knowledge prior to learning how to present the solution.

You can be an expert by focusing on:

Knowing the Market

Understanding our target market and niche is critical. We need to understand the unique circumstances, competitive environment, and business processes of our target market. In doing this research and preparation, we are better equipped to address the needs of our target market and identify what core business challenges our technology can address.

Knowing the Client

We need to go beyond the market and spend time getting to know each individual company’s situation and circumstances. Each client will have unique business challenges and processes that need the support of technology in a customized way.

Factors that will affect the type of solution needed will vary depending on their stage of business growth, current processes and systems in place, business goals, and management methodology.

BONUS: Here's a video from our CEO, Steve Bookbinder, about how to stay knowledgeable and up-to-date on the latest trends going on in your industry:

Be Curious

Typical sales training is focused on you and your company. However, in the real world of selling you will only have success by focusing on the customer.

Sellers must work towards building a deeper connection and trust with their buyers in order to be successful when selling their technology solution.

To do that, you must master the art of being curious and learning how to uncover needs by going below the surface of the sales conversation.

My advice is to practice asking 2nd level questions and 3rd level questions.

For example: Let’s say it’s a first appointment where you’ve proactively prospected to get the sales meeting. The prospect begins by telling you, “The reason I wanted to meet you is that we are currently looking to change vendors and I thought your solution might be what we are looking for.”

Typical response: “Great! Tell me more about what you’re looking for.”

Below the surface response: “Before I go into our offering, can you tell me why you originally chose your current vendor and why their approach hasn’t worked for you? Did something change?”

Finding a solution that fits the customer requires going below the surface of what was explicitly said so you can ask about the implicit – what you deduced from the customer’s words.

Be Prepared

While conventional sales training may address how to turn around sales objections, it doesn’t teach you the strategies necessary to anticipate and handle new objections.

Most salespeople sound confident when they already know what they are going to say before they say it. They are at their worst when they don’t know what to say. And nothing can stop a salesperson more than fear of not knowing how to answer a question or turn around an objection.

My advice is to encourage all sellers to share the objections and questions they’ve been getting on a weekly or monthly basis. This will provide real world examples so that you can continually practice and refine your answers. This is also a great way for the whole team to share essential information that will help everyone do their job more effectively. 

Be a Problem Solver

Elevating ourselves from the status of order taker to trusted advisor and problem solver can give us a real advantage in the marketplace.

To do that, it’s imperative that salespeople understand the strengths, weaknesses, and limitations of the technology.

Start by mastering the specialist vs. umbrella argument. Either your company offers all related services under one “umbrella”, or you specialize in services that umbrella companies offer, too, but your version is better. 

Umbrella companies offer a single point of contact and the ability to move services to the ones the client needs.  Specialists are stuck only providing their one service which may not be the right fit over time.  But, if you are a specialist company, your argument is that no one else can reach your level of specialty and for that reason the fit with the customer’s needs will be closer. 

By understanding our limitations and setting expectations early on through effective communication, we can dispel any misconceptions the client may have and avoid misunderstanding or off-target results. Truly knowing all about your solution will help maximize revenue and client satisfaction.

My advice is to develop this “positioning” skill. It requires ongoing verbal practice; over your career at various points you will need to be an expert on one side or the other of this argument. To be seen as a consultant, we need to have a thorough needs analysis approach, build our profile as a subject matter expert, have a high level of rapport with the potential clients, and look for ideal solutions—not just “our solution” to client problems.


Traditional sales training needs to evolve into a more comprehensive approach. Because to become an excellent salesperson, it’s less about selling skills and product knowledge, but more about your ability to translate your message and make a connection to the buyer and their problem.

Tune in to the DMT YouTube channel for weekly tips.

Editor’s Note: This post was originally published in October 2016 and has been updated.

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Topics: sales tips, sales training, solution selling

Ask These 4 Questions for More Effective Calendar Management

Posted by Steve Bookbinder on Mar 2, 2017 2:30:44 PM

Effective time management is arguably one of most important skills for sales professionals to have.

However, according to research from The Bridge Group, sales productivity is the #1 challenge for almost 65% of B2B organizations.

Increasing sales productivity and providing time management tips have become a catchall solution to this growing challenge, but have you ever considered that the root cause of the sales team’s problem may not be about managing time, but rather managing attention.

The best sales organizations help their salespeople maximize time spent on high value tasks and opportunities while minimizing time spent on low impact or dead end opportunities.

When I coach sales teams, I need to first understand how each salesperson is using their time and what activities they are prioritizing. To do that, apply the following questions to assess your current level of calendar usage and how you can improve your skills in order to increase sales productivity.


Question #1: How many appointments do you have scheduled over the next month?

This questions is important because it provides insight into how much prospecting and/or account management is happening over the course of a month.

Sure, each month is different, but when you have an understanding of how many appointments you need per month in order to reach your quota, then you’re able to use your calendar as a measure for success.

If you’re finding gaps and a lot of free time in your schedule, then consider that a warning or red flag that means you need to increase your prospecting efforts in order to fill your pipeline and your calendar.

Question #2: How much time per month are you dedicating to activities that will help you achieve a long-term goal?

Setting and achieving long-term goals is a process. It’s a process that first starts with recognizing what you want to achieve, and then putting a plan in place to actually get it done.  It also means holding yourself accountable.

For example, let’s say you’re working on major project like writing a book, which could take 6 months up to a year. Each week, it’s critical that you take a small step forward. But in talking to a lot of aspiring entrepreneurs about long-term goals, I found one of the most common errors made was not taking into consideration the importance of aligning your current day-to-day schedule with future goals. In other words, if you don’t make time today, then you won’t make progress tomorrow.

You can avoid this error by scheduling an appointment with yourself every day or week, depending on the urgency of your goal, where you spend time assessing and measuring your progress as well as taking an action that contributes to your overall plan.

Question #3: How often do you schedule time to work on your business instead of in your business?

There is a major difference between working on your business versus in your business. When you’re working on the business, you’re focused on the company vision, building a strong team, and high level improvements. Whereas when you’re working in the business, you’re focused on the day-to-day minutia and operations. When applied to sales, think of your “business” as your approach to selling.

This means you need to spend time looking at your sales strategies and techniques from both of these perspectives. You can do this by scheduling an appointment with yourself to review the following items.

What to think about when you’re working “in” the business:

  • What project or task should I be focused on right now?
  • What does my sales pipeline look like?
  • Am I making progress towards my sales goal for the month?

What to think about when you’re working “on” the business:

  • What daily tasks would benefit from being automated?
  • What kind of professional development or training should I be doing?
  • How do my KPIs from this month compare to last month? Or this quarter compared to last quarter?

While this certainly isn’t a complete list of key points to consider, it is a starting point to help you understand the distinction between these two ways of thinking and planning.  

And if you’re not currently using a tool to help you track, measure, and organize these things, then check out my C.L.E.W. report here to get a jump start.

Question #4: How often do meetings creep into your calendar that you weren’t prepared for?

Being in sales means making every effort to be as organized and prepared as possible. While we know it’s unrealistic to think a surprise meeting or phone call won’t pop up, but there are a few things you can do to limit that from happening.

First, as mentioned above, when you schedule appointments with yourself to work on your priorities, you’re less likely to have your time taken because your calendar will show you’re busy during that time. And usually if someone is trying to coordinate a meeting with you, they will either ask if you can move something around, or they will avoid that day/time altogether because it’s shown as busy.

Second, review your calendar at the end of each day for the next day, and at the end of each week for the following week. This will not only help you manage your time better, it will also provide an opportunity to assess where you can schedule more time into your day or week to work on key projects and priorities as well as items that need to be rescheduled or moved to the backburner.

Finally, make sure your calendar reminds you about 10 to 15 minutes before a meeting. This not only alerts you of the upcoming meeting, but also gives you a chance to wrap up what you’re currently working on and switch gears to the next meeting. This is important because it gives you a chance to clear your head before going into the meeting, and provides an opportunity to review any last-minute information to help remind you of the details that will be discussed.


When used properly, your calendar can be one of your greatest sales tools. It acts as both a sales preparation and planning tool, while also keeping you focused and up-to-date on time sensitive items.

Use the 4 questions mentioned above to assess how you are currently using your calendar and what improvements can be made in order to leverage your time more effectively, which ultimately leads to an increased level of sales productivity and a renewed sense of control and organization.

Remember, the best salespeople maximize time spent on high value tasks and opportunities while minimizing time spent on low impact or dead end opportunities.
Calendar Management Checklist

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Topics: sales tips, sales tools, time management, sales skills, calendar management

3 Strategies for Effectively Developing the Right Calling Approach

Posted by Steve Bookbinder on Feb 23, 2017 8:19:00 PM

Whether you’re new to sales, or an experienced pro, developing the right approach to making sales calls is a strategic advantage.
As a salesperson, oftentimes the first impression you make is over the phone. Whether that’s talking to a new prospect, building a client relationship, or maintaining contact with long term clients.
Developing an effective calling approach and phone persona is essential to your sales success. But how can you develop an approach that will consistently drive results?
Consider these 3 strategies as you develop, refine, and optimize your calling approach: 
sales call approach ideas

1. Personalize Your Message

Think about who you are calling and why you are calling them before you pick up the phone.

First, we must consider what kind of leads are you calling and what’s the right strategy for each?

For example, let’s say you were just assigned a new lead. This lead came in through the website as an inbound lead who downloaded your newest eBook. What’s the approach for this type of lead?

To start, we must do our best to research who the person is, what company they work for, why they might be interested in the eBook, and whether they’ve downloaded any other resources from your website.

Why are these things important?

Because each piece of information helps you paint a picture of who you are calling. The more you know about the company, the person, or the industry in general will set you up for success because you’ll be able to tailor your message by saying something that resonates with the lead.

In this inbound lead example, you could personalize your message in a simple, yet logical way by helping them identify the key takeaways from the eBook they just downloaded and offer ideas about how the information applies to their job, company, or industry.

Taking this approach helps you position yourself as an expert, presents your company/offering in a positive light, and lets you take the role of the helpful salesperson who is educating them on new information and solutions.


2. Build Your Sales Story

 Identifying the right approach for each type of lead is only part of the game. The next step is to build your value proposition by crafting a compelling sales story.

We often think that facts and figures are what motivate people to take action. But the truth? Facts and figures aren’t nearly as effective as telling a great story.

Let’s say you’ve got a prospect on the line and they want to learn more about your solution. Instead of rattling off numbers that will mean nothing to them, consider walking them through the story of how you’ve helped other companies, maybe even mention a competitor of theirs, and help them visualize how your product and/or service delivered results for that company.

For example, you could say something like: “We’ve had a lot of success with companies like yours who have experienced some of the same challenges you may be facing, so I’d like to learn more about what you’re doing, tell you how we’ve been implementing solutions for businesses like yours, and see if there’s a match.”

You’re not only going to get their attention fast, they’re going to want to know how they did it, when they started doing it, how far behind they are, and what they need to do to catch up.


3. Understand the Rhythm of the Call

Listening is the key to a great conversation. So when we are speaking with prospects and clients over the phone, we must listen to the rhythm of the call and make certain decisions based on the rhythm.

If you ask a question and the other person responds as soon as you finish speaking, this probably means they’re tuned in. On the other hand, if there’s a long gap and their response doesn’t really relate to the question you asked, they’re probably not connected to the conversation.

As sales professionals, our goal is to ask 2nd level questions in order to create a more substantial conversation. 2nd level questions, asked in the right context, encourage the customer to share relevant information needed to understand their true interest in our business solution as well as their motivation to help their organization acquire it.

This is the type of conversation when the customer reacts to the salesperson’s interest and capabilities by sharing relevant information about their background, biases, plans as well as their power, influence, and motivation to buy.

The best way to help them make more sales is to maximize their time with people most likely to buy and minimize their investment in time with the rest.  At the same time, sellers need to dig out opportunities that are not immediately obvious but lying just below the surface waiting for a skilled salesperson to uncover and close.



Remember these 3 strategies the next time you’re ready to pick up the phone, and you’ll be on your way to building a connection with your prospects and clients while creating a more open sales dialogue.


Editor’s Note: This post was originally published in March 2013 and has been updated.

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Topics: sales, tips, selling, sellers, prospecting, value, skills, sales tips, sales training, digital media training, cold calling, call, small business, improving, marketing, strategy, phone

How to Develop Competitive Sales Skills

Posted by Steve Bookbinder on Feb 9, 2017 4:22:00 PM

Developing competitive sales skills focuses on being prepared to perform under pressure, in any type of situation or environment.

Sales professionals who have competitive sales skills are the ones who think of sales in the same way professional athletes think of their jobs: with confidence about their own abilities and fear of their equally skilled competitors who may be better at using their abilities.

Confidence, born from focus, attention and ongoing skill development is the chief ingredient for success, no matter what industry you are in.

So, whether you’re training yourself, or your team, it can be challenging to determine specific areas of development that are important to focus on.

 That’s why, in addition to the insights shared by Steve Bookbinder in the video above, there are 4 important lessons that you must also focus on in order to gain a competitive advantage and own your success.

Approach big challenges differently than you do day-to-day challenges

Thinking about the future tends to cause our brains to minimize the obstacles we'll face and instead focus on desired outcomes. We look at goals differently based on whether they are a short-term or long-term goals. For instance, 3-months ago when you booked a trip home to see your family, you were focused on abstract ideas like “quality time with my family and friends” or “downtime.” But I would imagine when it came time to actually leave for your trip, you were more concerned about your immediate needs like: "what should I pack" or “how am I getting to the airport?” It is only when goals get closer and more immediate that people start to think about them more concretely. So, focus on making small, incremental lifestyle changes that may feel less glamorous, but will have a much greater chance of creating real change in your life.

Always be realistic about your starting point when facing a big challenge.

There is no advantage in exaggerating your abilities or skills; it’s more productive when you acknowledge areas in need of development and then set out to improve upon those areas in order to achieve your goals. Asking the right questions will help lead you down the right path. But that requires being honest with yourself, and not coming up with an unrealistic plan that you’re overwhelmed by, instead aim to take stop steps each day. And remember, play within your own abilities, and recognize constraints of your product, your company, and the marketplace.


Focus on identifying everything that can go wrong, rather than blindly trusting optimism.

While it is good to remain positive and confident that you will prevail, that is not the fuel that will help you prepare fully and give you the confidence you will need to overcome your biggest fears. Fear makes most people stop. But we can use our fear and feeling of being uncomfortable to propel us forward. Consider holding yourself accountable by involving a friend, co-worker, or partner to hold your feet to the fire. When we have support as well as keep pushing ourselves forward by stepping out of our comfort-zone, those are times that test our abilities and help us grow and gain a better understanding of our own work styles.

Don’t stop until you reach your goal.

The competitive sales professional will stop at nothing. They are driven, focused, and persistent.

Whatever you’re selling, you’ve got competition. Somebody besides you is selling to your clients and customers on a regular basis.  Assume that it’s a zero sum game, which means that if someone is getting “more”, then someone else is getting “less.” While we can’t control all of the factors involved in making a sale, we can certainly take all the right steps to properly prepare.

In a competitive situation like a playoff game or a race, every player wants to win at the start of the game --- the consistent winner isn’t the person who wants it bad enough at the starting line; it’s the person who was willing to prepare on all of the days leading up to the big game day!


Competitive salespeople beat their competitors as well as their own best records from previous years by focusing on all four of these lessons.

To develop your skills as a sales professional, you must work towards understanding yourself and equally as important, you need to understand your competition.

The best competitive sellers are willing to do whatever it takes and they ask themselves:

  • What are my competitors doing that I should be doing? Or shouldn’t be doing?
  • How many prospecting calls will they make?
  • How will they prepare for their sales meetings? Oh and by the way, these are sales meeting that are with the same type of people you want to meet with.
  • How will they handle objections?
  • How will they answer the tough question: “how are you different from your competitors?” How will they make their offering sound compelling and ROI+?
  • What are they doing to prepare for a successful year that includes beating you at your game?

Unless you consider these questions — even if the answers scare you — you will not as likely prevail like a competitive salesperson. So gather your confidence, skills, and go out there and conquer the sales world!

4 Steps for Improving Your Time Management and Sales Skills - Free eBook

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Topics: training, sales tips, sales training, goal setting, how to be your own coach, Investing in Sales Training, salespeople, high performing salespeople, sales tools, competitive selling, how to, confident, confidence

4 Steps to Take When Closing Your Next Deal

Posted by Steve Bookbinder on Feb 2, 2017 6:30:00 PM

Closing a deal is the ultimate reward for all of the research, preparation, and follow up that goes into building new relationships and maintaining a high level of client satisfaction.

Every now and then, it’s important to remind yourself to go back to the basics of selling to ensure that you’re not simply closing a deal, but instead, opening a new relationship that has future growth potential.

So, when the time is right and you’re ready to close your next deal, remember these four tips: 


(SLA) Service Level Agreement

SLA stands for Service Level Agreement; in other words this is the document that outlines the timing and delivery of the products and/or services you will provide. This is a critical point in the sale because this is where all expectations need to be set and understood by both sides.

When you close a deal, it’s not enough simply to get the sale. You want to be able to leverage the sale in the future. To do this, you need to confirm with the customer that he or she feels your level of service is superior and that you did more than simply meet the minimum requirement. So, when formulating your close, review what the minimum deal is and then determine what else you can add. Be sure that you have added in enough elements to your deal to get that agreement.  


Review a sale you are closing now or have just closed. Decide what you can add (product, service, conditions terms, etc.) to enhance the service level without increasing cost to you.

On-Boarding Process

Sales continue even after the close.  As the seller, you are the “face” of the sale to the customer. So, the customer will always look to you to explain and validate every step of the implementation even after the close. Therefore, meet with your internal team and carefully review who does what, when, why and how. Then, repeat the process with the customer explaining who on your team will be taking over the implementation on your side. Be sure to always point out the value of each person taking charge of the steps in the implementation. This builds rapport and helps pave the way for future sales.


Think of a current sale and review your on-boarding process for the account once you close the deal. Use a tool like the following to think through all the steps in on-boarding. This will help you be ready to both explain the process to the customer and to ensure the process goes smoothly.

Future Opportunities

A single sale for a single deal may have a finite point. However, the superior seller knows that each successful sale leads to another... and another…. You can leverage past success into future success by ensuring that the job you do with the first sale is not only adequate but superior, beyond expectations – in effect, stellar. This way, you develop equity within the account and draw upon that equity to pursue one successful sale after another.


Review a current or upcoming sale. Review the terms of the offering. Find something that will help the sale exceed expectations – something you or your company will do, a “deal sweetener,” etc…

Strategizing the Right Time to Ask for Additional Business

 A major goal of the consultative seller is to position him or herself as the “conduit” of a range of products and services that address multiple functions within the account. This process is called “evergreening.” To successfully evergreen an account, you have to be extremely observant to what you see and hear and what you can deduce to identify opportunities all the time. Then, when you spot an opportunity, you move on to that one if your present sale is going well. This way, the present sale “evergreens” into additional business.  Account selling is not linear.


Review all your active accounts. For each, think of additional opportunities and note how you think you can transition from your present deal to the future opportunity even before you close the first one. Use a tool like the one below for your analysis.


Before closing your next deal, take these four things into consideration and utilize them to your advantage by ensuring that you: set expecations up front, properly on-board new clients by clearly outlining how your product or service will be implemented, understand what a future opportunity might look like, and strategize the timing of asking your client for additional business.

How to ask for the deal without sounding too

Editor’s Note: This post was originally published in December 2013 and has been updated.

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Topics: sales, training, tips, managing, manager, client, cold calling, building client relationships, strategy, deal, service level agreement, client on-boarding

3 Tips to Help Managers Coach Sellers More Effectively

Posted by Digital Media Training on Jan 13, 2017 12:00:00 PM

Managing a sales team can be challenging.

Sales managers are responsible for a range of diverse tasks, including managing a sales pipeline, coaching their team, forecasting, hiring new sales representatives, strategic planning, and sales administration.

Additionally, managers are held accountable for hitting sales quotas and responsible for a target list of accounts. Not to mention dealing with a variety of independent and strong willed salespeople who establish their own process with little to no daily contact with their managers.

With all of this in mind, we want to help make your job easier, so here are three things to focus your seller’s attention on:



Every year, salespeople are presented with new challenges. The challenge of selling in a more competitive marketplace, hitting a higher quota or goal, and all the while gaining more responsibilities.

As a manager, your job is to enable your seller’s success through coaching and support.

The first step is helping your sellers identify what metrics they should be tracking.

For example, each rep should know how many:

  • Open opportunities are in their pipeline
  • Closed opportunities (both won and lost)
  • Average deal size
  • Average sales cycle length

Once you’ve determined the key performance indicators important to you and your team, then you can create a dashboard that tracks and measures progress against these metrics.

Your dashboard can be as simple as using the CRM you already have in place, or creating a separate spreadsheet to track everything outside of the CRM. Whatever you decide, make sure it’s a platform your team can easily and consistently update.

When you have an understanding and baseline of your performance, it’s much easier to reverse engineer what it will take to hit your new quota or goals.

The First Conversation

The first meeting or the first conversation with a prospect is a crucial point in the sales process. It can either make or break the deal, which is why it’s vital to your sales team’s success.

You need to help your sellers strategize the first meeting in terms of:

  • Have you done your research? What do you know about the company/industry/person your meeting with?
  • What’s the goal of the meeting? (from their perspective and from ours)
  • What is this prospect trying to accomplish?
  • What do we need to learn? (Budget, timing, authority, etc.) What questions to ask?
  • Does our solution fit their needs?
  • What’s our next steps?

When you encourage your sellers to prepare for and consider in advance what the first meeting will look like, your reps will increase their confidence and ability to start the right conversation that leads to having a great first meeting.

Is it Worth It?

As a manager, you need to help your sellers prioritize their time and understand the difference between opportunities worth pursuing vs. dead end leads. To do this, analyze and refine your qualifying criteria.

Qualifying is one of the most important conversations a salesperson can have with their prospect. This is where you learn whether the prospect is a good fit for your solution and if it makes sense to move forward together, or go your separate ways.

HubSpot has put together this comprehensive guide that will take you step-by-step through the fundamentals of qualification, five different frameworks you can use, how disqualification works, and conversational tip-offs to listen for.

As you work with your salespeople, help them establish a measurement mindset in order to track their progress, emphasize the importance of the first meeting, and finally, work with your team to assess and refine your qualifying questions and criteria in order to maximize time spent with the right opportunities.

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Editor’s Note: This post was originally published in January 2013 and has been updated for accuracy and comprehensiveness.

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Topics: sales, training, sales tips, managing, sales coaching

3 Ways to Polish Your Sales Performance with an End-of-the-Year Evaluation

Posted by Digital Media Training on Dec 29, 2016 2:45:00 PM

The end of a year can conjure up positive connotations of new goals and resolutions, but it can also trigger lots of deep introspection and regret.

In sales, if you’ve already hit your target or are about to - why should evaluating the past be necessary? If you know you’re going to miss the mark on this year, quarter, or month - why would you want to relive your failures?

While it might be easier to jump ahead and see the year coming to an end as a new start, it’s equally important to look back with a sharp eye on the last few months.

Taking objective inventory of how you got where you are today and how you’ll try to replicate, improve upon, or completely refocus in the future is critical to making the next year even better.

Pay close attention to these three things during your end-of-the-year evaluation to help polish and improve your sales performance next year.



Your Numbers

Regardless of whether the revenue goal is on track or not, there are a multitude of numbers/metrics you should be taking into consideration when evaluating your performance.

We sometimes think that if we make a change it will be evident almost instantaneously in our numbers, but sales is like a new workout regimen or a healthy diet - it takes time to see results. It also takes time to see set-backs.

Try this:

Pick two months to analyze. The first should be your worst month and the second should be your best.

How many first appointments did you have in each month? How many outreach emails did you send? How many phone calls did you make? How many proposals did you submit?

Look at those numbers in the months at hand or two leading up to each one.

What differences are apparent? Do you see a certain trend in previous months that affected your worst and best month?

Based on these numbers, determine what you would need to change in your processes or strategy to improve them.

Your Sales Stories

Sometimes we focus too much on anecdotes from our own experience. These make rare exceptions seem like the rule and they can ultimately impair us in future situations, but they are extremely valuable.

All sales usually seem unique, but there are many patterns that can be discerned when looking at the bigger picture. Looking at the larger story of your interaction with a lead (whether they closed or not) can provide you with valuable insight into what you led to them closing or walking away.

Try this:

Identify two particular sales - one that you thought wasn’t going to happen, but did and one that you were sure was going to close, but didn’t.

Do they have anything in common? What differentiated them? Look for what was in your control, but also recognize what was out of your hands. What can you learn to do differently next time?

Keep in mind that some things will always be out of your control, but it’s always important to debrief to strategy how you can better handle the situation in the future if it were to arise again.

Your Feedback

How many customer service surveys have you avoided taking? How about those regarding your performance?

Feedback is extremely valuable in providing otherwise missed insights and providing a base for improvement.

It can be daunting getting feedback since it can sometimes be looked at like criticism, but knowing how others perceive your actions will help you have a more objective view of yourself.

Try this:

Ask for feedback from your clients, manager, and moving forward - your prospects.

For those who bought from you, ask them what in your actions or presentation helped them make their decision.

For those who said “no” to your offer - ask them for candid feedback.  Their decision might have to do with your offering or it might be personal. Either way, knowing what it was that lost you the business will give you power for the future. You’ll be able to switch up your pitch and adjust your approach for the next prospect.

When it comes to your manager, set up a 30-minute meeting to see what feedback and insight they can provide. If you bring the numbers you should have analyzed by now, this can guide the meeting and help you both set a plan for the upcoming quarter.

Key Takeaway

It’s not always pleasant looking at ourselves with a critical eye. However, towards the end of the year, it’s necessary to take inventory of how we did and learn for the future.

Analyzing your numbers, stories, and getting feedback are the best ways to quickly determine what will make a difference in the coming year.

Take Client Relationships to the Next Level - Start Here

Editor’s Note: This post was originally published in December 2015 and has been updated.

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Topics: sales, sales coaching, sales performance review, sales performance, sales evaluation

What’s the Cost of NOT Training Your Salespeople?

Posted by Steve Bookbinder on Dec 15, 2016 2:05:00 PM

Well, let’s just say it’s costing you a lot more by NOT training your sales team.

You’ve probably all seen the endless statistics and reports about employee disengagement, unemployment rates, and the seemingly unrectifiable skills gap. Maybe you yourself are feeling disengaged or seeing too much turnover and not enough qualified individuals to fill open positions.  

Well, if you or your company have been putting off professional development and training for far too long, then it’s time for a change. Because realizing the importance of educating, coaching, and training employees and then actually implementing effective programs is the only way to achieve long term company success.

So why does your company need sales training? Consider asking these questions:

  1. If we raise the seller’s goals, do we expect them to hit their goals without improving skills, strategies, or tactics?
  1. If we haven’t hit the goals that our competitors have reached, what does that say about our previous forms of training?
  1. If your company invested in training last year but didn’t achieve the intended results, did anyone reinforce that training or was the expectation that the effect of training would be like a tattoo on each seller’s brain?
  1. If last year’s skills are the best we can hope for, what will that cost us this year?

While some sellers and managers may view sales training as “optional” or as a “luxury,” that thinking is short sighted and unrealistic. Simply “checking the box” on training won’t cut it anymore. If it actually worked, then everyone would do it that way.

Professional football teams would take the week off before a big game and then just sort of warm up before each game. Actors and actresses on Broadway would meet a few weeks before the show so the director could hand them the script and say “obviously you’re a professional, so you know how to perform the script. No need for rehearsal, see you opening night…”

But this doesn’t happen. And there’s a reason professionals make a habit of practicing and fine-tuning their skills.

When people are training all the time, they develop a "muscle memory" and get really good at processing information.  They become accustomed to finding something that resonates and then they are able to apply it to their daily activities. But when people rarely attend training, their skills fade and they struggle process and apply the training information.

Benefits of Sales Coaching and Training

Okay, so now that we’ve covered a few key considerations and reasons why you should invest in sales training, let’s look at some of the benefits:

Improved Performance

Employee education and training is designed to give your people the proficiency and tools they need to learn new skills and refresh old ones. It’s key in every industry to stay on top of new trends, timesaving technologies, and how to stay competitive. Providing training will make sure the entire team is fully competent and can help you set clear expectations with regards to new goals. Whether the company’s output is struggling or already doing a stellar job, training will only help to increase its performance further and deliver a great return on investment.

Higher Engagement

It’s no secret that unhappy, disengaged, and uninspired employees can eventually become less productive. Ensuring employee happiness with appropriate benefits and perks is only one part of the formula. Keeping them truly engaged by cultivating their specific skills further, as well as, providing education in the areas where they aim to improve, will increase their interest in their work and new projects.

Higher Retention Rates

Re-engaging employees through training and further education will improve their overall job performance and satisfaction. They’ll be less likely to let their eyes wander for other career opportunities since they’ve increased their skill level and hopefully intend to conquer new challenges. Investing in your company’s employees helps to show them their value, potential expertise, and the company’s focus on maintaining a long-term relationship with them. Having higher retention rates will decrease the huge costs often involved in employee turnover. Making the small additional effort to train your current employees will save your company the headache of later trying to replace them.

Cohesive Onboarding

If your company has been expanding and adding to its staff then you’re probably already familiar with the difficult task of getting new members up to speed. If not done properly, you may later experience many unforeseen problems and confusion. Thinking ahead and providing onboarding training to your newest employees will help eliminate future turbulence due to unclear expectations and potentially unfamiliar methods. It will also convey the company’s desire to engage with and improve upon the skills new workers bring to the table.

Elimination of the Skills Gap

Some companies are having trouble finding the right people to fill open positions. Closing the skills gap is something that your company can do with training. Whether there’s a current employee who has shown incredible potential and just needs some more knowledge to transition into the open position, or a prospective hire that’s promising if it wasn’t for their minor lack in a certain area, why shouldn’t you just train them? It’s unrealistic to believe that if you’ve already been waiting for months, that if you just wait a little bit longer, the perfect, ideal, absolutely spectacular candidate will come along. That’s not to say you should lower your standards, but accepting that you will most likely have to teach anyone coming into the role a thing or two, why should you contribute to the growth of the skills gap if you could just rectify the situation and start training?

Reduction of Skill Fade

Do you remember everything you’ve ever learned? Of course not. Even the most dedicated and skilled employees will eventually start losing grasp of things they learned decades, years, months, weeks, or even days before. Having regular training sessions or better yet - ongoing training - will help reduce the previously inescapable skill fade-out phenomenon. Reinforcing previously learned material will ensure employees are always current with their knowledge and continue to increase their performance.

What it comes down to is that sales organizations must redefine what training and learning means to them. Success in sales means being prepared, nimble, and continuously developing the right skills that will have a positive impact on the entire business.

What is your company’s biggest excuse for not training their employees? Is it too expensive to train them? Or is it a bigger expense if you DON’T train them?

The 12 Days of Selling - Free DMTraining eBook Offer

Editor’s Note: This post was originally published in January 2013 and has been updated for accuracy and comprehensiveness.

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Topics: sales, tips, sales training, managing, digital media training

Why Typical Sales Reports Don’t Work & What Report to Use Instead

Posted by Steve Bookbinder on Nov 17, 2016 4:40:00 PM

What’s the purpose of a sales activity report anyway?

Generally speaking, sales activity reports are meant to guide managers in tracking and understanding the productivity and progress of their sales team.

These reports enable managers to visualize how much time salespeople are spending on different sales activities, if they are meeting their productivity goals, and whether their efforts are translating into real sales.

But when your sales reps put together their report, are they really telling you an accurate story? If they are using a typical sales activity report, then don’t count on it and here’s why.

There are 3 reasons to avoid traditional activity reports and why you need to replace it with the 1 report that will truly paint a realistic sales picture.

sales activity report for managers

Motivation to Mislead

If I am a salesperson and I know that every week my boss is going to read my activity report, then I will end up writing a biased report for reasons that are intentional and unintentional.  Managers should consider this before asking their teams to submit activity reports. 

Intentional: Obviously, I would prefer that my boss concluded from my report that they should continue paying me and maybe even consider giving me a raise.  To the degree that I can persuade with a report, I will attempt to do so.  Often, I will use the quantity of activity as proof of how busy I am - and therefore doing my job!

Unintentional: If you believe that certain activities are valuable to your sales success (or you think your boss believes in those activities), then your weekly activity report to your boss will likely be biased by highlighting those activities.  Even if those activities can’t be linked to closing sales they will be described in a way that exaggerates their contribution to overall sales success.  Common activities like “following up” will be made to look like critical strategies instead of what it really is: calling people /sending emails to unengaged prospects who remained unengaged despite the activity of the salesperson.

Both forms of bias create a positive sounding but misleading picture of activity. And worse, all the activity is described as if happening in a vacuum; not influenced by current and forecasted sales. 

As a manager, I want to see my people choose activities that are specifically informed by the latest developments in their sales pipeline. 

Activity Reports Only Answer: Was There Activity? 

Even the most underperforming sales rep can usually boast of at least a little activity – usually exaggerating how long each “necessary” step took them to accomplish.  Most salespeople however, regardless of how badly they miss their goals, can make themselves very busy and their activity reports can mask real opportunities to improve. 

The activity report, which managers really want, is not an activity report at all. 

As a manager, I’m less concerned if my salespeople are busy and more concerned with making sure they are focused on the right sales coming in and delivering exceptional customer service. But what activities truly result in closing the right number of deals and maintaining customer satisfaction?

You could list every reasonable selling activity like prospecting, meeting preparation, customer service, you name it. The only activities managers really care about are the activities that will move the needle on sales for that week.

While understanding the gory details of various opportunities that didn’t progress through the sales process is important, that’s not the purpose of an activity report.

If your sellers are eager to give you a blow by blow account of their deals that didn’t close, then make sure you have that on your agenda for your next one-on-one coaching session. You can help each rep analyze their findings and then make recommendations for adjustments.

Activity Reports Glorify Activity

Glorifying activity just for the sake of it only confirms what underperforming reps think: as long as I show activity, I’m doing my job.

I beg to differ. While trying really hard is appreciated, it’s not effectively doing the job at hand. The job is selling, building relationships, adding value to the life of your buyer, and so much more.

As a manager, I’m interested in seeing the result of activity report. In other words, managers want to see what new sales are moving forward, are any existing clients up for renewal, and how much more will they be investing?

In fact, by looking at that report, I can more accurately determine what activities are necessary to optimize performance and scale results.

So, that brings us to the one report you need. But what would a “results-of-activity” report look like?

The Result-of-Activity Report

This reports identifies the activities that specifically contribute to sales in both the short term and long term. So, let’s take a look at the 4 kinds of activities that managers should want their salespeople to report on.

First Appointments

The first activity that managers should know about are First Appointments, that is:

  • New sales conversations with new leads
  • Restarted opportunities that were stalled
  • Existing account renewals
  • Account penetration sales

No matter how many types of activities a salesperson wants to describe in a conventional activity report, questions about first appointments get to the heart of the matter. And managers want to answer these questions:

  • How many new business conversations were scheduled?
  • How many were conducted?
  • Based on my (the sales rep’s) goals and YTD sales ratios, what is my target number of First Appointments?
  • Compared to last week, did I create more or fewer First Appointments?

As a manager, nothing makes me surer of future sales than First Appointments made this week. Why? Because First Appointments close at the end of your sales cycle. Therefore, if no First Appointments were conducted this week then we can’t forecast or expect to close any sales in the corresponding week at the end of the sales cycle.  

From a sales coaching and diagnostic stand point, do you know who needs more first appointments? Successful salespeople that just closed a deal as well as salespeople in a slump who need to make something happen. Only if a salesperson can continue to make First Appointments every week are they practicing effective time management principles. Because the definition of time management for salespeople is their ability to keep making first appointments even when they are busy.


The second activity that managers should know about is qualifying, and here’s what to consider:

  • What type of activity and how much effort went toward moving recent First Appointments forward and keeping them as viable prospects?
  • How many first sales conversations as well as ongoing sales conversations resulted in a scheduled next step?

These considerations reveal critical insight about a salesperson’s ability to engage, qualify, and strategize solutions with prospects.

The importance of activities within this category is the fact that some of these prospects will refill the other prospects that fall off or fall back. When you have a constant flow of leads, you can avoid the ups and downs of selling.

Questioning sellers about this category of activity will help managers identify if their reps are spending too much time, or too little time, working with prospects at this stage. Good things take time, so remember that time spent developing prospects is time well spent.

Expected Decisions

The third activity that managers should know about has to do with expected decisions.

The questions managers want salespeople to answer each week are:

  • How many total decisions are we now expecting?
  • What was the number of decisions expected last week? Has that number changed?
  • Are we waiting for the same decisions that we were waiting for last week?

As a manager, you need to know how many prospects have advanced to the decision point where we now know we can expect a yes or no decision within the next one to eight weeks. This will depends on your normal sales cycle and could be more or less than eight weeks.

Getting to this point in the sales cycle can be challenging. If sales reps are having trouble reaching this stage, then perhaps it’s time to rethink and reframe their activity. It can be as simple as making sure they are aligned with your qualifying criteria and how to identify the right decision maker, or it might take a more in-depth assessment of their selling skills and techniques.

Changes: Last Week vs. This Week

The fourth activity that salespeople should report on may be the only one a busy manager really needs to understand: What has changed since last week?

Managers want to know:

  • How many closes (contracts) are expected in the next 1-8 weeks?
  • What was that number last week? Has the number changed?
  • Are we waiting for the same number of contracts from the same prospects?

Every contract is either closer or further from closing or aging out. Either way, these pending opportunities need to be replaced before we lose them. We either lose a prospect because the deal closes, or because they don’t move forward with the deal.

For this reason, salespeople need to re-evaluate their list of prospects every week with an eye toward replacing those that are aging out with newly developed deals from this week’s activities.


The goal in sales is to produce. Since sales come from prospects, the real goal becomes building a path to the goal with the right prospects.  It’s this path and not the underlying activity that matters most to managers.  They know the longer a sale or prospect goes beyond the normal sales cycle, then the less likely they are to advance to the next sales stage. The best reports help the manager quickly determine how they can help their salespeople build a stronger path.

Traditional activity reports are like a good novel: entertaining reading about something the author just made up. So I encourage you to start getting real and keep track of the four key activities mentioned above to truly understand the performance of your sales team and how to help them improve.

The Manager's Guide to Increasing Sales through Existing Customers

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Topics: sales manager, sales activity, sales reports, sales performance