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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

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.

seller_Vlog 1_cover.png

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

4 Negotiating Strategies to Make You a More Efficient Negotiator

Posted by Steve Bookbinder on Sep 14, 2016 8:27:00 AM

Are you an efficient sales negotiator? If your proposals and your contracts are always the same number, then you’ve reached 100% efficiency. But that could also mean you are leaving money on the table, which is why the customer may have been so quick to accept.

When a sale gets to the point of negotiations, there’s usually a lot of discussion and debate around the elements included in the proposal as well as the total price, which is why sellers commonly lose value between the proposal and contract stages.

If you’ve ever been in that type of situation, here are four strategies to help you avoid losing value in order to reach 100% negotiating efficiency.

Negotiating Efficiency

1. Pick the Right Starting Point

How do you typically begin negotiation conversations? Do you offer to talk first? Or do you try to get the other party to talk first?

When we think about negotiation meetings, most customers are playing the same game about deciding who should begin the conversation. Why? Because picking the right starting point sets the conversational tone for the entire meeting.

A lot of sellers may start with a question like: “Do you have any questions about the proposal I sent in advance of our meeting?” Ideally, the customer says “Everything in the proposal looks great, we are ready! Where do I sign?”

If only making a sale could be that easy! Unfortunately, it doesn’t always happen that way.

In a dramatic example of a powerful starting point, a recent negotiation began with the one party telling the other “…you know, I was going to cancel this meeting because I am not sure we’ll be able to come to an agreement.” That changes the meeting in a hurry and focuses both parties on identifying and, if possible, jointly solving the problem that will prevent the deal from happening. The first thing it does is get to the all-important reaction that will tell you whether the other side is truly interested. It gives them the out they need to quickly and politely back out of the deal if that is their inclination anyway. But, by agreeing to continue talking they are demonstrating a willingness to find a win-win.

If you want to be a smart negotiator, then you’ll consider the right starting point as well as the risk and reward of every outcome in advance of the meeting. The exercise of visualizing each likely scenario will help you operate from a position of strength.

2. Have Two Potential Buyers

In almost every sale, there is an element of limited resources.  

For example, in advertising there is limited inventory. In finance, there are limited number of hours you can book your analysts to talk to your customers. In software, there are limited number of installation-service teams or available training dates.

When limits are introduced, there is a new-found sense of urgency. Especially if there are two customers who want the same limited resource. I used this strategy to sell my house, when the market was down, in one week. By setting the right price, I received two offers on the first day of listing the house.

If I received only one offer, then the buyer has the upper hand. However, the power returns to the seller when they are “caught in the middle” between two potential buyers. All of a sudden, a typical buying process has been turned into a competition with an increased sense of urgency for both parties to try to “win the auction.”

3. Include Something to Remove

When two people or parties are negotiating, the sound of their conversation has a familiar ring. You can tell they are seriously negotiating when one party announces, “what if we take away this piece in exchange for an earlier start date?” This signals that one party is ready to make a commitment; they’re serious about finding a win-win solution.

The person who makes this suggestion is usually the one who is in control. They are being proactive. It's much better to boldly offer to remove something that is potentially a problem then it is to wait for the customer to ask you to remove it. If they ask and you cave in, then you look weak. If you suggest it first, you look strong and observant.

People who negotiate against themselves strip down the offer so much they never leave enough to spare for this strategy. To give yourself a negotiating edge, make sure you include “excludes.”

4. Sell the Dream, but Move Forward on Phase 1

Most salespeople try to sell the customer the biggest possible deal they can. The result? It takes for-ev-er to close.

When we expand the deal, especially the budget, we are making the consideration process longer and more complex. The odds of closing the sale is now reduced and the seller’s available time to prospect is gone. The result is no sale now or in the future. But, every so often, a huge sale comes in. And that is the validation needed for most sellers to continue swimming in this circle.

I, however, have found more value in closing the sale faster over getting the most money you can. Now, that doesn’t mean I happily leave money on the table. It means I am more interested in simplifying the buying process for the customer – and myself.  I want the sale to close faster and be worth more over time.

My strategy is to whet the buyer’s appetite about the future upside we can potentially deliver to that customer – over time. I then get on the customer’s side when we discuss budget where I ask them how they would rationalize spending that much money on that service. From that conversation, we discuss ROI benchmarks, sometimes aggressive ones. I maintain that we can achieve those results – over time.  Now that I know the benchmarks they will use for the “big” sale, I offer to scale the whole deal down to a much smaller budget, which I call phase 1. While phase 2 has hard goals against a big budget, phase 1 is a test with easier benchmarks that will serve as “proof of concept” supporting the decision to go to phase 2.  The entire time I am delivering phase 1, I am talking with them about examining performance, benchmarks, and how to optimze in phase 2.  This can be an effective strategy for Account Managers, but especially good for Hunters.  

Remember: it is much easier for the customer to go from spending $1 to $2 than it is go from $0 to $1.  First get the dollar, then grow the relationship.

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Topics: how to negotiate, sales tips, negotiating

4 Salesforce Mistakes Your Sales Team is Making and How to Fix Them

Posted by Steve Bookbinder on Aug 31, 2016 10:10:00 AM

As the lead trainer for DM Training, I work with sales teams across the globe and across a variety of industries. Here is some news from the front lines:

Today’s sales teams are making 4 preventable administrative mistakes that are costing them money and time.

Most of my clients use Salesforce as their CRM, which they have customized for their needs. Plus they have adopted workflows and business rules all intended to ensure a rich database of information that could benefit both the seller and sales management.

However, sellers are not doing the administrative part of their job right and the ripple effect is causing inaccurate forecasts, frustrated salespeople who are not closing enough deals, and managers without the right data to know how to properly coach their team.

Salesforce CRM

As a sales manager it’s time to take charge and get rid of those errors. Look to see if your sellers are….

1. Not converting leads into an opportunity or a first appointment

Leads should be converted into an opportunity or a first appointment the moment they are qualified or that meeting is scheduled. It’s not something that should be done after the fact.

Sellers often skip this crucial step until the opportunity is further advanced, presumably to save admin work until they are sure there is a real opportunity.

Here’s the problem: not properly tracking scheduled first appointments denies the seller and you as their manager from easily seeing critical CRM-generated answers to 3 questions essential to diagnosing sales behavior:

  • How many first appointments does this salesperson schedule per week/month (on average)?
  • How many first appointments do they have over the next few weeks?
  • How many first appointments should they schedule, given their personal first appointment to closed/won ratio?

Without knowing the answers to these questions, how does anyone know how many leads the salesperson needs to generate and how much time should they allocate everyday toward making new first appointments?

2. Not making a new opportunity for every new opportunity

Regardless of whether an opportunity begins with a scheduled first appointment or not, it needs to be logged in the CRM immediately.

When your sellers do this reliably, you can determine the actual sales cycle of closed/won sales because there will be an accurate “start date” stamp on every opportunity. Comparing every new sales opportunity to closed/won sales cycles is the most accurate way to bet on a winner and avoid projecting the wrong (long) sales.  

3. Putting tasks in the opportunity screen, rather than the account screen

Because of this seemingly innocent workflow choice, the seller will be less reluctant to kill the opportunity (that is, convert to closed/lost) both administratively and mentally, because they are afraid of losing the task notification.

That opportunity will remain open even as the opportunity ages out and is no longer following the closing pattern. The opportunity cost of spending and wasting time with those prospects is not spending enough time pursuing candidates which are statistically more likely to close.

4. Not parking stalled sales in a column reserved for stalled opportunities

Simply putting a prospect in a column doesn’t change the odds of closing that sale. But keeping prospects in a funnel intended for advancing prospects is misleading.

When a sale stalls it is no longer predictable. It may close later than you think, or not at all. If the salesperson is unable to control the timing then forecasting is impossible.

From the point of view of collecting data which will give insight into the most likely to close opportunities, it is smarter to convert stalled sales to closed/lost or move them to a column specifically designated for stalled opportunities. If and when they restart, your sellers can return them into the pipeline.

Don’t assume your salespeople are using Salesforce to everyone’s advantage. Help them make these 4 tweaks to put you all in a better position.

How to Solve 5 Common Problems in Your Sales Team - Free eBook

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Topics: sales tips, CRM, common sales mistakes

How to Use Deadlines to Achieve Sales Goals

Posted by Steve Bookbinder on Aug 22, 2016 8:25:00 AM

Deadlines. It’s a powerful word that strongly suggests we must meet the time limit that’s been set, otherwise we’re dead if we miss it.

Most people have a love-hate relationship with deadlines. In most cases, deadlines are set for us by other people and can make us do crazy things. Things we don’t normally want to do like: get up extra early, work outside our comfort zone, or stay up extra late. All because we have to meet the deadline.

The ironic thing is that nothing provides more focus on our priorities and time management skills better than setting a deadline. We are usually at our best when we are racing to meet the timeline that’s been set because we are determined and focused on completing the assignment or project at hand.

With this in mind, imagine what we could accomplish by not waiting for someone else to assign a deadline, and instead give ourselves deadlines for everything we need to get done. But how do you assign yourself a deadline that will actually stick?

We’ve outlined 3 simple, but not easy, steps to help you use deadlines to achieve your sales goals:


Step 1: Commit

The first thing you must do is identify your goal and then commit to achieving it by a certain date.

Whether we are talking about a big or small goal, the best way to fully commit is by breaking down your goal into smaller steps that you can work on each day or week.

As a general example, let’s say you’ve just set yourself the goal of landing a new account with a large revenue opportunity.

In your experience as a seller, you understand there are a lot of internal and external factors that must be taken into consideration when mapping out your goal. And depending on your process and sales cycle, closing a large deal may take anywhere from a few months to a year.

That’s why we must break the larger goal down into smaller goals by creating a backwards timetable, like this:


When you look at your goal this way, it helps you think about what sales meetings need to be scheduled and what activities you should focus on during the months leading up to your target close date.

Let’s break this down:

If you need to close a sale in August of next year, then you need the verbal agreement by Q2, let’s say June.

Before that, you need to present a proposal that outlines the right solution for the client. Keep in mind this is the time when negotiations may happen, which could possibly delay this step. But on average, let’s say this will take about 1 to 3 months.

Now, that brings us backwards to Q4 of this year when you want the prospective client to express their interest, timetable, and confirm they have a budget for your product or service.

Even before the prospective client can express interest, we must get a better understanding of their business goals and challenges by launching a discovery process to gather more information. That will take about 1 to 3 months.

Naturally, we had to have a number of first meetings and conversations with a variety of stakeholders throughout the organization before we could get to the discovery phase. And depending upon the number of decision-makers involved, getting these meetings scheduled could span anywhere from a few weeks to a few months.

That brings us to now. It all starts with your outreach efforts and making the first contact. So, when is your deadline to get started? Today!  

Get committed and start thinking about: What do I have to do to make sure I hit the goal?

Step 2: Be Realistic & Honest

When it comes to setting and achieving an audacious goal, it’s important to consider timing.

Be realistic about your process and sales cycle in terms of knowing how long each part of the sale will actually take. If you started today, how long would it take to secure a qualified first appointment with a large sized account? And then once you’ve conducted the first appointment, how long after that would you get to the proposal stage?

Be honest with yourself about your time and priorities. Are you already working on a long-term project that requires a lot of your attention? Do you have anything going on in your personal life that could interfere?

More often than not, everything takes longer than initially anticipated due to the inevitable “things” creeping up and stealing your time. However, it's amazing to see how much harder people work when they are running out of time, as opposed to when they have plenty of hours to burn.

This is why the most successful salespeople set deadlines for themselves. It creates a sense of urgency and helps push you forward to completion.  Deadlines create determination and focus while discouraging you from delaying steps or becoming sidetracked on something else.

Step 3: Use the Power of Negative Thinking

Yes, you read that right. The power of negative thinking.

The idea here is that when things go well we seldom assess or analyze how we achieved the end result. On the other hand, when things go badly we suddenly have 20-20 insight into what we should have done.

Thinking about what might go badly, while you still have time to do something to change the outcome, will help you create a solid action plan outlining the right activities and behaviors to focus on.

So, leverage negative thinking by imagining it is August of next year and you missed your goal and didn’t close that big sale. What should we have done?

You should have filled your pipeline with similar opportunities. When you create parallel initiatives with several other potentially large deals, you put yourself in a much better position to reach your goal.

Remember, today is the last day to get that big sale you want to close next year. Today is your deadline. Don’t miss it, or you will push out the close date – possibly to 2018 unless you hurry. So now is the time to get committed, be realistic and honest with yourself about timing, and use the power of negative thinking to ensure you reach your goal.

Tune-Up Your Sales with Steve


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Topics: deadlines, sales tips, goal setting

4 Tips to Help Your Team Build Sales Momentum

Posted by Steve Bookbinder on Aug 10, 2016 8:40:00 AM

Being a sales manager can be incredibly frustrating or extremely rewarding, depending on how the wind is blowing. To make sure your team is continuously headed in the right direction you need to put the wind in their sails by helping them build sales momentum.

Sail on a boat

Here are 4 ways you can talk to your salespeople about building and maintaining momentum:

1. Keep Score

When salespeople get to more leads, calls, emails, etc., they meet more people, learn how to optimize their approach more quickly, and end up making more sales, more often. However, most sellers miss their goals and many never even move in the right direction.


They spend too much time doing the wrong things. To consistently get the right things done they should begin by simply trying to get more things done.

You’ll need to carefully track the most critical activities that move the needle for your team: prospecting outreaches, customers spoken to, proposals sent, contracts out the door, etc. Then create a scorecard with a daily activity score to reflect the subactions within those categories and establish minimum daily standards.

Tell your team: The day can’t end until you take these actions, get these results, and get this score! You’ll help your team get to more things when you use this different kind of time management system.

2. Future Me

Make sure your team spends time each day helping the future version of themselves.

How many sales will that seller need to close each month/quarter? In order to consistently hit the goal they’ll need 3 kinds of sales to close on a regular basis:

  • the big sale,
  • the existing customer upsell,
  • and everyone’s favorite sale: (the ironically named) easy sale.

The third kind of sale is really easy - at the end. That’s the part where the customer contacts your company! The part before that is the hard part. That’s when the seller is doing personal marketing, combining social media, email marketing, phone prospecting, and networking.

Are your sellers managing their time to fit personal marketing into every day? To do this right they need to consider these questions:

  • Who am I trying to reach?
  • What are they thinking about right now?
  • When they want to know something that’ll make their job, department, or company better, where do they go online?
  • Who do they talk with?
  • Who do they listen to?
  • What platforms, sites, blogs, or videos do they and their peers engage with?
  • How many inbound leads will future me need each week?

Before your team can personalize their personal marketing plans they need to make sure they are asking the right questions. It can take a year or more for some of those actions to percolate into inbound leads. Don’t regret not having your team start today.

3. Speed Dating

Nothing builds momentum like first appointments.

Psychologically the first appointment is a new chance to get things right, to find the right customer, to ask the right questions, and present in the best light. Arithmetically, more first appointments means more sales. Strategically, first appointments minimize the danger of getting too busy with unqualified prospects because having lots of first appointments forces the seller to get right to the qualifying questions.

So what can your team focus on to determine whether a prospect is qualified? It’s not that person’s need or budget, but rather their ability to make a buying decision soon.

Without enough appointments to sift through, your sellers will be tempted to promise everyone they meet a proposal. However, with enough appointments they’ll learn to qualify better and spend time with the right people while nurturing – rather than hounding, stalking, and wasting time with all the others.

4. Crazy Busy

Encourage your salespeople to get a CLEW by being crazy busy, without going crazy.

For me personally, this was the breakthrough. I realized that I need to get to 4 things everyday:

  • Critical things: a prioritized “to-do” list
  • Learning: things that have to be read or watched and understood
  • Exercise: physical activity to get the extra energy needed to maintain a faster pace and help problem solve
  • Writing: things that have to be written

Put it all together and it spells CLEW (pronounced CLUE), which is the report I look at every day.

Your sellers need to focus on the critical things, such as prospecting and administration. They should also continuously be learning more about the industry, what information prospects are looking for, news from your marketing team, and evaluating their own past sales efforts. Writing will help them improve their outreach and credibility in the industry. Set an example by keeping yourself accountable for these tasks as well.

When you share these 4 concepts with your salespeople you will see tangible results. If they try to adopt these principles---or they ignore them – either way, you will know right away. Make sure your entire team adopts them and puts wind in their sails (sales).

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Topics: sales tips, sales management