Let's Chat | Call us: 212-502-3066

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

Read More

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

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

Read More

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

5 Sales Tools for Powerful Prospecting

Posted by Molly Depasquale on Apr 17, 2014 12:00:00 PM

Being a salesperson isn’t easy. We have to be charming, well-versed in our product or service, and extremely organized to do our jobs successfully. But how can we accomplish this? The right sales tools can go a long way toward increasing productivity and boosting the bottom line.

Here are 5 sales tools that can help you become more efficient when it comes to preparing for meetings, finding new leads, and managing current accounts.

1. Meeting Mapper


Say hello to Meeting Mapper. This iPad app makes meeting management and planning easier than ever. All sales opportunities and projects start and end with meetings. But, it’s the information that you capture in those meetings that determines whether or not you will win or lose the opportunity. Using Meeting Mapper allows you to capture notes (internal and external) as well as the role, stance and level of participation of all the meeting attendees and assign next steps or action items. What you do with this information is also very critical, using Meeting Mapper you can share this information to your team members via: Dropbox, Box, Evernote, and/or SalesForce.



2. PowerDialer


PowerDialer for Salesforce is a powerful collection of communication tools to call, contact, and sell more effectively. The easy-to-use interface takes lists of names directly from your CRM and plugs them in, eliminating the pain of manual dialing, then instantly moves to the next best call in your list at the click of a button. The software incorporates best practices and predictive analytics so your sales reps aren’t simply making more calls, but they are also calling the right people at the best times to double contact rates and increase sales. Features include one-click actions, such as calling, voice messaging, and emailing, as well as a log to track call, record, and daily metrics. After the sale, you can gain valuable insights with robust reports to learn what worked and what didn’t.


3. LinkedIn Sales Navigator


Put an end to your cold calling with sales prospecting through the power of social selling. LinkedIn Sales Navigator will help you find, engage and build your network. If you’re already using a free LinkedIn account as a business tool to look for jobs or stay connected with colleagues, you already know about the amazing reach and opportunities that exist in your collective network of contacts. As sales professionals, we know it can often feel like we are searching for a needle in a haystack when it comes to finding higher quality sales leads. With the help of LinkedIn Sales Navigator, building a better lead list just got a lot easier. By upgrading to a Sales Basic account for $19.99/month, you will be able to use Lead Builder and Premium Search filters to identify the right prospects quickly. You’ll know more about prospects before reaching out and you will be able to access the profile details of 3rd degree connections.


4. SalesLoft Prospector


SalesLoft Prospector is a Google Chrome extension that allows you to build prospect lists. You can build highly specific and targeted searches from anywhere on the web using this browser extension. Search for titles, industry, location, social network groups, and more. Utilize SalesLoft within social networks by grabbing data from public profiles, no matter your level of connection. Additionally, you can export your information to Excel or Google Spreadsheet as well as sync your data directly with Salesforce.com. This is another great tool for increasing your efficiency when prospecting for new leads.


5. Rapportive


Rapportive is a free Gmail add-on that provides contact information right in your inbox. As you can see in the screenshot below, you can automatically see a contact's picture, job title, location, and social media profiles. In your inbox view, you can even click on any of the social media links to be automatically directed to a contact's social profile. When you’re ready to start communicating with the sales leads you’ve gathered, Rapportive helps you visualize who exactly you’re talking to. It allows you to gather further context by looking at their social media profiles so that we can learn more about who they are and what they are interested in. This results in more personalized communication that leads to an increased response rate.


What sales tools are you using to make your prospecting efforts easier? Share your comments below!

Prospect Management: Learn How to Manage Your Sales Pipeline

Read More

Topics: sales, business, sales tools, sales prospecting tools, lead generation, iPad apps, business tools