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

Get a CLEW: The Daily Activity Dashboard You Need to Organize Yourself for Success

Posted by Steve Bookbinder on Sep 30, 2016 3:15:00 PM

No disrespect intended, but based on my personal observations, few salespeople are organized, and even the organized ones are seldom organized around the task of being successful.  This level of organization not only keeps you pointed in the right direction but has an empowering effect that will give you the confidence you need to tackle and overcome the challenges in your competitive marketplace.  

Let me be clear: in today’s world, there are tons of tools that will help sellers get organized from a “file stuff perspective” – from CRMs, Marketing databases, SFAs (Sales Force Automation tools), Dropbox, OneDrive (and other cloud-hosted solutions) to Post-it notes.  So, the problem of filing is solved but the real challenge is finding what you’ve filed.

Consider a busy salesperson who is always on the move using many different devices and typically only has a minute to find what they are looking for.

You’ll need to consider how you will file these documents so that it’s easier to locate when you’re in crunch time. That will save you tons of time and reduce stress levels. But, to be successful in sales, we need another layer of being organized. And that’s when you are organized around the task of being successful. But how?  

Here is my 4-part daily system to get on track, stay on track, and position yourself for long term sales success.


Create a Daily Dashboard

The name I use for my own Daily Dashboard is “GET A CLEW” (pronounced CLUE), which is really an inside joke to myself about giving myself a clue everyday as to what I need to prioritize in order to achieve my goals.

CLEW stands for Critical, Learning, Exercise, and Writing; and the “GET A” is an acronym that stands for Goals, Expectations, Timetable and Accountable – I will explain the significance of this below.  

OK, maybe you’re thinking: “Wait! If I’m not organized already, how will adding a new dashboard going to help me? That will just add yet another distraction and dashboard to maintain.” I used to think the same thing until I realized the consequences of skipping this step. Let me explain.

Have you ever made a New Year’s resolution only to completely forget it by mid-January? Have you ever felt like you’ve been making the same resolution year after year? I call that swimming in circles.

The main reason you didn’t accomplish your goals is because you took your eyes off them.  You forgot to focus on them, you forgot to apply the big picture goals of your life to your daily activity choices. Instead, you reverted to old habits and patterns, which as we learn every year, brings us back to our original starting point.  

My CLEW report helps remind me of my business, family, and personal goals every morning before I start my day.

I begin each day by opening my CLEW report and re-reading my goals, which are broken down into short term and long term goals for business, family, and personal. This also gives me an opportunity to assess and refine when needed. The more specific your goals are, the more likely you will accomplish them.

Each morning, I’m able to re-commit to my own Goals by reviewing Expectations of myself, my Timetable (for example: deadlines, benchmarks, and time management choices such as ending the day with one more call or email to a prospect you’re working on), and finally, my report is a daily reminder of how I need to remain Accountable for my own success and happiness.

Get into the habit of looking at this dashboard every day, even if you’re just starting with the “GET A” part first, it will point you in the right direction and set your day up for success.

Now, let’s dive in to see how we can fully “GET A CLEW.”

C = Critical

Once you’ve completed the “GET A” part to starting your day, it’s time to mentally and emotionally prepare yourself for the first big task of each day:  aligning goals with daily activity.  

Making a “to-do” list sounds fine but by definition is merely a list, and is typically not prioritized or scored by importance. This results in unimportant tasks mixing in with activities that are crucial for achieving your goals. That’s why I look at my Critical list of items to get done, which are arranged 1 through 10 for both my personal and professional tasks. 

Every morning I cross off items done yesterday and re-prioritize the remaining items on my 1-10 scale. What a great feeling it is to re-examine my tasks every day to double check that I’m not missing anything and I’m working on the most important tasks to push me closer to my goals.

From a psychological point of view, it’s the little things that provide the greatest sense of satisfaction and empowerment: crossing items off and then adding new items to the list.

Remember that despite your level of organization, in sales there will always be more to do than time to do it. Each day you will not get to some things. Make sure you always get to the things Critical to achieving your long and short term goals by toggling between Critical and your calendar to make sure you have an appointment with yourself to do the most important things.

L = Leads and Learning

I’ve grouped these two things together because they are related.

First, if a salesperson is not spending at least a little time each day upskilling themselves about the latest trends impacting their industry, then they are falling behind.  Reading industry publications including comments on discussion groups and white papers is now a necessity – if only because we have to assume that both the customer and your competitors are reading – and interested – in learning more. 

Staying up-to-date works to your advantage in two ways: you’ll be the one informing your customers and prospects about the most recent or upcoming trends, and you’ll find new leads and opportunities in the process. An added bonus is that while gathering information you’ll gain greater insight into how to communicate the value of your offering.

So, to be organized around the task of learning, I work on learning in my off-hours. And rather than lose precious time deciding what to read I make a list of topics that I am interested in reading for both business and pleasure. Then, during my more relaxed times or in the early morning while transitioning from my first cup of coffee to my second cup, I review that list and select what’s on top. My goal is to “pleasure” read for an hour a day and “work” at least an hour a day. 

Learning is like exercise. Always a great idea, just not at this moment.  Everything in your day will pop up just in time to block you from getting to this important reading. So what’s the key to following through? Schedule time in your calendar, and stick to it!

E = Exercise

Regardless of your feelings about exercise, physical activity should be part of your everyday routine, even if it’s as simple as taking a walk around the block. Aside from the long list of health benefits, nothing will give you more of a mental boost than exercising.

In my case, I will think of the problem I’m working on and then I’ll swim for 30-60 minutes. When I get out of the pool, I come away with ideas to solve the problem. And you know what, every swimmer or runner tells me the same thing. Exercise an outlet. Are you using it to the fullest? Tell us what you think and your response may be included in an upcoming blog.

When I look at the Exercise section of my daily dashboard, I always remind myself of why I am exercising and what areas am I looking to improve? Reviewing what and why will help you stay committed to scheduling time on your calendar to exercise. A best practice of busy professionals is to exercise first thing in the morning because it helps fully energize and empower you to tackle the Critical tasks of the day.

W = Writing

While learning and reading are essential, writing is another piece of the puzzle that engages parts of your brain that push you to think harder and smarter.

In today’s world, sellers need to deliver impactful answers and examples to leave a lasting impression.  You need to reassure your prospects and customers with success stories while explain new offerings to people who may know more than you or less than you.  That’s why writing is a critical activity that will help you compile your thoughts, questions, and answers as you prepare for important meetings.

Spend time writing every day. What should you write?  Start by writing down your most common objections and then try turning-around each objection. Answer those hard questions like: What makes your solution different? Why is it better than the competition? How is it worth the money?

Assuming your improvisational skills will suffice is a dangerous bet – especially if your competitors are following my advice and staying organized around the task of beating you. And while spending the time working out the wording on “paper” may be painful, it will result in a more prepared and well thought out response, which leads to you sounding perfect when the sale is ultimately dependent on your answer.

So if you’re looking to gain a competitive advantage and not sure where to start, “GET A CLEW” will provide the framework to help you become more organized and create a daily routine that sets you up for success.

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Topics: sales, time management, organization

Time Management Tips - How to Get Things Done

Posted by Anna Adamczyk on Jul 23, 2014 9:05:17 AM

It almost always seems like 24 hours in a day isn’t enough and we’re constantly wishing we had more time. We’re lucky to have technology that can speed up a lot of our work, but unfortunately it can also be a great distraction. If you’ve been struggling to get things done and want to manage your time working more efficiently then read on...

Before we begin - Take a moment to ask yourself these questions:

When do I feel most productive? - Is it first thing in the morning? Or later in the evening? Do I prefer silence or does background noise help me focus?

Once you’ve figured out the answers to these questions you’ll hopefully know exactly when and where you feel most comfortable working and can create a suitable environment.

Now it’s time to get started -

Create a list.

Planning out what needs to get done is a great way to keep yourself in check and remember every task that is just on the horizon. How you want to go about it is up to you - it might end up being a daily or weekly list based on the amount of activities that will need to be done. Creating separate lists for work related and personal items is also a good idea. Keeping them in one notebook, in an app on your smartphone, or simply even on sticky notes can help you stay on top of everything you have going on.


Being aware of what order things should be done in is a crucial component of being effective, since not every task has the same importance and time constraints attached to it. Knowing what to start on first and how much time to allot is imperative. Grouping similar tasks together can also help you get organized and create a kind of flow to your day.

Get it done early.

Start those “looming” items as early as possible. Commit to getting a small piece done each day, even if it’s just for 15 minutes. It’ll add up quickly and later you’ll be grateful you weren’t scrambling at the last moment. If other people are involved in a project, reach out to them as early as possible to get the ball rolling. Tackling a task as a group is generally much more complicated because it involves coordinating multiple schedules, as well as, trusting others and yourself to stick to the plan. Getting everything done early will save everyone unexpected unpleasantries towards the deadline.

Block out distractions.

Here’s a secret: multitasking doesn’t really exist. When sitting down to work, make that your top priority. Turn off email notifications and close any tabs in your browser that you know you won’t be able to resist and aren’t relevant to the task at hand. Make those around you aware that you’re occupied and shouldn’t be disturbed. Constant interruptions no matter how short can quickly add up and prevent you from finishing anything.

Take breaks.

If you feel your focus fading while working, take a short break. Get away from your desk for a few minutes and turn your attention towards something else entirely. Hopefully when you get back to the task at hand, you’ll feel more refreshed and ready to dive back in. However, be careful to gauge your breaks and not make them too long or you might find it even more difficult to restart.

Make it a habit.

By continuing to adjust your work methods and keeping the listed tips in mind, you should be able to quickly make it a habit to work more efficiently and effectively. Those around you will also start to change their behavior once they know your patterns and everything should start running much more smoothly.

Don’t stress.

No matter how much you have piled on to your plate, remember, don’t stress. If you start working more productively, you’ll constantly be chipping away at what needs to be done and it will be manageable.

Unfortunately we can’t add more hours to a day, but we can change our habits and begin managing our time effectively to start getting things done.

What is your best time management tip? Are there any must have apps that help you organize your time?

4 Steps for Improving Your Time Management & Sales Skills - Download eBook Now

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Topics: time management