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1 of 10 Reasons Why Sales Reps & Their Managers Fail

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The big-picture

Perhaps a more appropriate title to this blog is "More Than 10 Reasons Why Salespeople Fail and Other Tales," but that would ruin all the fun I am going to have with the many blogs I plan on writing on this topic. I am just going to stick to one problem for now: Big-Picture Planning.

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The sales failure question has plagued CEOs, CFOs, sales leaders, marketing leaders, product leaders, individual contributors, investors, board members, and customers for eons. Thousands of books, training methodologies, technology platforms, consulting practices (including mine) and other sales improvement businesses have been developed trying to help companies and sales professionals solve this problem.  

Despite all the resources out there and the investments made in developing a world-class sales organization, I don't think I have had any sales leader or CEO tell me that they have a team with

90% of reps hitting quota consistently month over month or quarter over quarter?. I really haven't. Have you?

In fact, I hear the opposite. Anguished calls for help. Less than 50% of sales teams hitting quota. That's a miserable place to be.

The truth is, there are so many possible reasons behind sales failure -  including subpar sales skill levels, poor sales leadership, toxic company culture, corporate goal misalignment, poor product performance, inability to keep up with increasingly complex market demands, and market issues such as the economy - it's hard to know where to begin. While I have experienced some companies suffering from a multitude of these issues, thankfully, most companies only suffer from one or two.

My favorite place to begin is with the people, processes, and platforms that make up what I call The Revenue Room. When you focus on The Revenue Room, it allows you to go back to basics and start with people - individual sales contributors and their managers - and the most crucial activity behind hitting and exceeding target.

Mentoring bubble on black background

Big-Picture Planning is an effective and powerful coaching and mentoring platform for sales leaders. 


Not having a Big-Picture Plan strategy when it comes to sales - especially in today's environment, where top-notch sales organizations are training their people to be revenue machines - is, frankly, the kiss of death. It also tells me that the sales leader is simply a NEWB, as the kids say. Most sales reps think they have a plan and that plan is their quota. And to hit that quota, they are going to do two things:  close new business vis-a-vis the leads the SDR team delivers to them, and renew their current base. I don't know about you, but that seems like a very bad and risky plan, but it's one that most underperforming sales organizations are fostering. 

But let's talk about who has responsibility for creating a Big-Picture Plan.

The AE has some responsibility in creating the Big-Picture Plan, but I believe this is where the sales leader comes in and where a sales leader can be most powerful and effective. Creating the Big-Picture Plan is a huge and critical coaching activity that sets the stage for success and almost all future coaching throughout the sales year. It will also help the sales leader clearly separate the winners from the losers.

White puzzleBig-Picture Planning is the art of aligning your business goals - 100% quota attainment - with a sales rep's personal and professional goals and working together to achieve them. It separates the winners from the losers.


A Big-Picture Plan is not just about a quota - it's about a bigger life goal and all the activities that need to happen to reach it. Sales managers should sit down with each of their sales reps at the beginning of the annual sales cycle or during the first 30 to 60 days of a new hire and come up with a Big-Picture Plan. A Big-Picture Plan needs to be a measurable, agreed-upon, written-down, timelined-out plan that is reviewed on a consistent basis, with KPIs tied to each milestone and status update review meeting.  

Here's a sample Big-Picture Plan approach that you can work out with your sales team members:


What specific number does the rep have in her mind as to what she wants to earn this year? $150,000? $200,000, 250,000? More? Or, is there a major life event such as a wedding, honeymoon, baby, college tuition, house purchase, or other big expenditure that has to be paid for on top of regular living expenses? There may also be professional leaps the sales rep wants to make, or, the Top Performing Sales Person of the Year award. Whatever the motivation, there is a number attached. Map out what that number looks like and when the AE needs to arrive there. 


Once you map out the personal financial goal, work out how that maps to their current quota and commission rate. I am making a pretty good assumption that what they want to achieve will require at minimum hitting 100% of the quota you set for them. My hope is always that their personal goal will require them to overachieve the quota.

Sales reps and sales leaders who are not using a Qualified Pipeline X Factor approach when setting pipeline KPIs are missing the boat. 


When I hear that sales reps and sales leaders do not work using a Qualified Pipeline X Factor for each sales rep - and trust me - I have experienced this in about 75% or more of the places I have consulted with and worked for - I get a little red in the face. This metric is so critically important to ensuring quota attainment, and I am just baffled that so many sales leaders still have their jobs without focusing on this.

As a sales leader, you should know the conversion rate of your deal flow to closed/won. That's your X Factor. And frankly, you may be hitting quota without an X Factor strategy but what that tells me is that you are leaving money on the table and your sales reps are not working hard enough. 

But I digress.

Using the number the rep needs to hit in order to achieve their financial goals - which should be at or above quota - multiply that by your pipeline X factor. I always like to use 3X. If my target is 1,000,000, I need 3,000,000 in 25% or higher pipeline. "25% or higher" in my book is defined as:

  • Verbally qualified through discovery call
  • BANT and risks to close are known
  • Demo/sales pitch has been conducted
  • Prospect is actively moving through the pipeline

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Understand the various layers of your pipeline and map KPIs against each layer: New Business, Repeat/Upsell, Expand.


Now you know what your sales rep pipeline needs to look like, time to break it down.

  • Renewals: If your AE is responsible for renewals and new business, going through renewals first is the obvious first step. This is where things get a little tricky as salespeople are wildly attached to their renewals, take them for granted in terms of the ongoing selling that needs to occur, and are often very surprised when that renewal doesn't materialize. This means big trouble for forecasting and hitting quotas. I like to go through each renewal, pressure-test activity levels that have taken place with that account, identify any internal or external risks we may face and cut whatever we agree on as the percent likelihood of closing at LEAST in half. It's a painful exercise but one that most likely leads a much better than anticipated outcome if the forecasting is incorrect and the sales rep is not taking that renewal for granted in terms of the sales activities that need to take place. 
  • Expansion: Expansion sales typically work for sales reps who own enterprise accounts. While I allow for cross-selling - ie selling an extension of your current product to an existing buying center, to be lumped into the renewal category - breaking out the expansion part is critical. I define expansion as growing a footprint into different buying centers within the same organization OR selling a new product to existing customers. However you define it, separating expansion from product extension upselling (e.g., upgrade from gold to platinum, adding on a module) is that expansion takes a different level of effort, time and resources on the part of the sales rep. To define their expansion sales targets, review their enterprise account list (some folks call them key accounts), identify those with untapped buying centers, place a dollar target amount against each, then divide that target up by quarters or by half. 
  • New Business: Typically defined as a new logo, new business is a key KPI for your sales rep, for your sales floor, and for the company as a whole, and one that is much harder one to predict. You should set a realistic expectation as to the number of viable leads that will be generated by your inbound and outbound SDR teams because, as we all know, sales reps never receive enough leads from SDRs. Once you agree on what is a reasonable expectation, then discuss how the sales rep will fill the gap. Mediocre reps will fight you tooth and nail on this one. Top-notch sales reps will embrace the need to generate their own new business simply because a top-notch rep would never leave their financial fate in someone else's hands. Take time to go through how the sales rep will fill that gap in terms of lead identification, prospecting, and outbound calls each day. Or, if you have a sales organization where your outbound SDRs partner with your sales reps, ensure that the SDR and sales rep are aligned in terms of outbound activity levels so the sales rep can hit their NB target and are meeting on a weekly, if not daily basis to sync up on that day's outbound activities.

Risk spelt out on scrabble board

Having an insurance plan well in advance is always a sign of a pro and mitigates the risk of missing quota.


Now for the fun part. You and your sales rep know what their pipeline needs to look like in terms of composition; your next step is mapping out the activity levels required to get there. 

  • Activity Levels: How many calls, sales visits, demo's, proposals, and contracts does your sales rep need to conduct every day, week, and month? Provide an easy way for you and your sales rep to track and make these activity levels meaningful. For new business generation, will they schedule daily call blocks where they do nothing but call prospects to set up appointments? Activity levels are the number one thing to slip so it is essential that your sales rep doesn't get complacent. You will use the sales reps activity level tracking to coach through sales slumps as well as sales bonanzas.
  • Insurance Plan: What's the insurance plan if assumptions about renewal rates go south or if your sales rep's SDR partner suddenly exits? What about planned vacation impacting activity levels? A true sales leader and sales rep will identify any and all risks and gaps in hitting the Big Picture Plan and adjust the activity levels accordingly.  Your insurance plan may look like this: I know I need to have 3X in pipeline, I am going to shoot for 3.25X no later than early Q2 as insurance to offset any unknown risks or gaps I may face. 


​Once you have your plan mapped out in a way you can track and measure, schedule monthly 1:2:1 meetings to go over the plan, where they are based on the milestone KPIs you agreed on, and if they are falling short, first have your sales rep identify why they think they did not hit their KPI's and then coach them to a solution to recoup and regain steam.

Big-Picture Planning is a great tool that generates excitement, creates a personal "I can't fail" connection with hitting and exceeding quota, provides a platform for ongoing coaching, and keeps everyone accountable. It also will separate the winners from the losers at both the sales rep and sales leader levels. 

Please comment below or email me directly to let me know how you do Big-Picture Planning. 

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