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3 Tips to Help Managers Coach Sellers More Effectively

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

Managing a sales team can be challenging.

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

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

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



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

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

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

For example, each rep should know how many:

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

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

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

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

The First Conversation

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

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

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

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

Is it Worth It?

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

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

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

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

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

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

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

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

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

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

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

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

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



Your Numbers

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

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

Try this:

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

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

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

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

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

Your Sales Stories

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

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

Try this:

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

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

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

Your Feedback

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

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

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

Try this:

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

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

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

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

Key Takeaway

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

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

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

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

3 Types of Sellers Who Need Coaching

Posted by Steve Bookbinder on Oct 5, 2016 11:46:29 AM

Coaching salespeople, like most things in life, does not favor a one-size-fits-all approach. 

In theory, all salespeople are motivated by money. But when it comes to motivating and coaching sales reps into action, it’s slightly more complicated.

If you’re a manager, then you’re already well aware that each seller on your team has their own unique personality and quirks, which can be challenging when it comes to managing and coaching these individuals.

Your goal as a manager is to build purposeful relationships that matter to your team so you better understand who they are, what drives them, and then find creative ways to help everyone feel personally motivated to succeed.

But, how do we properly coach to the most challenging types of salespeople?  

We’ve uncovered three of the most common types of sellers who may resist coaching, but who need it the most: The Defensive seller, the Yes-You-to-Death seller, and the Poisonous seller.


Type #1: Defensive

You may already know the type.

You bring them into your office to talk about their prospecting, specifically their lack of consistent prospecting. And they immediately fire back with: “I don’t agree, just yesterday I called 20 people.”

To which you add “yes, but last month….” They cut you off with “last month I was busy closing that big sale –which would you rather I did, close or prospect?” 

My bald head is actually the result of yanking out all of my hair while having these kinds of conversations.

To solve this challenge, you first need to understand how this kind of person thinks.  They are convinced they are always right and feel under attack if anyone questions their decisions.

In this situation, the coach needs to move to the same side of the table as the seller, both figuratively and literally.  Direct the seller’s attention to the facts, ideally on a screen or piece of paper. Point out the data that led you to the conclusion that the seller’s problem is they are not prospecting enough.  

For instance, a manager once asked me to coach an extreme case of the defensive salesperson. This rep was consistently missing their goal and wasn’t open to getting advice. The manager and I walked into their office where the seller was waiting for the meeting to begin.  Their body language strongly suggested they were closed off and ready to attack.  Instead of sitting in the manager’s seat across the desk from this seller, I sat alongside the seller. Together, we looked at their pipeline. I asked them “If you were the manager and I was the seller and this was my pipeline what would you tell me?”  Even though they were trying to be defensive they couldn’t resist their overriding urge to be right – in this case, right about how clever they are at correctly diagnosing a pipeline that hardly had any prospects.  They told me “I would tell you to prospect more.” Bingo!

If you don’t start from the right point, there is no reason in having a coaching conversation. In the example above, I was able to reframe the situation because I knew what type of person I was dealing with and it allowed me to select a starting point that would ultimately lead to a more productive conversation.

Type #2: Yes-You-To-Death

While these people aren’t as infuriating as the Defensive type of salesperson, they are frequently underperforming. They always appear to be on the verge of success, but can never seem to win despite their willingness to do everything that is asked of them. That’s the curse. 

These types of people can be great to have around because they are so willing to help, but it becomes a hindrance when they don’t have a good handle on their capacity. Saying “yes” too quickly can lead to confusion about expectations and results.

While it’s important to keep the positive spirit alive, you must pay close attention to everything they do in order to make sure they fully understand what’s being asked of them.

For instance, I once had a “yes-you-to-death” seller who agreed to use a specific negotiation strategy. While at the moment it appeared they understood exactly what to do, it became clear they didn’t really know when I made them role play it out with another co-worker, while I observed. As I had expected, they either never really heard what I said or misunderstood, but judging from their role play we were not on the same page.

Similarly, if I ask a seller to send an email to an important account, especially an email that requires nuance and subtlety, I always ask to see their draft before sending.

As these examples show, you can overcome the challenge of coaching these types of “yes-you-to-death” sellers by positioning your coaching in a supportive way that emphasizes practice and repetition before “going live” to ensure the seller truly understands, and if they don’t, you’ve created a safe environment where they can ask questions to clarify the goal and expectations.

Type #3: Poisonous

These people have the ability to spread negativity throughout an organization like wildfire. They carry their pessimistic attitude wherever they go.

And in the worst cases, these people will even go as far as combining their negative attitude with the “know-it-all” syndrome. 

As you may already know, or can imagine, coaching this type of person is next to impossible. While you may have hired them for good reasons, the damage they are doing to the morale of the team is extremely detrimental.

While in some cases you may need to sever ties with this person, there are other cases where all hope might not be lost. There is a two-part strategy needed here. 

Part 1: Acknowledge the Obvious

Yes, that’s right, you have permission to directly address the “elephant in the room.” This is an obvious move, but not an easy one.

When we bring up the “elephant in the room” it usually revolves around addressing difficult people with hard-to-solve problems. It’s socially painful and can be a little stressful for people who aren’t comfortable with confrontation.

So, what usually happens is that everyone plays nice while never really identifying, discussing, or solving the issues at hand. Now the poisonous person, who knows meetings typically unfold this way, remains safe as no one ever confronts them. 

Stop giving them a pass. It’s time to ‘Acknowledging the Obvious’ by saying something like “…are you aware that every time I ask you to make a change you react in a way that makes it impossible for us to discuss the issue openly and honestly?”

Framing the issue in this way will allow you to start the conversation and bring the issue out into the open so that it can be discussed. However, don’t be surprised if the other person goes on the defensive. It’s a normal response when someone confronts an issue head on, because sometimes you have to break a few eggs to make an omelet.  

Part 2: Remove the Poison

This is the part where we separate the poison from the other members of the team. 

The most obvious way of getting rid of this person is to fire them. But let’s say that’s not an option and we need to get creative. Here are two examples from my own experience:

At one point in my life I was managing a team of salespeople who were unionized and the poison person I wanted to get rid of was the shop-steward. Once I was determined to get this person off my team they dug in their heels and threatened to use the power of the union to stay put.  Rather than directly fight union, I found this woman a better job—one where should could excel.

In another instance, a manager told me he had a poisonous salesperson that was related to the owner of the company. Due to the circumstances, the manager felt he couldn’t fire the person. How did he deal with it? He “promoted” this person to what he called Group 2. The salesperson was stunned. They asked what this meant and if they were really fired. The manager assured them, “you aren’t fired, but you’ve been promoted to Group 2, which means you don’t have to attend meetings or training and no more paperwork. All that’s required of you is to try to sell, and if you close a deal, then you get commission.”  

This manager’s approach to preventing these negative, poisonous people from infiltrating the rest of the team was to keep them separated. While this may not work in your situation, the point is to consider your options before letting that person go.

Managers should strive towards having healthy, open relationships with every member of the team. In some cases it will be more challenging, while in other situations it will be effortless. Take the time to support your sellers, even the difficult ones, by remembering to reframe the situation and pick the right starting point, remain helpful while reinforcing your expectations of each seller, and finally, be patient and get resourceful when necessary.  

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Topics: sales, sales manager, coaching, sales coaching

4 Ways Coaching Your Sellers Improves Sales Activities

Posted by Steve Bookbinder on Aug 16, 2016 3:45:00 PM

As a sales trainer I believe that every salesperson, including myself, benefits from sales training. I believe most salespeople generally know training is helpful, but, like exercise, not at this moment.coaching_solution-1.jpg

However, even those sellers appreciate the advantage of coaching, especially 1-on-1 time focused on their unique needs. Today’s sellers aren’t getting enough training to support their ever-changing and increasingly competitive world.

So, without a coach how can today’s sellers improve these vital activities?

#1 - Emails

Today, most sellers prospect by email. But has a coach critiqued what you’ve written in order to improve your response rate? When I coach sellers, we look at the emails they send. What we learn together is their opportunity to be less frustrated and more successful.  Most of the “first” emails are not personalized, the word choice too rambling, the benefits too one-sided toward the seller when they should be focused on explaining what’s in it for the prospect or customer. However, it is the 2nd and 3rd follow-up emails that benefit most from an analysis and rewriting.  My coaching uncovers opportunities to redefine customer profiles, customize new email templates, and re-strategize timing and testing while strategically layering in phone calls. During coaching sessions, I help sellers leverage personal marketing via networking and social media adapted for their unique sales role and territory.  The result is that sellers can measure improvement immediately, especially an improved number of first conversations with prospects.

#2 - Presentations

Most everyone has created and delivered a presentation in a variety of live and virtual settings, but have you ever had a coach who helped you analyze how to handle each situation or how to improve your closing ratio? When I coach sellers, we look at both their delivery skills and their presentation. This exercise helps to uncover how most sellers deliver a one-size-fits-all approach to presenting their offering whether it's a live demonstration to a committee of people or a 1-on-1 through video conference. Oftentimes, PowerPoint can make it difficult to illustrate your point because you may have too many pages with too many words, which doesn't help direct the sales conversation. Coaching shows sellers how to adjust both the content of the presentation and how they lead the conversation in order to advance the sale beyond the presentation.

#3 - Prospecting and Selling with Confidence

Every seller gets stuck when they encounter certain objections or issues. Have you ever worked with a coach to give you new strategies or ideas to solve these challenges? When I coach sellers, we dissect each stubborn obstacle that blocks that salesperson from building a path to their goal. I find the best way to increase energy levels and confidence is to help them overcome objections by inventing new ways of addressing customer issues and concerns.  As a coach, I work with each salesperson to understand what they are really trying to say and together we find a better way to say it.

#4 - Getting Back on Track

We are all assigned goals to hit, but have you ever had a coach help you get focused on achieving big goals or refocused after missing goals?  In my role as a coach, I have observed countless occasions where salespeople are uncommitted to their goals or unclear about what they are really trying to accomplish. In other cases, they are simply too beat-up from past failures to have the strength or courage to dream big.  Some sellers stop themselves from stretching to reach big goals because of personal fears, while others are boldly going off without a solid plan. When I take a salesperson through my coaching process, we begin by getting very specific about both short term and long term goals. I help them create a plan with benchmarks that enables them to track the little wins needed in order to be properly motivated to take each next step of their journey toward success.

Tune-Up Your Sales with Steve

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Topics: sales activity, coaching, sales coaching