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Is there anything more annoying than curating great sales materials only for them to fall on deaf ears? I’m sure we’ve all experienced it, the feeling that our salespeople don’t give a shit, but what can you do about it?

I’ve come up with five key areas of focus that can lead to success, and ultimately salespeople who do give a shit. From building trust to tying your efforts back to results and everything in between, in this article I’ll explain how you can get salespeople to care.

salespeople don't give a s**t

Salespeople don't give a shit in a lot of situations, what can you do about it? That's what this article is going to be about - what are some tactics and things that we can do to help you get your sales team to care about the content that you're distributing and the training that you're doing.


Before that, just a quick intro. I come to this role, the actual title of enablement a little bit differently. I've had a couple of different roles where I did enablement but didn't have the actual specific role.

My name is Trent, my core focus is actually on Zendesk Sell, which is our sales tool at Zendesk. It’s newly acquired, I'll get into that in a moment. Before I get into my current role and some of the things that I do, I think it's really important to talk about how I've identified why I don't think salespeople care about things.

Global Sales Specialist

One of the roles I had at Zendesk was a Global Sales Specialist, it was a super interesting role. I actually reported under the solutions consulting organization, so it was go-to-market, but I was a specialist for the entire globe.

goal: increase global attach rate and ASP

On the left-hand side above, you're seeing product ‘expert', and that's in air quotes on purpose because I am a salesperson, I am not technical, and more often than not, I knew just a little bit more than the actual sales rep.

The second thing that I was doing to help hit the global chat number was I had to turn this corner and start training one-to-many. That's really where I got my first taste of enablement and training and then from there, while I was doing both of those things I actually carried again that global number.

I had an interesting view and that's how I landed on the topic of this article because I had to turn this corner of my sales enablement team often did a lot of trainings and I always felt like, "Oh, man, I don't care. So I'm going to be different".

I stepped into this role and I was like, "Man, I have a lot of roadblocks. I have a ton of different roadblocks". I was a one-person team and I had to train the entire world on how to sell Zendesk Chat, a messaging product of ours.

Expected roadblocks

The first problem, the first roadblock was there were 300 sales reps and one of me globally with a wide range of skill sets, so SDRs all the way up to national account executives.

From there, we have a ton of distractions and then, of course, fast-paced growth.

'expected' roadblocks

For those of you that don't know, Zendesk has skyrocketed in the customer experience world. When I started, there were 800 employees today there's about 3500. That fast-paced growth creates this natural roadblock of distractions and all these wide-ranging skillsets and then of course having to adapt to new products etc.

Expected outcome

I had this expected outcome - yes, I was a little bit naive and I thought all the stuff I was going to do was going to work, it was going to be repeatable, it was going to be scalable, it was gonna be fun, it was gonna be interesting.

'expected' outcome

Nope, turns out that I was doing all of the same things that I hated when I was sitting on the receiving end. What led me to this concept is I rolled out the plan, I did all these things and I still felt this…

salesepeople don't give a s**t

I was like, "Man, I need to fix it". I started fixing it in that role, I did various things, I'm going to get into those in a moment, and then something interesting happened for me. It was kind of a self-reflection moment, we acquired our Base CRM, you may be familiar, and I was asked to take a formal position in running the sales enablement team for this company that we just acquired.

Zendesk acquires the company behind Base - news story

They were going to run separately and there were about 20 reps and I was like, awesome, sounds great. I've been enabling, I'm starting to feel like I know what I'm doing. I still had this big problem of, "I still need to figure out how to get people to care".

Global Sales Enablement Manager, Zendesk Sell

These were the responsibilities.

responsibilities at Zendesk Sell

That quickly morphed into this role where I was like, "Oh, I have 20 people. It's all contained". And it shifted into "Hey Trent, can you enable the whole world on Zendesk Sell?"

I was like, "Oh, shit, here we go again, I have to do this again".

Expected to expected

But I did learn a few focus areas or a few things. This time, I expected the expected. I didn't come into this role, or I didn't come into this responsibility having all of these roadblocks that I had in the last.

expected to expected

This time, I had one job and that's what I was going to stick to - getting people invested in what I was talking about and getting them to learn.

Five areas of focus that lead to success

I'm going to give you five areas that you can focus on to either help your team roll out a plan, or five things that you should be focused on when implementing training or going into some sort of presentation, etc.

Focus 1: building trust

The first one is building trust with your sales team. This has been talked about in various ways, I don't really think there's anything new under the sun, especially when it comes to salespeople. But building trust is extremely important.

I learned this the hard way. I came into a lot of deals, I would help people, I was training them, I was sitting side by side, and basically, they were like 'you can't possibly know what you're talking about'.

How many people have listened to a sales call in the last two weeks?

How many people have listened to a sales call in the last two weeks?

This is a really important question to ask yourself and your team and also those that are impacting what content and information that your sales team is going to get.

How relevant is it? This starts to build some trust.

Recently I ran a survey, just a small survey, very informal and I said "What are the top two things you hate about enablement?" - I used ‘hate’ on purpose, I wanted them to give me an aggressive answer and I wanted them to be very honest.

what are the top 2 things you hate about enablement?

50% of them said, "Enablement pretends to know what sales is like". Basically what that means is we can't possibly know what their world is like. We can't possibly have this context and this understanding of how complicated being a salesperson is.

backseat drivers
Prove understanding by building trust

Well, we do, and we have to prove that. One of the ways we can do that is by building trust.

If this is the world that they think we live in, that we're backseat driving and we're the armchair quarterback, we have to fix this problem. The first thing that we have to fix is building trust. Before we do that, I want to talk about how I think this problem has actually come about.

Problem: information flow

I think this concept of information flow is super important to why salespeople think people in my position or product marketing and sales enablement, don't trust us. That's because they're getting things that they don't use. They're getting things that haven't gone through a sales filter.

problem: information flow

Looking left to right, I think this is very much how content is created. There's idea, research, testing > goes to product marketing, then often it skips over this sales filter and this idea that this has to be sales-ready, it needs to be consumable, be bite-size, it needs to be easy to understand.

This is a concept that I take very seriously and anything that comes near my reps is - is it ready for them to actually use and will they actually use it?

Again, I think if we can implement something like this in our thinking, we'll start to build some of that trust. In order to do that, we have to be able to tell a good story.


I think telling stories leads to being very trustworthy when it comes to the person either delivering the training or you guys who are bringing in the person doing the training. We have to ask that question.

facts tell, stories sell

This concept of, 'facts tell stories sell' goes back to the content, we need to be the person that creates that story and creates that trust. This concept I implement in every conversation that I have,

"Okay, tell me a story about why this metric exists or why this one-pager exists".

An example: Alaska Airlines

An example of storytelling and an example of something that could be used in training, but probably isn't, comes from Alaska Airlines. I'm using this example not to get you to buy an Alaska credit card, although you should, it's fantastic, but to explain to you the impact and the trust built around storytelling.

I was recently flying and I got on this flight to Eugene, Oregon from Seattle - about 45 minutes - the flight attendant at the end gets on and she thanks us with the most emotional thing I've ever gotten in my life. I was like, "Wow, you're welcome for flying Alaska Airlines". That's how I felt.

Then she turns the corner and she starts talking about the credit card and I was like, "You've got to be kidding me. Really? You just had me all excited, and all ready to be like, yes, I'm flying Alaska, I'm part of your journey", then she started selling to me.

But she didn't just sell me, she told me a story. She got me to trust her in a way that I've never trusted a flight attendant selling me a credit card, which was kind of crazy. Instead of saying, "Hey, we're going to give you 40,000 miles" she started with, "We're going to give you four round trips to anywhere you want to go".

Alaska Airlines storytelling example

Then she goes down, one full round trip anywhere, etc, etc. Before she ends, she asks, "Hey, how many of you have the credit card in the airplane?" And 20 out of the 40 raise their hand and they did. What's crazy is she was so damn good at this, that 15 out of the 40 individuals took a paper pamphlet from her.

Are you kidding me? A paper pamphlet and they started filling it out. That's how good it was.

Now, I'm guessing Alaska Airlines has no idea that she's that good at that. I'm guessing because the Alaska Airlines sales enablement manager isn't on that airplane listening to her sales rep, that they aren't implementing this elsewhere. And then when they do training, they don't have relevant context.

They don't have relevant feedback from actual experiences, building trust into their content delivery, and therefore it all falls apart because that's the only time I've ever seen that happen.

What can you do about it?

I think this concept of y'all listen to phone calls, but I think we need to do it with purpose, instead of just listening to recordings, I highly recommend doing live calls, taking notes with your AEs, watching how they react to customers, etc, is super impactful.

I think we can all agree that we sit through 100 meetings in a week and if we could get these bullet points from any of those meetings that we sit through, it would be fantastic.

enablement neglects sitting in on sales calls

Yet we neglect sitting on phone calls with salespeople when we can get all of that in 30 minutes. Be the filter, be the change, be the leader, and build that trust with your AEs.

be the filter, be the change, be the leader

Focus 2: examine relevance

Focus number two is to examine relevance. This is a concept that I had to come up with very quickly because I was the only one - how to train on relevant topics.

The next piece after you build trust is determining what's relevant to the AE. When I asked these AEs what are the top two things you hate about enablement? This was the second answer I got, that enablement content isn't relevant.

what are the top 2 things you have about enablement?

It was almost 100% I think, the other individuals that didn't answer it answered it third or fourth on their list.

This is crazy because we think we're distributing content that helps them do their job and make money and so I think it's how often it's being used, and how often it enters the salesperson’s brain.

The 7-day rule

I came up with a seven-day rule based on my experience with sales individuals and what content worked. Specifically, in my role as a global chat specialist, I was constantly in the trenches and I was like, "Oh, man, they say this or this or this competitor comes up all the time, we need to do a training".

Yet I found myself doing a training on competitors that were outside of seven days and I realized that's when people stopped caring. That's when people stopped paying attention to me, so I implemented this and it worked.

The 7-day rule

Every single person was like "I'm using that now. I have a call tomorrow. I have a call Thursday" I think if we do this, our brain gets us to start saying, "Hey, this is a relevant topic, I trust what's happening. This is something I need to pay attention to. I'm going to care about this information that this individual is telling me".

Some examples outside of just how often it's being brought up:

  • Deal lost reasons,
  • Number of objections,
  • Number of times a question's being asked, of course, and,
  • Customer feedback.

That last one is probably the biggest, ask your customers in some capacity what they liked, what they didn't like about their sales experience, you'll learn a ton from that.

Is data enough?

Not all of us have the luxury of being able to have all of that data and be able to map data to results and all that stuff. Something that you can do if you can't get the data, but I also recommend doing this regardless, is providing the evidence - how do you do that?

Focus 3: provide evidence

Before I get into it, I think we've all had this problem in some capacity, someone coming to us saying, "Hey, we need to solve this problem. We need more money. We need more conversion rates. We need to cross-sell more" Then they go, "Well, I recommend you do a live training".

I can't even tell you how many times I've been told that "You should schedule 30 minutes". Why? Are you kidding me? "The desired outcome is the attach rates will go up". Oh, right. Totally. Because you've run a training full of 90 people that aren't listening to you. I'm sure that's what will happen.

problem, recommendation, desired outcome

So prove it.

I had to do this because I was basically told to go train the entire world on Zendesk Chat and they told me that if I did that, we would go over 100% or whatever. How do I do this?

Gather evidence

I had to gather evidence, and I implemented what I call a zero to hero method. Again, it was one v 300 and I had to get the number over 100% and so I had to do this through them.

Zero to hero method

This is your sales team in entirety.

zero to hero method

The 5% of the top is your top-performing reps, the second layer so on and so forth, all the way down to your bottom. I implemented all of my testing of whether or not things were relevant, the topic was going to be successful or if the things I was training on were going to be relevant at the level right below those individuals who were hitting quota or sometimes they hit quota, or sometimes they wouldn't.

My point is I did all of my testings on that specific segment and let me tell you why.

When you have reps that are typically not hitting, and the reps at the top see reps that weren't hitting start to hit and they start asking why? Your content, your training, the stuff that you're putting out there will flourish, you will start to see the impact of your training so much faster.

We did end up going over 100% globally by implementing this and it was not because the content was crazy good, or that I was great, but it was because people were having success with small things that I was giving them and that's where I tested it.

Now what's important is every time I tested it, I said, "Hey, this worked", and then I would step into a big training like this and I would say "Here's why you need to do it".

They would look around, and they would say, "Oh, Steve and Susie the 40% that was just below is now teetering at the top". So provide the evidence and another way to look at this is consistently attain quota, consistently teetering, consistently missing.

consistently teetering quota

I focused on that middle one.

Focus 4: establishing return

I think this one is huge - establishing a return on what you're doing.

What we see

I think this concept of we enter training with an expectation of, 'we're going to get smarter reps. If I do this training, if I do this enablement session, if I do the speech, we're gonna get smarter reps, we'll likely increase revenue, we'll have more at-bats, decrease losses, happier AEs, etc'.

establishing return

That's all fine but that is not what your AEs see.

What they see

They see this overwhelming, complicated world that they currently live in.

the AE daily grind

This is overwhelming on purpose because this is the day of an AE. I think we all kind of understand this but if tell them you have to take 30 minutes away which one of these 100 things are you going to take away? And how are you going to establish the return on taking that? They'll say,

"You're going to take 30 minutes, I'm not going to be able to negotiate with my customer or do this or do that". Or, "I'm just gonna go on my phone, I'm not gonna listen to you".

There's nothing there. If we don't establish credibility or we don’t' establish there's going to be a return they're going to say, "You haven't told me why I should listen and you're gonna take time away. Well, if you're not going to tell me, I'm just gonna go on my phone". Great.

I've lost you. What can you do?

Return on listening

This is a very, very simple concept that we forget often, and by we I mean me, even sales management when they do training, they forget this constantly. It's something that if we just embed this very simply, you will get a ton more out of your session.

return on listening

Again, that's providing trust, having a relevant topic, having the ability to prove it, and then providing a return on your listening before you enter the room or even as you enter the room.

It looks something very similar to this, "Hey, you give me 15 minutes, I'll give you three ways to dominate competitors. I'll give you two proven methods to establish confidence which ultimately will lead to you getting 5% more revenue, hitting your number, etc.".

in this 15 minute session, you will learn how to...

Very, very, very simple, and if you remember this in all of your training, whether that's a lesson, an online training, whatever it is, "You're going to start this, you're going to give me this much time". Be sure to remember this one, this one has been highly impactful for me.

Next time, if you provide that return on listening, instead of them thinking that they're going to set their fantasy football lineup during your session, (because that happens, God, I've walked around and seen that and it's awful, especially when you find out they took last, like damn it, you didn’t even win), we will set the stage a lot better if we have that return on listening and we'll get the buy-in and we won't have to worry about them being distracted.

what does the rep see of you don't provide return on listening?

Focus 5: tie back results

Tying back all of the things you just did to some sort of win or customer story, whatever it is.

AEs are our customers and so we need to prove that by having all of these experiences that we've now established. This is a checkmark, we need to just check this off, this is something we have to do.

tie back the results

I'm not going to go through each of these points. These are just some things that you can look at as things to send out to your AEs, to your managers, to your leadership team that you helped solve with your training.

If we don't do this, people forget how impactful you were. They so quickly forget, especially if you're outside of that seven days, because apparently, no one's brain works outside of that seven days, or at least that's what I've learned.

Did it make their job easier?

At the end of the day, did you make their job easier? If we're going to do one thing in sales enablement and sales training, sales management, whatever role that you live in, does it make their job easier?

If you can't answer that question with a 'yes', I highly recommend reevaluating what content you're distributing and how you're distributing that. Because that is our job - to make them more successful and make their job easier. Post it, email it, Slack it, climb a mountain, run a commercial, do something, and tell them you had success and how you had success.

I think this is extremely important and I really think tying it back in and making it known that the training that you delivered or someone delivered through you was successful.

Stop training on things reps don’t care about

For the love of god stop training on things that they don't care about. I think that's something that I see constantly, whether it's new hire training, whether it's product training, whether it's a PMM coming in, whether it's ops telling me to do some process, guys we can stop this from happening, we can stop people from not caring.

stop training on things that they don't care about

Stop trying to 'make fetch happen' and in this case, stop trying to implement things that people don't understand or don't listen to.

The path to getting your sales reps to give a shit

What can we do when we're rolling out an enablement plan, a path, a training?

The path to getting your sales reps to give a shit

If we roll out a plan that has all of these elements backed by data, and maybe customer stories, etc.

  • If we can tell a story and create that trust,
  • If we implement some sort of relevant parameter,
  • Explain why it's relevant,
  • We move into gathering evidence (I use the zero to hero method - that's a difficult one to scale but let's see if we can find that evidence),
  • Return on listening,
  • Make sure we establish that, and then last but not least,
  • Make the results known.

Do not let your work fall on deaf ears. We are so vital to the success of an organization and the sales team, the last thing we want to have happened is for us not to get at least a little bit of notoriety, a little bit of credit for what we've done.

Not saying you need to be the high and mighty - sales is always going to be the high and mighty - but we can definitely be the person that helps them do that and get a little bit of credit along the way.

That is everything I have on how to get salespeople to care. Thank you.

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