What are the different things that sales enablement do in order to just basically achieve what we're looking to achieve with our organizations? Asks Jenn Haskell, Senior Director Global Sales Enablement at Monotype.

Giving her best techniques and strategies to better understand your sales people, Jenn explained the process of including a psychological aspect when building your training programs.

Here's her process.

Creating stakeholders

"Who are the stakeholders? Maybe the executive team, the senior leaders, the sales managers, your actual sales reps.

They are your stakeholders.

The most important part of creating those stakeholders was taking everything that I knew about sales enablement, putting it on the back burner and pretending I didn't know anything.

That is how you're successful as a sales enabler.

Just because I did something somewhere else and it was successful, doesn't mean I can come right in and do it here and expect the same results.

The other thing was communicating. We do a newsletter. It's awesome. It's a great way to help your sales team and to communicate with them on a regular basis."

Presenting a strategy

"I needed to make sure that not only did I present that strategy to my senior leadership team, but I actually shared it with my sales team as well.

I wanted them to know that everything we were doing was to help them so that as a company, we could achieve the things we needed to achieve.

Sometimes you find yourself asking, do sales reps give a shit?

They give a shit about being successful.

What they don't give a shit about is when you give them stuff that's not going to help them be successful.

Do yourself a favor, make them your stakeholders and create this sales enablement movement around them helping you help them achieve what they want to achieve."

Quick hits

"The type business I work for (Monotype), is really interesting. I walked on the sales floor the first week. Finally I took a manager in the room and I said 'what the hell's going on here? I don't hear anyone speaking. I hear no phone calls. What's happening?'

They replied 'you can't sell fonts over the phone. It's all done through email. Nobody will take calls.'

I also learned that the company had just gone to this open office environment. So now they felt like they were on blast being judged by their sales reps.

So the first thing I did was I was ask how do we earn some trust, how do I get some quick hits?

I'm going to use a pilot group. So I looked at that BDR inside sales team. And I said, if I can throw some quick hits in with this team, then I can share their success and their results with the rest of the organization. It's going to create this buzz.

So here's what we did. I said 'I don't ever want to hear again that you can't call a customer. I don't care what business you're in. You can call a customer. And if you don't feel comfortable doing that, I'm gonna give you exactly what you need to do that.'

It started with a lunch power hour session. How do you research and prospect, right started with another one. How do you do business communication? These are junior level sales reps, some of them are right out of college. So they really needed a little extra hand holding when it came to how you communicate with customers.

Then it started with Thursdays they did a call block from four to five and usually they weren't making calls. I would literally sit on a file cabinet. And they'd look at me and they're like, so you're going to give me feedback. And I look at them and I say, No. Do you want feedback? I'm listening. I'm trying to learn the business. I'm onboarding here, you're helping me. If you want feedback, I'll give you feedback. But I'm not just going to force my feedback on you.

It was amazing, the reverse psychology of that they wanted the feedback. They didn't realize it, but at the time, I was building a program for them. We started to implement virtual roleplays. We started to do video based coaching assessments through the brain shark platform. So after about three months, their LinkedIn connections went up by over 400%.

They were starting to show that they had mastered certain content. They were making more connections, and their call rate went up 84%. They weren’t comfortable with being uncomfortable. They just needed to know that they could try it, they could learn from each other, there was a benefit to being in this open office.

I was able to start sharing that success throughout the organization, but it was very much don't take sales enablement word for it, talk to their managers see what their managers say, because now they're a champion of sales enablement and this new movement."

The tale of two E's: enablement and empathy

"It was the best of times.

When you come out of a program or a training session and just feel amazing. I nailed it. I feel good. It's awesome.

Enablement is a complete roller coaster because three days later, it's the worst of times.

Nobody likes what you're doing. Your newsletter looks like it's from 1992. That's a real quote, by the way. You feel like you can't win.

But for us, it's always about the wisdom, whether we're providing that wisdom or whether we're gaining that wisdom from the team. I always say to my team, I can learn just as much from you, As you can learn from me."


"I don't think you would be a successful sales enablement professional if you did not know how to practice empathy. Empathy is being able to recognize your own feelings. It's being able to recognize someone else's feelings.

It's very different to sympathy. Sympathy is very appropriate at a funeral. I'm sympathetic, I feel bad. Don't be sympathetic to your sales reps. That's counterproductive.

But certainly think about the programs you're making in an empathetic way."

stationery love
Photo by STIL / Unsplash

Organizational behavior

"When you create programs today, think of organizational behavior in the process of designing those programs.

It's the study of both group and individual performance and activity within an organization. It is the area of study that examines human behavior in the work environment. It determines its impact on the job structure on the performance, the communication, the motivation, the leadership, etc.

There's five versions of this.


Not good. I don't think any of us would do very well in a sales enablement role with an autocratic model. Real old school. loyalties to the boss. There's fear. You're lucky to have a job, right? It can be incredibly toxic.


All about the money. I think about the 80s right? Wolf of Wall Street type thinking. How can we give you flashy benefit packages?


All about teamwork. It's all about working towards one simple goal together. It's all about inspiration, right? Your sales managers take their role as being the ones that can inspire very seriously.


All about recognizing your rising talent. We've now got the talent, how do we keep them? How do we grow them? Who are our future leaders?


Trying to balance the varying goals of the individual with the wider goals of the company."

Emotional intelligence

"It's really just being able to understand your own emotions. Some people have a natural ability and a high EI, some people don't. This is a skill that sales reps need, they need to be able to pick up on cues, they need to be able to read clients.

Self awareness

Being self aware is understanding myself in and out, side to side. What motivates me, what drives me, what are my strengths, what are my weaknesses?

Self regulation

Self regulation is just keeping ourselves in check, not taking things personally. For sales recruits, self regulation is to get them to the point where just because they fail, they don't shut down.

Social skills

Being personable. We can coach on that. We can provide examples of what good social skills look like, or we can create development plans to help them.

Hope and optimism

It would be very tough to do what I do today and not be optimistic 90% of the time.

Companies that focused on employee motivation and engagement, realize 27% higher profits 50% higher sales, 50%, higher customer loyalty levels, and 38 above average productivity.

Motivating a sales team does matter. It impacts not just your ability to retain your talent, but also your customer and buyer journey."

Three types of salespeople

"We have our underperformers. We have our core performers. We have our rock stars.

The core performers can get forgotten about. When we go to kickoff, who gets all the credit? They deserve it. They work their asses off for it, it’s the rock stars.

As enablers, this is a group that we sometimes try to tap into too much. Why? They work really hard. They travel a lot. They work ungodly hours.

But the unsung heroes are often the core performers. What better way to encourage them and to motivate them, then to give them an opportunity to come in and speak to a team.

I'll call a core performer any day and say ‘Hey, do you mind calling two slides together to deliver during the next power hour, you're really good at research and prospecting, or I think you could really provide some good insight to our BDR inside sales teams.’

These are individuals where the talent is there, and we have to prioritize our ability to bring them to the next level because they actually want to be challenged.

Then the under performers. Sometimes the core competencies weren't there to begin with, and that's going to require a lot of hand holding. But I have seen a lot of success stories don't give up on them."

Motivational techniques

Talk to them!

"I will sit with my reps and just say 'Hey, how's it going? What's going on? What can I help you with?'

I want to know what they consider important.

I give them opportunities to communicate to the rest of the organization. Whether it's shout-outs in our newsletter or spotlighting their sales deal. I'll say ‘bring me a deal you won. We're going to write up a sales spotlight, we're going to give you a little credit, I'm going to throw you $100 gift card.’

And they all want to do it because now it's a competition. who the heck doesn't like to be on a stage getting a little bit of attention?

I'll also say if you lost a deal, so what? We lose deals all the time. Give me a spotlight out of your loss, I'll give you $200.

We're their advocates guys, remember this. We advocate what they need to our sales managers and leaders, we advocate for what they need to our product marketing team.

That is how you achieve ultimate trusted advisor status.

Understand their personal goals

I truly believe that if you don't understand what every single one of your rep is driven by what they want to achieve, where they want to go in their career, if you can't have that open line of communication with them, you're probably cranking out some good programs, but you could be cranking out better programs.

Focus on behaviors rather than the results.

Make sure that your version of what good sales rep behaviors are matches what your sales managers and your sales leaders think in your HR tool.

Start with KPIs and work backwards

Ask what's the measurements of success? What's the KPI that this is directly going to impact? I always emphasize learning by doing. If I don't actively listen to my sales team, how is my sales team going to actively listen to others? If I don't pick up on social cues how is my sales team going to pick up on others?

Do it again and again

It's not a one and done. You can't just do this once and expect it to stick. It requires consistent reinforcement. Sales behaviors, drive sales activities, and that in turn is going to give you the results that you're looking for. So focus on the behaviors versus the results."

This article was adapted from a speech Jenn gave at the Sales Enablement Summit in San Francisco