Episode 40: The Connection Between Training and Coaching


Shawnna Sumaoang
Shawnna Sumaoang
Vice President, Marketing -Community, Highspot
Jonathan Easterling
Jonathan Easterling
Senior Sales Enablement Trainer, Ncontracts
Podcast Transcript

Research from Public Personnel Management found that training alone leads to a 22% increase in productivity, while that impact jumps to 88% with a combination of training and coaching. So how can you maximize the impact of your training and coaching programs?

Shawnna Sumaoang: Hi and welcome to the Win Win Podcast. I’m your host, Shawnna Sumaoang. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Jonathan Easterling, senior sales enablement trainer at Ncontracts. Thanks for joining, Jonathan! I’d love for you to tell us about yourself, your background, and your role. 

Jonathan Easterling: Absolutely. Thank you so much for having me today, Shawnna. I really appreciate it. As you’re saying, my name is Jonathan Easterling. I am the senior sales enablement trainer at Ncontracts currently. I’m just outside of Denver in a town called Fort Collins. Leading up to Ncontracts, I’ve been in various B2B selling jobs, led team management, and went on the traditional path. Being in management, you have the opportunity to develop your team. I really enjoyed that piece. I had a chance quite a few years ago now to jump into training and I have not looked back ever since. 

SS: I love that. Now to start, I’d love to hear from you. Can you share a little bit from your perspective about the connection between training and coaching and how the two can complement each other?

JE: I hear this often when these two aspects are decoupled and the way that I think about it is I think of my sellers as fighter jets. We give them the core skills and the competencies to really get them off the runway. That’s where the training kind of fuels the thrusters. We got him up in the air, but the coaching is the aileron. The coaching has the seller moving towards the target and when we decouple the training from the coaching, then we’re leaving a seller with really all thrust and no vector. Sellers, as we know, really want to get after it and they’re happy to fly hard and fast with thrust only. We have to make sure that we’re jumping in post-training and we’re making sure that that coaching is keeping the direction true. 

SS: I love that. Now we have a theme going on around what good looks like. I’d love to hear from you. What does good training and coaching look like? In other words, what are your best practices for building an effective training and coaching strategy?

JE: What good looks like is kind of a varietal question. It hits differently for every organization and that’s what I initially thought when I approached that. As I pulled myself to a little bit higher level, which I think is an enabler we have to do, I realized that that’s actually kind of not the case. I want to do a quick little reframe if I may, what does good training feel like to the trainees? When I looked at it from that aspect, I was like, okay, well, what’s the goal? What’s the goal here? The goal of any training is to get the skill and the will levels matched, and ideally, both those levels are very high. The reps feel empowered to do what they want to do and they are excited to do it. 

Now, I break it down into just a couple of different categories when I’m approaching this. For me, what good looks like in my organization is tiered, digestive, digestible, and iterative. Let’s just take a peek at a couple of those. Tiered, which means, it’s not a blanket approach. This is targeted, prescriptive, and it’s going to be different for each level of employee. We all know we can’t just deploy one program and say, okay, all right, good job everybody, let’s call it a day. 

At the seller tier, they may need something a little more technical, a little more point-and-click, and maybe a little more role-plays or gamification. At the leadership tier, we may need a different level of technical skillset. Maybe they need something a little more administrative, or maybe they need more soft skills and more training on coaching or coaching on coaching to be able to implement that training correctly. 

It is all iterative. Luckily, I was part of an organization early on that taught me how to fail forward and really gave me the opportunity to do that. I’m not afraid, and my organizations are not ever afraid to go back and relaunch and edit what we’ve previously done. We don’t really carry that level of indignance with us. We are not under the belief that managers should handle that whenever small iterations come down after training. We go back and republish, we relearn from the mistake and we just do it better next time. It’s iterative. 

First of all, it’s digestible. Now this one’s difficult. I’ll tell a quick little story about this. I train at a jiu-jitsu gym and one of the instructors has an adaptive living class called be bold. When you go into a bold class, you will see people of all physical capabilities. You’ll have professional fighters and you’ll have quadriplegics in the same room getting a sweat on and working out. When I looked at that, I said whoa, everyone in this room is baselined and engaged. Now from a training aspect, that is a huge cold water over the head that you’re saying, wow, if this can happen, what am I missing in my groups that are highly vetted? We want to make sure that it’s digestible to everybody in the group. 

This isn’t easy. To do that, we can over-communicate with our stakeholders. This is going to be another bucket of cold water for some, for folks, don’t skip your postmortems. If you fail, really rip it apart. Sit in that for a minute and make sure it doesn’t happen again or at least that you learned a lesson to take from the next time. Don’t be afraid to mess up every now and then. I think this is a really interesting time for enablement altogether as we look at what good looks like. Enablement has been completely upended by the change in the workforce. This is one profession that has really set the level playing field. People that have been here for 15 years, people that have been here for five years, they’re kind of on an equal playing foot, figuring out what works in this virtual hybrid environment today. Super exciting to be able to find out what good looks like. You might find something seriously game-changing if you flip your own script.

SS: I love that advice. Now you’ve leveraged Highspot to train and coach reps, both at Ncontracts and in a previous role. What are some of the common challenges that you’ve experienced when it comes to training and coaching reps and how has Highspot helped you overcome these?

JE: I think initially when we have this bevy of information that we have to get inter-departmentally down to the sellers, there’s a couple of key pieces of information that the sellers really need. Finding that content without a repository that’s very simple to navigate, ends up being this byzantine conduit of channels to try to get the seller something that’s actionable. As we know, if they’re not actionable on it very quickly, poof will be gone, the training not strong, and it’s going to be really tough to actually get them to implement it.

When we have a platform, like Highspot that categorizes and organizes a taxonomy that is well beyond any of its competitors in terms of simplicity, user-friendliness, and navigation, now we’re getting those sellers, the type of content that is super relevant to them at the seller’s speed. We need to get things at the seller’s speed. They are going to move fast and they’re going to look for something very quickly. If they can’t find it, then they’ll make up the narrative and we don’t want that. We want them to have the best information possible and always feel equipped to do their job the best.

SS: Fantastic. Now to shift gears a little bit, one thing that caught my eye was on LinkedIn you had shared a few tenants that you collected throughout your career. One of them is to better the environment, better the individuals. How do you help create a healthy sales culture through your training and coaching programs?

JE: I love this saying, thank you so much for being able to pick it out. Luckily in sales enablement, we do that as kind of a proxy. Now, initially, when we’re creating these sales training and programs, let’s start from the beginning, what do we have to do as enablement? We have to stay available. We have a lot of backend stuff, like presentations, events, and curriculum that we’re creating. We have to be present for our sellers initially because they’re telling us what’s wrong, they’re telling us what’s working and they’re telling us what’s not working. They’re really our first toe in the water for a temp check. 

Second, but I almost call this 1A is about transparency. There’s no guesswork. Right. That old adage. If it’s not in Salesforce, it doesn’t exist. Well, luckily with the analytics that Highspot provides when we’re looking at things like usage time, click-throughs, the specific calls to action that we can set, now we’re setting a level of transparency within the organization that says, hey, we’re all here to do the same thing. Let’s talk about some concrete objectives that we’re working towards. 

SS: I think that is fantastic. What are some of your best practices for creating effective training programs in Highspot? 

JE: When we’re looking at an effective training program, I’m going to draw it up a little high level because, again, it looks different to every organization. I look at the overall principles. One of the big mistakes that I made early on in Highspot was because it is so exciting to get everything so direct to my reps, I got kind of confused and I created a couple of sales plays that had way too many calls to action. What I took from that is a best practice for an effective training program which is that it has a single or very few calls to action. As I started to implement fewer, more specific calls to action, I found that I had better uptake of the completion of the call to action. I got less recidivism into the programs and I got a better overall average initial scores. That would be the first thing I’d say, just try to focus on as few objectives as possible to get your sellers actionable on those objectives.

Secondly, to kind of harp on what I had said before, iterate, iterate, iterate. Highspot has an amazing function that you are able to not only curate your content, but you can very simply replace a new piece of content that has come out and you’re able to see the longitudinal data of the old piece of content and the new piece of content. With that, you can iterate your approach, you can go back to product and marketing and say, hey, we actually need to iterate this piece of content, but being hypercritical about the things that you’ve done and then letting the data speak for itself.

Oftentimes we can get emotionally tied to this project and this baby that we’ve created. Luckily, with Highspot, we’re able to pull that emotion out of it and say, oh shoot, objectively that just didn’t work like I thought it would. Now, let’s actually make this baby the one I really wanted, but we want all of our babies. 

SS: So relatable. How do you then reinforce that training through coaching?

JE: When I’m reinforcing training through coaching, for me, it’s important to be able to, again, I’m going to call back to those specific calls to action that I was able to develop in the past. I can coach on things that are soft skills, like, good introduction or like not hard pivoting from process and value-based discovery. I can teach these things, but when I need to have technical-based coaching, there’s really no replacement for a hard analytic-driven conversation. When I’m pulling that data down, I think for me personally, and from what I’ve heard from my reps it really softens the blow instead of it being heard as a personal thing.

It’s like, hey, I really didn’t like that introduction, but when we combine things like integration of Gong calls with our Highspot scripts into our sales plays, then we’re creating a holistic view of the sales motion and we can say, hey, actually we use this introduction over here, but it actually kind of led to a little bit of a slippage. Let’s try a different introduction that maybe one of your other seller friends had used, again, going back to that transparency part of it and we can have a more factual conversation that says, hey, we’re just going to get you from this step to this step.

SS: I think that is fantastic. Now, coaching can often take a backseat, especially as we all get busy, but teams really can’t afford to let that happen. I know that you are adamant that coaching is a key priority within your organization. Why is coaching such a critical part of the formula for improving sales productivity?

JE: I’m going to go back to the jet analogy, thrust, and vector. As the jet is moving through the air, i.e. as your seller is progressing through a sale to land at the close, we all know the air has weather, i.e. there are other things within that organization, within that client, with their personal life, with their social life, professional, whatever, that is happening. That can really throw a seller for a loop. You give somebody a call, you’re in stage three, and suddenly you’re like, my dog just died, and you’re like, man, how do you pivot off of that one? To be able to have a coach, someone that is close to you during those sales and during those moments, again, with that transparency, with that factual analytic driven conversation to get you to that next level you cannot separate those two. 

When we’re going through coaching as in training a coach, we can use dashboards within the platform to get middle-upper management to buy in. Now, how do we do that? Well, it’s very simple to create your own comprehensive dashboards in Highspot. What we can do is we can just hang out. We can hang out with our managers, we can meet with them to identify the metrics that we need to drive with them together you can create these dashboards. 

This does a couple of things initially. It makes it super easy for them to jump in and check out where their team is at. They’re already pumped at that point. Secondarily, this is like a mini discovery session for us. We get to find out what are the overarching drivers, are the quick objectives, what are the long-term objectives, what are our quarterlies and what are our annuals. We can always start to have those in mind as we’re developing future trainings down the road. It’s kind of a two-pronged approach. 

SS: I love that. Now you mentioned that you aim to encourage coaching and mentoring through the Highspot platform. Can you talk to us a little bit about how you approach this as well?

JE: The aforementioned meeting with the sales managers is one way that I like to build rapport within a new company. I like to come in and say, hey, I’m actually here for you because that’s what I’m here to do. I need to translate what’s important to you and get it to the sellers so we can then we can all go have our quarterly party every year. 

One of the things that we implemented recently that I thought was really fun was utilizing the Highspot social aspect. You can comment, you can like, and you can share edits. There is a strong social aspect of it that’s super easy to use. What we’re doing is we’re implementing what we call an SOS spot, or a support on-site spot. This is to increase social interaction and we’re hyper-focusing on this page as a social forum for people to post Gong calls, post emails and get feedback within the organization. It is like a war room where we unabashedly can tear each other apart and go back out into the marketplace and close some deals there. 

SS: I think that is very cool.

JE: We’ll see if they do it. 

SS: Now you also mentioned how important it is to partner with sales managers to help them be effective coaches and mentors. What are some ways that you leverage Highspot to do that? 

JE: As the initial Olympic run of the torch comes through onboarding, that’s how I like to think of us marching down with the torch, lighting up everybody’s brains with all the new knowledge through onboarding, the managers are what is providing that ongoing vector through the air. They’re coaching every day. They see their employees more times a day. They just hear more from the reps. When we’re partnering closely with them initially, that means We’re going to empower them to find the data themselves. We’re going to get very close to them and we’re going to let them know how powerful Highspot is to give them the ability to have real-time insights into what their reps are doing. 

For a sales manager, data is king. They love getting data. When we build it in conjunction with them, they have awesome buy-in, and they’re really empowered to use it because it’s metrics that they care about directly. It’s important that we’re meeting between departments as well because our business development manager is going to have different metrics than our enterprise has, and different than our mid-market needs. We have to meet with each of them because then we can start tying the threads together. 

Now you’re asking about partnering with sales managers. For us here at Ncontracts and for my previous roles using Highspot, sales plays, and pitch styles have been absolutely integral in providing sales managers with that sales flow motion view. Sometimes we can get a little disconnected by viewing the pipeline in our sales motion in Salesforce. It can kind of seem like a stop-and-go, but with a sales play and a pitch style, you get a holistic view of how a seller is going to move through what you intended from point A to point B. This is what I call from contact to contract. We have a path we want the sellers to take. We partner early with our managers to identify exactly what those calls to action we want them to enact.

Let’s say at stage four, are they using the ABC proposal deck? Then we get with those managers and say, hey, does this sales play actually feed the data that drives your metrics? Are we actually putting information out there that you can pop into that dashboard that we created and see that it’s actually accurate? This is why it is important to go back and meet with that manager and say, hey, is this still relevant? Or, hey, I changed this, do you want to add this type of metric to it? 

SS: I love that. On the note of metrics, last question for you, how do you measure the business impact of your training and coaching programs, and how has Highspot helped influence the business impact?

JE: You’re going for a loaded one on the closer, huh? I see how it is, Shawnna. Oftentimes we can find ourselves in a tricky predicament in enablement. A lot of the time as enablement, we fall into the revenue department. Our metrics can align very closely with sales, such as time to close and average deal size, but we don’t necessarily have the direct line like a sales manager would coax that trajectory as it’s happening. 

Highspot has some features to help us identify exactly what has or hasn’t contributed to the goal of closing more business. Integrations with things like Salesforce can help me see exactly what piece of content was used or wasn’t used attributing to our slippage and win. We can see exactly what content is converting and we can continue to make that a best practice. 

I’m going to go back and I’m going to say that the transparency within the platform, to be able to have a factual-driven conversation when sellers are out there getting beat up every day on the phone is important. It is important to identify that this isn’t an emotional thing, this is just a factual thing that we can get better at. When we’re looking at something that ties directly to revenue, there are interactions in Highspot that we can partner with marketing to share. This could be our click-through, our form fills, or our pitch styles with the content that we’re using, we compare directly interdepartmentally, just like we do to create training programs to then report back and see what the true contributors are to them. Having that level of insight when we obviously want more budget every year, we want to substantiate ourselves. We want to show how much we are contributing and are absolutely integral. 

SS: I love that. Jonathan, thank you so much for taking the time to meet with me today. I really appreciate it. 

JE: You’re very welcome. Thank you so much for having me. 

SS: Thank you for listening to this episode of the Win Win podcast. Be sure to tune in next time for more insights on how you can maximize enablement success with Highspot. 

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