Industry Leaders Agree: Successful Sales Enablement Focuses On Conversations, Not Content

Last verified May 20, 2021

When it comes to empowering salespeople to close deals and drive revenue, too many sales enablement solutions fall short by placing the emphasis on content rather than conversations. While content like case studies, product one-sheets, and white papers absolutely have a place in advancing the sales process, that place is to reinforce existing conversations. Sending a white paper to a prospect without context isn’t going to close a deal. But sending a white paper to a prospect can enhance an ongoing conversation.

At Guru, we believe that great conversations are what drive the sales process forward, and that empowering reps to have better conversations is the best way to help them succeed. We’ve heard from several sales enablement leaders that the key to sales enablement is helping reps communicate more effectively, not pushing content. Here’s what five sales enablement professionals have to say about prioritizing conversations over content:


Mike Garber, Sales Enablement Manager at InVision, says that it’s important to note that content is a key cornerstone in sales enablement. Companies have to have good content that their sales reps can use during the sales process.

“The reason conversations trump content is that the conversation has to come first.

When we chatted with Mike about sales enablement, he gave us the following example: “Imagine you have a job handing out fliers. You’re standing on a corner, just handing people fliers all day. You’re giving them content and the information on that flier might be really great, but you’re not giving them any context. You’re not having a conversation with them that can actually change their behavior, or give them insight into a need to change their behavior. What happens with that flier is that it usually ends up, unfortunately, on the ground, or more fortunately, it might make it into the trash can.”

According to Mike, the trash can is where content ends up when it’s sent to prospects without first having established a foundation through conversation. Reps should send good follow-up content after they’ve had a discovery call, but if there is no conversation that makes the content relevant, then prospects will delete the email. The content becomes irrelevant if the conversation doesn’t succeed.

So how can we empower reps to have better conversations?

Mike finds a lot of value in telling stories: “The ability to have a good conversation is dependent on being able to listen and tell stories that resonate. Stories that bring the right amount of logic and emotion into play so that prospects and customers don’t feel threatened by the information that you’re giving them.”

“If you think back to the old trope of what a salesperson is, you may think of a used car salesman or a door-to-door salesman. Those pushy salespeople who do not inspire trust and make you want to walk off the lot or shut your front door. And the reason those particular images don’t resonate with consumers is because those salespeople don’t have conversations. They don’t learn about what their prospects’ needs are. They know their products and they know their features, and they just feature dump.” – Mike Garber, InVision

Instead, salespeople need to create narratives with prospects around why they should have a conversation in the first place. What can your company or product do that makes a difference in the prospect’s life? When reps are empowered to have those conversations, it gives them the tools and knowledge they need to be confident with whichever direction the conversation goes. Customers are a lot more savvy these days. They have a lot of information at their disposal to make informed decisions, so salespeople need to be prepared to answer tougher questions.


At Drift, a conversational marketing platform, conversation is king. Kyle Bastien, Director of Sales Enablement, recently spoke alongside reps from Guru in a webinar entitled Sales Empowerment: Conversations That Matter. According to Kyle, the quantity of high-quality conversations people have within an organization is the most important thing to his team, so they prioritize driving great conversations through their enablement efforts at Drift.

“The best sales reps that I’ve ever seen or known are the ones that have the most real, authentic conversations. They don’t sound like someone doing an impersonation of a salesperson, and they don’t sound like they’re delivering a script. Enablement has changed from a collection of services that you might have gotten from a trainer or from product marketing to a centralized discipline that is focused – rightfully so – on coaching and enabling quality conversations.” – Kyle Bastien, Drift

One of the biggest reasons that being able to have great conversations is such a vital skill for salespeople is because buyers today typically tend to be further along in the buying cycle before they’re willing to engage with sales. People are far more well-informed about products and the product landscape, and there’s a seemingly unlimited supply in the market. Kyle says that prospects want conversations on their own terms, so the only way for a salesperson to really differentiate is by teaching.

“I’ve heard that helping is new selling, but I think it’s more accurate to say that teaching is the new selling. If you can help someone see things differently, or get them on board with a new way of how they do business, or educate them on the market landscape, that’s different. Teaching might be one of only ways to differentiate when it comes to the sales cycle,” said Kyle.

Training reps to have conversation- and teaching-first mentalities necessarily transcends a content-centric approach. Prospects have a better understanding of what they need, so reps need to be able to have dynamic discussions that meet them at their level of understanding, wherever that may be.


Roz Greenfield, Chief Enablement Officer at Level213 and former Head of Global Engagement at Optimizely has spoken at length about the value of prioritizing conversations over content. In a webinar with Guru, she explained that being empowered to speak to any number of topics is key. “Sales is evolving, because the customer journey is an infinity loop. Customers today expect anyone they interact with during their customer journey, both pre- and post- sales be able to provide the same level of service and knowledge. They don’t really care what the person at your company’s title is or if they sit pre-sales or post-sales. They expect everyone to be able to give them what they need when they need it, with the same level of service and expertise.”

Focusing too heavily on content doesn’t equip sales teams to have those conversations. Reps need the sort of training that helps them communicate more effectively and be better positioned to answer questions from better-informed consumers.

Roz also shared an analogy for how to think about the role of sales enablement:

“I see enablement roles as museum curators: When you go to a museum, you have your artist who created the actual work, and the curator who strung it all together and fleshed out the backstory in a way that makes sense for the museum visitors.”

A curator doesn’t just throw art at museum visitors, they tell a story about the art in a way that makes it easy to digest. They start a conversation. Putting art up on the walls with no context or backstory is the same as sending prospects content with no conversation.


As a knowledge management solution, we at Guru have always believed that it takes more than just content to empower reps to delight customers and drive revenue. Content is only a small subset of the knowledge reps need to have on hand to successfully engage with prospects. Arming them with PDFs and data sheets alone doesn’t ensure that they’re able to speak to every facet of the business that they’ll need to.

Steve Mayernick, Guru’s Head of Product Marketing and Revenue Empowerment, says that an emphasis on content has caused sales enablement to lose its way.

“While external content like your case studies and white papers still have their place, enablement solutions that focus too heavily on those assets only solve marketing problems, not sales problems. They help answer questions like “Is the sales team using the content marketing creates?” and “Do prospects engage with the content marketing creates?” Answers to these questions don’t help reps generate revenue. Period. Sales enablement is much more than just the sales assets you present and send to prospects. Those do nothing to help drive the real-time conversations that close business in today’s world.” – Steve Mayernick, Guru

Reps need to be empowered to handle objections live, have security expertise, and be able to move conversations forward by being consultative on products, markets, and buyers. Is there a place to send one sheets or PDFs to prospects before or after these conversations? Of course. But according to Steve, the future of sales enablement is empowering sellers to have valuable, real-time conversations.

Steve agrees with Kyle and Mike in that consumers being better-informed buyers has created a shift in the way we think about sales enablement. With the rise in chatbots and conversational marketing platforms like Drift, there is an emphasis on conversations being more real-time and dynamic than ever. Gone are the days of static conversations where sales teams could be reactive and succeed. Steve says that when we look at the sales enablement mindset that focuses on content and assets, it becomes clear that that mindset and the tools that go with it and were built for the sales landscape of 5-8 years ago.


When it comes to empowering reps to have better interactions with prospects, Bridge General Practice Manager Emily Foote believes that the conversation needs to start internally. “Conversation, to me, is at the heart of everything. Even coaching reps. Constantly building connections internally to help salespeople learn to improve their craft” is the first step, according to Emily.

What role does coaching play in the debate between content and conversations? By coaching reps rather than simply training them, sales enablement leaders give them all the tools they need to have those valuable conversations.

Emily cited a study that found that sales reps forget 42% of what they’re trained on within 20 mins, and 80% within 30 days. Episodic training is quickly forgotten. To combat this, she counsels create a culture of continuous coaching and learning, which empowers reps to build upon what they’ve been taught in real time during interactions with prospects.

Rethinking your approach to sales enablement

It’s become clear that sales is more conversation-driven than ever. There’s a whole market for conversation intelligence tools like Gong and Chorus that exist specifically to help revenue teams have better conversations, so it’s crucial to focus sales enablement efforts on that same goal. Teaching sales reps to rely on content to close deals does not position them to compete against best-in-class sales teams that prioritize conversations. A shift in perspective and priorities for sales enablement can result in confident sales reps who are empowered to have valuable conversations that drive revenue.