Why Current Solutions Don't Work For Sales Enablement

Now that you understand sales enablement as a discipline, who makes a great enablement team member, and what knowledge they should be supplying to their client-facing teams, we can finally talk more about the current sales enablement landscape. To understand why current solutions for sales enablement don't work, it's critical that we acknowledge the differing values of the knowledge consumer and subject matter expert (as we examined at the end of chapter 1). Since the jobs to be done for each of these roles are different, solutions need to incorporate both points of view in order to succeed and gain adoption. Whether you're talking about Wiki's, Q&A tools, enterprise search, emails, messaging, or even physical sales playbooks or binders, all existing solutions fail to do this, or optimize solely for one workflow. Due to this barrier for either the subject matter expert or consumer, content quickly becomes stale and distrust emerges. Ultimately, there is poor adoption for the solution or a very specific workflow is created that is inefficient for all parties. This theme is consistent across most of these solutions you may be using, but let's dive deeper into why current solutions don't work effectively for enabling your sales team.

Messaging Apps & Email Threads

As a small start-up, messaging and emails can be a very quick, easy, and cheap way to distribute content and knowledge out to your sales team. Since your whole team is on it, you can easily ping people with updated content and your reps can easily ask questions when they need to. Any one-off questions you are getting, while distracting, are manageable at this stage. You probably also have only a select few sales assets to work with, so reps are in the loop and trust that content is up to date. With dedicated email threads or channels in your messaging app you can keep conversations focused on a specific topic so that discussions happen in context and it's easy for reps to find that content later. While all of this is true, at some point the system will break. Either experts will be inundated with too many questions, reps will find that content is always stale, reps won't be able to even find the right content, or all of these things will happen in parallel. This is the point where most companies begin searching for a dedicated sales enablement solution.

Ironically, whether you are a small start-up with no dedicated sales enablement person, or an enterprise organization with an enablement team and multiple solutions in place, most of your reps will continue to resort back to email or messaging as their go-to way to get knowledge. Why is that? There are multiple reasons, but the simple answer is because we want responses to our questions in the fastest, easiest way possible for us. Going to another destination (app) to look for knowledge or ask a question feels like extra work to do. Since messaging and email are ingrained into our daily workflows, it's extremely easy to default back to what we are comfortable with while neglecting the burden it places on the resource answering the question (experts/subject matter experts). The real-time nature of chat forces experts to context-switch all the time, which causes drops in productivity. Worse yet, the one-off answers they are giving to individual people are not getting captured for your whole team. Instead, they are stuck in silos, leading to the same questions being asked over and over again.

Unconsciously or not, the "faster and easier" solution of email and messaging apps leads us to continually optimize for the benefit of question askers (knowledge seekers). This misalignment in value between the question asker and answerer is the central reason why most dedicated sales enablement solutions fail to be adopted by enterprise teams. Each solution has it's own unique deficiencies which we will now examine closer.

Document Storage

Documents are Like Digital Pollution.

Document storage refers to content repositories like Dropbox or Box. Many sales teams rely on document storage solutions to act as their de facto knowledge base when they are just starting out. They're cheap and everybody knows how to use them. However, they quickly outgrow their usefulness.

Documents are ideal for capturing content that doesn't change that much once it's written. But so much of your knowledge is changing everyday, so that means you are constantly updating documents to keep up. And that means trying to find all the places where we said that thing that we now want to change becomes a fool's errand. It also means you have to communicate the new change to everyone, and then you have to remember who you told about that new version. But then later when I open a document, how do I know if it is actually still right?

Compounding the problem, once you have more than a few of them, they become a mess. At least with paper you had to make an effort to copy it. Not so with documents and so you end up with a sea of similar but different versions of the same document all over the place. It's digital pollution. For your sales team, this can easily cause your team to be inconsistent in their messaging. Each rep is using a different "v6_final" version of your deck, which is driving you and marketing crazy.

Documents are too Slow for Instant Consumption

Documents are too long. The length of a document has a direct correlation to its usefulness. The longer a document is the less of a chance anyone will read it, and the higher the likelihood that it will get out of date. These days our expectations for brevity and accuracy have never been higher. We have information overload and expect just the right information without the noise.

Documents are at the core of a majority of the sales enablement solutions we identify as inadequate for modern sales teams. Whether it's physical sales playbooks, wiki's, enterprise search, or sales asset management solutions, they all rely on documents as the medium to consume knowledge. But in today's world, most documents are unable to solve for situations where reps need to instantly consume information, like when they are on a call or giving demos to prospects. In today's world, speed is key. Reps need to access information in as few clicks as possible, which is not fit for a document world. So what's the solution then? In the mobile world, small, easily consumable cards have emerged as a common design pattern which is now starting to become a wider trend across the web (a trend we explore in the next chapter).

Enterprise Q&A


Enterprise Q&A is often touted as a great sales enablement solution primarily because people think if you have one dedicated, noise-free location for all of your sales questions and answers it will become much easier for your reps to find this information. Additionally, with the ability for the whole rep team to see these answers, one-off shoulder taps and messages will decrease because your whole team has access to your Q&A tool. While great in theory, the way enterprise Q&A solutions mirror consumer Q&A sites leads to their downfall as a legitimate sales enablement solution.

No Individual Accountability Creates Slow Response Time

When you ask a question on a social Q&A site like Quora, generally you are searching for expertise that you do not have direct access to. You hope the answer comes in a reasonable amount of time, but there is no expectation of an instant, qualified response. Folks will respond to your question only if they feel compelled to. They are not individually responsible to respond, even if they have an appropriate answer. Contrast that to a typical Q&A scenario a sales rep might face. Take for example, a situation where a prospect raises a technical question that she does not know the answer to. The rep likely already has a good idea of the person/team who can answer this question and probably even has direct access to the expert (whether it's in person or via email/chat). Most importantly, she needs an acceptable answer in a reasonable amount of time.

The circumstances surrounding the two scenarios couldn't be any different. Yet, often times it's treated the same way by enterprise software. Enterprise Q&A solutions make questions available to the whole company to answer, in the hopes that more people = more (and better) answers. But the bystander effect tells us that the probability someone helps us is actually inversely proportional to the number of people present. We experience it all the time when we think (and assume) someone else will answer the question. Rarely is it done with bad intentions either. Most of the time it's because at the point in time we received the notification we were busy focused on something else. But since the question is addressed to a large group, instead of an individual there is no urgency. In fact, we reassure ourselves that someone else will shoulder the burden of answering the question.

Now, if that question was addressed specifically to one individual or a small, well-defined team of experts, the answerer's response is different. That question now becomes a defined task the answerer must complete vs. a mind reading game of "Who Answered It." A sense of urgency is created as the individual feels a responsibility to give an accurate and timely response. No one wants to be "that guy/gal."

Stale Content Leads to Distrust

Q&A software is great at providing answers at that specific moment someone asks their question. Yet your business' information potentially changes everyday. An answer given today on competitive positioning will certainly be different than the one given the next year, even the next month. When that information changes it would be great if our answers were automatically verified by experts on our team, but they aren't. Since there is no urgency or incentive for subject matter experts to update answers, content quickly becomes stale and unusable.

So when your rep is searching for how you position against X competitor in your Q&A software she may find what she is looking for. But, she noticed the response is 10 months old. Being the good rep that she is, she wants to make sure that answer is still the same today so she messages someone on the sales enablement team. She finds out that there are some new updates to the answer, so she takes what her enablement team says, crafts a thoughtful response, and sends it off to the prospect. Great outcome right? Well on the one hand, the rep found an answer, but she still needed to ask someone else to verify the information was still accurate. Even more troublesome, since her experience with the Q&A software did not solve her problem she now distrusts the solution. As a result, she is less inclined to search on your Q&A software again.

The crux of the problem lies in the fact that Q&A software optimizes for search not solve. You can very well find what you are looking for, but that does not mean it is still accurate. Since your problem remains unsolved, reps resort back to "faster and easier." This means more shoulder taps and one-off messages that lower the productivity of your experts. A cycle gets created as other reps experience the same problems. Experts receive even more shoulder taps and messages, leading to declining usage metrics on your Q&A software. Even worse, subject matter experts spend more time answering questions than creating new knowledge, lowering their productivity.



Ah, the trusted ole' wiki. Most people would point to Atlassian's recent IPO (parent company of the popular Confluence wiki software) and say that's all the proof you need to see why wikis are so successful. But much like Enterprise Q&A, Enterprise Wikis tend to mirror Wikipedia, which has an entirely different set of incentives that does not translate well into a sales team's objectives.


Wikis aren't where you work

After Google released their Knowledge graph in 2012, Wikipedia saw a 21% decline in page views the following year.


As you can see in the image above, Google now inserts relevant information regarding searches right into the search workflow, so users do not even have to click through to Wikipedia. With an estimated 1 in 4 searches utilizing the knowledge graph, Google is slowly providing information to users in context, which is contributing to the declining readership of Wikipedia. Super helpful because this valuable knowledge is now being brought to us without having to leave Google's search.

In the enterprise, this notion of contextual knowledge is just as important. As the success of the knowledge graph proves, while the Wiki may be the easiest way to create knowledge, it is not the easiest way to find and consume knowledge. When you think about a rep's workflow, they primarily live in their CRM, inbox, and then other necessary tools to do jobs like screen sharing, cold email, and prospecting. At work we use so many apps throughout our day that unless an app helps us do our job, we just aren't going to use it. It's out of sight, out of mind. So many wiki projects get rolled out at work and then are quickly forgotten about for this exact reason; a wiki or knowledge base should not be viewed as a destination, an app, a portal. Knowledge is a means to an end. The end is a job we need to get done, our knowledge base helps us get that job done.

Long Form Wiki Content Hard to Consume And Analyze Effectiveness

Wiki's are a classic example of subject matter experts not understanding or empathizing with how knowledge consumers will be able to consume the content when doing their job. Most wiki pages are one piece of long form content divided up into multiple sections to make it "easier" to browse. But in a situation where a rep is on the phone with a prospect it is incredibly difficult to find and reference something contained in a long-form wiki page in just a few seconds. Wiki's are great in situations like onboarding or ongoing training, where a rep can sit down and actually absorb the content they are reading. However, for the job of instant consumption, wiki's are not a viable solution for reps. As we will explore more in the next chapter, an ideal sales enablement solution is able to accommodate all of the various jobs a sales rep needs to do.

"Today, sales people don't have tools at their fingertips to help guide them through conversations and if they want to deliver content based on what they are hearing on the phone, they spend valuable time trying to find something credible to deliver to the buyer. This is a source of massive inefficiency and as a result, frustration on the part of the individual contributor." - Robert Koehler, TOPO Group Senior Analyst

The additional downside of long-form content like wiki's is that it's difficult to measure their effectiveness. Again, it goes back to the jobs your reps need to do. Wiki's are built for browsing so their analytics can easily tell you pages that were viewed most. That can give you insight into new training materials to create, as pages that are viewed most could be weak points in your enablement strategy. But wiki's aren't built for instant consumption, so their analytics aren't equipped to give you insight on how a rep used that content in selling situations. Your sales enablement solution needs to do both effectively.

Sales Asset Management Solutions

Used by Sales, But Built For Marketing

When we say "sales asset management" we mean solutions that take document storage a step further and allow you to manage and organize your sales assets, curate unique content portals to prospects, and track their engagement in granular detail. But sales enablement is much more than just the sales assets you present and send to prospects. It involves just as much internal knowledge on sales processes, objection handling, and product FAQ's, as it does on external content like your case studies and white papers. So, while some of these features are valuable, we believe these solutions are primarily built to solve marketing problems, not sales problems. Solutions in this category help to answer questions like:

  • Is the sales team using the content marketing creates?
  • Do prospects engage with the marketing content my team create?

But your sales leaders don't necessarily care about those same questions. What sales leaders are looking for is a fast, simple, and reliable way for reps to find accurate information. sales asset management solutions are focused on the jobs of marketers, but your sales enablement solution needs to focus on the jobs of your sales team. As the graphs below illustrate, marketing views sales enablement through their unique point of view. As such, they will believe the sales assets they create are enough to enable your sales team. But, anyone in sales knows this is a narrow view of sales enablement. In reality, internal knowledge comprises most of the content necessary to enable your sales team, and marketing created sales assets are just a small part of that sales playbook.


Engagement analytics lack correlation to tangible business outcomes

The impact of this narrow view on sales enablement is most clearly felt when looking at the lack of actionable business analytics a content storage or sales asset management solution provides. While they can tell you exactly how many seconds a prospect looked at a pricing slide in your deck and can claim to tell you how that piece of content lead to a closed deal, it still does not paint a clear picture. For example, the prospect may have been on that pricing slide for so long because they were confused by your pricing, calculating the cost based on their specific user count, or they just took a coffee break! Turns out, on the next call your sales rep expertly diffused an objection regarding the feature set in differently priced editions of your product, but your sales asset management solution won't track that.

In fact, many asset management solutions require your reps to do unnatural acts to track content performance like send the email through their service. That means they have to leave their workflow when following up with your prospects via email and find the appropriate piece of content so it can be tracked properly. As a result, you may not even be tracking content performance at all if your reps aren't adopting your asset management solution! Even more critically, these solutions are file based, which means only PDF's and slide decks can be tracked, not your links from more top-of-the-funnel content like blog posts, case studies on your website, or videos. In today's world, more and more of your marketing content actually lives on your website. Can you really gain insights into the effectiveness of your content if you are only accounting for such a small piece of the pie?

Sales asset management solutions totally miss intention (the why) and instead focus on the what (the specific slide), which leaves you with more questions than answers. What about some of these other questions: What sales knowledge; such as messaging, common objections, product, and security details has been used by reps to close deals? Where are the gaps in my enablement strategy? How can analyzing the sales knowledge my reps are using most be leveraged by our marketing team to create useful assets? All of these questions point to analytics that provide tangible metrics on business outcomes, something your sales asset management solution won't be able to provide.


The promise of enterprise search is you just point your enterprise search engine at all your existing content and voila, you have one place to search your entire enterprise for anything you need without doing any work. But turns out this promise is hard to keep as everyone has their own unique way of organizing and labeling content, which hampers the effectiveness of enterprise search platforms

Who's stuff are you looking for?

Finding "my" stuff is different than finding "other people's" stuff. There are many products today that do this well. You can hook in your Google Drive/Box/Dropbox/Evernote etc. do one search and get back your stuff wherever it may be. This can work well because the results you get back in the search will be familiar to you because you wrote it in the first place. You will see the 4-5 results you get back and probably think "yup that's the one" and open it. You probably don't need much context because you may have a consistent way you name files or folders. It is also a nice productivity solution on mobile, where apps like email clients are adding this as a feature. You can quickly "attach" a document from these other services without having to jump out of the app you are working in.

But if you are trying to search across a team's collective shared content it's different. You enter your search terms and get back a list of stuff. Who's stuff is this? What are these confusing file names? Am I in the right folder? You need context; whose information should I be looking at? How do I use this information I am finding? When was the last time a subject matter expert verified that this was accurate?. You end up opening a few of the search results, get frustrated and give up.

Static vs. Dynamic Information

Finding static information via enterprise search tends to work pretty well. For example searching an email archive. Those emails were already sent and will never change again. Contracts are another great example. If a contract ever changes there is a very clear legal process that gets followed to execute the change. This is why you see a lot of enterprise search vendors going after "eDiscovery" type use cases, where a company wants to quickly find content on a topic for a legal matter. You are searching history, and history doesn't change (we hope :)).

But totally different when you are searching for information that changes. Try searching for the latest powerpoint about your product, your search results usually look something this:

  • product_name_latest.ppt
  • product_name_latest_v7.ppt
  • product_name_latest_customer.ppt
  • product_name_latest_johns_edits.ppt
  • product_name_latest_master.ppt
  • product_name_latest_master_v3.ppt
  • product_name_latest_final_master.ppt

Madness! It's not intentional of course. People are busy and everyone uses their own conventions. But you will either (1) just pick one of these and go, and likely use something outdated or inaccurate, or (2) go ask someone for the 800th time where the latest deck is. It's not just a powerpoint problem it's an any file problem. You need more than just a file name and last modified date to know if it's the right thing.

Push vs. Pull

Search is and will continue to be a core mechanism to find what we need. It is the simplest interface that any of us can use, and allows us to "pull" in information when we need it.

But what about all the stuff we don't know to search for? Search is the path you take when you know you need to look for something, but in our work lives there is valuable new knowledge getting captured all the time. It is not reasonable to assume that we know everything available to us and how to search for it. So even with the best search in the world, there remains a big bucket of valuable information that we miss because we didn't even know to look for it.

This idea of push vs. pull is extremely important, one that we believe is driving the future of SaaS.

Now that we have demonstrated why current solutions aren't delivering enough value for your team, we are going to explain what requirements you should be looking for in an ideal sales enablement solution and the emerging trends in SaaS that are shaping these requirements.