Published by Calendly - December 1, 2016

The sales enablement mistakes you’re probably making — and how to fix them

Ensuring reps have the tools and collateral they need to close is hard — especially for leaders in high-growth companies, where the process, positioning, and product itself are always changing.

“Today’s buyers are smarter than ever — most have completed over 65% of the buyer’s journey before they ever get on the phone with a rep,” says Steve Mayernick, Guru’s Product Marketing Lead.

And because buyers — especially buyers in SaaS — can come to the table with such a high level of awareness, reps must be better prepared than ever to dynamically assess and steer sales conversations.

Last month, we chatted with Steve about the most common mistakes sales leaders make when getting started with sales enablement, especially in high-growth companies where the process, positioning, and often the product itself are constantly changing.

Here, we’ve recapped those top mistakes and outlined what sales leaders can do to fix them.


  1. Leaders make reps work too hard to use the system. Every minute your reps spend digging through folders to find collateral, or emailing back and forth to find time with a prospect, is a minute they couldn’t spend selling. So look for sales tools that can live directly in their workflows.
  2. Leaders wait too long to focus on sales enablement. In the early days, sharing information with reps by word-of-mouth may be enough. But once leaders can no longer listen in on every single sales call, it’s time to build out a real strategy.
  3. Leaders try to switch to a better sales enablement system too quickly. Changing a person’s well-formed habits is no easy task, so exercise caution before investing time and resources in a platform that may not work for your team. Bring a few senior reps on board, get them used to the new system, and gradually expand the scope.
  4. Leaders aren’t sure how to measure sales enablement success. Sales enablement is amorphous and qualitative by nature, making it very difficult to measure. To improve sales enablement within your org, start with one place in the sales cycle where reps are struggling, and find a way to establish a quantitative baseline.


Prior to Guru, Steve was with RJ Metrics, where sales information “lived in a Q&A tool, in Google Docs, in a chat tool…it was just everywhere,” he said. “So before we fixed that, no one really knew where to get the most up-to-date information.”

And the more your reps must constantly dig through multiple platforms or folders to find competitor info and collateral, the less time they have to actually sell.


Look for sales tools that live directly in your reps’ workflow — for example, browser extensions they can pull information from while prospecting on LinkedIn, or — like Calendly — something they can pop directly into an email to minimize low-value communication.

The benefits here are twofold: tools that live in reps’ workflows reduce the amount of non-selling work reps must focus on, while also increasing their chances of actually adopting and seeing success with the tool(s).


In the early days, when leaders can overhear every sales call and offer 1:1 feedback, sharing information by word-of-mouth may be sufficient.

But once the team expands beyond a handful of people, productivity and call quality will suffer without the proper tools and an easy-to-access repository of information.

“You should start building an enablement strategy as soon as you can’t listen in on every call,” says Steve. “Messaging consistency and information shared across each call is crucial.”



As soon as possible, identify the bright spots in your team’s process, as well as the areas that need improvement. Answer questions like:

  • Who are your most productive reps?
  • What tools are they using that help them work faster/more intelligently?
  • What are they saying on calls that’s so effective?
  • Have they found a way to structure demos or overcome objections in a way the rest of the team could learn from?
  • How are they positioning your product against competitors?
  • Is there a particular customer segment they’re seeing the greatest success with?

And finally: what of all this can be replicated or standardized across the rest of the team?


If your team is used to pulling competitive intelligence or collateral from an unwieldy spreadsheet or web of folders, it’s probably time to switch to a smarter system — but with caution.

“Your reps are all different, and all have very particular ways of consuming information,” says Steve. “so you don’t want to invest a bunch of time and money in a system that may not work for them.”


The key to improvement is to start small: pilot a new solution with your most senior reps, get them accustomed to using that new solution in a particular workflow, and gradually expand to the rest of the team.

This could mean adding a simple Calendly link to the email templates your reps send to prospects, or using Guru to store just one type of sales information, like competitive intelligence or one-sheets.

“Any obstacle or change in a rep’s workflow will be met with some resistance,” says Steve. “So get your team used to using a new tool for one very specific purpose, and they’ll start to associate it with that workflow. When you expand the scope, it’ll be a lot easier for reps to transition to using it in their entire process.”



“Sales enablement is amorphous and qualitative by nature, making it very difficult to measure,” says Steve. “There are so many things that go into whether or not a rep closes a deal.”


To improve sales enablement within your org, start with one place in the sales cycle where reps are struggling, and find a way to establish a quantitative baseline.

“Let’s say your team is struggling with competitive intelligence,” says Steve. “That’s qualitative information, but you can look at development reps’ handoff rates as a quantitative metric.”

At RJ Metrics, Steve accomplished this by creating Salesforce fields for reps to indicate whether or not a prospect brought up various competitors on a call.

“Once we knew how often this was something reps were dealing with, we could measure how successfully they navigated those conversations,” he said. “Then, we could work on streamlining the way they consumed competitive intelligence information, and see incremental changes in their win rates.”

Steve also recommends using occasional tests or quizzes to identify information gaps that might exist across your organization.

“Reps are all different, and their knowledge is going to be all different,” he says. “Using tests or quizzes can help you find trends in sales knowledge you might not have seen otherwise.”


Sales enablement isn’t easy, and it’s never finished. The best leaders constantly tweak and optimize their efforts over time.

But by choosing tools that complement your reps’ workflows, thinking early about building a strategy, making changes with caution and finding a way to quantify each aspect, you’ll put your team far ahead of competitors who still rely on email threads and clunky spreadsheets.

One response to “The sales enablement mistakes you’re probably making — and how to fix them”

  1. Michele Lagala says:

    I would like to start on Facebook.
    When would you like to start Tuesday at 1:15 p.m.

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