Why Enterprise Sales Requires Deal Coaching to Succeed

Part of what makes Enterprise sales so complicated is the number of buying influences involved in the decision. Each buyer brings their viewpoint, exponentially growing the amount of information a seller needs to sort through, resulting in a longer sales cycle and often stalled sales opportunities.

“The level of knowledge needed to close an Enterprise sales deal is profoundly more complex than a transactional one.”

Complex, Enterprise sales deals require strategy and execution coaching (e.g., Deal Coaching) to move an opportunity forward. Skills and behavior coaching (e.g., Sales Coaching) alone is not enough to develop a winning game plan. Examining Sales Coaching and Deal Coaching through the lens of knowledge helps you understand why sellers need formal Deal Coaching to advance Enterprise sales deals.

The Complexity of Knowledge: A Closer Look

Massachusetts Institute of Technology’s (MIT) Knowledge Complexity Framework plots four levels of knowledge, from simple to complex.

  1. Explicit Knowledge: See and Study

    Explicit knowledge is the simplest form of knowledge. You can articulate it with little risk of misinterpretation, and it is universally understood. A good example of this is technical knowledge captured in a patent or blueprint. The knowledge can be easily accessed, shared, and grasped by seeing and studying it.

  1. Experiential Knowledge: Experience and Practice

    You cannot fully articulate Experiential knowledge. It requires learning through experience and practice. A good example in Enterprise sales would be learning a Customer Relationship Management (CRM) tool. Through continued use, you gain experiential knowledge.

  1. Endemic Knowledge: Study and Live

    Endemic knowledge is restricted to a specific area or place. To understand it intimately, you must study and live it first-hand in its contexts, such as management processes or sales practices.

  1. Existential Knowledge: Feel and Live

    The highest form of knowledge is Existential knowledge. It isn’t easy to express and articulate, like personal wisdom or intuition, and is context-dependent. An excellent example is a company’s sales culture, including the attitudes, values, and habits that characterize the sales team. You need to be part of the subculture to grasp the meaning truly.

Enterprise sales success is dependent on not only the acquisition of knowledge through Enterprise Sales Coaching and Training but, more importantly, on the application of knowledge through Enterprise Deal Coaching.

Enterprise Sales Coaching is General Knowledge About Past Events that Impacts Seller Behavior

 Enterprise Sales Coaching is gaining foundational knowledge through learning and role play. Enterprise Sales Coaching is often a one-on-one session between the seller and a coach or manager who is helping develop a seller’s sales skills and behaviors by teaching best practices and providing constructive feedback, including:

  • Gathering research and information about the prospect before the first call
  • Having a discovery call before presenting a solution
  • Listening carefully
  • Asking questions to gain clarity on the prospect’s problems and objectives
  • Reviewing calls and discussing what went well and what needed improvement
  • Reviewing remote selling techniques
  • Reviewing email conversations with prospects throughout the buyer’s journey

These best practices apply to all Enterprise sales professionals, therefore can be considered Explicit knowledge and sits at the bottom of the knowledge ladder.

Sales coaching encourages Enterprise sales reps to embrace the following behaviors:

  • Naturally curiosity
  • Problem solver
  • Good at building relationships
  • Know how to lose fast
  • Excel at time management
  • Good at storytelling

We learn these behavioral traits through experience and practice. These traits may differ from company to company, so being aware of an Enterprise sales organization’s norms are essential to understanding which traits are highly encouraged. In this sense, behavioral traits sit higher in the ladder of knowledge and fall within Experiential knowledge.

Enterprise sales coaching is more about simple and experimental knowledge or tactics. In Enterprise Sales Coaching, managers review past events, recommend corrective action regarding a seller’s skills and behavior, and reinforce good behavior to help advance a seller’s skill set. In contrast, Enterprise Deal Coaching is more about endemic and existential knowledge or deal strategy. Enterprise Deal Coaching helps sellers develop a strategy and execute a plan to advance a seller’s position with the buying team to win a deal.

Enterprise Deal Coaching is Complex Knowledge About Future Events that Impacts Deal Health

 Deal Coaching, an emerging category within the Sales Technology space, is about Enterprise deal strategy and execution. Deal Coaching includes one-on-one sessions between the Enterprise sales rep and a coach/ manager or one-to-many sessions between the seller and a pursuit team. The goal of these sessions is to devise a strategy and action plan to win a current Enterprise deal.

The knowledge involved with Deal Strategy and Deal Execution can be the most complicated because it is both tacit (knowledge that is difficult to express or extract) and contextual within the sales organization. The Enterprise sales rep takes into consideration the following complex knowledge to formulate a strategy to win:

  • Customer Dynamics
  • Buying Process
  • Problem Awareness
  • Solution Definition
  • Competitive Landscape
  • Pricing
  • And more

The sellers must embrace the sales culture to use their Existential knowledge and reach the highest point on the ladder. The more complex the learning, the more tailored the coaching needs to be. Complex Enterprise sales knowledge cannot be replaced by Artificial Intelligence (AI). It requires human interaction and interpretation hence why Enterprise sales require Deal Coaching to succeed.

Enterprise Deal Coaching looks at a specific deal and specific knowledge to develop a specific plan.

Strategy and Execution Coaching are Often the Forgotten Parts of Enterprise Sales Coaching

Enterprise Sales Coaching and Deal Coaching are complementary and essential to successful enterprise selling. Together, they form the integral 4-part approach to coaching sellers: skills, behavior, strategy, and execution coaching. The latter two, Strategy and Execution coaching, can have a more immediate impact on Enterprise sales quota attainment and are critical to Enterprise sales success. For Deal Coaching to be effective, Enterprise sales teams need to embrace a framework across the organization and encourage consistent coaching.

The challenge many Enterprise sales leaders face is how to scale Enterprise sales coaching and deal coaching across their sales organization. There are several software tools you can use to improve sales coaching. Conversation intelligence software provides a view into sellers’ interactions, making it easier to identify and replicate your best sellers’ actions and review their sellers’ conversations with prospects and customers.

Today, Deal Coaching within Enterprise sales organizations is mainly supported using document-based tools. To improve and scale Enterprise Deal Coaching, organizations need to move away from documents and spreadsheets and leverage cloud-based sales software solutions that complement CRM and help Enterprise sales teams simplify and leverage complex knowledge to win deals:

  • Visualize Enterprise deal health
    Is the Enterprise sales deal legitimate, and how well is the seller positioned with the buyers?
  • Shape how sellers approach Enterprise deal pursuit
    Repeatable Enterprise sales process for assessing deal health and identifying gaps
  • Guide how Enterprise sales managers approach 1-on-1 deal coaching sessions
    At a glance, understand the status, strategy, and tactics as part of the sellers deal pursuit
  • Capture and reuse institutional knowledge
    An algorithmic approach to using historical data
  • Enable remote Enterprise sales collaboration
    Facilitate team-selling and internal collaboration for defining deal strategy and action plans

Is your Enterprise deal pursuit team hanging on to old-school methods? It is time to evolve document and spreadsheet-based methodologies. Fuel the future of Enterprise selling with purpose-built Deal Coaching software that provides a simple, repeatable Enterprise sales process to break down complex knowledge and gain clarity on the strategic next steps to advance Enterprise sales deals.


  1. Massachusetts Institute of Technology, “The Tyranny of Distance.” All rights reserved.
  2. Outreach, “The Art and Science of Selling: Insights from our Summits
  3. VantagePoint Performance, “The Art and Science of Selling
  4. Hubspot, “Sales Culture: The Ultimate Guide