As a strategic Go-to-Market (GTM) team partner, enablement helps ensure that GTM teams receive the learning and resources they need to do their jobs effectively, while minimizing their time spent on non-revenue generating activities.

Finding the right balance between the two can be difficult to navigate with both leadership, as well as cross-functional teams in any organization. 

To try to find the right balance, enablement teams should consider creating an enablement calendar to support the GTM team’s learning journey.

An enablement calendar captures and communicates key upcoming enablement moments based on business priorities, upcoming initiatives, field capacity and cognitive load, as well as enablement team bandwidth.

Putting a calendar in place can provide benefits to GTM leadership, the field, and cross-functional partners as it:

  • Reduces GTM team randomization
  • Helps set expectations
  • Ensures learning is focused on top priorities
  • Provides visibility to help teams plan their time

Additionally, enablement teams can benefit from a calendar by transitioning from a reactive enablement approach, to proactive one, ensuring:

  • Their efforts are aligned to company priorities
  • They're building connected programs versus tackling a series of one-off trainings
  • They have a framework to aid prioritization when new ideas or business needs arise.

With the benefits in mind, how do you get started?

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Step #1: Determine a planning cadence

The first step to establish a calendar is to determine a planning cadence that fits the maturity of the business. There is a baseline level of maturity required for a calendar to be useful for an organization, but if a team is experiencing the inverse of some of the aforementioned benefits, then it might be worth exploring. 

At hypergrowth SaaS companies, I have had most success with a quarterly calendar, but when times are particularly turbulent with frequently changing priorities and leadership misalignment, a monthly cadence has been a better fit.

As a general rule of thumb, more mature organizations can handle more forward looking enablement calendars. 

Step #2: Calendar structure

Once the cadence is set, it is time to consider the calendar’s structure. The size and focus of an enablement team will play a key role in this decision, as well as the design of the GTM organization. 

In the past, with a well resourced enablement team and enablement managers aligned to each GTM role, I have seen separate calendars created for each GTM role.

If an enablement team is a bit smaller, as many teams are, a single calendar is a great way to start. One might also consider a single calendar if they are providing enablement on a standard set of topics across a variety of GTM teams.

It is important to note that the term “calendar” can be a bit misleading, as it doesn’t necessarily mean a day-by-day view. It's possible to pick any altitude that aligns to an organization’s maturity and business needs. 

In the past, I've created a weekly calendar for the quarter. Below you can see an example in slide format, as I have found it best for executive alignment, but project management tools also work great and are best for driving enablement team actions.

In this calendar, I would note:

  • The name of the initiative
  • The expected training date, if applicable
  • Time requirement, if known, within each week.

In the example below, I've also included sections to highlight enablement specific to those two segments - this can also be done with color-coding, or be left off completely if it's not applicable.

Pro-tip: Not EVERYTHING enablement delivers to the field needs to live on the calendar.

Consider focusing on highest priorities, top level initiatives, or moments with concrete dates/time requirements.

Step #3: Cross-functional partner inputs

Once the calendar’s structure is in place, it is time to collect cross-functional partner inputs to understand their planned initiatives that will have an impact on GTM teams within the calendar’s time frame.

It's important to remember that this step is not about surveying every group to see what they would like enanblement’s help on, but is about ensuring your enablement team is aware of any upcoming changes in order to properly align on enablement’s focus with the GTM leadership team. 

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Step #4: Review calendar with GTM leadership

Once all the initiatives have been noted on the calendar, it is time to review the calendar with GTM leadership.

This is when enablement can help GTM leadership understand how much of the GTM team’s time is expected to be spent on enablement, based on current plans.

Then, enablement can help GTM leadership conduct prioritization exercises to ensure the calendar is manageable - for both the field and enablement capacity.

When applicable, pull cross-functional partners into these conversations so they can have visibility on prioritization decisions, and understand the impacts to their programs. 

Step #5: Share the calendar

Next, it is time to share the calendar. The calendar can either be kept private to the leadership team or shared across GTM teams. This decision should depend on the maturity of the organization and the enablement team’s perceived ability to commit to the plans in place.

If you're anticipating that the plans may frequently change, it might be best to keep the calendar with leadership only, to avoid confusion among GTM teams. 

Step #6: Keep the calendar up to date

Regardless of the audience, it is important to keep the calendar up to date!

When a new request for enablement or a business priority arises, it's important to consider it in the context of the calendar.

This is a great time to revisit the prioritization exercise with GTM leadership, and if adjustments need to be made, move plans accordingly to meet the needs of the business. 

A final pro-tip: It's important that enablement is not perceived as a gatekeeper or a blocker in the organization as a result of this process.

The calendar should help foster healthy communication surrounding the business’s priorities and the enablement team's bandwidth.

Ultimately the calendar reflects the decisions of GTM leadership, and misalignment should be addressed primarily with the GTM leadership decision makers, with the support of enablement.

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