Team of one: challenges brainstorm

Each month, a squad of Enablers meet up to discuss the specific challenges that they face in their roles. The unique thing about this monthly squad meeting: the attendees are all a Team of One. This means that they are the one and only person in an Enablement function at their organizations. 

In an effort to spread knowledge in the Enablement space, we wanted to distribute this group’s insights, best practices, struggles, etc. with the community. We hope that these resonate for others and that the learnings can be applied to their roles.


During February’s Team of One meeting, the group discussed three common challenges that they face when working with internal stakeholders. You can review the three unique challenges and some of the suggestions from the group below.

Revenue leaders embracing training without reinforcement

As a part of the job, Enablement professionals are tapped on the shoulder to put together training, onboarding, and coaching programs. The goal of these programs is to uplevel their organization; however, without reinforcement from Revenue leaders, the efforts can fall flat.

When this happens, our Team of One squad suggests:

  • Enablement Charter

    • Have an Enablement Charter to hold stakeholders (including Enablement) accountable for roles and responsibilities

    • Anchor activities back to the Charter document

    • Socialize the Charter often so that the team is aligned and aware of expectations

    • Update the Charter frequently as business/team needs change

  • Planning & Development

    • Involve front-line managers early in the planning and design process, then send weekly updates in an email about the status of involvement 

    • Pull leaders together on a call to define and align around priorities, KPIs, and desired outcomes

    • When designing the training, outline the specific reinforcement activities so that it sticks with these leaders

  • Collaboration

    • Leverage your champion leaders to influence others to embrace enablement

    • Develop relationships with Revenue leaders and set quarterly goals for both parties

  • Data & Impact

    • Lean on what the data is telling you

    • Example: If one team has embraced a training designed around negotiations and their win rate has increased over the last quarter, but another team hasn’t embraced the training and their win rate is stagnant, then showcase this to the Revenue leaders who need to reinforce Enablement’s efforts

The delicate balance of having “influence,” but not “authority”

Enablement professionals are put in a unique position. They’re able to influence a Revenue organization; however, they don’t necessarily have the authority that comes with a title like Sales Manager, Director of Sales, or VP of Revenue. Enablers can develop initiatives, but they aren’t able to hold the intended audience accountable for actually engaging with the content. 

When this happens, our Team of One squad suggests:

  • Relationships

    • Identify advocates within the organization who can support you

    • Develop strong relationships with Revenue leaders so that they’re inclined to reinforce Enablement’s efforts and remind their team members to complete the specific activities

    • Grow relationships with individual contributors so that they’re more inclined to take part in the specific activity

  • Authoritative Identification

    • Find where authority sits within the Revenue organization and set clear goals with the individual(s) to help drive the point home

“We need training for _________!” but in reality, they need something else

All too often, Enablement professionals are approached by Revenue leaders as well as customer-facing individual contributors who say, “We need training for ________!” You can fill in the blank with any skill: elevator pitches, pipeline management, product features, consultative selling, objection handling, etc. 

These off-the-cuff remarks typically happen informally and are supported only by anecdotal evidence. The reality: The team actually needs training on something else entirely based off quantitative data and qualitative feedback.

When this happens, our Team of One squad suggests:

  • Data, data, data

    • Anecdotal evidence only gets you so far and teams must leverage the data at their fingertips to focus on the desired outcomes

    • Measure the data before and after the training so that you can show Revenue leaders the impact that you were able to drive

    • Introduce the Sales Velocity formula and use buckets to define where the impact will be when creating trainings

  • In-Take Request Form

    • Use a ticketing system and ask people to support their request with specific data points as to why they need the training

    • Use the system to prioritize needs accordingly and align with internal stakeholders 

  • Teamwork = Dream Work

    • Set up listening circles, send out surveys, and/or create feedback loops so that you know whether or not your efforts are landing the way they’re supposed to with the audience

    • Agree with Revenue leaders on a quarterly basis on what needs to be addressed - don’t be rigid with these programs and leave some flexibility as needs change or more urgent issues arise


If you found these techniques insightful and you’d like to be a part of this monthly squad discussion, then find us on the #02-team-of-one-enablement Slack channel via The Enablement Squad. Ask to join the meetings and we’ll shoot a calendar invite your way!

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