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When leaders request new training, Clay's enablement team forces clarity by asking for the single behavioral change they want to see. This question filters out low-value requests and focuses initiatives on measurable outcomes. If the answer is "nothing," the training is likely unnecessary.

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When different departments push their own projects onto the sales team, reps get overloaded. To solve this, enablement leaders must shift the focus of every initiative away from departmental priorities and toward a shared customer outcome. This unified goal minimizes internal friction and clarifies what's truly important.

Before trying to persuade people, identify the overlap between the necessary changes ('what's required') and what your team already wants to improve ('what's desired'). By starting in this intersection, you tap into latent motivation, creating immediate momentum without having to overcome resistance first.

Don't just ask executives what they want to achieve, as this puts them on the spot. Instead, proactively formulate a hypothesis about their goals and challenges. Presenting this gives them a concrete starting point to react to, confirm, or correct, leading to much faster alignment.

When an employee presents a problem they should be able to solve, resist providing a solution. Instead, return ownership by asking, "What do you think you should do about that?" This simple question forces critical thinking and breaks the team's dependency on you for answers.

Effective upskilling isn't about random training. Leaders must first identify the new capabilities the business needs (e.g., AI-driven marketing). Only then should they assess which current team members have the desire and aptitude to learn and implement those new skills, creating a clear path for growth.

Instead of aiming for vague outcomes like "empowerment," start by defining the specific, observable behaviors you want to see. For example, what does "being data-driven" actually look like day-to-day? This focus allows you to diagnose and remove concrete barriers related to competency, accessibility, or social reinforcement.

To get internal buy-in for new tools or processes, tailor your pitch to the audience's altitude. Front-line reps care about the "Do It" (how it helps them execute tasks). Leadership cares about the "Know It" (visibility and data for decision-making). Matching your message to their needs increases adoption.

Sales processes become bloated over time, killing rep productivity. Instead of asking what to add, leaders should constantly ask what can be removed to achieve the same outcome. The best way to identify this friction is to be a rep for a day and experience the workflow firsthand.

Instead of telling a leader what they're doing wrong, ask what impact they want to have. By comparing their desired outcome (e.g., 'I want my team to bring me new ideas') with the actual result (e.g., 'no one speaks up'), the leader is intrinsically motivated to identify and correct the behaviors causing the gap.

Instead of forcing top salespeople into team-wide training, let them opt out. A leader's primary job with elite performers is to remove obstacles by providing resources like an assistant or better software. Don't waste their time or yours; just get out of their way.

Prioritize Leadership Requests by Asking: "What's One Thing Reps Should Do Differently?" | RiffOn