Customer Success Selling Starts Here

How This Playbook Works — and Where We Begin

This post is part of a paired series. Each chapter of this Sales Reset Playbook accompanies a related chapter in Peter Button’s Sales Reset Briefing. You don’t need to read both, but the briefing is available as context if you’re interested in the deeper thinking behind this shift.

• Peter Button’s Sales Reset Briefing: Explores strategy and the big picture.

• Sales Reset Playbook: Is focused on practical recommendations from three vantage points:
  

  1. Individual Salesperson

  2. Frontline Sales Leader

  3. C-suite Senior Leader

This structure is intentional. Outcome-based selling cannot be achieved through one role alone. It requires joined-up thinking, clear accountability, and consistent reinforcement across the organisation.

We begin this chapter of the Sales Reset Playbook with a foundational shift in expectations:

1. For Individual Salespeople: Clarify What Success Looks Like

As an individual salesperson, you’re still accountable for revenue. That hasn’t changed. But something new is emerging — and it matters just as much.

You’re now increasingly accountable for helping the customer define success from their side of the transaction.

And this is not in vague terms. It’s not about defining outcomes regarding “improved performance” or “faster processes.” It's about defining outcomes in clear, specific, and meaningful terms to the customer, language they can confidently use to justify the investment internally.

🔧 Practical Moves:

• Start by reviewing your current and recent opportunities — wins, losses, and pipeline:

  • Go back over recent opportunities.

  • Look at emails, proposals, and CRM notes.

  • What, if anything, was discussed or written down about customer outcomes?

  • Did you and the customer agree on what success would look like?

  • Were those expectations made explicit and tested with a range of stakeholders?

  • If not, what’s missing?
    

• Ask outcome-oriented questions early:

  • “What outcomes do you need to achieve if this goes ahead?”

  • “How will your team know this was a worthwhile investment?”

  • “What would need to happen for this to feel like a success story six months from now?”
    

• Mirror the customer’s language:

  • Use their words — not yours — in your proposal or follow-up.

  • For example, it’s not “accelerate adoption” if they said “get everyone actually using it.”

  • Use their words to earn trust and drive internal alignment.

  • Use AI “Conversation Intelligence” and transcription tools to capture and repurpose transcripts with their unique words as follow-up emails and proposals.

2. For Sales Leaders: Coach for Clarity, Not Just Momentum

Your team’s job isn’t just to generate sales activity. Their task is to lead meaningful customer conversations. And one of the most consequential things a salesperson can do is help a customer define success before the purchase is completed.

But here’s the problem that doesn’t get coached in most sales cultures.

Managers ask about pipeline size, stage movement, and forecast risk. They rarely ask:

This question changes everything.

🔧 Practical Moves:

• Review how you run pipeline and opportunity reviews:

  • Build in a standard checkpoint: “Have we agreed on measurable customer outcomes?”

    Not just what they’re buying, but why they’re buying it — and how success will be judged.
    

• Use call recordings to coach for definition, not just delivery:

  • When listening back, look for missed moments to ask outcome-oriented questions or clarify expectations.

  • Focus primarily on the parts of the conversation where your team member could have asked follow-up questions to dig deeper about the outcomes they need.
    

• Model better proposals and summaries:

  • Write and share examples that reflect clearly defined outcomes.

  • Develop playbooks introducing a sufficiently wide range of available outcomes that customers might expect from using your products and services.

  • Help your salespeople see what “good” looks like in practice — and what feels vague, risky, or assumptive.

• Use structured role-play to build confidence and fluency:

  • Outcome-focused conversations don’t come naturally in most sales environments — they must be practised.

  • Run short, focused role-play sessions where salespeople try framing outcome questions, responding to vague answers, or reflecting customer language.

  • Make your role-plays safe, and do everything you can to make most of them thoroughly enjoyable and fun!
    

• Ensure the right range of stakeholders shape outcome expectations, not just “the principal contact”:

  • Salespeople should be expected to involve everyone who plays a material role in success.

  • Ideally, this should include end users, technical experts, implementation partners, and internal colleagues from delivery, product, or customer success.

  • Outcome definitions are stronger, more realistic, and more likely to hold when shaped by the people responsible for delivering and experiencing the results.

  • Encourage your team to go beyond the sponsor and involve the ecosystem.

3. For the C-Suite: Make Outcomes Part of the System

If you want your salespeople to define customer outcomes well, you must create conditions that make that possible and expected.

That means looking beyond the sales conversation itself and examining the systems, incentives, and expectations you’ve built around it.

Because here’s the reality:

In most B2B organisations, salespeople are rewarded for securing revenue, but not for defining what that revenue is supposed to achieve for customers.

🔧 Strategic Moves:

• Require outcome clarity at the point of purchase:

  • Add a new checkpoint to commercial governance or deal sign-off.

  • “Have the intended customer outcomes been clearly defined, in measurable terms?”
    

• Make it easy to document outcomes and make them visible across teams:

  • Build outcome fields into your CRM or handover templates.

  • Ensure that customer success, delivery, and product teams see what success was promised — and in whose words.
    

• Consider investing in AI-powered conversation intelligence tools:

  • These tools allow your teams to capture transcripts, surface patterns, and repurpose customer language into follow-ups and proposals.

  • More importantly, these tools can give sales leaders the evidence and visibility needed to coach for quality, not just quantity, of conversation.
    

• Back sales leaders in coaching for outcomes, not just volume:

  • Give them time, tooling, and permission to shift the focus.

  • If their only brief is to drive forecast accuracy, you won’t achieve and maintain your Sales Reset.
    

• Consider outcome alignment in compensation:

  • For some roles, explore linking a portion of variable pay to achieving agreed customer outcomes.

  • Even a small initial shift sends a strong message about what matters.
    

• Treat customer outcome focus as a strategic differentiator:

  • The ability to define, align around, and deliver customer outcomes is fast becoming a competitive advantage.

  • Build your operating rhythm around it.

Conclusion: A Small Shift That Changes Everything

In some ways, this isn’t a radical new methodology. It’s a subtle shift in accountability — but one with far-reaching implications.

When salespeople help customers define success clearly, they create better alignment, conversations, and outcomes — even before the purchase is completed.

But this can’t happen in isolation. Sales leaders need to coach for it. Senior executives need to support, resource, and measure it. All three roles—salesperson, leader, and C-suite—need to understand that outcome clarity at the point of sale is the starting point for everything that follows.

This is where your Sales Reset begins.