Brett Keirstead on Sales Coaching, Curiosity, and Human Judgment

Episode 43 · Brett Keirstead, Chief Sales Officer at Chief Outsiders

Published · 39m 13s

About Brett Keirstead

Brett Keirstead is Chief Sales Officer with Chief Outsiders and a lifelong sales leader whose career spans BDR, SDR, account management, and CRO roles. He is the author of We're All Salespeople and focuses on scenario-based coaching that helps sales professionals strengthen judgment, curiosity, business acumen, and accountability.

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Episode Notes

Key moments from this episode

Brett Keirstead joins Tailwind to make the case for sales as a demanding profession built on value, judgment, and continual practice. Drawing on a career that spans BDR, SDR, account management, and CRO roles, Brett explains why sellers must believe in the problems they solve before technique can help, and why leaders should coach through realistic scenarios instead of teaching canned responses. He explores how curiosity develops business acumen, why personal accountability separates reasons from excuses, and where AI belongs as a productivity and coaching aid without replacing human thought. The conversation closes with a practical leadership model: reinforce fundamental skills through regular practice, use a small set of conversational KPIs that support real decisions, and tailor qualitative coaching to the individual seller.

Takeaways

  • Start coaching with the seller’s belief in the value they provide; technique is unlikely to survive pressure when that conviction is missing.
  • Use realistic scenarios to expose how a salesperson thinks, then coach the judgment behind the response instead of supplying another memorized script.
  • Develop curiosity and business acumen together by asking better questions about how the customer makes money and how the proposed solution affects the business.
  • Build personal accountability into deal reviews by separating genuine constraints from excuses and asking what the seller could have influenced differently.
  • Protect regular skills practice and focus measurement on two to four conversational KPIs that help leaders make decisions, leaving room for individualized qualitative coaching.

Key Moments

  1. 3:06

    Treat sales as a profession that creates value

    Brett frames professional selling as the responsibility to bring a useful solution to a real problem and to keep developing the craft throughout a career.

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  2. 5:25

    Build belief before adding technique

    A seller who cannot explain the value and distinctiveness of the work will struggle under pressure, so belief becomes the foundation for later training and objection handling.

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  3. 8:58

    Coach judgment through realistic scenarios

    Scenario-based practice reveals the reasoning behind a response and helps sellers build authentic judgment instead of reciting the same memorized answer as everyone else.

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  4. 16:10

    Turn curiosity into business acumen

    Better questions help sellers understand how customers operate, connect solutions to business impact, and develop the commercial perspective required for future leadership roles.

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  5. 23:24

    Separate reasons from excuses in deal reviews

    Top performers take personal accountability for what they can influence, examine lost deals without self-punishment, and use the review to identify better future choices.

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  6. 29:42

    Simplify measurement with conversational KPIs

    Two to four memorable metrics can keep teams informed and support real decisions while leaders preserve time for practice and coaching tailored to each seller.

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Questions answered in this episode

How should sales leaders coach people beyond memorized scripts?

Put sellers into realistic situations, ask them to explain what they would do, and coach the reasoning behind the answer. Scenario practice helps the rep internalize judgment and adapt authentically when a customer says something unexpected instead of waiting for a canned response.

Why are curiosity and business acumen important for salespeople?

Curiosity shifts the seller from trying to say the perfect thing toward asking useful questions about the customer and the business. Understanding how a company makes money and how a solution affects it improves the current conversation while building the commercial judgment required for account, CRO, and executive roles.

How should sales teams use AI and KPIs without weakening human judgment?

Use AI as a productivity or coaching aid, but require managers and sellers to think through and internalize what the tool reports. Keep quantitative management focused on two to four conversational KPIs that can inform a decision, then pair those numbers with individualized coaching, accountability, and regular skills practice.