How should we prepare?

Prepare useful outreach

Research the buyer, prepare relevant messages and questions, and test useful outreach before expanding the workflow.

Browse all Tailwind episodes

7 conversations to explore

  1. Episode 50

    Prove One Prospecting Play Before Automating More

    With Dan Oakes, Founder at Startup Sales Consulting

    Dan Oakes recommends a frequent, useful trigger, clear workflow ownership, and a willing pilot rep before expanding AI-assisted outreach.

    Topics: AI in sales · Research · CRM and workflow · Discovery

  2. Episode 49

    Research the Names Before You Ask for an Introduction

    With Alana Nicol, Owner/President at Gerry Weinberg & Associates / Sandler Training

    Alana Nicol explains how ICP, LinkedIn connections, and a drafted introduction make it easier for a willing contact to help.

    Topics: Referrals and introductions · Research · LinkedIn · ICP

  3. Episode 48

    Give Prospects Something Useful Before Asking for Their Time

    With Joe Knotts, Fractional Sales Leader at Sales Xceleration

    Joe Knotts describes useful lead magnets, relevant company signals, and message testing that give outreach a clearer reason to exist.

    Topics: Research · Messaging · AI in sales · Email

  4. Episode 25

    Make Outreach Personal Before Asking for a Meeting

    With Steve Cashdollar, Sandler Trainer at Sandler Training Steve Cashdollar

    Steve Cashdollar examines specific personalization, curious calls to action, multichannel follow-up, and a digital presence that supports trust.

    Topics: Messaging · Research · Follow-up · LinkedIn

  5. Episode 21

    Find a Human Reason to Reach Out in an AI-Crowded Inbox

    With Dan McCoy, Founder at DLM Advisors

    Dan McCoy discusses researching shared context, building a network, and using AI as an assistant while keeping outreach recognizably human.

    Topics: Research · Referrals and introductions · AI in sales

  6. Episode 6

    Use AI to Rehearse, Take Notes, and Follow Up with Care

    With Jeff Borovitz, President at Sandler by Selling with Jeff

    Jeff Borovitz explores AI roleplay, richer call notes, and reviewed follow-up drafts while keeping disclosure and human context central.

    Topics: AI in sales · Sales training · CRM and workflow · Follow-up

  7. Episode 5

    Prepare Discovery Questions Before Recommending a Solution

    With Dan Cubr, Sandler Trainer at EAM Consulting Group

    Dan Cubr explains pre-call planning, buyer context, and questions that uncover pain before a seller jumps to a solution.

    Topics: Research · Discovery · Qualification · Next steps