If you’re running a B2B sales team, you know the feeling: everyone’s winging it, nobody’s on the same page, and you’re wasting hours explaining the same stuff over and over. A good sales playbook should fix that. The bad news? Most playbooks are either ignored or so packed with fluff that nobody actually uses them.
This guide is for managers and enablement folks who want to actually make their team’s lives easier—using Highspot to do it. I’ll walk you through building a sales playbook that reps will actually use, and I’ll be brutally honest about what works and what doesn’t.
Step 1: Get Clear About Why You Need a Playbook
Before you start dumping templates and scripts into Highspot, ask yourself: what’s the real problem you’re trying to solve? Is it onboarding? Inconsistent messaging? Reps missing key steps? If you can’t point to a couple of real pain points, you’re about to waste your time.
Pro tip: Talk to your reps. Ask them where they get stuck, what they wish they had at their fingertips, and what they never bother looking at. Your playbook should make their job easier, not just check off a box for leadership.
Step 2: Map Out the Core Sales Process
Don’t copy-paste a generic sales process. Map out what actually happens in your team’s deals, from first touch to close. If you sell into mid-market SaaS, that’ll look different than enterprise construction.
Essential steps to include: - Prospecting (how you actually do it, not just “do more activity”) - Discovery (what questions matter? what red flags?) - Pitch/demo (what do you show, what do you skip?) - Objection handling (the real ones you get—not theoretical ones) - Pricing/proposal - Closing steps (legal, procurement, whatever's real for you) - Handoffs to success or onboarding
What to skip: Don’t bother with endless “buyer personas” or elaborate qualification frameworks unless your team really uses them. Stick to what moves deals forward.
Step 3: Gather the Content—But Ruthlessly
This is where most playbooks go to die. People start uploading everything: every PDF, every call script, every pricing deck since 2018. Don’t do that.
What you actually need: - Winning email templates and call scripts (the ones reps actually use) - Short videos or call recordings of what “good” looks like - Decks and one-pagers that are current - Battlecards on real competitors (if you’re not sure who those are—ask your reps) - Objection-handling cheat sheets
What to skip: - Anything outdated, or “just in case” content - Long policy documents (put those somewhere else) - Marketing fluff that doesn’t help close deals
Pro tip: If you aren’t sure whether to include something, leave it out. You can always add it later if reps ask for it.
Step 4: Structure Your Playbook in Highspot
Highspot can be powerful, but it’s easy to overcomplicate. Here’s how to keep it simple and usable:
a. Set Up Spots for Each Stage
In Highspot, “Spots” are basically folders. Create a Spot for each stage of your sales process, not for every random situation.
Example Spot structure: - Prospecting - Discovery - Demo/Pitch - Objection Handling - Proposal/Pricing - Closing & Handoffs
This way, reps know exactly where to look, fast.
b. Use Playbooks, Not Just Content Dumps
Highspot “Playbooks” let you bundle content, guidance, and action steps together. Use these for things like: - New rep onboarding - How to run a first call - Beating a specific competitor
Each Playbook should answer: “What should I do next?” and “Where’s the stuff I need?”
c. Add Context, Not Just Files
Don’t just upload a pile of PDFs. Add short notes or checklists to each section. Tell reps when and why to use a piece of content.
Bad: “Q3 Product Deck.pdf”
Good: “Use this deck for technical buyers who ask about integrations. Skip slide 7—it’s out of date.”
d. Use Links, Not Attachments
Wherever possible, link to the latest version of documents (Google Docs, etc.) instead of uploading static files. This keeps things fresh and avoids the “which version is this?” headache.
Step 5: Keep It Short—But Not Useless
Your reps don’t have time for a 60-page manual. Focus on what they’ll actually need in the next call or email.
What works: - One-pagers - Short videos (under 2 minutes) - Bullet points over paragraphs
What doesn’t: - Overly detailed process charts - “Inspirational” vision statements
If something takes more than five minutes to read, it goes to a reference library—not your core playbook.
Step 6: Roll It Out—And Actually Train the Team
Just uploading your playbook to Highspot won’t change anything. Schedule a short session to walk the team through it. Show them how to find stuff, and ask for feedback right away.
Honest advice: If reps can’t find what they need in under 30 seconds, they’ll never use it. Watch someone try to use your playbook. Where do they click? Where do they get stuck? Fix it.
Pro tip: Nominate a “skeptical” rep to test-drive the playbook. If they can’t use it, nobody will.
Step 7: Get Feedback, Iterate, and Keep It Alive
The best playbooks are never “done.” They get updated as you learn what works and what’s ignored.
How to keep it useful: - Set a calendar reminder to review and update every quarter - Ask reps what’s missing or what’s outdated - Kill off anything nobody’s using - Add new “winning” examples from real deals
What to ignore: Fancy analytics dashboards or usage metrics that don’t tell you why something’s not being used. Just ask your team.
Step 8: Avoid Common Pitfalls
Here’s what trips up most B2B teams:
- Overcomplicating the structure: If it takes a map to navigate, you’ve gone too far.
- Letting marketing run wild: Only include what helps close deals. The rest is noise.
- Trying to make it perfect: Get the basics live, then improve it as you go.
- Ignoring adoption: If your reps aren’t using it, figure out why and fix it—don’t just blame “change resistance.”
Summary: Keep It Simple and Useful
A sales playbook should make your team’s life easier. That means less time searching for stuff, more time selling. Don’t let Highspot become a digital junk drawer. Start with the basics, keep it short, and iterate based on what actually helps close deals. If you’re not sure whether to add something, skip it. Your reps (and your sanity) will thank you.