If you've ever trained a sales team, you know the pain: reps drowning in PDFs, skipping onboarding videos, and shadowing the one “star” rep who does everything differently. Most onboarding is too slow, too generic, and doesn’t stick. This guide is for sales managers, enablement folks, and anyone tired of the old ways—especially if you want to make onboarding actually useful, not just a box to check.
Let’s cut through the noise and talk about using Sellmethispen playbooks to build training that your team will actually use and remember.
Why Most Sales Onboarding Fails
Before we get into playbooks, let's be honest about why onboarding usually flops:
- Too much theory, not enough real-world context. Reps learn “the brand story” but get stumped in real calls.
- One-size-fits-all. The same material for new grads and seasoned sellers—neither gets what they need.
- No easy reference. Good luck finding the answer you need in a 70-page onboarding doc.
- No feedback loops. Nobody updates the onboarding after launch, so it gets stale fast.
If you recognize any of that, you’re not alone. Playbooks—done right—can fix these problems.
What Actually Makes a Good Sales Playbook?
Forget the buzzwords. A good playbook is:
- Actionable: Tells reps what to do in real situations.
- Short: Easy to scan, not a novel.
- Evolving: Gets updated as the market, product, or process changes.
- Findable: Organized so reps can get answers fast, on their own.
Most so-called playbooks are just glorified manuals. The key is making something that salespeople actually want to use because it saves them time and headaches.
How to Build Better Onboarding with Sellmethispen Playbooks
Here’s how to use Sellmethispen’s playbooks to actually improve your onboarding process. It’s not magic, but it beats another onboarding slide deck.
1. Map the Real Sales Process—Don’t Guess
Skip the theory and map out what actually happens from first contact to closed deal.
- Ask your top reps what they do at each step. Don’t just use the CRM pipeline stages—get specific.
- Shadow real calls and jot down what works, what gets awkward, and where new reps usually get lost.
- Look for common sticking points: First cold call? Discovery? Demo? Objection handling?
Pro tip: Resist the urge to overcomplicate. Keep it to 5-7 main steps. More than that, and new reps will tune out.
2. Build Playbooks Around Real Scenarios
Inside Sellmethispen, create playbooks for specific, real sales scenarios—think “Handling ‘Call Me Next Quarter’ Objections” or “Running a 15-Minute Discovery Call,” not just “Sales Process Overview.”
- Each playbook should answer: What do I say? What do I ask? What traps should I avoid?
- Use bullet points, sample scripts, and checklists—not walls of text.
- Link to live examples, call recordings, or short videos (but don’t make them required watching).
What to skip: Don’t write out every possible objection or edge case—focus on the 80% that comes up all the time.
3. Make Playbooks Accessible—Not Buried
If reps can’t find the playbook while prepping for a call, it’s useless.
- With Sellmethispen, organize playbooks by sales stage or topic, not by “Q2 Enablement Initiative” or some internal lingo.
- Use clear, boring labels (“Demo Script,” “Pricing Questions,” “First Week To-Do List”). Skip the clever code names.
- Make sure new hires know where to find playbooks on day one. Pin the link, add it to onboarding checklists, and mention it in kickoff meetings.
Pro tip: Ask a new hire to find a playbook in under 60 seconds. If they can’t, fix your labeling or navigation.
4. Tie Training Directly to Playbooks
Instead of a week of lectures, use playbooks as the backbone of your onboarding.
- Assign playbooks as “missions” or checklists for new hires to complete (e.g., “Run a discovery call using this playbook and record it”).
- Use playbooks in role-play sessions. Don’t just read them—practice them.
- When reviewing new hire calls, reference the relevant playbook: “Let’s see how you handled objections using this guide.”
What works: Make the playbook the source of truth, not just a handout. When managers reference it, reps follow suit.
5. Keep Playbooks Up to Date—Or Don’t Bother
A stale playbook is worse than none at all. Here’s how to keep them alive:
- Assign an owner to each playbook—someone on the team, not just enablement.
- Set a quarterly calendar invite to review and update. If nobody’s using a playbook, kill it.
- After team wins (or losses), update playbooks with what actually worked—or what crashed and burned.
Ignore: The urge to “perfect” every playbook or document every scenario. Good enough and current beats perfect and outdated every time.
What to Watch Out For
Some real talk before you dive in:
- Don’t expect instant magic. Playbooks help, but they’re not a substitute for real feedback and coaching.
- Avoid bloat. If your playbook is longer than a few screens, trim it. Nobody reads the appendix.
- Get buy-in. If leadership and frontline managers ignore the playbooks, so will everyone else.
- Beware of “template traps.” Copy-pasting generic playbooks or buying off-the-shelf content rarely works. Customize to your team and product.
Pro Tips for Getting the Most Out of Sellmethispen Playbooks
- Use real examples. Screenshots, anonymized call snippets, or short Loom videos beat text every time.
- Encourage feedback. Add a quick form or Slack channel for reps to suggest improvements or flag outdated info.
- Celebrate wins. When a rep uses a playbook to close a deal, share the story. It reinforces that these tools actually work.
Keep It Simple and Iterate
If you take one thing away, let it be this: the best onboarding playbooks are clear, short, and actually used. Start small—pick your top two or three sales scenarios, build quick playbooks, and get feedback from the team. Don’t stress about making it perfect. Update as you go, cut what doesn’t work, and make playbooks a living part of your sales culture—not shelfware.
Sales onboarding doesn’t have to be a slog. With the right playbooks (and a dose of common sense), you can get new reps selling faster, with less confusion and a lot less wasted time.