Setting New Hires Up to Fail

Originally published in The Sales Recruit on August 14, 2025.

Photo by Volodymyr Hryshchenko on Unsplash

Hey everyone, welcome back the Sales Recruit— Let’s jump into it.

Sales Hiring Links of the Week:

• 9 Recruitment Trends Surging in 2025 - A couple of interesting trends that I’m keeping my eye on, including employee advocacy and hybrid flexibility dramatically increasing win rates with candidates.
• AI and Sales Assessments: What You Need To Know - Quick read from one of the best sales assessment tools out there about the risk of candidates using AI to game tests.

This Week’s Task: Revisit Your Sales Hire Onboarding Plan

I had a client early on who hired a salesperson I had helped them assess and interview. The salesperson shined in the recruiting process, had impressive references, and made a great early impression on the team. Then, mysteriously, just 3-4 months in, he seemed to have lost all of his juice. He was flaming out, hadn’t really produced anything, and there was a mutual decision between the rep and management that it was best they part ways.

Naturally, the President of the company came to me wanting to know why I’d endorsed a bum candidate. Embarrassed, I asked if they had seen any red flags when advancing the rep through the detailed onboarding curriculum I’d designed for them. The President stared at me blankly as if to say, “What onboarding curriculum?”

They’d never even shown it to the rep.

They’d just hired the rep and expected them to figure it all out on their own.

Here’s the brutal truth: Most companies think hiring a great salesperson = instant revenue. Wrong. Even rockstar reps need a roadmap to succeed in your environment.

The average $50k+ cost of skimping on the onboarding plan includes:

• Extended ramp time (6+ months instead of 3)
• Wasted salary with zero ROI
• Good reps leaving for better-organized competitors
• Repeated hiring cycles that drain your budget

So, let’s stop treating onboarding like an afterthought.

A good onboarding plan should pass the accumulated knowledge of our sales organization over the many years of its existence on to the new hire in as short a time as possible. Further, we need to make sure we are building in checkpoints along the way where we can review the new hire’s progress to make sure they’re on track (or figure out early if we just made a bad hire).

Onboarding Sales Hires Checklist

Here is a non-exhaustive list of things to consider adding to your onboarding check list:

• ☑️ Review job description with manager and discuss specific leading indicators and KPIs that will measure success/failure
• ☑️ Discuss corporate culture and sales approach/style with VP of Sales
• ☑️ Review Sales Playbook and CRM stage definitions with manager
• ☑️ Review Ideal Client Profile with manager
• ☑️ Share personal and professional goals with manager
• ☑️ Build and present a personal behavior plan that ties daily activities to meeting/exceeding quota
• ☑️ Hear referenceable customer success stories from Customer Success Lead
• ☑️ Review findings from Objective Management Group assessment (or other assessments) with direct manager and discuss growth opportunities
• ☑️ Discuss common objections in our sales process and how we handle them with Sales Leader
• ☑️ Weekly role-play practice with sales manager

And here are some example checkpoints to build in to your onboarding plan:

• ☑️ Deliver an effective value proposition/elevator pitch for Sales Manager by end of Week 2
• ☑️ Demonstrate an effective initial discovery call in role-play by end of week 3
• ☑️ Be meeting or exceeding daily outreach targets by the end of week 4
• ☑️ Demonstrate the ability to cogently differentiate our offering from our top 3 competitors’ in role-play by the end of week 6

What would you add to the above list to help ensure a salesperson hits the ground running?

Chris