The hidden management problem that costs you millions
Your sellers missed goal this month. Again.
Your forecast accuracy? Tanked. Your executive leadership? Seriously not thrilled.
Are your frontline reps bombing … or is that star performer you promoted to sales manager failing to deliver the coaching your sellers really need?
The double jump sales management problem
When sales leaders promote someone for their selling skills, rather than their managerial prowess, they set the entire team up to fail.
Rather than coaching frontline sellers on how to deliver Commercial Insight to the right buyers, unprepared managers instead focus on the wrong selling skills, reinforce sellers’ bad habits, or just take over and close deals themselves.
We call this the double jump problem.
From seller to manager
But the skills that make someone successful at selling — discovery, listening, negotiating — differ greatly from what they need to manage effectively — developing, analyzing, and planning.
Without those skills, sales managers can’t do their jobs. And that means neither can your sellers.
From product to Insight
Buying and selling is harder than ever. Challenger research found that buyers spend only 17% of their buying time meeting with all vendors, including competitors. And according to Gartner, 75% of buyers want a rep-free experience.
Too many sales managers fall back on features and benefits selling. But it’s Commercial Insight — not product knowledge — that breaks through this chaos spiral.
You can’t afford mediocre sales management…
Gartner reports that just one ineffective sales manager can cost a company millions.
You lose the output of a top-performing seller.
If your best performer no longer carries a bag, your quota attainment naturally takes a hit — and Repvue found that average quota attainment is already at an embarrassing 42.7% in 2024.
Too often, sales leaders believe they can make up for that lost performance just by scaling exactly what that seller did to succeed. But it’s a little more complicated.
Your new manager struggles — and so does their team.
Frontline reps look to their managers to support skill development and coaching. Yet only 38% of sellers told Gartner that their manager helps them develop the skills they need for their role today — and 42% of sales managers noted that they lacked confidence to develop seller skills. Your formerly successful seller is miserable, and so is their team.
Your sellers flee, and so does your revenue.
Blue Ridge Partners reported that a 5% increase in sales rep attrition can increase selling costs by 5% reduce revenue attainment by up to 3%. And turnover is already high — Hubspot found that B2B organizations experience an average of 35% a year.
One inexperienced manager can drive away too many reps — resulting in a very, very bad year.
…so start preparing your sales managers to excel
As Matt Dixon and Brett Adamson, who wrote “The Challenger Sale” noted: There is no other productivity investment that comes close to coaching in improving sales reps’ performance.
Revenue Growth
Training Industry reported top-performing sales managers drive their sellers to a 72% win rate versus an overall average of 47%.
Engagement
65% of frontline reps told Seismic that they’re more engaged in their jobs when they receive high-quality coaching.
Retention
Seismic found seller retention grew 28% when they received on-the-job coaching — which means less time replacing and retraining talent.
By investing in developing and improving manager skills, sales leaders can grow a talent pool that makes a hugely positive impact on the organization.
Find the right training for your sales managers
You need a program that upgrades your sales managers’ coaching skills — particularly those attributes that drive behavior change in sellers.
The elements you need in sales manager training
Stop the double jump problem before it starts with an effective, proven manager training program.
Preparation for buy-in
Use prework to ensure managers show up ready to learn and apply the training
Live learning
Classroom experience taught by a credible facilitator with sales expertise, aligned to adult learning methods
Peer feedback
Opportunities for practical application and feedback from peers in a safe learning environment
Tools
Resources to keep the learning alive and support skills application after the workshop ends
Reinforcement
Ongoing access to online learning resources that support long-term behavioral change
Great coaching begins with Challenger
Ready to nip the double-jump problem in the bud? Find the suite of Challenger coaching programs that’s right for you.
You need to know where to start. Assess each of your managers’ proficiency in coaching, selling, and innovation, then hone in on areas for improvement.
Improve your sales’ managers coaching capabilities by showing them how to develop their teams’ Challenger skills, observe their behavior, and coach them to better performance.
In this advanced coaching workshop, learn and practice ways to coach frontline sellers to manage stakeholders, overcome objectives, and diminish resistance to Constructive Tension.
Take your manager’s skills to the next level with interactive and engaging exercises purpose built to raise coaching acumen that drives high quality interactions.
Note: Revisiting Coaching Principles is recommended for organizations who have already completed Coaching to the Challenger.
Energize frontline managers with research and tactical tips to help them understand their role in guiding sellers to behavioral change
Bring sellers and managers together to learn how to land real-life, must-win deals with an expert Challenger advisor.
Walk through the biggest problems your coaches and sellers face with facilitator-led, small-group workshops that sharpen skills like outreach, group meetings, negotiations, and urgency drivers. Every Level Up ends with a manager-only debrief.