It’s July. Your board deck is due next week. You’re staring at a pipeline that looked promising in January but now feels like it’s held together with duct tape and wishful thinking.

I’ve had this exact conversation with 47 revenue leaders in the past six months. Same story: “We’re not quite where we thought we’d be, and we don’t know why.”

Here’s what I’ve learned from sitting in those uncomfortable revenue reviews: the teams that turn it around in the second half do four things differently. Not because they read it in a McKinsey deck, but because they’re honest about what’s actually broken.

 

4 Ways to Fix Your Sales Year Before Q4

 

1. Admit When You’re Burnt Out

Last month, a CRO at a $300M ARR company told me: “I wake up every morning and immediately check Slack to see what’s on fire. I haven’t felt excited about a deal in eight months. My team can smell it on me.”

That’s not leadership burnout; that’s total loss of purpose.

Most revenue leaders won’t say this out loud because we’re supposed to be the energy source for everyone else. But here’s the thing – if you don’t care anymore, neither will your team. And customers can sense it.

 

❓ Ask Yourself: When’s the last time you talked to a customer who actually loves your offering? 

One CRO I work with started doing monthly “coffee with customers” calls. Not sales calls. Just conversations. It reminded him that their software was helping small businesses survive COVID. Meeting with customers beyond case studies and renewal calls will help you remember why what you do matters.

 

2. Count Pipeline Like Your Job Depends On It (Because It Does)

“We have great pipeline coverage” is the most expensive lie in B2B sales.

Coverage ratios don’t matter. 

What matters is: How many deals can you actually close this quarter that you haven’t closed yet?

I watched a VP of Sales present a 4.2x coverage ratio to his CEO. It looked great on paper, but then we dug into the actual deals:

  • 40% were stalled for over 90 days
  • 30% had “TBD” close dates
  • The remaining 30% were mostly inbound demos that hadn’t had a second meeting

So the real coverage was only 1.1x. They missed the quarter by 38%.

 

❓ Ask yourself: When you look at each deal closing this quarter, can you name the person who will actually sign the contract and when they plan to do it?

If you’re guessing, it’s not real pipeline.

 

3. Fix the Machine, Not Just the People

Most sales process problems aren’t people problems; they’re structural problems that good people are trying to work around.

Example: A global enterprise company was losing 60% of deals in legal review. The sales team kept getting training on “closing techniques.” 

The real problem? They weren’t getting the contracting process aligned with the customer early enough. 

SOAR re-aligned their sales process to make this a non-negotiable milestone in stage 3. As a result, the win rate in legal went from 40% to 78%.

 

❓ Ask Yourself: Where are deals actually dying? (Not where you think they should die).

If 50% of your opportunities stall after the demo, either you aren’t discovering the right things before the demo, or the demo itself misses the mark. 

 

4. Know the Difference Between “Can’t Do” Reps and “Won’t Do” Reps

This is where most revenue leaders mess up; they see underperformance and immediately think it’s a training problem.

I’ve seen companies spend $200K on sales training for reps who fundamentally don’t belong in sales. I’ve also seen companies fire good reps who just needed to learn how to run a proper discovery call.

 

❓ Ask yourself: What category do each of our reps fall into?

The “Can’t Do” Rep: Asks good questions, takes feedback well, cares about the outcome, but missing specific skills. Example: A rep who builds great relationships but struggles to articulate ROI.

The “Won’t Do” Rep: Has the skills but doesn’t use them. Shows up late to calls, doesn’t prep, makes excuses. Training won’t fix attitude.

 

 

How to Effectively Reskill Underperforming Account Executives (Without Wasting Everyone’s Time)

 

Step 1: Have Them Shadow Your Best Rep for One Week

Have your underperformer shadow your top performer for five days straight; every call, every email, every internal conversation.

A startup CRO tried this with her worst AE. The lightbulb moment came on day three when the underperformer said: “Wow, Sarah asks three follow-up questions for every one I ask.” 

 

Step 2: Practice the One Thing That Matters Most

Don’t try to fix everything. Pick the one skill that, if improved, would have the biggest impact on the AE’s numbers.

For most underperforming AEs, it’s discovery; they’re order-takers rather than consultants.

Here’s the drill: Every Monday, have underperformers practice one discovery conversation with a manager. Use the same scenario with different variations. By Friday, they should be able to uncover business problems and potential value in 15 mins. 

One rep went from 8% discovery-to-close rate to 31% in six weeks using this approach.

 

Step 3: Measure Behavior, Not Just Results

Results lag behavior by weeks or months. So, if you’re only measuring closed deals, you won’t know if your reskilling is working until it’s too late.

Try these behavior-based metrics for discovery training:

  • Number of quality discovery questions per call 
  • Percentage of calls where real business problems and ROI are discussed 
  • Average time from first call to proposal

Track these weekly. If the behaviors don’t improve in 30 days, the reskilling isn’t working.

 

Step 4: Give Them Real Deals to Practice On

The biggest mistake: practicing on fake scenarios. Your underperformer needs to practice new skills on real opportunities with real consequences.

Start them with smaller deals or renewals: lower stakes, but real outcomes. If they can’t execute the new skills when it matters, they can’t execute them at all.

 

When Reskilling Won’t Work

Here are the red flags to indicate an AE can’t be successfully reskilled:

  • They blame external factors for everything (the leads are bad, the marketing is bad, the product is too expensive)
  • They don’t take notes during coaching sessions
  • They argue with feedback instead of asking clarifying questions
  • They can’t remember what they learned from one week to the next

If you see these signs, it’s time to cut your losses. Your A-players are watching how you handle underperformers. If you keep making excuses for people who won’t improve, you’ll lose the people you can’t afford to lose.

 

The Part Everyone Misses

Most mid-year assessments focus on what to do differently. But the real question is:

What are you going to stop doing?

Stop calling pipeline meetings “pipeline reviews” when you’re not actually reviewing anything. Stop pretending activity metrics matter if they don’t correlate to revenue. Stop scheduling all-hands meetings to “align on priorities” when your priorities are already clear: Close more deals.

And of course, stop trying to reskill people who don’t want to be reskilled.

The teams that crush Q4 don’t do more things. They do fewer things better, with people who actually want to win.

 

What’s one thing you’re going to stop doing this week? And which rep are you finally going to have the hard conversation with?

 

Contact us if you want help in any of these areas to fix your sales year before Q4!