The Mid-Year Sales Audit

A 4-part series on resetting, recalibrating, and closing the year strong

Howdy folks! 🤠

Can you believe it’s June? Hard to believe we’re officially halfway through the year.

For a lot of sales teams, this month usually looks something like this: Q2 closes, everyone takes a breath, and Q3 begins anew with many of the same habits you walked out of H1 with. Maybe a few deals have slipped…or pipeline is a little lighter than you’d like…or a rep or two is behind, and you’ve been meaning to address it. But the calendar keeps moving, so you keep moving too. 😪

I get it. Q2 close is exhausting. It feels like you’ve been running a 6-month marathon, and there’s always something more urgent competing for your attention. But, if you’re not careful, that drift is exactly how teams can end up missing the year.

On that bright note 😂, I’d like to introduce the concept of a mid-year audit. This is a structured framework to look at where you actually are, diagnose what’s working and what isn’t, and build a real plan for the back half of the year. Let’s dive in!

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📍 A Quick Reality Check

Before we get into the framework, take a quick pause and ask yourself if you can answer these questions without pulling a report…

• Are you pacing ahead of or behind your annual target? By how much?

• Where is your pipeline relative to what you need to close?

• Which reps are at risk of missing the year?

• What’s one thing about your sales process that’s broken and you’ve been tolerating?

If any of those made you uncomfortable...that’s where this series may come in handy. The whole reason you perform a mid-year audit is so those answers stop being surprises. The earlier you find the gaps, the more options you have to close them. If you’ve been reading WRT for a while, you know Christine and I are all about preparation!

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🔍 The Audit at a Glance

A mid-year sales audit has two halves - your numbers and your people. We’re starting with the 10,000-foot view this week and will be going deeper on each of these pieces in the weeks ahead.

📊 Half 1: Your Numbers

Pacing to Goal

• Why it matters: At the end of the day, your annual number is the most important number you have as a sales leader. This month’s and this quarter’s forecasts are great yardsticks to measure if you’re on track to hit in the big, but that is all they are. A lot of teams track monthly and quarterly performance without ever stepping back to ask: Are we actually going to hit the year? By June, you should have a good inkling of this, and also have an understanding of why you might be off track (and hopefully what you’re going to do about it in H2).

• Questions to ask:

  • What percentage of your annual target did you close in H1?

  • If H2 has to carry more weight, do you have the pipeline and capacity to support it?

  • Are there any structural changes (new hires, product launches, pricing changes) that should adjust your expectations up or down?

Pipeline Coverage

• Why it matters: A weak pipeline in June is a Q3 (and possibly even a Q4) problem. By the time you feel it, it’s usually too late to fix it for the current year. Coverage tells you whether you have enough opportunity in the system to support your targets, and if you don’t, you need to know now, not in September.

• Questions to ask:

  • What’s your current pipeline coverage ratio for H2 based on current trends?

  • What channels are performing well? What channels need help?

  • Is coverage consistent across reps, or is one person carrying the whole book? Is that planned or not? If not, why is that happening? Is that a lead equity or rep performance issue?

  • Are there any segments or territories where pipeline has dried up? Do you have a contingency plan?

Stage Conversion

• Why it matters: Where deals stall can tell you a lot. I wrote a pretty in-depth article about that here. If opportunities keep piling up at the same stage (demo to proposal, proposal to close, etc.), that’s a signal. It might be a rep skill issue, a process gap, or something your ICP has been trying to tell you. Either way, six months of data is enough to see a pattern.

• Questions to ask:

  • Where in the funnel are deals dying most often? Is this consistent across the team, or are there reps driving this up?

  • Has your conversion rate at any stage changed significantly since January?

  • What are your top three Closed-Lost reasons, and is there a theme? Has that changed over time?

Deal Velocity

• Why it matters: If deals are taking longer to close than they were six months ago, something has changed. Market conditions, your competitive landscape, your team’s execution, or possibly some combination of all three. Slowing velocity is one of the earliest warning signs most leaders miss because it happens so gradually.

• Questions to ask:

  • How does your average sales cycle length today compare to January?

  • Are there deal types or segments where velocity has changed more than others?

  • What’s the oldest open opportunity in your pipeline right now, and what’s the real story there?

🤝🏼 Half 2: Your People

Attainment Distribution

• Why it matters: The team number can hide a lot. One or two strong performers can mask a much bigger problem underneath. A mid-year check on individual attainment tells you who’s carrying more than their share, who’s falling behind, and whether your quota model is still calibrated correctly. This shouldn’t be a surprise if you’re holding weekly pipeline reviews. 😇

• Questions to ask:

  • What does your attainment distribution look like across the team right now?

  • Are the same reps who were behind in Q1 still behind? Or have things shifted?

  • Is anyone sandbagging? (Yes, this is a real audit item because yes, it does happen 👀)

Ramp Status

• Why it matters: If you hired in H1, your ramp timeline matters to your H2 number. A rep who’s behind at month four doesn’t automatically catch up, and a lot of managers wait too long to intervene because they don’t want to lose hope. The audit is your forcing function to look at this honestly.

• Questions to ask:

  • Are your H1 hires on track against their ramp milestones?

  • If someone is behind, is it a skill issue, a pipeline issue, or something else entirely?

  • Do you have enough fully-ramped capacity to hit H2 targets, or are you relying on ramp that hasn’t materialized yet?

  • If you’re planning on hiring in H2, can or will that impact numbers?

Coaching Gaps

• Why it matters: By June, you’ve had enough 1:1s and pipeline reviews to see patterns. Which reps keep getting the same feedback? Where are you as a manager spending most of your time, and is that where you should be spending it?

• Questions to ask:

  • What’s the one skill gap showing up most consistently across your team?

  • Are you spending coaching time where it’ll have the most impact, or defaulting to your strongest reps because it’s easier? Conversely, are you spending way too much time with your “problem children” and ignoring the rest of your team?

  • Is there a rep you’ve been avoiding a hard conversation with?

Process Tolerance

• Why it matters: Every team has something broken that nobody has gotten around to fixing (guilty 😮‍💨). A stage definition everyone interprets differently. A handoff between Sales and CS that keeps causing friction. A discount approval process that takes so long, reps just work around it. You likely know what yours is because you’ve been sweeping it under the rug for the last 6 months (don’t feel bad, we all do it). The back half of the year is harder if you drag it into H2 with you.

• Questions to ask:

  • What’s the one process issue that comes up repeatedly in your team’s complaints or your own frustration?

  • Is this something you can fix in the next 30 days, or does it require a bigger conversation?

  • What’s the cost of continuing to tolerate it for another six months?

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🗓️ What We’re Covering This Month

Okay. I know that was a lot. Don’t freak out!

Over the next few weeks, as mentioned, we’ll be going deep on all of the above, along with templates and frameworks you can actually use, not just concepts to think about.

Here’s what that looks like:

• Week 1: Why the mid-year checkpoint matters and the full audit framework at a glance ← You are here! 🗺️

• Week 2: Auditing your numbers - a pipeline and performance diagnostic with a template you can run with your team

• Week 3: Auditing your people - a rep-by-rep assessment framework and a guide for the harder conversations

• Week 4: Building your back-half plan - how to turn everything you found into a clear, prioritized path to December

🚨 Quick note: Weeks 2 through 4 will be subscriber-only. 🚨

If you’ve been on the fence about upgrading, this is a good time to do it. It costs less than a cup of coffee a month! 🙂 You can subscribe here ⬇️

Happy auditing! 🕵🏻‍♀️
Stacy

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📚 Stacy’s Book Challenge

This year’s goal is…81. 1 more than last year. 😮‍💨 Follow along as I try to get there.

As of this post, I have read 34 books. Oof - not much progress since last week, though, to my credit I’m reading a 1000-page book lol.

I’m currently reading:

• Dungeon Crawler Carl - Haven’t really touched the book this week 😬

• Blood Meridian - Yeah…no progress here either…I refuse to DNF any book this year, so I’ll try and pick it up soon…

• Gai-Jin - Still having a great time with this one! This has GOT to count for two books 🤣

• Sunrise on the Reaping - Very much in the same vein as all of Suzanne Collins’s other books, so pretty easy read

Follow me on GoodReads! 🤓