Why Every Employee Needs a Performance Plan — Even Your Top Seller (And Other Truths About Sales Leadership, Private Equity, and the Future of Work)
If you’re not talking to your team about how they’re going to hit their number — and how they’re evolving in the process — you’re already behind.
We recently sat down with JD Miller, a 6-for-6 private equity-backed CRO, advisor, and author of The CRO’s Guide to Winning in Private Equity, for one of the most eye-opening episodes of Mastering Modern Selling yet.
We covered everything from PE strategy to AI, but the boldest take was this:
“Every employee should be on a performance improvement plan — not as punishment, but as a path to growth.” – JD Miller
Let that sink in. Performance improvement has a stigma in most orgs. We think it’s what happens right before someone’s shown the door. JD and I agree: it’s time to flip the script.
This isn’t about managing people out. It’s about leveling people up.
Why the Traditional PIP is DeadJD got fired once — with zero warning.
“I thought I was doing great. Then HR pulled me in and said, ‘No one else thinks you are.’ I was shocked. But looking back, they were right about some things — and I had no idea.”
That moment changed how he thinks about feedback, growth, and leadership. And it should change how you think about performance plans.
Most companies wait until it’s too late to have hard conversations. By then, it’s HR paperwork.
But what if every employee had a quarterly growth conversation — where they discussed what’s working, what’s not, and how they’re building toward the next level?
“A great PIP is a career development plan — not a firing roadmap.”
The Private Equity Mindset Every Leader NeedsJD’s worked inside six successful exits — and now advises PE-backed companies on how to scale sales and marketing.
What separates winners from wannabes?
“You need a real plan. Not just a number you signed up for at the board meeting.”
Every CRO should be breaking down their growth targets into:
Net new logos Upsell & cross-sell Customer retention Churn risk mitigationToo many leaders are flying blind, hoping the number magically happens.
AI Isn’t Coming for Your Job — But Someone Using It Might“The future belongs to the people who get comfortable being uncomfortable.”
Sales reps used to get grace. “Tell me about your problems,” was a valid opening.
Today? You’d better show up with insight and a POV. With AI, every call is transcribed. Every missed MEDDICC qualification is flagged.
Top reps (and leaders) are using AI to:
Analyze calls for coaching opportunitiesRefine messaging based on buyer signalsPredict churn and optimize renewalsSummarize meetings, draft emails, and prep proposalsIf you’re not using these tools to improve yourself daily, you’re falling behind.
Practical Tips You Can Use TODAY
Implement Quarterly Performance Plans for Everyone Frame them as growth journeys, not warnings.
Get Real About Your Annual Plan Break it down into inputs: logos, upsell, churn, etc. Then reverse-engineer the activity.
Embrace AI for Coaching Use AI to review sales conversations and identify gaps in qualification or messaging.
Align Sales & Marketing Around a Single Equation Work backwards from revenue goals to define how many opportunities, meetings, and touches are needed — together.
Make Your Team a Destination Survey your people. Build a feedback loop. Show them they matter.
“We should all be trying to be the person we promised to be on interview day.”
Final WordYou can’t afford to run a team where 10% of the reps do 90% of the work. And you sure can’t afford to wait until someone’s underperforming to help them grow.
Every person. Every quarter. One plan. One path forward.
Let’s rebrand “PIP” into what it should be:
Progress. In. Practice.
And let’s make growth the default — not the exception.
Grab JD’s book: The CRO’s Guide to Winning in Private Equity 
More insights at: jdmillerphd.com
