Joking with prospects can backfire badly

Published: Wed, 04/30/25

Updated: Mon, 05/05/25

April 30, 2025

TOGETHER WITH

Welcome back to The Quota, the sales newsletter that shows up on time, unlike that coworker who waltzes in late, smelling like a brewery. In this week’s issue, we’ll look at what Harvard Business Review says reps need at each stage of their career journey, then go through our usual Fails, Advice, and other goodies. Close out your other browser windows and enjoy!

NUMBER OF THE WEEK

62% of sales professionals say their organization is taking fewer strategy risks.

Source: HubSpot

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

AI-powered robots could soon be selling cars to customers in the UK, as a global car manufacturer debuts an unusual new member of staff. Omoda and Jaecoo owner Chery showed off robotic sales assistant ‘Mornine’ at the Shanghai Motor Show on April 23. It can greet customers, show them around a car, and even make tea or coffee. Greeeat… You can read more about it here.
A 67-year-old Petaluma, California man was arrested for allegedly brandishing a firearm at a door-to-door salesman, police said Sunday. Michael Greenwood was arrested on April 21, after allegedly chasing a solicitor down the street. He was booked into Sonoma County Main Adult Detention Facility on accusations of making criminal threats and brandishing a firearm. You can read the article here.

FEATURE

How to nurture sales rep at each stage of their career, according to Harvard Business Review

New research in Harvard Business Review outlined how sales organizations typically evaluate talent through three primary lenses: competencies (technical skills and knowledge), motivation (internal drivers), and performance (measurable results). However, researchers identified a crucial fourth dimension that many organizations overlook: career stage. Their findings show that salespeople face distinctly different challenges and opportunities depending on where they are in their professional journey.

The needs of a rookie are much different than those of a ten-year veteran. A salesperson who's been crushing targets for three years requires different coaching and motivational techniques than someone with similar success who's been in the field for a decade. Understanding career stages can help sales leaders know what their sales reps actually need to grow over time.

The Real Stages of a Sales Career

Year One – The Rookie Phase: Bright-eyed and often terrified. New salespeople aren't helped by quota pressure. They thrive with managers who focus on building fundamentals and celebrating small wins. Research showed that salespeople who closed any deal in their first 90 days are significantly more likely to succeed long-term.

Years 2-3 – Finding Your Stride: The initial excitement has faded, but patterns emerge. The pitch feels natural, but complex deals still require guidance. This is when public recognition becomes particularly powerful. Being asked to present strategies at quarterly meetings can sometimes mean more for these salespeople than financial incentives at this stage.

Years 3-5 – The Sweet Spot: Consistently strong performers who feel underappreciated become prime targets for competitor recruitment. The researchers found that successful organizations give these professionals greater autonomy and strategic involvement. At this stage, they’ve earned it.

The Veteran Phase (6+ years): Here the path divides:

Still Growing: Veterans need fresh challenges to stay engaged. Advisory roles and mentoring opportunities can prevent stagnation.
The Plateau: Comfortable accounts practically run themselves. These salespeople aren't failing, but they're not growing either. Financial incentives rarely shake them from comfort zones—but new responsibilities often do.
The Decline: Some seasoned reps can be so disengaged that their performance drops and attitude sours. If turnaround attempts fail, the best path forward might be respectfully showing them the door.

Career Implications

Understanding this progression can help leaders give their reps what they actually need:

Rookies benefit from mastering fundamentals before obsessing over numbers.
Mid-career reps thrive with recognition through strategic involvement, not just compensation.
Veterans feeling in a rut can be reinvigorated by mentoring rookies or joining advisory councils.

For Sales Leaders

A top performer and struggling rookie need completely different things from their leaders. A one-size-fits-all approach doesn’t work and can lead to higher churn and lower quota attainment.

Sales organizations that tailor their approach to each person's career stage see dramatically better engagement and performance across the board. Salespeople professionals aren't parts, but people at different stages of their career journey.

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How long you can get away with being “new” until you’re held accountable
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How to find a workplace friend and make a workplace enemy
Camera position: how to set up your laptop for maximum dominance
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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

Who played Jordan Belfort’s father, Max, in the movie The Wolf of Wall Street?

A. Kyle Chandler
B. James L. Brooks
C. Ron Howard
D. Rob Reiner

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I used to sell funeral services. I only lasted about a year, and it was a pretty depressing job. One day, I was showing casket options to this family who had just lost their elderly mother. Overall, they seemed to be handling the whole situation well, as people crying in the showroom was not an unusual occurrence.

After about 30 minutes, they had decided on a nice mid-range mahogany model. I was told that whenever customers picked anything mid-range or above, it was an opportunity to upsell them. I started showing them upgrades and pitched them a premium silk interior package. Trying to keep the mood light, I said "Your mother will be spending a lot of time in this, so comfort is key." I don’t know why I said this—I think I was in a pretty good mood that day.

Complete silence. After a moment, the son looked me dead in the eyes and said, "Do you really think this is a good time to be making jokes?" I apologized profusely. The son accepted the apology and told me it was fine but I could tell he was upset. He told me they'd take the silk interior package and handed me his credit card and said, "Just let me pay so we can get out of here." I got the sale and he walked out, but that was the last time I ever tried to make a joke at that job.

Anonymous Location withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- April 2025

WORTH A PEEK

What is the biggest lesson/cliche you’ve learned from working in sales? A recent Reddit thread posed this question to the r/sales audience, and responses were wildly entertaining. Seriously—can’t stop reading now. See the conversation here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Dear Quota Team,

I spent nearly eight months working my way into a Fortune 100 account — cold outreach, late-night calls to match their time zone, in-person meetings — everything. A few weeks ago, I finally got a real opportunity open with them. Two days later, my manager pulled me into a meeting and said the deal was being "transitioned" to our strategic accounts team because it’s now considered "too important for a field rep to manage." I get a handoff bonus and a small percentage on commission if they sign. I feel totally screwed on what could easily be a seven-figure deal. I want to confront my manager and tell him to let me stay on the account that I brought in. How should I approach this conversation? Honestly, if he keeps me off the account I'm probably going to quit.

Furious in the Midwest

Dear Furious,

Your anger is understandable. But first, take a breath. If you go into the conversation railing about how you "earned it" (although you did) your manager won't be inclined to listen. Frame your conversation around the company’s best interests, not just your personal frustration—yes, this will be hard. Show how your existing relationship and momentum can increase the odds of closing the deal faster. Propose a hybrid approach where you stay involved as the primary rep with strategic support layered in. If leadership still sidelines you, you’ll have your answer — and a good reason to start lining up your next move.

Quiz Answer: D. Director Rob Reiner played Jordan Belfort’s father, Max, in The Wolf of Wall Street

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Today's email was written by Ken Kupchik, Erica Furgiuele, Steve Rado, and Emily Hill.

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