Sales Horror Stories 😱 Jen vs. Will Halloween Special
TLDRIn this engaging conversation, Jen and Will share their most memorable and cringe-worthy sales stories. Jen recounts a tale of a failed deal and harsh criticism from a stakeholder, while Will describes an incident where his unauthorized outreach led to a chief sales officer's firing. Both stories highlight the highs and lows of a career in sales, with a touch of humor and a lesson in navigating professional challenges.
Takeaways
- 🎭 Personal Attacks - Jen faced a highly personal attack from a stakeholder who deemed her the 'worst human being' and advised her termination.
- 🤯 Misunderstandings in Communication - A stakeholder's lack of action led to Jen's assumption that progress was being made, which was later revealed to be incorrect.
- 🏌️♂️ Golf Event Strategy - Jen's bold move of inviting a CEO to a golf event unexpectedly backfired, leading to severe criticism and a lost deal.
- 📚 Book Learnings - Will improved his sales skills by studying a renowned sales book, both in written and audio formats, and practicing with his wife.
- 📈 Career Growth - Will's dedication to learning and applying new sales techniques led to a new job and positive coaching, enhancing his career.
- 🤝 Sales Training Engagement - Will's interaction with a sales training company began with a demo and discovery, revealing a potential solution to their problems.
- 💸 Pricing Negotiation - A negotiation tactic involving a reduced cost for a sales training tool backfired when the prospect refused to pay, highlighting a mismatch in expectations.
- 🔥 Conflict Escalation - Will's direct approach to a sales trainer resulted in the firing of a Chief Sales Officer and his company being blacklisted.
- 👻 Storytelling Impact - The power of a well-told story was evident as Will's actions led to significant consequences for both him and the sales trainer involved.
- 🧠 Reflective Learning - Both Jen and Will's experiences provided valuable lessons and opportunities for self-reflection and growth in their sales careers.
- 👥 Audience Involvement - The audience was engaged to vote on the scariest sales story, showing the shared nature of such experiences in the sales industry.
Q & A
What was the main reason for Jen feeling that her sales career became scary?
-Jen's sales career became scary when she started working with a stakeholder who turned out to be uncooperative, leading to a significant emotional toll and a failed deal.
How did the stakeholder's boss react when Jen invited him to a golf event?
-The stakeholder's boss called Jen's boss and complained about her, saying she was one of the worst human beings he had ever met and suggested she should be fired.
What was the outcome of the stakeholder's boss's phone call with Jen's boss?
-The stakeholder's boss told Jen's boss that Jen was terrible at sales and should never be in the profession, and then he hung up without further discussion.
How did the situation with the stakeholder affect Jen's future behavior in her career?
-The experience made Jen too scared to ever go over someone's head again, fearing a similar negative outcome.
What action did Will take to improve his sales skills?
-Will bought a book from a renowned sales author, read it multiple times, and practiced with his wife, which eventually led to him becoming better at sales.
What was the main issue that Will identified when working with the sales training company?
-Will found out that the sales training company was burning money on a problem that his solution could solve.
How did the sales training company react to Will's proposal to sign up for his solution?
-The sales training company refused to pay for the technology, believing they were above using sales tech and that it would be a bad look for them if it got out that their sales team had issues.
What was the consequence of Will sending an email directly to the sales trainer?
-The sales trainer fired the chief sales officer and also banned Will's company for revealing the internal issues of their sales team.
What did Will learn from his experience with the sales training company?
-Will learned not to meet his heroes and that using someone's success as a story of what not to do can have a significant impact.
Which story did the audience have to decide between as the scariest?
-The audience had to decide between Jen's story of being called terrible at sales and almost losing her job, or Will's story of causing a chief sales officer to be fired by going around the hierarchy.
What long-term effect did these experiences have on Jen and Will?
-Both Jen and Will still feel the impact of these experiences, with Jen being cautious about going over someone's head and Will reflecting on the consequences of his actions.
Outlines
💥 Confrontation and Career Critique
The first paragraph revolves around a tense and emotionally charged interaction between colleagues. Jen is criticized for her career aspirations, with a reference to her role as a backup dancer and an assumption that she will never reach the level of Britney. The conversation takes a personal tone, with references to nostalgia and past experiences. A Beetlejuice costume adds a humorous element to the exchange. The discussion then shifts to a sales context, with a challenge for the participants to share their scariest or most embarrassing sales stories. The story concludes with a setup for a 'scary story off' where the audience will vote on the most frightening tale based on the participants' experiences in sales.
📈 Sales Struggles and Unexpected Outcomes
The second paragraph delves into the challenges faced by Will in his sales career, highlighting a specific incident where he invested significant time and effort into a major opportunity, only to realize that the stakeholder he was working with was not contributing to the progress of the deal. The situation escalates when Will's boss receives harsh criticism about Will's sales abilities from the stakeholder, leading to a demoralizing phone call where Will is berated and made to feel inadequate. The story serves as a cautionary tale about the potential pitfalls and emotional toll of a sales career, and the importance of resilience and learning from such experiences.
Mindmap
Keywords
💡Backup dancer
💡Beetlejuice
💡Salesperson
💡Nostalgia
💡Embarrassing
💡Scariest story
💡Sales methodology
💡Fortune 50 company
💡Chief Sales Officer (CSO)
💡Sales tech
💡Account
Highlights
Jen's personal encounter with a difficult stakeholder who ultimately deemed her the worst at sales and berated her.
The stakeholder's harsh criticism led to Jen being threatened with termination by her boss after the stakeholder's complaint.
Jen's experience of emotional distress during the phone call where she was berated, showcasing the human side of professional challenges.
Will's initial struggles in sales and his decision to invest in self-improvement by purchasing a book from a renowned salesperson.
Will's transformation after immersing himself in sales knowledge, leading to a new job and positive coaching experiences.
The high-stakes sales opportunity involving a significant sum of money and the complexities it entailed.
The unexpected twist where the sales trainer's resistance to using the sales tech tool led to a dramatic fallout within their organization.
The strategic approach Will took by directly reaching out to the sales trainer, leveraging the trainer's own advice for engagement.
The repercussions of Will's actions, which included the firing of the chief sales officer and a strong rebuke from the sales trainer's organization.
The valuable lesson learned by both Jen and Will about the potential consequences of bypassing the chain of command in a sales context.
The audience's role in determining the 'scariest' story based on the experiences shared by Jen and Will.
Jen's reflection on her story and its lasting impact on her professional behavior and decision-making.
Will's realization about the dangers of idolizing someone in the field and the unexpected negative outcomes that can result.
The shared vulnerability and emotional honesty between Jen and Will, which humanizes their professional experiences and makes them relatable.
The humor and camaraderie that lighten the mood of the discussion, despite the serious nature of the stories being shared.