What Not To Do Tips
Home of the F#%k Up Friday’s!
Come for the cringe-worthy moments and stay for the tips.
Latest Tips
F#%k Up Friday
Friday, September 13, 2024
In this post, I share my experience as a new CSM when I mistakenly interpreted the last-minute involvement of senior leaders in a renewal as a positive sign, only to discover that my lack of thorough discovery and understanding of their evolving needs nearly derailed the renewal process.
F#%k Up Friday
Friday, September 06, 2024
In this post, I recount a pivotal moment in my sales career when I mistakenly sent a generic proposal, failing to articulate the personalized value of my solution, which taught me that effective proposals must consistently reflect the client’s unique needs and business goals to avoid losing momentum in the deal.
F#%k Up Friday
Friday, August 09, 2024
In this post, I share a story from my time as a CSM when a stakeholder management slip-up led to an angry confrontation with my exec sponsor, teaching me the importance of multi-threading my Success Plans and ensuring access to multiple contacts within a client organization to maintain momentum during absences.
F#%k Up Friday
Friday, August 02, 2024
I reflect on my misjudgment of a supposed Champion, realizing too late that while I focused on the VP of Global Sales, it was the Director of ENT Sales who truly held the influence and could have expedited our deal had I engaged with multiple stakeholders from the start.
F#%k Up Friday
Saturday, July 27, 2024
In this F@&k Up Friday post, I highlight a common mistake among reps: the failure to establish the cost of inaction, as many get so caught up in showcasing flashy AI features that they neglect to tie their solution back to the client’s pressing problems and the importance of addressing them immediately.
F#%k Up Friday
Friday, July 19, 2024
In this post, I share my early mistakes with Mutual Action Plans (MAPs)—focusing too much on tracking activities rather than aligning them with the buyer’s success criteria and making the process seller-centric rather than buyer-led—and how I transformed my approach to turn from a mediocre rep into a top performer.
F#%k Up Friday
Friday, June 28, 2024
As a sales team leader, I learned the hard way that relying on optimistic assumptions and surface-level metrics can lead to missed opportunities, as several expected cross-sell deals fell through due to overlooked risks, prompting me to implement a more rigorous forecasting process.
F#%k Up Friday
Friday, June 14, 2024
I’ve always struggled with self-promotion, but as a business owner selling my knowledge and time, I realized I needed to get comfortable sharing my accomplishments—especially after creating a course and realizing that new customers had no idea who I was or what I’d achieved.
F#%k Up Friday
Friday, May 31, 2024
As an AE, I learned the hard way that failing to tie our solution to an immediate business priority or addressing the ‘Why Now’ with each stakeholder led to a promising deal being put on hold, teaching me to always create a sense of urgency to avoid losing out to the status quo.
F#%k Up Friday
Friday, May 24, 2024
Early in my AE days, I learned the hard way that relying on weak, generic “personalization” in emails, like referencing a prospect’s university or a quote, not only backfires but can damage credibility, prompting me to shift to genuine, problem-focused personalization that dramatically improved my response rates.
F#%k Up Friday
Friday, May 03, 2024
I highlight the common industry mistake of turning discovery calls into interrogations rather than conversations, emphasizing the importance of curiosity, active listening, and not rigidly following qualification frameworks at the expense of the client’s experience.
F#%k Up Friday
Friday, April 12, 2024
In today’s F@&k Up Friday, I’m owning up to my past mistake of sending overly long prospecting and outreach emails, realizing that concise, targeted messaging focused on one hypothesis and problem statement at a time is far more effective than trying to include everything at once.
F#%k Up Friday
Friday, April 05, 2024
I once misjudged my sales team’s pipeline by focusing too much on a few large deals, which led us to miss the quarter due to a lack of volume in smaller, winnable deals, teaching me to balance big deals with risk, volume, and pipeline quality to ensure consistent success.
F#%k Up Friday
Friday, March 22, 2024
I mishandled a renewal by relying too much on a single point of contact, failing to build relationships with key stakeholders and test my champion’s influence, but after scrambling with a save plan and leveraging internal resources, we managed to close the renewal and secure an expansion deal.