🏆 [Winner Announced] May Competition: What’s a sales mistake you made that taught you something valuable?

I love this topic as I always try to look at “failures” as opportunities to learn and do something better. I won’t start the conversation off with my own (yet), but I do want to tag some people in here that I think might have some great insight: ​@fernanda.nascimento, ​@Ryotaro Shingu, ​@zain.nazeer09, ​@Arun Kumar V 

​@Kelly_Program Manager Thanks for inviting me to colaborate! To be very honest to you, I always start a sales conversation thinking about the discount I can offer to the client :-O 
I know it is a big mistake and work hard to control myself… but my instincts keep teasing me all the time. Is that a sort of desease or does someone else “suffers” like me: :-D

I have perfect example, from my past:
A few years before ChatGPT existed, we were running outbound for a major AI software vendor in the MEA region, mostly in Dubai. The face of the campaign was a female AI professor, which we figured was a real asset in that market.

Because this was a big enterprise client, every lead had to be reviewed and approved before any message went out, and in corporate-land that means Excel. So we exported the Sales Nav list and from then on all we had were first name, last name and job title.

I'd built what I thought was clever segmentation. Locals got a formal pitch, male expats got an extended one, and female expats got something more personal, leaning into shared identity. Same gender, same expat status, same niche industry. Conversions were really good.

Then a reply landed. "Your AI must be pretty weak if it mistook me for a woman."

Turns out Simone is a man's name in Italy. A few messages later, same thing happened with a Sasha.

What bugged me afterwards is that inside Sales Navigator I'd have caught it in two seconds. There's a photo right next to the name. The minute we exported to Excel that context was gone. Simone could be anyone, Sasha could be anyone, and we were sending the female-coded message on autopilot. And by "autopilot" I mean an intern copy-pasting from Excel and hitting send.

The professor laughed it off, she decided to keep the conversation going, and we actually closed a serious deal with Simone in the end. So thanks Simone, I guess.

What I took from it: when you pull data out of LinkedIn into a spreadsheet for review, you also strip out half of what was making personalization possible. And names really don't translate across borders.

My biggest mistake was leaning too hard into my developer brain early on. I once sent a prospective client a massive, 10-page technical audit of their Shopify store's speed issues, thinking the data would do the selling for me.

The learning? I realized I was selling a 'fix' to someone who hadn't even agreed they had a problem yet. It was overwhelming, not helpful. Now, I use Sales Navigator to find the right time to talk, but I lead with a simple question about their goals, not a list of their technical flaws. Data backs up the deal, but empathy opens the door.

​@fernanda.nascimento I get you!! Habits are hard to break, and I’m sure you’re not alone in this. The good news is that you have spotted it and that you’re aware of it, which is half the battle 😄 anyone else struggling with this?

Thank you for sharing this story, ​@rafal! This is proof that context is always essential, and it makes a big difference when we don’t have access to that. 

I’m sure Simone still remembers that email. And congrats for closing the deal! 😆

This is a fantastic learning, ​@harishreddygudi! In ​@rafal’s example we see how much context is important, but timing is also essential. The right solution at the wrong time isn’t going to work. 

Sales Navigator’s signals are invaluable, as they help identify the right moment to reach out to a prospect.

I like the idea of asking them about their goals, as that allows you to tailor the message even better, and align on common purpose!

I really miss having a gender filter in Sales Navigator. I imagine that technically this isn’t a problem, but the challenge would likely lie in communication and PR. Should the user be the one to decide how many genders there should be—knowing that any choice will be criticized by some group—or should the system handle it?

Nevertheless, it would be very helpful when working in markets where the language requires writing differently to women than to men.

Ensure your InMails are personalized! You are more likely to receive a response.

Hi ​@rafal, I understand the difficulties of having to tailor the language according to pronouns - my mother tongue is Italian, and the issue would be similar. 

I would encourage you to submit your filter suggestion as a product idea here, as our team will review and assess whether it’s possible to implement it. Currently, when viewing a lead page in Sales Navigator, user pronouns of choice are visible, if the user chose them. However, filtering by pronouns is not possible. 

I really encourage you to submit this idea!

Hi ​@prwong, thank you for sharing this with us! I agree, messages need to be relevant or personalised to make a real impact. Did you see a big difference between personalizing and not personalizing in your results? 

Welcome to the Community, ​@ricardobarboza1 ​@aknox8781 ​@Jamusheng ​@Praveen Varma ​@Xia! 👋

I’d love to hear your stories on this. What’s a sales mistake you made that taught you something valuable?

I have probably made quite a few mistakes throughout my career, but one of the most valuable lessons I learned came from arriving at a meeting and presenting a proposal for a completely different product than the one the client had requested. What was the reason? Too much work, stress, and, obviously, not paying enough attention to the client. The lesson is clear: no matter how senior or experienced you are, never attend a meeting without being properly prepared.

​@david19 This can happen to anyone under stressful conditions and with limited time available. The good thing is, as you mentioned, that these mistakes teach us valuable lessons - they usually only happen once! 😄

Your experience reminds us how important it is to set aside time in our calendar to prepare for meetings and events. Thanks for sharing this with us, it’s really important to hear learning stories from others and learn together!

​@Francesca_Community Manager 

I love this one because it highlights an experience I had this week. In sales, one of the worst things you can do is send information when they ask you to send information without a meeting commitment. I’ve been told that when you practice this, it kills the deal before you even have a chance to validate your offer. Even my coaches, who are top sales trainers, have told me this is a fatal blow to having your offer considered.

Well, as they always say, everyone responds differently, and while what these coaches teach day in and day out is mostly true, it’s not always how the real world operates.

Recently, a 5-star review generated highly qualified business leads.

I had the opportunity to meet the decision-maker via Zoom 2 weeks ago. After the initial meeting, the decision maker asked me to send him a proposal. What do the sales gurus teach? Don’t send a proposal without getting a meeting commitment, and don’t give it to them until the day of the meeting. He mentioned he would have a meeting with the other company stakeholders and wanted to share my proposal with them before committing to another meeting. Sales gurus say, “Don’t do it”.

The mistake: I sent it anyway. I asked him if we could schedule a follow-up meeting with him and the other decision makers. He agreed to put the meeting on the calendar and said he would send me the email addresses of the other decision-makers.

The result: He never sent me the emails despite my follow-up.

The second result: He sent an email the day before stating that he would not be able to attend the meeting because an important project had come up, and he would be away until mid-June.

My reaction: I virtually slapped myself.

My 2nd reaction: I explained to him that I understood he would not be available but that if he could make time to meet with me, I would like to go over the proposal and the stages of the sales process I had laid out in my proposal to see if we can come down to a price margin that might make more sense with his current situation since he said my price was too high. He did not have the budget to move forward with it.

His reaction: He agreed to meet despite being in a rush to leave for the airport.

The result: He agreed to meet with my partner and I to address his concerns. He was at the airport when he took the meeting.

The outcome: He said that the proposal was very impressive and that he had never seen anyone lay out the action plan in the way I did. He said he was so impressed, he had another project he wanted me to work on. It turns out his wife is also trying to start a business and has no idea how to launch her marketing campaign. He went on further to say that the way I laid out the proposal and highlighted each stage of my offer was so well written that even his wife understood why she should also work with me to launch her marketing campaign.

He went on to say that his partners, who are used to the old way of doing things, were very impressed with my proposal. They clearly understood the game plan, saw the value it offered, and recognized its potential for future business growth.

Additional thoughts: I was angry and upset with myself for breaking the mode of operation my sales coach had outlined more than once. This deal started with him looking to get my help marketing his business. What I didn’t know is that he had a business he hadn’t mentioned previously that has been operating for over 35 years. He mentioned he needed help with both businesses, but the sales sin I committed led to a new deal that came out of simply sending out my proposal. He mentioned the price was more than he had initially expected to invest, but after reviewing my proposal, he could see why each step was a logical path to the next.

What was only one deal I was hoping to land has now become three potential deals that will have a massive positive impact if everything goes according to plan. We have a follow-up meeting scheduled for the end of June, so I can meet his wife and get more details about her business.

The moral of the lesson: Sometimes doing things the right way leads to a massive disappointment, and in some cases, doing things the way you’ve been told not to do it opens doors to new opportunities. Applying cookie-cutter approaches can sometimes crash deals.

Being in business comes with all kinds of risks, but if you don’t take risks, you’ll never know what could be. If anything, trying to land a deal is a rollercoaster ride. Some will, some won’t, but someone out there needs to hear from you. Find a way to work with people the way they work. Meet them where they are. You might just land the biggest deal of your lifetime.

Love this story, ​@Damien Orozco! Sometimes, as you've pointed out, reality and theory are different. What’s important is that you managed to turn the complex situation into an opportunity (actually - into several opportunities!).

Frameworks and official guidance are always helpful, but your instincts and empathy matter too. Ultimately, it appears the high quality of your proposal made a significant difference and was the deciding factor for your prospect and his wife. Congratulations on the excellent work!! 💪

Thank you all for sharing your stories. This why this Community is special - what we learn from each other is invaluable!

🥁🥁🥁 It’s time to select our winner for May! 🥁🥁🥁

It’s you ​@Damien Orozco! Thank you for sharing your story with us - it’s inspiring! ✨

Congratulations! 👏

Congrats ​@Damien Orozco 

Wow, I am honestly blown away! Thank you so much. I felt this story would really resonate with the community because it highlights how real-world experience often challenges traditional sales frameworks. Sometimes, going against the "common advice" is exactly what you need to do to open doors. 

I definitely didn't expect to win, so this has truly made my day—happy tears all around! 🥲😃🌞🥳 Thank you to infinity for this recognition!

Thanks ​@david19 😃