🏆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?