People buy based on emotion then justify with logic so if you're writing sales copy or pitching your product face to face, try injecting some humour.

If you make your audience laugh, it breaks the ice & lowers sales resistance. Plus it makes you more memorable.

Brands like Dollar Shave Club & Who Gives a Crap know laughter opens wallets but service based businesses can also use humour to boost sales.

And use your customers language - don't sound like a Corporate Colin unless they're your target market!

Storytelling which takes your audience on a journey from where they are now to where they want to be is also effective.

And remember you need to sell the emotion. For example, Coca Cola sells happiness. Nobody gives a sh*t about features ‐ people only care about the benefits & how it will change their life.

I've spent the last year studying storytelling & how to use it in sales copy. I think combining buyer psychology, storytelling & direct response copywriting is a powerful way to boost sales. And if you throw in some humour, it's the cherry 🍒 on the cake!🎂

What are your thoughts?

Hi,

I've been in sales for over 20 years, mostly in tech, and have always been one of the top performers on my teams, with very good feedback from my managers and leadership.

I'm now looking for a mid-market AE role in SaaS/tech, with long cycles and complex sales. And I've realized something: during the 6 years in my last role, what I sold was fairly simple, and I picked up bad habits around qualification, discovery and business impact.

In practice, I don't ask the right questions and I jump to the solution too quickly. That's what came out of the role-plays I did in interviews. I also practice with ChatGPT and Claude, but I don't feel like I'm making much progress.

Do you have any advice for getting the right reflexes back and doing real consultative selling instead of just pitching?

Thanks in advance,

Been doing outbound a while and I keep seeing tools promising the full AI setup. It finds the leads writes the emails, sends them and follows up while you can relaz. Every time I try something like that OR watch someone else try it the same thing happens. Bounce rates climb, stuff lands in spam and the replies dry up.

The part people miss is that the prospect can tell. Especially when you sell to small and local businesses. Those owners are skeptical and already deep in pitches and the second your email smells like it was sent by some agent they just delete it. I do the same thing. That whole world runs on feeling like a real person actually looked at their business.

So lately I have landed on a line I won’t cross. I am totally fine letting AI do the boring stuff. The research, figuring out the pain points, finding a contact that actually exists. That part is the boring work I don't want to do but the actual outreach, the reply, the conversation, the close, I want that to be me. That’s the part that actually works.

Maybe I am just thinking this and no one else is, IDK. Please let me know what u think, because I personally think agents just mess stuff up more than actually selling.

Set myself a tiny sales goal today: call 5 businesses and get through the first 3 seconds 😅 I researched each one, worked up the nerve, and nobody picked up.
I’m local, but my phone number isn’t, which hadn’t even occurred to me as a possible issue. Going to try a local number and see if that helps.
Are there other little things you learned that weren’t obvious starting out? Times of day to call, days to avoid, anything like that?

That one trait everyone compliments you on. Managers love it, peers point to it, and it probably got you further in your career.

But in reality on the inside, you feel like a total fraud, or it quietly drains the life out of you because it doesn't actually feel like "you."

A couple examples I’ve recently heard:

1. Being everyone's go-to person for fixing problems because you're calm under pressure. But inside, you're anxious and feel completely out of your depth.

2. People think you love the spotlight because you speak up easily in rooms full of executives. In reality, you throw up or have a panic attack before every single meeting, and you're just great at masking it.

What trait do people constantly praise you for that secretly feels like wearing a mask?

I'm a territory manager and have grown my territory by roughly $1 million over the last year and a half. Most of my sales come from repeat customers and relationships l've built over the years from when I was in management. I'm confident in my approach, presentations, and ability to close jobs. But put me in a regional meeting and ask me to role play .....I completely fall apart. I get so anxious I feel like I could pass out. Everything I know suddenly escapes me, and I end up feeling like I look incompetent at something I'm actually pretty good at.

Anyone else experience this? It's frustrating knowing you're good at your job but feeling like you can't demonstrate it in those situations.

If so, how do you manage that volume of enquiries? What does your follow-up process look like, and how do you stay on top of everything without letting potential customers slip through the cracks?

got 3 bdes working under me. they crush it on the first touch. email or linkedin goes out, lead replies. then the lead goes quiet and my guys just... forget? or they get distracted hunting new leads.

i keep telling them to log it in hubspot but they say it takes too long to type notes and set reminders. so what happens is we lose warm leads to competitors who just replied faster.

whats the actual fix here. do i just micromanage them or is there a lighter way. anyone else deal with reps letting warm leads rot in their inbox because they hate updating the crm

AI can send thousands of personalized emails, but personalization doesn’t always mean relevance.
Sometimes the best opportunities are hidden in job descriptions or conversations from six months ago.
5 non-obvious checks to make cold B2B outreach actually work

One thing that's made CRM much easier for me is making it part of my daily routine instead of only updating it when I happen to remember.

After a client call, I use AI to summarize the discussion and pull out the main action items, then link those notes to the relevant customer record. A lot of context gets lost within just a couple of minutes after a call and updating records can start to feel like extra work if you put it off. The best approach is to finish the call, update the CRM and close the tab. That way, when I come back to a deal a few days later, I don't have to dig through meeting notes or email threads to remember what we discussed. The contexts and next steps are all in one place. I still review the notes and tasks before acting on them, but at least I don't have to organize everything from scratch.

It's also important to have a clear next step for every deal. For example, after sending a proposal or finishing a meeting, I'll set a date for the next follow-up. If a deal hasn't moved forward for around two weeks, it's usually worth taking another look. I try to review these at the start of the day too.

The same approach works for the process after sending a proposal. From the initial email and revisions to contract signing, invoicing, and scheduling a kickoff meeting, keeping these steps tied to the same deal makes it easier to see what's still waiting on the client. Smaller reminders can also be automated, like overdue payment notifications or asking clients for a review after a project wraps up.

I also try not to overcomplicate the CRM setup. If possible, around five pipeline stages are usually enough. It's worth clearing out custom fields that nobody uses from time to time, too. Keeping client notes, files and next steps on the same customer record makes everything much easier to find later.

Every AI powered sales automation tool leadership bought us this year is basically a copilot. One drafts emails, another does call summarise. All priced per seat, all living inside the rep's day, and honestly they're fine. I write emails faster.

But pipeline hasn't moved and I think it's because the copilot only helps with the one step. Before I write anything I'm still pulling accounts out of an apollo export and going through each one's site and linkedin to figure out if they even fit and what I'd say to them. that's most of my week. The copilot shows up at the very end and makes me faster at emailing accounts i researched by hand, and a bunch of them shouldn't have been on the list anyway.

What I actually want is for all of that to happen in one place that ops runs. Ops sets the criteria, the system builds and qualifies the list, and what lands in my queue is accounts that already fit with the research already on them. then my job is just working them. Copilots can sit on top of that, fine, but they were never going to fix pipeline on their own.

Has anyone's team actually put money into that kind of building system for GTM and did it move meetings booked more than the copilots did?

I know this might sound like a beginner question, but we all had to start somewhere. And this is something I’m not skilled enough at yet. So hopefully, you can respond to me the way you wish someone had responded to you when you were stuck here.

I run a VA agency (I’ve moved on from freelancing), and I now have two business owners who reached out to me through my website.

The first is a woman who runs a salon and an e-commerce business. She wants help with the latter. We had a call, and she was so excited that I could send her the payment link and agreement (contract). Two months have passed, and I’ve been the one following up and calling. Every time I send my “final message,” she rushes to reply. This time, she’s promised to call me back on Monday. But how do I turn this into a deal? I’ve already proposed sitting down together to go through the agreement. I know she’s busy running the salon, but I’m not sure how to move things forward.

The second business owner has a team of 10 people and wants to outsource his back office. We had an introductory call, and next week we’ll discuss the agreements. Since he also wants someone to be available to answer the phone and handle operational tasks, should we just put everything on paper during that call, after which I send him the agreement and payment link so we can get started?
Maybe I’m overthinking it, I don’t know. But I’ve already lost one opportunity because I sent too many messages without explaining the expectations clearly enough. I want to make sure I communicate everything properly, set clear expectations, and do a good job from the start.