r/salestechniques

15 years in sales. Here are the only tips I'd give a younger me.

I've been in sales for 15 years. Started in retail, moved to SaaS, now I run a team. I've been the bottom rep, the top rep, and everything in between. Here's what actually moved the needle for me.

1. Shut up more.

This is the #1 skill. New reps talk too much because silence feels scary. But the person who's quiet usually wins. Ask a question, then close your mouth. Let them fill the space. They'll tell you exactly what they need if you let them.

2. Ask better questions, not more questions.

Most reps fire off questions like a checklist. "What's your budget? What's your timeline? Who's the decision maker?" Boring. Cold. The buyer feels like a form.

Better questions sound like: "What made you start looking now?" "What happens if this doesn't get fixed?" "What's been tried before that didn't work?"

These get you the real story. Real story = real deal.

If you want to get good at this fast, read SPIN Selling by Neil Rackham. It's old, it's dry, but it's the bible. Also Never Split the Difference by Chris Voss for the psychology side, the chapter on calibrated questions alone is worth the book.

3. Care more than the other reps.

Sounds soft. It's not. Most reps don't actually care about the customer's problem, they care about closing. Buyers can smell this from a mile away.

If you genuinely want to help, even when it means telling them your product isn't the right fit, you'll build a reputation that pays you back for years. I've gotten referrals from deals I LOST because I was honest.

The book that changed how I thought about this was To Sell Is Human by Daniel Pink. Also worth listening to The Advanced Selling Podcast and 30 Minutes to President's Club, both have full episodes on this. Bryan Burkhardt's stuff on LinkedIn is also genuinely good if you can ignore the algorithm-bait posts.

4. Confidence comes from reps, not affirmations.

I used to think confidence was a personality trait. It's not. It's just the result of doing something a thousand times. The 10th cold call is terrifying. The 1000th one is boring. Just do the reps.

If you want to speed up the learning curve in between reps, Fanatical Prospecting by Jeb Blount is the most underrated book in sales. Also The Psychology of Selling by Brian Tracy if you want the classic. For mindset stuff, Mindset by Carol Dweck isn't a sales book but every top rep I know has read it.

5. Learn how the buyer's business actually works.

If you're selling to CFOs, learn how CFOs think. Read their reports. Listen to their podcasts. Understand what their day looks like. The reps who can talk like a peer instead of a vendor get treated like one.

I do most of my learning on commutes now. Been using BeFreed for the last few months and it's been useful for this kind of cross-domain stuff. You input your current level, your goal, and how much time you have, it evaluates you, then builds a personalized learning path from the best sources, sales books, psychology research, expert talks, finance content, whatever fits your goal. You can pick the voice and length too, I have mine on the humorous style at 15 mins because dry finance content is brutal otherwise. Replaced most of my podcast listening at this point.

6. Stop pitching. Start diagnosing.

Doctors don't pitch surgery in the first 30 seconds. They ask where it hurts. Sales is the same. If you're pitching before you've diagnosed, you're guessing. And guessing loses to the rep who actually understood the problem.

7. Follow up more than feels reasonable.

Most deals don't die from a no. They die from silence. Follow up 3x more than you think is appropriate. Half my closed deals came from a follow up that felt awkward to send.

8. Take care of your body.

Sales is a physical job. You're talking all day, riding emotional waves, dealing with rejection. If you're tired, hungover, or stressed, your numbers will show it. Sleep, lift, walk. Boring advice. Works anyway.

TLDR: shut up, ask better questions, care, do the reps, learn your buyer's world, diagnose don't pitch, follow up more, take care of your body. That's the whole thing.

What would y'all add?

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u/GrayBeard916 — 3 days ago

Sales Veteran - Sales Advice (long story, but good advice)

Hi everyone,

This is a long story, but I hope it helps some of you. I have been reading some posts and it reminded me of my first sales call on the phones, so here's my story and some tips on how to crush sales!

I started my 15 year career on the phones cold calling people to upgrade their phone plans. My first call was very embarrassing. The prospect picked up and I remember immediately hanging up on them. I was so nervous I wanted to leave... But I didn't.

I called them back and I got the sale on my first call. My commission was $3 for that sale and I was making $13/hr. So in my eyes, If I sold 10 per hour, I could make $43/hr. At 18, that's real money. So I started grinding. I quickly became the leading sales rep and also became obsessed with trying to break my previous record (I think I got like 50 sales in one day). My quota was 2 sales per hour.

Throughout the next 24 months, I landed random jobs (weight loss cold calling - WORST job ever, pretty much a scam so I quit), financing sales roles, cold calling as a contractor for startups, and even a marketing gig. Learned a lot but nothing lasted more than 3 months.

Eventually I moved on and got a job at a paper scanning company which I worked at for 4 years. I was put into another acquisition patch because people thought I had good energy and I was OK hearing "no". This time my salary was $60K a year and the OTE was $100K. That was serious money for me. I smashed my quota again but felt like it was quite a mission to make $100K salary, and the organization didn't approve any forward-thinking ideas that I put forward so I started to feel like I was 'living in someone else's shoes'. Every $1M sale I landed, I felt like it could have been mine if I started my own company, since this company didn't seem to have much of a strong brand, it was purely relationship selling. (my quota was $4M)

Trying my luck, I decided to start a company myself focused on fintech. I managed to raise some capital and brought on some technical people while I focused on sales. This was truly a humbling experience as you literally are life-or-death. You have no brand. Your outcome/attendance at conferences is 100% your warm leads, there is no existing data, no fancy tools, no manager, nothing. It's just you, your motivation and the phone waiting to be dialed. I managed to land a few enterprise clients, and kept building the product further and further. The enterprise clients that we landed unfortunately didn't pay the bills, and so I started feeling like a failure.

I needed something to raise up my self-worth and feel like I've accomplished something, so I started applying at the big-3 tech firms, Microsoft, Google, and AWS.

After 100 rejections, I finally got in! Working at Microsoft was a dream of mine, and I was ready to devote the next decade of my life. I was making $250K a year with a bunch of benefits on top of that. I felt like I had bank finally. I was at the pinnacle of technology working alongside the brightest people, biggest companies and felt great telling people where I worked. I surpassed my quota but strangely felt like it was way less challenging than other sales organizations I've been at, definitely my easier than own company... and after a few years there, I decided to quit.

At Microsoft, I ended up in a role that didn't involve hunting... that didn't have a quota I could influence. I didn't feel challenged enough and I realized that I was born for real sales. I ended up starting a few projects focused on sales, AI, and consulting.

If you've lasted this long, let's talk about how I managed to become the #1 sales person in every organization I've worked at, and even land a job at Microsoft.

First: Get any narrative out of your head that you aren't good at sales. My first call was a disaster. I literally hung up on the client. If I accepted that I wasn't good at sales then I wouldn't have gotten here today. You don't need to be perfect, but you need to believe in yourself, even after failure! What you have right now is probably enough to impress someone!! Stop over building and over thinking, just talk about what you have!

Second: Have fun with it. What really helped me is having fun little competitions with myself or a peer I enjoy being around. Being competitive is underrated and I think it builds confidence and drive, despite how sensitive people have become!

Third: Spend time understanding your product. I've met quite a few sales people that have no idea what they are selling. This voids the entire #2 rule because you can't have fun if you feel stressed about technical questions. If you take the job and you don't have passion in what you're selling, then go to the store/online, and BECOME in love with the product. No excuses here. You need to love what you do or you'll never do great things in sales. Even if you are 18 - 24, this rule should apply (I started selling phone plans) because even selling phones, I remember spending my free time searching up phone comparisons! I became quite a nerd around mobility. you need the passion. Clients will buy from you much easier if they see you love what you do.

Fourth: Passion. Disclaimer: I understand there might be activity requirements but hear me out. I personally NEVER do cold/warm prospecting when I'm feeling tired/groggy. A lead is extremely valuable. Even if you're using AI to outreach, try to put your full passionate effort behind drafting the script, email, or even having the meeting itself. People buy from people. Unless you are Anthropic or OpenAI, you need people to like you. This is where I highly recommend you follow rule #1-2-3. If you come off as confident, passionate, knowledgeable and intentional, people nowadays respect less small talk, more transparency. The "Sales Guy" mentality is dead. Guess what? Your client knows they are in a position of power. They know you want to make the sale from them. So what? Show them you want the sale. Treat them like an Enterprise client. Ask good questions and build rapport with them by being yourself! Thats what people want nowadays!! Everyone is tired of the passion-lacking sales guy who is surface level and probably hates their life because they didn't do what they love.

Five: Use all the tools you want. Research all you want. These things help, they do. But PLEASE, just get on the phone. If you do not work at an established company, or if you have a startup, guess what!? NOBODY is going to do the shitty part for you (cold calling). Its YOU and only YOU! I will give tips on how to succeed cold prospecting below.

5.1: AI Agents. I didn't have these 10 years ago, but this will save you A LOT of time when prospecting. Use Claude or OpenAI to help you curate a list of potential ICPs. You can work with it to set up a great initial outreach email. I suggest spending 1hr+ drafting a solid email with your AI. Don't be lazy here. Read it out loud and make sure it sounds human and not AI slop.

5.2: Put yourself in their shoes. If you were in your ICP's shoes, and you got a random email, how would you feel? If your email doesn't stimulate some sort of emotional (or logical) response, then its a crappy email/outreach. This is where the greats stand out. Treat every outreach/lead like they are gold. A single client can make your entire business.

5.3: Start low. Despite what people say, aiming for VPs, CEOs, Directors, etc, almost never works. They get emails every single day. Your email domain might not even pass their email firewall or they'll flag you as spam and kill future opportunities. If you are serious about getting in touch with them, call the receptionist and show them your passion. Show them you really want to speak with that person because you have an amazing product that can (this is your explanation). You just need 10 minutes with them. Your passion will be contagious and people will want to help you. Which leads into my next point.

5.4: Trust. Trust by far is the most important thing you need to gain with any prospect. They need to believe in you, your product, your company's financial well-being, your security, your ability to deliver, everything. Trust is the magic 'X factor' in sales. But Trust doesn't always have to start with your target customer. Trust can start with the receptionist, who has Trust with your target. So you're leveraging trust between two parties which essentially gives you "temporary trust" because you've been referred into a trusted circle. You need to continuously maintain trust with your prospects and clients. We all know legal kills deals, well so does mistrust. The more someone digs into nitty-gritty details, it's likely they don't fully trust you and they'll find something (likely not harmful, but enough to kill a deal). Focus on listening to your client's needs, be yourself, be transparent, and sell your passion. That's how you maintain trust.

5.5 I like you, but I won't pay. In my startup days, this was a grim reality. I was able to get many clients booked in for meetings but people kept treating what we were offering as if it were just a "nice to have", not a "need to have". I quickly realized that I wasn't selling, I was being desperate. The Apple phone was never a "need to have". In fact, nothing in this world is a "need to have". No matter what any VC tells you, any advisor tells you, a coach, etc, nothing in this world is important, except for your passion and the customer's needs. Almost every single company I've worked at has the ability to create a custom product for their client's needs. For example, your product has 10 screws, but the client mentioned they have a hard requirement for 9 screws. You have three options here: End the call, mark as Lost. Convince them 10 screws are better than 9 screws. Or, the expert option, ask them why they need 9 screws. The WHY 9 screws might be your biggest opportunity you've ever landed. That single difference in screws may be a massive opportunity to develop something even larger and more custom for their enterprise. It might touch their call centers, it could touch their marketing, their infrastructure, etc. You need to genuinely be passionate enough that you WANT to learn why 9 screws is so important to them. They want to tell you. They know you want their business. They know you want the sale. Be curious and passionate!

6: Ask for their personal cell phones: I win deals by being available. Anyone who thinks they are too busy to pick up their clients calls are not great sales people. Consider sales like dating or friendships. A great sales person will always take initiative and make the other person feel like it's OK to call each other at any time. This single strategy has helped me close million dollar deals because nobody wants to be "corporate mode" all the time. We're tired of Zoom calls. Teams calls, emails. We just want to chat on the phone, even if its 5 minutes for a quick question. Make them feel comfortable and also, try call them out of the blue to ask a "question question". They'll appreciate your confidence.

Alright, my DMs are open if anyone wants additional help.

Believe in yourself!!

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How do you Handle Rejection?

I am not a sales person, I am into the Tech always but with time I understand that building is not enough & I have to start doing the outreach - I tried Cold emails & I was not getting the good results

So I shifted towards the cold Calls - did research on how to purchase International Local no., buy the subscription & Tonight i started calling the business !

I did approx 13 Calls tonight first time - it might sound small but yeah for the first time 13 feels too big however every time the receptionist picked the call & said Dr is not available right now - he/she is with the Patient - either they told me to email the Dr or tell her and she will forward the message

So I tried using the Claude method saying that what time is best when doctors are available or other things - but in each time the same response either you email the Dr or tell her she will forward

When I told her - for what I am calling - she will hang up, or remove the no. And even sometimes rude!

I don't have the habit of such things - and it's just 13 calls tonight - expectations were at least 20

So I want your help in this - how u handle such rude, hangup and how you control your brain when it starts reacting so differently - feels bad to myself ?

I know even to close 1 deal - I need at least 200 Dials

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u/Existing_Round9756 — 3 days ago

why do founders keep hiring expensive sales people to fix a problem that the right tool would have prevented?

This is an expensive pattern startups follow.

Year one: founder does outreach manually, LinkedIn messages, cold emails, a spreadsheet of prospects. tells themselves they'll build a proper system when things pick up. things pick up but the system never gets built

Year two: the spreadsheet is a mess, follow ups are slipping, good leads are going cold because nobody caught them at the right moment. they hire an SDR to fix it

Year three: the SDR is busy but the pipeline quality is still inconsistent, some leads convert, most don't, nobody really knows why. so they hire a sales consultant or a head of sales to figure out what's broken

that person spends the first few months not doing what they were hired for. they're trying to understand why outreach isn't converting when the real problem was never the outreach itself

there's a difference between someone who is vaguely aware of your product and someone who is actively feeling the pain you solve right now, most founders are spending all their time and money on the first group and wondering why nothing is closing

the sequence matters

you need to know who has intent before you spend anything on reaching them. an SDR without intent signals is just sending volume into a void. a sales consultant without clean targeting data is just expensive opinions

most early stage founders don't need a bigger sales team, they need to know which people in their market are already raising their hand right now

so genuinely curious, what are people actually using to figure out who has real buying intent before they reach out

because the tool that changes everything isn't the impressive sounding one, it's the boring one that just makes sure you're talking to the right person at the right moment

Has no one figured out a tool for this?

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u/Ok-Credit618 — 9 hours ago
▲ 14 r/salestechniques+1 crossposts

We're a third of the way into 2026 and I want to know how LinkedIn is holding up for everyone as an actual channel.

A few things I'm seeing on my end:

  • Organic reach feels noticeably softer than 12 months ago, even on posts that used to bang
  • DMs land less often (more "Accept" without reply, more silent reads)
  • The feed is heavier on AI-generated/templated content, which I think is training people to scroll past faster
  • Sales Navigator searches surface the same overworked ICP everyone else is hitting

What are you seeing on your end?

  1. Is your organic reach up, flat, or down vs. last year?
  2. Are you still getting inbound from posts, or has it shifted to DMs / outbound / events / referrals?
  3. Anyone closed a real deal from LinkedIn in the last 60 days - what was the path (post → DM, comment → DM, cold connect, etc.)?
  4. What format is actually working for you right now. Text posts, carousels, video, newsletters, polls?
  5. If you've moved budget/time off LinkedIn, where did it go and is it working better?

Thanks!

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u/ShiftGood3066 — 6 days ago

Why Signal Based Prospecting Is Outperforming Traditional Cold Outreach in 2026

Lately I’ve been noticing that a lot of outbound still feels very volume driven.

Most workflows are built around static lead lists, enrichment tools, and sending as many emails as possible, but very little attention goes into timing or whether the prospect is actually showing intent right now.

What’s been interesting to me is how many buying signals people leave publicly every day through:

• Reddit discussions
• LinkedIn posts/comments
• Hiring activity
• Tool comparison questions
• Complaints about existing solutions
• Community conversations

I’ve been experimenting recently with tracking some of these signals before outreach instead of starting from random lead lists, and honestly the quality difference has been pretty noticeable.

Not even necessarily from “better personalization”, mostly from reaching people while they are already thinking about the problem.

A few things I noticed while testing this:

• Smaller targeted lists tend to perform better
• Timing matters more than message length
• Reddit is surprisingly strong for intent signals
• AI is way more useful for filtering/prioritizing than writing copy

Curious if anyone else here has been experimenting with more signal based prospecting lately.

Also putting together a short session where I’ll share some of the workflows and examples I’ve been testing if anyone’s interested.

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u/Low_Pea_951 — 3 days ago

How do experienced field sales reps decide which companies to visit first when they have a territory of thousands of SMBs and no data on any of them?

Junior sales rep here, I started three weeks ago selling packaging materials to food manufacturers and industrial producers. I got handed a list of 2,000 companies, a car, and a weekly visit quota.

The problem is I have no idea how to prioritize. I keep driving to places that turn out to be too small, already locked into a competitor, or just completely wrong for what we sell. I asked my manager how to decide and he said to use my instincts, not super helpful when you're three weeks in.

Most of these businesses have basically no online presence so looking them up before visiting tells me almost nothing. Is there a more systematic approach to prioritizing a territory when you have almost no data on the companies in it, or is this genuinely just something that comes with experience?

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u/yuuliiy — 1 day ago

What’s the most useful tool you use daily in sales?

me the most used tool/app in your sales workflow.
CRM, AI, automation, follow-up, anything
just write the one you use the most daily.

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u/Fit_Prune_6910 — 4 days ago

Need Help with Cold Calling

Hi guys, my background is in tech and AI, and I never really had any sales processes. I recently started an AI agency and have a list of numbers I need to cold call. I have created a sales script with AI and my intuition, but I am not sure if it is good to go. It would be of great help if someone would be open to a DM and give me a few tips.

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u/Akilesh10 — 3 days ago

I don't like my voice. What should I do?

My voice just sucks. Even when I'm not stressed, it doesn't sound very “manly”—even though I'm 28, I sound like an insecure little boy sometimes.

Recording myself revealed this unpleasant truth, and honestly, I don’t know what to do—it’s not just about pitch, speed, etc. My voice just doesn’t sound like it could sell anything.

Has anyone else had this happen, and what did you do about it

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u/gimmelord — 4 days ago
▲ 7 r/salestechniques+1 crossposts

In your experience, how do you handle high risk payment processor alternatives during the closing stage? Many sales reps face pushback when clients hit processor limitations, especially in certain industries. What strategies or scripts have worked best for you to keep deals moving without losing trust? Looking for practical B2B sales techniques here.

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u/Weary_Gift9342 — 5 days ago

Après beaucoup de recherche je peine à trouver un moyen vraiment efficace de prospecter dans mon domaine.

Je suis entrepreneur d’une société de multi services dans le domaine de la construction métallique, décoration métallique et petits travaux du bâtiment.

J’ai déjà envoyé pas mal de mails que j’ai trouvé sur internet. Restaurant, hôtel, collectivités, entreprises en tout genres…
Quelques retours positifs mais j’ai besoin de plus.

Surtout l’idéal serait d’avoir facilement une grosse quantité d’adresses mails afin d’augmenter les chances.

Je me demande aussi si il existe des outils avec l’IA pour faire ce genre de choses car remplir tout manuellement sur Excel prend un temps de dingue.

Utilisez-Vous des programmes/ logiciels pour ces démarches?

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u/AnnualPercentage6275 — 6 days ago