u/GrayBeard916

I have 15 years of sales experience. Started in retail back then, moved to SaaS, and now I run a team. Throughout those years, I've been the bottom rep, the top rep, and everything in between.

If I could go back in time, here are the things that I would give my younger self (just sharing the knowledge I've gained all those years to everyone out there):

1. Shut up more.

For me, this is the #1 skill and the hardest one to learn as well. The problem with new reps is that they 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?" It feels boring, cold, and even robotic. 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, I highly recommend you 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. Actually care more about the customer than the other reps.

Sounds soft, but it's not. Most reps don't actually care about the customer's problem, as they're more focused on 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, that confident reps were just built different. It's not. They're 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. You get good by doing them.

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. Mindset by Carol Dweck also stuck with me even though it 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 sell to finance people, learn finance. If you sell to marketers, understand marketing. If you sell to CFOs, learn how CFOs think. Basically, learn your buyer's world. 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 so early. Start diagnosing instead.

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 you think you should.

Most deals don't die from a no. They just die down because nobody followed up enough. 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.

People underestimate how draining sales can be physically and mentally.

It's both a physical and a mental 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?

I have 15 years of sales experience. Started in retail back then, moved to SaaS, and now I run a team. Throughout those years, I've been the bottom rep, the top rep, and everything in between.

If I could go back in time, here are the things that I would give my younger self:

1. Shut up more.

For me, this is the #1 skill and the hardest one to learn as well. The problem with new reps is that they 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?" It feels boring, cold, and even robotic. 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, I highly recommend you 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. Actually care more about the customer than the other reps.

Sounds soft, but it's not. Most reps don't actually care about the customer's problem, as they're more focused on 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, that confident reps were just built different. It's not. They're 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. You get good by doing them.

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. Mindset by Carol Dweck also stuck with me even though it 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 sell to finance people, learn finance. If you sell to marketers, understand marketing. If you sell to CFOs, learn how CFOs think. Basically, learn your buyer's world. 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 so early. Start diagnosing instead.

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 you think you should.

Most deals don't die from a no. They just die down because nobody followed up enough. 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.

People underestimate how draining sales can be physically and mentally.

It's both a physical and a mental 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?

Pretty sure I'm not the only one. As time goes by, I realized that I'm weirldy selective with gaming in my 30s. Back then I can boot up anything immediately as long as a game looked cool. Now, I catch myself doing this thing where I keep telling myself that I should wait until I can really enjoy a game.

The result is me having a massive list of backlogs and games sitting untouched simply because I'm waiting for that perfect mood so I can start playing them. Meanwhile, I still somehow kept on replaying games I've already beaten several times because I'm just too tired to commit to something new.

Right now, the games that I "saved" for later are the Cyberpunk expansion, Starfield, Elden Ring DLC, and some indie games that lots of people swear by.

I'm sure a lot of you do the same too. Which games are this for you?

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?