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It Happened on the Sales Floor-100 Sensational Stories About Sales Leadership Screw-Ups and Big-Wins

📢 Exciting News! 🎉 My audiobook "It Happened on the Sales Floor: 100 Sensational Stories About Sales Leadership Screw-Ups and Big Wins" is now available on Audible! 🎧📚

In this audiobook, I share 28 years of sales and sales leadership experience at tech startups. Learn from mentors, my countless mistakes, and the resilience that led to success in building sales teams. Topics covered include hiring, training, coaching, firing, sales processes, leadership challenges, and more.

This audiobook is an easy-to-read companion, not a heavy instruction manual. Pick it up with your morning coffee, read a couple of stories, and gain valuable takeaways for the day. I wish I had this book 20 years ago to avoid mistakes and achieve success quicker.

Get your copy on Audible and learn from my sales leadership mistakes: https://www.audible.com/pd/B0C6FRZ1MC/?source_code=AUDFPWS0223189MWT-BK-ACX0-353065&ref=acx_bty_BK_ACX0_353065_rh_us 🎧📖

#SalesLeadership #AudiobookRelease #SuccessStories

Author

IVP Paragons are hand-selected operating executives with unique skills and a willingness to advise IVP portfolio companies become enduring market leaders. Paragons are experts at their craft, have a desire to give back, and actively want to participate in the start-up community (anywhere from Series B to newly
public companies).

(Full Disclosure:  I do not work FOR IVP.  This is an advisory role for their portfolio companies)

Paragon Advisor

Trellis Research

Advisor

Schmoop, LLC

Managing Member

Wonderway

Boldr

SEON Fraud Fighters

Hirect App

Lensa

Helping leaders at early stage tech companies avoid mistakes in all aspects of growing their sales team | Advisor

8 startups, 3 liquidity events and 1000s of mistake but that has made me successful.

I love sharing my mistakes and learning lessons from over 25 years at pre-IPO tech companies.

You get experience, not inexperienced opinions.

Experience not Opinions

✅ 3 startups I’ve been with have had liquidity events (none fire sales)

✅ Helped build 3 businesses into Inc 500/Deloitte Fast 500 companies (that means fast revenue growth)

✅ Built sales teams at 8 Startups since 1997

✅ Built teams of 30 salespeople - 550 salespeople with GREAT gross margins

✅ Built multiple Inside Sales, SDR/BDR, Account Management and Enterprise Sales teams.

✅ Been in Sales Leadership since 1997

✅ Started 3 of my own businesses (Recruiting, Advising, Real Estate)

✅ Named to the AA-ISP Top 25 Most Influential Inside Sales Professionals 6 years in a row

✅ Made lots and lots of mistakes

Check out the recommendations section below to read what other people have said about me. 👇

When I became a first-time VP of Sales, I made a lot of mistakes. Here are the 7 biggest ones that cost me dearly:

1/ I didn’t manage up. Founders don’t have all the answers, and it’s okay to challenge them respectfully. It makes them better and your life much better too.

2/ I obsessed over results and ignored the process and inputs. But results without knowing how you got there and how to repeat them are useless.

3/ I didn’t lean on mentors. Your ego doesn’t matter—getting it right does. I figured they were paying me so much, I better not ask for mentors/advisors. Wrong.

4/ I didn’t create a structured interview process. Trusting my gut created a lot of mis-hires, that resulted in firing reps. That's not fun for anybody.

5/ I thought I could do it all—like configuring CRMs and building a sales process. I should’ve enlisted the help of a RevOps team instead.

6/ I used off-the-shelf sales processes, which rarely fit my team’s needs. It's great to continually improve your team but customize what you hear/read before implementing.

7/ I kept my mouth shut when I saw problems in non-sales teams. Wrong move. A VP’s job is to look out for the whole company. See something, say something.

If you’re making any of these mistakes, stop now. It’ll save you a lot of time, money, and stress.

And trust me—it’ll make you a better leader. 😊

PS: If you found this post useful - you might like my course on Hiring Salespeople.

I'll share my proven methodologies and strategies to find and hire your next superstar AEs.

The link is in the first comment.

Kevin Gaither

CEO @ InsideSalesExpert.com Helping sales leaders avoid galactically ridiculous mistakes in all areas of building, fixing & growing their sales teams

ZipRecruiter went from 0 salespeople in 2013 to over 100 2 years later. We had a HUGE competitive advantage NOBODY would guess, but looking back, it was a KEY reason why we grew so fast.

Our secret to hiring great salespeople was less about finding the salespeople who "were experienced" and more about finding the diamonds in the rough. 💎 

✅ Sales reps with raw potential, drive, and a relentless desire to learn and succeed.

We learned to dig deeper, beyond resumes, credentials and so called "experience" to find great salespeople.

We focused on hiring for traits like Drive, Need for Achievement, Optimism and Competitiveness.

That strategy paid off in a huge way. Our “secret” was a competitive advantage that allowed us to scale quickly and gain massive marketshare from the leader.

So here’s my lesson for CEOs, Founders, and Sales Leaders: Don’t just hire for experience. Hire for potential. Your next top performer might be the one with the most to prove, not the most experience.

The results will speak for themselves.

If you found this post intriguing - you might like my course on Hiring Salespeople. Check out the link in the first comment.

The advice I'd give my 20 year old self? 
 
Work really hard but... 
 
...not so hard that you neglect family and friends time and time again. 
 
Be home for dinner with the family. 
 
You'll never remember "that one last thing you have to do" and it's never as important as a family dinner. 
 
Unfortunately, it took me about 25 years to figure that out.

How can you spot terrible sales leadership in an instant? Look for these 6 glaring red flags.

Years ago, I hired a sales manager who seemed like the perfect fit—competent, engaging, and a natural leader. But once on the job, his true colors quickly emerged.

Within a week, I witnessed him berate a rep in the most unprofessional manner. The person we hired was nothing like the one on the sales floor.

I was mortified. Not just by his behavior, but by my mistake in hiring him.

Here are 6 red flags I’ve seen over the years that signal bad sales leadership:

🚩 Inconsistent direction—saying one thing Monday, changing it by Wednesday.

🚩 Micromanaging—suffocating the team with zero trust or delegation.

🚩 Triangulation—pitting team members against each other instead of addressing issues head-on.

🚩 Zero self-awareness—completely oblivious to how their behavior affects the team.

🚩 Never admitting they’re wrong—constantly deflecting blame.

🚩 Playing the blame game—never taking personal accountability.

If you see these red flags, act fast. Your team’s success depends on it.

What are some of the other red flags you've seen that we should watch out for in a poor sales leader?

I've made a lot of mistakes in my career. If you'd like to read about them and the learning lessons that came from those mistakes, check out my book for more sales leadership screw-ups and learning lessons

There's even a free sample to download. Link in the first comment.

If you think hiring "experienced sales reps" is your key to successfully scaling your sales team, you're sorely mistaken. 
 
I thought I had it all figured out too but then I learned (the hard way) that there was a difference between Experience and Expertise. 
 
👉 Experience is repeated exposure 
 
Experience is the life equivalent of a really extensive experiment. You put yourself out there, win some, lose some, and always learn in the process. It's a place to try things out. 
 
👉 Expertise is honing your craft 
 
It's the mastery achieved by going deep into a subject, fueled by passion and persistence. Keyword is "mastery" with demonstrated results to back it up. 
 
❌ In my experience, you can have high Experience with low Expertise. 
 
💡 Can you have high Expertise with low Experience? Maybe? If the experience was really intense maybe you can? Generally no, right? 
 
This is why I feel so strongly about having a thorough hiring process for your sales leaders as well as your sales people so that you can learn more about their expertise and go beyond just learning about their experience. 
 
💡 Learning Lesson: when you’re hiring for your sales leaders or sales people, make sure that you are exploring both their experience as well as their expertise. There’s a big difference. 
 
Ever been burned hiring that salesperson or sales leader who had lots of Experience but not Expertise?

This is what a real backdoor reference check looks like between sales leaders. Two lessons to take away from this:

✅ Sales Leaders: The world is a small place. When you're making your hires, especially the ones you consider to be really important, take the time to tap your network and do a little extra research on your candidate during the interview process. You'll be glad you took a little extra time to do this.

Salespeople: The world is a small place.

😡 Don't lie about your accomplishments.
😡 Don't disrespectfully leave a company.
😡 Don't rage quit. 

You're not thinking about it at the time but your actions have consequences. You might fool a few employers but it will catch up with you eventually.

x

Real Backdoor Reference Checks

8 behaviors that give CEOs the impression you’re not a very confident sales leader. 😨 
 
I've learned early on why some of the CEOs that I worked for seemed to lack confidence in me at first but then I realized that there was a bunch of little things I was doing that didn't help my case. 
 
1) Stop Apologizing 
 
Why was I saying sorry for everything? Even stuff that wasn't my fault. Replace "sorry for replying so late" with "Thank you for your patience waiting for me." 
 
2) Infrequent Eye Contact 
 
I didn't realize how powerful this is. I'm not saying to stare like a psycho but maintaining eye contact when making a point is important to instilling confidence. 
 
3) Fast, Nervous Talking 
 
Fast talk doesn't impress. I got caught up in trying to answer quickly before thinking. Don't. Take a breath, speak deliberately and thoughtfully. 
 
4) Stop Fidgeting 
 
Is that leg bouncing uncontrollably under the table? Wringing hands? I've learned that body language speaks volumes. Pay attention to what the rest of your body is saying. 
 
5) Not Accept the Compliment 
 
I had a hard time taking compliments, downplaying my wins. A simple "Thank you" beat downplaying my wins. Far from ego; it projects confidence you've earned. 
 
6) Fear of Taking Risk 
 
I'm not talking about being a gambler. But waffling about trying new things with my team hurt my confidence. I learned to embrace evaluating and then taking risks. 
 
7) Decisiveness Over Constant Approval 
 
Leaders decide; they don't perpetually seek nods. If found myself trying to make sure everybody agreed with me before making a decision. Be confident in steering your ship. 
 
8) Not Standing Up for What's Right 
 
Confidence isn't a doormat. Assertiveness, not aggression, is key. Respectfully voice your beliefs and others will show you the respect you deserve. 
 
This didn't happen for me all at once. Gaining the confidence of the CEO is a journey for all sales leaders. 
 
If you see yourself demonstrating some of the behaviors I noted above, work to eliminate them immediately and watch the confidence the CEO has in you increase.

You might be a bad sales leader (and not know it) if you say something that sounds like this: 
 
"The salespeople should already know X..." but you haven't told them what "X" is, written it down and told the entire team. 
 
Your sales reps aren't mind readers. 🤓 
 
Tell them what you expect in as many areas that are important to you. 
 
 🔑 Reps don't know what you expect if you don't tell them. 
 
You'll be glad you spent the time setting proper expectations and regret when you didn't. 😡 
 
Trust me, I've screwed this up six ways to Sunday.

You're not a real sales leader if you brag about cutting, firing or laying people off. You're a psychopath.‬ 
 
‪No empathetic sales leader likes terminations‬ or layoffs. 
 
In fact, because it's so awful for the salespeople who get fired, nobody ever writes about how much it sucks for the sales leader who has to do the firing. 
 
Even with reps who should be let go, most empathetic sales leaders still go through this: 
 
🤢 lack of sleep the night before the firing 
 
🤢 second-guessing themselves if it's not performance-related 
 
🤢 anxiety leading up to the termination meeting 
 
🤢 sweaty palms, racing heart and shaky hands during the termination conversation 
 
🤢 grilling by HR to make sure we're taking the right course of action 
 
🤢 layoff survivor guilt especially when the sales leader lays off reps and gets to stay. 
 
I've been laid off and fired 3 times in my life and I've had to execute more termination and layoffs than I'd like to admit. 
 
It sucks. It sucks for both sides. 
 
Just nobody ever writes about the toll it takes on sales leaders when they have to do the terminations.

I've learned that being a great sales leader doesn’t mean being everyone’s best friend.

You can be a kind sales leader and still make these 8 critical (but sometimes hard to execute) moves:

👉 Say no to requests or ideas that don’t serve the team
👉 Set boundaries around your time and energy
👉 Disagree with people on your team when necessary
👉 Be brutally honest with your reps, even if it stings a little
👉 Challenge poor behavior immediately, even when it’s uncomfortable
👉 Make mistakes and own them, because perfection is a myth
👉 Stand up for your values, even when it’s hard
👉 Disagree with the CEO when you believe it’s the right thing

Early in my career, I thought being a great leader meant always being agreeable and saying yes to everything and being available to my reps at a moment's notice.

💩 But I learned that's BS.

I felt like I really started to accelerate as a sales leader when I embraced the tough conversations, the hard “no’s,” and the willingness to stand firm in my values.

If you’re not challenging, you’re not leading—you’re just managing.

Don’t be afraid to make waves from time to time and stop trying to be so darn friendly all the time.

PS: If you found this post useful - you might like one of my 10+ free sales leadership guides

The link is in the first comment

In my experience, if you want your salespeople to "feel ownership," bribing them with equity or high comp won't cut it. 
 
You hire people who have demonstrated that they have "taken ownership" at previous companies. 
 
Bribing them with equity or comp won't change how they feel. 
 
Just one man's opinion, based in experience.

Over the last 25 years, I've learned that winning sales teams don’t happen by accident—winning sales teams are built on relentless habits that most leaders know but few actually practice.

Here’s what separates the elite sales leaders from the so-so sales leaders:

✅ Never sacrifice your hiring—develop a thorough, methodical but quick hiring process.

✅ Care deeply about your salespeople—it’s the foundation of everything.

✅ Celebrate every win, no matter how small—it fuels momentum.

✅ Over-communicate—because not everyone hears you the first time.

✅ Minimize meetings—keep them short, relevant, and impactful. Or kill a few.

✅ Ask tough, thoughtful yet respectful questions—don’t shy away from the uncomfortable.

✅ Diagnose problems fast and develop several concrete solutions.

✅ Automate endlessly—cut out the low-value work for you and your salespeople.

✅ Eliminate human decision-making whenever possible—trust the process.

✅ Set sky-high standards and communicate them crystal clear.

✅ Reject toxic behavior—especially from top performers.

✅ Hold everyone accountable—yes, even yourself.

Most leaders nod their heads reading this—but how many actually follow through?

The difference between the great and the average isn’t knowing these habits—it’s executing them relentlessly.

What would you add to the list? What do you think is the most important habit?

In my experience, hiring great salespeople is the #1 habit sales leaders should learn.

If that resonates with you two, you might like my free Sales Hiring Interview Template with 77 questions you can use today to improve your probability of making a great hire.

The link is in the first comment.

I’m a huge fan of reading sales and leadership books, but many sales leaders miss the mark after closing that last page.

Follow these 5 steps and you can't go wrong:

1/ Read everything: Devour those books like your career depends on it (because it does).

2/ Take action: Implement just 5% of what you learn. Trying to do everything is a surefire way to accomplish nothing.

3/ Embrace mistakes: Mistakes are inevitable. Learn from them and don’t let them hold you back.

4/ Optimize: Don’t just accept your mistakes. Tweak your approach, fine-tune your strategy, and get better every time.

5/ Repeat: This process is never over. Once you’ve optimized, jump back to step 1 and keep evolving.

If you’re not reading, implementing, and learning, you’re wasting your time—and everyone else’s.

PS: Check out my book for more of my own sales leadership screw-ups and learning lessons

There's even a free sample to download. The link is in the first comment.

I'm sorry but this is the dumbest interview question you're asking and I know many sales leaders love to ask it. 💩 
 
"Do you hate to lose or do you love to win?" 
 
This is a dumb interview question for two reasons: 
 
1️⃣ People are really bad at assessing their abilities. There's a poor relationship between their self-assessment and their actual performance. 
 
(Ask me in the comments if you want to see the boatloads of research I found on Google for this) 
 
2️⃣ This question forces the candidate to think about what answer the interviewer wants to hear rather than the truthful answer. 
 
One of my non-negotiable characteristics that I think all salespeople should have is Competitiveness. 
 
But if you're trying to assess a candidate's Competitiveness, replace questions like the dumb one above with behavioral interview questions so we can judge the candidate by their actions and behaviors and not their words. 
 
Here are two of my favorite interview questions: 
 
• Tell me about the last time you were competitive (then tell me about the most recent time before that. You want recency and details in their answers). 
 
•Tell me about the most competitive situation at work. (Tells about a competition with co-workers or with competitors over a customer. Describes it as a common occurrence.) 
 
✅ Past performance guarantees future results. 
 
The main advantage of asking behavioral interview questions is that they can accurately indicate a salesperson's future behavior. 
 
Finding out what their thoughts and actions were in actual previous situations helps you to understand their reasoning and learn what motivates them way better than having them self-assess.

My 1st sales manager told me a dead simple secret about closing new business that has stuck with me for nearly 30 years. 
 
• the most qualified customers "fall into the close" because buying is merely the natural next step when you have a qualified buyer. 
 
If you're just stuffing Opps into your pipeline because you want your sales manager off your back or you have happy ears, you'll have to spend time twisting arms, snapping necks and discounting to have any chance of closing the partially qualified Opps in your pipeline.

Agree or disagree: sometimes, salespeople are better at selling themselves in the interview than they are at actually selling?

Think you’re great at hiring salespeople? Most sales leaders do but many aren’t as good as they think. Why?

They fail in these 4 key areas:

1/ They don’t invest in training on how to interview properly.

2/ They skip creating a structured interview process.

3/ They trust their gut over data, relying on “I know it when I see it.”

4/ They rarely track their hiring success rates objectively.

Early in my sales leadership career, I made these mistakes to. I thought my instincts were enough. But using your "gut feeling" isn’t a strategy—it’s a shortcut that led me to costly mis-hires.

Once I started getting serious about my hiring process, self-education, and tracking, everything changed.

🎉 My hiring success rate increased to nearly 80% and team results became more predictable.

✅ The best sales leaders leaders don’t leave their hiring process up to chance. They turn it into a science.

PS If you found this post useful - you might like my course on Hiring Salespeople.

The link is in the first comment.

I'll share my proven methodologies and strategies to find and hire your next superstar AEs.

I can’t stand hearing these 7 phrases from sales leaders—or worse, CEOs and Founders. 🚩

If you catch yourself saying any of these, you’re signaling a closed mindset:

1. "We've always done it this way."
2. "You don't understand. That won’t work here."
3. "I already know that."
4. "There’s no point in trying; it won’t change anything."
5. "That’s not my job."
6. "I don’t need feedback; I know what I’m doing."
7. "Why bother? It’s good enough as it is."

These phrases are like concrete walls blocking blocking any sort of creativity and innovation.

I’ve seen sales teams stall because their sales leaders were stuck in this thinking. It’s not just frustrating and destructive.

If you’re leading a sales team, challenge these thoughts. Your success, and theirs, depends on it.

PS: If you found this post helpful - here's something else that can help you.

Figure out if your new Head of Sales is going to work out or not with my free guide:

https://lnkd.in/gtUG5-Qa

Do your salespeople fight among themselves to get the "Contact Us" leads. Arguing. Whining about who got what... 
 
This is what I found. 
 
💩 "Contact us" leads are mostly garbage. 
 
I was tired of my sales reps clamoring over these leads and wasting time and I had a hunch about the quality of these so-called "leads." 
 
I crunched the data and found that "Contact Us" Leads had: 
 
👎 much lower conversion rates 
 
👎 much lower ACVs 
 
👎 much higher collections issues! 
 
💡 Learning Lesson: Don't assume that all your "contact us" leads are good enough to distribute to your sales team. Implement lead scoring and lead grading and only distribute the "Contact Us" leads that meet your fit score. 
 
What are some of your best practices with the coveted "Contact Us" leads?

I helped one of my salespeople buy a brand new Lexus but many people told me it wasn't my job to help him buy it. 
 
Oh, I certainly didn't GIVE them the money. He had to earn it. 
 
👉 I helped him by coaching him how to get into the position of being able to buy the car. 
 
I learned in one of our initial coaching sessions that he really wanted to buy a brand, new Lexus in the next 6 months. 
 
So we broke down what he needed for the downpayment into what his specific, weekly activity goals should be to have him save enough money after taxes to hit his goal. 
 
🎉 Talk about one motivated rep. And 5 months later, he bought his Lexus. 
 
Learning Lesson: As a sales leader, 
 
✅ find out what your rep's goals are OUTSIDE of work and 
 
✅ when you can connect a salesperson's sales goals to a personal goal outside of work, you have an amazing recipe for motivation. 
 
Ever done something like this for one of your salespeople before? 
 
Tied what they want in their personal life to what they do in their work life?

Taplio

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