16 top sales leaders and entrepreneurs share their best sales advice and tips
We've interviewed 50+ top sales leaders to get their best sales advice, tips, and strategies that have transformed the way we sell today.
From accomplished entrepreneurs who've grown sales organizations that have generated billions of dollars throughout their careers, to executives that have built the sales engines powering companies like LinkedIn, Google, and Box, to the bestselling authors who've literally written the books on how we think about selling today—we're bringing the heat this week.
Now, let's dive into the best sales advice from the world's top authorities in sales.
1. View failures as learning opportunities
— Jill Konrath, bestselling author, speaker, sales consultant
For Konrath, who’s built a long-lasting career for herself as a speaker, author, sales consultant and trainer with Fortune 500 brands, her best piece of sales advice isn’t around learning a specific tactic, technique or sales strategy. Her advice isn’t to pick up a specific book, enroll in a training program, or make one hundred cold calls a day until you’re suddenly an expert, either.
“My best investment in becoming a better salesperson wasn’t in a course or a book—the best investment I ever made was changing my mindset,” shares Konrath.
During her first year selling copiers at Xerox, Konrath had a life-changing moment. After booking a sales meeting with an executive assistant, and then trying to go around the assistant—directly to the CEO based on advice from a sales book she had read, Konrath experienced a very painful failure.
Once she arrived for her meeting, expecting to see the CEO, Konrath was greeted by the executive assistant who felt disrespected by her attempt to sidestep the assistant’s authority. After being yelled at for a few minutes, Konrath fainted right there in the lobby of her prospect’s office.
It was time for some soul-searching once she recovered. “I made a decision at that point that I had not failed. I just had a valuable learning experience,” Konrath explains. “Over my career, I’ve had a lot of valuable learning experiences, and not one failure. I’m on a figuring it out journey, and that one choice has made all the difference in my career.”
2. Invest in your own education
— Grant Cardone, bestselling author, speaker, sales trainer
“The best investment I ever made was when I was twenty-five years old and I hated sales. I borrowed $3,000 from my mother to buy a sales program—it was twelve cassette tapes and it took ten days for it to arrive,” Cardone shares.
Did you get that? The man who’s built a massive business for himself around sales education, once hated sales. His success in the world of sales hinged on making the difficult decision to stick with it and invest heavily in further educating himself—rather than giving up and changing careers.
Cardone continues, “I made so much money from those tapes. I went from making $30,000 to making $100,000 a year. Most importantly, not only did I make more money, but for the first time in my life I could say I loved sales. For the first time, I knew what I was doing.”
“Ever since then, I’ve spent hundreds of thousands of dollars investing in myself and my people, in hopes of making us all better, more motivated, more strategic. Some of the programs don’t work, but I keep investing, knowing that it’ll pay off in the long run.”
3. Hire a sales coach
— Trish Bertuzzi, bestselling author, sales consultant, speaker
Bertuzzi has been in sales for nearly three decades, having helped more than 320 world-renowned brands build world-class inside sales teams through her consulting company, The Bridge Group.
She’s also the author of the #1 Amazon bestseller, The Sales Development Playbook, and when it comes to sharing her best sales advice, here’s what Bertuzzi has to say.
“I am over the moon excited to be working with a sales coach. I’ve had one session so far, and holy crap. The reason I think coaching works so well for me, is because I record all of my sales calls and coaching helps me realize things I’ve never even thought about.”
Believe it or not, this has been one of the most common recurring themes with just about every speaker we've interviewed for the Inside Sales Summit—be it sales leaders, wildly successful entrepreneurs, keynote speakers, bestselling authors—they all see the value in having a coach or a mentor who can help bring a fresh perspective to their selling style.
Here’s an example that Bertuzzi elaborates on, “When I’m talking to someone and they’re telling me what the current state is, I don’t compliment them enough on what they’re doing right—it’s a waste of an opportunity to share empathy and develop a relationship with them.”
Even those at the top of their game (who’ve literally written the books on selling) can still make improvements and become more effective through critical feedback and the sales advice of others who come with their own unique experiences.
4. Have a plan for every sales call
— Neil Rackham, bestselling author, sales consultant, academic
Rackham, the bestselling author of the book SPIN Selling, which pioneered consultative selling as we know it today, says the best sales advice he could possibly share, is to be adequately prepared before every single sales call or meeting with a prospect.
“Before I go out on an important sales call, with all the tools that are available, I still just carry around a little notepad and pencil. I’ll write down 3 or 4 good questions I want to ask, make a little plan, and then tear it up so that I’m not pulling it out in front of my prospect,” he shares.
For Rackham, the act of physically writing down his questions and knowing the rough game plan for how he wants the meeting to go, commits it to memory and he’ll come off as much more on top of his game.
5. Check your ego at the door and learn
— Aaron Ross, bestselling author, sales consultant, speaker
When it comes to building, scaling and training a sales team, Aaron Ross sits near the top of every list of authorities on the subject. As the author of the bestselling book Predictable Revenue, Ross is well-known for leading Salesforce into the lucrative enterprise market. When asked about his best sales advice, here’s what he has to share.
“Going from being CEO of an internet company to checking my ego at the door and saying that I just want to learn—I’m going to take a job at Salesforce and the only one they had was answering the 1-800 line, paid shit money, very little equity,” Ross explains.
After shutting down and liquidating his own startup in the dot-com bust, instead of just looking for a job that’d pay him the most, Ross made a conscious decision to remain humble and take a gig where he could build the skills he wanted to perfect.
Ross continues, “I was focused on wanting to learn, and because of that, I treated the job as if I was getting paid to learn. It wasn’t about ego; sure I was frustrated at times, but taking a job purely for the learning experience was the best investment I ever made.”
6. Put in the extra time to be well-prepared for every sales call
— Sujan Patel, SaaS founder, growth marketer
As the owner of multiple marketing agencies, Sujan has years of experience prospecting and closing complicated, high-ticket deals. He's also the co-founder of multiple SaaS businesses, including Mailshake, which helps salespeople, marketers, and entrepreneurs send personalized cold outreach emails en masse.
"For a lot of salespeople, the longer they're in the game, the more comfortable they get talking with leads and feeling out calls or meetings as they go. This kind of experience is invaluable, of course, but it can sometimes lead to complacency and placing less importance on being over-prepared."
"Especially for complicated, long-term deals, knowing the person and company you're talking to inside and out not only lets you tailor your conversations to their needs and anticipate common sales objections, it also shows your prospect that you really know what you're talking about."
"Going the extra mile in your early conversations show that you'll put in the extra work when they're a client or a customer, and can be the difference between a no and a yes down the line."
7. Embrace the challenges that come your way
A serial entrepreneur with a relentless drive, Romanow had to learn how to sell at a young age when she launched her first business during college. Gaining traction and learning how to sell with her first side projects set Romanow down a path to eventually selling one of her startups to Groupon.
When asked to share her absolute best sales advice, Romanow says it was making the decision to work a tough sales job—because it taught her not to fear rejection.
“The best investment I’ve ever made in becoming a better salesperson, was taking a part-time job selling water heaters door-to-door. There was nothing scarier than going door-to-door, convincing people I wasn’t crazy, and actually getting inside of their house to complete the sale,” Romanow explains.
Instead of shying away from a job that was clearly proving to be difficult, Romanow took this experience and turned it into a challenge for herself—one that she knew would help to sharpen a skill set that’d be useful for the rest of her life. It’s safe to say that sure paid off.
“To this day, nothing has taught me more than that job. As an entrepreneur, you should never underestimate how much of your success is based on your ability to sell. You sell to get vendors, customers, employees, investors, partnerships. I’d tell anyone that’s young to take a hard sales job, because you’ll learn so much and become so unafraid.”
8. Focus on being consistent, disciplined, and ditch the “hacks”
— Steli Efti, CEO at Close, author and speaker
Throughout my career as an entrepreneur, I often found myself having to be my #1 salesperson, especially in the early days of getting a new business off the ground.
I experienced ups, downs, and through it all, the best sales advice he has to share is to learn early on in your career that the charisma, science-backed negotiation tips and clever sales hacks in the world won’t save you in the long run. If you want to be the best salesperson you know, it’s going to take consistency and discipline.
The best investment I’ve ever made in becoming a better salesperson, is choosing to focus on consistency over charisma or any other hack. I’ve spent my entire life studying sales, communication, psychology. Every bit of it was worth it, but what really made the biggest difference was learning how to be consistent and have discipline in sales.
That’s coming from someone who’s invested hundreds, if not thousands of hours into his own education through sales books, training opportunities, mentors, interviewing experts and more.
Learning how to perform every single day forever, no matter how I feel was a major breakthrough. That’s what was holding me back and slowing me down during the first part of my career—being very inconsistent with moment so brilliance and moments of total disaster. Relying only on my charisma, and not on my character to sell. My biggest shift was realizing that consistency is king, and character is how you win the long game.
9. Don’t sell what you don’t believe in
This piece of sales advice coming from serial entrepreneur, Noah Kagan, cuts to the core of a very deep, often difficult to acknowledge problem that many salespeople have—it’s easy to find yourself caught in a job selling something you don’t personally care about (or believe in).
Time and time again throughout the 50+ interviews I’ve done with the world’s top sales leaders for our Inside Sales Summit, guests have consistently shared that the best salespeople they’ve ever met, are the ones who clearly believe in and care deeply about the product or service they’re selling.
Kagan explains, “Go find a product that you just believe in. Go out and sell it—practice selling it even if that company doesn’t hire you—just sell it for them. Because if you’re trying to get a job and you came to us and said, hey I’ve signed up four customers for you, I’m ready to take it full-time and now you can start paying me, I’m going to take your call.”
It’s obvious when you’re being sold a bill of goods that the salesperson isn’t personally invested in. Remember, if the genuine excitement isn’t there, you won’t make the sale.
10. Put in the work and get your 10,000 hours
— Juliana Crispo, CEO at Provide, sales educator
When asked to share her best sales advice, Juliana Crispo, the former sales exec that now runs an education-focused network helping high-performing salespeople accelerate their careers, shares something that on the surface may sound plain to see, yet is so often overlooked—experience is your greatest teacher.
“The best investment I’ve ever made is in learning the hard part and taking the time to fail.”
Even the most experienced salespeople have failures, and becoming an expert at selling isn’t about avoiding failure altogether—but rather, choosing to embrace that rejection will be a natural part of your journey and that it can’t ruin your day.
Sure, you should be able to predictably close more deals as you build your skills and get more experience over time, but how you choose to deal with your setbacks will dictate whether or not you’ll stay in the game long enough to achieve mastery.
Crispo elaborates, “it takes 10,000 hours to become an expert at something—and those 10,000 hours of cold calling, prospecting, rejection is brutal, but it’s that investment of time that’s necessary in order to truly understand sales. It’s the only way to become an expert at selling.”
11. Experiment and don’t make the same mistake twice
— Jamie Shanks, CEO at Sales for Life, author, speaker, consultant
In the inevitable moments of failure, rejection, doubt that come along with a career in sales or entrepreneurship, having confidence in yourself and your ability to keep pushing forward with experimentation is mandatory in order to succeed.
Jamie Shanks, a seasoned veteran in the world of inside sales, has this to share when asked about his best sales advice. “The best investment I’ve ever made is in building my own confidence. What I’ve realized is that I’m willing to do things and learn, to get kicked in the teeth as long as I don’t make the same mistake twice.”
There’s no way around it in sales, you have to be willing to experience rejection. It’s going to happen (multiple times a day), no matter how skilled you are at selling. But it’s in how you react to new information and the results of your experiments that will go on to define your future.
Shanks continues, “experiment, try new things, but don’t do the same thing over and over again if it’s not working, expecting different results. Fail, pick yourself up and become a little better. Invest in your own confidence and realize that you can do this.”
It all starts with having the confidence in giving yourself permission to experiment.
12. Surround yourself with the smartest people you can
— Max Altschuler, CEO at Sales Hacker, author, speaker
Entrepreneur, speaker and bestselling author of the book Hacking Sales, Max Altschuler, has worked in and consulted with dozens of high-performing sales organizations over the years. He’s learned first-hand that experience is king when it comes to becoming a better salesperson, but he’s also picked up a clever hack that helped him accelerate his own sales knowledge (and experience) earlier in his career.
When asked to share his best sales advice, here’s what Altschuler has to say.
“Nothing beats experience, but surrounding yourself with people who are better than you is one of the best investments you can ever make when it comes to building your selling skills,” Altschuler says.
This should come as no surprise. One of the most consistently shared pieces of business advice I’ve gotten from world-renowned entrepreneurs like Tim Ferriss, Richard Branson and Arianna Huffington always tends to come back to surrounding yourself with people you can learn from—people who will push you to become better at your craft.
The mentorship factor is equally as important for a career in sales. Altschuler adds, “if you’re in sales, go track down the smartest person you can find in the area you want to build your expertise in—and disregard how much more money you can make elsewhere. In the long run, you’ll make a lot more money, learn a lot more, and be more fulfilled by going out and working for the smartest person you can find.”
13. Learn from those who’ve gone before you
— Dorie Clark, marketing consultant, bestselling author, speaker
Dorie Clark, the bestselling author, speaker and sought-after marketing consultant to companies like Google, Microsoft and The World Bank, has learned a lot about what it takes to close high-value contracts with enterprise organizations.
In her latest book, Entrepreneurial You, Clark breaks down her best lessons learned from building a consulting practice and diversifying her income streams.
When it comes to sharing her best piece of sales advice, Clark is a huge proponent of cutting down on her own learning curve and taking the most impactful lessons from those who’ve already achieved exactly what she wants to accomplish.
Clark explains, “when it comes to building my selling skills, I’d actually make a book recommendation. A book that’s been really helpful to me is called Million Dollar Consulting by Alan Weiss and he did a great job in terms of how to structure proposals, how to have good conversations with buyers, and he has a great deal of expertise to share.
For Clark, whose goal was to build her own million-dollar consulting business when she first got started, the lessons and advice she picked up from this book were directly applicable to accelerating her career. Start with our picks for the best sales books of all-time and find the experts you can learn the most from.
14. Listen to your sales call recordings
— Neil Patel, co-founder at Crazy Egg, Kissmetrics, Quicksprout
Whether you’re selling your own product or managing a team of reps, this piece of sales advice from Neil Patel, three-time SaaS co-founder of Quicksprout, Kissmetrics and Crazy Egg, is applicable to anyone who wants to improve their selling abilities.
“The best thing I’ve ever done when it comes to building my selling skills [and that of my team] is listening to recorded calls. Listen to your sales calls and do roleplay. More importantly, don’t do this just once a week or once a month—we do this literally every single day with every salesperson on our team. That’s the reason our team closes so well,” Patel shares.
If you’re in B2B sales, chances are high that your sales process won’t be able to escape an element of hopping on the phone with prospects on a regular basis. From using cold calling as a strategy to garner interest in your product, to using email for booking warm discovery calls, there will always be room for improvement no matter how skilled you (or your sales team) are—and Patel is no stranger to this reality.
“It’s bullshit to say here’s a script, or you’re already good to go based on past performance, because you’re always going to get edge cases in sales. You have to not only listen to your recorded calls, but have [your reps] admit where they screwed up, get them to understand why, roleplay to help them get better, and then listen to future calls to see if they’ve fixed it. It takes time to break bad habits, so repetition is key.”
15. Be empathetic and listen to your prospect’s pain points
— Ben Sardella, CRO and co-founder at OutboundWorks, former co-founder at Datanyze
Consistently ranked as one of the world’s most influential salespeople, Ben Sardella started out as the first sales rep at NetSuite back in the day. After making his way into various sales leadership roles and co-founding the technographics company, Datanyze, Sardella is now onto his next adventure at OutboundWorks where he’s helping B2B companies automate their sales development process.
As a constant advocate of testing, experimenting, and iterating with new sales tools that hit the market, when Sardella’s asked to share his best sales advice, he cuts straight to the core of why people buy.
“I love new tools, because they’re exciting. But as we get into the future of sales, we need to take a huge step back and focus on the skills that are not technology-related at all,” Sardella explains.
When you think about it, this makes perfect sense. With tools doing increasingly more of the average salesperson’s day-to-day responsibilities, the opportunity becomes much larger for skilled practitioners to come in and really show how effective personalization is during the sales process.
Sardella elaborates, “the technology is going to start handling the majority of our tasks, and what’s really going to be meaningful is being empathetic. How able and willing are you to actually listen to your prospect’s pain points? How responsive are you going to be? What are you going to say and commit to? What research will you do to truly understand their business so you can get personalized when you engage your prospects?”
16. Commit to your greater vision
We’ve all been the recipient of a transactional sale at some point. When you can feel that you’re being sold not because the product or service will have a clear, meaningful impact on your life, but purely for the sake of lining the pockets of the person doing the selling.
That’s runs counter to the consultative sale, the belief that you’re a trusted advisor to your prospects—guiding them to the right solution for their specific needs, regardless of whether or not that actually ends up being your solution.
Entrepreneur, photographer and director Chase Jarvis can sniff out the transactional salesperson from a mile away. When asked to share his best sales advice, here’s what Jarvis has to say.
“Be committed to the big vision. If you’re transactional in your selling, people can feel it and smell it. What’s your why? As soon as I found my why, all of the selling faded away and the authenticity came out. If you’re committed to something for the next two weeks, the next paycheck, be careful because that narrative is a trap—pretty soon that eroding mentality of constantly chasing the next thing will hurt you,” Jarvis explains.
“Alignment and playing a game that I actually care about has made all the difference in the world. It also provides a level of hunger that can’t be achieved when you’re just working towards a check.”
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