20 Sales Career Tips From Top Sales Leaders

Over the course of your sales career, you will experience a lot. You will experience triumphs and successes, and you will also encounter obstacles, defeat, and failure.

I mean let’s face it, we face more rejection than most do in any other career or industry.

To truly make it in the sales field, you need grit, positivity, a strong work ethic, a good support system, strong leadership, urgency and patience, emotional intelligence, resiliency, communication skills, curiosity, continuous learning, and the ability to build and sustain long-lasting partnerships. So many intangibles play into the sales role, that as sales professionals, we must be constantly improving and honing our craft. And this takes years, if not a lifetime, to accomplish.

I think we often forget that all great sales leaders and business owners started off somewhere, just like you and I.

To help you master your sales career, we asked top sales leaders to share some of the best advice that they wish they had received when they first started to build their sales careers.

  • What advice do you wish you received when you first started your sales career?
  • What do you know now that you wish you knew then?
  • What sales career tips and advice do you offer to all new sales reps?

Here is the best sales career tips that sales leaders wish they received before starting their careers:

1. Ed Calnan Know how to think critically

Founder & President at Seismic

One piece of advice I wish received when I was just starting out has to do with what it really takes to be a great salesperson. The common assumption is that all someone has to do is hit the phones hard and fast, and through brute force you will automatically become successful. Nothing could be farther from the truth, because it de-emphasizes the role intelligence plays in sales.

What I’ve learned since, and what we teach all sales reps at Seismic, is that success comes through preparation, research, and most importantly, critical thinking. If you can’t adapt to an unexpected question, or show each prospect that you know more about them and their company’s goals than they could have ever thought was possible, then it simply doesn’t matter how many calls you make; you will continue to hold yourself back from success.


2. Melissa Raffoni – Start by caring

CEO & Founder at Katahdin Group

Early in my career one of my clients told my boss, “Melissa Raffoni is a personal friend.” I was in my twenties and the client was a CIO of a major company. Five years later, another client told me, “I do business with you and your company because you are authentic, you cut to the chase, and we have a relationship where I want to help you and you want to help me.”

My advice to those who are new at selling is as follows:

1. Be authentic, be yourself.

2. Be prepared, not only in researching the company (which is old advice) but in your agenda. Understand how you plan to use your time and your client’s time.

3. Be part of the solution. Solution selling is a phrase, yes- but everyone should solution sell. All that means is to ask questions first, listen, and work with the prospect to propose ways that you can help them.

Listening is hard, of course, but the ability to quickly jump to solution alternatives that meet their needs to begin planting seeds right there and then while you have their attention is definitely a skill. If you really care about helping the client- first and foremost, you will listen more attentively. Start by caring.


3. David Brock It’s not about your goals, it’s about your customer’s goals

Author of Sales Manager Survival Guide & CEO at Partners In EXCELLENCE

As important as it is to know your products/services, it’s more important to know your customers, their business, their goals, and how you help them achieve their goals. Stated differently, if the customer and what they want to achieve isn’t the focus of everything you do, then you won’t achieve the success you could reach.

Curiosity is one of the most critical attributes for a salesperson. If you aren’t curious, you won’t make it. Curiosity drives you to learn about the customer, to learn about their business, to learn about them as individuals, and to have them learn about your products and your company. Curiosity enables you to figure out how you can be successful with your customers.

You have to be obsessive in continuous learning and relentless in execution. Sometimes, you have to sell harder within your own company than you have to sell to the customer.


4. Jennifer Hunt – Don’t take rejection personally

Cofounder at SFE Partners

The first thing I would say is congratulations on your career choice! There is no better feeling in the world than the rush of closing a sale and controlling your destiny. That said, it’s not as easy as it looks so get ready for the ride of your life…

  • Be confident in your talent. No opportunity is out-of-reach. Be assertive without being aggressive or arrogant
  • Don’t take rejection personally. Have a sense of humor and prepare for rejection. Savor the wins and put the losses behind you. There will be days that are fantastic and days that are truly difficult. Believe in yourself and realize that tomorrow will be better.
  • Be patient. Success isn’t overnight. Keep at it. There is no replacement for hard work and focus. Remember, timing is everything.
  • Nurture your relationships. Network for success. People will try to test your integrity and ethics; don’t waver. Don’t burn bridges.
  • Know your product/service. Customers recognize quickly when you don’t have all the facts and losing credibility is not something you can recover from easily. Walk the walk, talk the talk.
  • Be prepared and ask questions. Listening is key. Remember that every personality and every need is different so be ready to adapt to any situation. A script is only a tool or guideline – define your message and make it your own.
  • Don’t be afraid to walk away. Sometimes deals don’t make good business sense and closing a deal at any cost can actually hurt your reputation as a salesperson.


5. Daniel Disney – Never stop learning

Founder at The Daily Sales

The advice I wish I had at the start of my sales career, and it’s the tip I give to every single salesperson I meet now, is to immerse yourself in learning. Start by finding the top salespeople in your company and industry and learn what they do. Then read sales books, read sales blogs, listen to podcasts, watch videos, and go to sales events. The list is endless. Learn, apply, practice and perfect…repeat.


6. Laurie Page – It’s not all about the features and benefits

Managing Partner at The Bridge Group, Inc.

When I think back to my early days in sales, it amazes me how much things have changed since the early ‘90s!

The advice I think may have helped me most back then would be to “think more out-of-the-box”. It’s a common theme now, but back in the early ‘90s sales teams were all about “me” and “my products.” It was an endless re-run of “features and benefits.”

Today, no one wants to be sold to that way. They are looking for an intelligent partner with a personality that’s able and willing to really connect and help solve their problems. It’s all about our buyers. You certainly need to be confident, but that confidence has to be backed by knowledge and an ability to make your solution personally relevant.

Storytelling is one of the most powerful ways to accomplish this. Become a rich source of real-life anecdotes that demonstrate how your solution can become a valuable tool for that specific customers set of needs. The ability to draw upon experience and selectively present relevant stories is an invaluable skill that will allow you to establish a real connection with your prospects.


7. Dan Fantasia – Believe in yourself and don’t let doubt win

President at Treeline, Inc.

The first piece of advice I would offer is that in life you will always have to believe in yourself. There are times when taking on new challenges personally and professionally that you will experience doubt and uncertainty because of the unknown. That is to be expected, but the one thing that can never waver is your belief in yourself. I share this same philosophy with my wife, my kids, and my coworkers.

In regards to your career, I recommend that you find a good company to work for based on values and clear vision, and then expect to work hard…harder than you have ever worked before. When things get tough, forge through it. If you want to be successful, go after it with more determination than anyone else. Show that you want it more than your competition. Focus on what needs to get done, do it, and you will be a top performer.


8. Richard Harris – Surround yourself with people smarter than you

Owner at The Harris Consulting Group

I would suggest understanding what it means to have a mentor, and then go about finding several. Some that will help with life, work, hobbies, etc. I always knew to surround myself with smart people. I wish someone would have taught more about executing on that concept.

In my role as a sales consultant, I am constantly giving out advice. People know they can email, call, tweet, or LinkedIn message me about anything. It can be about their job, a particular deal, a difficult boss, and I will work to find time to speak with them.

9. Ashley Becker – Work hard and be patient

Sr. Director of Global Member Services & Sales at AA-ISP

Some advice I would give a new rep that I wish I knew early on is be professionally persistent, confident, and don’t give up! You will find your groove and just need to be patient. Use social media to your benefit as there is so much you can find out about your prospects and customers that you can use to make a conversation more valuable. This is something I really did not get taught at all when I started that could have helped tremendously with initial outreach.

The final thing would be that Inside Sales is an amazing and growing profession. You can go far in this career and make leaps and bounds, not only with compensation but moving up in a company. You can control your career path, and your personal and professional successes.


10. Mark Birch – Find a mentor

Founder at Enterprise Sales Forum

When I started in sales, it was an accident and there were no other sales reps I could talk to because they had all left the company I was at. I fumbled around like an idiot making tons of rookie mistakes. If only I had a mentor, I could have asked all the dumb questions and received guidance on how to do sales before I made myself look like a fool.

Today it is a bit different because there are so many resources available, but it is still valuable to talk to an actual person who can understand your situation and provide specific advice. If you are starting in sales now, find a successful senior rep at your company or go to a local Enterprise Sales Forum event to network with peers, then ask them if they would be willing to answer some fundamental sales questions. Chances are they will be honored to be asked and will eagerly help a new sales rep.


11. Emmanuelle Skala – Relentlessly qualify

VP of Customer Success at Toast, Inc.

Early in your sales career, it’s easy to spend time with anyone and everyone who’s willing to spend time with you. Being busy doesn’t mean you are being productive. Turn the tables around and ask yourself “Is this person worth MY time?” You only have a limited number of selling hours per week (a lot less than you think) and REAL deals take a lot of time to close. Don’t spend precious hours with unqualified deals or unqualified people. You are the CEO of your territory and not everyone should get time with the CEO.


12. Christopher Simone – Block out the distractions

Chief Sales Officer at C-4 Analytics

There will always be distractions and excuses within reach, but none of that creates success. Just like in test taking, you have to find a way to block out the distractions and stay focused. There will be challenges, real (not imagined) challenges with the product or company (because none are perfect) and there will be plenty of lesser salespeople who will lose focus as a result. The mission for a salesperson is to avoid the immediately available excuses and find success no matter what.

And the opportunity to switch jobs is seldom the answer to this particular challenge because “the grass is always greener.” It is important for a new salesperson to break through the distractions, excuses, and challenges and find success. In doing so, prove that success is a matter of choice. That is a foundation on which to build. In fact, that determination and seriousness of purpose as a salesperson is actually, in and of itself, a primary measure of success.


13. Meridith Elliott Powell – It’s not about price

Business Growth Expert & Keynote Speaker at MotionFirst

I wish someone had taught me early on that sales had very little (almost nothing) to do with price. When I got into selling, every mentor I had sold on price, and did very little “real selling.” It took me years to learn how to, and build the skill to, sell risk and value, and how to stop selling price.

14. Donald C. Kelly – Not everyone is your customer

President at The Sales Evangelist

The advice I wish I received before starting a sales career would have been to focus on an ideal customer and know how to become a problem finder. Too often new sellers try to get everyone. They come out of the gate fast and determined to make money, but not everyone is their customer.

Like most, when I first started out, I was focusing more on ME and making sales as opposed to finding out the problems and challenges my customers were facing. Sellers who can do this will be seen as more valuable by their customers and will be able to naturally guide their buyers to a successful solution. I share this advice with new reps I coach in my group coaching program, TSE Hustler’s League.

15. Steve Przypek – Always take a nothing ventured, nothing gained approach

Executive VP of Sales at Zoom Media Connect

When I first began my sales career, I wish someone shared with me the importance of staying engaged with your positive and supportive team members. Learn from best practices and make them your own by communicating and sharing ideas with the best of the best within the organization.

It’s also important to have confidence but not “false confidence.” Don’t procrastinate thinking that you can coast, and then pull out your goal at the end. Tackle your sales goals, then reward yourself.

Always take a nothing ventured, nothing gained approach. Increase your sales and income by asking for the lead, the referral or the sale, or taking a shot at it. The worst that can happen is that you’re right where you were before you ventured. The best that can happen is more sales and more opportunities.


16. Jamie McHugh Listen more and talk less

VP, Business Development at CBI, a UBM Americas Company

Sales isn’t rocket science, but it also isn’t for the weak-hearted or unintuitive. Often times, we let our own egos and perceived end goal (closing the sale) get in the way.

Building trust, instilling confidence, and creating meaningful rapport with your customers is key to building long-term relationships. Listen more and talk less. Truly hear what your prospect is telling you, not only through their verbal communication, but also through their intonation, body language, and what they aren’t saying.

Don’t be afraid to admit you don’t know the answer or to ask for help, and don’t assume that you know what your customer wants. Let your personality shine through and create personal connections by building trust and adding value.


17. Phill Keene – Hire your own boss

Director of Sales at Costello

Early in your career, find someone who can help you grow. You also need to find out your style of work. This is even more critical in sales because who you are is shown on a daily basis in the ways that you deal with customers, the struggles in the sales process, and with peers.

My advice to salespeople early in their careers is to “hire their own boss.” You need someone to show you the ropes and make you better; someone who will actually teach you how to navigate the sales process, and perform the very basics with perfection. Don’t worry about the shiny objects out there because entering sales with a strong foundation will get you all of the things you dream of in the long run.


18. Sue Boardman – Be passionate about the company and solutions you represent

VP of Sales at MassPay

I have been in outside sales and sales management for over 30 years, and here is some advice I follow now that I wish I knew when I first started. There is nothing more important than consistent activity! Every week you need to see enough people to generate the sales needed to hit your goals.

Passion sells! Be sure to represent a company that you are proud of and confident that their products/services truly help the buyer. For the past 27 years, I have felt more like a consultant than a salesperson.

Read! Read everything you can on your industry. Become an expert in your field. Be relevant, current, and knowledgeable about your products/services to bring value to the buyer.


19. James McIlroy – Make it personal

Lecturer at University of New Hampshire

Beginning in sales, I was entirely business focused in all of my conversations. Hitting all the right value points, asking questions, listening to understand their business problem and explaining how we could help but … I was missing an important opportunity.

When my wife and I were having our first child, my VP asked if I let clients and prospects know in my sales conversations. I hadn’t. It proved to be a great relatable moment and deepened my relationships. Clients started to ‘make it personal’ from sharing parenting advice to sending me their Alaskan vacation pictures. I never turned back.

Making it personal definitely opened opportunities that would not have been there. Work becomes more fun and enjoyable if you make personal connections with people as you go. I share this story with new students to help remind them that they are talking to real people.


20. Graham Hawkins – Leaders are readers

Founder & CEO at SalesTribe

My biggest piece of sales career advice is to continuously learn. I wish that someone had told me that a law of diminishing returns exists when you focus solely on sales execution. That is, we sales folks get so caught up in the day-to-day pressures of sales performance (and that now outdated legacy of quota attainment) that we rarely get any time to stop and think about our own self-development or ongoing learning.

As Abraham Lincoln famously stated: “If you give me 6 hours to cut down a tree, I’m going to spend the first 4 hours sharpening the axe.” Salespeople rarely (especially these days) put aside any time to stop and sharpen the axe and that’s a HUGE mistake. I learned this lesson much later in my career, and have become a prolific reader ever since.

Leaders are readers, and they are acutely aware that continuous learning and intellectual curiosity are the keys to being valued by customers. To survive in this new customer-led era you must become a specialist, meaning that you have to keep bringing your customers unique commercial insights and that requires a relentless approach to self-development and learning.

What other tips and advice do you wish you learned when you first started your sales career?

Published On: August 22nd, 2017Categories: Blog News, Job Search and Career, Sales Success

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