Sales Lessons That 10 Sales and Marketing Experts Learned the Hard Way

After working with hundreds of sales and marketing professionals at QuotaFactory, we’ve had the opportunity to work with and learn from some of the best. From preparation to dealing with slip-ups, we've compiled some of the best B2B sales and marketing lessons that nine experts have learned during their careers.

10 Sales Lessons from Sales and Marketing Thought Leaders

1) Facts tell, stories sell

"During a conference I was presenting at in Eastern Europe, I was given the opportunity to do an on-air interview for a popular TV station in Bucharest. I had no idea what I was going to be asked about other than something to do with marketing.

Did the TV reporter ask about me or my agency? Did he ask me about the conference or my presentation? No, of course not. He asked me for quick stories about innovative advertising and marketing -- five of them. All to be told in five minutes. I learned this right before the cameras rolled.

There was no backing out, and ultimately, I was able to come up with two random stories that made it to the live interview. My storytelling was not weak, but not strong either.

The experience reinforced this lesson: Whether you are an individiual contributor in Sales or Marketing or you hold a leadership position, you must have a healthy number of stories on tap for whatever expertise you want to be known for. This applies to networking, meetings with prospects, media interviews, on social media and in your writing. To put it simply: Facts tell, stories sell." 

-- Lee Odden, TopRank Online Marketing CEO

2) Don’t chase people who don’t need or desire your offering

"Believe it or not, my career started selling restaurant coupons door-to-door. Sounds crazy, doesn’t it? But it’s true. When I was 22, fresh out of college, I wanted to move to Massachusetts, so I did. But I had no job. Forced by the reality of paying bills, I settled for a job pushing restaurant coupons door-to-door. The job was 100% commission-based. If I had a good day, I went grocery shopping. If I had a bad day, I ate whatever was cheapest at McDonald’s. I learned many things during the four months I hustled, but what stuck with me most was what I learned about personas. I didn’t call it that in those days, but they were buyer personas, nonetheless.

After a couple of weeks on the job, I started to see patterns -- neighborhoods where I’d make a lot of money, and ones where I’d make almost nothing. It wasn’t densely populated areas with lots of stay at home moms. It wasn’t retirement communities. It wasn’t even neighborhoods that had lots of mansions. It was a busy downtown with a police station, fire station and bank. I could make more in one hour visiting those three places than I could walking the other areas for six hours. Police officers hated the idea of me walking in unfamiliar neighborhoods alone. I leveraged their concern for my safety to sell more coupons. At the fire station, there were always hungry (mostly) men, who were generally a little bored with down time between calls, happy to indulge a young woman in a flirty chat. And bankers fully appreciated a good bargain and always had several people more than willing to part with their money for a good deal.

By accident, I had discovered personas. Crude, incomplete, not well researched personas, but buying signals nonetheless. And this is something that has stuck with me throughout my entire career.

We tend to spend far too much time chasing people who don’t need or desire our offering. Instead, focus on those to whom you can make a real connection and you’ll find your productivity soar."

-- Samantha Stone, The Marketing Advisory Network Founder

3) A bad slip of the tongue

"I’ll admit it. I once said something in a sales presentation that was so profoundly obscene I have not shared the actual words with anyone, not even my wife. It was a slip of the tongue, but it was a bad slip. It was a lot more like a full-blown crash-and-burn. I remember like it was yesterday.

As the phrase was coming out of my mouth, I could almost see the words hanging there in mid-air, as if I could somehow snatch them back and swallow them all. If ever I longed for a do-over, this would have been the time. Once the words were spoken, there was a deadly pause in the room. I’m not sure who was more stunned: my prospect or me. We just stared at each other for what seemed like an eternity.

Finally, I asked, “Did…did I just…did I just say what I think I just said?”

“Yes, you most certainly did,” was the reply.

Presentation over. Have a nice day. (“Do you validate?”)

The incident I have described took place very early in my sales career -- nearly 30 years ago -- but I still remember it clearly, and I do so on purpose. I no longer dwell on the embarrassment; today it is just a funny story. I just want to remember that screwing up is inevitable, but what happens after the failure is entirely up to us. I chose to use that situation as mental leverage. I made a horrible mistake, and I lived to tell the story.

Was it fun? Heck, no. Did it make me a better salesperson? Absolutely. I have since learned that mistakes, failures, and stumbles are a necessary part of learning and growing. That which does not kill us makes us stronger, correct, Mr. Nietzsche? Looking back on my sales career, if I had a dime for every stupid thing I ever said in a sales presentation, I would be a very wealthy man. And, in fact, I am. I am rich in experiential knowledge, and that is the very best kind available."

-- Jeff Shore, Shore Consulting President

4) Not all clients are the right fit

"It took me too long to realize that not all clients are created equal, and I should not treat them equally. My lesson was that there’s no law stating you must sell to everyone, or keep servicing clients that are the wrong fit for your business.

If you’re miserable working with a client that you know isn’t profitable for your company, you won’t be motivated to serve them well. And, if that client isn’t receiving the best treatment, they won’t hit their desired goals. By virtue of this predicament, you’ve created a lose-lose situation: You’re not helping the client reach their objectives, and they’re not helping you reach yours.

Here are the two customers that I discovered too late that we should never being doing business with!

  1. The ‘no one else matters’ client. These are the clients that expect you to work only for them and all the time. They drag quick calls into 90-minute meetings, and 90-minute meetings into all-day events. They call you on the weekends on your cell phone. These relationships never work and turn ugly when their inappropriate expectations aren’t met. I fired one of these ‘I expect you to be in my office at 8 a.m. tomorrow’ clients after only one month. Life’s too short.
  2. The ‘check is in the mail’ client. You aren’t a bank, even if you work for a bank! Cash flow is the lifeblood of any business. When a client starts abusing the financial aspect of the relationship, talk to them immediately. If they will not rectify the situation, stop work until they do, or fire them immediately. No matter how prestigious. Recently a software client of mine cut off software support and turned off the online database for a client who was 90 days late with payment. The check was couriered overnight that day.

Firing a client may mean a short-term hit, but it’s critical for your long-term emotional health! Firing a client now not only frees up time for you to spend on more profitable clients, it also provides a boost of morale. When you step up and fire a bad customer, you win everyone’s trust, loyalty, and respect. Especially your own."

-- Colleen Francis, Engage Selling Solutions Founder

5) Help your customers first

"The biggest lesson I’ve learned over the course of my career is how hard it is to really focus on helping your potential customers ahead of blatant self-promotion. The best businesses put customers at the center and earn the opportunity to explain how you can help them.

You have to build some level of trust, and yet so many B2B sales and marketing professionals lead with a pitch. My advice: Spend time interfacing directly with potential customers. Look at the influencers in your space, and learn how they built their audience and the influence they have. And most importantly, simply seek to answer your customers’ top questions, challenges and concerns. The brands that win are the ones who have their eyes and ears pointed out to their community, not in toward their product team or their “sales-driven” culture.

It’s counter-intuitive, because our natural instinct as a business is to want to talk about how great we are. But that’s the last thing your customers want.

Help your customers first, and you will help build a strong and growing business."

-- Michael Brenner, Marketing Insider Group CEO

6) There’s no time like the present

"A little over seven years ago, Heinz Marketing became real. Sure, I’d registered the URL a couple years earlier and occasionally pretended to be a consultant on weekends with local businesses, but the Monday before Thanksgiving in 2008, I was finally on my own.

The stock market, you probably remember, had just tanked. My wife was pregnant with our first child. So, of course, I decided to quit my job and finally start the business that had been gnawing at me. No time like the present, right?

Seven years later, what started with a guy and a laptop is now 10 people with an office in Redmond, Washington, and clients literally around the world.

I’ve learned a ton along the way, and continue to learn every day. Here are three things that stand out to me.

  1. You are never “ready”: There are three things in my life I never would have done if I’d have waited until I was “ready” -- get married, have kids, and start a business. You’re never really ready, you just have to build enough of a plan and confidence (rational or not) to step off the cliff and give it a try.
  2. Put on your hard hat every day: There are no shortcuts. Building a business isn’t all sexy (heck, it might not be much sexy at all), but it’s the little things you have to do every day, all day, to make it work. Put on your hard hat, put your head down, check your ego at the door, and get to work. Grind it out. We can talk about strategy and business plans and focus areas all day long, but once we’re done with all that, it’s about execution.
  3. It’s exciting and terrifying: The swing between those two was definitely more severe in the early days. Today, it’s definitely more exciting than terrifying. But those variances are a reality for early-stage businesses. Again, the key is to stay focused -- focus on what’s right for your business and your customers -- and keep pushing."

-- Matt Heinz, Heinz Marketing Founder

7) The dreaded 30-day plan

"Here’s a skeleton from my closet: I was once put on a plan.

It pains me to say it, but that’s the honest-to-God truth. It was early on in my sales career, and I had not been passing as many leads to my clients as my co-workers were, and even though I knew it, I never thought that I’d be put on a performance plan because of it. My boss called me into his office late on a Friday afternoon and laid down the law: “You’ve got 30 days to hit your goal, or we’re going to have to part ways.” I was shocked. I was thoroughly embarrassed.

I began to make excuses. “It’s the client’s offering,” I said. “It’s the lists,” I suggested. I was wrong on both, and regardless, it didn’t matter: The decision had been made, and I had 30 days to get my act together or it was time to leave. Rather than give up and start looking for a new gig, I buckled down and went back to work on Monday morning with a vengeance. I made a vow to myself that I would make more attempts to connect with prospects than any of my peers.

“If I don’t hit the goal, at the very least, he can’t say that I didn’t try,” I thought.

I did just that. I made sure that each night before I left the office that I had made more calls than any of the other SDRs. At the end of the 30 days, I had hit my number and then some."

-- Chris Snell, ezCater Head of Partnership Sales

8) Don’t take referrals for granted

"Wow, was that bad. I just had an in-person meeting with the CEO of a prospect that went so poorly it lasted fewer than 15 minutes. A good friend of mine joined this company as VP of Sales and wanted to bring me in to train the team on prospecting skills. It was a small and diverse team with some field reps who had been in sales for 20+ years and some newbies. The VP had been through the training before, so he knew exactly what it was about and believes in it 100%. He’s actually one of my biggest advocates. Needless to say, the CEO, who had never invested in outside training before but believed in investing in the team, wanted to meet with me to review what I was going to go through with the team.

I prepped for the meeting as usual -- did my homework, looked on LinkedIn, reviewed their website, came up with some specific questions, set my goals, etc. The one thing I didn’t do was send a “shared agenda” before the meeting and ask him what he wanted to make sure we covered during the meeting. If I had done that, I may have saved myself the headache of what happened.

I started the meeting as I usually do, reviewing what I knew about them and then asking something specific about him, their business and where he wanted to take things. He immediately hit me back with, “I could talk about that for an hour, and we don’t have that much time. I was under the impression you were going to show me what you were going to go over with the team so why don’t you just tell me what you got.” It was very abrupt and direct and usually the response I expect when someone asks a question like, “Tell me about your business.” I thought my question was a little better than that, but I guess not. The meeting went downhill from there since it now had somewhat of a negative tone to it. I tried to get it back on track, but nothing worked. He kept interrupting me and picking apart what I was saying even though a lot of what he threw at me was the information I was trying to gain from my initial questions that he didn’t want to answer. Needless to say, the meeting lasted fewer than 15 minutes, and we walked away agreeing to disagree.

So what’s the takeaway? First, regardless of how strong the referral you have into a prospective client, make sure you don’t take anything for granted. I may have been a little too comfortable walking into this meeting based on my relationship with the VP. Second, always ensure you align expectations before you walk into a meeting on what you are there to talk about. If I had sent a shared agenda and asked what he wanted to review during the meeting, I probably would have known walking in that all he wanted to do was see what I had and I could have either addressed it sooner or changed my approach.

All in all, I was actually fairly happy about the whole experience. It had been a long time since I got punched in the face during a meeting with a prospect, and this woke me up a bit. It reminded me that you always need to bring your ‘A’ game, you can’t miss steps and you need to and must focus on getting better every day in sales."

-- John Barrows, John Barrows Sales Training & Selling Techniques Owner

9) Put in the work

"I learned the hard way how important it is to actually meet your target audience, instead of simply reading a persona document and thinking you know them.

You need to hear the language that your prospects use: How they describe their world and their challenges.

Whenever we skip this step, we regret it. Whenever we invest this time and effort, the results multiply. The underlying lesson: don’t be lazy.

Put in the work.

It’ll show."

-- Doug Kessler, Velocity Partners Co-Founder and Creative Director

10) There are lies, damn lies, and statistics

"I have a confession to make. Even though I’m “the numbers guy” at The Bridge Group, Inc., my formal math education ended with high school calculus.

Early on in my career, I believed every statistic that I encountered. “Does it have a decimal point? It must be true!” Then, one day I made a pitch to my then-CFO on why we needed a new, bright, and shiny technology. I trotted out every acceleration, impact, and ROI stat the vendor supplied.

The CFO, far from being blown away by the overwhelming “scientific proof,” dug into each number -- picking them apart one by one.

I was mortified.

I learned a hard lesson that day: Math is a weapon both for good and ill. And I decided to dedicate myself to improving my math fluency. More than 10 years later, I’ve made good progress, but I have miles more to learn.

If you’re like me, and want to hold your own, here are a few resources that I can’t recommend highly enough: The book Naked Statistics, the Coursera class Analytic Techniques for Business, and Professor Jason Delaney's Youtube channel."

-- Matt Bertuzzi, The Bridge Group, Inc. Sales and Operations

Liked these lessons? Learn what it takes to customize your team’s sales messaging to attract more customers with concise, relevant and exciting copy with QuotaFactory's Sales Development Messaging Toolkit.

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