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

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Megan Tonzi
Megan Tonzi



If you’re new to sales, you may have experienced a steep learning curve making the transition. Making mistakes is part of the process, but why make them yourself if you don't have to?

Sales rep implementing sales lessons learned in training

After working with hundreds of sales and marketing professionals, we’ve had the opportunity to 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 our HubSpot team and industry experts have learned during their careers.

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Check out these anecdotes of wisdom and advice from our HubSpot sales team and network of trusted industry professionals.

1. Don’t underestimate the importance of the discovery call.

“The discovery call is the most important part of the sales process for determining whether or not a client is the right fit. Recently, one of my mentors suggested that I start the call by asking ‘what are your expectations for the call?’

I often can determine based on their answer whether they are a serious buyer or not. I look for budget, industry fit, timing and whether the company is growing rapidly or has plans to grow.

A lot of issues can be prevented by having a really good discovery call. That’s the place where you disqualify people and also learn about the pain points. Listening in sales is so important.”

Jula Pereira, HubSpot Small Business Growth Specialist

2. Be likable.

“People buy things from people they like — be yourself, but more importantly, just be likable and relatable.”

Deidre Henry, Zillow Growth Advisor, Partnerships

3. Don't get hung up explaining features. Focus on how your product or service solves for the customer.

“I definitely focus on benefits over features. I can talk about features and functions all day, but the prospect doesn’t care about those necessarily. They want to be able to solve the problems in their business.

If I am focusing on a specific feature which the prospect has a question about, I will make it very applicable to them and talk about how it will serve their particular needs and business.”

Jula Pereira, HubSpot Small Business Growth Specialist

Zillow’s Deidre Henry agrees.

“We live in a world of ‘what's in it for me?’ If there isn't a perceived value or benefit, there won't ever be a sale.

Deep dive into how this benefits your client — does this create efficiency for them? Once you paint the benefit picture, it's easy to explain the features or attributes of the product to illustrate how the job gets done.”

Deidre Henry, Zillow Growth Advisor, Partnerships

4. Being successful in sales takes grit.

"As cheesy as it may sound, pressure makes diamonds. If you aren't prepared to have a sales target, sales might not be the field for you.

It's about having grit and actually finding sales exciting and challenging. Making quota is about breaking barriers and doors down and it takes a certain personality to thrive off of that pressure! It gets my blood flowing and I can't envision myself doing anything else!"

Deidre Henry, Zillow Growth Advisor, Partnerships

5. Always be prepared to demonstrate your expertise.

Sometimes you’ll be put on the spot. TopRank’s Lee Odden learned the importance of having a few stories in your queue to demonstrate your expertise on a given subject.

"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

6. Knowing your audience and buyer personas are key.

My career started selling restaurant coupons door-to-door. 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.

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 downtime 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

7. You will make mistakes, but they are a necessary part of growth.

"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.

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. 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, President, Shore Consulting

8. 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:

  • 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 AM tomorrow’ clients after only one month. Life’s too short.
  • 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

9. Focus on solving for the customer.

"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. 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 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

10. Use the 30-day plan as motivation.

Sometimes your efforts will fall short. Here’s what Chris Snell of ConnectAndSell learned after being put on a 30-day plan.

"Here’s a skeleton from my closet: I was once put on a 30-day 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, ConnectAndSell Customer Success Manager

11. Don't take referrals for granted.

Having a referral is nice, but it doesn’t guarantee you’ll get the gig. This is something sales trainer John Barrows learned the hard way.

"I 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.

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. 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, Limited Partner, GTMfund

12. Get to know your prospect.

"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

Develop These Habits and Set Yourself Up for Success

infographic: top tips from sales prosNow that you’ve read some of the blunders experienced by industry professionals, set yourself up for success with these pro tips.

1. Be an active listener.

As noted above, it's so important to listen to the needs of your prospect. It may be tempting to dive into a boilerplate pitch, but it's more important to pay attention to what the prospect is saying and not what you want to say.

Do your best not to interrupt. Restate key points you've learned from the conversation to make sure you and the prospect are on the same page. Ask open-ended questions to get a clearer picture about the obstacles they are facing.

Your goal is to find a solution to their problem and you can't do that without being a good listener.

2. Develop a routine for each call.

Both Pereira and Henry note that being prepared before each call makes all the difference when speaking to clients. Develop a habit for creating talking points beforehand.

“I try to listen to my discovery call before doing a demo so that I am prepared for the call with specific insights and examples which relate to the prospect. It helps me feel more confident in going into the demo and customizing it to them. I also have many talking points around the ‘crafted not cobbled’ concept and explaining the Flywheel to people."

Jula Pereira, HubSpot Small Business Growth Specialist

“Have a written agenda for your call — know what the goal is and have it in front of you or the call will get derailed. When you start the conversation by announcing 'this is what we will be tackling on today's call.' It puts you in control and only boosts your confidence. Confidence always closes the deal.”

Deidre Henry, Zillow Growth Advisor, Partnerships

3. Research your prospects.

You wouldn't take an exam without studying, and the same logic applies to sales. Get familiar with who your prospect is and their organization before hopping on a call.

"The most helpful thing is looking at prospects’ LinkedIn profiles. If you can read blogs or social media posts beforehand, that would be ideal as well.

Sometimes I don’t have time to research them because I have back-to-back calls. Then I will ask them on the call to describe their role in the company to give me a quick context. You don’t want to seem unprepared though, so I typically say that I saw that they are in a certain position but I would love for them to describe their day-to-day, etc."

Jula Pereira, HubSpot Small Business Growth Specialist

4. Get comfortable with hearing the word “no.”

No one likes rejection, but it unfortunately comes with the territory when working in sales. Get comfortable with hearing "no" and don't take it as a personal attack.

“Know what you're selling and practice objection handling. To ease your nerves further, remind yourself that the absolute worst that can happen is that client saying ‘no’.

Actually, you can have a week, or even a month worth of nos but after that many nos, there is a yes waiting for you.”

Deidre Henry, Zillow Growth Advisor, Partnerships

5. Don’t let sales goals or quotas overwhelm you.

Sales targets can be intimidating, and missing yours can get you down. While you may fall short, it doesn't mean you need to dwell on it. Learn where you went wrong, what could be improved, and pour your energy into performing better the next time. Pereira notes that it's important to find balance between hitting your numbers and having a life.

"I’ve realized that even if I don’t meet my quota in a particular month, I have the opportunity to change that next month. My fate and destiny are not fixed in stone.

I think that having a good work-life balance is also essential as well. I don’t work on the weekends and I have a great support system with my team, manager, friends, and family. I am more than my quota and I remind myself of this every day."

Jula Pereira, HubSpot Small Business Growth Specialist

Sell Like a Pro

Sales is a high-pressure industry, with each day presenting new challenges. Use our insider tips to tackle obstacles, delight customers, and crush your sales goals.

This article was published in April 2016 and has been updated for comprehensiveness.

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Topics: Sales Experts

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