Everyone hates to be sold, but loves a story.

Sell me this pen.

Made (recently) famous from Wolf of Wallstreet, but this question has been around long before that. It’s in this question that people can get the wrong idea of what it means to truly sell. After all sales is not about convincing, rather it’s about the story around why the pen itself represents more than an object, but solves a need that the person may or may not have thought they had. Said differently, a killer sales narrative doesn’t simply convince but motivates through emotion and inspires an action to solve a problem. In a world where many problems compete for priority, motivation to solve one of them more than others becomes the differentiator.

The key is the story, the narrative, the emotion that you can evoke from unraveling a story with imagery, words and conviction. However, before you even tell the story, you need to make people want to listen to you.

We all have caught on to scripts and cold calling tactics that list a bunch of product features. When someone regurgitates a laundry list of features you can watch the life slowly drain from my eyes. We live for more than features! Viva la Sales!

Storytelling Makes you Memorable 

Put simply, we retain information through stories. That cartoon you were watching when you were five. That story grandma told you when you were seven. When facts and data are framed within a compelling story, you will hold the listener’s attention and help them connect the bits of the story to their context.

The result of better storytelling is better retention. Rule #1 in sales is to be memorable. Rule #2 in sales is be influential. Rule #3 is to always add value. Rule #4 Listen. Rule #5 is none of this matters unless you nail Rule #1

If you pull off a great story but timing isn’t right, you’re effectively planting seeds for when your solution / service becomes more relevant. Think data breach if your selling security software or a recruiting efficiency solution when you get a big round of funding that demands you double your headcount. Guess who will come to mind?

Storytelling is becoming a respected technique that’s recognized for its effectiveness. The London School of Business did a study which confirms what was experienced by people who used storytelling as means to transfer information and convince people. In fact, when stories were used to convey the same information as when not used, retention jumped up by 70 percent.

Logic and Emotions 

Sales teams put together presentations that showcase their product in the best possible light. It’s very important that you know your product, its features and benefits, all that good stuff, but it’s not enough to get you to close. If you think this, you have to hustle much harder because your win rates are abysmal.

Features don’t sell.

Most decisions are made with both logic and emotions in play. When listening to stories with rich imagery and meaning, the brain is stimulated as a whole. When this happens, both emotions and logic are in play.

When demos, even conversations, are comprised primarily of stories, then the brain is gripped. If you can make a prospect feel, you’re in the drivers seat and storytelling connect us on a emotional level.

Vision Stories 

A perfect example of gripping the emotions of your listener are Vision Stories. Telling a story about why you’re inspired to do what you do, help who you help and most importantly, where you’re going inspire your listener to follow you. You (and / or your company) see the challenge/s that your listener faces today as a common challenge and more importantly see a world in which this pain goes away or is drastically reduced. You become the leader.

This visionary role is very effective but can blow up if not told with passion and conviction along with experience. If you’re young in sales, don’t pretend to be the visionary, rather place the visionary tag on your CEO or founder as the person who can look around corners to see what’s next. They’re the leader, you’re evangelizing a vision.

Who Am I Stories are effective in creating a bond with your prospect. Especially if you end up supporting the prospect in the post sale, you can tell how you will ensure their success no matter what happens. The bigger the purchase, the bigger the risk and when they hear someone that’s not just about selling them and handing off their success to someone else, its a powerful message. What you stand for can have compelling effects when what you stand for happens to coincide with the prospect’s success.

In addition to Who Am I Stories, you can add even more emotion in the mix with  Why Am I Here Stories which essentially showcase why you chose to do what you do which cultivates transparency around your intent. Prospects tend to become more receptive when you tell them what your trying to do because they humanize you.

Another method for Vision Stories is the FUD method (Fear Uncertainty and Doubt) which runs rampant in the software security industry as well as the insurance industry. The “Act Now or Else” mantra can be very compelling if you can back up your FUD method with stories on how people you spoke with before did not head your warning and are now suffering the consequences. The FUD method is effective when you use it in the ways your solution can prevent something bad from happening but it also is used as a cheap way to devalue competitors. If you need to use FUD to sell your prospect away from a competitor it means you can’t sell on value alone, and that wreaks of position of weakness sales techniques.  

Visualize their world 

There is no substitute in understanding the world your prospects live in. Knowing what they face each day, to include their pain and motivations, it’s nothing short of gold in sales. Smart sales people bring up common pain that a certain persona continually faces, but turning it into story form makes it visual.

Common stories can be success stories that relate your prospect to a similar challenge a customer faced, preferably in the same industry, and how they overcame that challenge with your solution / service that made them better because of it. The more you take the prospect through this process and insert color to the story, the better. Color could include initial doubts that they faced, how they took (what they thought) a risk on moving forward with the solution and what a difference it made to them personally and professionally. Cap it off with how you feel that experience is very similar to the prospect’s and have them start to visualize the same success in their world by asking compelling questions to cap it off.

“If this story was you, how would that impact the challenge you face today?”

Stories create Action

If you’re successful in making your stories relevant to the prospect’s situation and you were able to grip their attention, you are in a great position to influence their buying decision. The way you position your brand and your product in your stories is essential in getting that yes. The yes is the action, and quite easier said than getting so the call to action should be strong and authoritative. Your story needs to be in the center of logic and emotion to make sense and to cap off a great story, the action that the person must take should seem obvious, easy and rational. 

Here are some final techniques on capping a good story: 

Make it about them – Even when you’re talking about other clients or hypothetical situations, make it so that the client can see themselves in the stories and by the wrap of the story make it only about them. 

Keep stories straight to point – Be Hemingway and get to the point. You’re not writing or speaking an epic, just a case study that is intended to hook a prospect. If you prepare well, you’ll get the points across succinctly.

Use imagery – Learn to tell stories that paint scenarios. Stories are a great leap from dry presentations, but don’t make your stories dry! A great practice is to tell a colleague about your weekend and an experience that unfolded (doesn’t have to be epic) to start practicing the art of telling great stories. Aside from making you better at sales, it will make your life a lot richer. 

 Use humor – Great timing is a gift. If you have it, don’t afraid to make your prospect laugh here and there. Just don’t overdo it! There’s a thin line between clever and being a sideshow.

Sales is more about your product, service or solution, it’s about the value and who it helps. In order for prospects to truly hear you, they have to connect with you, remember you and like you.

Everybody hates being sold, but loves a story.

Why Introverts are my Favorite Sales Hires



I got a LinkedIn message from a colleague recently about helping their younger brother get into sales.

I replied, “Why do you think that he’d be good in sales?” Here’s the response:

“He will literally talk to anyone. He’s the type of person that you bring to a party and he immediately can strike up a conversation about anything. Plus, he’s very money motivated and wants to retire by the time he’s 50. I told him sales is the perfect spot for him and I thought of you!”

So much to unpack here. I’ll stay focused though and start with the first sentence because it’s time to put this to rest for good. When most people hear the word “sales person” they associate most with the following list:

  1. Fun, charming and entertaining.
  2. Display impressive knowledge or skill at something.
  3. Incredibly social, can talk to anyone.
  4. Have primal perception, they know what you’re thinking before you do.
  5. Display infectious confidence. Believe they’re better than everyone.
  6. Crave a good reputation. Defend their reputation before it becomes questioned. 
  7. Crave status and power via possessions and money.
  8. Have delusions of fame and importance.
  9. Mimic authentic emotions and sincerity.
  10. Believe what they do benefits everyone despite the outcome.

The list above is taken from a quick google search on characteristics of a con artist.  Sales is really the art of influence and assistance where is a con artist is all about manipulation and forcing decisions that benefit only them. Now don’t get discouraged if you are a con artist out there, they can get pretty far themselves, even the highest office in our country. As much as movies and documentaries end up glorifying people like this and putting Leo in the lead role, it’s really the worst personality trait I can every think of and it drives me crazy that people associate my profession with these characteristics.


The key to being successful in sales is to truly understand what drives your customers and how you could help them fulfill those needs. More importantly, exhibit behavior that is commonly associated with introverts, who also can hold the highest office in our country

Why Introverts Make Awesome Salespeople 

Introverts focus inward as opposed to extroverts, who attend to people and things outside themselves. Introverts think before they act. Conversely, extroverts tend to act spontaneously, without thinking. Great salespeople that happen to be introverted will calculate the line of their plan for the quarter / year and know the challenges they will face and what skills they need to push through those challenges. The introverted salesperson will rely on the confidence and strength within themselves to make decisions to negotiate and react to what’s happening outside their control. These are strengths introverts possess, among others.

When someone asks me what I look for in good sales hires, I tend to focus on qualities that make up an introvert at heart. Introverted salespeople tend to:


Immerse themselves into what they sell and who they sell to

Introverts know what they have on a deep level and when they don’t they spend countless hours closing that gap with as much knowledge as they can. When you begin speaking to an introverted salesperson, she will be scanning their knowledge to judge whether or not they can help you. Before they even begin to talk to you about what they have, they will determine if you are a good prospect to spend time with. They understand it takes more than a pulse and a wallet to make a good sale. They qualify opportunities very well and understand that because they need to immerse themselves into their buyer’s perspective, they can’t spend that time on every prospect that enters their funnel.

They Read the Room

I’ve been impressed with sales people that were able to “wing” a situation but I’ve never seen anyone “wing it” in a sophisticated sales cycle. The best of the best know exactly what they should say in any given situation and know who will most likely throw them a curveball during a meeting. They study customer reactions to certain phrases and adjust their vocabulary accordingly and mention phrases like “reading the room” for body language when presenting face to face. They read a lot of material on how to become better in their profession and are relentlessly trying to improve themselves. Lastly, they realize they will likely only get one shot to present their product, so they make it count.

Think about the LTV of their Customers

Many extroverts will have dozens of casual friendships. They can go anywhere and meet people they know, hang out with them for a few hours, then head home. It’s easy to make connections, but because they are connected to so many people, it’s difficult to develop deep relationships. When it comes to sales, this leads to many short-term successes with angry customers on the back-end.

Introverts tend to have fewer, but deeper relationships with their customers. They really want to get to know the customer and help them over time. They aren’t looking for a single sale to get a bonus; they’re building a list of clients they can service for years, which creates a constant stream of referrals and repeat business. This is the long tail approach to sales and is typically found in an enterprise sale.  It takes longer to build this type of sales cycle, but it’s the only way to create long-term success so it only makes sense in enterprise sales. If you work in a high velocity sales model you can get away with the alternative approach and it typically lends itself very well to extroverts – because the deal value is lower, so are the expectations. So if you let a prospect down, it’s doesn’t get them fired. In Enterprise, this can follow you around wherever you go so that if you work with enough companies that have shitty products you should think about making changes to your vertical market you sell into.

The Best are Introverts and Extroverts

There are sales jobs for the talkative, loud, constantly laughing guy that is the “born salesman” but it’s not in the industry of selling sophisticated, enterprise grade products or services. It’s the quiet, introspective, hard-working person that will know how to “turn it on” when needed but spends most of their energy plotting and preparing for the chances they can win at that will win the large, enterprise deals. But it’s not enough to be great.

Let’s be honest, the ability to approach people is crucial in sales as is the capacity to handle rejection. These are both two main pillars of an extrovert and very important in sales as well. The ideal salesperson is an extrovert who learns how to be an introvert or an introvert who embraces the skills needed to be an extrovert. The difference tends to be that introverts will often work hard to develop the extrovert’s skills, while the extroverts will continue to try to get by on their natural charms.

As an extrovert, you can still be a top performer in your field; simply take the best qualities of introverts and pull them into your sales style.  Don’t let ego get in your way of you mastering your craft. 

The Wisdom of the Dog Whisperer and Sales Leadership


Having a Golden Retriever and two kids, I naturally watch a lot of dog training shows. 🙂 Before you think I’m completely degrading my kids, “The Dog Whisperer” speaks more about the principles of being a parent or even a VP of Sales than just a pack leader to your pet. It’s about the importance of rewarding good behavior and disciplining for bad. The most important factor in these rules is being consistent with the rules.

If you are not consistent with the rules, (i.e. when the same behavior is sometimes rewarded and sometimes punished) the dog becomes stressed, confused, and starts to take no commands at all.

I’ve seen this dynamic more often than not with sales managers. It’s very common in new managers but it’s very concerning when you see it in a VP of Sales – how long have you been leading this way and how did you get to this position?

An example of this would be celebrating the deal more than the process of getting a deal closed. Closing a deal is the result of the fuel you put in every day, the prospecting, the check in calls, the nurturing angles, the business cases, the art of a good proposal, the buyer call, and more importantly – the “pick yourself up, dust off and do it again” side of sales. In fact, the best sales people make losing look like winning because they did everything necessary to close the deal, but instead of closing the deal they found a way to get a win in other areas. If you pay attention to this process, the little wins during the process and celebrate the execution of it, the more deals will come – that’s predictable success.

If the individuals on your team feel like they had a successful day than they are more inspired to succeed the next day. Setting the right expectation on a daily basis will help your folks understand whether their day was a success or not.

As an example for front end sales:

Did you send out 20 emails, connect with 10 people, write two new posts within your LinkedIn groups that are knowledgeable, share 3 times and comment twice on twitter posts from your network in a positive way and end the day with a clear definition of what the plan to achieve your ultimate goal the next day.

Sales is unpredictable, but this is predictable – if you do it every day than you can predict success.

If sales folks aren’t putting in the effort on a daily basis to fuel and influence their pipe, then you have to either look at yourself to figure out whether you acknowledge the fuel in the first place or, if you do, tell the person who isn’t putting in the effort what’s expected – if they don’t perform the basics they will never master the art of sales.

If done well, you will lead a culture of predictable success but if done poorly and celebrate the deals that didn’t follow any process or rhyme, you run the risk of dismantling everything. You need to be understand that in order for this to be a success you need to set the tone that success starts with consistently hustling, practicing and achieving on a daily basis. This isn’t meant to be a micro-manager type of quota system but an emphasis on the importance of the basics.

We’re no different than dogs, we like routine, structure and direction which will open up what is possible within every sales person. If every day’s success weighs on whether or not deals are coming through than your team will only be focused on pressure tactics to close business (the wrong way) as opposed to nurturing, challenging and selling solutions (the right way). If everyone is anxious about the consequences of not closing a deal every day, they won’t pay attention to what actually closes business – the process.

Think Outside Your Own Box


Stop me if you have heard this before, a sales leader is frustrated with how their folks don’t “think outside the box” or “embrace innovation” or my favorite “connect the dots”. My answer to this is most sales leaders don’t reward creativity, that “box” you talk about that your sales people need to “think outside” is your own aversion to creativity.

Think about it. When a creative idea comes from your team – do you listen to the idea or do you pay more attention to the vehicle presenting the idea. The more unproven the person presenting the idea is the more risky it will be for the VP to back it, support it and embrace it to the masses.

Everyone in theory wants innovation, but most also want to remain in control of what they are comfortable with – being uncomfortable is after all … uncomfortable.

If the consequence of failing is met with the positive support to do it again, people will stick to innovating, working hard to improve and to get the big reward. If everyone is anxious about the consequences of failure then they will feel more comfortable doing what they’ve always done, how they’ve always done it, and reap the same results – ultimately never realizing their own potential.

This behavior inevitably creates a self-defeating pattern. If the company doesn’t create an environment where people can take risks and occasionally fail, then innovation will be stifled. If innovation doesn’t occur, the company won’t grow, the team won’t succeed past expectations and the result will ultimately lead to monotony at best. This environment will create anxiety to the point that the cycle will repeat until the fear of failing ends up hindering progress to a point that failure is inevitable. This type of failure cripples the ability to get back up.

What can you do as a manager to create an environment that fosters innovation?

1) Evaluate. Look at your team and assess how often people are avoiding risks in their current position. Utilize ways to gauge the overall feeling of your employees by open team meetings or one-on-ones to find out if people are holding back ideas and are caught up in the fear of failing. If it’s happening, talk about how you can improve and what you can learn from their innovations and risks as well as how it can propel their career forward. Everyone wants a vision of being greater than they currently are – it’s even more powerful if that vision is shared.

2) Encourage and Share Ideas. If you create an environment that is safe for an employee to share ideas, concerns or feedback without fear of retribution or a negative impression people will start looking for ways to improve the company or team. They all talk about what needs improvement as it is, so you might as well make it constructive for you. The key is to make it comfortable for people to share their ideas; once they are on the table you can choose the most effective ones to implement.

3) Experiment and Commit. Take a chance on some ideas and commit to them for a certain period. Understand that the best ideas are not the most obvious ones so give them a shot. Don’t be one of those VP’s who say they’re trying the new idea but don’t commit to it – your team will see through it and it will backfire, so you’ll be worse off for even saying you’re doing it. Make it explicit that failure is acceptable as long as something is learned. You learn more in failure than you do in success.

4) Reward for the risk, not the result. Your people need to be rewarded and reinforced for taking risks, so don’t give mixed message on whether or not it’s acceptable. If you want more risk taking, reduce the conflicting signals and create an environment where the benefits of taking a risk outweigh the fear of failure.

If you are looking to manage “C” talent and hope to work at a company that builds a product or service that sells itself then don’t pay attention to any of this – sit back and watch your skills rot. If you are looking to manage “A” talent, regardless of what you sell, you need to embrace the idea of fostering creativity, innovation and the industry’s next Sales leaders. Let our future leaders breathe!