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!

Why MQL’s are Bullshit



MQL’s are bullshit. There I said it. Let the marketing folks revolt! 

I see the amount of content out there that maps a buyer’s journey into these complex funnels to acquire users in a staged approach. I read the blogs on how to write content to your customers in each stage to encourage them to move to the next. I’ve even given these meetings first hand to my own team. So I’m here to tell everyone to stop with the funnel, it sucks. 


The reality is that MQLs are yesterday’s news – even the Buyer’s Journey is an outdated approach that needs a major overhaul and rethinking. Why? The funnel no longer exists the way it once was. As opposed to a funnel, we need to start looking at the sphere of engagement on how a prospect bobs and weaves through your content that’s appropriate for them as an individual.  The funnel doesn’t accurately describe the progression of a buyer from Awareness to Conversion. The reality is that we’re all influenced in different ways from different sources.

Before I go into what’s wrong with the Buyer’s Journey, let me first tell you what I think is right:

What’s right with the buyer journey

Being Empathetic is Crucial

The Buyer’s Journey incites good customer-centric thinking that we should all by this point have embodied into the content we write, the conversations we have, and the value we provide. We must move beyond merely saying this to actually embodying these qualities so they are obvious from the outsider that this is something your organization embodies in spirit and mind. (It’s like in Kindergarten when we all learned to “Show AND tell.”)

Multiple Touchpoints

In direct marketing, customers consider twice as many sources of information before buying than just a few years ago. We’re all doing more research than ever prior to converting. In B2B, we’re reading expert posts on LinkedIn on relevant topics, we stalk products at trade shows in the distance trying avoid talking to the booth, we talk to colleagues about what they use, and so forth. In B2C the audience is looking at your content or products that follow them around through retargeting ads, shares from their network, and in search. The point is we, as buyers, have fewer conversations with real people that drive to a purchase and subscription.

Attributing a sale to a single event is incorrect

To the point above, rarely is there a single driver for a purchase decision. The Buyer’s Journey acknowledges that and aims to reveal the important touchpoints that a marketer can affect along the way. Understanding where the prospect is before a salesperson engages is more important than what you say. There’s nothing more annoying than sitting through a presentation about the “problem” if you’re way past that point and want to talk about solutions. “Yes, I understand that I have a problem, please catch up to me on how to solve it.”

What’s wrong with the buyer journey

As I said before, the marketing funnel is inaccurate and misleading when taken literally as a step by step or stage by stage approach. Like any broad concept, the Buyer’s Journey can be stretched too far.

Prospects are Individuals, not Stages

Grouping your prospects into stages doesn’t necessarily make you understand them better. The amount of technology we have at our fingertips to understand every one of your audience members on an individual basis is here.

The act of mapping all these wonderful touch-points in the Buyer’s Journey and building a platform to coordinate them in a workflow is there. Mapping a Buyer’s Journey and instrumenting behavior on an individual level just can’t scale properly and in the time it take for you to build something custom, habits will have already changed.

Touchpoints vs. Psychology

Let’s talk this through – a prospect gets an email, goes to your website, and looks at that piece of content before bouncing. Days later they read a post on LinkedIn or Facebook and follow the link to your webpage before bouncing again. Weeks later they Google a business problem or topic they’re researching and browse four sites with credible expertise including yours, yet this time they look at some other suggested reading for them and bounce because it’s not relevant to them… and guess what? They bounce again. Understanding their behavior, learning about the psychology of the actions they’re taking, and mapping it to the appropriate content that they’d like read next will separate your brand from everything else they’re reading.

Without Proving ROI, You’re Dead

If we cannot measure and understand the contribution to a purchase or sale for the dozen or so touchpoints along a journey and explain the lift in keeping the prospect engaged before conversion we lose our marketing budget. Period. Now matter how good the model seems, if it cannot be measured, eventually we will give up on it.

B2B Buying Decisions are Made by Committee, Not an Individual

That’s a lot of Buyer Journeys to map. How many people inside an organization influence a buying decision? Rarely is it one. For my sales team, if they are forecasting something they believe they can close, and they’ve only spoken one person about their business challenge, I tell them point blank it’s not going to close – at least not when they predict it will. Typically it takes 3-4 members in a committee when companies make a decision on buying a product. How do you manage to understand all those journeys and affect them?

“the reality is that the funnel isn’t accurate and neither is a step by step approach”

Time to Evolve

As I said from the start, there’s a lot of good things that come from the Buyer’s Journey, but the reality is that the funnel isn’t accurate and neither is a step by step approach from “Awareness to Engagement to Business Value to Purchase”. We just have to decide how we are going to change our marketing practices to align ourselves with a funnel that accounts for many erratic steps in non-linear ways from multiple sources and the only way to understand how to market is to understand our audiences as individuals.