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Sales Leaders, The Sales Evangelist, Donald C. Kelly

TSE 1181: 3 Things Leaders Do To Hurt Sales Rep Relationships



Sales Leaders, The Sales Evangelist, Donald C. Kelly

Sometimes, there are 3 things leaders do to hurt sales rep relationships and most times, they do it unintentionally. This is especially hard because sales leaders and sales reps spend a lot of time together. A bad leader can negatively affect how a sales rep makes his sell. While a good leader helps how sales reps can improve their sales. 

Marc Levine founded his ImprovMySales business four years ago. The company is dedicated to creating wonderful and profitable places to work. Before this business venture, Marc was part of a sales team as a national account executive and technology and professional services. For the last 16 years, he has been developing leaders and teams, teaching people communication skills, selling services to certain companies including Citibank, Prudential, and Best Buy.  

3 things leaders do to hurt sales rep relationships

There are probably more, but let’s focus on just the three things for now. 

  • A leader does not create a psychologically safe environment
  • The leader forgets about humanity 
  • The leader is emotionally unintelligent

August has been a leadership month and people have been talking about the important things to become a good sales leader. This involves setting a vision and becoming a good coach. It’s about creating a culture where sales reps can thrive and succeed. 

When a leader fails to create that safe environment, the sales relationship takes a hit. 

By definition, psychological safety was a term coined by the social psychologist, Amy Edmonson. Google did a two-year study and analyzed the qualities of its most effective teams. The results of the study have shown that teams promoting psychological safety produced better revenues and their team members stayed in the work longer than others. Psychological safety is a team norm that says it’s safe to take risks, to be vulnerable, to ask for help, and to disagree with the rest of the team. 

When you do, you won’t be ostracized for disagreeing but instead, you’ll be honored and validated. 

An environment where sales leaders can thrive

As a parent, when your kid doesn’t understand something, you want your kid to feel safe to come to you and ask for help without getting embarrassed. The same is true in sales. As a leader, you need to develop a team where your members can be honest and can come forward when they don’t understand something. 

You want your team members to come to you about their problems early on in the sales cycle rather than at the end of it where the deal is falling apart. This is the essence of psychological safety. 

It’s an environment where people can ask for help, be vulnerable, take risks, and be supported 

Create a psychologically safe environment 

This doesn’t happen overnight. It happens when your sales reps come to you asking for help and instead of reacting, you validate and support them. Do it a couple of times for the team members to realize that you want to help them. 

Sales leaders also need to stop blaming the team members. Blame and accountability are two different things. 

Blaming makes the blamed feel bad and threatened. It’s when sales leaders bombard the reps with questions like: 

  • Why didn’t you hit the quota last month?
  • What are the reasons why you lost that sale?
  • Why aren’t you doing this?

These questions foster negativity. Accountability helps you raise the team’s standard without making the reps feel bad. It’s more like saying, “Hey you didn’t hit your quota last month and I know you’re disappointed. Let’s talk about what happened that may have contributed to this and let’s figure out the solutions.” Build an environment where your members can be comfortable in having a dialogue. 

As a sales leader, you also need to admit your own mistakes. Research shows that when you admit your mistakes, the people around you will come close and will open up about theirs as well. 

There’s power in vulnerability and when you use that power, you will see your sales team come closer and open up to you. 

Leaders forget about humanity 

The next in the list of the 3 things leaders do to hurt sales rep relationships is forgetting about humanity. 

Salespeople are like stand-up comedians. We go out there showing confidence knowing that we’re going to be rejected. We are a fragile group. When sales leaders remember the humanity of the people on their team, the members tend to go above and beyond. The members put in incremental efforts. 

Sales leaders also need to stop making the team members like little versions of themselves. Every member is unique with their own set of skills and strengths. Forcing things that you do well onto them will make them feel resentful. Instead, honor their strength. Validate the things that they do well to make them feel excited and engaged. Make them feel heard and understood. 

Remember that you are working with human beings who have hopes and fears. and get scared. Honor that part of them. 

Build strong relationships with your sales team

Sales leaders need to build strong relationships with their team and practice emotional intelligence. Daniel Goleman wrote in his book Working with Emotional Intelligence that people with emotional intelligence are more successful in their careers than those who are just relying on pure intelligence. Emotional intelligence is the ability to understand and regulate your own feelings to understand and empathize with the feelings of others. As a sales leader, you need to be aware of your emotional triggers to be able to manage them. If you fail to develop that, you can easily be overtaken by your emotional triggers and start to judge your team. 

These triggers tend to show up again and again and these are no surprises. 

Some of the triggers are when your sales rep didn’t hit the quota or when someone in your team isn’t adapting to the new technology, and when someone’s not putting something into the CRM.

So, list your triggers and think of all the situations and the people that trigger the fight, flight, or freeze responses.  

The sales team and all its members are the backbones of an organization. We want them to feel empowered and we can’t make that happen if we don’t provide them an environment where they can thrive and if we keep blaming them. Have conversations with them and make them feel good so that they’d want to produce for you. 

“3 Things Leaders Do To Hurt Sales Rep Relationships” episode resources

Connect with Marc at or reach him at (718) 637-7890. 

If you like this episode, don’t be shy and give us a thumbs up and rating on Apple Podcast, Google Podcast, Stitcher, and Spotify. We produce podcasts weekly so make sure to subscribe to get more of these sales talks that matter! Share this with your friends and teach them how to subscribe as well. 

This episode is brought to you in-part by TSE Certified Sales Training Program. It’s a helpful guide for sales reps and sales leaders to improve their pitches and presentations. It has 12 courses and you can get the first two modules for free! If you want to take your sales to the next level, then I recommend that you join us with our group coaching. 

If you’re a sales rep looking to hone your craft and learn from the top 1% of sellers, make plans to attend the Sales Success Summit in Austin, Tx, October 14-15. Scheduled on a Monday and Tuesday to limit the impact to the sales week, the Sales Success Summit connects sellers with top-level performers who have appeared on the podcast. Visit to learn more and register! 

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Hiring, Liam Martin, Donald Kelly, Remote Sales Team

TSE 1059: Sales From The Street – “Building A Remote Sales Team”

Hiring, Liam Martin, Donald Kelly, Remote Sales Team

For business owners looking to scale their efforts, there are important factors involved in building a remote sales team, and implementing them can mean the difference between success and failure.

Liam Martin runs three companies related to managing remote workers:,, and his passion project, which is a conference on building and scaling remote teams. His organization helps companies monitor their remote employees’ productivity and efficiency.

He points to the fact that, early in his career, he waited too late to build a sales team, which is the meat-and-potatoes of his business.

Create solutions

Founders of a company have an understanding of the product or service that most sales reps won’t have. Founders may recognize as many as 10 different problems that you could tailor your product around or have meaningful conversations around.

Sales reps won’t necessarily recognize that many problems, so they may not have access to as many meaningful conversations.

The key, then, is hiring a proper sales manager. Sometimes the founder’s ego causes him to believe that he can effectively run a sales team, and he doesn’t recognize his shortcomings.

You must take a hard look at yourself and determine whether you’re truly a good sales leader. When Liam recognized that he wasn’t a good sales manager, he fired himself and hired a proper sales manager.

Be honest enough to determine what you can best do for your organization and then do that.

 Hiring process

Liam’s company has three different stages of hiring remotely. He suggests that many remote teams aren’t as effective as the leadership believes they are.

Liam points to the bullpen, or the area where junior employees are grouped together in a single workspace. The idea is that the employees will train and work together and benefit from one another’s experiences.

Remote employees don’t have a bullpen so it’s impossible to pick up nonverbal selling techniques that some employees are successfully using. Everyone is disconnected, so very often these sales teams won’t hit quota despite their training. As a result, they leave the company.

To solve the problem, Liam’s company works with remote salespeople for about a month. During that time, he has to either close an inbound deal or generate some kind of outbound activity. Based on that success, the company decides whether to invest more into the employee.

He says that although it’s an expensive system, building a remote sales team is ROI positive.

Self-motivated activity

Successful remote employees must be self-motivated. Once the company hires a new remote employee and decides to invest in him, the company flies him to the sales manager in Canada where he will train in the office for three months.

The employee will either hit quota by the end of three months and will have a job, or he will not hit quota by the end of that time, and he will go home without a job.

From that point, the system rewards good salespeople financially. Successful sellers will earn more with this company than they will at other companies. At the same time, the pay structure is such that unsuccessful sellers won’t be able to survive.

The first three months, then, are critical to the seller’s success. Creating the bullpen experience has helped the company’s remote sellers be more successful.

Additionally, the company allows any employee to jump in on any Zoom call to ask for help or guidance.

Massive investment

Liam points to a need to identify those sellers who can talk the talk but can’t walk the walk. Because the company is making a massive investment into its new hires, it must be able to quickly determine which employees are likely to be successful and which ones are not.

On average, his company has found that it can take anywhere from three to six months to determine whether an employee will be successful. Its goal is to shorten that period when possible.

The company would prefer a clear “yes” or “no” to a “maybe.” The more time it spends dealing with an employee who is a “maybe,” the more money it invests without fully knowing whether it will get anything in return.

“Building a Remote Sales Team” episode resource

If you want to learn more about building or scaling a remote team, visit It’s a conference being held in Bali, and if you’ve never been to Bali, it’s another great reason to go.

If you’d like to get in touch with Liam, he’s excited about his interactions on YouTube right now, and you can find him at After consuming the content, feel free to ask questions in the comments and he’ll be happy to respond.

You’ve heard us talk about the TSE Certified Sales Training Program, and we’re offering the first module free as a gift to you. Preview it. Check it out. If it makes sense for you to join, you can be part of our upcoming semester in April.

You can take it on your own or as part of the semester group. The program includes 65 videos altogether, and we just completed a beta group that helped us improve the program and maximize the information in it.

This episode is also brought to you in part by, a Chrome browser extension for Gmail that allows you to track and schedule your emails. You’ll receive real-time alerts anyone opens an email or clicks a link.

I hope you enjoyed the show today as much as I did. If so, please consider leaving us a rating on Apple Podcast, Google Podcast, Stitcher, or wherever you consume this content and share it with someone else who might benefit from our message. It helps others find our message and improves our visibility.

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Brian Manning, Donald Kelly, PatientPing, hitting your quarterly number

TSE 1016: How to Deal With The Pressure of Hitting Your Quarterly Number

Brian Manning, Donald Kelly, PatientPing, hitting your quarterly numberWe’ve all experienced that sinking feeling in sales as we near the end of another month … so how do you deal with the pressure of hitting your quarterly number? It’s not easy, especially without the proper guidance.

Brian Manning, SVP & Head of Growth at PatientPing, works to help startups grow their ideas and he is here today to share insight on how to deal with the pressure of hitting your quarterly numbers.

PatientPing is a care coordination platform that helps healthcare providers collaborate with one another on shared platforms. Brian has been with PatientPing for three years now. He oversees their sales, marketing, government affairs, and partnerships.

From a sales leader standpoint, Brian thinks of quarterly numbers in terms of the Annual Recurring Revenue (ARR) for each layer of the business: the overall company ARR, the sales team ARR and the individual sales rep ARR.

Will, Should, Could

Sales reps often feel the pressure to perform and, as a leader, Brian likes to have his reps 3x their pipeline as they enter the quarter. As the quarter goes on, however, and things become more sophisticated, Brian moves on to the ‘Will, Should, Could’ method.

This method involves marking each deal throughout the quarter as Will Close, Should Close and Could Close.  Wills usually equal about 95%, while Should is at 70% and Could is closer to 50%. The Sales Operation Team does this for each week for each rep to provide a projection for the quarter.

In this way, at any given week, the reps have a pretty good sense of where they stand in relation to their targets. Brian has found that the projections are smart and reliable.

The detective mindset

When sales reps feel pressure to hit their quarterly numbers, it is usually a result of a failure somewhere in the sales funnel. There might not be enough leads, the presentations may not convert into proposals, or the deals may be stuck in contract too long.

It is usually one specific thing that slows them down. It almost takes a detective mindset to figure it out sometimes, but it can be done.

A key factor in reducing the pressure of hitting your quarterly numbers begins with the numbers that are expected of the sales rep.

The rep needs to be comfortable with those numbers.

If they do not see a path toward achieving the goal set in front of them, they need to alert their manager right away – before the quarter even starts.

It should not be viewed as a sign of weakness, nor should a rep fail to come forward because of pride.  

As a manager, Brian knows it is important to listen to his team. The territory could be bad, the ramp might be too quick, or the training may need to be improved.

He does, however, require an intelligent and well-thought-out conversation rather than simple excuses.

You never want to send a rep out to achieve a quota he doesn’t feel he can meet. It’s not healthy for anyone.

With their detective hats on, the manager and the rep can then work together to specifically analyze the territory, the opportunity, and the various stages that the deals are in.

It has the benefit of making the sales rep more effective which, in turn, increases the likelihood of hitting the numbers in subsequent quarters.


When the pressure is high or the number is high, it is especially important to take care of your health. Brian believes that nothing is insurmountable when you are feeling healthy and well.

A seller under too much pressure – one with any type of resentment towards the product or the company  – will not be a seller who gives his best. It will translate into his performance and affect the clients and the sales.

When a salesperson puts his energy into dealing with the things that he can’t control – an imperfect product or lack of marketing team support, for example – the salesperson will always lose.

In Brian’s experience, the number one difference between a great seller and a not-so-great seller is that the energy of the great seller goes to the areas where he has control. Don’t waste energy on things that will not help you reach your numbers, or succeed.

Your energy, as a salesperson, needs to go into selling under the conditions you are in. This does not mean, however, that you should hesitate to flag issues. If there is something wrong with the product or the process, it should certainly be brought to the attention of management.

There will always be that one guy who wants to complain regardless of the situation. But those reps that can focus and channel their energy into doing what is best for their client are the reps that will succeed.


There is a seesaw to transparency. When a rep is doing really well and is on track to reach his quota, his manager will see it and will know the rep is doing fine. There is no reason to stress.

But if the rep isn’t doing well or the numbers are low, transparency needs to increase. Brian suggests something as simple as a weekly email to management to address what is working and what is not working. Being really honest and vulnerable in this way provides management with the information, and the opportunity, to improve the system. It helps everyone in the long run.

Many of us don’t like to admit when we are having trouble but it is always easier to address a problem when it is small rather than waiting until it is too big to handle.

Brian has found that, generally speaking, most sales reps that want to work for a start-up are self-starters. They are the ones who read sales books and listen to podcasts to further their own learning.

Horizontal learning

Over time, as a company grows, Brian will bring in sales trainers to coach and shadow. Until a solid infrastructure is up and running, however, Brian has created a system where his sales team sends out a weekly ‘Wins and Learning’ email to each other.

He also stresses that a good learning experience is more valuable than a big win. His team has become competitive to send out the best learning which scales across the team.

  • Be analytical
  • If you are doing well, document how you do it.
  • If you are not doing well, document why not. Be honest and lead the charge into fixing it.

“Hitting your Quarterly Numbers” episode resources

Brian has maintained a blog for the past ten years at He is also on Twitter.

If you haven’t already done so, subscribe to the podcast so you won’t miss a single episode. Share it with your friends who would benefit from learning more.

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Previously known as TSE Hustler’s League, our TSE Certified Sales Program offers modules that you can engage on your own schedule as well as opportunities to engage with other sellers in other industries.

This episode is brought to you in part by, a Chrome browser extension for Gmail that allows you to track and schedule your emails. It’s super easy, it’s helpful, and I recommend that you try it out. You’ll receive real-time alerts anyone opens an email or clicks a link. will give you half-off your subscription for life when you use the Promo Code: Donald at check out.

I hope you enjoyed the show today as much as I did. If so, please consider leaving us a rating on Apple Podcast, Google Podcast, Stitcher, or wherever you consume this content and share it with someone else who might benefit from our message. It helps others find our message and improves our visibility.

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Women in Sales, Barbara Giamanco, Donald Kelly, The Sales Evangelist

TSE 861: Stepping Up And Standing Out As Women In Sales

When companies make a conscious effort to attract women, it’s good for the business on all levels. Women are often more consistent at exceeding quotas, and they’re strong leaders as well. But there’s another component as well: stepping up and standing out as women in sales.

On today’s episode, we’re talking with Barbara Giamanco, host of the Conversations With Women In Sales podcast. Her lifelong passion to help women in business has led her to try to impact the presence of women in sales by influencing the women and the businesses who hire them.

The case for women

In a global report called Gaining the Talent Advantage, researchers found that 62 percent of companies who have 45 percent or more women in their ranks drove higher-than-average levels of profitable revenue.

Having a more diverse team makes it easier for you to connect with people on multiple levels. There’s a case to be made for the money.

The problem isn’t simply that companies aren’t hiring women. Some women hesitate to lean in to new opportunities.

Barbara said that women often put their heads down and work, expecting that someone will notice their efforts. That may or may not be true.

On her Razor’s Edge podcast, men make up 98 percent of the people who request to appear. They have no problem asking to be noticed, while women aren’t as comfortable.

Women often doubt their expertise and downplay what they have to offer. They also fear that pointing out their own successes will be perceived as bragging.

Sharing your experiences is good for the entire sales community, including the men. What you’re doing could impact others in a tremendous way.

Where to start

Organizations can begin by prioritizing women in management and leadership roles.

Barbara is quick to point out this doesn’t mean giving them jobs.

Organizations should choose women who are good at their jobs. Look for talented women and nurture their careers.

Additionally, women need to acknowledge their desires to progress in their careers. Instead of assuming that people will notice your success and consider you for promotion, let your leaders know where your interests lie.

When positions open, the hiring parties likely already have candidates in mind. Let your leadership know that you’d like to be considered for other positions.

Volunteer for special projects. Familiarize yourself with departments outside of your own. If you recognize a recurring problem, ask if you can put together a team to seek solutions to the problem.

If you’re a leader with female employees who want to advance, include them in special projects and encourage them to volunteer for things.

Employees in every organization have a responsibility to ensure its health and success.

“Standing Out As Women In Sales” resources

Connect with Barbara on Twitter @barbaragiamanco.

Find her on LinkedIn, and connect with her blog at You can also find her on the Women in Sales Hub.

Call her at (404) 647-4925, because she’s still a big fan of the telephone.

You can find her podcasts on iTunes, Stitcher, Google Play, and multiple other platforms.

There’s a reason I continue suggesting the book, Stop Selling & Start Leading: How to Make Extraordinary Sales Happenfrom our sponsors at Wiley. It’s a fantastic blueprint of all the things buyers say they expect from sellers and want from sellers.

I’m so convinced of its message that I’m offering a free excerpt of the book so you can check it out.

Leave us a review wherever you consume this content and share it with someone else who might benefit from our message. If you haven’t already done so, subscribe to the podcast so you won’t miss a single episode.

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