Having a great mentor can go a long way, in every hero's journey the mentor has played a key moment for them. Do you think without Obi Wan, Luke Skywalker would have been able to defeat his father Darth Vader aka James Earl Jones? Do you think without Mufasa (also played by James Earl Jones), Simba would be able to grow up to defeat Scar? All I’m saying without James Earl Jones mentoring our most famous heroes would they be successful? I don’t believe so. With the same concept Sales Reps are on their own path and with the right guidance they can be more than just a rep, they can be something far greater.

totes mcgotes

When I was young, or at least younger than I am now (tempus fugit and whatnot), there were few things I wanted to do more than play basketball. I’d meet friends down at the park for pick-up games, I’d always pine for it in gym class, and I had NBA Jam down to a science. There was one small issue in my love affair with basketball: I could never get the ball in the hoop.

I would try everything. Mimicking foot placement of the more athletic kids. Emulating the hand motion of every professional, from Jordan to Malone. I even thought strength might have been an issue, and in lieu of a weight room, I went into my parents’ garage and started curling a pair of unused paint buckets. None of these helped, but during a mishap in the latter, I did cover my pants in a color Sherwin Williams calls “Nifty Turquoise.”

Be like mike

I was thinking back on this green-blue memory recently, and it finally hit me. I was making the problem much more complicated than it actually was. It wasn’t the fact that my stance was to far apart, that I never followed through on shots, or that the diameter of my biceps was just slightly smaller than a sample can of Nifty Turquoise. The issue, in and of itself, was just that I wasn’t good.

This may sound like an oversimplification, and it certainly is. But think about it. Was my stance off? Was my shot weak? Was my bench press even weaker? Yes, yes, and yes. But collectively, these just equal someone who isn’t very good at basketball.

I don’t tell you that story because I have a kink for public humiliation. I bring it up because it is so applicable to many sales reps.

On fire

Many managers look at a sales rep with underwhelming or failing numbers and will almost always try to pinpoint a precise issue. Are they not prospecting efficiently? Do they have a surplus of prospects but fail to convert them? Maybe they get caught off guard when they have to deviate from their normal sales pitch?

Again, the answers are almost always yes, yes, and yes. More often than not, sales reps fail because they simply aren’t good at sales.

This is not meant to sound disparaging towards reps who are far behind their quotas. And it is certainly not meant to give managers the impression that all hope is lost. There is one striking difference between a struggling member of your team and nine-year-old me, tossing up threes like I was scared of the ball might hurt the net.

That difference?


Sales managers are no different than a basketball coach. They need to tailor strategy to best match the talents of their team, and they also need to train “players” on how to improve, and best utilize these talents.

Below, we have developed three drills to help develop the talents of struggling reps so that they can take you to the finals (in this metaphor, “the finals” is simply just not sucking at sales).


Before any athlete can take the court, they need to know their fundamentals. You can’t dunk if you can’t jump. You can’t toss an alley oop if you can’t pass. And you can’t follow up with clients if you have know idea where you put their phone number.

Organization for sales staff is more than just keeping track of price sheets and having a mail client that auto-files emails. It’s the whole sales process, from prospecting, all the way down the pipeline.

Often times, your reps already have their own process in place, but they can get bogged down by stale leads they don’t want to let go of, they have improperly prioritized tasks/goals, or the process they have in place is simply too chaotic. In this situation, all that may be needed is a quick, hands-on session with them. Take a look at their procedures, and help them flush out the gunk that is preventing flow through their pipeline. In fact, this is a useful meeting to have with all your sales staff from time to time.Organized

That’s the best case scenario. People aren’t born with an innate sense of organization, it has to be learned. The good news is that this person must have some demonstrable skills or talents, or else you wouldn’t have hired them. Lay out a set of best practices, or even more specific process, and continue to coach your rep to adhere to these.

A simple approach many managers have found effective is to take larger goals that have been given to reps and break them down into smaller, more manageable, short-term goals.

A common example of this is taking monthly quotas and simply dividing them into a series of weekly goals. This may seem redundant, but some people have a fundamental issue with large goals and find it easier to set their sights on something near and attainable.

As my favorite author, Douglas Adams once said “I love deadlines. I love the whooshing sound they make as they fly by.” If you are able to make goals simply appear more attainable, reps will be much more likely to tackle them instead of watching them whiz by their head.

You will be shocked by how much a bit of structure can help less-than-stellar reps.


Can you blame a player for not setting up a pick because he thought the play needed him swing outside? Yes. Yes, you can. This may or may not have been why I never went back to pick-up games at my childhood park. However, what an effective coach would do is sit a player down and review the playbook with them.Lets go-1

Obviously teaching your sales staff how to run a four corner offense won’t do much to increase their sales (unless you are selling basketball playbooks, I suppose.) What you can, and should, do is make sure all your reps, especially the ones falling short on quotas, have a full and thorough understanding of the services they’re selling. Are they focusing their pitch on secondary services? Have they lost sight of selling propositions? Do they keep showing up to work in jeans covered in an oddly specific shade of teal paint? These are all issues that can be addressed by simply realigning the value your rep has on your product with that of customers (and a new pair of pants).


You knew it was coming, didn’t you? There was no way we were going to set up an elaborate basketball/sales metaphor and not mention teamwork. While it may seem like a bit of a platitude, teamwork really is the single greatest asset to developing and maintaining a quality salesforce.

We all know that when your team operates as a single, cohesive unit, productivity increases and sales follow. It’s basic management. What can be overlooked in this regard is how to actually go about this.

The strongest assets in any department of any company, and especially in sales, are the seasoned employees. The wiley veterans who have seen it all.


The absolute best way to help a struggling sales rep is to pair him with a senior co-worker. Sitting them down and working out organizational processes and effective communication is one thing, but at a certain point you need to let them get their hands dirty with one of your company’s best. Some of us just simply have a hard time grasping concepts until we are in a game-time situation, and working in conjunction with a seasoned pro will have two immediate benefits.

First, they’ll be able to watch and observe how the vet operates. They’ll learn techniques, tricks, and attitudes that may not be covered in your company’s practices but are necessary nonetheless.

Second, the more experienced of the two will be able to compensate for the others shortcomings in real time. Are they being too pushy, maybe not selling value hard enough? They’ll be receiving instinatious adjustments which will stick with them more than any funnel diagram ever could.

Post-Game Highlights

To summarize, sales managers often focus on one specific area of sales to assist their struggling reps. Instead, focus should be placed on coaching your team in fundamental drills that they can build off of themselves.

Despite my relentless practice and love of the sport, I never did get great at it. When high school came around, I decided I might be better suited for cross-country running. Wouldn’t you know it….I wasn’t good at this either. The difference this time, however, was that I was on a team with an actual couch. Our couch worked with me day in and day out, drilling fundamentals and more advanced techniques into my psyche. By my Senior year, I was MVP of the team and courting scholarship offers. The talent was there, and like your sales team, I just needed someone to teach me how to use it.

Posted by Rishi Mathur
Rishi Mathur
Rishi Mathur is the Content Producer for LeadIQ and is one of the most important voices for this generation. Rishi has on many occasions been compared to the likes of Aziz Ansari and Gandhi based solely on his looks. He has helped with the growth of several different startups and has experience in both marketing and sales. He has been published in many major media outlets such as TealMango, India.com, The Oregonian, and Highland Park Planet. He is a champion at building communities and would love to start his own cult worshipping the different cuisines around the world.

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