5 Potential Pitfalls for a Sales Leader

5 Potential Pitfalls for a Sales Leader

A few weeks ago, our Chief Sales Officer, Justin Fite, sat down with the folks at SalesHacker for a webinar entitled, 3 Keys to Winning as a High-Growth Sales Org. In the session, Fite discusses some of the lessons, pitfalls, and key ideas he’s gleaned from over 20 years of sales experience. If you couldn’t be there, this blog series will catch you up. Here’s part two of three!

5 pitfalls of a sales leader

Justin Fite, Lessonly’s Chief Sales Officer, has made more than a few mistakes over his 20+ years in sales. And with a little reflection, he noticed five recurring themes in his career that have caused him or his team to stumble. He’s lived these five pitfalls personally, and watched sales teams and organizations decrease in productivity and performance as a result. But by learning from those mistakes, and avoiding the following five misconceptions, a new generation of salespeople can improve their own sales leadership.

Everyone thinks like me

As a new sales rep and manager, it was easy for Fite to believe that everyone thought just like he did. But Fite quickly recognized that telling a prospect what he would want to hear wasn’t a good strategy; he had to put himself in their shoes. “Realizing that your reps and customers will combat the problem very differently than you is really critical to keep in mind,” he notes. Understanding people is at the heart of every great salesperson—it helps them be consultative rather than prescriptive. The more that sales leaders understand the hearts and needs of people, the more effective and successful they will be.

Magic Bullet Syndrome

It’s easy to think that one new tool, huge deal, or changed process will solve every problem. However, in a multifaceted sales org, that’s almost never true. The biggest deal, most functional tool, or most effective process is helpful, but it won’t fix everything. There will always be a new problem tomorrow. Fite agrees, “These are complex organizations, and growing is a very complex process. So it’s easy to fall into thinking that one thing will solve the problem.”

When working in a high-growth sales org, recognize that hard problems often require hard solutions. Don’t stop with the easy answer—keep pressing for a more thorough solution.


“It is very easy to have 14 great ideas, try to get 14 things going, and have none of them work.” Prioritization is an essential skill for every sales leader to learn, and in fast-paced organizations, it’s worth considering the side-effects of adopting a new tool or process. Fite notes, “Managers and leaders of small organizations can create a lot of chaos and just overwhelm people.” So he suggests a healthy realism about change and new ideas. Don’t change too many things at the same time. Rather, consider how each change affects reps—as well as the entire sales process. Commit to the few key changes that will have the most impact, and concentrate on extracting as much value from those changes as possible. Your team will thank you.

“Don’t change too many things at the same time. I know that’s easy to say and very hard to do.” – Justin Fite


Fite’s mentors and managers helped him avoid significant pitfalls throughout his career. Andy Kofoid, COO at ExactTarget (now Salesforce Marketing Cloud), reminded him not to under-hire in a sales organization. Fite agrees, noting, “Sales models are built on the fact that you’re going to add people to the organization who are productive and carry quota. You fall two quarters behind your hiring, and there’s almost no way to catch up.” This isn’t just a function of recruiting great people—onboarding twice as many people as planned will take a toll on overall team productivity. Planning ahead with steady hiring will keep a sales org on consistent path to growth.

Trying to slow down

Fite concludes with a basic mantra: “We simply can’t slow down.” Looking across the competitive landscape and the pace of market evolution, sales orgs can’t afford to slow their pace of hiring, innovation, and goal-setting. While in the past, changes in sales strategy might’ve been rolled out every 90 days, Fite says that’s now monolithic. To build a culture of continuous rapid improvement, sales leaders must spend their time and effort discovering processes, models, and systems that streamline productivity for their teams. To see truly transformative results, rather than simply adding salespeople to the team and expecting growth, find ways to multiply the impact of each employee. These combined improvements will result in exponential success.

Failures are an important part of any great career, and these five pitfalls have helped shape Fite into the sales leader he is today. If you missed it, check out part one of this series to read the top five lessons Justin learned throughout his career. Check back next week to read part three, where Fite will share three keys for building a high-growth sales organization—ideas which Lessonly puts into practice every day!

Lessonly helps sales teams avoid pitfalls through great training

Hopefully Fite’s experiences over 20 years of building sales organizations and mentoring sales professionals help you avoid some pitfalls of your own. Lessonly is online training software that helps sales teams learn, practice, and perform in a high-growth, high-pressure industry. Want to see if Lessonly could be the perfect tool for your team? Take a tour.

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