Sales team hiring: How to handle underdogs

Ten years ago, I hired a salesperson with incredible drive. He had recently lost everything—his job, his house, all his money. But he was hungry to get back in the game and work his ass off. He was under-qualified, but what he lacked in experience, he made up for in energy. So I took a chance on him.

I spent an excessive amount of time trying to train him, because I desperately wanted to be right about him. I worked nights and weekends with him. I coached him to nail down his sales pitch and aggressively pursue leads. But a year later, we weren’t seeing any improvement. He just didn’t have hustle—that killer instinct you need in sales.

I ended up wasting my own time and my new employee's time, just trying to get him to be good enough. By the time I let him go, not only was he out of a job, but he had just wasted a year trying to fit a role that wasn’t right for him.

He was one of many hiring mistakes I’ve made. And while I still believe in hiring based on attitude and not just experience, I’ve realized that risky hires need to be carefully and systematically managed to ensure they become successful.

Jack Welch’s hiring quadrant

The best sales hiring exercise I ever learned came from the infamous Jack Welch, former sales manager and CEO of General Electric. His classification system for employee archetypes has helped me better understand how to work with different kinds of people.


According to Jack Welch, every hire scales somewhere on the chart above in terms of capability (x-axis) and willingness (y-axis). Here’s how I’ve broken up these different archetypes:

  • Capable and willing: I call these employees the rockstars. They’re both great at their jobs, and excellent culture fits. Rockstars work hard to cooperate with other team members, and their sales skills are spectacular.
  • Capable and unwilling: These are the assholes. These are the employees that have an outstanding resume, close lots of deals, but are just nasty to work with. Assholes will sabotage your company culture and will end up destroying your team—if not your whole company—from within.
  • Incapable and unwilling: The misfits are neither qualified, nor do they have extra zeal to make up for it. Similar to the rockstars, the misfits are super easy for hiring managers to spot.
  • Incapable and willing: The underdogs are my personal kryptonite. These are the employees that have the heart, but don't yet have the skills. They're hard workers and have the highest growth potential in the company.

While most managers run straight to the rockstars, the best hires usually end up being the underdogs. The underdogs are enthusiastic learners, eager to absorb the ins and outs of the business. Coming in as rookies, they often have the greatest growth potential because while anyone can learn sales skills, no one else can learn the underdog’s hunger.

But underdogs present the toughest hiring decisions, because you have to bet on whether they have what it takes to catch up to the rest of the team. As a result, you need to walk a fine line between giving them a chance to meet their potential and knowing when it’s time to cut your losses and part ways.

How to work with underdogs

Underdogs are such tempting hires because they are often greatly undervalued candidates. They’re not applying for the job to work for a few years and then move on. They are looking for a growth opportunity to kick-start their career, so whoever offers them that opportunity will earn their allegiance and undivided attention.

But not every underdog is a success story. Sales requires a grit and hustle that they might not have. The trick in dealing with underdogs is knowing when to call it quits, since the more time and money you invest, the more emotionally invested you become, and the more difficult it will be for you to make a rational and objective decision when to call it quits.


By setting up a bullet-proof system for evaluating the performance of a new hire, you’ll accomplish three things:

  1. Weed out underperformers by setting your expectations in stone.
  2. Enable those who have what it takes to succeed by holding them to high standards.
  3. Set the same expectations for all your sales reps.

Gauging your expectations will help your underdog achieve top results and succeed within your company. Here are four questions to ask yourself when preparing to hire them.

1. Does the underdog walk the walk?

Due to the psychological concept of illusory superiority, most people overestimate their capabilities. For example, in one survey of Stanford MBA students, 87% of the student body claimed that their academic performance was above average.

Likewise, people tend to exaggerate their work ethic. They think, “Well, I could be hardworking if I wanted to be.” So some applicants will fool managers into thinking they’re underdogs when they’re actually just cleverly-disguised misfits.

Since their performance won't be up to par yet, pay particular attention to how new hires spend their time to see if they’re as hungry as they claim:

  • Check to see if they are eagerly taking notes and learning the processes
  • Get feedback from their peers to see how well they’re absorbing new information
  • Ask for concerns from the hires themselves to get a sense of how motivated they are to improve

You hired the underdog because you thought they’d dig deep and give you their all. If their work ethic is anything less than excellent during onboarding, think about how they’ll act in six months. Cut your losses quickly if you were duped in the interview process by an undercover misfit.

2. How long are you prepared to wait for them to catch up?

In just the US and UK, companies spend about $37 billion dollars annually to keep on unproductive employees who do not understand their jobs. To stop yourself from falling into this trap, set a time limit before you hire the underdog in the first place.

You’ll need more time than you think. Sales managers drastically underestimate how long it should take someone to get the hang of the processes. Training a new sales rep typically takes 7 months, but over 27% of employers judge the success of an entry-level employee in just two weeks.

So I recommend that you decide how much time you think catch-up should take for someone with no sales background, and double it. Setting time expectations before hiring the candidate lets you know when to cut your losses should his passion and work ethic not make up for his lack of experience.

3. How will you onboard this hire?

Training a new sales rep is a time-consuming process, so it might be your first instinct to let the underdog have at it himself. But studies have shown that 40% of employees who receive poor training leave their jobs within a year. You hired the underdog because you thought he had the right zeal for success. The last thing you want to do is set him up for failure.

Underdogs will require more attention than more qualified hires to succeed. That means that the training responsibility falls entirely on you, as the manager. Since underdogs have the greatest growth potential in the company, you want to make sure you equip them to meet their full potential, and be the stars of your workforce.

You can do this by having a metrics-based training program set in stone:

  • Measure performance through things like time to close a sale, or amount of emails that resulted in a qualified lead.
  • Use these metrics to pinpoint their strengths and weaknesses, and work with them on improving them.
  • Delegate some training responsibilities to more experienced staff members to improve team dynamic.

To see whether your training program is working, have a weekly 1:1 with the new hire yourself. This way you can see first-hand whether any progress has been made.

4. How will you measure success?

Being data-driven is a surefire way to stop yourself from making excuses for the sympathetic underdogs. So make sure that your final evaluation of their performance is quantitative and not qualitative.

Too many managers set expectations either unreasonably high (equivalent to their top performers), or unreasonably low (because they’re newbies). The ultimate benchmark should be equal to the average performance among your sales reps.

This benchmark is the minimum performance expectation—anything below, will indicate that the employee wasn’t worth the investment. You are not hiring an underdog because you want an employee with a free pass— you’re hiring an underdog because his hunger and energy gave you the impression he was capable of not just catching up, but excelling.

So, if doubling the amount of time you anticipated isn’t enough for the underdogs to meet your standards, then you'll know that it’s time to let them go.

Turn your underdogs into rockstars

Keep in mind that every rockstar employee once started out as an underdog. While an underdog requires more training and work than other applicants, should they persevere, their allegiance and passion will make them some of the best employees you’ve ever worked with.

What sets underdogs apart from other hires is their contagious passion. They are so energized by their ambitions that they will stop at nothing until they’ve reached their goals. And while most sales skills can be taught, this superb attitude cannot.

If you catch these gems early, you’ll find that the underdogs can have a spectacular, long-lasting impact, both on overall sales performance and on the team dynamic—making them well-worth the risk and the investment.

Recommended reading:

The ultimate sales hiring guide for B2B startup founders!

This is the ultimate sales hiring guide for startup founders. Learn when to hire salespeople, who to hire and how to manage them at every stage of your sales process.

My startup hiring interview hack: Why? Why? Why?

Interview hack: Why? Why? Why? This is a simple strategy to x-ray through the bullshit answers applicants give you and get real insights into what makes them tick.

The sales rep onboarding hack

Want to accelerate your sales ramp up, train new reps in less time? Here's a scalable strategy for onboarding new sales hires.

Table of Contents
Share this article