empty conference room

How to Bring Your Sales Management into the 21st Century

Before jumping into best practices for ensuring that you’re effectively managing reps to hit the ground running, opposed to stumbling, I want to start with a definition.

Employee (noun): a person working for another person or a business firm for pay.

Now, the word, “Employee,” comes from the French word, “Employé,” and dates back to 1825 – 1835; almost two-hundreds years ago. I start with this because if you’re someone, especially a manager, director or VP, who brings this two-hundred year old definition into the interview room when looking for your next Sales stars, you’re doomed. If the relationship between your organization and its “employees” is purely transactional (do work → get money), they will eventually resent you, underperform and leave. This is because today’s 21st century employee, especially in Sales, need a lot more than a salary or commission to grow and thrive with your organization.

Below are five strategies to bring your sales management into the 21st century:

Conduct (meaningful) one-on-ones

The surest way to know if your one-on-ones are meaningful and effective is to ask yourself and your reps (anonymously, of course) how helpful one-on-ones actually are. In many organizations, most say they’re the worst part of their week, others say they’re just another task to get through, and few look forward to them.

A good one-on-one is where the reps feels completely comfortable articulating their wins, lows, and frustrations to their managers. It’s where no one is watching the clock (too often) and managers are listening more than they’re speaking; where they’re asking questions like “What could be going better?,” “How can I improve?” “If you were in my position, what’s the first thing you would change?”

These are the hard questions. And, they’re hard because you, as a manager, are making yourself vulnerable to someone who you’re supposed to lead, have answers for and sometimes discipline. While this may be uncomfortable, it will become easier as you do it more and more. And, you’ll be surprised by how much more deeply you connect with your reps.

Note : Notice how the sample questions I provided are open-ended vs. “yes / no.” And, these are just a few of the many that you can ask during one-on-ones to make them better. Here is a list of 101 good ones.  

Hold weekly training sessions

Training’s important, right? But, just how important? Well, important enough that 72% of employees place a higher value on on-the-job training than they do a college degree. Yes, you read correctly. So, if almost three-fourths of your team values training over the college degrees that most likely many of them have, what do you do? You train them often and train them well. The keyword here is well.

In the 21st century where over-stimulation is the norm, attention spans are shorter, and more valuable, than ever. This means that your weekly trainings should be engaging, interactive and informative. Long gone are the days where a manager could get in front of their team for hours on end teaching them invaluable sales tactics.

Now, trainings have to be:

  1. Concise – as long as they need to be, but should aim for 30 – 45 minutes
  2. Interactive – you should be asking your reps questions throughout trainings and  encouraging them to ask questions
  3. Actionable – if reps don’t practice what you’ve just trained them on, they’ll forget it almost immediately. Have them role-play and practice with one another during the training itself, and then reiterate in the following week’s trainings to ensure retention.

Create and communicate Performance Improvement Plans (PiPs)

Every growing Sales organization needs to have a measurement of success that reps can look to in order to assess their own performance. And, if reps aren’t doing well, there needs to be measures in place to formally bring it to their attention (saying “hey, you need to get your numbers up” is useless). If not, you will may end up with a handful of unproductive reps who are wasting precious resources and a spot that someone more competent would gladly fill.

This is where a Performance Improvement Plan (PiP) comes in place. A PiP is a formally communicated (an email) record of a rep’s lack of performance (e.g. you haven’t achieved your goal for the last 4 of 5 months), where the rep needs to be by a specific time (e.g. you must attain at least 75% of your goal by the 21st of November), and what will happen if they don’t (e.g. you will be eligible for termination).

Reward performance unrelated to Sales

If you’ve hired the right reps and are doing your own job well, you will begin to see a handful of non-Sales related activities taking place.

For example:

  • Mentorship: Reps who have been around longer spending time listening to newer reps’ calls and taking time at the end of their days (should be outside of calls hours) to help them practice their pitches, handle objections, etc.
  • Ideation: Regardless of tenure, if there’s the expectation and right environment for it, reps will begin to bring up new, and often very good, ideas in one-on-ones, larger meetings and one-off emails.
  • Self-policing: No Sales team is perfect. Sometimes, people do things that are plain wrong or plain counterintuitive to the goals of your organization. But, instead of having to constantly police your reps, you may see others stepping up and helping others course-correct, making your life, as a manager, much easier.

Those are just a few of the potential behaviors you may see reps start to exhibit. The point is that you, as a manager, need to foster this environment of intangibles and reward reps when you see and hear about them just as you would if they achieved their monthly goal. Without this, your relationship is purely transactional and no one will be motivated to go above and beyond achieve their goal.

Go on team outings that forge bonds, not waste them

Sales teams love happy hours. You know, those things where the music in the bar is too loud to hear the person in front of you. A new (or older) rep will almost certainly imbibe too much and embarrass themselves and people walk away feeling giddy. But not as if they truly formed bonds with their co-workers. Don’t get me wrong, I love happy hours, but they’re more often than not a means of blowing off steam, which is great.

But, in order to have reps forge bonds with one another on an intimate level, which will certainly make them happier at work and more motivated to achieve the overall goal, be creative and find activities that don’t wholly rely on alcohol. This could be anything from hosting a talent show (find out new things about those you work with) to lazer tag (foster collaboration and teamwork) or karaoke (okay, this one will almost certainly require some alcohol, but it’s a fun one).

Salespeople in the 21st century are no longer people “working for another person or a business firm for pay”. Instead, they now require new ways of motivation, leadership and ultimately care (aside from the amount of cash they take home at the end of the month). Money no longer automatically equates to happiness in the workplace. Reps are humans and need management that helps them grow and flourish in your organization. And, the best part is is that what’s normally good for them is also good for you. Win-win.

Mateo Askaripour

Mateo is a Sales Advisor at Skaled and the former Director of Sales Development at Grovo, a rapid-growth NYC tech startup named "One of the Best Places to Work in NYC Tech." He started Grovo’s sales team with CEO Jeff Fernandez in 2013 and streamlined Grovo’s sales hiring, training and professional development practices to effectively scale the team from 1 to 75+ in 2.5 years. Mateo enjoys traveling, reading and writing. To view more of his writings, subscribe here.

You can also find him on Twitter, Instagram or shoot him an email here. He's currently available for consulting.