How to Coach Rookie Sales Reps: 4 Tips

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Conner Burt
Conner Burt



Lionel Messi didn’t become the FIFA World Player of the Year four times by kicking a ball around blindly. He had guidance. There’s no doubt that the world player had talent. He originally caught the eye of FC Barcelona as a 13 year-old by sending a video of himself juggling a tennis ball (113 times in a row) and an orange (120 times in a row).

Nice moves, Messi.

To groom top performing sales folks, you’ll need to take risks on young reps who show a similar kind of raw talent. But to hone that talent and turn it into sales expertise, coaching is required.

How do you coach brand new sales reps to bring out their maximum potential? Follow these four steps. 

1) Understand Their Individual Motivation

Contrary to popular belief, many young reps aren't solely motivated by commission checks. Maybe it’s the generation, but most young reps we hire have something else that keeps them going.

For example, Messi liked sweets. Here's an account of Messi's motivating sweet tooth from the New York Times:

“One of his early youth coaches in Rosario, a man named Carlos Marconi, discovered that Messi enjoyed alfajores, a kind of chocolate cookie. According to an TV interview with Marconi, they struck a deal: a cookie for each goal. The trouble was that Messi routinely scored four or five goals a game for his club, and so, to motivate him, Marconi had to make it harder. To push him, Marconi announced a new regime: two alfajores for every goal Messi scored with his head. The next game, Messi dribbled through the entire opposing team, including the goalkeeper, then stopped at the goal line to flick the ball up into the air with his foot so that he could head it into the empty net. When he found Marconi’s eye in the stands, Messi smiled and held up two fingers.”

To find your new sales rep's “chocolate cookie,” you need to first earn the right. Invest in young reps personally, so that they feel comfortable opening up to you.

Once you build some rapport, here are a few tactics that can help you tailor sales plans for each individual:

  • Vision statements: I first saw a vision statement in college as a soccer player, when our head coach explained their importance during the first week of each season. Subsequently, my first sales coach did the same thing. Not a coincidence. We’ve incorporated vision statements into our sales process at and have seen the dividends. 
  • Personality tests: We like the Predictive Index, and while it’s not a tarot card, it helps give managers insight into each rep. Other tests to consider are DISC and Strengths Finder.
  • Unstructured and unscheduled meetings: Meet with reps on their turf. Whether they like to have a beer, go for a run, take a walk, or sip coffee, simply ask them how things are going and what gets them up in the morning in an unstructured, unscheduled forum.

2) Establish a Training Cadence Based on Feedback and Observation

Once you understand your new rep's motivation, it’s best to set up a cadence for coaching and training. Here’s what we’ve found is a great recipe:

  1. Weekly, 30-minute one-on-ones with managers: Spend a third of the meeting on your rep's agenda, a third on reviewing the past week, and a third on looking ahead.
  2. Weekly team training lesson: Cover a topic that often comes up in one-on-ones. It could be about competitors, pricing, objection handling, or process. Create a short and sweet assignment of sorts that reps can complete on their own time.
  3. Bi-weekly observation or practice session: Once every two weeks, managers should get in the weeds. Instead of telling people what to do, practice it with them, or better yet, participate with them. Go to meetings or make calls alongside your reps, and provide tips along the way.
  4. Monthly vision statement review: We prefer to occasionally review the vision statement with someone new on the team, or to revisit for accountability purposes.

With this structure in place, young reps will feel they're being invested in and have every opportunity to ask questions, seek guidance, and feel fulfilled as they grow.

3) Manage Confidence

We onboard bright, decorated young folks who’ve had a lot of success in the past. As you manage young reps, your biggest challenge and opportunity will be to manage their confidence. Especially when things don’t go their way (missed goals, rejection, etc.).

You should match your confidence coaching plan to your culture, but we find that a few things help: 

  • Framing: When we talk about competitors, we focus on our strengths first, not theirs. When we review metrics we focus on the good first, then the areas of improvement. 
  • Make it fun: When we win a deal against a competitor we notch a baseball bat; when we schedule a demo, we write it on the chalkboard; when someone leaves a great voicemail, we give them a high five. 
  • Controllables and 1% improvements: Nothing kills confidence like a missed goal. While goals are important, we focus more on controllables (calls, prospects added into the pipeline, demos completed) and convey that we know things won’t change overnight. Instead, we keep the focus on marginal gains that add up (1% at a time).

4) Teach the Hard Stuff through Repetition and Questions

As you well know, sales isn't easy. Young reps who aren't used to scraping their knees need some guidance on how to handle tough situations. 

Here are some examples of tough sales situations and how to coach proper reactions:

  • Letting a deal go: Make sure your reps know the difference between persistence and knowing when to let go. Never let your reps give up in the pursuit of prospecting. The more they do, they better they will be at qualifying. Do teach your reps to let go of a prospect who truly isn’t a fit for the product. There’s a fine line between persistence and pushiness. Teach it. 
  • Saying no: With a clearly defined ideal client profile, you should be able to coach young reps on when to say no. List out the common questions that tend to be showstoppers or red flags, and coach reps on when and why to say no. We find that being honest, in the end, is appreciated and ultimately wins us more deals.
  • Understanding decision makers and influencers: Young reps are especially prone to happy ears. For example: “I just did a demo with Company X, and they loved it! I think we’ll have them on board next week.” As a sales manager, you should temper their expectations and help them identify and engage the decision maker. Ask: What's the next step? Is there a compelling event driving them to a decision next week? Who -- outside of your contact -- will be involved in the decision? This teaches young reps to find the answers to these questions with their prospects before you even ask them.

If you’re a sales manager and you heed this advice, share your results! What little things do you do to keep your team motivated? Do have more concise coaching methods? If you’re a young rep reading this, tell me about your coach, and how they’ve helped you. 

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Topics: Sales Coaching

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