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Shelley Lavery is the CRO and Co-Founder of Jiminny, the leading conversation and revenue intelligence platform that helps companies maximize their revenue. With over a decade of experience coaching B2B sales teams, Shelley was previously Group SVP of Sales at Reward Gateway now spearheads the sales performance discussion with expertise and insight.

How to Get Started Coaching Your Sales Team

As someone who’s spent years in the thick of sales trenches, I can tell you firsthand that coaching a sales team is both an art and a science. It’s one of those things that can make or break your success as a sales leader. I’ve learned a lot over the years, and want to share some practical tips that can help you get started with coaching your own sales team.

What Sales Coaching Really Is

Before we dive in, let’s clear up what we mean by sales coaching. Think of it less as teaching or training and more as guiding. It’s about asking the right questions, providing feedback, and helping your team think critically about their approach. The goal isn’t to give them all the answers but to help them discover those answers on their own.

And, just like top athletes have coaches to help them fine-tune their performance, even your most seasoned reps can benefit from a little guidance. That’s why sales coaching isn’t just for the newbies. It’s for everyone.

The Benefits You Can’t Ignore

If you’re on the fence about investing time in coaching, let me tell you—it’s worth it. Regular coaching can lead to improved win rates, shorter sales cycles, and better overall team performance. But it’s not just about the numbers. When done right, coaching boosts rep confidence, job satisfaction, and even reduces turnover. That’s a win-win for everyone.

How to Get Started: Prioritise and Personalise

Here’s where things get interesting. You might be thinking, “I don’t have time to coach all day, every day.” And you’re right—coaching can’t take up your whole schedule. But it doesn’t need to. What’s crucial is prioritizing where and how you coach. Start by taking a close look at your team’s current performance. Where are the gaps? Which skills need the most work? Align this with your market’s demands and zero in on the areas that will make the biggest impact for your team.

And remember, sales is all about people. Get to know your team members as individuals—their strengths, weaknesses, aspirations. Tailor your coaching to their specific needs, and you’ll see them flourish.

Asking Powerful Questions

One of the biggest lessons I’ve learned over the years is that you don’t need to spoon-feed your team. Encourage them to think independently by asking open-ended questions. Instead of telling them what to do, guide them to figure it out themselves. This not only helps them grow but also builds their confidence and autonomy. Trust me, when they start owning their processes, you’ll see the difference in their performance.

Creating a Coaching Culture

Let’s talk about culture. One thing I’ve seen transform teams is making coaching a regular activity—not just something you do when there’s a problem. When coaching becomes part of the routine, it takes the pressure off you as the leader and makes it a collective responsibility. Everyone starts to take ownership of their development, and that’s when the magic happens.

Start by setting clear goals for your coaching culture. What do you want to achieve? Then, choose the right coaching formats—whether it’s manager-led sessions, peer coaching, or self-coaching. Get everyone on board, and make sure they understand the benefits. You’ll be surprised at how quickly people buy in when they see what’s in it for them.

Ownership: The Secret Sauce

If there’s one thing I’ve learned that’s crucial in coaching, it’s this: Ownership. When your reps feel like they own their development and outcomes, their motivation goes through the roof. Let them take the lead in their coaching sessions, set their own goals, and decide where they need help. This sense of ownership fosters accountability and makes them more invested in their success.

Keeping It Simple (and Fun!)

Don’t overcomplicate things. Focus your feedback on one or two areas at a time, and keep it actionable. And hey, coaching doesn’t have to be all business. Make it fun! Use gamification, run friendly competitions, and celebrate wins—no matter how small. Trust me, a little bit of fun can go a long way in keeping your team engaged and motivated.

Measure, Track, and Adjust

Finally, you’ve got to measure your coaching efforts. Look at key metrics like adherence to methodologies, conversion rates, deal sizes, and sales cycle lengths. Keep an eye on trends and adjust your approach as needed. Coaching is an ongoing process, and what works today might need tweaking tomorrow, which is why tools like conversation intelligence platforms are business-critical when it comes to sales performance tracking.

Wrapping Up

Coaching your sales team might seem daunting at first, but with the right approach, it’s one of the most rewarding things you can do as a revenue leader. Prioritize your efforts, foster a culture of ownership, and keep things simple and fun. Before you know it, you’ll see your team—and your results—soar.

I hope these insights help you get started on your coaching journey. Remember, coaching isn’t just about improving sales—it’s about empowering your team to reach their full potential. And that, in my book, is what great leadership is all about.

You can find more of my guides and advice on sales coaching over on the Jiminny blog.