Your sales team member is struggling with closing techniques. How can you guide them to improve effectively?

First of all, I focus on observation—listening to call recordings to identify where the gaps are. I also like to use preliminary metrics to pinpoint exactly where we lost the deal. Based on the gaps, I suggest a solution and format. This could be 1:1 coaching, role play, or a micro-learning session. The third step is to evaluate. I listen to the calls again and assess improvements based on key parameters.

Role plays could bring out gaps in skill sets which can be addressed with specific training around the same. Challenges in closing could also be a lack of proper understanding of the potential customer's needs and pain points in a rush to pitch and close. Asking is usually 10x more powerful than saying. Questioning skills and relationship building too go hand in hand which makes closing easier.

If sales person has knowledge, capabilities and is effectively closing every interaction with the customer there is very high chance they are effective in closing sales when working on a sales opportunity as well. Thus, you don't have to wait for that perfect moment in opportunity to assess sales person's closing skills, you can do it by "shadowing" and observing her/him in almost any customer interaction. All you need to do is have preparation and alignment conversation with sales before the customer interaction to clarify meeting focus, desired outcome, agenda, differentiating insight. Have a check list for noting observations during meeting. Have post-meeting feedback conversation.

Assuming we understand the techniques, and the actual struggle is when and how to use the closing techniques. Three things to start with: 1 - Role play with peers (other sales reps). Sales manager should setup and mediate the situation. If you can do this effectively with your peers, customers will be a breeze. 2 - Ensure the closing techniques will be authentic for the rep using them. Very literal closes are just that and will hurt you more than help you. 3 - Spend more time in the qualifying stage so later your client wants to buy from you because you have something they need. If you get an objection in a close you most likely missed something in your qualifying techniques.

Observe their interactions with potential clients. This involves more than just listening to their conversations. Pay attention to their body language, tone of voice, and the way they handle objections. Are they closing too soon or too late? Are they addressing the client's concerns effectively? These observations will provide valuable insights into their strengths and weaknesses. Identify specific areas for improvement. Once you've pinpointed their challenges, you can tailor your coaching to address them directly. For example, if they struggle with handling objections, you can provide them with specific techniques and strategies.

Start by giving targeted training on closing techniques like assumptive or urgency-based closes. Include role-playing to practice real-life scenarios and handle objections better. Offer actionable feedback from actual sales calls. Encourage them to tailor solutions to each client's needs, showing how the product directly solves their problems. Build their confidence with solid product knowledge and stronger client relationships.

Role play and close some deals with them as well. There's nothing better than hands-on coaching. We cannot rely solely on software to teach the basics, but we have to find their comfort zones and break them out of them. Hit them with every objection in the book and see how they handle the pressure. Then guide them to solution-based communication.

Create realistic scenarios. The more authentic the role-playing scenarios, the better they will prepare your team member for real-world interactions. Consider using past sales calls as a basis for your role-plays. Provide constructive feedback. After each role-play, offer specific and actionable feedback. Avoid generic comments like "you did great." Instead, point out specific areas where they excelled and where they could improve. For example, you might say, "Your response to the price objection was strong, but you could have emphasized the value proposition more."

Confidence is a top skill in sales. To help your team member believe in their ability to close, try these two strategies: Celebrate past wins: Remind them of specific deals they’ve closed and what strengths they brought to the table. Highlighting their successes boosts self-belief and motivates them to repeat that success. Role-play scenarios: Practice different closing techniques and objections together. The more they rehearse in a low-pressure setting, the more natural and confident they’ll feel when the real deal comes along.

A series of missed/ failed closings can bruise one’s confidence and throw oneself out of momentum. I would encourage the member to start small, look for easy closings either with trending products, or warm networks eg families and friends. A few done deals will build the momentum and confidence to go for more challenging and bigger ones.

Confidence isn’t built overnight—it’s sculpted through small wins and positive reinforcement. Help them develop a mindset that sees a ‘no’ as a step closer to a ‘yes.’ Celebrate the process, not just the outcome. Share your own war stories—the deals you almost lost but pulled through with grit and persistence. Realize that for many salespeople, it’s not a lack of skill but a lack of belief in their ability that holds them back. Equip them with techniques to manage nerves, such as visualization or power posing before a call.

The best closers aren’t the best talkers—they’re the best listeners. Analyze the pitch together. Is it too long? Too technical? Too pushy? Encourage them to listen more than they speak. Use frameworks like SPIN or the Challenger Sale to craft pitches that are more about solving a problem than making a sale. Refinement is not a one-time activity; it’s an ongoing process of tweaking, testing, and adapting based on what resonates most with clients. Challenge them to cut the jargon and speak in plain language that hits home.

Keep the momentum going with regular check-ins and progress tracking. This isn’t about micromanaging; it’s about setting the cadence for continuous growth. Set specific, actionable goals—like converting a certain percentage of warm leads or improving follow-up techniques. Use a mix of metrics, feedback from peers, and self-assessments to keep them aware of their growth areas. Let them own the process by asking, “What do you feel you did best this week?” and “Where do you see room for improvement?”

Ensure your sales team members know and feel that you care for them. If you genuinely care for them, they will always know you are there for them. Propose a routine/operating rhythm for coaching with new sales person, that is general, only as a starting point and as your relationship grows, shape routine to your relationship, sales persons' preferences, sales persons' and organization's objectives. Different people, different situations expect different approaches and different support. You may need to be flexible some times. ;) Coaching cannot be forced.