Let’s Talk this week about a common challenge for businesses: training staff to upsell effectively, without making customers feel pressured or uncomfortable.
Upselling can be a powerful tool to increase revenue and enhance the customer experience, but if done poorly, it risks turning customers away. The key lies in equipping your team with the right skills and mindset to identify genuine customer needs, suggest relevant products or upgrades naturally, and build trust along the way.
Our experts will share practical strategies for SMEs to create training programs that focus on active listening, product knowledge, and empathetic communication. We’ll also explore how to foster a customer-first culture where upselling is seen not as pushing a sale, but as providing valuable solutions that enhance satisfaction.
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Zoe Goodhardt, Partner and Head of Growth and Marketing, TAG
“It all starts with a mindset shift. It’s not about selling more, it’s about understanding better.
“When staff lead with genuine curiosity and ask thoughtful questions about a customer’s goals, challenges or long-term vision, they naturally uncover opportunities to add value. In this context, upselling becomes less about pushing products and more about offering tailored solutions that help the customer succeed.
“Instead of scripted sales lines, train your team to problem-solve. Equip them with intelligent questions that reveal pain points and give them permission to explore ‘why’ and ‘what if’ scenarios with customers. This approach builds trust and makes people feel heard and supported, not sold to.
“When done right, upselling becomes a natural extension of great service. It’s as simple as that.”
Shaun Broughton, Managing Director, APAC at Shopify
“The key is trust and personalisation. Shoppers want to feel understood and not sold to, with 58% considering knowledgeable staff as crucial to a positive in-store experience. But to set teams up for success, SMEs need the right tools to deliver a personalised and efficient service that drives higher-value purchases.
“For instance, a unified commerce system that connects in-store and online operations enables staff to access a real-time view of their stock levels and customer history. With this information at their fingertips, they can be coached to offer tailored, context-aware recommendations that feel like help rather than a hard-sell.
“Training employees to ask questions and build relationships, rather than push products, is also important. Choosing a POS system that allows teams to record specific details about a customer can make this easier. By making data capture seamless and encouraging employees to leverage this information at checkout, upselling becomes less about pushing products and more about being thoughtful.”
Annette Densham, Award Writing Services
“Stop thinking of it as selling. Think of it as telling. Stop thinking pf sales as being ‘pushy’. Think of it as solving a problem.
“Selling is really telling stories, the truth and letting the customer know that you hear them and can help.
“Get rid of the scripts that make your team sound like a robot. Teach your team to be curious, not convincing. Get them asking good questions, actually listening, and having real conversations. Train them to understand the customer’s world before they open their mouth about yours. No pitches or pressure. Selling becomes problem-solving with purpose. Train them to connect and see people, not prospects. The sales will follow.
“Train your team in conversational skills and how to start a chat without sounding awkward, active listening and problem-spotting. Layer in storytelling training so they can share real examples of wins, not rattle off features. Throw in a session on handling objections with curiosity, not defensiveness. Add product/service immersion to get them using, understanding, and believing in what you offer, because nothing replaces confidence built on actually knowing your stuff.”
Christopher Melotti, Founder of Melotti Content Media
“Many SMEs still rely on scripted upselling, but this often feels forced and impersonal. Customers can quickly sense when a conversation shifts into a sales pitch, it activates cortisol, the brain’s stress hormone, which creates discomfort and resistance. People naturally pull back when they feel they are being sold to, especially when it feels out of sync with the conversation.
“A more effective approach is to train staff to engage in natural, two-way conversations. Encourage them to ask about a customer’s typical day and listen with genuine interest. Often, clients mention small frustrations or challenges they have come to accept as normal. These moments are valuable. When team members respond with empathy and offer relevant solutions, it does not feel like selling, it feels like helping.
“The best upselling happens naturally. It’s not about pushing products, it’s about understanding people and offering value when it truly fits. That’s when customers feel heard and are more likely to say yes.
“By focusing on listening and meaningful dialogue, SMEs can empower their teams to upsell in a way that feels authentic and well-received.”
Ebony Parke, Marketing Agency Manager, Outsource2us
“Upselling doesn’t have to feel uncomfortable. When done well, it comes across as good customer service. The key is to shift the focus from selling to solving. Rather than pushing products, staff should be trained to recognise situations where an extra product or service could genuinely improve the customer’s experience.
“It all starts with strong product knowledge and a clear understanding of how different offerings meet different needs. When team members are confident in what they’re recommending and why, they’re better placed to offer helpful suggestions.
“Practical training methods like roleplaying and scenario-based exercises are effective. These build confidence and help upselling become a more natural part of the conversation. It’s not about reciting a script. It’s about learning how to ask thoughtful questions, listen carefully, and respond with options that add real value.
“Sharing real-life examples where upselling has benefited customers can also help. These stories make it easier for staff to see the impact of a well-timed recommendation. When they understand that upselling helps customers make better, more informed decisions, it feels more like service and less like sales.
“Recognition also plays an important role. Celebrate team members who identify genuine upsell opportunities. Encouragement helps build confidence, and confident staff are more likely to deliver a consistent and positive upselling experience.”
Melissa Williams, CEO, Learning Dimensions Network (LDN)
“As business owners, we all want to see our companies thrive, and that involves encouraging our teams to identify and meet customer needs more fully. However, the idea of “upselling” can lead to discomfort for staff and create resistance from customers.
“My experience as CEO, leading a team for over 17 years has taught me that the key lies not in training people to “sell more,” but in cultivating a culture where they genuinely understand and connect with human needs.
“True influence stems from developing a psychologically safe environment where every team member feels valued, heard, and rewarded. When they have a profound sense of belonging and confidence in their own abilities and the quality of your offerings, “upselling” transforms into a natural extension of excellent service.
“They’re more attuned to client needs and proactively offer solutions because they genuinely believe in the value of what they provide. It’s not about training, it’s about empowering your people to be genuine advocates with an approach that organically drives business growth.”
Laura Canham, Business Consultant, Sales Strategist & Keynote Speaker
“The reason most upselling feels pushy? Because the salesperson isn’t listening. One of the most powerful things you can train your team to do is listen more than they talk. When staff focus on truly understanding a customer’s needs instead of jumping into over-explaining or pitching, they gain insight into what the customer actually wants. From there, upselling becomes a natural recommendation, not a forced push.
“Customers don’t want to be sold to – they want to feel seen, heard, and understood. When your staff can reflect that understanding back in the conversation i.e. “based on what you said, I’ve got something else that could also be perfect for you” the entire experience shifts.
“Listening builds trust, softens resistance and leads to better conversions, because the upsell isn’t random, it’s directly linked to something the client has said they want or need.
“Train your team to ask thoughtful questions, pause and pay attention to what’s really being said. When they stop trying to “sell more” and start helping more, the results speak for themselves.”
Katie Reeves, Client Services Director at We are Sprout
“Growing customer value is smart business—it’s sustainable, cost-effective, and builds loyalty. But let’s be honest: asking someone to buy more can feel awkward. So how do SMEs help staff upsell without the ick?
“It starts with redefining sales. Great salespeople aren’t pushy—they’re intuitive experience-makers. They read the moment and elevate it. When customers feel great, they’re more open to exploring more of what you offer.
“But tactics alone aren’t enough. SMEs need culture. As Peter Drucker said, “Culture eats strategy for breakfast.” A strong internal culture sets clear expectations around behaviour and service. When teams understand your brand’s DNA, they can live it authentically.
“The real shift happens when people feel safe to be themselves. Look at retail and hospitality brands that build a mantra around individuality and connection. This empowers staff to engage in real, human ways—making upselling a natural part of great service, not a forced pitch.
“The result? Higher revenue, stronger relationships, and no hard sell required.”
Kunal Joshi, Founder, Bang on Brows
“We don’t view upselling as a sales tactic but rather as an extension of expert care. When beauty professionals take the time to understand each client’s unique needs, upselling becomes a natural, valuable part of the service experience.
“Our approach is grounded in education. Through our Bang On Training brow and lash training academy, we teach beauty industry trainees how to make informed, confident recommendations that genuinely benefit the client.
“Clients trust professionals who care so the best upselling starts with listening. When staff lead with curiosity by asking about goals, preferences, or past experiences, they’re better equipped to provide tailored advice. From there, it’s about communicating as an expert.
“At Bang On Brows, we see upselling as a way to elevate each client’s experience – not just increase sales. It’s about making thoughtful, personalised recommendations that help clients discover services or products they may not have considered, based on their individual needs. For example, we might suggest a brow lamination to complement a threading treatment, or recommend a serum to maintain lash extensions.
“When clients trust our recommendations, they’re more likely to return – making upselling a tool for long-term loyalty, not just short-term gain.”
Nicola Moras, Business Coach, Visibility Expert & Motivational Keynote Speaker
“Remind your team that offering an upsell is just a question. You’re not asking the customer for a long-term commitment. You’re offering a helpful option. No drama. No pressure.
“No one wants a canned ‘Would you like to add this too?’ upsell. It feels robotic and, let’s be honest, lazy. Instead, reframe upselling as adding value. If what you’re offering solves a real problem for that human in front of you, it’s not a sales pitch. It’s good service.
“Train your team to listen properly, spot the need, and make recommendations with confidence. People appreciate an upsell when it helps them. And if it doesn’t, they’ll say no. Simple. But don’t make that decision for them.
“When people order online, they’re not offended by ‘Is this a gift? Add wrapping for $5’ or ‘Want to add insurance to your delivery?’ We’re used to it. When it makes sense, we say yes. It’s the same in person.
“Shifting from selling to serving builds trust. It boosts conversions and makes everyone feel good about the experience.
“Give your team permission to serve, not sell. When they get that the upsell is about impact, not pressure, everything changes.”
Grace Savage, Brand & AI Strategist, Tradie Agency
“The secret to upselling without being pushy is simple: solve the real problem, not just sell the product. People hate being sold to, but they love being helped.
“Train your team to use permission-based selling. Always ask: “Would it be helpful if I showed you another option that might suit you better?” This lowers resistance, builds trust, and puts the customer in control.
“Great upselling feels like great service. It happens when your team genuinely understands the customer’s needs – not just a list of features. For example, instead of saying “Upgrade to our premium plan,” say ‘You mentioned needing faster turnaround – this plan gives you 24-hour support so you’re never left waiting.’
“Here’s a powerful tactic: down-sell first. If a customer is eyeing the top-tier product but doesn’t need it, recommend the smaller option. That move earns trust, and the next time they do need more, they’ll come straight back.
“Upselling isn’t about pressure. It’s about timing, trust, and solving the next problem before the customer even has to ask.”
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