How Sales Leaders Can Help Their Teams Win More Deals

Capturing a prospect’s attention has never been more challenging. Your print sales team may have all the right tools – solid research, carefully vetted contact lists, and compelling messaging – yet still struggle to get meetings. So, what’s missing? And how can you, as a sales leader, help them break through the noise and turn opportunities into wins?

Start by shifting the initial focus from selling to having real conversations – meaningful conversations. Many salespeople approach prospecting with a rigid goal of landing a meeting, but that’s not always what the prospect wants, or needs. Instead, encourage your team to engage in a conversation – just like they might if they were at a networking event (you remember those don’t you?). Buyers today have inboxes full of generic sales pitches and are quick to tune out anything that doesn’t feel relevant. A well-crafted, personalized approach that prioritizes understanding their business over making a sale will always stand out. Show them that you actually did do a little bit of research.

In a world increasingly focused on digital communication, genuine human connection is becoming rare. Emails and texts are efficient, and are great once a transaction has begun, but they lack the depth needed to build trust with someone new. People are more protective of their time than ever. They screen calls and ignore unsolicited messages. Your team needs to cut through the digital clutter by demonstrating curiosity and a sincere interest in solving problems. Be interesting and interested. When prospects feel like they’re being heard rather than sold to, they’re far more likely to engage.

Be interesting and interested.

All your reps have to sell is their time. To maximize their efficiency, your team must be strategic about where and how they invest their time. Not every lead is worth pursuing, and chasing every potential opportunity can lead to wasted effort. Guide your team toward focusing on high-value prospects—businesses that align with your solutions and demonstrate a real need. Ok, here’s a quiz: How many of the active prospects that your team is chasing actually come close to your ideal client profile – I thought so. A well-thought-out mix of targeted outreach, social media engagement, networking, and timely follow-ups – to the right audience will yield better results than a scattershot approach.

Personalization is another key differentiator. A one-size-fits-all message isn’t going to cut it. Prospects can instantly tell when they’re receiving a generic pitch. Encourage your team to do their homework, tailor their communication, and connect their solutions to the prospect’s specific challenges. Taking the time to craft a thoughtful message not only increases response rates but also sets the stage for a more productive conversation. More companies today are doing a great job with their social content. Your sales team only needs to piggyback off of those efforts and add their spin to the topic to help re-enforce their position as an industry expert.

Once your team gets a prospect on the phone, the real work begins. It’s not about jumping straight into a sales pitch—it’s about diagnosing before prescribing. Think about it: If you walked into a doctor’s office and they handed you medication without asking any questions, you wouldn’t trust their judgment. The same principle applies to sales. Your team needs to listen and provide market insight, uncover pain points, and provide solutions that genuinely address the prospect’s needs. Rushing to pitch without first understanding the problem is one of the fastest ways to lose credibility.

One of the best ways to strengthen sales conversations is through consistent coaching and practice. While role-playing might not be the most exciting exercise, it’s incredibly effective. The more comfortable your team is in handling objections, refining their messaging, and discussing pricing with confidence, the more natural and persuasive they’ll be in real situations. Think of this as your practice sessions. The better a star performer practices, the better they are in a game. Sales isn’t just about knowing what to say – it’s about saying it in a way that feels effortless and authentic. And yes, it’s game time!

Beyond the conversation itself, sales success depends on positioning value rather than just pushing products. Buyers don’t care about specs or features unless they understand how those features translate into real-world benefits. Encourage your team to tell stories and share examples of how your company has solved similar problems for other businesses. Everyone has a story, what’s yours? When prospects can visualize the impact, they become more open to moving forward.

Leveraging technology is another way to enhance efficiency. If your team is still managing leads manually, they’re spending valuable time on administrative tasks instead of selling. CRM systems, automation tools, and data analytics help streamline the process, keeping outreach organized and ensuring follow-ups don’t slip through the cracks. Face it, CRMs don’t enjoy good adoption rates at most printing companies. That said, I could argue that many printing companies are still selling the way they did 10-15 years ago. If that’s working for you, great. But times have changed, buyers have changed and the need to increase the sales effectiveness of the business has never been more important.

But efficiency isn’t just about the tools—it’s also about mindset. The best sales teams aren’t just those with the best technology; they’re the ones committed to continuous improvement. As a sales leader create an environment where learning is encouraged, whether through team strategy sessions, peer-to-peer coaching, or professional development opportunities. When your team feels supported, challenged, and motivated, their performance naturally improves.

At the heart of all this, sales isn’t just about persistence – it’s about being strategic, intentional, and, above all, human. The right mix of focused prospecting, meaningful conversations, personalized outreach, and strong coaching can completely transform your team’s success. And remember, knowing what to do is only part of the equation – actually applying these strategies is what makes the difference.

Mike Philie can help validate what’s working and what may need to change in your business. Changing the trajectory of a business is difficult to do while simultaneously operating the core competencies. Mike provides strategy and insight to ambitious owners and CEOs in the Graphic Communications Industry by providing direct and realistic insight and advice, not being afraid to voice the unpopular opinion and helping leaders navigate change through a common sense and practical approach. Learn more at www.philiegroup.com, LinkedIn or email at mphilie@philiegroup.com.

The preceding content was provided by a contributor unaffiliated with Printing Impressions. The views expressed within may not directly reflect the thoughts or opinions of the staff of Printing Impressions.