sales leadership

Why Your Cross-Selling Strategies Aren't Working

cross selling metrics

An Effective Cross Selling Strategy is Rooted in Early Conversations

Cross Sell. Land and Expand. Enterprise Selling. Account Management. So many names for the same sales motion. We want salespeople to sell more #$%! to existing accounts.

Every year you review your addressable market. You analyze your ‘whitespace’. The conclusion is the same – cross selling is the easiest way to hit your number.

Yet, every sales leader of every company with more than one offering has the same complaint:

Why can’t our reps sell other products to their current customers?

Shouldn’t the hard work be done already? After all, the rep is in the door, built some type of relationship, learned something about the customer’s business. Communicating the value of additional products or services should be easy, right?

Inevitably, the finger pointing starts:

  • It’s the comp plan – we just need to pay people to do the right thing.
  • It’s the role design – if only someone was accountable for this.
  • It’s the org model – they just need to bring in the right specialists.
  • It’s the training – they only need to learn how to sell.

As frustration boils over, the predictable responses come. A new round of product webinars and training sessions. Pumping more content into the field to make sure every rep knows everything about the full product catalog. If reps know more about the products, more cross selling will certainly follow.


More times than not, cross selling doesn’t improve. And the finger pointing starts all over again.

What Makes Cross Sell Work?

Every company has at least one great cross selling example. The customer saw real value in the broader capabilities of the firm. Internal sales and delivery resources partnered to make it happen. Account profitability soared. That story has grown into a full-blown corporate legend. And the account executive has probably achieved hero status.

Listening to our clients describe these good cross selling examples reminds us of someone describing a UFO sighting. There’s a sense of amazement and wonder. But folks struggle to explain how it occurred. The story typically ends with an appreciation of its uniqueness. There’s almost a sense that they may never see it again.

But in these rare cross sell victories, there are nuggets of wisdom. And no surprise, success comes more than additional product training.

Let’s look at three things we do find when effective cross selling happens:

1. Cross sell started early in the process. In nearly all successful cross-sell opportunities, the positioning of broader capabilities occurs early.

One of the biggest mistakes we see is trying to ‘go back’ to customers to upsell or cross sell. This is a hard road. Effective cross selling strategies are rooted in early conversations.

Initial discussions are the time for casting a wide net into the prospect’s challenges. It’s the ideal venue to explore the customer’s bigger landscape. The selling team establishes value for the breadth of their firm’s offerings by anchoring to a broader set of customer issues, from the beginning. This is true even if the customer thinks they’re only interested in a point solution.

Effective cross selling means not screwing up that first touchpoint. And that requires paying attention to the logistical details of the meeting itself. Think about the physical setup of these meeting room – does it lend itself to informal and open dialogue? The best reps leverage whiteboards, flip charts, and workshop formats to facilitate a more expansive discovery conversation.

2. The products really fit together. Customers must see logic in your product portfolio. They should understand the connections between your different offerings – literally, how they piece together to create business value for them.

The way one of your products connects to another shouldn’t take a lot of explanation. It needs to be intuitive. It should match how customers think about their issues and how their buying centers are organized.

The sequencing of the purchase decision for each product also needs to be clear to both sellers and buyers. Asking reps to engage buyers around different products in the wrong order is common. The right sequence is customer-driven – in what order do issues arise around a particular initiative or problem?

Asking sellers to connect the dots when the value of the product eco-system is clear leads to better cross sell. Unfortunately, many sellers are asked to cross sell into different buyer profiles or buying centers within a single account. And often the solution sets aren’t connected in any customer-facing way.

3. The seller had the right mindset. When it comes to differences between good or bad cross selling, it often comes down to differences between sales reps. And we’re not talking about traditional selling skills. The main differentiator between average and high-performing cross sellers is the right mindset.

What does an effective cross-sell mindset look like? It’s a seller who fearlessly dives into aspects of the customer’s business where they might have little personal expertise. They’re comfortable discussing issues and solutions even when they’re not deep experts. They have intellectual curiosity and commercial savvy to wade into a wider topics.

Through this open-minded approach to discovery, they learn more. More about the issues, more about the people, more about how decisions get made. This additional information becomes essential to positioning and selling ‘the next thing’. These reps understand that their role – even with highly technical products – is to first qualify cross sell opportunities. They go solo with initial discovery and qualification, bringing in other product specialists only when needed.

Too many reps stay in their comfort zone. This is especially true in more complex technology sales. Some of the very best cross-sellers come from consulting or professional service backgrounds. They instinctively view a customer’s situation more holistically. And this helps them build buy-in to a multi-product roadmap.

Building Your Cross-Selling Culture

The power of cross selling as a growth strategy is unmatched. And the importance of this strategy has never been greater as we enter an uncertain economy. As recessionary signals increase, the appeal of a buyer’s resistance to change also increases. Leveraging current customer relationships for more revenue is a critical hedge.

In strong cross selling cultures, reps turn the tables to see things from the buyer’s lens. The best cross sellers take a demand-driven view of their products vs. a supply-side perspective. While solid product training is also needed, improving cross selling takes more.

The right motivation and accountability are essential. The sales team must know that cross selling is not an ‘above and beyond’ activity. It's an expected behavior and they will be held accountable. As you make cross-selling objectives crystal clear, give reps flexibility in how they execute it. This means putting the responsibility on the rep to identify which customers are right for expansion and the right timing for additional product introductions.

It’s not too late to implement new cross-selling strategies. It may make all the difference in hitting your targets this year. Contact us to learn more best practices and practical strategies we see in the leading cross selling teams.

About The Author

Author photo Researcher, consultant, and sales leader, Brian uses a data-driven approach to drive sales effectiveness. His clients include leading sales organizations in financial services, technology, healthcare, and professional services. Using insight from academics and change management, Brian helps senior leaders and sales enablement teams understand and succeed in today’s more demanding market. His research has been published in Harvard Business Review and other outlets.

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