When a prospect asks for a free pilot, treat it as a sign that you failed to build enough confidence in the outcome. Instead of agreeing, diagnose their uncertainty by asking what they still need help predicting. This shifts the conversation back to value and avoids deploying your best resources on your least committed customers.

Frame every negotiation around four core business drivers. Offer discounts not as concessions, but as payments for the customer giving you something valuable: more volume, faster cash payments, a longer contract commitment, or a predictable closing date. This shifts the conversation from haggling to a structured, collaborative process.

Prospects who haven't bought your type of solution in a long time lack proper context. They will compare your modern, high-value offering to a cheaper, older, or simpler alternative they understand, leading to sticker shock unless you proactively reframe their perspective.

Instead of just sending a proposal PDF, record a two-minute video walking through the pricing. This 'eliminates the game of telephone' by allowing you to directly explain the value behind each line item to the ultimate budget holder, ensuring your champion doesn't miscommunicate the message.

Don't let your personal perception of what's 'expensive' limit your earning potential. Set your price high based on the value you provide. It is easy to lower a price that gets no buyers, but impossible to know if you could have charged more if you start too low. Never say no for the customer.

By proactively asking about potential deal-killers like budget or partner approval early in the sales process, you transform them from adversarial objections into collaborative obstacles. This disarms the buyer's defensiveness and makes them easier to solve together, preventing them from being used as excuses later.

Selling a small, cheap "land" deal to an enterprise customer is dangerous. When you try to expand, they will question the 10x price jump, making it nearly indefensible. Start with a price ($75k-$150k) that reflects enterprise value to avoid being trapped by a low initial anchor.

Discomfort with concepts like income statements or margins causes salespeople to shy away from conversations with CFOs and other executives. This self-imposed limitation prevents them from connecting their solution to core business metrics like cost, revenue, and profit, trapping them in lower-level discussions.

Instead of hiding price until the end of the sales cycle, be transparent from the start. Acknowledge if your solution is at the high end of the market and provide a realistic price range based on their environment. This allows you to quickly qualify out buyers with misaligned budgets, saving your most valuable asset: time.