It’s that time of year when everything feels like it’s changing.
Budgets are resetting. Territories are shifting. Supply chains are still messy. Costs are up. People are
leaving. And sales professionals everywhere are finding themselves in conversations they didn’t ask for but can’t avoid.
These are not “product pitch” conversations.
They’re not about features, benefits, or closing techniques.
They’re relationship-defining conversations.
I’ve been spending a lot of time lately designing and producing AI-driven role-playing exercises for clients using our Strategic Business Selling™ curriculum. In these simulations, participants practice some of the most uncomfortable conversations imaginable—and get immediate, blunt feedback.
What’s interesting is this:
The best sales professionals don’t avoid these conversations.
They lean into them with clarity, humility, and business acumen.
Below are five of the hardest sales conversations and how to handle them in a way that strengthens, rather than damages, the relationship.
1) “I’m Your New Representative”
You’re replacing a sales rep who just resigned, retired, or worse, was beloved by the customer.
This is not the moment to sell.
This is the moment to listen.
Best practices:
- Acknowledge the change directly. Don’t minimize it.
- Respect the relationship your predecessor built.
- Avoid the temptation to “prove yourself” too quickly.
How to handle it:
Start with humility.
Say something like: “I know transitions like this can be frustrating. My goal isn’t to replace what worked—it’s to understand it and build from there.”
Then ask smart questions. Learn what mattered. Learn where trust was earned—and where it may have been strained.
Customers don’t expect perfection on Day One.
They expect self-awareness and respect.
2) “We Are Raising Prices”
Few sentences make a customer’s stomach drop faster than this one, especially when the increase is north of 10%.
This is where weak salespeople hide behind emails and PDFs.
Strong ones show up prepared.
Best practices:
- Never surprise the customer.
- Explain why, not just what.
- Anchor the conversation in value and business impact—not excuses.
How to handle it:
Frame the increase in the context of their business.
Talk about cost drivers, investments, service levels, and long-term sustainability.
And then, this is critical, pause.
Let the customer react. Don’t rush to fill the silence. Don’t get defensive.
Price increases don’t kill relationships.
Poorly handled price increases do.
3) “You’re on Allocation”
You’re calling to say you can only deliver 80% of what they expected.
Translation: “I know you planned your business around us, and now we’re letting you down.”
That’s heavy.
Best practices:
- Own the issue immediately.
- Be specific and factual.
- Come with options, not apologies alone.
How to handle it:
Say it clearly. Say it early.
Then shift quickly to problem-solving.
- What can be prioritized?
- What alternatives exist?
- What visibility can you provide going forward?
Customers can live with bad news.
They struggle with uncertainty and vagueness.
4) “Your Favorite Service Manager Left”
This one is emotional, not transactional.
You’re not just losing a resource.
You’re disrupting trust.
Best practices:
- Acknowledge the loss personally.
- Share what’s being done—not corporate platitudes.
- Stay involved during the transition.
How to handle it:
Recognize the relationship that existed.
Let the customer express frustration or concern.
Then outline the plan:
- Who’s covering short-term
- How continuity will be maintained
- How feedback will be handled
This is where sales professionals either disappear or step up as relationship owners, not just account managers.
5) “We’re Eliminating That SKU”
You’re discontinuing a product that customers rely on and maybe love.
This isn’t about inventory.
It’s about disruption.
Best practices:
- Give as much notice as possible.
- Explain the business rationale.
- Provide clear migration paths.
How to handle it:
Don’t position it as “corporate decided.”
Position it as a strategic shift—and help them navigate it.
Offer alternatives. Share timelines. Help them plan.
The goal isn’t to win the argument.
It’s to protect their outcomes.
Final Takeaway
Difficult conversations are not a distraction from selling.
They are selling.
Handled poorly, they erode trust fast.
Handled well, they deepen relationships in ways no pitch deck ever will.
The best sales professionals are:
- Transparent
- Prepared
- Humble
- Grounded in business reality
And they understand one simple truth:
How you show up when things go wrong matters far more than how you perform when everything is going right.
