How should sales reps respond to losing deals?

Matt Plank · Dec 20, 2024

How a rep handles a 'no' matters enormously — treating losses with kindness builds a loopback pipeline that returns as faster, easier deals

After a year to eighteen months in role, past prospects circle back and are immediately ready, so deal cycles move much faster the second time

6:11 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank

Matt Plank · Dec 20, 2024

Reps should respond to a loss by killing the buyer with kindness — thanking them, asking for feedback, and leaving the door open — because deals bounce back unexpectedly

Competitive salespeople naturally react badly to no, but if you exit every interaction graciously, buyers return months later when the winning vendor lies, implements badly, or doesn't deliver what it promised

Scope: Matt frames this as something he had to learn after reacting poorly himself

39:23 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank

Lauren Schwartz · Oct 19, 2022

Salespeople should learn to expect rejection, because once you expect a no, asking for what you want stops being scary

Happiness is reality minus expectations, so lowering the expectation removes the fear even though the sting of rejection never lessens

35:35 Expecting rejection removes fear of asking though the sting remains

Harry Stebbings · Dec 20, 2024

It is not okay to be comfortable with losing; losing should hurt every time and be remembered

So you never feel it again

4:12 Losing must always sting never be accepted

Matt Plank · Dec 20, 2024

Loving winning and deeply hating losing are the same thing; what matters is that losing stings and motivates rather than derails you

Even the best reps have win rates of 20-40%, so you lose most opportunities every month and must bounce back

4:22 Hate losing but bounce back since most deals are lost