The Hard Question Doesn't Kill The Deal. It Moves It.

Asking hard questions in sales brings up the same type of anxiety I had when I was a kid sitting outside the principal’s office for being naughty.

I had a million dollar expansion deal with an existing customer and the renewal contract was still in negotiations. Given the legal teams wanted their pound of flesh, I realised that we weren’t going to finish before the renewal date.

The position was clean and icy cold. If we don’t get this done by the date, we’re turning off the subscription. I had to ask key stakeholders something no one wanted to talk about: what’s the backup plan the following day if the subscription stops working? They knew the answer. There isn’t one.

Calling out the elephant in the room didn’t kill anything. Quite the opposite — it forced the next question: how do we work together, in small and practical steps, to ensure no downtime. That question had an answer. That answer was a plan.

The plan got us working a bunch of tasks in parallel. Legal prioritised the clauses that let the champion write the briefing note. We mapped the key product capabilities so we could brief support and customer success. One by one, we ticked off the things we could actually manage and got the renewal and the funding locked away.

The hard question doesn’t just unearth if the deal is real. It’s how you give it motion.