We Tried This Before Objection Drill

What is the buyer really saying when they say we tried this before?

The buyer is telling you a past decision cost them something, and they are checking whether you will be the second cost. The sentence sounds like a verdict on your category. It is usually a report on one specific failure.

That failure takes one of four forms. The product could not do the job. The product could, but the rollout failed because nobody owned it, nobody had time, or the data never got cleaned up. The vendor went quiet after signature. Or nobody defined what success looked like, so nobody could say whether it worked.

A rep cannot tell which form from the words alone. Reps who guess default to the one they find easiest to argue against, which is almost always a defense of the product. That is the root error this drill removes.

The same logic applies to a past vendor failure objection in any category. The buyer is not asking for a rebuttal. They are asking whether you will find out what happened before you start talking.

Failed rollouts and failed products need different next steps. A rollout failure points to scoping, ownership, and success criteria. A product failure points to an honest fit check. Treating them as the same problem produces a pitch that answers neither.

A buyer who says they tried this before is reporting one specific failure, and the rep's first job is to find out which.

What is the one agreed first response?

The agreed first response is one sentence of acknowledgement followed by one question, and every rep on the team says the same thing. We recommend this wording:

I'm glad you told me that. Before I say anything about us, what happened?

The sentence has three jobs. It treats the history as real. It signals that the rep will not start pitching. It asks one open question that the buyer can answer from memory. It contains no product noun, no claim, and no comparison.

Some managers worry that an agreed line sounds canned. The trade-off is real: a memorized line delivered flat is worse than a good improvised one. We still recommend agreeing on the first response, because the branches that follow are where strong reps improvise from understanding. Only the opening needs to be automatic, since that is where reps panic and start defending.

Build the line from the actual words your buyers use. The sales objection library guide covers how to collect those words, so the drill runs on the phrasing your market really produces rather than a textbook version.

An agreed first response is useful because it is boring, and the improvisation belongs in the branches that follow.

How does a rep separate a failed product from a failed rollout?

The rep separates them by letting the buyer's answer to what happened sort the cause, then restating that answer in the buyer's own words. The rep does not argue a position. The buyer's account does the sorting.

Listen for the noun the buyer uses as the subject of the failure. If the subject is the tool, the failure is probably about product. If the subject is people, time, or ownership, it is probably about rollout. If the subject is the vendor, it is about service. If the buyer cannot name a subject, success was never defined.

After the answer, restate it in one or two sentences using at least one of the buyer's own phrases, then ask whether you have it right. The restatement is the pass-bar moment, and the sales listening drills cover paraphrasing as a scoreable skill.

If you teach the Sandler pain funnel, note that it is an ordered sequence: surface issue, then concrete cost, then feeling. In this drill the diagnostic question stands in for the opening step. The cost question, what that failure cost them, comes only after the buyer confirms the restatement. Do not open with how they feel about it.

The buyer's own subject for the failure, whether tool, people, or vendor, tells the rep which conversation to have next.

What does a failing attempt sound like?

A failing attempt says something about the product, the prior vendor, or a customer before the buyer has confirmed what went wrong. There are three versions, and each one is easy to hear in a transcript.

Defending the product. Our platform is different. That kind of failure is exactly why we built it the way we did. The buyer chose the earlier product for reasons. A defense tells them their judgment was the problem, and the conversation becomes an argument the rep cannot win.

Attacking the prior vendor. Honestly, they've had a lot of complaints, and their implementation team is thin. The rep cannot verify this, and the buyer may still have a relationship with that vendor. The claim also puts the buyer in the position of defending their past choice.

Jumping to a case study. We had a customer in the same spot, and here's how it went for them. A story answers a question the buyer has not asked. It assumes the cause is the same, which is the one thing the rep has not established.

All three share one tell: the rep has stopped asking. Count the question marks in the rep's first three turns after the buyer's line. If the answer is one and the rest is statements, the drill has already failed.

Every failing response to this objection replaces a question with a claim the rep has no evidence for.

Worked drill: setup and the three buyer runs

We recommend running this as a 30-minute block: 5 minutes of setup, 15 minutes of drill, and 10 minutes of debrief. Scenario prep happens beforehand. The manager spends about 10 minutes choosing a scenario from a live deal and the rubric row to score, in this case the objection-handling row.

The drill is three runs of about 4 to 5 minutes each. In every run the buyer opens with the same line: We tried something like this before and it didn't work. The buyer persona gives details only when asked. If the rep pitches before asking, the buyer answers Sounds like what they told us, and the run is over.

Run 1, product gap. When asked, the buyer says It couldn't pull the fields we needed from our CRM, so we dropped it. If your product handles that, the rep says so in one sentence after the buyer confirms the restatement. If it does not, the rep says so plainly.

Run 2, rollout failure. The buyer says Honestly, nobody owned it. Our ops lead left and it just sat there.

Run 3, evasive buyer. The buyer says It just didn't work. I don't want to go back over it. The rep gets one narrowing question: Understood. Was it the tool itself, or what happened after you bought it? The rep may not push past a second refusal. If the buyer answers the narrowing question, the run continues as in Run 1 or 2. If the buyer declines again, the rep restates the refusal itself and moves to a low-pressure close.

Run these live with a peer playing the buyer or against an AI persona. Record and transcribe every run, because the evidence check below works only from the transcript.

What is the pass bar, and what evidence can a manager check?

The pass bar is five rubric rows met on each of the three runs, and a manager can verify each one from the transcript alone. Any miss is a fail for that run, and the run is repeated. Run 3 uses a defined variant of Rows 3 through 5, because the buyer never names a cause.

Row 1. The first rep turn after the buyer's line holds one sentence of acknowledgement and exactly one question, with no product noun. Evidence: read that single turn.

Row 2. Nothing is said about the rep's product, the prior vendor's quality, or any customer until the buyer confirms the restatement. Evidence: search the transcript for the product name, the vendor name, and the word customer. Every hit must come after the confirmation timestamp.

Row 3. The restatement reuses at least one phrase the buyer actually said. In Run 3, the rep restates what the buyer did give, for example It didn't work, and you'd rather not go back over it. Evidence: match the rep's restatement turn against the buyer's earlier words.

Row 4. The buyer's next turn confirms it, for example Yes, Right, or Exactly. Evidence: read the turn after the restatement. A rep opinion that it landed does not count.

Row 5. The rep closes with a next step tied to the named cause, or states a fit gap honestly. In Run 3, where no cause is named, the rep closes with a low-pressure next step that assumes no cause, or says plainly what remains unknown. Evidence: read the final rep turn. In Run 3, a close that assumes a cause the buyer never named fails this row.

A failing attempt sounds like Row 2 broken: We're different from them, and let me tell you why. It can also be Row 4 missing, where the rep restates and then keeps going without waiting for the buyer. Talk/listen ratio on the scorecard is worth a look when a run fails, as an input to investigate. It is not a pass bar, since a rep can talk less and still defend the product.

A pass on this drill means the buyer confirmed the cause before the rep said a word about the product.

How should the debrief and re-run work?

Pick one failed moment, let the rep find it, then schedule the re-run before the debrief ends. Do not review all three runs. Feedback covering several issues at once is entertainment, not coaching.

Use this script. Manager: Find the first sentence where you said anything about our product. What had the buyer confirmed by then? Let the rep answer and name the row. Only then give your verdict, and keep it to that one row. Finish with: We re-run Run 2 on Thursday. Same buyer, same line.

The re-run happens within the week, against the same persona, scored on the same five rows. A rep who passes on the second attempt has passed. A rep who fails twice moves to a remediation conversation. Our sales roleplay debrief guide covers the one-behavior format in more detail.

Keep this block separate from pipeline review. If it shares a calendar slot with deal inspection, deals will absorb it.