Question 1

How long should AI continue following up on a lost deal?

Accepted Answer

For high-value deals, 12-24 months of structured re-engagement makes sense. For lower-value deals, six months of lighter-touch outreach is typical. The investment in re-engagement should be proportional to the potential deal value.

Question 2

Does automated lost deal follow-up feel inappropriate to the prospect?

Accepted Answer

Not when it is relevant and genuinely useful. A follow-up that provides a useful insight, acknowledges that the timing may now be right, or references a specific change in circumstance is welcomed. A follow-up that simply says 'have you reconsidered?' is not.

Question 3

Can AI re-engage lost deals from years ago?

Accepted Answer

Yes, if the contact data is still valid and there is a relevant re-engagement reason - a new product, a significant price change, a capability development. Re-engaging very old lost deals requires a refreshed and specific reason rather than a generic 'just checking in' message.

How does this AI workflow operate in practice?

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