We've decoupled timelines from estimates almost entirely and to the ire of all our sales and C-Level only give out Quarter based estimates anymore. "End of Q3 or early Q4". When we deliver mid Q3, everyone is happy. The funny bit is that since we've made these changes, we've not noticed any drop in client interest at all. What we do notice is that we actually ship what we promise (sometimes even more). We also don't have clients who think we'll do 10 hours of work for free anymore, because we've anchored the value of every little bit we do properly. We also filter the stingy clients who are completely pointless and are just wasting our time, while engaged with our competitors.
There's a lot, a looooot of FOMO in sales on the side of our own sales people. So they lowball their shit to make sure we close. Then we can't keep what's promised and nobody is happy and contracts that would only be profitable after like 3 years don't get renewed and we lose a client. Great stuff. Then try and get them back after a shitty experience like that.
The mind boggles.
I once had a sales-bro tell the client we'd "monitor the internet for X". That has remained one of the most important hammers for me to wield when discussions even start coming up. How the fuck does one "monitor the internet" to a degree that fits the clients interpretation of this phrase. Sales guy is still with us and a good lad, he owns that mistake. But fuck was it ever crazy.