*Disclaimer* I am writing this post in a personal capacity; the opinions I express are my own and do not represent my employer.

I think that more people and orgs (especially nonprofits) should consider negotiating the cost of sizable expenses. In my experience, there is usually nothing to lose by respectfully asking to pay less, and doing so can sometimes save thousands or tens of thousands of dollars per hour. This is because negotiating doesn’t take very much time[1], savings can persist across multiple years, and counterparties can be surprisingly generous with discounts. Here are a few examples of expenses that may be negotiable:

For organizations

• Software or news subscriptions
  • Of 35 corporate software and news providers I’ve negotiated with, 30 have been willing to provide discounts. These discounts range from 10% to 80%, with an average of around 40%.
• Leases
  • A friend was able [...]

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