“No” seems to be the hardest word: Why getting a Yes/No is better than a “Maybe”

Celine Wee
3 min readDec 24, 2022


Sorry is indeed a hard word (I won’t contradict Elton John), but I propose in this post that “No” is the hardest word in deals and decisions. The infiltration of “Maybe”, instead of a “Yes/No”, while seemingly promising, is the “No Man’s Land”, where deals die and decisions falter.

Why cast such a gloomy picture? The charming hope in the “Maybe”…

  • The deal closes
  • The decision maker says yes
  • The partner agrees to something we want

Is more comforting than

  • The deal is lost
  • The decision maker says no
  • The partner disagrees with we want

However, the comforting “Maybe” is more damaging than getting a Yes/No.

I’ll explain this in three points:

  1. Why “Maybe” tends to be the default
  2. What the (bad) consequences of “Maybe”
  3. How to drive to a Yes/No vs “Maybe”

Diving in

1/ Why “Maybe” tends to be the default

It’s hard for people to say no [1], due to reasons like not wanting to be impolite, guilt/obligation, fear of disappointing someone, feeling unkind etc. Since saying “Yes” is a commitment, a “Maybe” is safer— keeps options open, and avoids confrontation. This means that even when the answer is a “No”, you might hear a “Maybe” as a placeholder.

2/ What the (bad) consequences of “Maybe” are

In sales training, we were strenuously taught to drive to a Yes/No vs Maybe. Here’s some reasons why “Maybe” is bad:

  • Time waste: the sales deal is already lost but you continued to spend time on it, instead of other high potential deals.
  • Missing goals: failure to form a partnership, or a mad scramble for other options, leading to delayed timelines or outcomes negotiated in a rush.

In contrast, the benefits of getting to an early “No” means:

  • Time: You stop spending time into the lost deal and spend time on other deals to hit quota/targets.
  • Reaching goals: you explore and pressure test other options, to find mutually beneficial ones.

So, indefinite “Maybes” are bad.

3/ How to drive to a Yes/No vs Maybe

  1. Ask directly for a decision. This might not work in all cultures, but assuming the right moment and context, ask.
  2. Ask about timelines for a decision. If there’s no timeline, you are in the “Maybe” zone and are not a priority. The chances of closing that deal is zero to unlikely.
  3. Ask what “No” reasons might be, be curious about the reasoning (listen, not talk).

The points above assume baseline deal management hygiene:

  • You’ve done the basics to qualify the deal
  • You’re working with the right decision maker(s)

You can read about both here.

Photo by Amy Hirschi on Unsplash

Deals and decisions take time, and of course there is a period of time there’s a “Maybe” zone, before a decision is made. There is a time to sell, to persuade, and to push. But such activities cannot go on indefinitely. There is a time to get to a “Yes/No” and bring finality and clarity. It’s hard, but worth it.

[1] Some helpful articles here and here



Celine Wee

Musings are my own: a collection of learnings from Payments, Go To Market, Web3, Biz Ops across Stripe, Coinbase, Twitter. I also write @ celinewee.substack.com