Yes, if…

People love hearing “yes.”

In a meeting, it sounds like momentum. In Slack, it reads as alignment. On a roadmap, it feels like progress.

It's also the first step towards disappointment. "Yes" is a contract - a commitment to deliver something. If you say "yes" to everything, you start paying for it with late nights, dropped balls and a creeping resentment that's hard to admit because you chose to say yes.

Every “yes” goes on an invisible ledger. Time, attention, credibility. All quietly debited, rarely reconciled. Eventually you will go bankrupt and disappoint someone. The only question is whether you disappoint them when they ask, or later when your lack of delivery has a much higher cost.

The two types of "yes"

We say “yes” for many reasons. In personal relationships, it can strengthen bonds and make others feel valued. In professional settings, saying “yes” can signal teamwork, ambition, and a commitment to shared goals. However, saying “yes” can also be driven by fear. A fear of disappointing others, a fear of missing out, or a fear of conflict.

No matter why we say yes, the expectation to be agreeable leads to us committing to way more than we can ever hope to achieve. You say yes to avoid disappointing someone, only to disappoint them at the worst possible time: after you've agreed, they've told other people about their idea and half of the org is excited.

So, how do you keep the momentum that "yes" brings without overcommitting yourself? By using "Yes, if."

"Yes, If" is a trade

“Yes” pretends there is no conversation. It hides the cost and defers the pain.

“No” without context shuts the conversation down before anything useful is learned.

“Yes, if” is the conversation.

“Yes, if” makes the cost visible. It takes the invisible tax you were about to pay and puts it on the table where everyone can see it. Not as a complaint. Not as drama. As accounting.

• “Yes, if you can wait until Thursday after the report goes out.”
• “Yes, if we agree this replaces the other thing I’m doing.”
• “Yes, if you do the first draft and I’ll review.”
• “Yes, if we can fund the work and assign an owner.”

Most frustration at work doesn’t come from disagreement. It comes from ambiguity.

Applying this in real life

A good “Yes, if” is just good bookkeeping. It names which account you’re drawing from.

• Time: “Yes, if it can wait until Thursday.”
• Priority: “Yes, if Bob agrees this outranks the report.”
• Ownership: “Yes, if you draft it and I’ll review.”
• Scope: “Yes, if we do a 1-page version, not a full report.”
• Resourcing: “Yes, if we fund it / staff it.”

Most org pain comes from pretending those currencies are infinite. By explicitly naming them and negotiating with the requester you can be collaborative without overcommitting.

Price the work

“Yes, if” is about maintaining balance. It’s about making sure the work you agree to aligns with your time, energy, and priorities.

Next time someone asks you for something, name the trade-offs. Make the constraint explicit. Price the work. See if they still want it.

If that trade kills the request, it wasn’t a priority. It was just an idea looking for someone else to carry the cost.

“Yes, if” is about maintaining balance. It's about making sure that projects align with your time, energy, and priorities. It fosters collaboration without compromising your well-being. Next time you’re faced with a request, remember: you don’t have to say “yes” to everything, but with the right conditions in place, you might just find a way to make it work for everyone.