It hurts to ask

“It never hurts to ask!”

I get this advice a lot. It’s bullshit and we all know it.

We hate getting asked for things. It’s painful at a visceral level to have to say no. We generate narratives about the ask-er to justify the “no” we have to deliver. “They are CRAZY to ask me for this” or “what a snake to ask for something so out of bounds”.

It doesn’t matter that they were “just asking” and that we’re free to push back or say no - the emotional damage of the ask is done when the ask is made. Recently, an investor told me they’d received bad feedback about a close friend of mine during DD reference checks. The bad feedback stemmed entirely from two “asks” he made in previous compensation negotiation. I can’t think of a worse reason to harbor bad feelings against a startup executive, but I’m not surprised. Because it hurts to ask.

Beyond the personal toll asks take, each ask has an outsized effect on slowing down a negotiation and putting any particular deal at risk. If you ask something even slightly unexpected of the other side in a negotiation, they have to understand it, discuss it, and decide whether to counter it or even walk away, before they can come back to you with changes or a decision. The effect multiplies quickly as you add asks into the process, and negotiations that should have taken days can take weeks or months. Companies and priorities can change quickly, and a negotiation that takes months is at risk by default.

My advice: on a personal level, set expectations early for the asks you’re likely to make and don’t make asks that aren’t important. From a business perspective, keep the number of asks you make of your counterparty in a negotiation as narrow as possible. Ideally, if you’re the vendor, make only 1 ask and make it price. Any other asks you want to make (public reference, term, etc) should come as counter-asks when your customer pushes back either on your ask or something they need internally (compliance requirements, support, exclusivity, etc). It hurts to ask but asking is important, so keep your asks narrow and keep them clear.


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