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Question for freelancers about contracts

How do you usually send contracts to clients for signing?

My process looks like this every time:
– send a PDF
– client says, “I’ll look at it later.”
– I follow up after a couple of days
– follow up again
– eventually it gets signed… or I lose the file in my inbox

Is this just normal freelance life, or am I doing something wrong?

on December 28, 2025
  1. 1

    This is pretty normal freelance life, but there are ways to reduce the friction:

    1. Make signing as easy as possible - tools like HelloSign, DocuSign, or even Bonsai have one-click signing. The fewer steps, the faster it happens.

    2. Send at the right moment - right after a call when they're excited and committed tends to work better than "I'll send it later."

    3. Set expectations upfront - "I'll send over the agreement now - once you sign we can get started Monday" creates soft urgency without being pushy.

    4. Don't chase forever - if it takes multiple follow-ups, that's often a signal about their commitment level. Sometimes the slow sign is telling you something.

    The PDF-and-pray method creates too many places for things to stall. Making the signature process frictionless usually cuts the back-and-forth in half.

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