Negotiate Everything

Two women in conversation across a table

~by Haley Lynn Gray~

Nearly everything in life is negotiable.

That realisation came slowly to me. I was raised to do what I was told, without asking questions and certainly without negotiating over the details. Many women were. You learn early that the polite thing is to accept what you’re given.

At this point I’ve come to the opposite conclusion: almost everything is negotiable. Not everything works out, but the number of things that turn out to be flexible once you simply ask is remarkable.

The things people don’t realise they can negotiate

Price is the obvious one. It’s also the least interesting, because it’s the thing most likely to get a flat no. The rest of the deal is usually far more flexible:

  • Payment terms. Deposit size, instalments, when the balance falls due.
  • Timeline. When you start, when you deliver, how long you have.
  • Scope. What’s included and what isn’t — often a better lever than price.
  • Contract terms. Notice periods, liability caps, exclusivity, who owns the work.
  • Fees. Bank charges, late fees, penalties, subscription rates, renewal prices.
  • Bills. Medical bills in particular are frequently negotiable, as are payment plans for almost anything.
  • Your own rates. What you charge, what you charge for extras, and when it goes up.
  • Working conditions. Hours, location, response times, what counts as an emergency.
  • The form of payment itself. I’ve bartered, traded and swapped services more times than I can count. Money isn’t the only currency, and a trade can be worth more to both sides than a discount.

Very little actually costs what it says on the box.

Most of those never occur to people as negotiable, because they arrive looking like facts. A price on a page looks fixed. A contract clause looks like the law. Usually they’re neither — they’re the other party’s opening position.

You don’t need permission

The thing that took me longest to learn: you don’t have to be invited to negotiate.

There’s no moment where someone says “now you may ask for something different.” You just ask. Politely, clearly, and without apologising for it.

The worst realistic outcome is a no, and a no leaves you exactly where you already were. That asymmetry is the whole argument — the downside is almost always tiny and the upside compounds across every deal you ever do.

How to actually do it

Be clear about what you want before you open your mouth. Not “a better deal” — the specific thing. Thirty days instead of fourteen. Half up front instead of all at the end. The training included.

Ask for something specific. Vague requests get vague answers. “Could you do anything on the price?” invites a shrug. “Could you do it at X if I pay the whole thing up front?” invites a decision.

Know what you’ll trade. Good negotiation is rarely one side simply conceding. Faster payment, a longer commitment, flexibility on timing, a testimonial — all of these are worth something to the other party.

Know your walk-away before you start. The point at which you’d rather have no deal. Decide it in advance, because deciding it mid-conversation favours whoever is more comfortable with pressure.

Be polite and be firm. Those aren’t in tension. The most effective negotiators I know are perfectly pleasant and completely immovable on the things that matter to them.

Then stop talking. Make the ask and let the silence sit. It feels much longer than it is, and filling it is how people negotiate against themselves.

But know who you’re squeezing

Here’s the part most negotiation advice leaves out, and I feel strongly about it.

I watch people negotiate hardest with small business owners — the ones with the least room to give. The independent shop, the solo consultant, the two-person agency. Meanwhile the large companies, whose prices are far more elastic and whose margins are built to absorb it, get accepted without question.

It’s exactly backwards. A big company’s list price is frequently a starting position with a great deal of flexibility behind it. A small business owner’s price is usually the number that lets her pay her people and herself, and every dollar you talk her down comes directly out of her livelihood.

So negotiate hard with the companies built to withstand it. With small businesses, negotiate terms rather than price — timing, scope, payment schedule, a trade — or simply pay the asking price and become the client they’ll move mountains for.

Supporting small businesses is worth doing deliberately, and that includes not grinding them down on price because you can.

The part that’s harder for women

It would be dishonest to pretend this costs everyone the same. Research has repeatedly found that women who negotiate are judged more harshly for it than men doing exactly the same thing.

That’s worth knowing, and it isn’t a reason to stop. It’s a reason to ask in ways that make the penalty harder to apply — anchored to the work rather than to yourself, framed as the standard, and delivered warmly.

Start small

If this feels uncomfortable, pick something with almost nothing riding on it. A subscription renewal. A supplier invoice. A delivery date that doesn’t much matter.

Ask once, politely, and watch what happens. Most people are surprised how often the answer is yes — and how quickly asking stops feeling like an imposition and starts feeling like ordinary business.

If this resonates, you don’t have to figure it out alone.
We host small, thoughtful Round Table conversations inside Women’s Entrepreneur Network where women leaders talk through exactly this kind of challenge.
You’re welcome to join us.

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