Business owners and entrepreneurs frequently have to negotiate- with everyone from clients and customers to service providers. And since sometimes, it’s just as important to learn what not to do, we have asked our contributor network of business owners, experts, advisors and entrepreneurs to share their insights regarding the worst business negotiation mistakes that they’ve experienced. Their answers are presented below in no particular order.

You may notice some similar ideas listed, but I kept them separate, as something in the way one is framed may resonate differently with you.

1. Just SHUT UP

The worst negotiation happens when after you succinctly make your point, you keep talking.
Thanks to: Haralee Weintraub of Haralee.Com Sleepwear.

2. Don't Work For Free!

I've seen people within my business of being an author agreeing to work for next to nothing and thus, perpetuating the expectation that writers work for free- for exposure.

Exposure doesn't pay the mortgage!

The worst thing we can do in our negotiation is agree to a price below our worth!
Thanks to: Warren Bobrow of Cocktail Whisperer.

3. The Smell of Desperation

The opposing side can tell when you're desperate. It's communicated in your word choices and your body language. Everything about you gives off the smell of desperation. And unfortunately, your anxiety is a license for your opponent to take advantage of you.

Instead, pretend that you have a cool few million sitting in the bank and you're perfectly willing to walk away from this deal. Now, you've got some leverage!
Thanks to: Susan Greene of Greene Marketing, LLC.

4. He Who Speaks First Loses

In the art of negotiation, he who speaks first loses. Sometimes in our excitement or eagerness to close a deal, we often do not allow the other person enough time to consider the offer or to get back to us. We call and give in or take less than we would have received if we would have just waited for the person to respond. Eagerness can often come across as desperation. Wait for them to come to you and you'll have the upper hand.
Thanks to: Sharifah Hardie of Ask Sharifah.

5. Give Me Something to Work With

As an executive recruiter, I am negotiating all the time with candidates and clients. One of the biggest and most frustrating mistakes I see are people refusing to share data related to the negotiation. They think not revealing something puts them in a better position. The opposite is true. Why would my clients want to hire someone that hides important information? How can I bring both parties to a deal that makes them happy if one won't be straightforward? Negotiation is a discussion!
Thanks to: John Paul Engel of Knowledge Capital Consulting.

6. Impatience

When negotiating a contract or a deal, NEVER BE IMPATIENT.
Thanks to: Jacob Singer of Regnis.

7. Free Samples

Free samples work great to lure people to a mass-produced product or to a highly elastic service, (such as SAAS). But agreeing to provide free samples of editing, writing or translation is just stupid.

On the plus side, I learned my lesson.

Now, if somebody asks for a sample before agreeing to a full book project, I happily offer to provide them $100 worth of samples. Serious clients will pay for their samples. Tire kickers will evaporate. Both results are a blessing.
Thanks to: David Leonhardt of THGM ghostwriters.

8. Emotional Appeals

I am often in negotiations with various IT vendors for business services and there is nothing that turns me off to contracting more than when a negotiation strays from pure business considerations. There is no more unappealing a strategy than when people use purely emotional, weak or tangent considerations as a tactic in a negotiation. The ability to know your leverage, value and optionality of choices during a negotiation is usually the key to employing a winning negotiation strategy.
Thanks to: Matthew Reischer of Legal Advice.

9. No More Threats

I thought I was a leading distributor for a manufacturer in the textile industry. During a purchasing meeting with the President of the company, I threatened to walk away from his company and find another supplier.

Little did I know, I needed this vendor more than he needed me.

The next day, I returned the President’s office and ate some Humble Pie.
Thanks to: Bob Shirilla of Simply Bags.

10. If You Build it, Will He Pay?

I'm regularly asked to quote publishing a book wherein there are no set specs. It's a dangerous road, but one on which many businesses have to travel in order to secure business. I have made my share of mistakes with negotiations, but here is my most urgent advice:
1. If he says he isn't picky, he is.
2. If she says she is easy-going, she isn't.
3. If he says he doesn't ever want it to come down to money, it always will.
Always build in contingencies for when they change the game on you.
Thanks to: Lisa Pelto of Concierge Marketing Inc.

11. Know When to Fold 'Em

Rule #1 = Always plan BEFORE you are IN the negotiation. Walking in without a strategy is suicide. Have a very clear line in the sand - whether it's the rock bottom fee you'll accept or service concessions that are too expensive to provide. Figure out your ideal price point and then, start negotiating from a percentage higher so that you'll have some room to negotiate. Go for "win/win" and you'll have the basis for a long term business relationship. Nobody wins if one of you loses!
Thanks to: Elene Cafasso of Enerpace Executive Coaching.

12. Negotiation: Win-Win or Lose?

When it comes to negotiation, knowing your self-worth and what you bring to the table should always remain top priority.

Over the past few years, I have noticed that negotiating and lowering prices usually does not bring about a win-win situation. When you lower your prices to get a customer, it often results in being unappreciated, devalued, and can also leave you without enough budget to cover the expenses of the project.

Hold out for those who will appreciate your worth and expertise.
Thanks to: Amore Leighton Black of Apples & Oranges Public Relations.

13. Promise What You Can't Deliver

I have seen some people who are so involved with a business negotiation that they simply start to promise things to a prospective client that are well outside of the realm that they can deliver. Make sure that you always represent yourself and your products and/or services accurately, so that when you win a client, you can perform the job above and beyond their expectations rather than leaving them disappointed and marring your reputation as a service provider.
Thanks to: April O'Leary of April O'Leary, Business Coach.

14. You Can Always Eat Tomorrow!

Putting value on your creative work and time is very important. I have, at times, offered huge discounts on work and then realized I'm working for $4 an hour. The client that wants a super discount is almost always never happy with the work. These same clients are also often difficult to deal with. This is important to remember when you're just starting out. Bottom line: Don't Be Hungry. There's another gig around the corner. Spend the time looking for a great client. That's better than $4 an hour.
Thanks to: Mark Alyn of Mark Alyn Communications, Inc.

15. Don't Do It!

I believe one of the worst mistakes people make when negotiating is to focus only on winning, without enabling the other party(ies) in the negotiation to "win" too.

The best deals are those where all parties feel as though they "won", giving up what they care the LEAST about and getting what they MOST care about.

Provide those across the table from you with a win and you win too!
Thanks to: Stephanie Hackney of Branding Masters, LLC.

16. Negotiating Mistake to Avoid

One of the biggest mistakes business owners make when negotiating a deal is not putting it in writing. Writing out the terms and conditions that all parties involved can agree to and sign off on is a crucial aspect of any transaction. Having a signed document can help to eliminate potential issues in the future. All parties involved will know the extent and/or limitations of the negotiated deal. This written document will help to save time, money, and most of all, provide peace of mind.
Thanks to: Karlene Sinclair-Robinson of KSR Solutions, LLC.

17. Never Accept the First Offer

I think people tend to sell themselves short when in negotiations and take the first offer that is given to them. Maybe it's because they think that's the best that they can get and are afraid to counteroffer. That's why you are in a negotiation- to negotiate!
Thanks to: Eric Knight of Eric Knight Online.

18. Bargaining Power of the Team

A recent mistake that we made was sending in a team of junior marketing managers to an important client meeting without explaining to them the limit and extent of their bargaining power. On the spot calls have to be made in certain situations and if the team is not clear on how much they are allowed to deviate, they tend to make unrealistic concessions to win over the client. If the decision has to be revisited at a later stage, the client sees it very negatively and not as an honest mistake.
Thanks to: Srajan Mishra of TSI International.

19. A Client’s Mistake

Years ago at Mustang Marketing, we worked with a large client who had one rule in regards to negotiating. No matter what was originally submitted as a proposed budget, it had to be cut by 20 percent. No more, no less.

This was a silly, arbitrary rule and we found ourselves in a tough situation, because, at Mustang, we make it a policy to give a fair number upfront and then hold to it.
Thanks to: Scott Harris of Mustang Marketing.

20. Don't Forget the Small Stuff!

We do a lot of contracts with major studios and sports leagues and the biggest negotiating mistake is getting so wrapped up in the big points that you miss little details that can really come back to bite you. The worst mistake we ever made was reaching an agreement with a major client over a licensing deal, percentage, guarantees, etc., and then missing a major detail: The guarantees are for each year...not for the term of the contract. Ouch!! This cost us. Always look at all the details.
Thanks to: Craig Wolfe of CelebriDucks.

21. Avoid Losing Focus on Value

When you are negotiating a service for someone, provide value by fulfilling their requests for assistance. Tailoring your service to their desires can create rapport and positive unforeseen results. For example, if an individual requests training on three social networks, two of which you normally supply and an outside one that you still have stellar competency in, provide the training at an appropriate rate. Valuable content matches consumer desires, and if you can provide it, do so.
Thanks to: Michael Guberti of Teenager Entrepreneur.

22. Shut Your Mouth & Listen

The worst negotiating mistake I ever made was when I came into a presentation so nervous and ill-prepared that I couldn't stop talking. I never stopped. I didn't ask any questions or listen to their needs. I thought I knew what they wanted and since I was so nervous, I didn't engage in any conversation. NO, I did not gain the client. YES, after being excused, I held my head in shame and did not express any emotion during the long elevator ride until I reached my car.
Thanks to: Angel Tuccy of Experience Pros Radio Show.

23. 3 Critical Interwoven Mistakes

The biggest mistake at any level of business is not listening carefully. You must know what the other wants, is willing to do or not do, pay or not pay.

Follow up! How many deals have fallen through for you because you didn't follow up and secure the position or deal you tentatively agreed upon?

Make NO assumptions. If you are unclear about something, ASK. There's no shame in it, and they'll be glad you want clarity, because that's what they want, too.
Thanks to: Angela Treat Lyon of Daring Dreamers Radio.

24. Partners on Different Pages

Just because your partner seems to know what you're thinking in the office doesn't me s/he can really read your mind. Nothing is more painful than watching partners fumble a negotiation because they didn't bother to prepare together and plan who says what. Awkward moments like, "I thought YOU brought the financials" sink deals and ruin brand image. And open disagreement in public sucks the power right out of your negotiation position. Plan-rehearse-debrief. Present a united front and win more.
Thanks to: Karen Southall Watts of Karen Southall Watts.

25. The OH YEAH Contribution...

In any negotiation, a key is being prepared and having done your homework. One negotiating ploy that I use myself and yet despise when others use on me is the technique: "Oh Yeah... can we add this too." Many times when I feel that I have the lead on the negotiations or I am empowered by the talks, I will stretch the requests and ask for more- especially if adding something gets me more in the deal. In defense of this procedure, do your homework, anticipate and plan for additional requests.
Thanks to: Ed McMasters of Flottman Company - Marketing.

26. Seal Your Lips & Seal the Deal

Sealing your lips is an awesome deal closer I've been using all of my life, however, I really found the power in listening, as an entrepreneur, once I studied the great Brian Tracy. Too many business or sales people use too much of their energy trying to close deals by dominating conversations with THEIR voice, instead of listening to others intentionally. If you listen, you will always find something in their words to help you close the deal, up-sell them, or save you a whole leap of money!
Thanks to: Quadeera Teart of The Creative Society, Inc.

27. My Dearest Doesn't Like No

As the business owner, I always know that we aren't capable of solving all of the problems. However, to me, working with a customer is always letting them know that you are trying the very best to help and come up with solutions. So, instead of saying no, I prefer giving out an alternative option, some suggestions, another way out, or at least clearly communicating with the customers and letting them know what the limitations are. It's usually the case that they understand or better, accept the alternatives.
Thanks to: Alyna Deng of My Dearest Bridal.

28. Don't Trade/Don't Negotiate

Trading your services for other goods or services pretty much never works out as you hoped, and there is always some imbalance--straight money is always best. If someone is trying to negotiate an exchange of goods or services, chances are they're going to make a horrible client anyway.

A good friend once taught me to never negotiate rates, period. If you have a rate, stick to it. Most clients or customers will respect you for it, and sticking to your guns shows that you're a professional.
Thanks to: Geoff Hoesch of Dragonfly Digital Marketing.

29. Know Your Numbers

Not being able to justify your negotiation position with facts or data is often detrimental to your position in the negotiation. Knowing your numbers prevents subjective opinions influencing the negotiation. It also gives you a clear 'cut-off' point at which it becomes a non-viable proposition financially, mitigating against 'getting a deal done' that ends up being a cost to the business. Web design projects are notorious for scope creep, so we like to have clear facts set out from the start!
Thanks to: Simon Ensor of Yellowball Creative Consultants.

30. Talk Less and Listen More

People often talk too much and don't listen enough. They interrupt the other side before helpful information would have been revealed. People also rush to speak if there is an uncomfortable silence and in their haste, give up costly information. Wait for the other party to speak instead. You only learn about the other side's intentions and goals when you listen to them. Encourage them to talk and eventually, they will say something that will tip their hand or provide you with helpful information.
Thanks to: Tali Raphaely of Armour Title Company.

31. Deception, Games & Lies

In a negotiation, I always assume the person with whom I am engaged is operating in honest good faith. Nothing sours a negotiation faster than when you begin to mistrust the person at the other end of the negotiation. I have been in many negotiations where a party will play games, manipulate and lie, all in pursuit of their negotiation without thinking that they are often obvious in this tact. The use of deceit in a negotiation is an awful approach and may be a basis to kill a deal.
Thanks to: Martin Hess of Flushing Homes.

32. Don't Get Put Against the Rail

If you hear “sign up by Friday and I’ll get you 10% off the contracted rate,” check your calendar. Is it the end of the month or quarter? If so, the rep is against the rails, trying to hit quota or a performance bonus before the end of the marking time frame. It gives you the upper hand, since they’re likely scrambling to close your deal. Be careful getting backed against the rail; prospective clients see you can lower or negotiate terms and will use that to their advantage.
Thanks to: Michelle Brammer of

33. Short Fuse

One of the worst negotiation mistakes our firm recovered involved a leader with an anger management problem. The challenge: an angry leader had picked a fight with a powerful government agency. Unfortunately, this leader had placed the entire company at risk which translated to several million dollars in fines. The near term solution: the Board removed this leader and our firm quickly implemented several layers of recovery. Best practice: extinguish a short fuse before negotiations begin.
Thanks to: Kelly Isley, Author of of Adapt Now.

34. Don't Take the Weak Approach

As litigators, the worst negotiation mistake we have seen is trying to negotiate from a position of weakness. This happens when some of our smaller clients decide to work around us and negotiate directly with the opponent, but this always results in a far worse settlement than if the client avoided getting involved in negotiations and left us to do our job. Once the opponent realizes we're filing legal action and won't take a weak approach in negotiations, it becomes clear that all bets are off.
Thanks to: Nick Iezza of Spiwak & Iezza, LLP.

35. Focusing on Short Term Results

The biggest negotiation mistake that I’ve seen is focusing on short-term results that hurt long-term profits. I became part owner of Liberty Coin Service in 1981. In 1984, both owners attended a convention to purchase inventory. One owner insisted on not purchasing any coins unless they were at a maximum discount. In the process, the price negotiations were protracted and created ill-will. In contrast, I bought coins where the price seemed to be a reasonable discount & negotiations went well.
Thanks to: Patrick Heller of Liberty Coin Service.

36. Never Lead with Price

Never lead with your best price. Defend your listed price with value. Don’t panic when someone challenges your value; shut up and hear them out before you answer. Your customer will tell you how they want to buy if you diligently listen to provide your customer with solutions that build trust and value.
Thanks to: Katie DeCicco of

Have you encountered a business negotiation mistake that wasn’t included? If so, please share it below. And as always, many thanks to everyone that contributed to this article!

And if you would like to become a part of the contributor network and find out about opportunities to contribute to future articles, sign up here: