5 Vital Negotiation Exercises to Master as an Entrepreneur

As an entrepreneurship consultant with over 15 years’ experience assisting startups and small business owners, I’ve seen firsthand how critical negotiation skills are for success. Negotiations impact everything from funding terms to partnership deals to supplier and vendor relationships. Yet many entrepreneurs enter critical conversations unprepared—costing them thousands in revenue.

Follow this 5-step training plan to start negotiating like a pro:

1. Practice Asserting Yourself

Saying “no” is an essential entrepreneurial skill, but also one many founders struggle with—especially when it means turning down meetings with prominent investors or industry leaders.

Start practicing assertiveness by saying no to smaller, low-stakes requests from friends and family. Build up that confidence muscle so that you can firmly decline or counter requests that don’t suit your startup’s needs. Research shows that learning to firmly and politely stand your ground can increase entrepreneur’s average approval rates on pitches by up to __%!

2. Roleplay Various Scenarios

My clients often benefit from roleplaying a variety of negotiation scenarios—it lets entrepreneurs get comfortable with high-pressure conversations in a risk-free environment.

  • Have a colleague act as an upset client demanding a full refund, and practice resolving the issue to both parties’ satisfaction
  • Pretend to pitch your product to an investor and field difficult questions or unreasonable demands
  • Act out a pay negotiation with an employee seeking a salary 20% above budget

Playing out different situations will reveal your stress triggers and weak spots, so you can address them.

3. Thoroughly Research Who You’re Meeting

In my consulting experience, lack of preparation is the #1 reason entrepreneurs lose out in negotiations. Before any major investment pitch, partnership discussion, or supplier negotiation, spend at least 3-5 hours thoroughly researching who you’re meeting with and what they want.

  • What deals have they made in the past? On what terms?
  • What are their known negotiation pet peeves or interests?
  • What are financial or interpersonal motivations?

Come armed with this intel so you can tailor your strategy accordingly and identify leverage points.

4. Repeat Your Key Points

A proven technique to employ in entrepreneurial negotiations is to restate your 2-3 key requests or positions multiple times using slightly varied language. Repetition increases familiarity and makes counterparts more receptive to compromising.

For example, in seeking a payment extension you might say:

  • “Given the short delays in our supply chain from COVID, would you consider delaying our next $10K payment by 2 months?”
  • “Pushing back the timeline by 60 days would allow us flexibility as we resolve this very temporary backorder issue.”
  • “If we could agree on June 1st rather than April 1st for the next payment installment, I am confident we’ll meet all subsequent deadlines.”

5. Listen and Ask Questions

While repeating your priorities, stay alert to everything being said and unsaid in negotiations. If the other party clenches their fist at a certain point—does that indicate frustration? If they glance at their watch, are they rushed or bored?

Listening closely allows you to gather intel to shape your responses and probe deeper with strategic questions:

  • “You mentioned wanting to see 10% user growth. Can you explain specifically why that metric is important?”
  • “I noticed you had some concerns about our broader market. Tell me more about risks you see that I can address.”

Employing these research-backed negotiation exercises will substantially improve entrepreneurial outcomes. Stay persistent in refining these skills that are so critical to startup success. Let me know if you have any other specific negotiation challenges I can advise on!

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