How to Use Deadlines in Negotiation Strategies

Law students and young lawyers: setting deadlines matters. I'm not talking about court deadlines here; that should be obvious you need to meet those deadlines. I'm talking about deadlines with opposing counsel, particularly when you're litigating and even more particularly when engaged in settlement discussions. At a certain point, OC is going to start dragging their feet and you need to light a fire under them. Maybe they blame the client, or workload, whatever...but you have to answer to your client who rarely wants to see the meter keep running on endless settlement negotiations while the discovery calendar ticks away. So, be reasonable. Be accommodating. Be willing to compromise. But at some point, you need to tell OC: this is a deal-breaker, we've spent too much time on this and the value of resolution is diminishing. Either we have a deal by X, or we're going back to litigation posture. *And then you stick to that deadline.* 9 times in 10, you'll get the settlement done. And the 1 time you don't, your adversary will learn you mean what you say, and that "FOFA" is not the best legal strategy.

Sellers: do not lose control of your deal! The #1 rule in B2B sales? Time kills deals. I’ve built 8-figure businesses and seen 100s of deals die. Even when I was told: 'Wow! This product is awesome.’ 'This is the perfect fit solution.’ "I am so bought in.’ Why? The seller has 0 urgency. There is no hard deadline. They fluff it! So here are 3 ways to get deals OVER the line... (WITHOUT being pushy): 1. Make inaction expensive. Stop “checking in.” Stop waiting. Instead, quantify the cost of inaction: “I ran the numbers - this will double the number of proposals your reps can send in six months.” Create stakes → incentivise speed. 2. Set a hard deadline. Never ask: “When do you think you’ll be ready?” Say: “If we close by March 15, you’ll be ready and seeing results by March 31. After that, we’re looking at next quarter.” Leverage urgency. Deadlines drive action. 3. Kill objections before they kill momentum. Legal always slows things down? Get ahead! Say: “I know legal needs to review this - let’s book a 10-minute call now to avoid delays.” Control the process. Or watch deals die in limbo. TAKEAWAY: Deals don’t close themselves. They rot and decay. Your job isn’t to aggressively "sell". It’s to STOP THE DECAY! Read those last 4 lines again. Am I right or wrong?

Do not send out a contract before first discussing "redline deadlines" with your prospect. Here's how I do it: 👨 Me: "Great, we're really excited to be working with you. It's going to take me about 45 minutes to assemble your contract and get all the approvals from my end. I will send your contract before the day ends. If I get you the contract by EOD, when should we expect to receive redlines back from your team? I'll want to give my counsel a heads up." (Explaining the work it takes YOU to get them a contract gives you the right to then push THEM to give you an explicit response date. Use the reciprocity principle here) 👨🏻 Prospect: "We're pretty backed up on contracts right now, but if you send it today, we should be able to respond by the 13th." 👨 Me: "Cool. If you can get me first cut of redlines by the 13th, our team is pretty fast at turning things around. If you get us your team's first redlines by the 13th, we'll be able to return a response by EOD on the 14th. If we do that, would your team be able to finish 2nd cuts of redlines by the end of the week, so the 17th?" (Don't stop at first cut of redlines. Tell them when they should expect YOUR response and then ask about 2nd cuts from their end.) 👨🏻 Prospect: "I obviously can't promise, but that does sound doable." 👨 Me: No worries. If you are able to get us a response by the 17th, we'll be able to review over the weekend and get you our response first thing on Monday, which should expedite things considerably." 👨🏻 Prospect: "Yup. I'll definitely push the team. We don't want this to linger forever." (It's always OK to push your prospect if you explain why it's in their best interest) 👨 Me: "Great - and if we find that we need to setup a call between your legal team and ours to hammer things out, we can do that at any time. What I'm going to do from here is document the timeline we just discussed and send it to you. I'll also send over some calendar reminders just so we have the timeline in front of us." (Make it IMPOSSIBLE for your prospect to forget the timeline they've committed to. I send a written Recap + Calendar Invites for each of the deadline dates) ___ Notes: 1. If their redline timeline isn't consistent with other timelines (their intended go-live date or an agreed upon commercial incentive) this gives you the right to push the redline timeline harder. 2. I like to proactively suggest a call between legal teams. That usually moves things faster than going back and forth on email. 3. Once you've discussed legal review timelines, I like to pre-schedule their kickoff call as further incentive to move through redlines in timely manner. 4. Want my full guide to driving timeline in sales? Click subscribe to newsletter in my header and you can have it for free :)