Timing Strategies for Effective Negotiation

Next time you hear an objection, take a pause and isolate whether it's a current state or future state objection. Current state objections = cost of inaction isn't big enough to warrant action. There may be pain, but the pain of same is tolerable. Ex: "Let's revisit this in 2026". Future state objections = concerns with perceived risk of buying/implementing the solution. Prospect agrees the pain of same is intolerable, but has concerns re: whether this is the right solution or right partner. Ex: "We're going to need more time to evaluate the options internally before we schedule the next call." Current state objections and future state objections are very different problems to solve in the mind of the buyer. Current state objections = is this problem is worth solving, and worth solving now? Future state objections: is this solution, from this vendor, the right way to solve the problem? Pitching ROI/case studies to a current state objection doesn't align with the root cause of the objection. Pitching COI to a future state objection doesn't align with the root cause of the objection. Bonus: Once I started doing this, I counted how many objections were rooted in current state vs. future state. In December 2020, I noticed I was heavy on current state objections. It helped me see that I was jumping to solution WAY too quickly (likely out of a fear of missing my target and acting desperate to rush the sales process). I wasn't framing the cost of inaction. I was playing solution show and tell. Give this a try. Not only will it help you address the RIGHT problem with your buyer, but it teaches us a lot about where we may be rushing our process!

A sales director just told me how his team lost their biggest deal of the year. "Everything was going perfectly. Amazing discovery calls, perfect product fit, champion was advocating for us, budget was confirmed. Then in our final meeting, the prospect said: 'This all looks great. We just need to think about it.'" His rep's response? "Sure, no problem. Take all the time you need." The deal died two weeks later. Here's what that rep fundamentally misunderstood: When prospects say they "need to think about it," they're not asking for time. They're asking for help. What the rep should have said: "I totally understand you need to think about it. Help me understand what specifically you need to think through…" When we dug deeper into this situation, we discovered the real issue: The prospect was worried about implementation timeline conflicting with their busy season. A 5 minute conversation about phased rollout options could have saved the deal. But because the rep gave them "time to think" instead of clarity on their concerns, the prospect's worry festered into a no-decision. Here's what "I need to think about it" really means to your prospects: → "I have an unspoken concern I haven't voiced" → "Something doesn't feel quite right, but I can't articulate it" → "I need more information but don't want to seem uninformed" → "There's a stakeholder objection I haven't mentioned" → "I'm not convinced this is the right timing" The best sales teams understand this and train their reps to respond accordingly: "What specifically concerns you most about moving forward?" "What questions do you think will come up when you discuss this internally?" "What would need to be true for this to feel like an obvious yes?" "What's the biggest risk you see in making this decision?" Stop accepting "I need to think about it" as a natural end to your sales process. Train your team to treat it as the beginning of their most important conversation. Remember: Confusion kills deals. Clarity closes them. — Want to hear a top sales VP sharing how he blows out sales targets? Go here: https://lnkd.in/gH7amsci

I run the "5 Minute Drill" at the end of every sales call: 🟢 Ask: How are you feeling? Should we keep exploring working together? There is zero sense in trying to talk timeline or next steps if the other person isn't bought in to continuing to explore. Pulse check their sentiment FIRST. Consider phrasing it like this: "Gut reactions - how are you feeling?" "What did you think? Worth exploring further?" If they feel good, move to the next question (below) If they don't feel good, you've gotta address their concerns first. ___ 🟢 Ask: Could you talk to me about timelines? Only once they feel good about continuing to explore, then you can talk timelines. You should understand timeline BEFORE you talk specific next steps. It's hard to recommend the proper next step if you don't understand the urgency (or lack thereof) If they need this implemented in a WEEK, you're probably gonna need to move faster than if they want to implement in 6 months. Best if you can tie timeline to something that's happening in THEIR world, but if you don't have that, you might say something like: "Talk to me about how you're feeling about timelines for something like this" ___ 🟢 Recommend: Specific Next Step(s) Once you understand timing - make a recommendation for how to proceed. Can be as simple as saying "What I'd recommend we do next is..." Can be as complex as reviewing a mutual action plan together. You should always make a recommendation for how to proceed- your buyer is not a professional buyer and it's your responsibility to help guide them. It's OK if they disagree with your recommendation, it means they're at least thinking critically about their evaluation process (and gives you a great chance to run some discovery about that process)

I hear this all the time from salespeople. The stress and struggle with meeting customer deadlines. During a session I delivered last week on forecasting and pipeline accuracy, I asked this sales team if this is an issue for them. Every hand went up.   When I asked why, the floodgates of assumptions opened.   🌟 Clients are demanding. They want everything yesterday. 🌟 The first responder wins. 🌟 I need to get this to them ASAP or I'll lose their business. 🌟 I have to drop everything just to hit a deadline, sacrificing my other responsibilities and my personal life.   👉Consider this: What if most of the stress you experience is self-imposed? 🤯   For example, you have a customer who needs a proposal. "The customer is expecting it yesterday!" you assume. You panic, as you look at your calendar for the week.   "When am I going to get this done?" The overwhelm takes over.    Here's the irony about managing and meeting customer expectations.   The customer didn’t set the deadline. The salesperson did! And all of this is based in the FEAR of loss and the ASSUMPTIONS they think the customer wants.   Rather than assume what they want, have them create the deadline! Here's the talk track to get your time back, eliminate the problem of overcommitting and meet expectations every time.   You: "Dear customer, when is the latest you need this proposal by?"   Customer: "Next Thursday should be fine, no rush, as I’m traveling."   You: "Okay, so if I get this proposal to you by next Thursday, when would you have a chance to review this?"   Customer: "I'll need to meet with the two other stakeholders to review this. And that won't happen until the following Tuesday."   You: "Great, let’s go ahead and schedule our next conversation after your meeting, so I'm being responsive for you and we keep the momentum going. What works for you?"   #sales #quota #proposals

Recruiting isn't about closing fast. It's about staying close. But here's the challenge: How do you follow up long-term without annoying the candidate? How do you stay on their radar… without feeling like a telemarketer? You ask for permission, and you earn the right to stay in the conversation. Here's a simple 3-part framework I teach leaders to use: 1. Acknowledge the timing "I totally get that now may not be the right time to make a move." When you acknowledge their current reality, you build trust. 2. Ask for alignment "Would it be okay if I stayed in touch over the next few months, just to keep the conversation open?" This shifts follow-up from "nagging" to agreed-upon access. 3. Set the tone for future value "I'll make sure anything I send your way is relevant to where you're headed, not just where you are today." Now you're not a recruiter. You're a future-focused partner. Bonus tip: Keep it human and low-pressure. Text updates. Quick voice notes. A win your team just had. A leadership thought that made you think of them. The goal isn't to sell. It's to stay worth replying to. Because the best candidates aren't always ready on the first call. But they do remember who stayed connected the right way. Play the long game, with permission, not persistence.

You got an offer from Amazon — but you’re still mid-process with Apple. What now? This is one of the most common scenarios I coach clients through. After 350+ tech negotiations, here’s the playbook I recommend: 1/ Delay Amazon (without losing momentum) → Show genuine enthusiasm → Ask for more time to make a thoughtful decision Script: "Thank you again for the offer - really excited about Amazon and this team. What I'm struggling with is how I can make this life changing decision in 48 hours? If the deadline could be extended, that would give me the time I need to make an educated decision here." 2/ Speed up Apple (without sounding threatening) → Reiterate strong interest → Let them know you’re other opportunities are ramping up (avoid saying "I have another offer" unless you're ready to share all the details) → Frame it around wanting to make a fully informed decision Script: “I’m very excited about the opportunity at Apple and have loved meeting everyone on the team. I want to let you know that some of my other opportunities are ramping up and I'm a little concerned around timelines. If next steps could possibly be expedited, that would greatly help me since Apple is one of my top choices." This approach signals that you’re a strong candidate — and that you’re managing your options professionally. It also gives both companies the clarity they need to act. The best negotiators don’t just juggle numbers — they manage timing just as strategically. Have you ever been in a timeline squeeze like this? What did you do?

Here's exactly how I structure my follow-ups to stop deals from slipping or ghosting at the last minute. Buyers ask themselves 5 crucial questions before they spend money. So we match our follow ups to each different question of the buying journey. The questions: 1/ "Do we Have a Problem or Goal that we Urgently need help with?" Follow up examples: Thought Leadership emphasizing the size / importance of the problem. Things like articles from Forbes, McKinsey, HBR or an industry specific publication. Screenshots, summations or info-graphics. NOT LINKS. No one reads them. 2/ "What's out there to Solve the Problem? How do Vendors differ?" Follow up examples: Sample RFP templates with pre-filled criteria. Easy to read buying guides. Especially if written by a 3rd party. 3/ "What Exactly do we need this Solution to do? Who do we feel good about?" Follow up examples: 3 bullets of criteria your Buyers commonly use during evaluations (especially differentiators.) Here's example wording I've used at UserGems 💎: "Thought you might find it helpful to see how other companies have evaluated tools to track their past champions. Their criteria are usually: *Data quality & ROI potential *Security (SOC2 type 2 and GDPR) *How easy or hard is it to take action: set up/training, automation, playbooks Cheers!" 4/ "Is the Juice worth the Squeeze - both $$$ & Time?" Follow up examples: Screenshots of emails, texts or DMs from customers talking about easy set up. Love using ones like the Slack pictured here. Feels more organic and authentic than a marketing case study. 5/ "What's next? How will this get done?" Follow up examples: Visual timelines Introductions to the CSM/onboard team Custom/short videos from CSM leadership When we tailor our follow ups to answer the questions our Buyers are asking themselves - Even (especially!) the subconscious ones Our sales cycles can be smoother, faster and easier to forecast. Buyer Experience > Sales Stages What's your best advice for how to follow up? ps - If you liked this breakdown, join 6,000+ other sellers getting value from my newsletter. Details on my website!

Truth Number 1: Time kills deals.  Truth Number 2: The party who is least concerned about time often has the most leverage. In a negotiation, time is a massive two-edged swords in a negotiation. Nearly every single in flight deal that I was involved in last week leveraged an EOQ lever. Do I think this is a right and effective play in some cases? Absolutely. Do I think it’s unnecessary and can do more harm than good in other cases? Also absolutely. 2 weeks ago a salesperson (and a friend) called me up. They wanted some advice on a deal they were working on. They explained that they had deployed the EOQ lever and the stakeholder still hadn’t committed and in fact was asking for more. Here’s what I coached him to say: “Hey Bill - Previously I had mentioned that the additional 8% concession was contingent upon a signature by the EOQ. While I think signing by the 31st would certainly be ideal so that we can have the biggest impact for your team in Q2, I also understand that you have a lot going on and I don’t want you to feel rushed. Bottom line, I talked to my leadership and got them to agree to remove the contingency.  We’ll honor the 8% whether you sign this quarter or next. At this point, we feel really good about the proposal on the table. The ROI should be really strong and the SLA reflects that. The team seems really excited. Let me know if there is anything else you need from me.” In this case, Bill responded: “Wow, thanks. I actually think we can get it done but I appreciate the flexibility.” This salesperson texted me last Friday that the deal got signed. I’m genuinely not sure it would have (without additional concessions) if the rep didn’t take away the contingency. Time kills deals. Totally get that. But over-rotating on urgency can in some cases destroy leverage. You intend to put the pressure on the buyer but sometimes we’ll flip it right back on you because it’s so obvious the seller wants the deal by EOQ.  And often times, it can chip away at ACV unnecessarily. Again, each situation is different but it’s a good reminder that there are two sides of the sword. Wield it wisely. (And yes, the name of “Bill” has been changed. Isaiah has convinced me that when changing the name of the prospect, you should always use the name Bill. Not sure why, but I trust his judgment). 

We met with the CFO twice, had a verbal agreement, and he asked us for 1 week to finalize between 2 options. A week passed... and nothing. He asked for another 2 weeks. The problem remained: This wasn’t budgeted for and it’s a big investment. What we did not do: Try to hold the timeline against them. 𝗪𝗵𝗮𝘁 𝘄𝗲 𝗱𝗶𝗱 𝗱𝗼: 1. Met with our champion(s) and tried to deeply understand the ‘why’ 2. From there, recommended to take a step back and address their #1 challenge of total cost 3. Partnered in looking through the rest of their current tech stack, and seeing where else we could help provide efficiencies 4. Uncovered they were very unhappy with another adjacent tool and had a renewal within 6 months 5. Created a 3 week evaluation plan to see if we could replace that solution 6. Ran through that evaluation - discovery call, 3 demos, reference, scoping call - and gave them the confidence we could From there, we asked for the CFO’s time with our champions. We built out a cost table that showed the savings and consolidation we would be able to provide. And included in an additional financial incentive in exchange for a longer commitment. It grew our deal size by 30%, saved them money long-term, and got our champions access right away. Negotiations aren’t a battle into who can win the deal. It’s about creating a big win for your buyer. P.S. My 7 rules for negotiation on my blog here: https://lnkd.in/gGAvwSZB

Ever had a great first meeting, only to watch the relationship fizzle out? You're not alone. Here are some resources for follow-up success: 1. The 24-Hour Thank-You Blitz Send a personalized note within 24 hours of your meeting. Reference specific points from your conversation to show you were paying attention. Subtly hint at future engagement without being pushy. 2. The Value Bomb (Week 1) Within the first week, share something relevant to their interests. This could be an article, event invitation, or impact story. The key is to prove you listened and care about their passions. No ask here, just pure value. 3. The Engagement Invitation (Weeks 2-3) A few weeks in, invite them to experience your mission firsthand. Think site visits, volunteer opportunities, or exclusive events. The focus should be on involvement, not money. 4. The Impact Showcase (1 Month Mark) At the one-month mark, share a specific story of your work in action. Connect it to the interests they expressed during your meeting. This is your chance to show how supporters like them make real change happen. 5. The "Round Two" Proposition (6 Weeks Post-Meeting) Around six weeks after your first meeting, suggest a follow-up conversation. Frame it as an opportunity to share updates and seek their input. Offer specific meeting options to make it easy for them to say yes. Remember: Every interaction is a chance to deepen the connection. Keep it donor-centric, valuable, and personal. P.S. What was your longest every follow-up attempt that ended in a gift?