How to Use Timing to Influence Decision-Making

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)

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?

Creating deal urgency in a very uncertain time. Given the macroeconomy right now [gestures at headlines], I’ve heard stories of companies putting purchasing decisions on hold, and who can blame them? As a result, it’s harder than ever for the founders and sellers out there trying to close deals on a given timeline. If you're trying to move things along without sounding pushy, here are a few tactics I’ve seen that can help speed up deal urgency: 🕵️ It starts at the beginning – with great discovery I feel like every sales tip starts here—but it really matters. Do the work up front to understand if this should be a good deal, and all the why behind that. → Example: Ask early, “What happens if this doesn’t get solved this quarter?” 📅 Tie it to something real Deals tend to move when there’s a reason to move. A renewal, a board meeting, a project kickoff—anything time-bound that’s already on their calendar. → Example: “If we start onboarding in May, you’ll have live results by your Q3 planning cycle.” 🧩 Make it easy to start If a full rollout feels like too much, suggest a smaller step—pilot, limited scope, phased launch, whatever keeps things moving. → Example: A 30-day paid pilot with one team can be way easier to approve than a company-wide contract. 👥 Involve decision-makers early (& gently) If someone senior will need to sign off eventually, try to get them involved sooner. Not to add pressure—just to make sure they’re aligned before everything’s baked. → Example: A 10-min intro call between your exec sponsor and theirs can save weeks later. 🧘♂️ Don’t be too chill “We’re flexible on timing” sounds nice, but it gives the other side permission to wait forever. Instead, share a clear (but reasonable) path forward. → Example: “We’re holding onboarding slots for late May—can you commit to that?” ❤️🔥 But also don't be too intense. “Hey just checking for an update here” texts every few hours when your decisionmaker has told you they're working on it risks alienating them. See tip #1 and ask yourself if you've really found a pain to solve that merits this level of pushiness. You don't want to risk the deal entirely just to try to close it at the end of the month. → Example: “I don't want to pester you, so please let me know if you have five minutes in the next few days to discuss finalizing this partnership.” Would love to hear what’s working (or not) for others. How are you trying to drive urgency in your deals these days?