"Creating" Urgency in Sales Deals

Intro

I’ve lost more deals to time than to competitors. In B2B sales, time kills. The longer a cycle drags on, the greater the risk of losing momentum, losing budget, or losing the client altogether.

For deals in the 50k to 300k range, most salespeople are told to expect a six-month journey. Some stretch to nine or even twelve. But what if that wasn’t necessary? What if you could consistently close a 100k deal in three months or less?

I know it’s possible because I’ve done it myself, and I’ve seen my teams do it repeatedly. We achieved it not by luck or shortcuts, but by applying urgency in a deliberate way. And urgency here doesn’t mean pressuring the client or dangling false discounts. It means guiding the deal with clarity, momentum, and precision so the buyer sees value quickly and wants to move forward.

Of course, external factors play a role. A must-have product moves faster than a nice-to-have. A seasoned rep can lean on credibility and past stories more than a junior can. RFPs, regulations, or public-sector structures naturally extend timelines. And the trust your company already has in the market will always influence speed. These are realities — but they are not barriers. Even with a product that seems optional, even as a younger rep, even without a long track record, you can compress cycles dramatically if you apply the right tactics.

In this chapter, I’ll share five of the most effective tactics I’ve learned. They are practical, repeatable, and proven to cut months off a deal cycle.

The first and most important tactic is uncovering a strong use case. Most reps stop at surface-level discovery. They hear a “yes” to a challenge and rush into a demo. That’s not enough. To accelerate deals, you must slow down here and dig deeper. When a client says, “Our managers don’t have time to coach reps,” you must explore what that really means. Do the reps keep using the same tactics year after year? How is that affecting revenue? What’s the cost of inaction? When you uncover urgency in the problem itself, you transform the conversation from interesting software to a must-solve business issue.

Once urgency is uncovered, you need to protect momentum. That’s where the second tactic comes in: booking the next meeting immediately. Time lost between meetings is one of the biggest killers of velocity. If you let the client “get back to you,” weeks vanish. Secure the next step before the current call ends, and you’ll save months over the course of a deal.

The third tactic is running workshops instead of presentations. Traditional sales decks leave prospects nodding politely and then disappearing to “discuss internally.” Workshops flip the script. They make the buyer an active participant, aligning stakeholders around shared outcomes and collapsing weeks of indecision into a single session.

Fourth is developing sales process acumen. Top reps don’t just know their product. They know their process inside out and how it maps to the buyer’s journey. That’s what lets them propose the right next step with confidence, rather than waiting for the client to figure it out.

The fifth tactic is asking for referrals and introductions. Every meeting is an opportunity to expand the conversation. Too many reps skip it or ask poorly. When you prepare and ask the right way, warm intros open doors instantly and collapse timelines by bringing trust into the room from day one.

Finally, beyond these five, there are a set of bonus tactics — advanced plays that can shorten deals even further. These include how to approach the economic buyer from the very first touch, how to strategically connect executives across companies, and even how to use a “hypothetical discount” to test urgency without ever lowering your price. We’ll get to those later in this chapter.

Each of these tactics accelerates the cycle on its own. Together, they create the discipline and momentum that allow you to close six-figure deals in three months. In the sections that follow, we’ll go deeper into each tactic with stories, examples, and practical steps you can apply immediately.

Tactic 1: Uncovering a Strong Use Case

Most salespeople assume their clients already know their challenges. They think the buyer has already calculated the cost, recognized the urgency, and just needs to see a solution. That assumption is wrong. In reality, most buyers have never quantified the size of their challenge—or even realized that it exists.

I know this from experience. In my first three years in software sales, I didn’t ask a single question about a client’s challenges. Not one. I jumped straight into my demo, assuming the client already understood their pain points. The truth was, they didn’t. And I wasn’t helping them discover it either.

Why clients rarely know their real challenge

In most cases, your prospects are not problem-aware. They are not sitting at their desk calculating how many hours their managers spend coaching reps, how much CRM inefficiency costs them, or how many deals they’re losing because of inconsistent processes. That’s invisible to them—until you shine a light on it.

For example, when we started selling AI tutors for sales reps at Taskbase, we knew the math: five team leads each spending 30% of their time on coaching meant 1.5 FTEs—more than $150,000 annually—for just 30 reps. Clients never calculated that number. They didn’t see “managerial coaching time” as a cost center. They weren’t problem-aware. But once we showed them, urgency appeared.

Why open-ended questions don’t work

Traditional discovery questions like “What’s your biggest challenge?” or “What keeps you up at night?” often fall flat—especially in outbound meetings. Prospects answer with something vague, and the conversation stalls.

At Unique, when we sold a recording tool, I’d ask, “What is your challenge?” Prospects would say things like, “Hiring reps is really hard right now.” Relevant? No. Actionable? Not at all. The problem wasn’t that they didn’t care—it’s that my question was too broad.

A tactical approach: guided discovery

Instead of asking open-ended questions, guide your prospect by giving them a menu of likely challenges. Then dig deep into whichever resonates most.

Here’s what it looks like:

“From what we’ve seen, companies like yours typically face one of three challenges: managers don’t have time to coach reps, reps don’t apply coaching consistently, or leaders lack visibility into skill development. Which of these feels closest to your reality?”

Once they pick one, the work begins. The average rep jumps into a demo at this point. Top performers keep digging.

The LinkedIn example: going deeper than 99% of reps

Here’s a real example I posted on LinkedIn that resonated strongly.

The discovery starts simple:

Salesperson: Why are you taking the time for this meeting?

Prospect: We’d like to learn more about your tool. We want to make our salespeople’s lives a bit easier, reduce admin effort, and improve conversion rates.

At this point, 70% of salespeople stop. They’re satisfied and move to the demo.

But the stronger rep digs further:

Salesperson: What admin tasks specifically?

Prospect: Reps spend too much time entering data into the CRM, and they often can’t follow up after meetings. That leads to lost deals.

Now 20% of reps stop here. But the best keep going:

Salesperson: Besides time lost, what other impacts does that have?

Prospect: Well, because data entry isn’t done properly, we lack information on long sales cycles or when reps change. That frustrates our future customers.

At this point, 5% stop.

The top 1% push just one layer deeper:

Salesperson: Your company is still running despite this pain. Why not just continue as is?

Prospect: We lost five deals worth $50,000 each last year because of this. That’s $200,000 short of target.

Salesperson: That sounds rough. How did that affect you personally?

Prospect: I got the frustration from our board and CEO.

That last line—the personal impact tied to a quantified business loss—is the meat on the bone. That’s when urgency becomes real. That’s when the buyer not only understands the challenge, but feels it.

The principle

Creating urgency is not about pitching faster. It’s about slowing down in discovery long enough to dig deeper than 99% of reps. Most stop too soon. The best keep asking until they uncover both the business impact and the personal impact.

When you uncover a strong use case like this, you transform your product from a nice-to-have into a must-have. And once the buyer feels the weight of the problem, they won’t want to wait six months to fix it. That is how you create urgency—and cut your sales cycle in half.

Tactic 2: Booking the Next Meeting Immediately

If uncovering a strong use case is the foundation of urgency, then booking the next meeting immediately is the simplest accelerator. It sounds basic, almost too obvious—but it’s the one tactic that most sales reps (and even CEOs) consistently fail to execute. And the cost of that failure is massive.

My early mistake: happy ears and wasted weeks

In the first half of my career, I ended almost every meeting the same way.

Prospect: We’ll discuss internally and get back to you.

Me (thinking): Perfect! They’re interested. They’ll reach out.

I had what we call happy ears. I believed the words at face value, and I left the meeting satisfied. But here’s what really happened:

• Two to three weeks passed before I followed up.
• Another one or two weeks went by before they replied.
• Then calendars were “full” for the next three weeks.

That’s six to eight weeks lost between two meetings. Multiply that by five meetings in a typical sales process, and you’re looking at 20 weeks of unnecessary delay. Almost half a year—gone.

All because I didn’t book the next meeting in the call.

Teaching the tactic at Taskbase

When I joined Taskbase, no one was doing it either—not the reps, not even the CEO, Sam. I taught him to end meetings with a clear next step. Something like:

Salesperson: From what I’ve heard today, I feel we have a strong use case worth exploring further. I’d suggest that in our next call, we dive into the business case, quantify the impact, and outline what it would mean if this challenge isn’t solved. Let’s already schedule that session—what does your calendar look like next week?

But this is harder than it sounds. On one call, Sam tried his version:

Sam: Okay, what do you think? Should we already put something in the agenda? You just tell us what we should do.

Prospect: No, that’s fine. We don’t need another meeting. Just send me an email in two weeks.

It didn’t work. Even with training, many people struggle to phrase it assertively enough. Booking the next meeting requires the right wording and the confidence to guide the process.

The right way to do it

Here’s the difference: you don’t ask for permission. You propose a concrete next step based on what you achieved in the meeting. You show why it matters, then you move directly into calendars.

Salesperson: Based on today’s conversation, I think the next logical step is to map out a proof of concept framework together. That way you’ll know if this solution really works for you. How about next Thursday at 10? Do you have your calendar handy?

This works because:

• You show confidence that progress is warranted.
• You propose a meaningful next step (not just a vague “touchpoint”).
• You move directly to scheduling, making it harder for the prospect to say no.

What if they resist?

Sometimes prospects push back.

Prospect: No need to book something now. Just email me in two weeks.

Salesperson: I understand. The thing is, if I email you, you might forget, or I might chase you and annoy you. To make it easier, let’s just put 30 minutes on the calendar. If we don’t need it, we can always cancel.

If they still refuse after two tries, that’s fine. In my experience, those people often really do get back to you—because they feel bad if they don’t. But in 95% of cases, if you use the right talk track, you will get the next meeting booked.

The impact on sales cycles

Think about the math again. If you save even four weeks between each meeting, and your deal requires five meetings, that’s 20 weeks shaved off the cycle. That alone can turn a nine-month deal into a three-month deal.

The principle

Don’t leave a call without the next meeting in the calendar. Don’t settle for “we’ll be in touch.” Don’t settle for “let’s have a touchpoint.” Be specific, be assertive, and make it easy for the client to say yes.

Booking the next meeting immediately might be the simplest tactic in this book, but it’s also one of the most powerful.

Tactic 3: Running Workshops Instead of Presentations

One of the most painful sentences a sales rep can hear is this:

Prospect: “Thanks, this was really interesting. We’ll take it internally and get back to you.”

I’ve heard it hundreds of times. Early in my career, I took it as a good sign. They found it interesting—great! They’ll follow up soon. But reality looked different: the deal disappeared into a black hole. Internal discussions stretched for weeks or months. I had no visibility into who was talking to whom, what was being said, or whether the project was moving forward at all.

This is one of the toughest moments in sales. You lose control of the process. You keep deals in your forecast because you’re optimistic, but in truth, most of them are already slipping away.

Why workshops matter

Workshops are the antidote. They are how you stop deals from getting lost in endless, unstructured internal conversations. Instead of leaving your champion to “convince” colleagues one by one over months, you bring the key people together in one session. You align them, prioritize use cases, and create tangible outputs the organization can use to decide.

In short: workshops compress decisions that normally take months or years into days or weeks.

A concrete example: the recording software

Let’s take a simple but realistic product: a call recording tool that:

• Transcribes calls.
• Provides coaching based on transcripts.
• Automatically enters data into the CRM.
• Generates analytics for sales leaders.
• Helps reps prepare better for future meetings.

That’s four or five potential use cases in one product already from this list.

Now imagine you present this in a discovery and demo sequence. Person A gets excited about the coaching. Person B loves the CRM automation. Person C wants analytics. Everyone leaves the meeting interested—but with different priorities. The result? Confusion. No decision. And then the dreaded: “We’ll take this internally and get back to you.” Because they have to align internally first.

Without structure, the client now needs multiple meetings, discussions, and votes just to decide which use case to prioritize. That can take months.

A workshop changes everything. Instead of scattering the discussion, you guide it.

Here’s what happens in a value workshop:

1. You recap the use cases already discussed.
2. You invite participants to add additional ones.
3. Together, you prioritize and rank them.
4. You select the top one or two and build a business case around them.
5. You document the outcome in a tangible format that can be used internally.

Now, instead of confusion and delay, you have consensus, a business case, and momentum.

How to position a workshop

When a client says they want to take it internally, I respond like this:

Salesperson: That makes total sense. At this stage, most teams want to align internally. Do you mind if I suggest something that will make that process much easier?

Prospect: Sure, go ahead.

Salesperson: Typically, when companies are deciding between different use cases, the fastest and most effective way is to organize a workshop. In that workshop, we’ll invite the right people early, recap the use cases, add new ones, and then prioritize together. We’ll narrow it down to the one or two most impactful, quantify the business case, and document everything so you can easily align internally. That way, you avoid dozens of scattered conversations and move forward with clarity. When do you think we could run such a workshop?

Notice the last line: “When do you think we could run such a workshop?” I don’t ask whether they like the idea—I assume the value is clear and move straight to scheduling.

Types of workshops

The workshop format depends on where you are in the sales cycle and the complexity of your solution. Here are the most common types:

• Value workshop (or use case workshop): Early in the process. Discover all possible use cases, prioritize them, and build a business case.
• Business case workshop: Quantify the impact of the chosen use case, tie it to company strategy, and calculate ROI. This one can often be merged with the Value workshop.
• Solution workshop: Define workflows, user journeys, or solution design. Essential if your product is highly flexible or configurable.
• POC workshop: Scope a proof of concept, align on success criteria, and set timelines.
• Decision criteria workshop: Align stakeholders on evaluation criteria, especially if an RFP is coming.
• Timeline workshop: Map milestones, responsibilities, and implementation phases.

When workshops are necessary

In small deals—say under 50k—you can often move forward without a workshop. A one-on-one business case meeting may suffice. But in larger deals (above 50k, and especially above 100k), workshops become indispensable. The more stakeholders are involved and the more complex the solution, the greater the need for a structured, collaborative process.

The principle

Workshops transform sales cycles by accelerating decisions that would otherwise take months. They create shared awareness of challenges and opportunities, bring multiple voices into the same room, and produce tangible outputs that drive momentum.

Instead of losing control when the prospect says, “We’ll take it internally,” you stay in control. Instead of endless debates inside the client’s walls, you facilitate one structured discussion that moves the deal forward.

That’s why workshops are one of the most effective tools for injecting urgency into enterprise sales.

Tactic 4: Mastering the Sales Process

If you want to accelerate deals, you need to know your sales process inside out. More importantly, that process has to mirror the way your buyers actually make decisions. A sales leader’s job is to design that alignment. A sales rep’s job is to use it in real time — so that at the end of every meeting, they know exactly what to suggest next.

When you don’t know the process, you fall back on hope: “Let’s touch base in two weeks.” When you do know it, you can confidently guide the client forward: “The fastest way to make progress is to build a quick ROI model together. How about Thursday morning?” One creates drift. The other creates momentum.

Small Deals: Meeting-Driven Playbooks

For smaller deal sizes — say under 20k or even up to 50k — the buying journey usually plays out in meetings. That makes the process relatively predictable, and you can define it as a sequence of steps.

One company might run:

• Discovery → Demo → ROI → Signature.

Another might prefer:

• Discovery + Demo (combined) → Team Demo → Proposal → Signature.

The exact steps aren’t the point. What matters is that you, the rep, know them cold. Because when you know them, you can suggest the right next step at the end of every meeting.

Here’s what that sounds like in practice:

Salesperson: “Typically, with companies your size, I’ll have four or five people in the loop: you as Head of Enablement, the Head of Sales, and two or three reps who are influential in the decision. Does that sound like your setup?”

Prospect: “Yes, that’s pretty accurate.”

Salesperson: “Perfect. Then the next step is a 45-minute team session where we can show the fit and get input from those reps. How does early next week look on your side?”

Notice what happens here: you’re not waiting for the buyer to figure out what comes next. You already know what the next step should be, and you guide them there.

And you tailor it by role:

• If the CFO is involved, suggest an ROI session.
• If the Head of Sales is involved, suggest a team demo to validate adoption.
• If the CEO is involved, suggest a short business case tied to a strategic initiative.

That’s sales process acumen in action.

Bigger Deals: Qualification Methodologies

Once you get into larger deals — 100k and above — you can’t rely on rigid meeting sequences. Every enterprise has its own quirks, exceptions, and internal politics. I’ve closed 300k deals without a business case, and I’ve seen 25k deals require one.

That’s why, in bigger deals, you need a qualification methodology in your back pocket. MEDDIC (or MEDDPICC, depending on your flavor) is my weapon of choice.

Here’s how I use it: after every meeting, I run through the acronym like a checklist.

• Metrics: Do I have a quantified business case yet? If not, the next step is to build one with the client.
• Economic Buyer: Have I met the EB? If not, I plan how to secure access.
• Decision Criteria: Do I know how they’ll judge solutions? If not, I set up a criteria workshop.
• Decision Process: Do I know the steps to signature? If not, I map it with my champion.
• Implicate Pain: Did they articulate their pain in business terms, or only me? If not, I dig deeper in discovery.
• Champion: Do I have someone who sells internally for me? If not, I cultivate one.
• Competition: Is another vendor in the mix, and if so, how are they shaping the deal?

This isn’t about following the acronym in order. It’s about spotting what’s missing and turning that gap into the logical next step.

For example:

• No numbers? → “Let’s build a simple business case together — I’ll bring the model, you bring the assumptions.”
• No EB? → “My clients usually do a short executive readout at this stage. I’ll keep it to three slides: problem, impact, and plan. Shall we set that up?”
• No criteria? → “To avoid wasted weeks, let’s align your team on evaluation criteria in one 30-minute session.”

That’s how a framework becomes a compass.

Think in Decisions, Not Activities

Too many reps think in activities: disco, demo, follow-up, touchpoint. Activities don’t close deals. Decisions do.

Every sales process is really just a string of buyer decisions:

1. Which challenge is worth solving?
2. Is this solution the right fit for that challenge?
3. What is the quantified business case?
4. Who else must be involved, what and how are they going to decide?
5. What is the timeline?
6. When do we want results?
7. How much money do we want to spend?

Your job is to guide the client through those decisions as quickly and confidently as possible.

The principle

Sales process acumen is knowing your process cold and aligning it with how your buyers actually buy. In smaller deals, that means knowing the right sequence of meetings. In larger deals, it means running a qualification framework like MEDDIC in the background at all times.

Either way, the goal is the same: never end a meeting without knowing the next decision — and proposing the fastest step to get there.

That’s what keeps momentum alive. That’s what shortens cycles. And that’s what separates the reps who wait from the reps who win.

Tactic 5: Referrals and Introductions

When I was at university, I sold insurance on commission to make ends meet. The company had a surprisingly well-structured sales process. In the very first meeting with a prospect, we didn’t pitch a product. Instead, we asked about their wishes for the future. We used pictures — a house, a holiday, a car — and had them pick what resonated most. Then we dug deep with questions:

• “How should the house look?”
• “What kind of kitchen would you want?”
• “What features matter most?”

We painted the dream vividly. Then, still in that same meeting, we delivered a massive amount of education: I literally drew three graphs by hand, explaining how the Swiss pension system works, how mortgages and amortization are structured, and how monthly investments grow over time. The clients walked away with new knowledge and clarity — and they valued the conversation.

And here’s the part that stuck with me: at the end of that first meeting, I had to pull out a sheet of paper with ten blank lines and ask for referrals.

Me: “Did you find today’s conversation helpful?”

Client: “Yes, absolutely. I learned a lot.”

Me: “Do you think your friends or family could also benefit from this?”

Client: “Yes, I think they could.”

Me: [looking down at the paper] “Who comes to mind?”

Then I stayed quiet. I stared at the paper. It was awkward. Painfully awkward. But here’s what happened: if I looked up, the client would say, “I’ll tell you next time.” If I kept staring, they felt the silence and started naming names. I wrote them down, asked for numbers, and got permission to call and “send their greetings.”

That’s how I first learned that referrals don’t magically appear — you have to ask for them. And you can ask for them much earlier than most reps think.

The Big Misconception

Most sales reps believe they can only ask for referrals once a client has been using their product for months. It feels safe to think that way — and it gives you a comfortable excuse not to ask. But it’s wrong.

You can get referrals in the very first meeting if you deliver value. Value doesn’t mean a free trial or three months of product usage. Value means giving them insights, challenging their assumptions, or helping them see their problem more clearly.

If you’ve made your prospect think differently — about their ROI, their workflows, or their challenges — then you’ve earned the right to ask.

How Not to Ask

Don’t ask vague questions like:

• “Who else could use this product?”
• “Do you know anyone else who might be interested?”

That never works. Nobody has an answer in ten seconds.

How to Ask Well

You need to come prepared with names. LinkedIn is your best friend here. Before the meeting, research your prospect’s first-degree connections. If they’ve left their network public, you can find dozens of potential fits. With Sales Navigator, you can search even more specifically. Pick three names who fit your ICP and walk into the meeting ready.

Then, at the end of the conversation:

Salesperson: “Thomas, I noticed you’re connected with Pascal, Eve, and Marlen. They’re exactly the kind of leaders I usually work with. Would you be okay if I reached out to them and sent your greetings?”

That’s it. A concrete ask, with names attached. Nine times out of ten, they’ll say yes. Sometimes they’ll say, “Let me send the message myself.” If that happens, suggest being CC’d so you can control the content. Otherwise, weeks go by and nothing happens.

Why Referrals Speed Up Deals

When you get introduced through a referral, half the selling is already done. Here’s why:

• The new contact doesn’t need a reference call — they already trust you because of the introducer.
• They often come into the conversation with a specific use case in mind, recommended by their peer.
• They may already believe in the business case, because someone they trust validated it.
• They know who else needs to be involved in their company and may even bring those people in.
• They are more likely to move quickly because the “is this real?” skepticism is gone.

In other words, referrals collapse weeks or months of selling into a single step.

The Principle

Referrals aren’t something you ask for months into a customer relationship. They’re something you can (and should) ask for in almost every meeting — as soon as you’ve delivered a bit of value.

Come prepared. Name names. Make it easy. And always stay in control of the follow-up.

Do this, and you won’t just fill your pipeline faster. You’ll close deals faster, because referred conversations already come with urgency built in.

Bonus Tactics: Advanced Plays to Reignite and Accelerate

The five core tactics in this chapter are enough to shorten most sales cycles. But there are situations where you need extra leverage — when a deal stalls, when procurement slows you down, or when you’re late in the process and want to test urgency without destroying your price. For those moments, here are two advanced plays that can make the difference.

Bonus Tactic 1: Executive-to-Executive Connections

Even if you run your process well — uncovering the use case, booking next meetings, running workshops — sometimes deals still stall. A prospect goes quiet. A meeting is canceled and never rescheduled. Or the project team simply loses steam.

When that happens, one of the most effective ways to re-establish momentum is to elevate the conversation: have your C-level executive reach out to theirs.

This does three things immediately:

1. Signals to the client that your company takes the evaluation seriously.
2. Creates visibility at the top, which often pressures the internal team to act.
3. Gives your champion cover — because now leadership on both sides is paying attention.

And this isn’t just a “rescue tactic.” For strategic accounts, you can use it proactively. Executive alignment early in the cycle can shorten decisions dramatically.

How to do it

Choose the right counterpart.

• If you’re selling to a CRO, have your CRO send the note.
• If the economic buyer is a CFO, get your CFO involved.
• If there isn’t a clear equivalent, default to the CEO.

Keep the subject line crisp: “Our Project.”

Here’s a simple template you can adapt:

Subject: Our Project

Hi [First Name],

This is [Your Name], [Your Title] at [Your Company].

Our teams have been in contact for some time regarding [Project XYZ].

I’ve heard excellent feedback about your team — diligent, collaborative, and highly professional. It’s been a pleasure for us to work with them, and it reflects very positively on your company overall.

If you’d like to explore this project from an executive perspective, I’d be happy to connect at any point. Looking forward to continuing the evaluation together.

Best regards,

[Your Name]

If the deal has already stalled, you can add a sentence like:

“Unfortunately, we haven’t heard from your project team in a while, and we’re concerned since both sides have already invested significant resources in this evaluation.”

What not to fear

Many reps hesitate to use this move, afraid they’ll upset their champion or damage the relationship. In practice, the opposite is true. Champions often appreciate the support, because it gives their project visibility and weight internally.

If you want to shorten cycles, you need to be willing to do things that feel a little uncomfortable. This is one of those things. And it works.

Bonus Tactic 2: The Hypothetical Discount

Discounts are one of the most abused tools in sales. Too often, reps cave at the end of a quarter: “If you sign by October, I’ll give you 20% off.” This doesn’t create urgency. It trains the buyer to wait until the end of the month or quarter, knowing a discount will magically appear.

A smarter approach — which I learned from Armand Farrokh and Nick Cegelski at 30 Minutes to President’s Club — is the hypothetical discount.

Here’s how it works:

Salesperson: “My CRO is considering an end-of-quarter discount. It hasn’t been released yet, but if we hypothetically could include a discount — would that change anything for you in terms of your decision process or timeline?”

That’s it. Simple, respectful, and powerful.

Instead of giving away margin, you’re testing urgency. You find out if price is the real barrier, or if the delay has nothing to do with money at all. And if they say yes — if a discount would accelerate the deal — you now know the trade-offs and can decide whether it’s worth offering.

Variation: The Built-In Discount

There’s another version of this tactic I’ve used myself. It plays on a simple truth: procurement and champions like to feel they’ve negotiated something. It makes them look good to their boss.

Here’s how you make that easier without destroying your pricing power:

1. Increase your list price slightly.
2. Always show a 10% “standard” discount in your proposal.
3. Attach conditions to that discount: logo usage, a case study, reference calls, or a specific close date.

This way, the buyer feels they’ve already won something. Procurement gets to report, “We secured a discount.” Your champion gets to look good internally. And you maintain control, because if the agreed timeline slips, you can remove the discount.

I’ve even had clients say, “We didn’t make the deadline, please send a new proposal without the discount.” It doesn’t happen often, but when it does, you close at full price with no pushback.

The Principle

Executive-to-executive connections and hypothetical discounts are not everyday plays. They’re situational. But in the right moments, they can reignite stalled deals, accelerate late-stage decisions, and keep momentum alive without sacrificing control.

Use them carefully, use them deliberately, and you’ll find they shave weeks — sometimes months — off your sales cycle.

Closing Thoughts: Making Urgency a Habit

If there’s one truth about deal velocity, it’s this: time kills more opportunities than competitors do. The longer a deal drags on, the higher the chance that priorities shift, budgets disappear, or champions move on. That’s why urgency isn’t about pressure — it’s about structure. It’s about guiding the client clearly and confidently, one decision at a time.

We’ve now walked through five core tactics — from uncovering a strong use case to asking for referrals — and explored a few bonus plays like executive-to-executive outreach and the hypothetical discount. Each tactic on its own can shave weeks off a cycle. Used together, they create the discipline and momentum needed to close six-figure deals in three months instead of nine.

But here’s the catch: knowing these tactics is not the same as using them.

Early in my career, I knew I should probably book the next meeting. But for three years, I didn’t. Instead, I waited. Prospects told me, “We’ll get back to you in two weeks,” and I believed them. Two weeks later, I sent a polite email with no clear suggestion. Sometimes they responded, sometimes they didn’t. My success depended almost entirely on whether I had a strong champion. When I did, things moved. When I didn’t, they stalled.

It wasn’t until I tested, failed, and tested again that I finally learned how to confidently say: “Let’s book the next step right now. How does Thursday work for you?” That single shift changed my close rates — and my career.

The point is: change doesn’t happen just because you’ve read a book chapter. These tactics only become second nature with repetition, feedback, and reminders. Sales leaders often don’t have the bandwidth to reinforce them daily. Which is why tools like AI tutors can help. At Taskbase, we’ve built AI tutors that live in Slack or Teams, analyze your call transcripts, and nudge you in real time.

For example:

• If you didn’t book the next meeting, the tutor will flag it and suggest a talk track you could use.
• If your discovery questions stayed too shallow, it might ask, “Want to try digging deeper next time? Here are three ways to phrase it.”

It’s like having a coach sitting on your shoulder, reminding you of the right moves until they become habits. And that’s the secret: urgency isn’t a one-off tactic. It’s a muscle you build with repetition.

So here’s my challenge to you: don’t just admire these tactics. Practice them. Test them. Fail with them. Then try again. Over time, they’ll stop feeling like “techniques” and start becoming how you naturally run every deal.

Because once urgency becomes a habit, closing 100k deals in three months won’t be the exception. It will be your norm.