Timing Your Sales Proposals

Anybody else feeling like "Whelp, nothing is happening between now and January 1"? Seasonal sales cycles can feel like an excruciating waiting game. You’re eager to close deals, but your customer's timelines are driven by rigid schedules, budget reviews, or planning seasons. In some industries, waiting until decisions are finalized often means you’re too late. You've got to make sure your solution gets attention at the right time. Here’s how to align your approach with your customer's planning rhythm: Start by mapping out the year from your partner’s perspective. When do they begin budgeting? When do decisions need approval? For example: Winter-Spring (January–March): Many organizations start initial budgeting and planning. This is the time to initiate conversations, offer insights, and get on their radar. Late Spring (April–May): Decision-making accelerates as deadlines approach. Ensure your proposal is ready and that you’ve addressed all their concerns before contracts are signed. Summer (June–July): A quieter period for some industries, but also the final chance for last-minute decision-makers. Be prepared to adapt quickly for latecomers. Introduce urgency by emphasizing: Future Pain Points: “Remember how stressful last year was when you couldn’t find enough staff? We can help you avoid that.” Cost of Delay: “Acting now ensures we can deliver at the scale you need, without rush fees or last-minute compromises.” Operational Efficiency: “Planning ahead allows us to onboard smoothly, saving time for your team.” Build Relationships During the Off-Season Slow seasons are opportunities to build partner pipeline. Use this period to nurture relationships, showcase results, and prepare for the next buying cycle by cultivating new partnerships, creating joint value propositions, and enabling teams on partner best practices. Slow sales cycles are an opportunity to plan smarter, and learn how to plan together.

We're entering the final weeks of K12’s buying season. And if you're not adjusting your sales approach, you're going to miss your window. Right now, your buyers are: Trying to spend remaining funds tied to specific grants. Getting pulled into state testing, staffing, and summer planning. Fielding last-minute pitches from every direction. They do not have time for: Vague discovery questions. Long demos that aren’t tailored. “Just checking in” emails. Here’s what actually works in this part of the cycle: Show them exactly how your solution aligns to their strategic goals Be crystal clear on how it can be funded. Title I, literacy mandates, state-level allocations. Offer a clear, simple implementation timeline (especially if it starts in the fall). Ask: “What do you need from us to feel confident finalizing this before fiscal year close?” And if the timing really isn’t right? Don’t ghost. Set a follow-up for late July or early August and use the next few months to build champions, gather case studies, and prep for a smoother fall. Spring is where urgency and empathy need to live together. Know what’s driving your buyer and meet them there.

The EdTech market has a timing problem. After analyzing 7k+ K–12 POs across 800+ districts, we wanted to understand why forecasts fail. 60–70% of public education spending aligns with fiscal year-ends, and June sees a 4–5× PO surge. Average deal sizes jump 41% from March to June. Yet most teams allocate effort evenly across all months and miss 60% of their opportunities. Competitors win on timing, not always on product. Public budgets, RFPs, and contract expirations are all public data and they show you how to gain the upper hand on underprepared teams that are flying blind. Timing intelligence is now a strategic imperative. When you know each district’s calendar, you shift from reactive to predictive. As we know... predictable revenue is the best type of revenue. We wrote a full guide that covers fiscal spending patterns and phase-specific tactics that will help you convert your relationships into opportunities then into deals. 👉 Read more: https://lnkd.in/eSxW4hC8 #EdTech #K12 #PublicSectorSales

I used to think B2B deals closed because of great salespeople. I was wrong. Great salespeople help, but most deals close because of timing. Not your timing. Theirs. The moment prospects hit a breaking point and must act now. Examples: → An agency lands a big client who suddenly demands detailed time reports → A founder realizes they’ve lost $50k from inaccurate time tracking → A project manager gets fed up after the 3rd manual system failure These aren’t pain points. They’re trigger moments. The difference? Pain points create consideration. Trigger moments create urgency. When you know your customer’s exact trigger moments, you can: → Target them at the perfect time → Tailor your pitch to their urgent need → Beat competitors to the deal Most B2B teams focus on features and benefits. Top performers focus on timing and triggers. Do you know the # 1 trigger moment for your ideal customer?

I jump on a lot of sales calls. One of the most consistent objections I get is around timing. Here’s my plan to address it going forward. A timing objection sounds like these: • “We have an internal strategy meeting in 1–2 weeks, we’ll decide then.” • “I’m interviewing a few other folks and a headhunter; send info and I’ll circle back.” • “We won’t start this until Q1 / 90 days from now.” • “I’m talking to multiple vendors; will decide by end of year.” • “I’m traveling / on a cruise / holidays... let’s reconnect after.” These are frustrating. Because you don’t get a no. You get a “maybe”. And you’re not sure if they mean it or if they’re just saying no in the softest way they can. Here’s my plan to handle these going forward: 1/ Figure out if timing is a real objection “Totally fair. Before we park it under ‘timing,’ can I ask one blunt question? On a scale of 1–10, how much do you actually want this outcome in the next 6–12 months?” If they answer below an 8, I’ll follow up with “What would you need to see or believe for this to be a clear yes at some point?” 2/ Position myself as a partner for ‘strategic’ meetings Many times, they need to discuss with their partner or team. So I’ll ask what would have to be true in that meeting for LinkedIn to win a slot. Then I’ll send them a custom strategy they can use to sell their team/partner. 3/ Contingent start date Because I’m busy and my spots fill up fast, people need to lock in if they want to secure a spot. It can be a “soft” lock-in they can cancel if the meeting/decision doesn’t go well. But I can get a lot more verbal commitments here. 4/ Show the cost of waiting Everyone looks at the cost of hiring an agency, but rarely the cost of inaction. 5/ Pre-commitment Start the call with: “By the end of this call, the only decision I’m looking for is: • ‘Yes, let’s start on X date,’ • ‘No, it’s not a fit,’ or • ‘Not now, and here’s exactly what would need to be true for it to be a yes.’ Are you okay giving me one of those three so we don’t leave it vague?” ~ I’m going to try it out over the next 90 days and will let you know how it goes! Any questions or suggestions?

20+ years and $2B in sales taught me that "send me a proposal" isn't good news. It's an alarm bell. "Send me a proposal" means 4 different things.  Each requires a different response. 1️⃣ THEY NEED A NUMBER TO BUILD THE BUSINESS CASE They have a real problem and need numbers for a business case. Smart reps provide budgetary ranges - not binding quotes - and offer to co-build the business case. 🎯 Manager questions: Who’s the Economic Buyer? Have we met them? What does the approval process look like? 2️⃣ THEY'RE COMPARISON SHOPPING They need your proposal to fill a column in their vendor scorecard. Smart reps ask: What problem are you solving?  Then they co-define the capabilities needed.  If the buyer won't engage, walk away. 🎯 Manager question: Did you help develop the buying criteria? 3️⃣ THEY DON'T KNOW WHAT ELSE TO ASK FOR They liked the demo but haven't done enough discovery. Smart reps redirect: "Before I put something together, let's spend 20 minutes defining the problem and the capabilities you need." 🎯 Manager question: What have you learned about the problem, business case, and stakeholders? 4️⃣ THEY'RE ENDING THE CONVERSATION POLITELY The tell: They won't say what the proposal should include or commit to a review meeting. Smart reps test it: "Happy to. When can we schedule 30 minutes to review it together?" 🎯 Manager question: Is there a review meeting on the calendar?  THE QUESTION THAT CHANGES EVERYTHING One of my sellers was deep in an enterprise deal. The Champion asked for a proposal. He smiled and asked: "What are you gonna do with it?" The Champion needed budgetary numbers for finance approval. Not a 40-page proposal. We provided a range, strengthened the business case, and ran discovery with other stakeholders before making our commercial proposal. That deal turned into tens of millions. Next time a buyer says "send me a proposal" - ask "What are you going to do with it?" 👉 DM me if you want help coaching your team on how to qualify deal momentum.

If you still think you’re selling IT, you already lost the deal. You just don’t know it yet. I spent years walking into MSP sales calls with slide decks full of tools, tickets, uptime charts. Prospects smiled, asked for pricing, then went dark. I was selling stack, not decision. Commodity, not change. Shift started when I anchored every deal to a real date inside buyer calendar. Not features. Not SLAs. A concrete moment where success or failure would show up in front of leadership. I began asking for: → Upcoming board meeting → Renewal with largest customer → Planned acquisition → Year‑end audit → Peak season where outage hurts most Once event sat in view, sales motion changed. Discovery shifted from “What tools do you use now” to “What happens inside boardroom if numbers stay flat”. Proposal moved from list of services to safety plan for a specific day. Results came fast: → Shorter cycles → Higher close rates → Cleaner deals with clear scope Because decision maker did not feel pushed toward MSP. Decision maker felt guided through high risk moment already coming. New mindset for every MSP seller: ⚫ Stop saying “I sell IT services” ⚫ Start saying “I guide critical business decisions” Language must match: 🔹 Talk in risk, not routers 🔹 Talk outcomes, not uptime 🔹 Talk moments leaders lose sleep over, not ticket queues When you frame offer around future day in buyer world, your quote no longer sits as line item. Proposal becomes insurance policy for future. MSPs do not sell IT. MSPs sell secure outcomes on specific dates.