Negotiating Deadlines

In my last role, I led two super important 0 → 1 projects. One failed, one succeeded. Here are some learnings: The two projects: Project 1: Hey, can we take this existing unpaid feature & unbundle it to make revenue? Day 1. I’m excited! First, I need a Notion to make sure everyone is aligned. Day 10. Analysis-paralysis. Ok I think I have the structure. Let me just do a little more research. Day 20. Imposter syndrome. I have no idea what I’m doing. I'll get fired. Ugh. Project 2. Hey, for our WAU metric, I think hosting great leaders in the community weekly will be great. Day 1. Action. I’m not sure what the format should be, or who these leaders are. How does one even go about this? Let me go ask some people & speak to users. Day 3. Calendars blocked, topic closed. Now we have to announce it so people show up. Day 7, shipped. Now, what was different? 1/ Commit to a deadline before knowing the "how" In project 1, I had too much freedom without constraints. In Project 2, we decided we wanted to host the first event in 7 days. Booking the calendars of members before closing the speaker was scary. But we had now made a user commitment, we had to figure it out. When you’re doing new things, setting the deadline & then figuring it out always works. You could make the commitment in different ways: book the venue, book a meeting for a team review, just pick a launch date. 2/ Make small decisions, iterate as needed We’re taught to plan → iterate plan → build. I tried that. But, hovering at 30,000 ft gave no feedback. In reality: build → iterate → plan works. In the second project, blocking the date forced us to figure leaders we want to get, a host, structure & the GTM in time. By shipping tiny pieces, we wrote the strategy on the fly & could judge it against reality, not theory. Eventually, we were hosting great leaders every single week. We built the playbook by doing. Drafting the final launch copy, landing page, hero image kills analysis paralysis & makes things tangible. Add a ‘beta’ label on anything new; the word alone lowers the stakes. 3/ Make your project more people’s problem In Project 1, I acted like a lone-wolf. I had to do it by myself to prove my worth. This threw me into a spiral of self-doubt. In the 2nd project, I asked for help (loudly, clearly, often) & the project became the team’s project. That allowed me to get more input & support. In the end, when it was a success, it became a shared win. Way more fun, trust me. Getting buy-in isn’t automatic though. Here are three things that work: 1/ Get the founders to buy-in to your idea first. Their urgency becomes everyone’s urgency. 2/ Bring your manager along for the ride. The more they know about what you’re doing and your challenges, the more they will figure out how to support you. 3/ Use public slack channels, tag specific people for asks. Don't DM for favours, it tilts incentives.

A few months ago, I spoke to a project manager who had just wrapped up a client project. Or rather, should have wrapped it up. The project was originally going to be for 8 weeks. Everyone agreed on the timeline upfront, shook hands, and dove in. But then the delays started: • The client needed more time to approve designs. • The vendor supplying key software missed their deadline. • Halfway through, a critical feature needed to be reworked. Suddenly, the "8-week" project stretched to 12 weeks. And the Contract? It had strict deadlines and no room for adjustments. This caused: • Frustration on both sides. • The client was unhappy about delays. • The project manager was penalized for missed deadlines. • The relationship? Completely soured. Deadlines look great in contracts. Because they are clear, concise, and seemingly immovable. But projects don’t exist in a vacuum. That's why things often go wrong: 1. Dependencies Get Overlooked Deadlines often rely on third parties - client approvals, vendor deliveries, or team availability. One missed milestone, and the entire timeline collapses. 2. No Cushion for the Unexpected Tech hiccups, team illness, or surprise feature requests can derail progress. Without a buffer, small issues snowball fast. 3. Rigid Timelines Create Tension When deadlines slip (and they almost always do), the blame game begins. Trust erodes, and disputes become inevitable. 4. The Risk of Penalties Missed deadlines can trigger financial penalties or harm your reputation - even when delays are beyond your control. 5. Misaligned Expectations Rigid deadlines assume everything will go perfectly - which rarely happens. Without clarity on flexibility, both sides end up frustrated. Let’s go back to that project manager’s situation. What if the contract had been different? Because a good contract would have: a) Buffer Periods Built Into the Timeline Adding a 1-2 week buffer to each milestone allows for delays without derailing the project. b) Clear Contingency Plans Specify how delays will be managed - who’s responsible, what adjustments are made, and how costs or timelines shift. c) Defined Flexibility Mention that deadlines may shift due to dependencies or unforeseen issues. d) Shared Accountability Be clear on mutual responsibility - clients delivering approvals on time, vendors meeting commitments, and the team staying on schedule. Imagine that same project manager with a flexible contract: • When the vendor delays delivery, the buffer period absorbs the impact. • When the client needs extra time, the contingency plan kicks in. • And when the project wraps at week 12 instead of week 8, no one is surprised. No penalties. No disputes. No burned bridges. Deadlines are important. But assuming they won’t change? Now you are asking for disaster. —— 📌 If you need my help with drafting flexible contracts for your high-ticket projects, then DM me "Contract". #Startups #Founders #Contract #Law #Business

He had two choices: ❌ Stay quiet, deliver late, and hope the client will understand. ✅ Own the truth, admit the gap, and offer an alternative. A CEO whom I coach recently faced a tough call. One of their biggest clients was over-promised by the sales team. The product team knew, the deadline was impossible. This CEO chose to uphold the values of Integrity & Customer Centricity. He called the client, laid out the reality, and presented a revised plan. Then he reminded his team: “Integrity means we only commit when we can truly deliver. Customer centricity means we protect long-term trust over short-term wins.” How do you think the other party must have responded? They said, “You’ve just proven why we choose to work with you. Most companies would have hidden this until the last moment.” The takeaway, Values don’t live on a website. They live in the pressure moments. When you’re forced to choose between integrity and the easy way out, your decision is your culture.

Tight timelines are motivating—until…… they start breaking everything around you. At first, it’s tempting to agree: “Yeah, we can finish it faster.” “Sure, we’ll figure it out.” Because on paper, everything looks good. Everyone feels motivated. The timeline feels exciting. Until the pressure sets in, and you realize the plan didn’t leave any room for → mistakes. → Or questions. → Or real life. Then, Rushing leads to shortcuts → Shortcuts lead to mistakes → Mistakes lead to delays…………the very thing you tried to avoid! Most deadlines aren’t missed because people are lazy. They’re missed because the plan didn’t leave enough space for real life. Now, before starting any project, I try to ask: → What if someone needs more time? → What if we have unexpected changes? → Is there space to slow down if we need to? But to be honest, I don’t always get it right. Sometimes I still plan too tightly. But every project teaches me a little more. And every time I leave a little extra space, things go a lot smoother — for everyone.

"Client shall provide Vendor access to Client's Computer System by January 3. Vendor shall deploy the Solution by January 10." "Vendor shall provide the Deliverables within 4 weeks of the date hereof (the "Deadline"). Client shall provide any requests to modify the Deliverables within 2 weeks of the Deadline, and if Client fails to do so, the Deliverables shall be deemed accepted." Do you see the problem with these clauses? In each case, each party has a deadline for a task. In each case, the second party's task is dependent on the first party's task. But in neither case does the second party's deadline get extended if the first party fails to meet their deadline. So if you're the second one to act, you could be put in a situation where you miss your deadline because the other party missed their deadline. In practice, I suspect most courts would impute an adjustment to the second party's deadline. But I don't think that's a guarantee. Particularly if there is an exclusive remedy clause that could prevent that. So why risk it, especially when there's an easy fix? When a deadline is contingent on performance by someone else, peg the deadline based on when the other party's performance actually occurred, not when it was supposed to have occurred. For example: "Vendor shall deploy the Solution within 7 days following Client providing Vendor access to Client's Computer System." #ContractTrap #contracts #inhousecounsel #law

Without trust, nothing moves in negotiation. Few negotiators have a strategy to build it. You’ll learn six proven moves to build trust, even when time is short or stakes are high. I’ve helped corporate leaders negotiate high-stakes deals in over 30 countries, where trust builds access and leverage. In high-trust negotiations, joint gains increase by over 40%, according to research. Trust isn’t a luxury in negotiation. It’s your license to operate. Yet we often rush the process: ✔ Withhold information ✔ Play it safe ✔ Miss the bigger win Here are six concrete moves from Harvard's PON (Program on Negotiation) to build trust quickly, even with strangers: 1️⃣ Speak their language: Not just industry lingo. Show cultural fluency and listen for nuance. A single word misunderstood can knock you out. 𝘛𝘪𝘱: Prep to show curiosity, not ignorance. 2️⃣ Use your reputation: If trust isn’t built yet, borrow it. Share your track record or get an intro from someone they trust. 𝘛𝘪𝘱: Third-party validation can break early resistance. 3️⃣ Make dependence visible: Highlight how you both need each other to win. Scarcity fosters cooperation; just don’t overplay it. 𝘛𝘪𝘱: Say, "Here’s what only we can offer you." 4️⃣ Offer a no-strings concession: Low cost to you, high value to them? That’s the trust jackpot. 𝘛𝘪𝘱: Gift first, then negotiate. 5️⃣ Label every concession: If you don’t say it’s a concession, they won’t treat it like one. 𝘛𝘪𝘱: Spell out what it costs you and why it matters. 6️⃣ Explain your demands: People default to assuming the worst. A clear rationale for your ask makes you seem fair. 𝘛𝘪𝘱: Even if they don’t like it, they’ll trust it. Trust isn’t a feeling, it’s the outcome of visible, intentional behavior. Which of these six trust-builders do you use most, and which one do you forget? Let me know in the comments. Save this list for your next tough negotiation. ♻️ Share if this made you rethink how you build trust. 

🚨 A Hard Truth: Yes, you can have fixed dates in Scrum The purists will tell you otherwise. What I’m telling you is you can, just don’t fix scope. Scrum is built on empiricism. Every Sprint already has a deadline. Every Sprint Review gather your Scrum Team and stakeholders to provide feedback on the latest increment and inspect progress towards the Product Goal. And don't leave this out of the Sprint Review: ask what’s the most valuable, useful thing we can deliver in upcoming Sprints before our final release date? Think of the iron triangle, sometimes referred to as the triple constraints of time, cost, and scope. You can fix two sides, but not all three: ⏰ Fix time and cost → scope must flex 📦 Fix scope and time → cost explodes by trying to add more people (and Brooks’s Law reminds us this usually makes things later) 💀 Fix scope and cost → release dates will probably get pushed and you'll go over budget This isn’t just a Scrum reality. It works the same way with Waterfall. Trying to lock all three sides leads to poor quality, technical debt, team burnout, and cut corners. Scrum doesn’t allow quality to be the thing that flexes. Scrum makes the trade-offs transparent: ✅ A fixed date doesn’t mean fixed scope ✅ You maximize value within the boundary of time ✅ You use transparency, inspection, and adaptation to make smart trade-offs 💪 A fixed release date can even sharpen focus. It forces the team and stakeholders to ask: what matters most? What must be delivered, and what can wait? Waterfall treats a deadline as a contract. Scrum treats a deadline as a constraint for focus and creativity. And because progress is inspected every Sprint, you won’t discover you’re late at the last minute, you’ll adapt long before the crunch hits. 👉 The real question isn’t "Can Scrum work with deadlines?" It’s "Are you managing scope to meet the date, or pretending the date will flex for your scope?" Deadlines aren’t the enemy, pretending scope is fixed is.

One of the trickiest parts of growing an agency? Managing client expectations without burning bridges. Early on, I thought being a "good partner" meant always saying yes. But here’s what I’ve learned: saying yes to unrealistic timelines or promises doesn't build trust. It builds resentment on both sides. Now I approach it differently: → Set clear expectations upfront → Explain the "why" behind timelines (strategy > speed) → Show how doing it right once beats doing it rushed three times → Always over-communicate progress, even if it’s just a small update Most founders respect honesty. What they hate is feeling left in the dark. You don’t lose respect by pushing back; you lose it by overpromising and underdelivering. The earlier you set the tone, the easier everything else gets.

In the fast-paced world of business, requests from senior managers can often appear as non-negotiable demands. Understanding the underlying request can transform how we respond and lead to more effective outcomes. Consider this common scenario: Your CEO casually mentions, “I need the project update presentation by Monday.” At first glance, this sounds like a firm deadline. However, this could be an opportunity for negotiation rather than a strict command. How to Navigate: Clarify the Need Start by understanding the urgency, importance, and significance of the request. For example, you might say, “I understand the presentation is important. Could you share more about what will be discussed? This context will help me prioritize the most critical information.” Assess Your Capacity Evaluate your current commitments. If the timeline is tight due to other priorities, communicate this. For example, “I’m currently wrapping up the quarterly budget review, which is also due Monday. Would it be possible to have an extra day for the presentation to ensure all data is accurately captured?” Propose Alternatives If the original deadline is not flexible, suggest alternatives that meet the need without compromising the quality of work. “If the full presentation can’t be delayed, I could provide a summary of key points by Monday and follow up with a detailed report by Wednesday.” Confirm Agreement and Shared Understanding Ensure you and your CEO are on the same page. “To summarize, I will provide a summary by Monday and the full presentation by Wednesday. Does that work with your schedule?” This approach shows your proactive engagement and respects the executive’s needs while managing your workload effectively. It’s about finding a middle ground that benefits both parties, turning top-down demands into collaborative, negotiable requests. Remember, every executive demand is an opportunity to showcase your strategic thinking and negotiation skills. Don’t shy away from these conversations; they are your chance to lead effectively. #ExecutivePresence #Negotation #TimeManagement #ExecutiveCoaching

Week 1: “Oops…Where’s the Report?” Jack was supposed to submit a report yesterday and it’s not in your inbox. It’s a small project, a small mistake but it’s late. You could let it slide but you know small things like this can add up. Have a quick 1:1 with Jack. Ask what happened, listen without judgment, and clarify expectations for future deadlines. Reinforce that you’re on the same team and that you value proactive communication. A small conversation now avoids bigger headaches later. If Jack starts missing deadlines repeatedly, it’s time to formalize your approach: • Document occurrences – Keep a detailed log of each missed deadline. Include dates, project impact, and notes from any conversations you had. This creates a clear record and helps you see patterns over time. • Dig deeper – Explore why Jack is missing deadlines. Are there skill gaps, competing priorities, unclear instructions, or personal distractions? Understanding the root cause allows you to offer meaningful support rather than simply reprimanding. • Set clear expectations – Clearly outline what you expect moving forward. Define deadlines, standards, and any consequences for continued misses. A performance improvement plan with measurable milestones can help formalize this. • Follow-up consistently – Schedule regular check-ins to monitor progress. Offer feedback, guidance, and encouragement. Consistency shows that you take deadlines seriously but are invested in his success. • Escalate if needed – If Jack continues to miss deadlines despite support and clear expectations, involve HR or leadership. Escalation ensures fairness, protects team productivity, and demonstrates that repeated lapses have consequences.