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.

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.

My first project was delayed by 5 months. The second? 6 months. Then came another with a 1-month delay, and now, the latest is heading towards a 3-month delay. In interior design and construction, delays are almost normalized. There are countless moving parts, multiple agencies, vendors, approvals, procurement, site conditions—the list never ends. For a long time, I accepted it as “part of the industry.” Until I started looking at the numbers. Every month, I disburse salaries. Every month, office rent is due. Every month, software subscriptions, consultants, utilities, insurance, and operational costs continue whether a project moves or not. None of these expenses pause because a client decides to. For the longest time, I was uncomfortable talking about money. Like many designers, I worried that discussing finances would make the relationship transactional. But I eventually realized something. Not addressing delays wasn’t being professional—it was exposing my business to unnecessary risk. Today, I classify delays into three categories: ➡️Genuine unforeseen events : Natural disasters, political unrest, supply-chain breakdowns, or situations beyond anyone’s control. These deserve empathy and flexibility. ➡️ Legitimate project constraints : Delayed statutory approvals, structural discoveries, or technical issues that genuinely require more time. These need collaborative planning and revised timelines. ➡️Preventable delays : Carelessness. Indecision. Lack of coordination. Repeated postponements despite having all the information needed. These are business decisions, and they have business costs. I’ve learned to treat each category differently. The first deserves understanding. The second deserves planning. The third deserves accountability. Today, every extension comes with a documented timeline revision, clear communication, and, where applicable, financial implications. Because if my business continues to incur monthly costs, project delays cannot remain a one-sided burden. Running a design studio isn’t just about creating beautiful spaces. It’s about protecting the business that makes those spaces possible.

Your board wants results by ASAP. They take four weeks to respond to your messages... A development director laughed mid-sentence on a call this week, then went quiet. "There is a mismatch in expectations. It leads to breakdown." That is the unspoken contract inside most nonprofits. The board demands urgency from the staff. The staff cannot create urgency in the board. And the executive director gets blamed for the gap. I sat with this team and we counted the asks the staff had open with the board. A budget revision from February. Three policy documents. A vendor contract. A revised case for support. Eleven items. Average wait, twenty-three days. The same board was asking, in the same breath, why fundraising was behind schedule. (and yes different boards of different organization have different levels of oversight) You cannot drive forty miles per hour with the parking brake on. What every nonprofit leader has to learn to say out loud, and I know it is uncomfortable: "We will hit the goal you set. We need you to take action in five business days when we ask, or the goal moves out by the same number of days you take to respond." Not a threat. Not passive aggression. A planning constraint. Boards understand planning constraints. They will respect it from you. The teams that hit year-end goals don't have the smartest staff. They have boards that understood the approval chain had to move at the speed of the campaign. Because in fundraising, the board that sets the deadline and slow-walks the decision is the board that funds its own failure.

"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

I once ran a core banking transformation where the entire business case fit in a single sentence. The sentence was this: The platform was going out of support, and the replacement had to be live before the deadline. That date organized everything. It set the scope, the budget, and the sequencing. It also handed every steering committee an easy answer to the hardest question in the room, which was: "Why are we doing this at all?" The answer was that my client had no choice. I believe that answer is where deadline-driven programs quietly go wrong. That program ran on Oracle. Oracle sets end-of-support dates, SAP sets them, and every major enterprise platform sets them. The forced-upgrade clock is structural to enterprise software. But a support calendar is only a constraint, and a constraint is not a strategy. When the date becomes the reason, the program takes on a predictable shape. The business case shrinks to necessity. Going live on time becomes the definition of success, which means a program can fail on every measure that matters and still be called a "win", as long as it fails on schedule. SAP's customers are the clearest current example. The 2027 deadline has shaped their roadmaps for three years. Then, at its largest event this month, SAP led with autonomous AI and recast the migration as the plumbing beneath it. The vendor moved past the date. Many of its customers cannot, because the date is still the entire plan. A deadline can tell you when. It was never meant to tell you why. So here is the test I would put to any program carrying a deadline: Take the date out of the business case. If what remains cannot justify the investment on its own, you do not have a transformation strategy yet. You have a renewal with a deadline attached. #ERP #ProgramGovernance

🚨 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.

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

The conversation I wish I'd had in every client kickoff: 
"Let's talk about how decisions get made on your end." 
Here's how I'd approach it now. We've covered scope and timeline. I want to make sure we map decision requirements so nothing gets delayed waiting for approvals. 
For each major milestone, help me understand: • Who has final approval authority? • Who needs to weigh in before that person decides? • What information does the approver typically need? • How much lead time should we plan for their review? Example: Client: "We need this done in 6 weeks."
 Me: "Let's map the approval process. Who signs off on the final design?" Client: "I do, but my boss usually reviews it first." Me: "How long does she typically take?" Client: "About a week." Me: "So if we need her approval by week 5 to deliver by week 6, that puts us on a tight timeline for revisions. What's most important - hitting the date, staying in budget, or having time for quality refinements?" Client: "Well... all three." Me: "I understand. Based on your approval timeline, we can guarantee two of the three. Which two matter most?" This conversation takes 10 minutes in kickoff and prevents weeks of finger-pointing later. When clients see their own decision timeline mapped out, unrealistic deadlines correct themselves. How do you help clients understand their role in project timelines?