Understand Stakeholder Expectations: Clarify what "quick results" means, what outcomes they expect and by when. Identify which deliverables are most critical. Assess the Workload and Resources: Break the project into tasks, estimate the time and effort for each, and consider the availability and capacity of your team. Prioritize Deliverables: Focus on high-impact tasks that can show early progress. Use techniques like MoSCoW to set priorities. Communicate Trade-offs: Explain the implications of tighter timelines. Present data to support your timeline estimates. Get Buy-in: Collaboratively agree on the timeline with stakeholders, making them part of the decision-making process to foster understanding and support.

I manage deadlines by rigorously prioritizing tasks based on impact and dependencies, then applying agile principles for flexible, iterative execution. This was crucial at my last startup. My co-founder and I would have frank conversations, often daily, to transparently communicate progress and scope. There was this one time we were racing to hit a product milestone, and we had to quickly decide which 'nice-to-have' features to defer. By clearly outlining what was realistic within our tight timeframe and collaborating closely to adjust expectations, we kept alignment and delivered a solid core product on time.

When stakeholders are pushing for quick results, I make it a priority to have an honest conversation about what’s truly possible, breaking down the project into clear phases and highlighting the risks of unrealistic timelines. I always back up my proposed deadlines with concrete data and past experiences, so they see it’s not just about caution but about delivering quality outcomes. By involving them in the planning and being transparent about challenges, I find it’s easier to align expectations and get their buy-in for a realistic schedule that everyone can stand behind.

Well, to set realistic deadlines when stakeholders demand quick results, start by clearly understanding project scope, priorities, and success criteria. Break work into smaller, manageable tasks and estimate time based on data, not guesswork, also, involve the team to validate. Communicate openly about risks, dependencies, and resource limits. Build in buffers for unexpected delays. Engage the team to validate estimates and ensure buy-in. Regularly update stakeholders with progress and adjust timelines transparently if needed. Setting clear, achievable deadlines earns trust and delivers sustainable results.

I believe in open and honest communication. I’m not afraid to give pushback when needed, and make it a point to clearly explain what’s feasible by providing context, outlining the full scope of work, and highlighting potential challenges. This helps stakeholders understand why certain deadlines may not be realistic and allows us to align on achievable goals without compromising quality.