Talking to people about project design

We interview different people, in different industries, at different points in their careers, about project design- what it means to them, how it helps them and how sometimes, it is a pain in the butt. We don't have all the answers for how to design the perfect project, but through these conversations we try to cut through the theory and the jargon to talk about what works and what doesn't work in different situations. Come join us if you want to learn more about project design in the real world!

Episode 1

"Organizations think they're answering the question, but they're not really answering the question." This episode explores why- and what to do about it!

In this inaugural episode of Project Design: The Good, The Bad and The Wild, host Danielle Wilkins sits down with guest Kavita Desai to discuss what she has learned over her 18 years leading business development and proposal design for organizations like Palladium Group and Abt Global, including the costly mistakes teams make when designing multi-sector programs under pressure, and a success case in a complex multi-sector program in East Africa that integrated economic growth, nutrition, WASH and community development.

In this episode:

The stakeholder engagement strategy that prevents missing critical perspectives

How to bound your work when four technical areas could each pull you down a rabbit hole

The "touch the hot pan" phenomenon: why people learn design importance the hard way

Practical advice for small organizations without full proposal teams

Theory of Change pitfalls and the themes you need to identify first

Protecting design integrity while meeting aggressive deadlines

Whether you're designing programs for donors and foundations, leading social impact initiatives, managing complex projects, or just trying to understand what project design actually means, this conversation offers practical frameworks you can use immediately.

Subscribe to hear more honest conversations about project design in the real world. New episodes drop every Tuesday.

Have a project design story to share? Connect with Danielle on LinkedIn or share your biggest project design lesson on LinkedIn using #ProjectDesignPodcast

Episode 2

In the second episode of Project Design: The Good, The Bad and The Wild, host Danielle Wilkins sits down with Matt Kessler-Cleary to talk about project design from his unique perspective as his team's 'fixer of broken things'. With 10+ years of experience as a wearer of many hats AND jack of all trades for the strategy team of one of the largest divisions in a busy global NGO, Matt brings both an implementer and a planner perspective to the Project Design podcast.

Join us for part 1 where we dive into a specific case study of a project that skipped parts of the design phase and what can go wrong. Matt walks us through his experience of dealing with the fallout of a design process that assumed people would simply be on board- and skipped over internal stakeholder engagement. He shares how he had to retrofit stakeholder engagement into an already-moving project and his take aways from the experience.

Be sure to stay tuned for Part 2 where we shift from problems to solutions, and we get into what Matt has learned about how to functionally engage stakeholders, why projects need flexibility rather than rigid plans, and how keeping people- not just process- at the center of design is a non-negotiable for project success.

Part 2 drops on Tuesday Nov. 4th! Be sure to follow to get a notification.

Almost every guide or resource on Project Design I've ever read tells you to 'consult your stakeholders', almost none of them tell you how to actually do that -- how to functionally engage people when not everyone can be a decision-maker, and how to keep people engaged when realistically you can't do what they want.

In Part 2 Matt and I get into how to navigate these real-world situations. He shares:

  • How he 'closes the loop': His approach to maintaining stakeholder engagement even when you can't incorporate their input.

  • Why you should cook your projects, not bake them: How rigid, detailed plans often become straitjackets that hurt implementation (and what to do instead).

  • The people principle: Why human dynamics - not templates or PowerPoints - determine whether your project succeeds or fails.

If you're tired of project design feeling like some abstract theory or a bunch of buzzwords, well I can't promise that this will solve all your problems. But I can say that Matt gives his honest take on what has worked and not worked for him IRL, and I really think you will walk away with some useful insights.

The bottom line of all this: Projects are implemented by people, not plans. Design accordingly!

Episode 3

What happens when the people closest to the technical work can't make the final design decisions- but also can't get the feedback they need to make good recommendations?

In this episode Ken Wilkins takes us inside the world of FDA-regulated medical device development, where design decisions involve life-or-death stakes, regulatory gatekeepers, and technical constraints most of us never think about. Working on a wearable defibrillator, Ken's team faced the challenge of designing for not just their users- but also a faceless regulatory agency that is not exactly speedy in providing feedback.

Part 1 explores how design actually happens when you're operating in a highly regulated space: the tension of needing to make decisions without timely feedback, the complexity of coordinating teams on completely different development cycles, and what it takes to think strategically about trade-offs when you can't build everything.

If you've ever felt stuck waiting for stakeholder input while somehow being expected to deliver the 'right' solution, this episode is for you! The constraints might differ across sectors, but the tension between authority, information, and decision-making is universal.

In most organizations, you plan first, then build, but what if we plan to build first and design later?

Welcome back to Part 2 of the conversation with Ken Wilkins. In Part 1, we heard how Ken's software team navigated FDA regulations and the tension of needing approval without getting timely feedback. But Part 2 digs into something even more fundamental: what makes a design process actually work?

Ken explains how software's quick prototyping cycles create a unique advantage: you can build something, see how it works, and then loop that learning back to improve your original design. His team transformed a narrow fix-this-one-thing directive into a sustainable framework that would make future work easier. Instead of creating one-off patches, they built a general solution the FDA could approve once and apply to similar problems going forward. But this only worked because they had a project manager who listened when they said "we need to change the scope."

Here's the catch: this kind of bidirectional design process—where what you learn during implementation can actually reshape the design—isn't the norm. In many organizations, whether you're dealing with FDA regulations, donor requirements, or just organizational bureaucracy, the design gets locked in early and you're stuck with it. Ken talks about what he sees as the gold standard: processes that people actually want to follow because they make work easier, not harder.

If you've ever felt like your team is doing good work and then awkwardly jamming it into a process after the fact or wondered why it's so hard to shift direction even when everyone can see a better path forward, this episode gives some insights into how software design practices might offer some solutions.