What is the Daily Sprint?

A podcast answering: how do you stretch your thinking, push new ideas, and deliver design excellence into your products?

What is the Daily Sprint?

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Welcome to the Daily Sprint, where today is a great day to design.

This is a podcast for product designers who want to stretch their thinking, push new ideas, and deliver design excellence into their products one day at a time.

I'm Darrell Estabrook, 30 years into UX product design. Yes, since the web was young, and a lot has changed since then, but we're just still getting started.

I'm also the founder of designing a platform for product designers who want to design with a why. Through content coaching and consulting, I'll help you lead with design wherever you are, and begin transforming your products, teams, and companies from the inside out.

Find out more and get on board with a free newsletter at designy.com. That's “design” with a ”y” dot com


So welcome. I'm glad you're here. This is episode one, which is always a good place to start. Number one.

So what is the Daily Sprint?

I love thinking about this. The Daily Sprint. It's the time each day you have to grow your talents and put them to use. We can talk about your whole life as a daily sprint, but I want to focus on product design specifically. And what can you do today to grow as a product design leader.

Did you ever think about that, you are a design leader? The question is: are you leading? And if not, you can start, and I can show you how, a little at a time.

But if you are a leader: can you lead better? Of course, the answer is yes, you could always lead better. We could always do better.

So that's what we're going to explore through all of these things. The sprint is really a great concept.

If you're familiar with product design, obviously agile is the term, even if it's agile in name only, I love the fact that it's two weeks, it could be four, it could be one, but two weeks to deliver working software.

This kind of thinking is very awesome. Because I know if I'm left to my own devices, I tend to churn instead of getting something out.

Time boxing really works, it creates an accountability because you have to deliver something. It forces me to make decisions, and then in doing that, I'm going to see results and pivot right away. I think it really comes together well for teams because there's so many different individuals. So, putting them in that time box and thinking in sprints really works well.

But if you take that idea and say, we live only one day at a time. Why not look at your professional development as a daily sprint?

So there’s a verse I like to reference, and it says, “So teach us to number our days, that we may apply our hearts unto wisdom.” And that's in Psalm 90:12.

The idea of numbering our days, learning that we have a day at a time, and that we really need wisdom in order to make good decisions in those days.

You can't change yesterday. That's gone. We can learn, perhaps, from that. We can't predict tomorrow, or even guarantee tomorrow, and you can only decide things for today. So the wisdom really helps.

The decisions that you make today will have results one way or the other. I wish I had that kind of wisdom when I was starting out in those early days. I said 30 years...

So in 1996 the web was not even a commercial thing. There wasn't anything really of substance, but it was exciting.

But as far as a product designer, there's no UX processes. There weren't any UX patterns, and there's definitely no path towards developing UX skills than just doing it and figuring it out.

So I designed and engineer my first web app. I'd call it a web app because it was, it had all the parts that we're familiar with today. I used Photoshop 4, which is probably like, what is it, version 30 something now. And Active Server Pages from Microsoft. You don't even have to know what that is just to know that it was clunky. And Access databases—we still have Access today.

And this was a web app for people in my local area of Richmond to view and download those value coupons (I wish I should have had one here). Those rectangular flyers that promote cleaning your gutter and mowing your lawn and going to a restaurant, that sort of thing.

This stakeholder ran this business, wanted to get on the web. So I built this system for him that people could look at the monthly coupons and then also scanned those coupons every month for him. So I had a batch of these paper coupons to scan in, and people used it.

It wasn't earth shattering. It certainly isn't in Wikipedia, but there were real people that really used it.

Here's what I learned from that.

I needed a vision in order to even begin designing and coding this. So working with that stakeholder, business person, he didn't even know what he wanted to do, like the effects of it. He just knew he needed to get online. So we work together to clarify what would be the result.

Then I needed to know how people would use this. Not a lot of user testing, user access, but I used people that were around, who I had access to, and asked them how they would use this.

I needed a roadmap. And so obviously design and technical came into play, Photoshop. So static, you couldn't even edit the text. It was baked like the moment that you typed it in. So really committing there.

And then delivering these pages, not just for the end user, but also for a way to administer all these coupons, had to think through that.

And then to find out if people were actually using it. There weren't a lot of options for analytics. So I made a way to count the visits, and that was fantastic at the time. “Oh, another page view.”

But all of that process is very familiar to what we do today, there's a lot more technical hurdles, a lot more detail, people are a lot more savvy with how they use their devices, but the underlying core of product design is there.

And what I think is more fascinating is that's not just software that made that process come to be. It was always around in creativity where there's engineering and the building of something together that requires design and engineering.

I think architecture is like one of the big examples of that, but this process is always been around.

And I don't think it's going to change, even with AI coming about, there's so much unknown about AI, that it's just changing so fast.

But the knowing this core, knowing how to think through these problems is going to be one of the superpowers that the next generation of product designers are going to need to hold onto, even with that new technology.

And the other thing I learned is that the impact is always real. I think it's awesome that we want to create products that we make a design decision and it affects millions of people for the better. And a lot of times it does. It's not direct.

But the people that you work with, every day and the products you work on are the people that is, this is your audience. They're the ones that you're making an impact on.

The people you work with are also paying attention to what you do as a product designer. So they're saying this is how design is done.

And that's where you're the design leader, where you actually have this role and have an opportunity to really demonstrate the value of design just by doing and doing your job well.

That’s some of the stuff we can discover in this daily sprint that we're in.

Whatever you're doing now, the question is, can you do it even better?

There’s so many different aspects of this.

I think communicating with stakeholders more effectively, that's always a challenge of working with non-designers.

How do you communicate, what you're thinking and how do you think in design terms, and what they're looking at and how do you handle their comments? That's a big thing.

Getting clarity on the purpose of each and every feature. That's that's huge. Why are we even building this? What's the point? What's the outcome we're going for?

And then I think actually crafting the design solution. I always looked at it as artistry, because we're dealing with composition, presentation, color, typography, all of these things come into play and really affect usability and all of that. But we're also dealing with now dynamic data and active data in the case of AI, just really unpredictable in a static sort of sense.

So all of that comes into play.

We're in a very unique role, and it's really exciting.

So, you know, you look at where you are now and you're like, well, I should have started sooner. I wish I could have learned this sooner. Maybe some are further down the path than others, but I always like to think of it as the best time to plant a tree.

So you have an apple tree. You want an apple tree. I wanna eat an apple now. The best time to plant the tree was probably 20 years ago, but the other best time is the plan it is today.

Because the sooner that you plan it, the sooner you're going to have that growing.

And when it comes to improving and becoming a design leader and all of that, that's the end goal, I think, for all of us becoming better in this craft in this job, but you don't have to revolutionize your process overnight.

And starting with at least that vision of where you want to be and making changes every day, practicing these things.

That's really going to start you down that path. And we'll discuss a lot of these things over the course of this podcast.

But today is the day.

I know if I had a mentor 30 years ago, I'm sure I would have skyrocketed because the way I ended up going through this was the long and windy way.

Which isn't bad. I don't regret it. It's the way that I had. It's what was available at the time. And the good thing about that is I learned a lot of things that don't work.

So even in the case of stakeholders and and presenting designs and getting feedback and things like that, managing a team.

Yeah, there's things that don't work. There's things that did work. And to be able to come alongside someone and point out the things that they're working on in real time, day to day, that's invaluable.

And that's something that I actually do. I do for product designers, is come alongside. And that's why I started Designy.

So it's really to coach and mentor product designers and even product team leads in this idea of design leadership.

And it's design with a “why”, right?

Designy, design with a why, because that why is huge.

It's true for every day, operation, but professional development, it's really where you can cut through all of this clutter.

The thing when you're looking at your product, do you ask why does it exist? You should know why it exists. But then digging deeper.

Do you know why that feature exists? Why do we have it? What is its value? Are there other features that we should be doing for a greater value? Where are we going with this product?

And then I think even asking why about placement and position and presentation, like why is that button on the left versus the right? Is that just the UX pattern? Is this how it's always been? Or in this case, is it better to have it somewhere else even if it's not expected from the pattern?

It might be exactly where the user needs it.

All of this matters. I think all of the whys matter and getting really good at identifying those questions, asking those questions at the right time is really what will demonstrate the value of design.

And I think it's why is foundational, right? No matter what the process is, no matter who the stakeholders are, or the noise in the design field, there's a lot of noise out there. AI is out there. But thinking in terms of why, that's where you'll start to actually affect those around you. And they'll start to think on purpose about things instead of just reacting by accident.


So as a bit of a takeaway, here's a quick exercise that you can do.

And this is part one, and we'll continue this as we go along, but pull up a notes app that you like to use, or if you have sticky notes. I know I have sticky notes everywhere. I've got them like writing on stuff. But a notebook, anything that you've got.

And I want you to write eventually write two lists. I've got two prompts for you.

And for each one of these, take about two minutes. We won't do it right now. You can pause and do it or listen to this again.

But the first prompt for the first list, write down as many things as you can in those two minutes: Things that slow me down in product design.

Just let it all out as quickly as you can.

If you do use stickies, physical stickies are awesome because you can just jot an idea, rip it off, jot another idea, rip it off. There's really physical kind of a thing.

And then the second list, the second prompt, are: Things I wish I could break through and do in product design.

So some of the things that you can't do right now that you just bulldoze those barriers down and you wish you could do it. Write that down. Think through these things. In fact, if you do this in two minutes, that's great.

Keep that and we'll come back to it in another episode.

But throughout the week or even day to day, keep those two things present, those lists. And as things come up during the day, write, write another thing down, like it fits in one of those categories. Because we'll take a look at those, and those can become the seeds of where you need to dig or you'd like to dig to get better to get stronger in product design.

And if you want to jump ahead and kind of go to the next level quickly, um, you can send them in to me, anonymous or not, I've got a form on my website, designy.com/ask.

It's a form for asking a question, but you can post this list up there. I'll take a look at it and we'll see what we can do with that.


So some of the ways that you can get involved with the daily sprint is subscribe, subscribe to this podcast, whatever you're listening to, whatever channel, platform, just go ahead, subscribe, follow, and stay tuned as we go on this journey.

And then send me the lists or ask any question you have about product design professional development getting stronger in your day-to-day work.

You can go to designy.com/ask and just ask a question. And I'll respond as I can. And if not, we'll talk through it in other channels.

And then while you're there, sign up for the free newsletter at designy.com. That's right, just go to “design” with a ”y” dot com.


So thanks for listening to The Daily Sprint today.

Remember, today is a great day to design with a why.

See you next time.