Expert Advice from Lead Project Manager, Diane Samuelson
Starting a website project can be both exciting and daunting. While you're eager to improve your digital presence, you might also be concerned about potential roadblocks and challenges that could derail your timeline, budget, or vision.
To help organizations better prepare for website projects, we sat down with Diane Samuelson, Lead Project Manager at Yoko Co. With years of experience guiding clients through digital transformations and rescuing website initiatives from disaster, Diane has unique insight into what makes website projects succeed—and where they commonly go off the rails.
In this conversation, Diane shares practical advice about the most common bottlenecks in website projects and how your organization can prepare to navigate them successfully.
A conversation with...
Diane Samuelson
Lead Project Manager
Yoko Co
Yoko Co: Let’s say an organization is planning to redo their website. Where do projects typically go wrong, and how can we avoid those issues?
Diane Samuelson: Content, technical integrations, and people-wrangling issues. Those are the big three that I see over and over again.
With content, it's almost always underestimating how much work it takes. It's not just writing – it's organizing, gathering images, making decisions about what stays and what goes. I've seen so many timelines get stretched because the content piece turns out to be this monster task nobody fully prepared for.
Technical integrations, especially around AMS systems, can be particularly tricky. Getting reliable access and test users is often a struggle. And since we're working with third-party vendors we can't control, there's always an element of unpredictability.
Then there's the people side. When key stakeholders aren't available at the right time or higher-ups come in with top-down directives that contradict decisions already made in the project, that's when things can really get derailed.
Are there early warning signs that a project might be in trouble?
When every round of approval or feedback takes longer than anticipated, when there's misalignment of expectations about what's within scope, or when you have board members or executives who aren't involved in the majority of the process but have to sign off – these are all red flags that a project might be heading off track.
What many organizations don't fully appreciate is how interconnected these challenges are. For example, if your content creation falls behind schedule, it might push development into a period when key decision-makers are unavailable, creating a cascade of delays.
Is there any common thread that connects most project difficulties?
Finding time to focus on it. That's what organizations find most challenging when starting a project.
A lot of our clients are juggling a million responsibilities, and the website project is just one more thing on their plate. So naturally, when other fires need putting out, the website work slides down the priority list. Someone needs to be your champion who keeps this project moving forward, even when the day-to-day gets crazy.
You said that content can be a major roadblock. Why is this such a common issue?
I’d say content requires the greatest amount of time and energy, on the client side. It’s the single biggest wrench we see in almost every project.
Most organizations don't realize how much work goes into it. You're not just writing new pages. You're deciding what stays from your old site, what needs to be updated, what content should live where, and how it all connects together. It's like organizing your entire digital filing cabinet while also writing a book about your organization.
What specific strategies have you seen work well for content preparation?
The best way to prepare is to understand upfront that this will take significant time. Start inventorying your content early, even before the project officially kicks off. Figure out who in your organization can own different content areas, and be realistic about their capacity.
If you have limited internal resources, consider budgeting for copywriting support. Sometimes it's worth the investment to bring in someone who can help shoulder the content load, especially for those sections that aren't highly technical or specialized to your work.
We have several systems we need to integrate with our new website. What should we know before we start?
AMS integrations in particular can be challenging. These integrations often involve multiple parties - your team, our team, and the AMS vendor - which adds complexity to the process. Sometimes we're ready to move forward but are waiting on access or answers from the vendor.
So before the project starts, I recommend documenting all your current integrations and understanding exactly what data flows between systems. You'd be surprised how many organizations don't have a clear picture of how everything connects.
How should we prepare for working with external vendors during integrations?
It's helpful to establish your contacts at the AMS vendor early. Let them know about the upcoming project and get clarity on their process for supporting integrations. Are fees involved? What's their typical response time? Do they have a formal process for test environments?
Another tip is to identify a technical point person on your team who understands both your business processes and your technical requirements. This person doesn't need to be an IT person, but they should be able to validate whether an integration is working correctly from a business perspective.
And definitely build buffer time into your timeline specifically for integration work. Even with perfect preparation, there are almost always unexpected challenges that come up during integration testing.
How much time should we expect to commit to this project, and how do we manage that alongside our regular responsibilities?
A website project is definitely not something you can fit into the cracks of your schedule. It needs dedicated attention and prioritization.
It's not just about attending meetings. It's reviewing designs, providing feedback, creating content, testing functionality, and making decisions at key points in the project.
What's the best way to structure our internal team for a website project?
Make sure you have 1-2 people clearly identified on your side to lead or manage things internally. These people need appropriate authority to make decisions and, even more importantly, they need protected time in their schedule to focus on this work. If you're expecting someone to manage this project on top of their full workload, something will suffer, either the project or their regular duties.
Also try not to do other large projects simultaneously that use the same internal team. Trying to juggle a website redesign alongside a major event, a rebrand, and regular operations – all with the same small team – almost always leads to delays, frustration, and sometimes even quality issues.
A website project is definitely not something you can fit into the cracks of your schedule. It needs dedicated attention and prioritization."
Diane Samuelson
What mindset should we have going into this project to ensure it's successful?
Every website project has challenges, even the smoothest ones. It’s normal. Accepting this upfront helps maintain perspective when you hit inevitable bumps.
Be prepared for moments of tension or uncertainty. There will be points where you're looking at in-progress work and thinking, "Is this going to come together?" Give yourself some grace that parts of this are going to be frustrating or hard, and that's okay. Trust the process and your project team during those moments.
How do you keep a project focused on what really matters?
It’s helpful to focus on your users' needs rather than personal preferences. I've seen projects get stuck when stakeholders debate aesthetic choices based on personal taste rather than what serves your audience best.
Most importantly, celebrate progress along the way. A website project is a marathon, not a sprint. Acknowledging milestones helps maintain momentum and keeps everyone motivated through the challenging parts.
What specific things should we do before kickoff to make sure our project runs smoothly?
Start by getting your internal team organized. Identify your internal project leads. These people should have decision-making authority and dedicated time to focus on the project.
Take an honest inventory of your content. What do you have? What needs to be updated? What's missing entirely? Start gathering examples of websites you like, not just visually, but in terms of functionality and user experience.
What about project preparedness and scheduling? How do we all get on the same page?
Identify all the stakeholders who need to be involved and at what points. Create a clear decision-making structure. Who has final approval? Who needs to be consulted but doesn't have veto power? Having this clarity from the beginning prevents confusion later.
Look at your calendar for the next 6-12 months. Are there major events, busy seasons, or other initiatives that might compete with the website project? Plan around these if possible or at least be aware of potential crunch points.
Finally, have an internal conversation about expectations. What would make this project a success for your organization? What are the must-haves versus nice-to-haves? Being aligned internally on priorities makes the entire process smoother.
If you could offer one piece of advice to someone about to start a website project, what would it be?
Websites are, for lack of a better word, living things, which is actually liberating when you think about it. You don't need to solve every problem or include every feature in the initial launch. You can commit to getting your site to a better place now, and then improve and adjust and iterate from there.
When you approach a website project with an "all or nothing" mindset, it creates enormous pressure and can lead to decision paralysis. Instead, think of it as the next step in your digital evolution, not the final destination.
Your digital partner should be there to guide you through each stage, turning potential roadblocks into opportunities for collaboration and growth. The website you launch may not be "perfect," but it will be a platform that grows with your organization's needs.
Meet Diane
The Voice Behind the Projects
Fun fact: "I can't ride a bicycle. Never learned."
Claim to fame: At Yoko Co, Diane is known as "dianebot" who coined some of the company's most important phrases. "It depends" – the team's favorite answer to complex questions – and "people first" – a core part of the company's values – both originated with them.
Double life: When they're not managing website projects, Diane works as a professional voice actor, bringing characters to life in video games and animation. They’ve voiced deranged 80s-style radio commercials for a Stranger Things virtual reality game and specialize in accents and dialects.