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Website Challenges - Websites are Hard!

Most people vastly underestimate the work needed to create and maintain a great website. Building an effective website needs consistent focus, but many companies struggle with this. From content creation, to metrics, to technical challenges, to team building, a site takes WORK to get right, and keep it running. Does this sound overwhelming? At times it is, but it's worth the effort. With careful planning, clear ownership, and focused investment in both content and technology, you can build a site that converts visitors into long-time customers.

The Challenge: Your Website Is Never Done

It's easy to think that once a website is live, the hard part is over. That's a mistake.

Too often, especially in larger companies, websites are built without thinking about the future. Someone who doesn't understand how the web works approves the site, and it launches. Now there's a website, but it might not be what anyone really wants. Or, they see competitors making changes and want their site to keep up.

But one of the most common website challenges is that sites were not designed to change and grow.

Now everyone is in a panic! Companies spend extra money to fix the site quickly. Marketing teams are stressed because they have to make changes, but the site wasn't built to be flexible. An agency is found and is well-meaning, but they miss key deliverables that were not communicated clearly because things were so rushed.

While discussing the challenges of great websites, remember this: Websites need constant care.

New articles and videos need to be created. Software needs to be updated to keep the site secure and working fast. And as your audience changes, the website has to change with them.

Think of it this way: A website is not an event, it is a conversation that goes on as long as you have an audience. Launching the site is just the beginning. The real work is keeping the conversation healthy and strong.

1. Telling Great Stories Takes Time (and Executives Don't Like to Wait)

Great content takes great effort

Your website is a work in progress. It needs attention every day to stay successful. The web team will be busy updating content, responding to changes in the market, and learning more about what your audience wants today *and* tomorrow.

The content team keeps people coming back with fresh articles, videos and infographics that show you are a reliable and trustworthy organization. But, creating this content takes effort, time, and money. Not only does the content need to be excellent, but it also needs to be shared or promoted in the right places so your audience can find you.

Even the largest companies struggle with this work and keeping focused on the work that brings success.

Not everybody is good at creating content

One thing I learned working with talented content marketing teams is that I'm not one of them! I'm not an amazing writer, and I don't have a natural talent for website design.

I can do these things, but they're not my strong suit.

It's easy to underestimate how much work goes into a successful website. To be effective, your content needs to be clear, connect with your audience, and be updated frequently.

Need proof? Take a look at how many company blogs start strong but then fade away after a short time. Many people expect instant results and think of building a website a single event, rather than a continuous process.

I'm not a content marketing expert, but I know the technical side of things.

Measuring success is a pain

Google Analytics might make it seem simple, but figuring out how well your website is doing is actually quite hard.

Sometimes it's easy to see if people are buying your product. But often, customers take a long time to make up their minds. They go through several steps before they choose to do business with you.

So, instead of just one big success measurement, you need to track a bunch of smaller ones. Did people sign up for your email list? How many pages did they view? Did more people find you through social media?

This means your website's success isn't one straight line. It's more like a chess game where you try different strategies to reach your audience. You also have to deal with challenges like competitors, privacy rules, technical problems, and the constantly changing world of social media.

Summary: Why is creating content difficult?

Weren't you listening? Let me break it down:

  1. You have to keep creating content every day. There's no break when competitors are publishing all day and audiences are looking for new information.
  2. It takes talent and experience to make great content. You can't sit down and type some stuff. You need to understand the craft, know the audience, and work at it.
  3. It is difficult to measure success. In fact, it's impossible to measure success if you don't even know what you're trying to accomplish...which leads us to the next section.

2. Too Many Cooks in the Website Kitchen

A great website needs people with different skills, but there should be one person in charge.

Too often, a site is managed by a "website committee" or "center of excellence" or similar bureaucratic group. This is more often true in large companies. This managing group may have meetings every few months to go over goals and but often sends "urgent" requests to change things on the website at any time.

This committee approach leads to several important problems:

Who sets the priorities?

Each committee member has their own to-do list for the website. These lists get very long and often contain multiple "top priority" items.

So, who decides what gets done first? The committee might set a list, but the team doing the work may not have been consulted. Website project management is often formally in place, but organizes work at the whim of the website committee. This means the top task could take months, while several smaller ones could be done much faster.

On top of that, new "urgent" requests come in all the time, and the committee usually approves them to be immediately addressed without asking for the impact on the other in-progress work.

This means the team working on the website ends up deciding what's actually a priority. The committee thinks they're in charge, but they've given up control without realizing it. The team finds ways to "make things work" which may or may not be the best result and answer for the organization.

The worst part? The website team is blamed when things don't go according to plan! The team is probably already overworked and rushing, then they're told it's not good enough.

The web team is simultaneously asked "why did the urgent request take so long?" AND "why didn't you finish all the work we talked about in our last committee meeting?"

This happens because the list of priorities they were given wasn't clear, kept getting changed, or maybe even had conflicting goals. It happens because the committee interrupts the promised work schedule to change things. It happens because there's no clear owner and the committee will fight against having one owner.

Flip side: What does success look like?

Committees like to think they make clear decisions, but that's not always (rarely?) true.

Because everyone gets a say, website goals tend to get broad and vague. Instead of a sharp focus, you can't judge if the site is working well.

Most committees rely on simple numbers like page views or sales. That's good to know, but it doesn't help you improve the site!

You need to understand how visitors use the site from start to finish and track what actions they take along the way. But if the goal keeps changing – fix one thing this month, change another part next month – you don't have time to learn how to _really_ make things better. You fix what the committee asks for, but don't look at the bigger picture.

One Possible Solution:

Most big organizations don't have a single person responsible for their website. To improve the site, it needs to be treated like a product with a clear owner.

That owner would still work with others who contribute to the site, such as representatives who would have been on a committee. The site owner sets priorities, helps the web team stay focused, and finds the best ways to measure website success.

3. Who Are We Even Talking To?

Organizations often skip research as they try to do too much at one time. Given that organizations have a limited pool of money to spend on the website, competing priorities dissuade from investing in audience research.

Research costs money, and everybody prefers to assume they "know their audience" and spend the money on content and code...expecting that it will "work" for the "audience" the "know". The fallacy here is that getting more features or content on a site is not the same as delivering what audiences want most.

The same goes for other practices that create great sites, but don't advance a committee-based management style. There is often a nod towards a "brand" style guide, but there are no design systems. Focus groups sometimes get funded to help solve a specific problem, but rarely is there an investment in the end-to-end customer journey. And so on.

There are plenty of visible side-effects:

  • Confusing menus: the menus in the nav bar often reflect the company's internal organization (i.e. one nav for each sitting member on the committee)...and not the steps the audience would follow to accomplish their goals
  • Uneven language and/or tone: Each committee member has *their* team write copy that reflects how they speak to the rest of the business using jargon of their expertise. As such the website feels fractured as visitors move between sections owned by different units.
  • Design Clashes: Much like with uneven language, committee members may insist on specific designs that they believe are most effective. Often, this can also lead to a bizarre 'design escalation' where a flashy element forced on one part of the site is then mandated to be rolled out everyplace. (I hope you all like gigantic uncompressed hero images!)
  • Competing calls to action: The worst - multiple newsletter sign-ups that overlap. Multiple newsletters for a large organization make sense, but only when well managed. The same goes for contact forms, duplicated data entry (who loves uploading a resume, then typing it in too?), and more.
  • Outdated content: When one committee gets little out of the website, they neglect their content and area. Additionally, because each unit "owns" their copy, there's no singular group who audits and maintains a refresh schedule. The site slowly drifts and gives the perception of being unreliable (or worse, that the organization is unreliable!).

And with all this, it goes without saying that things like SEO are going to suffer because these require a coherent, unified approach to be successful. If a unit is letting their content go stale or is adding a million tiny press-release style posts every day, SEO results will be ugly.

The only solution is to do research and test why audiences are coming to the site. Don't create a huge section on some focus area is nobody coming to the site is interested. (Like, I don't have ANY idea why so many sites still have executive profiles. The only people likely to be interested in them are the executives themselves). Get a solid handle on what the audience needs and DO THAT.

4. The Tech Behind the Scenes is Complex

"I've used WordPress. This should be easy."

Sadly, no.

Websites are not Microsoft Word. Off-the shelf web hosting offers limited feature choices and customization options.

Custom websites that stand out are a whole different story. The same website can look completely different on a tiny phone screen compared to a giant desktop monitor.

A modern website can hide a complicated system of technologies underneath a polished surface. Features like online shopping, customer accounts, or connections to company databases require serious technical skills to build and maintain. Plus, the website needs to be designed for phones and tablets, as well as be secured against hackers. And, to wrap it up, website maintenance where software is patched or upgraded is also real work that needs to be done.

Websites also need to be:

  • Fast: Research shows that the longer people wait for a website to load, the more likely they are to leave.
  • Reliable: Any kind of error message confuses people and makes them lose trust. They might give up and go somewhere else.
  • Findable: Technical problems can prevent search engines from understanding your site or reduce its importance in search results. If people can't find your site, it's basically invisible.
  • Accessible: People with disabilities use screen readers and other tools to access websites. The website needs to be designed with them in mind, and it can't have too many moving parts that make it difficult to use.

All of these things take expertise and ongoing effort. But because these aspects aren't as obvious, they often get less attention and resources. Teams, whether they're managed by a committee or not, rarely discuss these 'invisible' parts of the website as much as they do the features that are front and center.

Of course, this doesn't mean you need the absolute fanciest technology in the world. But neglecting the basics – those things that affect how visitors experience the site - is just as bad as having outdated information on the site.

What can you do? If you're in charge of the website, try using it on a slow connection (turn your WiFi off!). If possible, test the site on an older, slower phone or tablet. See how it performs for yourself. If it's slow, find out what it takes to speed it up. If the menus and navigation are too complicated, especially on a mobile device, look for ways to simplify things.

Oh, and one more thing: leave your developers alone when they're working! Coding is like writing. It requires concentration, and interruptions make it hard to get back in the groove.

5. Finding (and Keeping) the Right People is TOUGH

People generally want to feel they are effective at work. They want to see the results of their work. They don't want to fight to get things done.

Sadly, many work environments create obstacles that make it difficult for employees to feel effective.

Worse, there's the paradox of "lowering productivity by adding people". It makes intuitive sense that when a person leaves, a team has fewer people to get work done.

However, when we add people (especially a large number at once), the team often slows down. The new person needs help getting into systems, learning workflow, asking questions, and so on. This is especially bad with new programmers, who often need few months to get really comfortable and productive with the code.

In general terms, the key struggles building and maintaining a high-quality web team are:

  • High demand for talent: Skilled web developers, designers, and content specialists are in high demand. Often, the skills are not industry specific, so talented people can look across a wide range of employers. This creates a competitive market, making it harder to find the right people at the right price.
  • The need for a wide range of skills: A great web team needs people with diverse expertise – front-end development, back-end development, UX design, content writing/strategy, SEO, and more. Finding individuals who are strong in multiple areas is rare, and assembling a balanced team is a puzzle. It's even harder when finding people who work well with others, and don't act as if "their part" is more important than others on the site team.
  • Technology changes rapidly: The web landscape is constantly evolving with new frameworks, programming languages, and design trends. A good web team needs to be adaptable and willing to learn new things to stay relevant.
  • Unrealistic expectations: Management sometimes underestimates the time and effort required for good web design and development work. This can lead to unrealistic deadlines and pressure, causing burnout and low morale.
  • Lack of clear career paths: In some organizations, web team members don't have a clear path for advancement. This can make them feel like their work isn't valued and lead them to seek opportunities elsewhere. This is especially bad when developers report into Marketing or content creators report into IT.
  • Competition from tech giants: Large tech companies often offer attractive salaries and benefits packages, making it difficult for smaller organizations to compete for top talent.

The solution? Respect these challenges and ensure that the team is shown the respect of any other group. Make sure the team has a clear set of goals and can request the resources needed to be successful. Share metrics with the team so they can celebrate successful improvements and also help solve problems that might not be apparent to others.


Building a remarkable company website requires determination and a long-term perspective:

  • Success Takes Time: Embrace the fact that a content-fueled website is a marathon, not a sprint.
  • Set a Clear Goal: Decide the website's primary purpose and keep it top of mind.
  • The Visitors are the Focus: Dig into user research to guide your content strategy and design.
  • Invest in Tech: Budget appropriately for the technology your website needs to function.
  • Nurture Your Team: Show appreciation and invest in your team's professional growth.

The Bottom Line

People are often fooled that a website is easy to create or keep running. True website success follows from a clear strategy that is supported by consistent execution. The team needs to be focused, supported, and work prioritized so everyone can see the key results that are needed for audiences to click on a search result, then return later.