What nobody tells you before you start

When I stepped into a digital content operations role, I thought the hardest part would be the technical work. Learning the CMS, understanding the publishing workflow, figuring out where all the content actually lived. That stuff was learnable. The harder part was something I didn't anticipate: walking into an organization that had its own history with its digital presence, its own set of workarounds, its own informal hierarchies, and its own firmly held opinions about what was wrong and who was to blame for it.

The biggest mistakes I see new digital leads make in their first 90 days are not technical. They're relational and political. Moving too fast on changes before building the trust to make changes stick. Diagnosing problems without understanding the context that created them. Arriving with a plan formed entirely from the outside and spending three months pushing it uphill against people who know things you don't yet.

The roadmap I'm laying out here is based on what I learned from running content operations and what I'd tell anyone stepping into a similar role: web manager, digital communications lead, content strategist, digital services coordinator. The specific context was managing a high-volume content operation where timing, accuracy, and cross-functional coordination all mattered. The patterns generalize.

Here is how to spend your first 90 days in a way that builds the foundation for everything that comes after.

Days 1-30: Listen before you diagnose

The first month is not for fixing things. It is for understanding the system you've inherited, including the invisible parts that don't show up in any documentation.

The content and systems audit

Start with the inventory. Before you can make good decisions about the digital presence, you need to know what's actually there. This means:

This audit is not about judging what you find. It's about building an accurate map of the territory. You will find things that are surprising, alarming, and sometimes downright inexplicable. Do not immediately start fixing them. Add them to the list and keep going.

The stakeholder listening tour

In parallel with the content audit, start meeting with everyone who has a meaningful relationship with the website. Not just the people who own it. The people who depend on it.

In my experience, the most useful conversations in the first month are with:

The person who had the role before you (if accessible). What did they spend most of their time on? What did they wish they'd had more time for? What did they avoid, and why? You will learn things about the organization's history with its digital presence that nobody else will tell you directly.

Department heads or managers who are heavy content contributors. What do they feel is working about the current website? What frustrates them? What requests have they made that haven't been acted on? Listen carefully to the frustrations. Not because they're all valid (some won't be), but because they tell you where the friction points are and where your credibility can be built by solving real problems.

The people who actually receive the complaints. Customer service teams, front-line staff, anyone who talks to users regularly. Ask them what questions they get that the website should be answering. Ask what they tell people when the site doesn't have what they need. This is real-world usability research done in fifteen-minute conversations.

IT or infrastructure, if separate from your team. Understand the technical constraints before you make any promises. What's the CMS, and what can it do? What integrations exist? What change processes are required for anything touching the server or the domain?

Take notes in every meeting. Not just what people say but what they're implying. The manager who says "we've tried to update that section before but it never seems to happen" is telling you something about approval processes or resourcing. The IT lead who mentions offhand that the CMS is "on the upgrade roadmap" is telling you that the platform you're about to invest in learning may change. These signals matter.

What you're building in month one

By the end of the first month, you should have:

You should not yet have a strategic plan, a redesign proposal, or a list of things you're going to change. You have a map. The strategy comes next.

Days 31-60: Identify the quick wins and the slow problems

The second month is where you start distinguishing between problems you can solve quickly (and should, to build credibility) and problems that will take longer (and require organizational support to address properly).

The quick wins

Quick wins have two characteristics: they're visible and they're uncontroversial. Fixing a broken link on the homepage, removing a page that has been outdated for three years, correcting a factual error someone has been complaining about — these things cost you almost nothing and they signal to the organization that someone is paying attention who wasn't before.

From my content operations experience, the highest-value quick wins in the first 60 days are usually:

Outdated contact information. Phone numbers, email addresses, and staff names that refer to people who no longer hold those roles. These erode user trust every time someone encounters them and are almost always easy to fix.

Pages with no owner. The audit will surface pages that were created for a specific project, event, or initiative and then abandoned without being archived or removed. Every one of these is a liability — they may contain outdated information, broken links, or conflicting messaging. Get confirmation that they're no longer needed, then archive or remove them.

Broken or dead-end navigation paths. Menu items that go nowhere, links in the header or footer to pages that return 404 errors, calls to action that point to outdated URLs. These are visible friction for every user who encounters them and almost always fixable without any design changes.

Analytics baseline. If the analytics setup is incomplete, get it to a trustworthy baseline state before the end of month two. You cannot make credible data-informed recommendations without data you can actually stand behind. This might mean verifying that the tracking code is on every page, confirming that key actions are being tracked as events, or simply documenting the known gaps so you're not presenting bad data as good.

The slow problems

The slow problems are the ones that showed up repeatedly in your listening tour, that are clearly affecting the digital experience, but that can't be fixed by one person making changes in the CMS. They fall into a few categories:

Structural problems (the site's information architecture doesn't match how users think about services, the navigation was designed around the organization chart rather than user needs) require user research, design, stakeholder alignment, and development time. Don't try to solve these in the first 60 days. Diagnose them clearly, document the evidence, and begin building the case for addressing them properly later.

Process problems (content approvals take six weeks, there's no documented workflow for publishing, five different people have to sign off on every news post) require governance and organizational change, not CMS fixes. Document them. Identify who has the authority to change them. Begin those conversations carefully.

Resource problems (there isn't enough capacity to maintain the site at its current scope, the CMS is too technically complex for the people who are supposed to use it, the content is three years out of date across 40% of the site) are the most sensitive to raise because they often imply that what exists isn't working, which can feel like criticism of the people who built it. Build your evidence base carefully and frame these as forward-looking resource needs, not a post-mortem.

Days 61-90: Build the strategic case

The third month is where you start presenting — to your manager, to the governance council if one exists, or to whoever owns digital investment decisions for the organization.

What you're presenting

Not a redesign. Not a technology recommendation. Not a list of everything that's wrong.

You're presenting a prioritized picture of what the digital presence is doing well, what isn't working for users, and what the three most important things to address are, with evidence for each.

The structure I've found most effective:

What the data shows. Summarize the analytics baseline: what traffic looks like, where users are concentrating, where they're dropping off or leaving without completing tasks. If you've been able to do any quick user research or review of support request patterns, include that. This section should be factual and focused on user behavior, not evaluation.

What stakeholders said. Synthesize the listening tour findings into patterns. Don't name individual people or departments; reflect the themes. "Multiple departments mentioned that the approval process for publishing routine updates takes longer than the update window, so time-sensitive information sometimes goes live after it's already outdated" is more useful than "the planning department said the process is slow." Themes feel organizational. Named complaints feel like you're reporting on people.

The three priorities. Pick three. Not ten. Three specific, addressable things that have a clear user impact, organizational support, and a realistic path to resolution within the next six to twelve months. For each one, name the problem, the evidence, the proposed approach, and what you'd need (resources, authority, time, organizational decisions) to address it.

The conversation that matters most

The most important conversation in the first 90 days is not with your team or your stakeholders. It is with whoever you report to.

You need to understand, explicitly and directly, how they define success for the digital function. What do they think the website should accomplish this year? What are they being measured on? What would make them look good to their leadership? What problems are they currently being blamed for that the website is contributing to?

This conversation tells you how to make your strategic case land. A director who is under pressure to demonstrate digital accessibility compliance needs a different first-90-days presentation than a director who is focused on service channel shift (moving more transactions online). The work might be identical. The framing and the metrics you lead with are entirely different.

I've seen new digital leads undermine themselves by delivering technically excellent strategic plans that were completely disconnected from what their leadership was prioritized on for the year. The plan was right. The timing and framing were wrong. The result was a shelf document.

The things I'd do differently

I spent too much of my first months in a high-volume content operations role reacting. The volume of incoming requests and the speed of the publishing cycle meant that strategic work kept getting deferred in favor of the urgent. By the time I had built up enough understanding of the system to start making structural improvements, some of the quick wins I'd missed early on had become deeply embedded patterns that were harder to shift.

If I were starting over, I'd protect two hours per week in months one through three as non-negotiable audit and strategic thinking time, blocked in the calendar and defended from reactive requests. Not because the reactive work isn't important. Because the strategic work doesn't get done unless you force the space for it.

I'd also be more direct, earlier, about what I was doing and why. Teams respond well to "I'm spending the first few weeks building an understanding of everything before making changes" when you explain it. They fill the silence with assumptions when you don't.

The audit and listening tour are not just information-gathering exercises. They're trust-building exercises. The web lead who spent a month talking to every department before changing anything is not the threat. The web lead who arrived and started restructuring the navigation in week two before understanding why it was built the way it was — that person is the threat, regardless of whether the change was technically correct.

A 90-day checkpoint framework

At the end of your first 90 days, you should be able to answer yes to each of these:

Clarity on the landscape

Credibility built through action

Strategic foundation in place

The goal isn't a perfect score. It's a honest self-assessment of where you are strong, where you have gaps, and what you're going to do about the gaps in the next quarter.

Building a digital function from scratch or stepping into a role that needs a reset? Get in touch for a structured 90-day onboarding plan tailored to your organization's digital maturity and your specific mandate.