The Most Over-Configured Tools Teams Keep Fighting
Flexibility Problem: While flexibility in project management tools is appealing, it can lead to over-complication and inefficiency.
Customization Trap: Tools like Monday.com and Notion, despite their popularity, can overwhelm users with excessive customization options.
Heavy-Build Tools: Complex platforms such as Workfront and ClickUp require significant upfront investment to be usable.
Rigid Workflows: Excessive control in tools like Jira or Wrike can cause teams to circumvent processes, reducing productivity.
Human Pattern: The core issue with tools isn't the software itself, but teams' tendency to over-configure, complicating workflows.
Project management tools are often sold on the promise of flexibility — the idea that a platform powerful enough to handle any workflow will make any team more effective. But for many teams, that promise backfires. The more a tool can do, the more tempting it becomes to make it do everything. And somewhere between the custom fields, nested subtasks, and color-coded dashboards, the tool stops serving the work and starts becoming the work.
The problem isn't any one platform. It's a pattern that shows up across categories: teams given too much freedom build systems too complicated to use, and teams locked into rigid configurations find ways around them entirely. The tools that generate the most friction aren't always the worst tools — they're often the most powerful ones, used without restraint.
The Customization Trap
Some of the most popular project management platforms on the market are also the most frequently over-engineered. Monday.com and Notion are two that practitioners call out consistently — not because the tools are poorly designed, but because their flexibility invites excess.
Unlock for Free
Create a free account to finish this piece and join a community of forward-thinking leaders unlocking tools, playbooks, and insights for thriving in the age of AI.
Have an account? Log In
Marissa Taffer, Founder and President of M. Taffer Consulting, sees this play out regularly with Monday.com. She notes that "a tool like Monday or something where it's a little bit more customizable is great, but it gets overwhelming because there's so many things you can do with it that you give people too much freedom, they start over-engineering." It's why she gravitates toward tools with built-in guardrails: Asana, she says, "feels like it's that right amount of constraint."
You give people too much freedom, they start over-engineering.
Notion draws a similar critique. Matthew Fox, Sr. Project Manager and Operations Specialist at Fox Consulting, describes it as a tool that attracts enthusiastic adopters who then get lost in the setup process: "A lot of people love Notion, but Notion is like a candy store where you can do everything you want in Notion, but then you spend so much time getting it set up and not actually getting the work done." The configurability becomes the product — and the actual project work gets pushed to the background.
The Heavy-Build Tools
A separate category of tools doesn't just invite over-engineering — it requires it. Platforms like Workfront, ClickUp, and HubSpot's help desk offering are built for complexity, and organizations that underestimate the setup investment often end up with systems that are technically functional but practically unusable.
Melody MacKeand, Founder of Melody MacKeand Consulting, points to both Workfront and ClickUp as tools that demand serious upfront build-out. In her experience, "tools that lean really heavy in terms of build like Workfront require really significant onboarding and build out." ClickUp presents similar challenges — it "often requires a consultant to come in and do the build," and "where I have seen organizations go awry with ClickUp is that they didn't hire someone to help them build and they built in a less than ideal way."
Tools that lean really heavy in terms of build like Workfront require really significant onboarding and build out.
Enterprise-grade tools can push the problem even further. Yonelly Gutierrez, Senior Program Manager at Palo Alto Networks, describes her experience with Planview as a cautionary tale about what happens when a tool's interface outpaces a team's ability to use it: "It was terrible. I could not understand how to use that tool. And our manager had to like sit down with everybody on the team and show us how to use it... She would just do the updates herself whenever she needed to push a project along because we couldn't figure out how to use it." When a tool is so complex that managers start doing manual workarounds just to keep projects moving, the system has failed its core purpose.
Fox has seen a similar mismatch with HubSpot in agency environments. "There's one agency I've worked with where they love HubSpot," he notes, but "HubSpot has a help desk offering that is a terrible fit for agencies. It requires a ton of customization and ton of setup." Love for a platform's core product doesn't automatically extend to every feature it offers — and forcing the fit often costs more than it's worth.
When Rigid Workflows Become a Roadblock
Over-configuration doesn't only come from too much freedom. It can also come from too much control. When admins lock tools down with strict workflows and excessive process requirements, teams don't get more productive — they find ways around the tool entirely.
Jira is the platform most commonly associated with this failure mode. Ryan Gilbreath, Technical Project Manager at RTS Labs, puts the blame squarely on configuration choices: "I really do feel like it comes down to the way the Jira admin sets it up and the workflows that they have in place. If it's a very rigid workflow and I got to go do this and this to get access to certain documents or teams and it's slowing down the pace of momentum, I'm probably gonna go outside of Jira." The tool isn't the problem — the choices made inside it are.
I really do feel like it comes down to the way the Jira admin sets it up and the workflows that they have in place.
Wrike presents a version of the same issue, but with a different consequence. Julia Rajic, Chief Operating Officer at Point Blank, describes how fully integrating Wrike with highly detailed templates and rigid task structures gradually eroded her agency's ability to think and work flexibly: "I went from disparate systems and tools to fully, fully integrated where... It was to the point where people would say, I'm not doing it until I have a task for that." The structure that was meant to bring order ended up creating dependency. As Rajic puts it, "if it's too structured and if there's too much detail and there's too much reliance on a tool, then what it can do is it can stunt your ability to break outside of that."
When Creative Freedom Intimidates
Not all over-configuration comes from feature bloat or heavy admin controls. Sometimes the person running the session is the one who over-builds. Free-form tools like Miro hand enormous creative power to whoever is facilitating — and that power isn't always used with restraint.
Alexa Alfonso, Sr. Account Executive at Caylent, has seen Miro go both ways. "I think Miro can be," she says, when asked whether it falls into the over-engineered category. "It all depends on who's running the board and what they want to do with it... I've seen an overly designed, overly complicated Miro that people just got intimidated by... maybe the facilitator over-engineered it, which is kind of the beauty and the downfall of a tool like that, because you can kind of make it what you want." A tool that can be anything is also a tool that can become too much — and when participants show up to a board they can't navigate, the collaboration the tool was meant to enable disappears.
I’ve seen an overly designed, overly complicated Miro that people just got intimidated by… maybe the facilitator over-engineered it, which is kind of the beauty and the downfall of a tool like that
The Real Problem Isn't (Usually) the Software
The thread running through all of these examples isn't a flaw in any particular platform. It's a consistent human pattern: given the option to add more, teams almost always do. More fields, more automations, more structure, more boards — until the tool that was supposed to reduce friction has become the primary source of it.
The fix rarely means switching platforms. It means recognizing the moment when configuration tips from useful into excessive, and having the discipline to stop building before the system starts working against the people it was designed to serve.
Want more insights like these? Sign up for a free DPM account to hear from more experts like these.