Why Are People So Picky About Project Management Software?

Why are people so picky about project management software? The cult of the project management tool unmasked.

If you’re a consultant, you know the song and dance: You onboard a new client who’s acquainting you with their processes, and you’re quasi-immediately introduced to their project management software preference.

You’ll hear a lot of managers and owners stating that their teams ‘love’ a certain tool. There are usually at least a couple of people too that are so dialed into the solution, that they can make it do incredible things you didn’t even know were possible.

This is a taste of the cult of the project management tool. And if you’ve worked on multiple small teams in the last 5 years, you’ll know exactly what I’m talking about:

People are ridiculously picky about these tools with cult-like loyalty.

You have your Asana purists, of whom there are a lot, since their market presence dominates the small business sector.

Notion, ClickUp, and Airtable also have their own proverbial cult followings. Like Asana, Notion, and ClickUp are currently among the market’s top performers.

So, why are people so picky about their project management software? Why do certain platforms bother us and others not? Where do the more subjective preferences come from?

Before we get to answering those questions, first, if you’re a team member or consultant you’re most likely going to be using a software platform selected based on the preferences of the project manager, owner, operations manager, etc. 

The person in charge is ultimately the decider of what specific project management solutions the team will use and how they’ll use them. 

Not unlike an archetypal cult, one person’s preferences usually carry more weight than the others when it comes to the selection process.

Because I’ve worked on small teams for over six years, I’m all too familiar with everyone’s proclivities for specific solutions and even outright disgust for others.

Here’s a historical scenario to give you a taste of the cult of the project management tool:

I can remember this one marketing project manager I worked with who was obsessed with ClickUp. His type-A, detail-loving, and self-admittedly hyperactive brain loved dialing down into each and every task that ever popped into his mind.

He didn’t just like using ClickUp, he loved it.

Of course, as the consultant for the client, I had to use this tool, too, as did everyone else on the team. I personally hated working in ClickUp with him. He got too into the weeds with the task details and dependencies. 

There were lists upon lists and enough labels to make your head spin. By the end of the project, I was totally exhausted and mentally done with the whole thing.

This is not at all an atypical scenario in the life of consultants and creatives, who after a few years will be well-versed in the Trellos and ClickUps of the world. 

But what’s happening now? Teams are rebelling. 

Based on their cumulative experience, they’re keeping the tools they like, and it’s often causing severe SaaS sprawl to infect entire organizations, which could be using a dozen tools to manage projects at any given time.

The Wall Street Journal reported in May this year that CIOs are having trouble stopping the bleed because users have such strong preferences towards their favorite project management tools. 

In the piece, Mansoor Basha, CTO of Stagwell Marketing Cloud, talked about “sub-sects and cults” forming around different project management software. Teams are uniting behind what they want to use. 

Hence, the cult references.

At the end of the day, here’s why I think people are so picky about their project management software and why different tools develop their own cult-like followings:

Different industries learn different ways

Certain project management software tools are targeted to specific industries, which can win them big points with users. Some just happen to catch on in certain niches when the solution adds a lot of value and has features to support those specific business models.

For example, many service businesses, especially IT services, will choose a PSA solution as their project management software.

These are specifically designed for professional services and therefore have out-of-box capabilities like automated invoicing, CRM integration, etc to cover the financial aspects of projects. 

Those who work in professional services, therefore, are more likely to favor one of these tools, something like a Jira or a PSOhub.

In other areas, media companies and content publishers I’ve seen lean toward Airtable and Asana. I notice that software startups are prone to Teams. Although admittedly, all three of these and the most popular project management tools have more or less the same features. 

Price point

Budget is a big factor when any size business is deciding on a project management tool. And these days, freelancers, solopreneurs, and small teams can get a decent amount of functionality from free versions. At least enough to manage task lists, set reminders, and attach documentation.

Enterprise and growing businesses need more data storage and more capabilities to adequately manage the larger flow of customers and cash. They may be more used to more sophisticated tools.

But for most small businesses, the pricing for project management software won’t vary that wildly. The main players all hover around the same price per user per month. 

Still, free versions and free trials from some of the world’s most popular project management tools have let millions of people get their feet wet with different platforms, helping to see what’s available at the lowest price points. 

Often, these people will be more reticent in the future to accept a new solution if they feel it isn't enough bang for the buck, as they’ve had experience with so many low-cost options. 

Subjective interface preferences

I think that any software’s interface, especially when using it five days a week, plays a big part in why people will viscerally like or dislike a project management tool.

Some of that can be easily explained. For example, PSOhub is designed with HubSpot users in mind, so it looks and feels like HubSpot. HubSpot users like this setup. 

Slack is another good example, with its simple layout that displays photos of the people you’re chatting with and different channels for different streams of information. For me, Slack’s interface is a peaceful, organized place.

But that’s what I think. Different people prefer different colors, fonts, layouts, and language to suit their moods. 

So a lot of the pickiness around project management software is really subjective, and as I mentioned earlier, will mostly depend on what the person in charge wants for the team(s) involved.

Intuitive or not?

People flock to what they perceive as most intuitive. Teams don’t want clunky solutions. 

They don’t want to spend their time watching help videos and chatting with customer support about how to set up automation, for example. 

It turns out, that intuitiveness, specifically when it comes to a digital interface, is based on the recognition of similar things, i.e. the more you have experience with project management tools, the more you’ll think the next tool you use is more intuitive than the last. 

From a 2007 study on perceived intuitive use via interface:

Two initial experimental studies revealed that prior exposure to products employing similar features helped participants to complete set tasks more quickly and intuitively, and that familiar features were intuitively used more often than unfamiliar ones.

This supports the subjectivity angle further, and it helps make sense of everyone taking sides in this battle. What feels intuitive to one person won’t necessarily render the same effect on someone else because this is a subjective perception based on the experiences of each.

The #1 Reason People Are So Picky About Project Management Software

Yes, people in different niches lean toward different project management tools. And yes, price, subjective interface preferences, and level of intuitiveness are what make these tools such a picky subject.

However, none of these comes close to the #1 reason people are so picky about this, to the extent that different tools can now have different cult followings within the same organization.

No, the #1 reason people are becoming zealous with their favorite project management tools is way more simplistic:

People hate change.

We do. Humans are by and large afraid of change, uncomfortable doing so at the very least. 

People are picky about their project management tools because they don’t want to switch. That involves change, learning new things, and a time investment in adapting to a new solution.

Let’s face it, most don’t want that. For better or worse, most of us would rather go with what we know works versus onboarding a whole new solution. 

A lot of us get deep into certain platforms to really customize them for everything we want. When we have to change, it can feel like a slap in the face.

Perhaps I’m incorrect, but when all is said and done, I think ultimately people are so picky about project management software because most of us by now have had experience with at least two, and gotten good at at least one.

Returning time and again to those old favorites in lieu of finding the next best thing is comfortable; it’s just human nature. And it explains why some project management tools reach cult-like status in organizations where users cling on and sometimes won’t let go.