Why Nothing Ever Gets Done


I hope everyone had a great weekend, I certainly did. It’s finally starting to feel like summer, most of us have a long weekend coming up, and it’s my birthday on Friday.
As of recently, summers have also brought with them the new phenomena called “Summer Fridays”, where people are officially, or unofficially, allowed to log out of work after noon on Friday. Some companies are fully embracing it, for others it’s an unwritten rule, and for select employees it doesn’t really matter because they check out after lunch on Fridays anyways.
Regardless, companies have been using it as a recruiting and retention strategy to attract talent in an age where people are less likely to put up with work conditions that don’t match their lifestyle.
You know, the whole “We have a really good company culture” or “Summer Fridays are a great example of our good work-life balance”.

Offices Are Getting Quieter, But Not Just Because of Summer Fridays

COVID obviously accelerated the work from home trend, leading to many employees leaving the office indefinitely. And Summer Fridays has only made the offices feel more eerie during the summer.
But both of these have only compounded an increased quietness that was already building.
Why? Well, because employees have become less and less likely to participate and speak up in meetings. Especially, when it comes to highlighting risks and expressing concerns.
Here’s a few reasons behind it:
  • It’s easier. Speaking up requires you to explain and justify your thought process, and why you may disagree with the majority. Then you must be prepared to defend your thoughts if there are any questions. It has become easier to just not say anything, even if you don’t agree with the conclusion.
  • Highlighting risks can be risky in itself. Many employees think that highlighting risks can put a target on their back, get them labelled as a “bad team player”, and lead to exclusion from future projects and thus poor career growth.
  • The water coolers are gone. With more people out of the office for the reasons I explained above, there are less informal conversations. Nowadays everything comes with a meeting invite, instead of bumping into someone and mentioning your concerns off the record.
Due to these reasons, it has become more common to have a team of “yes-people” who placate the project manager, and less common to find a group of critical thinkers who can challenge each other and innovate.

And CEOs Hate This

Obviously, the list of CEOs who have bashed WFH is well documented and growing, but what many people fail to realize is that the dwindling participation that I just outlined is the underlying reason why.
Executives love the quote “fail fast and fail often”.

Why do they love it? Easy, when you fail fast and often you arrive at the true solution quicker by learning from the mistakes, you end up sinking less money into the wrong idea, and you team innately becomes more collaborative.

But when your company has people who are simply placating because they’re scared to speak up, the project ends up going on for a really long time, you sink a bunch of money into the ongoing costs, and it doesn’t end up working in the end anyways because you didn’t address any of the concerns.

This is why big companies take years to complete projects that a small, familiarized start up could do in a month.

So, when you hear CEOs mentioning it, this is their concern and it’s a little bit more calculated than you may think.


Getting To The Point

I’m not the first to realize this either. Billions of dollars and dozens of companies have identified this problem and tried to create the next best project management software.

Monday.com, Smartsheet, Clickup, Slack, etc. have all been trying to answer the same question: “How do we bridge the gap between virtual and in office workers to create a centralized, collaborative, all-in one software that makes running projects easier?”

Using phrases that focus more on “efficiency” and “capacity”

In my opinion, they all suck.

And it’s because they’re all optimized for project completion. Good, bad, or indifferent each of these companies’ software is built to push projects across the finish line. Their performance metrics are based off how many projects were completed, instead of quality and success of the project.

So, here’s my idea. I think there should be a pessimistic project management software.

A software that can do the things that all the others do (sync timelines, create Gantt charts, etc.), but that specifically focusses on testing the idea to an extreme.

What does that look like?

I think it hinges on two main things:
  • Anonymity: People are more likely to provide critical feedback if they can remain anonymous, and none of the current software offers this. Enabling anonymous feedback decreases the implied risk for employees and encourage people to speak up, making a more battletested product.
  • Consequences: In this case “sorry” isn’t enough. This software would prioritize building in public, where every employee can look at every ongoing project and each member’s productivity. If you think people are nervous about voicing their concerns, just imagine how hard people would work if everyone could see who was the least productive on a team. I’m sure there are some HR/confidentiality considerations here, but you get the point.
It may sound counterintuitive, but nobody else is doing it. Like I said, most of today’s project management software is optimized for completion rates, not quality of product.

That is, if they even use software. There are a lot of companies that just have designated project managers, whose whole job is to make charts that look like this:

The people who push everyone to complete their portion of work but can’t actually do any of the work themselves.

I think there is a market for project management software that’s not the most efficient, but actually the most difficult to pass.

A brand where the motto is something like “if your product gets completed using our software it will 100% work.”


Speaking of project management software… I know I have been bashing some of them, but Planview  isn’t like the rest. Sure, they have great project software, but their bread and butter is their portfolio management software. Want to have a clean breakdown of each of your products, how they are positioned, and recent developments? Try Planview , they’re building the future of connected work.

Final Thoughts

Too many C-suite executives are focused on changing the culture using buzz words “work-life balance” and “Summer Fridays”, thinking it will help them hire better employees and in turn make their companies more productive.

But we all know that changing the culture is too hard. Nobody likes to talk about the “c-word”.

So, don’t. Instead of blaming or praising the work culture, we should look at the tools the organization is using to conduct work. Instead of calibrating the company culture, calibrate something much simpler: the project management process.

I think many people would be surprised at how changing something so small could create a big impact. Pessimists can be great critics, so instead of putting that responsibility on the employee, just build it into the system.

‘Til Friday.

from, matt

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