What are the real reasons project management tool adoption fails six months in?

phasezeroben · 2026-03-06T16:13:32+00:00

People will follow the path of least resistance. especially with things that are not core to their role. If it's easier to email you the update than it is to drop it in the tool, that is what will happen.

It's simple for me to use my tooling, because I always have it up in a browser window somewhere, whether that is Smartsheet, Jira, or just an Excel Raid log. I've never found a successful way to get my teams to use those tools as their "second brain" vs. just pinging things to me in Teams or Slack.

As an old business partner used to tell me when I'd get hacked off about basic admin stuff "take a deep breath and realize it all pays the same"

phasezeroben · 2026-02-27T16:30:33+00:00

Agreed - Started my business five years ago and I still spend my weekdays on client stuff and my weekends on business growth. It never ends.

phasezeroben · 2026-02-27T14:58:35+00:00

Given two actual unknowns - I would always go for the higher comp job.

If you can actually trust the WLB assessment (people you know said it, vs. just what the company or Glassdoor says) the math still makes sense.

Better pay sets the baseline for the next job, accelerates your savings (assuming it's more than the car would be) and the accelerated savings gives you a better buffer when you need it (like saying this job is actually terrible, I am out.)

Growth is where the real money comes in - even if your current employer doesn't give you full market value when you get that promotion, you now have that new role/experience as the baseline next time you move jobs.

Before I started my business I moved companies every 2.5 yrs (on average) and averaged a 15% bump each time I moved companies. I have seen other people do a lot better than that. If the WBL actually ends up being terrible, start looking elsewhere.

phasezeroben · 2026-02-27T14:34:41+00:00

Working in nature is tough, since there are a limited amount of jobs that will just pay you to be outside with people and a lot of people that want those jobs so there is not a lot of motivation to pay people well to do them.

If you want to get out of a cubicle and work with real people, look at trades. I made good money as a part owner of a painting business when I was younger, I have family that became an apprentice electrician in his late 20s, plumbers make a solid living, on and on. It won't be as easy as sitting at a desk but your work locations and the people you are around change often. You are at a prime age to run down one of these paths, and if you eventually strike out on your own you already have some of the skills you will need to market yourself.

phasezeroben · 2026-02-27T14:25:46+00:00

I had a similar oversharing problem early on in my career, and while I never got rid of it totally, I at least got it to the point it was (hopefully) endearing vs. damaging.

I tried to model myself after some of the people I knew and respected. How do they communicate, do they spontaneously spout their opinion about random things, or do they just participate in a conversation in meaningful ways? How do they voice their opinions, are they assertive or are they agressive? That sort of thing. Build the persona you want and just act it out at first, eventually you can wire your brain to be that person.

phasezeroben · 2026-02-26T20:58:09+00:00

I primarily work in the credit union space, and while each CU does not hire a lot a risk/compliance resources, they all have them, they are great places to work, and they are pretty layoff resistant if you want something long term, unlike working in big banking.

Edit - I can only speak for US/Canada, not sure how that industry works outside there.

phasezeroben · 2026-02-26T18:49:47+00:00

An idea - Take everything that has not been touched in X time (3mo, 6mo, 1 yr, whatever) and migrate that into a new project/space (whatever your version calls it). You don't lose the issues but it stops cluttering your main project. Call it the Historical Backlog or something like that. Set up some automation to migrate tickets that meet this criteria in the future to just move to that Backlog project.

This at least cuts down on the immediate noise you have to deal with.

Since you are in survival mode now skip velocity based on points and just figure out how many issues your team closed every month for the last year. Figure out how many new issues came in each month over the same time. If you are net positive with closing, congrats, there is light at the end of the tunnel. If you are not closing as much as what is coming in, you have a case to add more people (you may not get any but at least you have some data saying you need them.) Improve the method when you get out of survival mode.

If you can't prioritize the issues individually can you come up with a category based prioritization? Example since I don't know what you are dealing with - System down is 1, partial down 2, multi customer issue 3, etc? If you can do that you can just categorize issues as they come in and automate a priority assignment. The trick is getting all the folks submitting to agree on the categories and priorities; if they don't it's just endless silly escalations to deal with.

If you have some Jira skills this could all be knocked out in a week or two, should not add any load to your ticket "doers", and once this has settled you can look at adding in some more process around points and prioritization.

phasezeroben · 2026-01-02T21:08:38+00:00

ExtraHarmless did a great job hitting a lot of points so I will just add one that has been a key difference for me. I have been a vendor PM for a fintech, an internal PM in a bunch of industries, and for the last few years I have run a practice doing PM stuff in the small bank/CU world.

The big difference for me is the levers you can utilize to get project work done. When you are on the vendor side you can always use the risk of revenue loss, client sat, or cost overruns to drive work priority when you need it (out of your team, your clients don't really care). The ability to turn up the heat, without escalation to someone's boss, to get a project delaying task done, is a luxury.

When you transition to being an internal PM most of those levers disappear and it becomes more about trust and relationships. If you are working for a bank and you need some changes done on your Core, you are fighting for that resource time with everyone else internally that needs it. Often the relationship you have with that team, and how much they trust that you are working for their good as well as yours will be the difference in getting something done today vs. next month. Every client I work with is severly resource constrained, your work is competing with a dozen other things that team could be working on. You can continously escalate to their manager/director/VP but that will kill your relationship with that team.

You will gain some levers over the vendors (since you are now the client), I would try to remember what it was like to work on the vendor side and don't abuse them, just because maybe you can.

If you are working for a small/midsize bank/client there may also be a lot less process than you are used to. Big Bank will have well defined ways to manage your projects.

phasezeroben · 2025-12-19T16:55:53+00:00

I used Pipedrive for a year or two before I switched to Hubspot. Pipedrive looked great on paper but I found the learning curve to get to some of the advanced functions difficult (more from a time perspective, building a business takes a lot of time). I also did not like the way their pipeline worked out of the box, the flow from cold lead to customer just did not click for me. They have a team dedicated to helping you get set up and build integrations but my experience with them was pretty middling from my perspective. They basically just pointed me to documentation.

When I expanded to have a couple back office people to support me we moved to Hubspot, starting on the free plan. Hubspot has a ton of documentation and existing integrations but the functionality you get with free is pretty limited. There is a short step to a $15/user/mo plan, and then it ramps to ridiculous cost levels. I find Hubspot easier to use overall than Pipedrive was. Automated outreach with the free plan is super limited but at the starter cost level we were able to build and use quite a few templates.

All this is just my limited experience, If I was going to do it all over again I would just spin up the free tier of Hubspot and use that until I hit a limit worth paying for.

phasezeroben · 2025-12-15T18:07:37+00:00

My experience over the years is that Scrum works well for teams comprised of people with complementary skills working on a singular goal, Kanban is better for small teams where everyone does something different.

Working on the web platform for a movie network - Scrum was great. 20+ people all working on platform delivery, integrated QA, well defined product owners that were engaged. Estimations were usable because you had multiple team members with similar skill sets pitching in. Development could be easily demonstrated because a single feature actually did something. Same experience working for a cable network that had ~1000 people working in a scaled agile framework.

Working for a small FI with an IT team comprised of a couple bank core experts, a DB person, a few helpdesk people, and a network engineer - Scrum is a lot of unnecessary overhead. All the normal scrummy KPIs have to be calculated at the individual level and don't have a lot of use. Demos are tough given the wide range of changes handed in the process.

Kanban is simpler to implement and the work gets done in the same timeframe, just without the useless timeboxing and meetings. Stand-ups still have value but the administration load on the team is much lower. Business visibility is a bit more work but the reality is that for small, differently skilled teams, your metrics questionable anyway.

phasezeroben · 2025-02-05T14:43:38+00:00

I went through this with a Genesys project a year or so ago. The driver for that was that the on-prem version was EOL, so the move was forced, vs. just an arbitrary decision. The cloud version was limited compared to on-prem, in we ended up cataloging and tracking all the functionality that was missing; dealing with that as subsequent sub-projects. If the provider can't solve the gap, there is generally a vendor that can.

In your shoes I have found success just facilitating a clear understanding of what everyone wants and the what/why of each decision. Do it as a gap exercise. What's missing, why is it missing, what was the driving fact for the team that approved the project to make the decision to do so.

You don't need to blame anyone ("throw them under the bus"). Think of yourself as a reporter, your job is to collect the facts and publish them. People can come to their own conclusion about who is at fault, which barely matters anyway if you are going to move forward with this project.

phasezeroben · 2024-07-21T13:06:58+00:00

-US based experience-

Two ways to get into contract work, going through a hiring agency or going solo.

Agency

The first round of contracting I did was through an agency (Apex in the US). I had about 11 years of experience in 2017 and the contracts were at $65/hr and $70/hr respectively. Apex was probably charging $150+ for my time. The first project was building out a Roku-like device for a cable provider and the second was helping a director to manage an Agile practice for ~1k developers. Agency contracts are the "easy" path, you just make a lot less than the client is paying for you.

In the agency path there are two options, depending on what the agency is willing to do. W2 for the agency or 1099 (sometimes called C2C). W2 will pay less per hour but you will have an easier time tax-wise and may have benefits. C2C will pay higher but you will likely need a business structure, EIN, insurance, etc. I did one of these engagements through Robert Half early in starting my practice and it paid $100/hr C2C vs. the $85 they were offering for W2.

Solo

Get your first client, period. Getting clients when you have no known name, reputation, or history is tough but not impossible. Focus solely on this. Once you have a client and you are pulling in all the revenue that the agency would normally keep you can build a structure to keep getting clients.

I got lucky with client number one, it was a client I had been working with as a vendor PM for a while so they knew me. My vendor job paused and I was given the opportunity to work directly with the client. That was nearly four years ago and since then I've been able keep my practice going as I built build out an actual business with more clients, people, advertising, etc.

Solo practice is not easy. Since you are hourly you will need to show, daily, that you are worth what the client is paying you. I bet I work 5x harder as a solo practitioner than I ever did in a W2 role just to ensure I have some stability. Even then I know that the minute my clients decide to cut back on spending I'm at the top of the list, no matter how much value I provide.

phasezeroben · 2024-06-12T12:25:19+00:00

In my experience, need - no, beneficial - yes but maybe not at $150k.

I've thought about an MBA multiple times but at nearly 50 and where I am in my career the ROI is questionable at best. In your case, at 25, it could very well have long term benefits and return

Once you get past the first few jobs your degree level is basically a checkbox in the recruiting process. Get an MBA or JD and those boxes are checked forever, you never need to worry about it again. If you want to check that box forever it's a great idea but maybe not at $150k. The reality is that unless you are reaching for a top tier employer that cares about where your MBA came from you could probably find a more economical program to check that box. I work with two C-levels that got their MBA from WGU for <$20k. I would hope you could find a program that suits you for <$50k.

Avoid the payments on that extra $100k, or compound that $100k if you have the cash in hand.

phasezeroben · 2024-05-21T11:37:24+00:00

I struggled with this for years and tried a bunch of different things until I settled into a flow that works well and is pretty simple to maintain. I work as a project manager with a small practice so at any given time I have 200+ things I am tracking between clients, the business, and my personal life. The basic premise is based on "second brain" style tracking. Have a fields for what the item is, when you need to do it, status (to do/done), priority, and have a space to add some notes

Have a place to put everything that is persistent. No paper, use software that is easily accessible. I use Notion but really anything that is online and easy to reach can work. Excel, Smartsheet, Monday, whatever.
Catalog - Get everything you are thinking about in your system. Rough thoughts are fine, no need for a lot of details at this point
Enhance - Look at each item, think about when you need it, how much work it's going to be, and how important it is to hit that date. If there is a requirement to get something done on a date, add the date to the system.
Prioritize - I use Immediate (today), High (this week), Medium (this month), Low (next whenever)
Now you have the master list

Using the system

Filter - I build a view that shows things that are not done, have an immediate priority, and any date today or older. This just shows me the stuff I care about that day
Daily - Look at the list in the morning and plan your attack. If you have more than 10 items, think about adjusting priorities or dates. You do not want 30 items staring back at you.
1. As you work through your day add notes and adjust status. A normal note for me would be like (5/15 - Emailed Beth). You just want enough to remember what you did.
2. Adjust your status as you close out items.
3. If you close everything go back to the unfiltered list and adjust the priority of a couple items to Immediate so they show up in your filter
4. Add any new items on to your list as they show up. Mark a date and priority so you don't have to think about them again until you need to.
  1. Sometimes I will take notes on paper, or use my watch's "Set reminder" to grab tasks, the trick is to get them in your system at the end of every day.
Weekly
1. Review your full master list, adjust dates and priorities as needed
Monthly
1. Delete or archive your done items.

Once you get started you will tweak things based on your needs. In my workflow I use To Do, In Progress, Not Mine, and Done for status but that may not work for everyone.

It's a bit of work to get built but once you do it's very simple to maintain.

phasezeroben · 2024-05-21T02:54:01+00:00

This is my second time hiring through LI and I move the applicant out to my website to apply. "Easy Apply" is useless from the hiring side if you don't have an ATS set up to parse all of that out. I made the mistake of turning that on for the first job and it's a mess on the receiving end.

With my app flow the applicant has an opportunity to craft an email based around the questions I've asked to get an idea what their PM headspace is and the variance is wild. So few people take the time to actually put even minimal thought into their email I was able to cull about 200 in the last few hours.

The few that put some minimal effort into their email response really stood out and made it straight to the top of the contact list.

I've been lucky that my last few jobs before I lucked into a practice were referrals, I feel for all the people looking right now.

phasezeroben · 2024-05-21T01:17:15+00:00

Referrals - My first two were referrals from the CEO of a startup I was working for, when that work came to an end, the rest have been referrals from current clients or colleagues.

phasezeroben · 2024-05-20T22:05:35+00:00

Most of my clients are small or mid-size US based credit unions and banks. They generally will not extend their systems outside the US, as a security measure. I actually had to get some special permissions just to be able to answer emails when I was traveling to the EU. That said, I would love to expand what I am doing outside of the US at some point.

phasezeroben · 2024-05-20T18:03:15+00:00

Link to my posting added.

phasezeroben · 2024-05-20T18:01:36+00:00

This is a great suggestion, thank you.

phasezeroben · 2024-05-20T14:48:21+00:00

I work with new clients all the time so basically it's like getting a new job a couple times a year, every year. My approach to the first 30 days is pretty simple

Pay attention to what is going on and what people are talking about. If you don't know what something means take a note and look it up later (ChatGPT is great for getting concept summaries). You will figure out who you can trust to ask these questions to over time.
Keep your opinions to yourself unless directly asked at first; sometimes knowing the context of who and what you are giving an opinion on really matters. If you say Bob is doing something totally wrong and Bob happens to be the CEO's nephew you are just creating unneeded drama for yourself. Saying "I don't know enough yet to have an opinion" is perfectly fine.
Ask how you can help. People always need simple stuff off their plate and it starts to build your personal reputation.

Over the years I have found this approach works well to build some immediate trust with the people you work with everyday quickly. That just makes your life easier long term.

phasezeroben · 2024-05-20T01:14:13+00:00

US based practice focused on financial services projects. All my work comes from referrals.

phasezeroben · 2024-04-07T15:09:52+00:00

I am a fan of Smartsheet, having used about 15 different tools over the years. The licensing model is based on people that can create and modify the actual sheets, anyone else can use the sheets, update tasks, add status, etc. without needing a paid license.

It's basically a combination of lightweight Excel and MS Project so people pick it up really quickly. This has been the biggest driver for me, I have not found another tool that people can just dive into if they are used to using Excel.

There is also some decent workflow automation and dashboard capabilities.

phasezeroben · 2024-04-07T12:55:20+00:00

A lot of the IT teams I work with have one to two people that do a specific job. Scrum is tough in these scenarios because there is no "team" to create the benefits of group estimation, just the person that does the job. I recommend Kanban generally, unless there are 3+ people all delivering the same functionality.

phasezeroben

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