How to start a discussion in a startup in order to start using a more useful workflow tool

Question

My boss, for the entire company's workflow, uses Google Sheets as a sort of feature-tracker/TODO-list. The company employs 7 people, aside from the CEO (my boss), who all work remotely. There are 2 software developers (myself included), 2 linguists, 2 marketing personnel and the CEO's son.

I did once suggest to my boss that we at least move to a tool like Trello that functions similarly, but with much more flexibility. This was when he said that Trello would be a new tool that everyone has to learn, and he doesn't want to do that as everyone is already used to the "Google Sheet flow", and that it would be difficult for everyone to migrate.

The problem is that if things are pushed into the backlog, as in "not important enough for this next release/campaign", they are often forgotten about. We will continue to add things to fix/add at the top of the list, and things that were low priority before become essentially non-existent. It's also hard to tell why we backlogged something because of the limited flexibility of Google Sheets, and having progress tracking is out the window. Here's an example from my Sheet (feature tracker) for a high-priority Android app fix that got mixed in with other work:

This sheet is now about 75 lines long for the next version release of the app, with some duplicated information and no visual organization except "what's on top is most important".

I've been testing out some free workflow/task management tools for the past few hours (on my own time) and I am convinced that it would be beneficial for all the employees of the company to use such tools.

What benefits about employees and management can I use to convince him that it's actually a good idea? I've come up with the following:

1. Transparency - all employees that could/should see what the others are doing, can
   • e.g. the marketing team would know how close developers are to finishing the next release, so they can start making the appropriate materials/announcements
2. Organization - tasks can have custom priorities, making them easier to organize
   • this is better than the 'top-down' approach that we currently use
3. Due dates
   • pretty important - due dates can be assigned and on the calendar instead of hidden in a bunch of comments in a spreadsheet cell
4. Labels and subtasks
   • get even more specific with labeling a task or dividing it into specific subtasks with completion steps
5. Automatic update tracking
   • when an task/subtask's progress is updated, it already has user and timestamps, so much less noise overall (we are currently marking who commented and when)

There are probably more benefits... How can I start a discussion within the company to migrate to a better workflow management tool?

Answer 1

Business case, business case, business case. The best way to frame nearly any change to management is some combination of:

• What we are doing now is costing us money.
• The new way of doing things would save/make money.

In this case, the biggest thing I would highlight is important work getting lost in your current system. If this is happening it is causing some combination of:

• Releases getting delayed.
• A lower quality product being released.
• Your team working at less than optimal efficiency.

All of this has a direct impact on the company's bottom line. That is the case I would try to make.

A few other points:

• Focus on the positive benefit to the extent possible. If your boss is invested in Google Sheets (and perhaps created the current system), "this new tool would be beneficial" is better than "our current system is bad". I know this somewhat contradicts what I said above. If there are current problems they do need to be highlighted. But still, make the case as positive as possible.
• Always aim for incremental change. A completely new way of managing the team's work is a high-risk change. There is a reason management would be reluctant to do that. Try to get permission to use a new tool in a much more limited context instead, for a small project or part of one project. Or you could even use it just for yourself to manage your own tasks, if you are having trouble keep track of them. Once you can show how it works and the benefit, you will have a much easier case to make.

Answer 2

Realistically you have already asked and been turned down. You should take this to heart, pushing it can make you look like the one who has trouble working without tools holding your hand for you however legitimate your concerns may be.

But if you must push the matter, then the best way to do it would be to convince the rest of the team, because one person complaining isn't the same as a whole team of people pushing for more efficient tools.

Advice to put together the pro's and cons and business advantages etc,. are great if you have a boss who likes going through that sort of stuff, but in small businesses and busy bosses that's not always the case. If it was me, I'd just be wondering why you have so much time on your hands to be making presentations, and whether it's work time or your own time you're doing it on. And then I'd start scrutinising your work a lot closer to see if you're worth your pay.

A lot of places give their workers a set of tools, the worker is expected to produce within the limitations of the tools, asking for a different set isn't always a great idea particularly when it means everyone else needs to use the new set. If the new set IS introduced, you can pretty much guarantee other staff will complain out of sheer inertia. So even if they're better tools, it's still a tradeoff for the boss in terms of morale etc,.

Answer 3

Developers often underestimate the difficulties non-technical people will have with new tools. Good developers also embrace tooling changes and workflow changes that make life easier, so they tend to get pretty good at switching. This isn't true for everyone else, because their job doesn't center around that type of information flow. I've been in organizations where this exact tooling change fails, and we wind up emailing spreadsheets in Excel, which is even worse. Truth is, the distraction across the business probably isn't worth it at this point.

I'd focus less on the tool mismatch and more on the workflow. Are things prioritized by any sprint planning? If so, you can use that time to migrate the data to trello or something even more dev specific like pivotal tracker. If not, you can informally start introducing the structure step-by-step. You can then update the spreadsheet at the end of the sprint, or during morning stand-up meetings. That will help you get the tooling internal to dev, with all the benefits of increased visibility, etc. That's not simply a tooling issue.