You already know the answer. There is no best tool.
The best tool is the one that works best for you. That doesn’t mean your organization is a special snowflake, it just means your organization has its own specific context and that’s ok.
So how do you go about choosing a tool? The good news is that it’s actually not that complicated.
You need to start out by doing some homework. Investigate some options that seem as if they may work for your context. Focus on your current needs. Planning for those long-term future needs is often wasteful because by the time you get there everything beneath you has changed.
Here’s an example of how you can address your situation:
Maybe you’re currently using Jira and you realize that Jira out of the box doesn’t quite give you what you need. Investigate some Jira plugins. Maybe there’s something out there that addresses your needs. Also, look at tools that integrate with Jira. In other words, look at tools that still allow you to use Jira while providing other functionality. Yes, it can be cumbersome to switch between 2 tools, but if both tools provide lots of value, users are unlikely to complain.
On the flip side, maybe the organization is willing to avoid the sunken cost fallacy and consider non-Jira solutions. The same rules apply. Do some investigation and consider which options are viable.
Once you have some real options in front of you (ideally 2-3), perform an MVP on all options. What???
That’s right, practice what you preach. You ask your teams to address uncertainty and de-risk, now it's time for your to do the same.
But how do you do that? Again, it sounds complicated but it really isn’t.
Contact the sales person for each product and obtain a free trial licence. You might even be able to obtain a limited time full licence without talking to anyone.
Anyways, use your trial products the same way you would use your current tool and do so for a predetermined amount of time that gives you enough time to assess each product.
As you progress you’ll be able to eliminate some products. Hopefully, by the end of your trial period you have 1 or 2 options that are still viable. If you have more than one, you have a decision to make.
This concept is crazy. Why wouldn’t I just pick the right product from the beginning and not waste all the time on the other products? If I just do some more upfront analysis, i can surely arrive at the decision I need. Does this sound familiar? BUFD (Big Up Front Design). We all know how well that works. This is what happens when leaders don’t practice what they preach. They fall back into their old ways of doing things even though they demand that their teams operate in the “new” way.
So, if you want to improve your Agile tooling, treat the effort/initiative as any other type of work.