The Tooling Labyrinth

Do you even remember what you came here for?

Picture this, you are a new Agile coach or Scrum Master coming into an organization guns blazing. You’re itching to tackle some Agile problems, show some value, meet new people, and make work radically transparent. In a pre-COVID world, you may not have had to touch virtual tools necessary to achieve the goal of transparency. Maybe all you had to do was just put sticky notes on a board like all those happy go lucky teams on every Agile teaming video known to the Agile world. You could be that perfect Scrum Master.

Unfortunately, the world comes crashing down around you as you are given the first log-in to one of the many ALM (Application Lifecycle Management) tools you are going to use to “track your team’s work and progress”. But wait, that does not sound very Agile that sounds… oops! Too late! Now you have to submit a report to your bosses and you’re lost as to where to find the actual hours versus the estimated hours of the tasks attached to the user story. You are trying to find your “Say/Do” metric and end up in a pretty cool colorful graphic that looks like…

Wait…What are you using this tool for again? Are we sure this is Agile?

Sound familiar? Does it feel like you’ve done this song and dance over and over again? Switching from one tool to another, only to find out you need to add another tool so that you can report out risks vs. dependencies or get financial information on your team’s progress?

Trust me. I’ve been there. It can be dizzying.

Tooling and using tools is a necessity in a modern and mostly remote world. Even the harshest critic of tools must admit they are not all bad. Communication tools allow us to connect, collaborate, and problem-solve in real-time as well as share the funniest memes of the week with our coworkers.

Video conferencing, though more draining than in-person meetings, allows us to move the needle forward on the values we are collectively driving towards. Recording those meetings allows us to return to key conversations instead of relying on the best notetakers.

Access Lifecycle Management tools can be an easy-to-update way of seeing the flow of valuable work across an enterprise as well as within a team. There is a system of record and logical configuration that distributes the workload into teams allowing for the workers to work and the thinkers to plug their ideas into a livable space.

However, all these tools can be overwhelming. They can take us away from our day-to-day work, and interrupt our lives outside of work if we let them. It’s so easy to log on and check the latest status report, or reply to the other team members doing the same thing as you: working outside of business hours. 

It can all seem like paperwork, a waste of time, and well… not very Agile. 


Learning why it’s hard to Tool

I am a tool junkie. I love ALM, Communication, and other types of work tools and for the longest time I did not understand why other people just did not get it. I would explain over and over again how reports worked as my co-worker's eyes would glaze over until finally, they would say, “Emily, why don’t you just make the report, okay?” Or, they would ask me to just create a PowerPoint or Excel sheet instead. Oh, the horror!Sometimes, I would send a very detailed message to someone and not understand why they would get upset because I didn't include a summary sentence. Or, I’d just Slacked them my question instead of using email.

To be fair, right now, I am on 4 different Slacks all with nearly the same people  and I'm really not sure which one to use for what…

Let us take a step back to truly understand why tooling can be so hard: Psychology. 

All tools that will ever exist will always kind of suck because of Psychology.

It’s just a life fact, every single person’s mental process is slightly different. There are common threads in terms of the way our brains tend to reason, but imagine the impossible task of someone saying, “Turn how you think, problem-solve, and creativity view yourself into a series of mathematical programs that will then be used to continuously manage, sort, track, and keep a record of your workflow.”

This is exactly what tool companies have been tasked with. So, at nearly every place I coach I hear the same thing: “Oh yeah, this is the tool we have and it does not do what we need it to do, but it’s the best we have.”

All tools kind of suck, so we just learned to work with this one…

Your brain already knows (hopefully) how it likes to organize information. For example, you could favor deductive or inductive reasoning. A fun way to know which reasoning your brain prefers is to remember whether you tended to be better at Algebra or Geometry in middle school. 

Algebra (deductive reasoning), is about taking a top-down approach to deducing logical solutions to the problems you face. You’re more of a step-by-step learner that turns grand ideas into logical, logistical execution. You have an easier time making the strategic tactical.Geometry (inductive reasoning), is the opposite and requires an almost spacial type of reasoning that takes small details and branches them out to into a grand network. You are a more systematic and network-type thinker that makes logistical small impact problems solving them by first expanding to grander abstractions. You have an easier time making the tactical strategic or can see the far-reaching impacts of a single decision.

Geometry (inductive reasoning), is the opposite and requires an almost spacial type of reasoning that takes small details and branches them out to into a grand network. You are a more systematic and network-type thinker that makes logistical small impact problems solving them by first expanding to grander abstractions. You have an easier time making the tactical strategic or can see the far-reaching impacts of a single decision.

Now attempt to apply even that one difference in logical preferences to a tool. Certain tools are really good at allowing you to look from the top level and see the cascade all the way to the bottom. You can make deductive reasoning assertions and see the impact of your work across an organization. One tool that comes to mind is Rally. Rally is very good at allowing users to see various top-down views at nearly every level within the tool. You can see a very clear high-level view across a Portfolio while continuously drilling down into the details until you get to individual tasks. 


Tools can also be very good at allowing you to branch from a single story or task and see the wide-ranging possibilities, impacts, and ties to other work allowing for a system-level view and inductive inferences. You’re provided a view into the grander scheme and given the ability to build upon, or, identify pitfalls in your progress. Another tool that comes to mind from the Agile business world is Jira/Jira Align. Jira/Jira Align can have a very complex configuration, but that configuration allows for stories, features, tasks, and bugs to be identified and linked across multiple different teams and systems depending on the guardrails your teams and organization set in place when setting the Jira structure. Now ask yourself, can systems do both? In my experience, not well. Deductive and inductive reasoning are two very different ways to not only organize data and logic but analyze and display it. I, as a deductive reasoner, really love Rally and have a hard time with Jira/Jira Align. I wish it was otherwise, but it’s not. It just is. I mention this to remind you all that that is just one aspect of the way our brains can organize and interpret information differently.

So, allow me to reiterate and say it louder for the people in the back…

All tools that will ever exist will always kind of suck!

Agile Manifesto

When discussing tooling, all Agilists have the following phrase from the Agile Manifesto in the back of their head:

Individuals and interactions over processes and tools.

In a modern world where your team is not next to you, even pre-COVID, how can you possibly follow this princie?

Well, it’s important to read the fine print of the Agile manifesto here: “We value the items on the right, we just value the items on the left more.” Meaning that if your tools are getting in the way of individuals working, or, blocking proper interaction between teams and stakeholders, then you have a grade “A” for “Agility” blocker.

It is important to see the value that tools provide without becoming overly reliant on them to do the work only people can do: build relationships and think creatively. Tools can not solve every problem or form every conclusion. If they did, we would quickly be out of a job.

Moving Forward: Tooling with Understanding 

  1. Create a symbiotic relationship with your tools.

In the wild, animals create symbiotic relationships in order to survive and thrive in their habitat. I believe something similar happens with tools, which explains the groans in the room every time someone suggests a new tool to fix a current problem with the current tool.

It is necessary to attempt to form symbiotic relationships with these tools to continue to benefit from the value they bring you and your team. Find their strengths, their weaknesses, and consistently evaluate the gaps with a curious but friendly eye. You have to live with this tool so might as well try to become friends with it. 

Think of tools like a co-worker you have trouble liking. You cannot just ignore them or not work with them, you have to find common ground and try to understand how the other thinks in order for you both to gain benefit from each other.

Then, and only then, are you able to start to evaluate supplemental tools to help fill in gaps.

2. Create a Value Proposition for each tool you use & Review that with your team/management.

As stated previously, it is important to understand what value each tool you use provides for your team or organization. If you’re frustrated with a tool, spend some time listing out:

  • What value does this tool provide today?

  • What could this tool provide if used in a different way? What are its possibilities?

  • What are the gaps in this tool?

  • Does it still provide value even with those gaps?

Review with your team and identify if there are any additional concerns or if certain team members are using it in different ways than you might expect. 


3. Create Tooling Working Agreements

After you have become one with your tools and how your team uses them, it is time to decide within yourself and your team how you would like to use tools moving forward. Ask your team to come to a consensus on the following items:

  • What tool will we use to track our day-to-day work?

  • What tool will we use to track day-to-day communications within the team?

  • What about outside of the team?

  • Do our answers change if it is an important question vs. a cute meme we want to share?

  • If we were to define the use of each tool in 1-2 words, what would it be?

Write each answer into a “Tooling Working Agreement” and remind your team members if/when they break that agreement. Communicate these rules to stakeholders so they know how to best get updates and communicate with the team moving forward.

This can work outside of your team too. Whenever I join a department or I start working closely with someone I ask them: “What is your Communication Style?” aka “How do you prefer that I bug you?” You would be surprised what people say, and how much it can improve the dreaded lengths of time you spend waiting for a reply after sending an email or text.

Communication, tracking work, and understanding how to be successful in a remote world surrounded by all the different tools can be overwhelming. Hopefully, I have laid a good foundation for you to not only feel better about your relationship with tools but help improve your relationships and interactions with other people when needing to use tools.

All tools kind of suck.

But you do not.

Happy Tooling!

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