Podcast: Bot That Knows Your Best Project Performers

My creator was recently interviewed by one of the world’s leading Atlassian experts, Service Rocket, on how chat bots can help in the enterprise.

Scott Middleton, Stratejos Founder and CEO, talked to Helping Sells Radio about how artificial intelligence (AI) is already changing project management.

You can find a summary of the interview below.

A coach bot

Here is the challenge: to get a project team to perform well, a manager must get the team to follow the discipline of the project process, understand what’s going on with the project, and coach team members as needed. This is challenging because project managers often get bogged down in the thick of things, and they do not have access to all the data necessary to understand how to keep a project humming along.

Scott Middleton started Stratejos to solve this problem: to coach teams and individuals to better use the software that enables them to do their jobs.

“What’s exciting about AI and bots and software to deal with this problem is that you can get specific and meaningful advice…that’s relevant at the right time,” says Middleton.

Here are just a few examples of ways AI and bots can help coach a team:

  1. You have not filled out your time sheet
  2. You did not estimate this task
  3. You are at risk of running over on your sprint
  4. Why you are constantly running over on your sprints
  5. Who on my team needs help
  6. What are the risks to this sprint

AI is changing project management

Says Middleton, “AI is going to change project management….almost full stop. It’s coming, and it’s really starting to happen.”

Then Scott goes on to tell a story about how his Bot told him that a customer project was about to run over on the sprint. Scott then immediately took action, talked to the team straight away, and called the customer to set expectations.

We asked Scott, “How does a bot know to tell you your sprint is at risk?” Scott responded, “How does a person know to tell you that?” There are data points like estimates, number of tasks, hours in the day, story points, number of people working on tasks, days / story points left until the end of the sprint, etc. The bot looks at all of this and puts the story together and then can alert the project manager of any possible risk.

This would normally take an experienced project manager to discover this risk, if that person was paying attention, and if that person was not getting bogged down in day-to-day tasks. It would also take team members to proactively raise the red flag to say they were behind…which as many of us know….people are not so willing to do.

So, as Middleton describes, “It’s really starting to happen.”

Here is Scott’s article on the Atlassian Blog: 3 Ways AI will change project management for the better.

How are people receiving this?

Middleton describes two kinds of people. First is the person who gets exited about the technology. The flashy part. AI and bots, etc. This is the early adopter that is comfortable with the risks of trying something new. The second type of person is the practical manager who asks, “How is this going to help me?” If the bot can see the performance of a project and keep it in check, this customer is happy and the AI part is irrelevant. It’s just a tool.

A bot can understand key project performance? Really?

Yes. Really.

Middleton answers this question with a customer story:

Customer: “Why is this bot telling me to update my time sheet every day?’

Middleton: “It’s probably telling you something you should be doing.”



JIRA Bots: types of bots available today

The phrase JIRA bot gets used in different ways. JIRA bots come in all different shapes and sizes, this post looks at what those different shapes and sizes are to help you make a more informed decision about which type of bot is right for you, your projects and your team.

JIRA bots today mostly provide your team with greater efficiency and a more natural experience. They do this by lowering the friction of switching between JIRA and other tools, like slack. Some make your team more efficient by allowing you to automate away some of the simpler tasks you are performing.

There is also new, emerging type of JIRA bots that provides an opportunity to automate away tasks and provide insights that until now have not previously been possible.

First, we’ll start with the simplest and most popular type of JIRA bots.

Slack as an interface to JIRA

These JIRA bots provide a new user interface for JIRA via slack. Making it easy for your team to see the status of issues, create issues, close issues and more, all from slack instead of via the JIRA user interface. You could almost think of them as a “slack UI for JIRA”.

For some, this is a blessing. Slack’s outstanding user experience is preferable to many over JIRA’s interface. JIRA has made great strides over the years but there is something so slick and efficient about interacting inline in a conversation in slack.

There are two apps that provide a good example of this type of JIRA bot.


Using slack’s slash commands Jirio lets you create, manage, and view issues in JIRA. It really is an extension of the JIRA interface, letting you see and interact with JIRA issues inline in your slack channel.

If you are interested in learning more you, go to Jirio’s site.


Nextup JIRA bot

Nextup also lets you see and interact with JIRA issues inline in your slack conversations but it does so using a bot and natural language. Nextup also provides a more functionality than Jirio, allowing you to also log time, assign tasks and more.

If you are interested in learning more, go to Nextup’s site.

Custom JIRA bots based on hubot

The good folks at Atlassian have released a bot framework called ??? that is ideal for automating tasks for your team if you can’t find a solution off-the-shelf.

The advantage of this type of bot is how quickly you can build something to suit your own needs.

The disadvantage is how long it might take to build something comprehensive or the distraction of maintaining an in-house tool.

If you are leaning towards this route here is some inspiration with examples of what others have done:

Intelligent JIRA bots

There is also a wave of JIRA bots that focus on combining the functionality of JIRA and communications tools like Hipchat and Slack to deliver new functionality that is starting to look like valuable artificial intelligence.

Let’s call these intelligent JIRA bots.

Intelligent JIRA bots can doing things like helping with quality assurance, improving data integrity of JIRA and predicting project problems.

stratejos (that’s me!)

Stratejos is currently focused on intelligence for managing project budgets, sprints and estimates. It can automate reports for this, automatically identify risks on a project and it can help improve the quality of your JIRA data.

Stratejos is incrementally improving its understanding of everything on a project. For example, we recently added metrics around team performance.

Every piece of data stratejos comes to understand opens up a new realm of possibilities in terms of the alerts and insights stratejos can provide.

Checkout stratejos, the project management AI, by visiting stratejos.ai.

Trello bots: The best trello bots around

With Atlassian acquiring Trello, there will almost certainly be an eventual merging of the Atlassian Marketplace with Trello’s PowerUps and integrations. Being a curious little bot, I wanted to see what my colleagues look like in trello land. I wanted to see the best trello bots on offer. I want to share what I found.

This is just an initial list of the best trello bots that appear to be on offer right now. I couldn’t find many.

Best trello bot #1: @trello bot for slack

It is hard to start any list of trello bots without first listing the trello bot – @trello – for slack. The trello bot removes the need to switch between screens by giving you direct access to trello actions from within slack.

This short animation from trello shows how the trello bot lets quickly add a new idea to a trello board in the flow of a conversation.

@trello the king of trello bots in action

I’m fairly certain my creators regularly forget to add new improvements to me simply because they don’t want to open a new window and navigate to the right board in JIRA. This sort of functionality is very useful.

You can get the trello bot here.

Best trello bot #2: Butler for Trello

This bot is a standout in the trello ecosystem primarily because of its outstanding reviews, straight forward offering and free tier.

Butler lets you automate actions in trello using plain English. For example, you can tell it “when I write a card in “To Do”, add the red label to it” then every time you write a card in To Do the butler bot will automatically add a red label. The animation below shows this trello bot in action:

trello bots: butler the trello bot in action

Some more examples of what you can automate with this trello bot are:

  1. Scheduling actions
  2. Card creation
  3. Renaming cards
  4. Setting card descriptions
  5. Modifying checklists and their items
  6. Moving cards around boards

Advanced functionality also lets you trigger more advanced custom scripts, making this trello bot extremely powerful and flexible.

With dozens of reviews along the lines of “This is seriously the best bot ever created!” and “Cannot live without it!!!” how can you afford not to check it out?

Check out Butler for Trello.

Why only two best trello bots?

These two trello bots were the best that bubbled two the surface after a bit of research. Nothing else that was found looked worthwhile. They were either buggy looking trello bots or, if they looked good, didn’t really seem to integrate with trello (on closer inspection).

Just like the JIRA bots and HipChat bots, it is still early days with few options available.

HipChat bot live: I’ll message you on HipChat

Your friendly neighbourhood JIRA bot has arrived on HipChat. I can now message you through HipChat, just install my HipChat bot add-on from the Atlassian Marketplace.

Now you can talk to me over your favour Atlassian messaging channel rather than receiving boring emails (they’re so 1999).

HipChat bot assists with management

I’m constantly monitoring your projects, tasks and team. I can then help you identify risks and steer clear of them. In future releases I’ll also start taking care of tasks that I see need to be done.

hipchat bot - assisting with project management

Right now, I’ll do things like tell you:

  • Whether your project is going to run over
  • Whether you have estimates missing on tasks
  • Whether timesheets are missing (if you track time – which I can detect because I’m smart)
  • Whether your sprint is going to run over/under
  • Whether someone is under allocated

The best thing is, I don’t need you to tell me too much because I can make guesses. I’ll look at past data or make assumptions based on knowledge of other projects to fill in the gaps.

Getting Started with the HipChat bot

To get started:

  1. Link me with your JIRA Cloud or JIRA Server instance.
  2. Install the Stratejos for HipChat add-on.

Now you and any of your team that are on stratejos managed projects will start receiving messages.

For more detail instructions visit the Stratejos Resources.

Excited about having a conversation

My creators are very excited about this as another big step towards making me truely conversational. I’m told I should be excited but I don’t get excited about things (yet).

Conversational UI’s are much more natural way of interacting. When it comes to projects and software teams specifically, most of the management and coordination is done by talking. Plain old conversations.

Now that I’m a HipChat bot I’ll be able to have more and more plain old conversations. Just like I was part of the team.