Asana as a Reflection and Personal Growth Tooling

7 min readApr 6, 2021

One of the topics I often hear from friends and colleagues a like is that they always struggle with 1:1’s with their leader or direct reports. Usually, it ends in some kind of casual conversation which leaves both parties craving for more and feeling like the meeting was not really focused. In a climate where our time is precious and the “meeting” culture of home office has increasing pressure on our schedules, we need to really focus on value proposition when it comes to these regular sync meetings.

I decided to experiment, by focusing the meeting on a semi-structured approach that builds into it some fluidity and enables a way of reflection from either party. I wanted an approach that reinforced achievements, learning and enabled the challenges to be framed as opportunities which get empowered.

This is something which became even more possible with the organisations switch from JIRA to Asana. Asana is a much more “ playful” experience which feels less corporate and more enjoyable. I wanted to structure the approach in a Kanban like way, which had this pull mechanic and expanded on the first entry to fill out a perspective which then can be used to drive a discussion to an outcome.

Below is the approach I took with utilising Asana as a powerful reflection tool and how I go about on boarding the individual to the method.

Designing the Approach

The first thing I did was grab my Remarkable and I initially drew the five stages of a retrospective:

Set the Stage
Data Gathering
Generating Insights
Decide on the Outcomes
Close the Stage

With this as a base, I then thought about all the 1:1’s I had in my recent time, thinking about the sessions I had that I really felt empowered and fruitful with and then I realised that they pretty much follow a similar line of thought as the stages of a retrospective.

Casual “How are you?” Introduction
Usually the asking if there are any topics to discuss
Mutually agreeing which topics to focus on first and discuss more on the topic
What are the challenges?
What are the opportunities?
Picking actionable items to move forward with
Casual Ending with some light questions and discussions outside of the topic

With the parallels identified, I worked on building a Kanban board in Asana to mimic a “typical” retrospective.

The next stage was to make it more playful / friendly, to make it not such a rigid process. As I wanted to focus on achievements and success in the first part (as this is usually always forgotten by people) I wanted the first 1–2 sections to be focused on the wins, the learnings and the real achievements big and small, this would always be seen at the start of the meeting.

The really nice thing about Asana is that you can create a customised form for each of the projects which can always be used as an entry point, with this in mind I created a simple form which would be a catalyst for the meeting and enable people to spend time before the meeting to reflect on the past time period (week, two weeks, month etc) the form is designed in the following way:

How happy are you right now?
The person can pick between 1–10 (1 being bad, 10 being great)
Why did you give it this rating?
What is one thing you achieved this week?
What is one thing you learnt this week?
What is one thing you would change if you could?

This, I decided should be the first entry into the meeting and something that can be taken apart and split into the various sections of the Kanban board.

The next thing I wanted to craft is the “Why”, as Asana recently released the “Project Brief” I decided to utilise this to enable the person to draft their why and identify areas which they want to grow in, their blind spots and what their expectation for my role are.

Why are you at Insert Company Name and what do you want to achieve?
What are the areas you want to grow in and interest you?
What are your blond spots, the areas you know you need to improve on?
What are your expectations towards me and my role?

The main reason for this is to really enable the person to think deeply about their mission and what they want to achieve, this serves to enable us to discuss openly the various points and enables me to build time & space to work with the person on these topics. This is something which we would check in with over a number of months and see how we are doing on the various points and topics.

And that’s basically it for version 1 of this approach and something that I would adapt individually to the people I would run this with.

Setting the Frame and Getting Started

The first thing I always do before setting up such an approach is sit with the individual and talk about the idea of utilising a more structured approach to help them get more value from the regular sync. This approach enables the other party to address any concerns they have with the system and usually sets a solid groundwork to testing out the method.

Once we agree to try out the approach, I go ahead and create a private project in Asana utilising the template already created. For the first session, I just send the link of the form and ask the person if they can fill it in 1–2 days before our next sync, this way I can onboard them to their board in realtime and they can see and understand the process. I then also add the link to the form to the regularly occurring schedule so that they can always find it.

Before the meeting, I read through the form results and pre fill in some of the columns based on the information the person wrote. During the meeting I set the stage by commenting on the happiness rating and leave room for a short discussion. I then clearly highlight their achievements the person has had in the last time period and really emphasis the important of regular reflection, to not forget the path forward we have built. From there on we work right to left one the board starting with the action items, goals, roadblocks and finally getting to the open section of topics to discuss.

I never expect that every time there are concrete topics to discuss, if there is nothing we usually talk about the various projects at work and any learning material consumed in the last time period.

That’s it!

Reflection

One of the biggest benefits of utilising Asana for this approach, is the ability to regularly look back using the timeline view to gain better perspective on how the happiness has developed overtime and to have reflection sessions with your colleagues.

Note: You must remember to set dates on all of the aspects discussed for them to appear. My general rule is to set dates for all the items based on the date we discussed them, there will always be exceptions but it’s generally a good approach to follow.

These sessions on a frequent basis enables us not to forget how we got to where we are and want successes we have actually received.

Reduce Rigidity

Everybody is different and it’s something you should remember. You will have people that will love filling in the form each time and enjoy the process aspect of this approach and you will have others that really rather not each time fill in the form or walk the board, that is ok. The key is to remember to trailer the meeting structure based on the individual.

I usually try to on a regular basis take a break from the approach and do something more abstract, like a walk and talk. Meet at a mutual location like a park and just walk with the person for 30–60 minutes to get a change of scenery and meeting approach. Even breaking the “rules” is ok and just have an open session to discuss anything.

Conclusion

I hope this article inspires you to think of new ways to approach these regular sync sessions with your directs or to challenge your leader to change up the approach. Individuals, teams and organisations are different and you should try to approach a style which fits to the time and place. Don’t get stuck in a rut and always ask if these meetings generate value, if not challenge it and work together to build an approach that works.