I ticked off 90% of my to-do list by using this self-challenging approach!

One of the things that I hated about one of my previous managers is that he always challenged me, on everything. At first, I looked at this as a downside in his personality and management style. Recently, and as I was going through one of my considered paradigm shifts, I decided to empathize with said manager after seeing him succeed in every step that he took in his life. I decided to look through his eyes, and like any other time that I did a paradigm shift, it was a revelation.

Positive challenge has always been questioned as a motivation, especially to operational staff like myself who almost always find themselves paving the way in front of the rest of the teams to become productive. We have enough on our plates already, you'd think! Recently, I have actually found that having a challenge to my decisions is very healthy, or at least on an executive level.

So this is how it works: You come to a conclusion or make a decision, you have a conversation about why or why not we are making such a decision with your manager. I have found that through constructive conversations with my manager and my teammates we have reached better conclusions and we managed to get a wider view of things, just by offering a challenging question and throwing it out there and getting different answers and different points of view before coming to a consensus.

You would think that all I'm saying now is normal and part of any decision making approach in any team or company. That's true only if you consider a normal conversation where each of the team members showcase their point of view and they have a discussion about it. But the kind of challenge that I am talking about here is when the manager of the group actually challenges any decision/approach even if they do not stand by their challenge, they are challenging it for the sake of challenging it. Think of it as a healthy hypothesis validation that you would do if you are doing a research.

I certainly did not invent it and was not the first one to observe it. There are many leadership articles and courses out there that that educate leaders on how to make decisions and judgments ethically and using a Risk Analysis, which is similar but more structured than the approach I am describing.

I looked at several articles and courses before I started practicing this challenge by myself, and boy oh boy, the results where outstanding!

For the past few weeks, since I started this practice, I think I have ticked off more than 90% of the work I had done this entire year off my tasks list (Also AI helped a lot but I will leave this to another post). Yet, I can account much of this to maintaining a self-challenging mindset, meaning that every time I was about to do something, I would try to think: "What would have my manager challenged me with?" and then decided how to go about this task. My thought process for each task that I am about to begin consists of a set of questions:

• What is the task? clearly defining the goal and challenging the repeated mundane tasks that are clearly useless, or change the way you do things entirely. Clearly defining the line between the goal and how to get it done. This will encourage you to become more and more efficient with your goals and avoid fixating on micro tasks, which makes me more agile in approaching each task and understand that there are alternatives which leads me to the same bigger goal. Thus defining the task at hand even further, and sometimes changing it completely.
• How to get it done? Then, after you have reached the goal and answered this question of "what is the task?" challenge this answer by asking if its the only way of getting it done, or if there is something else that you can do. Look into new ways of doing things. Gone are the days of writing down a to-do list in your notebook, when you have Notion (although I still keep a planner for the fun of it).
• How long will it take? Although I am a big fan of over estimating deadlines, yet I have challenged myself recently, because if you set a loose deadline you are more likely going to relax yourself, sometimes too much. I found that setting a realistic timeline, then challenging it works much better, and I end up having much better time management and eventually work-life balance, because I do not have stuff piling over.
• Get it done! et voilà! Just like that you get the task done and get on to the next line in Notion.

Although I can validate for myself that this approach works, even if I apply it only to myself and not assuming my manager's spirit when I am in team meetings with my own team. Yet, it requires a degree of autonomy and freedom of decision making, or at least some freedom for decisions to be discussed within the team.