A productivity system for autonomous adults

Startup productivity system

I once lost about a day and a half exploring a new productivity system to help me be more productive. That lost time is one of my favourite life experience ironies. Part of the reason I wound up spending so much time obsessing about a new productivity system is that I am more than a little OCD about that sort of thing.

I don’t remember emerging from that “process” with a coherent system but it remains a personal reminder not to let myself become distracted by the search for something new for the sake of finding something new. Instead, I focus on simplifying my processes and my toolkit with a preference for the stuff that I know works for me. When it comes to tasks, I prefer OmniFocus because I have it on all my devices and because I paid far too much money to just ditch it.

The catch, though, is that it doesn’t tie into anything I could use to collaborate with my team at work. Over time my work tasks have split from my personal tasks because different managers have wanted us to manage projects using different tools which became additional layers on top of my OmniFocus system and another layer of complexity to manage.

When I diverted off the productivity cliff

In my quest for something I could use to tie in with my colleagues, I stopped using OmniFocus as my “everything” productivity app and OmniFocus became my poorly maintained personal task manager and a procession of other tools became my work options. In retrospect, that was probably when things started falling apart.

I used OmniFocus exclusively before I started my current job because I worked for myself and I could focus on being productive, not finding ways to adapt to whichever project management system my managers wanted at that point in time. I’ve tried a few services:

  • Asana, which I really dislike for reasons I can’t quite identify (and some I can);
  • Spreadsheets, which are terrible for managing ongoing tasks and, when I think about using them for this purpose, can make me physically ill;
  • Basecamp, which is a terrific project management service and the only reason it became problematic is because there was no meaningful integration for me with OmniFocus so it required a work/other split to minimise duplication;
  • Pen and paper, which isn’t dynamic and too easy to forget about and ignore because my brain knows it isn’t reliable for me; and
  • Trello, which is my current choice at work and works fairly well except, as I write this, I just think it is another layer of distraction I should ditch and return to OmniFocus.

As I see it, the thing about productivity systems and work projects involving teams is that you really have two choices if you want to remain productive[1]:

Option 1 – the team system

Use a system that everyone uses and that works well, generally, for everyone. When I had a small team back in the day, I was looking at Basecamp or Podio (I think). I gave my candidate attorney the two options to look at and she picked Basecamp because it made sense to her. We went with that and it worked well for us. I only stopped using it when my team moved on and maintaining it for one person didn’t make sense.

The key thing with a team-based system is that the directive to use it must come from management even though the choice of what to use should only be made with the team’s input (after all, they need to use it and stick to it and no-one will stick with a system that doesn’t work for them).

Option 2 – The “autonomous adults” system

I was chatting to Don Packett a while ago and I asked him what Missing Link uses to keep projects going effectively. I was expecting him to give me the name of some slightly fringe productivity app (if you know Missing Link, you’ll understand why I wasn’t expecting them to be using Ye Olde Corporate Standard Fare). He surprised me with a really smart and appropriate answer (I wasn’t surprised that it was smart, just because it wasn’t what I was expecting). He told me that they –

aggressively push for ‘autonomous adults’ who can set their own timelines and deadlines and get their shit done in the right fashion.

I love that. As soon as I read that, I realised that a system imposed on a team can, more often than not, reflect an attitude by management that the team does not comprise “autonomous adults” who can be trusted to get their stuff done “in the right fashion”. Instead, people are treated as if they lack the capacity to do what they need to do and be productive.

Update (2016-03-09): Don messaged me and clarified that Missing Link uses dapulse to co-ordinate their autonomous adults, which makes a lot of sense.

This attitude comes through in how they are told which steps to take to complete tasks and when to do them. A better approach is giving them a set of priorities (or, even better, involved in the decision-making process about the upcoming priorities) and left to figure out how to meet them effectively and on time. That doesn’t mean people don’t make mistakes or miss deadlines. Being an “autonomous adult” means being able to make those mistakes, taking responsibility for them and then fixing them without being told that making mistakes somehow deprives you of your right to be a grown-up at work.

My point is …

What prompted to start this little verbal foray into productivity systems was a post by Shawn Blanc titled “A System That Works (for You)” which begins with this truism:

Everyone wants a time management system that works. One they can stick with. One that’s not a pain in the butt.

He goes on to explain what such a system looks like:

  1. It empowers you to do the things you want and need to do.
  2. It aligns with your personality.

What I have learned is that a system that doesn’t have these two qualities very much becomes an obstruction to just getting stuff done. I am also constantly reminded that the key thing is to find a system that just make sense to you and works for you. A system that requires constant tweaking and reconfiguration is, literally, counterproductive. I have reached a point where I can feel just how wrong the system is when I started using it.

A good productivity system should have something that makes it easier to use, enjoyable even. As Blanc noted:

The reason I use a pen and paper is because I enjoy it. The analog aspect adds a bit of joy, which, in and of itself, is enough grease for the skids to keep me on track with using my system.

I definitely find that a productivity system that isn’t aesthetically pleasing to me is problematic because appealing design is a great introduction to a system for me. It is “grease for the skids” to help ease the transition to a new thing and how I can use it.

Most of all, a good productivity system should support you and, as Blanc puts it, empower you “to do the things you want and need to do”. Adding more friction to your workflows is an effective way to dissuade you from using a system and becoming less productive overall[2].

Postscript: I have written a follow-up about a related issue so consider reading “Cross-platform or best platform?” too.

Cross-platform or best platform?

Image credit: Pexels

  1. Being “productive”, to me, means getting stuff done and not spending more than the absolutely minimum time required to maintain your system. If you spend too much time just keeping your system afloat, so much so that it cuts into the time you need to actually get your stuff done, change your system. It isn’t working.  ↩
  2. Of course, now that I am thinking about it more, I am tempted to move all my tasks back to OmniFocus. The challenge with these sorts of moves is that each time you reconfigure your productivity workflow, you take more time away from the time you have to get stuff done so it has to count.  ↩
Enthusiast, writer, strategist and photographer. Inbound Marketing Specialist. Passionate about my wife, Gina and #proudDad. Allergic to stupid


  1. From a continuity management and collaboration perspective, when working on a team, everyone should use the same tool to keep track of who is working on what and the description of the “what”. How each person works on and achieves their tasks is something different.

    The main thing, especially within a growing team, is to ensure that on-boarding new team members is easy and that there is an audit trail of instructions and comments to avoid finger pointing down the line.

    1. I agree completely. At the same time, it seems to me that if there isn’t a system the whole team uses, each person needs to adopt an effective system and sync regularly with the rest of the team in some way.

  2. The thought of a team not having a system quite literally scares me. 🙂

    In that case, Adult Autonomy seems like the way to go but it would add a lot of extra “over head” in terms of regular syncing.

    1. The first step has to be a clear drive from the top. If that doesn’t exist, it will be almost impossible to implement a complete solution.

  3. Leadership’s role in an organisation’s productivity is crucial. If leadership isn’t onboard and/or doesn’t give direction then I would be quite concerned.

What do you think?

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