Summary

Busy people want to be collaborative. But synchronous collaboration with busy people is a trap.

• Calendar matching is costly, and therefore, busy people should work independently.

• Adopting a "ship-show-ask" mindset can be helpful to speed up iterations and to make decisions.

• Doing less but doing things well is always a good trade-off.

• Avoid being a bottleneck in collaborative projects.

• Embrace the law of diminishing returns, and know when to stop adding people and to stop seeking opinions.

The path to hell is paved with good intentions. We all want to be collaborative. We also imagine that some, if not all, collaboration must be synchronous. When busy people with good intentions want to collaborate synchronously, it often means that they get nothing done. 

Let’s get a few first principles out of the way.

1. Shapeless days are not a badge of honour. Busyness and productivity aren’t the same thing. Your days must follow a predictable rhythm if you wish to be productive. I recommend blocking out a predictable block of hours, every day, for deep, immersive work.

2. Even executives must prioritise deep work. Regardless of how senior you are in the organisation, you can’t hop from meeting to meeting and imagine that you’ll make sound decisions. You must prioritise “think time”, written communication and your spells of creative work.

But for argument’s sake, let’s assume you’ve attempted to follow these principles and you couldn’t stick to them. Life and work have taken over and your calendar still looks like a dog’s breakfast. What then? Well, in that case, you must collaborate differently.

Calendar matching is a costly business

Look at the above screenshot. The details are unimportant. There are two colours representing two people’s calendars. If these two people wish to collaborate synchronously with each other, there’s barely any time to do so! Yeah, you might find one slot here and one slot there, but you’ll rarely get any productive work done in any of these stolen slots. I’ll tell you what usually happens in such synchronous work sessions.

1. Since you’ve stolen a slot between meetings, part of your attention goes to recovering from the previous meeting. Part of it also goes to thinking about the next meeting you have to rush to.

2. Since you’ve had no time to prepare for this coworking session, you don’t achieve any depth. The discussion skims the shallows, before you know it the time has passed you by.

3. If you’re lucky, you discuss some actions you must take, but since your calendar doesn’t allow you any room to address these tasks, the only time you address them again is in the next synchronous slot. 

Sounds familiar? This is the cost of coordinating busy calendars.

Instead, work independently

A free calendar opens up pairing opportunities. A busy calendar though, is kryptonite for any synchronous collaboration. If you can’t fix your calendar, I’m sorry - synchrony is not for you. You’re better off agreeing between yourself and your coworkers; which tasks you handle. Take independent charge of those tasks. Be realistic of course, because you can’t achieve much in a stolen hour. But at least when you don’t have the cost of coordination, you’ll spend all the energy you can steal, in doing what you’ve signed up for.

Working independently is a remote working superpower. Don’t forget, dividing and conquering a problem is also collaboration.

Take a “ship-show-ask" mindset

A couple of years back my colleague Rouan Wilsenach wrote an article about a branching strategy he calls “ship-show-ask”. While Rouan wrote this with code in mind, I think the mindset applies broadly to all kinds of work. When you complete a piece of work, you have three choices - ship, show, or ask. The table below describes each choice when you should make it,  and what percentage of work it should apply to. 

When you limit your “ask” choice to just 10% of your work or less, it helps you default to action. Especially if your collaborators are also busy people. If it becomes the team culture, then even you as “the busy person” will rarely bottleneck others. 

Do less. Do better. Don’t be a bottleneck.

The best advice I’ve heard as a product manager is to “do less”. Great products often do a few things well, rather than doing many things at a mediocre standard. 37Signals advocates this approach as building half a product and not a half-assed product. This same thought process applies to general work as well.

Busyness is often a product of saying “yes” to too many things. Before you know it, you’ve not just signed up for too much, you’ve also made yourself a bottleneck for many other people. We’ve all tried to work with that one person who is so busy that they never meet their commitments. They’re late or sloppy or rushed or all of these. Don’t be that person. Say “no” more often than you say “yes”. Pair this with the ability to work independently, and you’ll see that you’ll do better work. You also won’t block other people with your busyness.

Embrace the law of diminishing returns

As I said at the start, the path to hell is paved with good intentions. When we invite more people to work with us on a project, we have good intentions. We want to be inclusive and “collaborative”. This comes with the additional cost of coordination. Similarly with every decision we make, we want to get it right the first time. So we invite everyone who might have an opinion, to weigh in with their thoughts. This slows down decision-making.

There’s a point after which adding more people to a problem doesn’t just have diminishing returns, it’s counterproductive. You reach that point fast with busy people. The more the dependencies, the slower you progress.

Instead, make peace with the law of diminishing returns. Be wrong at speed. Focus on shipping imperfect work early and getting feedback. Do what it takes to improve your decision velocity. If you’re a busy person, you’ll realise that the speed of iteration will be a far more reliable marker of your productivity, than the quality of each iteration. 

If you’re an unavoidably busy person, then be realistic about how productive you can be. Make peace with the fact that you won’t do much on a fragmented calendar. If you recognise this reality, you’ll make the right decisions about how much you sync up with others and how many things depend on you. Doing less will be a more natural decision this way. 

But if possible, avoid being so busy. In an age of AI-led disruption, you must have skills that AI can’t replicate. You won’t build those skills sitting in meetings, will you?