Elegant Delegation with Clickety

Part of the Mechanics of Leadership series. Everyone knows great leaders delegate. Ok. But how?

Micromanagement is a common failure mode: “I assigned this yesterday, where is it?” Constant checking in, specific and immediate demands, no room for creativity, people sending updates instead of getting work done.

Abandonment fails on the other side. Assign the problem, forget about it, and learn by chance three months later whether it was done or not.

Most people strive not to fall to either side. But it’s hard. You end up with a short list of stuff you’re good at checking up on, and then a much longer list that scrolls up the inside of your eyelids when you’re trying to sleep.

It’s confounding that such a core part of management is so hard. I’ve talked to dozens of people about how they do this – first when I was trying to learn it, and later when I was trying to make it better – and I’ve found no general purpose solution that people would recommend to others.

How Does This Work Today?

Let’s be cautious with the word ‘work’ here, because for most people it just doesn’t.

People seem to fall into three groups:

• Natural talent: They remember everything, are great at bringing up issues, and naturally apply just enough follow up but not too much.
• Disciplined: What they lack in talent they make up for in having a strong system that they apply ruthlessly. They put the time in, making lists and checking items off. It’s not fun, but it works.
• Everyone else: They muddle through doing the best they can. The disciplines are too much for them, and they don’t have the natural skills to fall back on without a bunch of discipline to match.

I figure about 10% of people fall into each of the first two categories. What about the 80% of the population not reliant on discipline or talent? They have a huge collection of solutions, none of which work that well. Let’s run through a small collection of what I’ve seen people use. Keep the smelling salts near:

• Outlook notes: Write it down, every time, for every single person. Ever. It’s that simple. Variants of this put the notes in Evernote, Apple Notes, or something similar. (Works great, until back to back meetings mean you can’t remember everything.)
• Post Its: Oldie but goodie. Piles of paper scattered around. This has the upside of being easy, but is brittle. You can’t move them around, there’s rarely enough information on a given card, and turning a list of post-its into a clear next step is pretty hard.
• Email snoozing: “Maybe next week.” This works ok for problems that only occur in email, and which you can solve while in front of your inbox. But… do you really want to spend more time in your inbox?
• Trello, Asana, Things, OmniFocus, etc: You can abuse any task management tool to help you track what you owe and who owes you things. But it’s hard to keep at them, because, well, it requires discipline. And these aren’t built for your job, so there’s a constant conflict between the work you want to track and what they’re good at. Only Things and OmniFocus capture references to emails, for instance. None can capture calendar events.
• Bullet journals, GTD, etc: These are a subset of discipline, but have the upside of being a system someone else has created and can help you with. It still requires a lot of discipline, but not as much as creating your own system does.
• Custom tools: This can be in Airtable, Notion, or something like that, or custom code. These are the best and worst of all worlds. They are exactly what you want, except… you probably don’t have a full dev team devoted to them. They end up low on features, brittle, and you can’t share them with other people. Even the people I’ve talked to who do have someone dedicated to their Airtable are pretty unhappy with it.

For every one of these, I can find at least one person who is succeeding with them right now. But I can find a hundred who used it for a month or three and then drifted away from it.

At Clickety, we’re so convinced there’s a better way that we’re building it.

Delegation and Follow Ups

The simplest way to think about delegation is as assigning work. No one talks about it that way – it exposes the whole “bosses get to tell you what to do” dynamic. It’s true, though. Sshhh! As a leader, if you delegate some problem or task to someone, you’re still on the hook if it fails. You’re relying on them to ensure it doesn’t.

This is almost the definition of leadership: Ensuring the right work gets done by the right people. It’s impossible without delegation.

It can be as simple as sending someone an email that you expect a reply to, or as complex as a month-long multi-person project . Someone else is working, but you own the deliverable.

Once you’ve assigned the work, you need to follow up on it. I mean. You don’t have to. See above re: abandonment. But, well, you should. This comes in many forms: Regular update meetings for more complicated projects. Check in during a 1:1 for smaller or more personal topics. Or just send a note once in a while to see how it’s going.

No matter what method you use, you need to know what you’ve delegated, and to whom. When you’re meeting with someone, you need quick answers to a couple of key questions: What is this person working on for me? What should I ask them about? Are they blocked on anything from me?

Most people call these “follow ups”. It’s hideous business-speak, but it’s what we’ve got.

This topic brought out more emotion than anything else in my user testing. And the emotions were all negative. Nearly everyone I talked to was sure there was something important they were supposed to be following up on, but they weren’t quite sure what. They could never relax. They had tried some of the tools and systems above but had failed to keep up with them. As a result they were lost, and they knew it.

The key to solving this is to build it around the interactions you have with the people you work with.

Anxiety-free Follow Ups with Clickety

In modern office environments, most follow ups are set in meetings or via email. We make it as easy as possible to mark that email or calendar event as needing a follow up. This will remind you, “I’m waiting on something from this person.”

This is as easy as BCC’ing us at followup@clickety.email on an email you’re sending:

We’ll then keep track of this email so you don’t have to.

When you next visit our app, that email and the person you sent it to will be marked with a ⏳. This visual indicator says that you’re waiting on something. Send more than one to the same person, and it will increment. You can scan any group and quickly see who you’re waiting on and for what.

One or two clicks, and you see the original email. Click to open and you can follow up right there:

Unfortunately not everything works as a BCC. You can also forward emails you receive:

Or just go to the app and mark them there:

Of course, not everything is an email. Events or manually activities frequently have some sort of deliverable, and you need to mark them accordingly:

We make it as easy as possible to capture what might need your attention. You won’t forget, and you know it.

You can learn more about how all of this works in our documentation.

Reviewing Follow Ups

Like any productivity tool, it’s easy to get lost. You might look up one day and know you’ve marked a bunch of emails and events, but… how do I find everyone? How can I be sure I’m reviewing everyone that matters?

In an ideal world, you’ll have created a context for the kinds of work you do, and everyone who matters will be in one of them. Review those contexts, and you can be confident you’ve hit everything.

But, well, we don’t live in an ideal world, do we?

We roll up every contact who has a follow up set into a Follow Ups group:

Here you can see everyone, regardless of how you work with them or what you’re tracking. In a glance you know what needs attention now and what can wait. No more late nights grinding, or lost sleep worrying.

Not everything gets done

One of the best productivity books of all time is David Allen’s Getting Things Done. He advocates for writing down every task you are thinking about.

Weirdly, it’s not because he wants you to get them all done.

Nope. The main point of writing them down is so you stop thinking about them.

We make it easy enough to track follow ups that you might end up with a ton of them. That’s fine. Most of them will deliver fine, and most of the ones that don’t, don’t matter.

The point isn’t to get more done (although you’ll do that), or to engage helpfully with the work you’ve doled out (you’ll do that too). It’s to give you confidence that everything you care about is being tracked. This lets you step back from the list, and focus on something else for a while.

Or you could, you know, sleep.

In the future

We’ve delivered the smallest, simplest solution we can. We love what we’ve built, and we think you will, too. But we also know it could do a lot more. Supporting timelines is one obvious feature: Don’t show before a certain date, or must be done by one. I’m eager to have follow-ups resolve automatically on a reply, or when a calendar event is scheduled.

If all of this intrigues you, sign up for the beta!. We’re excited to see what you can do with it.

We’d also love to hear at @clickety what you would like to see next.