How to Effectively Delegate and Avoid Stealing Success From Your Teammates

Time for a scary admission: I can be a bit of a control freak.

For the longest time, if I was asked about my biggest weakness, I would say just that – I have a hard time letting go of control especially if we’re talking about managing a project or a complicated task. I was the kid in school that preferred to work by himself rather than in a group (yeah…that kid). I knew I would do the project correctly. Someone else? They might screw it up.

As a result, I’d pile on tasks even if I was overwhelmed. If I took it on, I knew it would get done. That was all that mattered! If I did hand something off, I’d be sure to provide step-by-step instructions on how to get it to the finish line.

This might be a bit of an exaggeration. I’ve been steadily trying to get over this fear of letting go especially after I read Marshall Goldsmith’s What Got You Here Won’t Get You There. I’ve gotten better at handing over tasks and allowing others to run with ideas. Still, it’s an area that I’m constantly trying to work on – how to delegate effectively and allow others to crush projects on their own, without my needless meddling.

This concept of effective delegation popped up again recently as I read The 7 Habits of Highly Effective People. One of the habits (Put First Things First) spoke to this idea of delegating ideas. It broke down two types of delegation – Gofer and Stewardship – and described how the former steals success from teammates while the latter empowers them.

Let’s dive in.

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Juggling Roles

Over the past few weeks, one idea has surfaced again and again through podcasts, books, and articles I’ve read:

Multi-tasking (or having multiple priorities) is the key to failure. To succeed, you must identify one thing that takes precedence and accept mediocrity at everything else, so the prevailing wisdom goes.

This message has come up several times over the past few weeks from reading The ONE Thing by Gary Keller to a discussion with Angel List founder Naval Ravikant on the Spartan Up! podcast to an interview I listened to with Greg McKeown, author of Essentialism. I think it’s worth separating out what I see as two different types of multi-tasking:
  1. Trying to do two different tasks at the same moment in time (like trying to watch TV and also listen to your friend tell a story).
  2. The multi-tasking we all do on a daily basis as we juggle the various roles we all play (team member, writer, husband, mother, father, etc).
It’s well documented that the former variation doesn’t work. You’ll get a much better return on investment by single-tasking – devoting all of your energy to one task at a time. Read Deep Work if you’re not convinced. The second variation – juggling the many roles we all play on a daily basis – is where I tend to disagree with the prevailing wisdom. Continue reading “Juggling Roles”

The Planning Fallacy: Why We Overcommit And How to Stop

Picture this: You have a day packed with meetings and obligations. Then, your best friend asks you to go out to lunch. After examining your calendar, you find a 45 minute block around noon that could work. You would still need to drive to the restaurant, order as soon as you arrive, and then get back to the office by 12:45pm to prep for your next meeting.

We’ve all been in a scenario something like this in the past, right? We’re already scheduled to the max, but a juicy opportunity presents itself so we squeeze it in determined we can make it work. More often than not, it fails. We’re late to the next meeting, over the deadline, stuck in traffic, etc. If “to err is human,” it seems like “to overcommit” is human as well.

Although it’s probably obvious, it’s worth diving into why overcommitment should be avoided. First, it puts us in a situation where we overpromise and underdeliver. That’s certainly not the fastest way to the corner office. Second, we’re putting ourselves in a stressful situation. Comparing your calendar and todo list only to find out you have absolutely no time available to get it all done? Not fun.

Why do we do this to ourselves? Why do we overcommit to projects, events, meetings, and tasks in the first place? In order to understand answers to those questions, we first need to understand why we’re so bad at predicting the future. We’ll look at research from The Black Swan by Taleb, Stumbling on Happiness by Gilbert, and others to help us understand and more importantly, improve.

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Tools I Use to Manage My Time

This week’s Support Driven writing challenge is all about productivity. The prompt: “What tools do you use to manage your tasks and time?”

I’m a productivity nerd. I’ll admit it. I spend far too much time reading books and blogs about various workflows and testing out different apps and trackers. I’m fully aware of the irony.

Over the last year or so, I’ve started to hit a groove though. I’ve stuck with the same tools for quite awhile now, and I feel pretty sane from day to day. I’m able to get a lot done while still staying inside the normal boundaries of a workday. Here’s the current setup I use to get everything done.

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Know Thy Time

Although the title of this post is influenced by Drucker (again), I actually want to share two articles I’ve come across recently on time management and “time reflection” (if that’s a phrase).

The first is by Julie Zhou on Medium—What do I do at work all day? I always enjoy reading about how other individuals manage their time and get things done.

If you asked me What does a normal day look like for you? I’ll probably rattle off some vague answer about spending half my time on product and half of my time on operations (recruiting, 1:1s, etc.)

I have no idea if this is actually true, so I decided to do an audit of my calendar.

The second is from Chris Bowler about a process for consistent weekly reviews.

A good weekly review should less about what your overall list of responsibilities and more of a review of what you’ve just accomplished in the week past and how you’re going to get closer to your most important goals in the week to come.

I’m going to incorporate a good bit from Chris’ post in my own weekly reviews this week.

Getting the Right Things Done

I’m in the process of reading The Effective Executive by Peter Drucker. One of the main threads in the book is “Know Thy Time.” The point is simple—effective individuals understand where their time is going. More importantly, they understand where their time should be going and work to reconcile the delta between the two.

As I was reading the chapter, I realized I was doing well at the first part; I knew roughly where I was spending my time. I use Todoist to track tasks, a paper notebook for staying on top of appointments, and RescueTime to automatically log how long I spend on various apps/websites on my computer.

How do you take that next step though? How do you actually do anything with that information?

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This is How I Work

I’m a huge fan of the Lifehacker series “How I Work.” They interview everyone from photographers to entrepreneurs to chefs and beyond looking at their workspace, favorite apps, etc.

It’s highly unlikely that they ever come to me asking for an interview so I thought I would borrow their format and complete my own “How I Work” interview. Here it goes!

I would love to read yours. If you write your own, can you drop a comment here on this post so I can read it? Or, tweet at me (@jeremeyd).

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Does that matter?

A screenshot of the header to Fried's blog post "Does that matter?"

Jason Fried, founder and CEO of Basecamp, published a great piece on Signal vs. Noise that I just stumbled upon thanks to Twitter.

Being able to see what matters, to know what’s worth doing is an instinct you can hone, a skill you can build. I’d consider it a top requirement for anyone tasked with making key decisions.

I would expand that to say it’s a top requirement for anyone. Making key decisions about what to work on is something we all face.

I’ve had the same conversation a few times now with new Happiness Engineers that start at Automattic. When they first join the company, they’re obviously excited and ready to make a big impact. They dive right in to every project they find helping out here and helping out there.

For a short time, the juggling act works, and everything is sustainable. Over time, the foundation starts to crumble, and they become overwhelmed, forced to take things off their plate to maintain some sense of sanity.

I know this feeling all too well because it happened to me.

Continue reading “Does that matter?”

What I Mean When I Say “I Don’t Have Time”

What I Mean When I Say I Don't Have Time

I have three habits I’m focused on right now – reading, meditating, and stretching.

I’ve been knocking it out of the park on the first two (roughly 85% or higher completion rate). The stretching? Well, I’ve done that once in 24 days for an abysmal 4% completion rate.

The actual habit isn’t that difficult. Every night I want to spend five minutes total stretching my hip flexors and upper back. I can do it while watching TV and even drink wine in between (or during!). Still, I fail every single night. If you were to ask me about it, I would probably create some excuse centered around not having enough time and being so busy with chores, which would be a lie.

“I don’t have time” is never the real reason.

If I think a bit deeper, I’m normally saying one of the following.

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Majoring in the Minor

If you’ve stumbled across the blog over the past few days, you’ve seen an absolute nightmare. I’ve changed the site design more than five times over the course of the past week. I just couldn’t make up my mind on how I wanted to present myself online.

Meanwhile, I haven’t actually created a piece of original content in over a week. I’ve completely missed the point.

Continue reading “Majoring in the Minor”