Study Hacks Blog

Don’t Delegate Using Email

August 13th, 2020 · 16 comments

On the most recent episode of my podcast, Deep Questions, a listener asked for my advice about delegation. This is an important topic that I haven’t talked a lot about before, so I thought it might be useful to sharpen and elaborate the answer I gave on my show.

In the office setting, most delegation occurs over email. You need something done that you either don’t have the time to do, or don’t want to do, or don’t know how to do: so you shoot off a quick message to put in on someone else’s plate. Our current moment of remote work has made these electronic hand-offs even more frequent.

As I explained on my podcast, however, I think this is a problem. You’d probably be better off if you instead worked backward from a simple rule that will make your life more annoying in the short term, but significantly more productive in the long term: don’t delegate using email.

Before we discuss how this is even possible, let’s touch on why it’s important.

When handing off tasks, email’s extreme efficiency can become a liability. It nudges you toward temporary relief of psychic discomfort. You think of something that you don’t want to forget, so you dash off an email: look into this and get back to me! Something new arrives in your inbox, creating a brief moment of obligation — oh no, something else I have to make time for — that can be dispelled with a quick forward of the message to a colleague.

I call this relief temporary, however, because you haven’t actually dissipated the discomfort. A quickly composed, ambiguous delegation email only passes this discomfort onto its recipient, perhaps even increasing the distress, as you’ve likely left out details clear to you, but not to the person grappling with your hasty missive. To make matters worse, this ambiguity will then require many more additional back-and-forth messages to try to approximate some clarity, further multiplying and spreading the cognitive toll of the original task.

When you instead enforce a simple no email delegation rule, this instinct to sacrifice the greater good for a smaller personal respite is stymied. Solutions that are overall more productive suddenly become necessary.

On my podcast, for example, I talk a lot about task board software, like Trello, Flow, or Asana. Instead of allowing tasks to exist implicitly among emails buried in an inbox, why not instead isolate and clarify them as standalone cards on a virtual task board? Now it’s clear who is supposed to be working on what, and all the information relevant to a given task can be appended to its card, instead of fracturing itself among impromptu email threads.

The person doing the delegation must now clarify what exactly they’re delegating. When creating a new card for a task, as opposed to dashing off a message, you’re forced to actually think through and articulate exactly what it is you want, when you need it, and what information will be required to get there.

These tasks boards also make it difficult to escape exactly how much you’re asking someone to do. It’s easy to shoot off a dozen emailed requests to a colleague throughout a busy day without thinking much about it. But when you instead see each card piled on top of another in that person’s column on a task board, the magnitude of what you’ve dispensed is unavoidable.

For quick tasks that arrive in the form of emails, I’ve also found ticketing systems to be useful. This allows messages to be transformed into tickets that can be assigned to specific team members, appended with notes, and labeled with their current status. This is how, for example, in my capacity as the Director of Graduate Studies for my department at Georgetown, I coordinate incoming email issues with my Graduate Program Manager (we use FreshDesk).

I can tell you from personal experience that the extra hassle in the moment of moving questions and requests into this system is absolutely worth it. The added structure of the ticketing system significantly reduces stress as compared to the alternative of attempting to juggle all of these obligations through an amorphous and ever-increasing tangle of undifferentiated emails.

I don’t want to fall too far down a productivity process rabbit hole here. My main observation is that when it comes to delegation, don’t be seduced by the promise of a temporary fix to the momentary crisis of having something new to wrangle. Email doesn’t have enough friction. It’s better to embrace a more structured system for identifying, describing, assigning and reviewing tasks that trades slightly more work right now for a significantly decreased cognitive toll for your organization in the future.

16 thoughts on “Don’t Delegate Using Email

  1. Joe says:

    I just cycled through a dozen emails and put them in a spreadsheet, that I designed, because our university leadership won’t do this for IT and instructional design issues. Keep banging the drum for us Cal, eventually people are going to have to listen.

    1. Jared Wyllys says:

      Right there with you. I teach high school, and the culture where I work is very much through email. Everything is delegated that way, and co-workers carry out all kinds of conversations via email, too. Hoping eventually more people will move on to more efficient tools.

  2. In the past, I’ve had bosses who would receive an email, and literally forwarded it on to someone else (usually me), without even adding a message in the forward section. Was tempted to forward to my trash can.

    But seriously, I haven’t listened to the podcast yet, so maybe you covered this, but, another point worth considering is the ‘CC and ‘BCC fields. These fields get seriously abused. The amount of email I get ‘CC into when it has absolutely nothing to do with me is worrying. I wish I could get all the time back I spent half reading emails, only to realise I don’t need to read them in the first place.

  3. CM says:

    Totally agree, it is worth it for all involved to put time and effort in on the front end of any request. Reminds me of your technique from Deep Work about ending the 5 back and forth emails about scheduling meetings and just deciding on one and letting the person know to let you know if it doesn’t work. I love that trick so much.

    We use Monday at my organization and it is wonderful. Any project management software has to be better than email delegation! I wish everyone would get on the software and invest in using it as our primary form of communication to the degree that email becomes understood as a tool to communicate only with those outside the organization.

  4. Paula says:

    All I can say is “amen.” Well, I could say a LOT more, and “amen” will suffice.

  5. Jesse says:

    Makes perfect sense.

  6. Blair says:

    You make some good points, but I’m not convinced that email is a poor tool for delegation. Email is a low-friction medium that allows for poor quality delegation, but that is more of a commentary on our leadership habits and our inability to delegate effectively. What I’m curious to hear about is your take on Stewardship Delegation, as described in Steven Covey’s “7 Habits of Highly Effective People.” Summarized, proper delegation means informing your teammate(s) in detail of your desired results, guidelines or constraints in which to complete the task, resources available to help them, who they are accountable to and by when, and the impact their work will have when completed. “Read this and tell me what you think” is poor delegation, whether done via email or other means.

    The questions that task management software forces you to ask are simply guiding you towards stewardship delegation, which is a keystone habit that can be expressed in virtually any medium.

    The other sticking point is that getting organizations to culturally adopt task-board like software is an uphill battle for many. I’m sensitive to the idea that adopting these tools on an individual level can give team members yet another tool with which they must interact to keep track of their work. An employee working on many projects may have equally as many task tracking systems that must be kept up with. Personal productivity systems, in my experience, work best when information needs to be transferred between as few tools as possible.

    I agree that excessive email is a problem, and I’m looking forward to your next book about how to work without it. I’m specifically interested in how we can make these changes at organizational levels, without turning upside down the productivity systems that those of us who have been paying attention have so carefully developed.

  7. Chris says:

    The big issue I have is that I have my obligations already and if you send me a new piece of work through email, half the time I am not going to get it. So, if it was important it is not going to get done. And, if it wasn’t important it is not going to get done.

    If you give me something more tangible. That I’ll look into it.

  8. Hi Cal, thanks for the insight. Between Trello, Flow, or Asana, which one you recommend?

  9. When you have no trusted systems, email becomes your trusted system, unfortunately.

    I’m an executive at a small defense startup (i.e. dynamic) and I send at most, 1-3 emails each day. I send zero to my boss all week.

    Here’s how:

    1. I have standing meetings with everyone that I work for, and who works with/for me, each week.

    2. We publish a shared/collaborative meeting document/agenda on Google docs.

    3. During the week, we add tasks/questions to it (vice sending emails). This works for anything that falls into the important-but-not-urgent box (https://jamesclear.com/eisenhower-box). Anything hot, we jump on a call.

    4. Once a week, we synchronously review the shared doc to establish outcomes for the future (i.e. delegate/clarify tasks, project status, etc.).

    This approach produces the following outcomes:

    (1) I send no email.
    (2) I receive limited email.
    (3) I spend about 10 mins/day writing or responding to emails.

    There are two critical components for this system to work:

    1. The meetings have to occur each week, without fail. If we can’t rely upon the meetings, we fall back to email, and that’s no bueno. Otherwise, we can be guaranteed that we’ll discuss, with great clarity, anything on our shared agendas in less than 7 days.

    2. Our agenda clearly list the following items in the due outs section: (a) Next Action (or outcome) (b) Owner (c) Suspense date.

    It’s wonderful world to live in… ?

  10. “…you’re forced to actually think through and articulate exactly what it is you want, when you need it, and what information will be required to get there.”

    Sadly you’re asking for a lot from most people. I try to give people the benefit of the doubt though when they do this and assume they have so much going on that they can’t take the time to do this. But there are probably plenty of people that are just being lazy.

  11. So true. An email takes two minutes to dash off, and the emailer has checked the box in their head of DONE. These are what I’ve seen:

    1. Information Source: this is a merry-go-round hard to get off once you get on it. One of my past bosses said we needed to answer every question we got, even if it had nothing to do with our jobs so I got seen as an information source (and when the information was available on a website that they could have visited). This one’s insidious because once you’re on the merry-go-around, any kind of help however little keeps you on the information list. I finally got off it by either deleting the email and not responding or emailing, “I’m sorry. I don’t know anything about that.”

    2. Fake Praise: Always done in email, since it sounds like what it is in person. It’s “Oh, you’re so good at this. You could do it in five minutes and it’d take me ALL day! Can you take care of it?” Usually they go overboard on the praise. One time, a coworker didn’t answer a question from someone else in a “timely” manner (read: coworker was supposed to be waiting for the instant the email arrived)), so other person emailed me lathering up fake praise while disparaging the other person. She was trying to get me to do this thing for her that she said was urgent. I just told her that coworker would respond when she saw the email.

    The other problem with delegation like this is that it really disrespects the other person. It sends them the message that you think they don’t have anything better to do or that what they have isn’t all that important and can be dropped at a moment’s notice.

    1. James says:

      “It sends them the message that you think they don’t have anything better to do or that what they have isn’t all that important and can be dropped at a moment’s notice.”

      This article rubbed me the wrong way, and your statement quoted above is the heart of it.

      In my company there are multiple ways to get in touch with someone–IM, email, in-person, phone calls, text messages, etc. If I need something right away, I call you. If I need it quick but not immediately I’ll IM you saying “I need X; do you have time to discuss?” Email is for those things which are important but which do not require an immediate response. The expectation is that you’ll look at it when it’s convenient for you–it’s sitting there waiting for you, but if it was a rush job I’d have called. Email is also used to transfer some files (yes we have other systems, but email is convenient and good for working documents). There’s a record of it, yes–but it’s not open to the entire team, not easily, and you can make it clear that the file is a work in progress.

      I’ll grant that this is going to vary from company to company. It even varies from manager to manager. But I think that as long as you manage expectations delegation through email can be effective. There’s nothing inherent to email that makes you need to drop everything to deal with it (the way there is with IMs); it’s merely a cultural norm, and therefore it’s plastic.

  12. Krys says:

    A past company that I worked for brought in a consultant to teach better use of tasks in Outlook, specifically for personal task management and email management. I have used the “assign task” feature in Outlook when I was managing a group inbox. That way, emails were assigned directly to a specific person. It’s added to my task list and the assigned person’s task list. When the assigned person completes the task, it is completed in my task list. Only issue with this system is that the assigner and assignee are the only ones who can see the tasks.

    I have also used the “assign task” in Saleforce.com (SFDC). We customized the complaint tracking system in SFDC. My role was to assign complaints to the correct person to investigate the complaint. Everyone with access to the system could see the tasks, timelines, and notes. The task assignment works in all sorts of different areas of SFDC.

    My current employer uses SharePoint heavily. I have worked with our IT folks to build us a page to intake and track requests of our group. Currently, requests come in via a group inbox. We “assume” that the correct person handles requests for their assigned responsibilities. Not a great accountability system. This SharePoint site will track all requests. We need to log when they are complete. We can see all of the statuses of the group requests. Other groups have created similar systems here and it works great. It allows for notes, links, and attachments.

    Lastly, we also use MS Teams. There is a Planner app in Teams that is pretty awesome too. Great for larger projects.

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