Success stories

Why Tasks Fall Through the Cracks (And How to Keep Teams on Track)

by: John Coburn
Why Tasks Fall Through the Cracks (And How to Keep Teams on Track)

Do you ever feel like you’re losing your grip on the mountain of tasks you need to accomplish? That no matter how hard you try, things keep slipping through the cracks?

Of course you have. We’ve all been there.

Yet, that disorganized and defeated feeling rarely comes about overnight. All too often, the gradual creep of undone tasks and mounting commitments builds and builds, until it leaps out at you and makes itself known at the least opportune time. 

Like most people, you’re likely being bombarded with instant messages. Emails. Papers landing on your desk. Verbal requests you have to jot down. Some of these messages may come from your boss, and some will come from your colleagues, while others make their way to you from clients and vendors. 

With demands coming at you faster than you can process, it’s understandable that you might feel anxious and overwhelmed. How can you get a hold of your day so that you feel like you’re back in control again? More importantly, how can you get your entire team on track as well?

Let’s start defeating that feeling of overwhelm by first narrowing our focus:

Defeat Analysis Paralysis 

A major problem plaguing most of us in the Information Age is that we have too many choices and too many competing priorities. Do we really need software dashboards with 30 different KPI charts on them? Or 250 different dishes on the Cheesecake Factory Menu?

The answer is no. We don’t. 

In fact, all of those options may actually be paralyzing us from making a decision.

The law of diminishing returns refers to a point at which the level of profits or benefits gained from an action is less than the amount of money or energy invested into it. To put it plainly, we don’t benefit from having 15-20 different goals because when everything is important, nothing is important.

Kick those “ought to” goals to the curb, and opt for a few “no matter what” goals. For instance, choose to focus on 1-3 of your most critical and widely important KPIs or goals. When you do that, the right things will fall through the cracks, and what’s really important will float to the top to be accomplished.

Empower Your Team to Say ‘No’


Best selling author Jim Collins said in his book Good to Great, “the enemy of the great is the good.” That’s truer today than ever. We don’t fail because we pursue bad ideas. We fail because we pursue too many “okay” or “good” ideas. 

But there’s an easy solution. Say “no” more often.

Start saying no today. Empower your team to say no as well. Say no to time-sucking tasks. No to busy work. While you’re at it, go ahead and empower them to say no to meetings

Tech entrepreneur and engineer, Elon Musk believes if you’re not adding value to a meeting, then you should leave. Whether you agree with Elon or not, you get the idea. Your time is a finite resource. The quickest way to get on top of your task load is to cut your commitments in half. While you’re at it, help your team feel empowered to establish firm boundaries and regularly enforce them too. 

One of the best ways to say no is by finding that one decision that can remove fifty decisions. Create blanket rules that make it easier to say no. For example, if you’re a writer who’s bombarded with requests to review people’s books, create an email template with a blanket statement about how you’re “taking a vacation” from giving book reviews. Problem solved, and nobody’s feelings will be hurt, since you’re saying no to everyone.

If you’re having a tough time figuring out what to say no to, try answering these questions:

  • What can I altogether remove, even if it’s temporary, in order to create the space necessary for seeing the bigger picture?
  • What’s the one thing I could accomplish each day that would make me satisfied with my day?
  • What’s the one thing I could accomplish today that would make all other tasks easier or unnecessary?

And if you’re still struggling to say no, try to say yes more slowly. Before committing to anything, ask more questions. 

Author Michael Bungary Stagnier wrote in his book, The Coaching Habit, “A yes is nothing without the no that gives it boundaries and form.” Put another way, when you’re saying yes to something, you’re also saying no to something else. Recognize those implications and trade-offs before committing by asking yourself, “If I say yes to this request, what will I say no to?”

Take a Hard Look at Your Schedule

Like most teams, yours is likely stuck between the daily whirlwind of the tasks that comprise their job function and the work that moves the needle on company goals and initiatives. 

By nature, the whirlwind of your daily job is likely reactive; you’re responding to the world’s demands in a neat and organized fashion, often in regular intervals, dictated by other people’s schedules. On the other hand, moving the needle on company initiatives and doing big picture work is commonly proactive and requires time to reflect — lots of uninterrupted time, specifically.

Co-founder of the influential startup accelerator, Y Combinator, Paul Graham wrote about this phenomenon in his article titled, Maker’s Schedule, Manager’s Schedule. Essentially, he argues, most bosses are on a manager’s schedule: you block off your day in hour blocks, and switch gears 8x a day or more. 

The maker’s schedule, on the other hand, is often used by creatives like writers, programmers, and artists who prefer to block their time in half-day increments at a minimum. That way, they get some much-needed ramp-up time and, hopefully, find themselves in the deep flow state where the real magic happens.

Working on the wrong schedule is a common reason that tasks go undone. For instance, if you’re a manager working on an ill-defined maker’s schedule, you’re probably not switching gears enough or using the time available to you wisely. Or conversely, you’re letting things fall through the cracks because you’re busy doing the wrong things. 

Busyness can be a form of laziness, especially if you allow it to take you away from the most critical tasks you should be working on. If you feel like you’re busy every minute of the day, but that key tasks are still evading you, it’s time to reflect on what exactly you’re filling your day with.

Deploy the Right Systems

It’s not enough to clean a messy room; it will inevitably get messy again if you maintain the sloppy, pack-rat habits that caused the mess in the first place. You’ll remain on this endless cycle of tidying, messing, and summoning the motivation to tidy again, unless you change the system behind it. 

Deploying the right systems in business is a game-changer. If you’re a project manager juggling a million different tasks without a system in place to capture, organize, and execute on them, you’ll be much less likely to succeed. Instead, you need an organized place to store documents, a consistent place to house your projects and to-dos, reminders, trustworthy reporting tools, and a streamlined way to communicate with everyone.

Fortunately, such systems are everywhere, whether you get the greatest benefit out of an all-in-one software systems like Taskworld, a framework like David Allen’s Getting Things Done methodology, or even workflow rules like Inbox Zero

Schedule Regular Check-ins


Deploying the right systems will give you much-needed clarity, but only if you use them consistently. Discipline equals freedom here, and without consistency, you’ll quickly fall back to your old habits and diminished performance.

To ensure you aren’t falling off track or letting critical tasks fall to the wayside, you’ll need to be structured and diligent about checking on your progress. Goals are just dreams with deadlines, and deadlines are what keep people accountable. 

Make your goals and deadlines visible, and remind your team of them often. In your one-on-ones and weekly/monthly team meetings, make it a point to check the scoreboard. Praise those that are meeting the standard or are ahead of schedule. Reflect on wins but, more importantly, reflect on losses. Learn from them and find a systematic way to mitigate them in the future.

What Can You Do Now

  • Narrow down the number of KPIs metrics you’re tracking. Give yourself a pat on the back if you can get down to just 1-3 top-level goals.
  • Find 3 tasks on your to-do list that you do regularly, but that don’t directly support your top 1-3 goals. Delegate them to someone else, or eliminate them entirely.
  • Add “check the goal scoreboard” to the agenda templates you use for your one-on-ones or team meetings. 

Remember, tasks only fall through the cracks when you don’t have a system in place to capture, organize, and execute on them. The fastest ways to free up bandwidth are to say no more often and to cut your commitments in half. Finally, you have to perfect the art of following-up. Follow up on your tasks, check in on your goals, and learn from your mistakes. Then — and only then — will you feel like you’re on track and in control.

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