Actually, the exact language that started this coaching call was, “Help! I’m failing! I just met with my boss and she said to me, ‘I don’t know what’s happened. You used to be the one I could count on to get things done. Lately, though, you’ve been dropping the ball.’” My client was distraught, feeling like they’d gone from being the “A student” to having their work redlined. And, because they had attached so much of their self-worth to being that “go-to” person, this felt like they were being outcast.
As we talked it through, it turns out that the company had been in a rapid growth phase, so, not only were there more projects but they were more complex and more visible. On top of that, they’d lost a few employees and hiring was taking longer than anticipated. The sheer magnitude of things on this person’s plate had grown exponentially over the course of the past year. And not wanting to remain that key player and not disappoint his boss, he’d continued to take on whatever she threw at him.
As a result, deadlines were being missed, work was not being done to his usual standard and he was working harder and more than ever before.
The first thing we did was to assemble all of these “to-do’s” in one place. It turned out to be a page-and-a-half single-spaced typed document. Seeing it all in one place was eye-opening to him. And, closer examination of these points pointed to several of them being projects, not tasks. For example, one line read, “prepare board presentation.”
Next, I had him prioritize the list into four buckets. I love to use the Eisenhower Matrix to guide this work. This breaks things down into Important and Urgent, Important but not Urgent, Urgent but not Important, Not Important and Not Urgent. 
When he finished, he ended up with 5 things in the Important and Urgent bucket. As we discussed each of them, it turned out that one was already overdue. If the ‘deadline’ has already passed and the sky hasn’t fallen, I question how real the urgency was. So, we agreed that this would be an item for discussion with his boss to understand what the true urgency of this was. Beyond that, there were 3 others that were due in the next week. We chose to focus on those.
One of those was the task “prepare board presentation” that I previously mentioned. I had him break this down into its component parts. Next, we noted any task that could be delegated to someone else. And finally, I asked him to assign how much time it would take to complete each of these items. I then had him multiply this estimate times 1.25 as I find that we tend to overestimate our ability to get things done, or underestimate how long things actually take.
With that, we turned our attention to his calendar. Was there enough time in his day to complete these tasks? Were there meetings that he could bow out of or delay? It’s okay to put in extra effort once in a while but when it becomes the norm, it can lead to burnout and the quality of work can suffer.
Armed with all of this, he felt ready to go back to his boss to have a conversation about all that was on his plate, how he had prioritized the work, and his proposed plan for addressing it. This dialogue will enable them to be better aligned on what he’s focusing on and what support he might need.
As important as it was to help him craft a plan that saw him regaining control of his workload, it was equally important to help him begin to see the disservice he was doing to himself and the organization by taking on more than he could reasonably accomplish. Additionally, our Eisenhower Matrix exercise helped him to see just how much of the work on his plate was less important for him to be doing. By delegating, delaying or dismissing these tasks, he could focus on the higher-order, more impactful work that he’d come to be known for.

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