Question
How should one deal with a coworker who consistently waits until the last minute to ask for things?
Answer
This is not enough information to answer the question. The necessary tactics are very different depending on lots of missing situational details.
1. WHY does he wait? The Friday pattern suggests a specific cause. I suspect there is a customer in the loop here, otherwise there wouldn't be the pressure you are indicating. Does he have his own customer meetings or something that lead to actions that he promises he will deliver?
2. What is the organization structure? Matrix? Sales engagement teams? What? How many levels above do your reporting paths converge to one person? What is this person's relationship with his management chain? How weak/strong is his chain relative to yours?
3. What is the culture of the organization overall? Is it a hard-driving, brutal one, or a more relaxed work/life balance one? Is he an outlier or are you? Do others share this perception of him?
4. What is the context of these requests? Direct 1:1 to you, or cc'ing an engagement team? What is your non-dotted-line manager doing in this picture?
5. What are the consequences to you of taking the obvious hardline (set expectations of more notice, and actually follow through and NOT fulfill the next request that violates the hardline expectation)? Can he get you fired? Cut you out of juicy projects? Direct work elsewhere to someone who will be more willing to accommodate him? Are you an irreplaceable unique person in the situation who is oversubscribed? Or a replaceable person who is undersubscribed?
I am happy to help via message if you don't want to share these details publicly.
I have to warn you though: the right answer may be "there's nothing you can do other than quit or move to a different role."
1. WHY does he wait? The Friday pattern suggests a specific cause. I suspect there is a customer in the loop here, otherwise there wouldn't be the pressure you are indicating. Does he have his own customer meetings or something that lead to actions that he promises he will deliver?
2. What is the organization structure? Matrix? Sales engagement teams? What? How many levels above do your reporting paths converge to one person? What is this person's relationship with his management chain? How weak/strong is his chain relative to yours?
3. What is the culture of the organization overall? Is it a hard-driving, brutal one, or a more relaxed work/life balance one? Is he an outlier or are you? Do others share this perception of him?
4. What is the context of these requests? Direct 1:1 to you, or cc'ing an engagement team? What is your non-dotted-line manager doing in this picture?
5. What are the consequences to you of taking the obvious hardline (set expectations of more notice, and actually follow through and NOT fulfill the next request that violates the hardline expectation)? Can he get you fired? Cut you out of juicy projects? Direct work elsewhere to someone who will be more willing to accommodate him? Are you an irreplaceable unique person in the situation who is oversubscribed? Or a replaceable person who is undersubscribed?
I am happy to help via message if you don't want to share these details publicly.
I have to warn you though: the right answer may be "there's nothing you can do other than quit or move to a different role."