100 Questions to Ask Before Delegating a Task

No.	Item	Definition
1.	Are there accessibility needs?	Checks inclusion requirements.
2.	Are there approval steps?	Checks required approvals.
3.	Are there compliance needs?	Checks regulatory requirements.
4.	Are there dependencies?	Checks linked requirements.
5.	Are there known blockers?	Checks existing obstacles.
6.	Are there stakeholders?	Checks interested parties.
7.	Can anything be automated?	Looks for automation opportunities.
8.	Can anything be reused?	Finds reusable assets.
9.	Can anything be simplified?	Looks for easier options.
10.	Can deadlines move if needed?	Checks schedule flexibility.
11.	Can I involve others?	Checks permission to collaborate.
12.	Can I make trade-offs?	Checks flexibility on choices.
13.	Can I see a template?	Requests a model format.
14.	Can priorities change?	Checks for shifting focus.
15.	Can this be broken down?	Splits work into parts.
16.	Do you have a checklist?	Requests a task list.
17.	Do you have a deadline buffer?	Checks schedule cushion.
18.	Do you have a preference?	Asks for favored option.
19.	Do you have brand guidelines?	Requests style rules.
20.	Do you have examples?	Requests sample work.
21.	Do you have source files?	Requests original materials.
22.	Do you need a draft first?	Checks draft requirement.
23.	Do you need my recommendation?	Checks advisory role.
24.	Do you need options or one?	Clarifies number of choices.
25.	Do you need sign-off?	Checks approval requirement.
26.	How detailed should updates be?	Sets update depth.
27.	How flexible is the plan?	Shows room for change.
28.	How formal should it be?	Sets tone expectations.
29.	How much autonomy do I have?	Defines decision freedom.
30.	How much time is expected?	Sets time expectations.
31.	How often should I report?	Sets reporting frequency.
32.	How sensitive is this?	Shows confidentiality level.
33.	How should decisions be made?	Clarifies decision process.
34.	How should I approach it?	Guides working method.
35.	How should I communicate?	Specifies communication style.
36.	How should I prioritize it?	Guides order of work.
37.	How should issues be raised?	Defines issue escalation method.
38.	How urgent is this?	Shows the priority level.
39.	How will progress be tracked?	Sets tracking method.
40.	How will success be measured?	Defines measurement criteria.
41.	Is there a backup plan?	Checks contingency readiness.
42.	Is there a fixed budget?	Checks spending flexibility.
43.	Is there a hard deadline?	Checks deadline flexibility.
44.	Is there a legal risk?	Checks compliance concern.
45.	Is there a preferred vendor?	Checks supplier preference.
46.	Is there a privacy concern?	Checks privacy risk.
47.	Is there a required format?	Checks format rules.
48.	Is there a review process?	Checks approval workflow.
49.	Is there a security concern?	Checks security risk.
50.	Is this the top priority?	Confirms ranking importance.
51.	Should I ask before acting?	Clarifies approval needs.
52.	Should I follow a template?	Checks for standard format.
53.	Should I involve finance?	Checks finance review need.
54.	Should I involve IT?	Checks technical support need.
55.	Should I involve leadership?	Checks executive involvement.
56.	Should I involve legal?	Checks legal review need.
57.	Should I mirror past work?	Checks consistency with history.
58.	Should I optimize for quality?	Clarifies quality priority.
59.	Should I optimize for speed?	Clarifies speed priority.
60.	Should this be delegated?	Checks if delegation fits.
61.	What are common mistakes?	Highlights frequent errors.
62.	What are the constraints?	Defines limits and boundaries.
63.	What are the deliverables?	Lists required outputs.
64.	What are the priorities?	Ranks what matters most.
65.	What are the requirements?	States mandatory conditions.
66.	What context should I know?	Provides background information.
67.	What could block progress?	Identifies likely obstacles.
68.	What data do I need?	Identifies needed information.
69.	What dependencies exist?	Shows linked tasks or inputs.
70.	What does success look like?	Defines the expected result.
71.	What exactly needs doing?	Specifies the required work.
72.	What examples can you share?	Provides models to follow.
73.	What has been done already?	Avoids duplicate work.
74.	What information is missing?	Reveals knowledge gaps.
75.	What inputs are required?	Lists necessary materials.
76.	What is in scope?	Defines what to include.
77.	What is out of scope?	Defines what to exclude.
78.	What is the budget?	States spending limits.
79.	What is the deadline?	Sets the due date.
80.	What is the goal?	Clarifies the desired outcome.
81.	What level of detail?	Sets expected depth.
82.	What output format is needed?	Specifies the final format.
83.	What policies apply?	Names relevant rules.
84.	What process should I follow?	Sets the workflow.
85.	What quality bar applies?	Defines quality expectations.
86.	What resources are available?	Shows available support.
87.	What risks do you see?	Surfaces possible problems.
88.	What should be avoided?	Names things not to do.
89.	What standards apply?	Names required standards.
90.	What system is involved?	Identifies the platform.
91.	What tools should be used?	Specifies preferred tools.
92.	Who can answer questions?	Points to a resource person.
93.	Who decides final approval?	Identifies the approver.
94.	Who else is involved?	Identifies collaborators or stakeholders.
95.	Who is affected?	Identifies impacted people.
96.	Who is the audience?	Names the intended users.
97.	Who owns the outcome?	Identifies final accountability.
98.	Who requested this?	Names the original requester.
99.	Who should be informed?	Lists people needing updates.
100.	Why does this matter?	Explains the task’s importance.