How do I give someone a stretch assignment with appropriate support?

Start by defining the stretch as a learning opportunity with a manageable piece of real work. Be specific about the skill they can practice and why this task offers that chance. Then decide what a useful outcome looks like, what the assignment does not include, and what support you can actually provide.

For example, assuming the task is to coordinate a small internal project, the learning goal might be practicing planning and stakeholder updates. The assignment could include drafting a schedule and leading one update meeting. It would not automatically include owning the wider program, approving spending, or resolving every dependency. Adjust those placeholders to fit the real role and work.

Before making the offer, check that the person can reasonably take on the task alongside existing priorities. If something else must move, identify who will agree to that change. A stretch should involve a new challenge, not silently adding unlimited work.

Frame boundaries as part of the assignment design, not as a warning about the person. Say what they can decide independently, where they should check with you, and which decisions remain with someone else. Also name what is intentionally outside scope so that taking initiative does not turn into guessing about authority.

You could say: “I’d like you to lead the planning for [specific project or workstream] as a chance to practice [skill]. You can propose the schedule and coordinate the agreed participants. Please bring changes to [scope, budget, or deadline] to me before committing. This does not include [excluded responsibility]. We’ll agree together if the work needs to change.”

Use only boundaries that apply to the actual assignment. If you are unsure whether the person has authority to make a decision, clarify that before work begins rather than relying on them to infer it.

Agree on support in practical terms: a named person to consult, time for guidance, access to relevant materials, and check-ins at useful decision points. A check-in should make room for questions and changes, not just status reporting. Ask the person how they prefer to raise a concern, and tell them what to do if an issue cannot wait until the next meeting.

For the example above, you might agree on a short kickoff, a review of the first draft schedule, and a check-in before the update meeting. These are illustrative options, not a required cadence. Choose intervals that fit the task and the support you can reliably provide.

Make it acceptable to say, “I’m blocked,” “I need a decision,” or “This is larger than we agreed.” If they raise a concern, respond by clarifying the decision, adding guidance, adjusting scope, or pausing the work—not by treating the request for support as a lack of effort.

Use a brief written agreement and review it together. Fill in the brackets before starting, and leave out any category that does not apply.

Stretch-assignment agreement

• Assignment and learning goal: [task] gives [person] a chance to practice [skill or responsibility].
• Useful outcome and date: [deliverable or sign of progress] by [date or review point].
• Scope: [included work]. Not included: [excluded work].
• Decision boundaries: [decisions the person can make]; ask [named role or person] before [decisions requiring approval].
• Support: [guide or adviser], [available time or materials], and check-ins at [points or intervals].
• Workload agreement: [existing work that will be paused, reduced, or kept as-is].
• When to pause or adjust: If [scope, time, authority, or workload changes], [person] will flag it to [contact]. Decide together whether to clarify, reduce, extend, reassign, or pause the work before continuing beyond the agreed scope.
• Review: On [date or milestone], discuss what was learned and what support or next step would be useful.

Ask the person to suggest edits. The agreement should reflect a real conversation about capacity and support, not just a form they are expected to sign.