Stretch Assignments That Grow People: A Manager’s Guide to Designing Developmental Opportunities

Stretch assignments are one of the most powerful ways to help people grow at work. They’re simple, practical, and grounded in real work learning — not just courses or theory. When done well, stretch assignments help people build new skills at work, gain confidence, and take on bigger responsibilities over time.

The challenge? Some assignments stretch people in a good way… and others overwhelm them. Here’s a clear, conversational guide to creating practical development at work that actually benefits people - not burns them out.

What a stretch assignment actually is

A stretch assignment isn’t about giving someone more work. It’s about giving them the right kind of challenge.

A good stretch opportunity is:

• New: something they haven’t tried before

• Challenging: just enough to push their comfort zone

• Supported: they have someone to ask for help

• Relevant: connected to real workplace situations

• Time-bound: with a beginning and an end

Think of it as a safe experiment in on-the-job growth.

Why stretch assignments work so well

People learn faster when they’re solving real problems and trying new things. Stretch assignments create natural workplace learning habits, like:

• thinking differently

• taking ownership

• asking for feedback

• adjusting along the way

This is learning that sticks, because it’s tied to real work - not a classroom.

Examples of effective stretch assignments (that actually help people grow)

Here are simple, low-risk ideas that work across most teams and roles:

1. Leading a meeting or project for the first time

Great for practicing communication, structure, and leadership presence.

2. Representing the team in a cross-functional group

Helps people learn influence, collaboration, and big-picture thinking.

3. Solving a recurring problem that no one has addressed yet

A clear way to encourage initiative and problem-solving.

4. Improving a workflow, tool, or small process

Perfect for developing systems thinking and continuous improvement skills.

5. Mentoring or onboarding someone new

A simple way to practice guidance, clarity, and people skills.

6. Taking temporary responsibility during someone’s absence

A safe environment to test new capabilities without long-term pressure.

These assignments create skill-building opportunities at work without formal programs.

How to choose the right stretch for the right person

A stretch should feel like a nudge, not a cliff.

A quick test:

If the person says…

• “This is too easy.” → Not a stretch.

• “This is impossible.” → Too much.

• “This feels challenging, but doable with support.” → Just right.

Aim for 10–20% outside their comfort zone - enough to grow, not enough to panic.

How managers can support people during a stretch

Support is what turns a stretch assignment into positive people development instead of stress.

Here’s what works:

1. Set clear expectations

What does “good” look like? What matters most?

2. Keep check-ins short and regular

These should feel like manager development conversations, not micromanagement.

3. Make it safe to ask for help

Let people know it’s normal to hit roadblocks.

4. Remove small obstacles

Sometimes the barrier is something simple: time, access, approvals, tools.

5. Debrief at the end

Ask:

• What worked?

• What was challenging?

• What would you do differently next time?

Reflection is what turns experience into learning.

Avoid these common mistakes

Even well-intended stretch assignments can go wrong if managers:

• give too much too fast

• overload people with stretch + full workload

• skip support

• use stretch assignments as hidden tests instead of development opportunities

• assign “busy work” instead of meaningful tasks

A stretch should empower - not punish.

Final takeaway

Stretch assignments are one of the easiest, lowest-cost ways to build capability on any team. All you need is:

• a meaningful challenge,

• clear expectations,

• regular support, and

• space to reflect afterward.

Done right, they help people grow through real work, gain confidence, and build skills that matter for the future.

Small stretch. Big impact.

Sources:

(As requested — NOT included in the article body)

• DeRue, D. S., & Wellman, N. (2009). Developing leaders via experience: The role of developmental challenge. Journal of Applied Psychology.

• McCauley, C. D., Ruderman, M. N., Ohlott, P. J., & Morrow, J. E. (1994). Assessing the developmental components of managerial jobs. Journal of Applied Psychology.

• Bjork, R. A. (1994). Desirable difficulties. Metacognition: Knowing about Knowing.

• Kolb, D. A. (1984). Experiential Learning.