Most companies still treat development like something that happens after the real work—courses, workshops, certifications, and leadership offsites.  All of these have their place and can be extremely beneficial if carried out and  applied correctly.

But in a volatile market, your edge isn’t how much your people know. It’s how quickly they can figure out what to do when they don’t know what to do—and how reliably they can do it without breaking the business.

That capability has a name: learning agility. Korn Ferry describes it as a top predictor of success—“knowing what to do when you don’t know what to do.” (Korn Ferry) And they also warn that skills gaps are not a “nice-to-fix HR issue,” but a business threat: Korn Ferry reports that many CEOs see employee skill gaps as a direct risk to performance. (Korn Ferry)

So the conversation needs to shift from training to strategic agility.

And the fastest, most scalable way to build that agility is surprisingly simple:

Make first-time work a classroom.

Why “wait until you’re ready” is broken

The old model assumes that competence comes first, and then you earn the right to take on bigger work.

Today, the reverse is true. The market changes faster than readiness can be “granted.” Products, tools, regulations, customer expectations, and competitors move continuously. The winners aren’t the organizations with the most training hours—they’re the ones that can learn in motion.

That’s why “first-time work” matters. When someone takes on a project they’ve never done before, they’re forced to:

• make decisions without a script,
• navigate ambiguity,
• build judgment (not just knowledge),
• and learn how to learn under pressure.

But here’s the catch: experience alone is not the teacher. Evaluated experience is.

So first-time work becomes a true classroom only when you surround it with structure—feedback, reflection, and a safe place to practice before the stakes are high.

1) Stretch assignments are the real leadership curriculum

Most leadership growth doesn’t come from formal programs. It comes from hard assignments that require a leader to stretch.

The Center for Creative Leadership (CCL) popularized this in the 70–20–10 framework: leaders tend to develop most from challenging experiences and assignments (70%), then relationships (20%), and only a small portion from coursework (10%). (CCL)

CCL’s research goes further: across studies of executive development, challenging assignments make up the largest share of key developmental experiences—nearly half. (CCL Innovation)

In business terms: your best “leadership program” is often the work already on your roadmap—if you assign it deliberately.

Examples of high-value first-time work

• First time leading a cross-functional launch
• First time owning a budget or P&L slice
• First time handling an executive escalation
• First time negotiating a strategic partner agreement
• First time presenting a high-stakes narrative to customers or the board

The goal isn’t “sink or swim.” The goal is stretch with support.

2) Standardize the debrief: turn experience into reusable learning

If you only “do the project” and move on, you leave most of the learning on the table.

Debriefs are a force multiplier. A widely cited meta-analysis found that properly conducted debriefs can improve individual and team performance by roughly 20% to 25%. (PubMed)

One of the most practical models comes from the U.S. Army’s After-Action Review (AAR). Army training doctrine describes an AAR sequence that includes reviewing what was supposed to happen, what did happen, what was right or wrong, and how to perform to standard next time. (First Army)

For business teams, you can translate this into four clean questions:

1. What did we intend to happen?
2. What actually happened?
3. Why was there a gap?
4. What will we do the same or differently next time?

Two notes that make debriefs work in the real world:

• Keep them close to the event (within days, not months).
• Focus on decisions, signals, and process—not blame.

3) Build a psychological safety sandbox—because fear kills learning

If errors are punished, experimentation stops. And without experimentation, first-time work becomes trauma, not training.

Google’s research on team effectiveness (Project Aristotle) concluded that psychological safety—people feeling safe to take interpersonal risks like asking questions or admitting mistakes—was the most important dynamic in effective teams. (Rework)

Amy Edmondson’s foundational research defines psychological safety as a shared belief that the team is safe for interpersonal risk taking, and links it to learning behaviors in teams. (Massachusetts Institute of Technology)

For leaders, this isn’t about lowering standards. It’s about creating the right environment for learning fast:

• high standards,
• clear guardrails,
• and low shame.

Business translation: create sandboxes
Sandboxes are controlled environments where the cost of failure is low but the learning is high:

• simulations and role plays (customer calls, negotiations, escalations),
• pilot phases (limited rollout before scale),
• “dry runs” for key presentations,
• and “pre-mortems” to surface risks early.

A pre-mortem, introduced by Gary Klein, asks a team to assume the project failed—and then generate plausible reasons why—so risks can be addressed while they’re still cheap. (tashfeen.pbworks.com)

This is how you “welcome errors” responsibly: not in production, but in practice environments designed for learning.

4) Make reflection a requirement, not a nice-to-have

Debriefs are the team loop. Reflection is the individual loop.

In a well-known Harvard Business School field study, workers who spent the last 15 minutes of the day writing and reflecting on what they learned performed 22.8% better on a final test than those who didn’t reflect (even though the non-reflection group spent more time working). (Harvard Business School Library)

This is a big deal for business because it’s low-cost and scalable:

• 10–15 minutes,
• consistent cadence,
• simple prompts.

A reflection prompt that works

• What did I learn today that I didn’t know yesterday?
• What would I do differently if I replayed today?
• What’s the one principle I want to carry into the next attempt?

Reflection turns first-time work from “I survived it” into “I extracted value from it.”

5) Measure the right thing: time-to-competence beats training hours

Most organizations still measure development by inputs:

• hours in training,
• modules completed,
• certifications earned.

Those are activity measures—not capability measures.

If first-time work is your classroom, your scoreboard should be about how quickly people become effective in new territory.

Two metrics bring this into business language:

Metric 1: First-time outcomes

“How good was the 1.0?”

Examples:

• quality on first pass (rework required),
• customer impact / satisfaction,
• cycle time vs. plan,
• number of escalations or defects,
• stakeholder confidence rating.

Metric 2: Time-to-competence

“How fast did a leader move from novice to proficient?”

Examples:

• week when they can run the work without rescue,
• % of decisions handled independently by week 4/6/26,
• manager/peer capability rating (simple 1–5),
• self-rated confidence paired with observable outcomes.

This also aligns with what transfer-of-training research has emphasized for decades: learning “sticks” when the work environment supports application—especially through opportunity to use the skill and reinforcement on the job. (Gwern)

A practical operating system for first-time work

If you want to install this as a repeatable business practice (not a motivational poster), here’s a simple rhythm:

1. Pick the first-time on purpose (1–2 per leader per quarter)
2. Define “good” before they start (success criteria + guardrails + escalation rules)
3. Sandbox the hardest moments (role play, pilot, rehearsal, pre-mortem) (tashfeen.pbworks.com)
4. Run tight feedback loops (10-minute check-ins after key moments)
5. Debrief with the same four questions every time (First Army)
6. Require brief reflection to lock learning in (Harvard Business School Library)
7. Track first-time outcomes and time-to-competence (and review them like performance metrics)

The bottom line

Don’t protect your best talent from unfamiliar work.

Design unfamiliar work so the struggle becomes the strategy. First-time work—surrounded by sandboxes, debriefs, and reflection—builds the one capability every organization needs right now: strategic agility.

And when the next “unknown” hits (it will), you won’t be asking, “Are we trained?”
You’ll be able to say, “We know how to learn fast.”

References

• Korn Ferry on learning agility (“knowing what to do when you don’t know what to do”). (Korn Ferry)
• Korn Ferry on skills gaps as a business threat. (Korn Ferry)
• Center for Creative Leadership (70–20–10 framework; development from challenging assignments). (CCL)
• CCL paper on challenging assignments as the largest share of key developmental experiences. (CCL Innovation)
• Google re:Work (Project Aristotle) on psychological safety as top team dynamic. (Rework)
• Edmondson (1999) on psychological safety and learning behavior in teams. (Massachusetts Institute of Technology)
• U.S. Army FM 7-0 Appendix K on After-Action Reviews. (First Army)
• Tannenbaum & Cerasoli meta-analysis on debriefs improving performance ~20–25%. (PubMed)
• HBS Working Knowledge on 15 minutes of reflection improving performance (22.8%). (Harvard Business School Library)
• Gary Klein on project pre-mortems. (tashfeen.pbworks.com)
• Baldwin & Ford (1988) review on transfer of training and the role of work environment support. (Gwern)