The Leader's Dilemma: 'Can We Really Do This?'

Every leader knows this moment.

You’re reviewing a new project proposal — ambitious, exciting, but clearly beyond the team’s usual rhythm. It demands unfamiliar skills, tighter timelines, new thinking. You can almost sense the unease in the room. Then comes the question — most times unspoken, sometimes explicit — "Can we really do this?"

The same question echoes inside your own head, but sharper: Should I even be asking them to?

Every leader thinks they fear failure. In truth, what they fear is discovering their team’s limits — and by extension, their own. That’s the quiet anxiety behind most leader’s ambition: the tension between aspiration and realism. The leader’s job is to stretch — but not to snap the cord of capability, confidence, or culture.

So how do you know how far to go — especially when you’re a new CEO, a new VP, new Program Lead, or a freshly appointed dean trying to prove that you can deliver transformation?

Leadership often feels like walking a tightrope between pressure and purpose.

You have to set goals that lift people out of their comfort zones but not so high that they freeze. The trick isn’t to know what the goal is — it’s to sense where the team is.

Here’s the paradox: capability isn’t the same as readiness. Most teams have more potential than they use, but less scaffolding than they need. The leader’s job is to fill that gap, by providing clarity, coaching, and belief.

A newly appointed CEO I once coached faced this exact test. Her regional business had missed targets for three consecutive years. Her instinct was to shield the team — to "stabilise first". Instead, she designed a three-month pilot around an audacious new sales initiative. She called it a sandbox: "We’ll experiment freely, fail fast, and measure learnings, not losses." The same team that had resisted stretch targets began generating breakthrough ideas.

This is where real leadership sensing comes in — through four quiet questions that you can use:

• Do they know enough to start? Skills evolve once momentum begins; courage matters more than mastery.

• Do they feel safe to fail? People experiment only when they know failure won’t be punished.

• Do they have the bandwidth? Stretch without slack leads to burnout, not brilliance.

• Have they shown adaptability before? Culture repeats its patterns; curiosity is the best predictor of success.

The data of leadership isn’t on dashboards. It’s in the hesitation in a voice, the silence of someone who once volunteered, the tone of energy after a meeting. Reading those signals is the leader’s most under-rated analytical skill.

Every leader worries. Because worry, at its core, is attention — a signal that something matters deeply. Trouble starts when worry turns into fear. Fear makes leaders micromanage, rescue teams prematurely, or quietly lower expectations.

Ask yourself: What do they need from me so they can do this?

Great leaders don’t stretch people from above — they stretch with them. They remove clutter, reprioritise ruthlessly, and invest visible belief. And they communicate why the stretch matters. That’s where purpose becomes powerful. Purpose isn’t the opposite of pressure — it’s the antidote to it.

When people see how their work connects to something larger — a turnaround, a reinvention, a legacy — they dig deeper. Purpose transforms work from “more effort” to “meaningful effort.” Teams driven by meaning recover faster from setbacks than those driven only by metrics.

This is also where leadership traits show their face most clearly. Leaders who handle this dilemma well display four quiet strengths:

• Courage of Calibration — knowing how far to push, when to pause.

• Empathic Confidence — believing in people without needing to rescue them.

• Curiosity Over Control — treating new projects as learning labs, not audits.

• Conviction in Purpose — linking every stretch to something larger than output.

Every ambitious project carries the risk of failure — and that’s what terrifies most leaders when they push teams beyond their comfort zones. But leadership maturity is about reframing failure itself.

In complex, fast-moving systems, failure isn’t evidence of incompetence — it’s evidence of exploration.  As Thomas Edison said, "I have not failed. I’ve just found 10,000 ways that won’t work."

Like a sandbox, it’s the space where teams test, stumble, and learn what doesn’t work. Each failed iteration is one path eliminated on the way to what will. This "sandbox mindset" transforms the leader’s role. Instead of shielding teams from risk, the leader designs safety around risk. Failure becomes feedback, not a verdict.

Leaders who internalise this approach don’t demand perfection; they design resilience. They turn stretch projects into learning systems, where progress is measured not just in outcomes, but in the sophistication of questions teams learn to ask.

Seven questions before you push your team beyond the familiar.

Stretch without purpose feels like pressure. Make sure the team knows why this matters — what change, turnaround, or impact this stretch will drive.

Don’t wait for perfect readiness. Check for a base level of capability and confidence — then create scaffolds for learning on the go.

Ambition only works if there’s bandwidth. Remove low-value tasks, cut noise, and protect thinking time before adding new demands.

Ensure people can fail intelligently without fear of blame. Reward curiosity, not just correctness.

Ask yourself if this stretch inspires or intimidates. Adjust tone, pace, and milestones so the goal stretches without snapping morale.

Create a sandbox mindset — each failed attempt should reveal what success will require next. Celebrate informed iteration.

Every stretch should grow people, not just numbers. Make reflection part of the project: what did we learn about our limits, and what did we unlock

Leadership is knowing when to push, when to pause, and when to simply hold the mirror steady. The worry you feel before assigning that next stretch target? That’s empathy in disguise. The best leaders don’t suppress that worry; they translate it into care, clarity, and courage.

Because in the end, leadership is not about proving that you can do it all.

It’s about building a world where others believe — and then discover — that they can.

Srinath Sridharan is a corporate adviser & independent director on Corporate Boards. Author of Family and Dhanda.

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