Persistence with Purpose: The Value of the Second Ask

The first “no” is often not the final answer – sometimes it’s just the most reflexive.

Introduction

More than twenty years ago, I stopped into a neighborhood kitchen store. I picked out a $15 gift and brought it to the counter, asking if it could be wrapped. The clerk politely explained store policy: “We don’t wrap items under $20. I paused and asked, “Ok, could you wrap it anyway?” Without hesitation, she said, “Sure.”

That brief exchange has stayed with me ever since because it revealed something fundamental about persistence. The first “no” is often not the final answer – sometimes it’s just the most reflexive. Asking again, with patience and respect, may not always change the outcome, but what is certain – surrendering to the first “no” guarantees it won’t.

Over time, I’ve realized that this small moment captures something essential about leading complex nonprofit capital projects. Whether you’re building affordable housing, restoring a neighborhood landmark, or opening a community center, the path from vision to reality is filled with many “no’s.” Each one tests your patience, your strategy, and your ability to ask again – this time, better prepared.

Understanding the Forces Behind Resistance

Nonprofit leaders often assume that City officials and other partners will eagerly embrace projects that align with public goals – transforming blight, promoting equity, and strengthening neighborhoods, for example. But bureaucracy operates under different pressures. Most well-meaning public servants juggle dozens of mission-aligned projects at once, constrained by process, workload, and risk, not by indifference. Understanding that helps reduce frustration.

Still, respecting the system doesn’t mean accepting inertia. It means understanding why it moves the way it does – and learning how to work within, and occasionally around, that rhythm. The leaders who succeed are those who treat bureaucratic obstacles not as personal affronts, but as puzzles to be solved patiently and with perseverance.

The leaders who succeed are those who treat bureaucratic obstacles not as personal affronts, but as puzzles to be solved patiently and with perseverance.

Know When to Push and When to Step Back

Calvin Coolidge said: “Nothing in this world can take the place of persistence… Persistence and determination alone are omnipotent.” Capital projects inevitably bring moments when essential partners – government agencies, lenders, or community groups – say “no.” Some of those moments are worth challenging; others are not. The art of leadership lies in knowing the difference.

A thoughtful executive pauses to ask: Is this “no” blocking the mission, or just my preferred route to it? Sometimes a firm “no” is valuable data – it clarifies limits or exposes another path. Other times, it’s an invitation to reframe the question. Every “no” contains the seed of a potential “yes.”

I’ve learned – sometimes the hard way – that persistence is most effective when it’s guided by strategy, not by stubbornness. It’s not about pushing harder – it’s about pushing smarter. Progress often comes not from force, but from preparation: asking smarter questions, understanding the reasoning behind decisions, and finding allies who can make the case from new angles.

The following practices can help translate patient persistence into forward motion:

Step back when insisting would cost more goodwill than it gains.
Push where change is possible without upsetting precedent. Save climbing mountains for later.
Persistence works best when it’s informed. Before returning after a “no,” take time to understand why the answer was given. Was it law, policy, budget, timing, or misunderstanding?
Acknowledging valid constraints by demonstrating that you understand the other side’s limits turns a negotiation into a partnership.
Start by asking quietly curious questions: “Can you help me understand what drove that decision?” “Is this a policy, or more of a guideline?” “Would it make a difference if certain conditions changed?
Do your research. Review policies and precedents. See whether similar projects received exceptions.
Judgment comes with experience and counsel. Seek perspective from people who know the terrain: former agency staff, experienced nonprofit peers, board members with civic relationships, or consultants who understand public processes. Advisors who understand municipal systems or banking protocols can help determine when escalation is worthwhile and when patience will yield more.
Enlist respected outside voices – people with credibility but no direct stake in the outcome – to help make the case on your behalf.
Informed persistence isn’t about wearing people down. It’s about returning to the conversation better prepared, with empathy for the other person’s constraints and clarity about your own. That’s when the second conversation sounds – and feels – very different from the first.
Framing an idea as a pilot helps decision-makers move past the constraints of precedent and process, giving them room to experiment without feeling bound to a lasting commitment.
Look for alignment between your request and the decision-maker’s goal – showing how your proposal helps them achieve their mission.
Strategic waiting can be powerful; stepping back to let new leadership, policies, or circumstances evolve may open the very door that persistence could not.
When progress stalls at a staff level, respectfully seek a higher-level conversation without creating defensiveness. Acknowledge the individual’s effort and authority, and frame the request as a way to confirm alignment or explore options beyond their control. The goal is collaboration, not escalation.
Keep relationships warm between asks with periodic check-ins or updates – without an immediate request. This signals respect and genuine collaboration.

Manage Yourself as Much as You Manage the Project

Perhaps the most overlooked aspect of a capital project that is encountering obstacles is the toll it takes on the leader. Balancing budgets, donor expectations, construction timelines, and staff morale, while running a nonprofit, can stretch even the most capable executive. Strong leaders cultivate perspective. They separate what they can control from what they can’t. They recognize when frustration stems from fatigue rather than fact.

Capital projects test endurance as much as expertise. The ability to stay steady through months of uncertainty – neither surrendering to delay nor pressing so hard that relationships fracture – is what distinguishes resilient leaders from exhausted ones.

Patience is not passivity. It’s disciplined persistence – the willingness to keep working the problem from new angles, knowing that progress often happens quietly, behind the scenes, long before anyone notices.

Capital projects are marathons. They test stamina, judgment, and emotional steadiness. Executives who enter them with realistic expectations, strategic patience, and informed persistence not only improve their odds of success – they grow as leaders in the process.

The emotional and bureaucratic complexities of these projects aren’t distractions from the work; they are the work. They reveal how systems function, how partnerships form, and how leadership matures.

With preparation, humility, humor, and persistence – the kind Coolidge celebrated – nonprofit leaders can turn the grind of capital development into something transformative: not just new buildings, but stronger organizations and wiser, steadier leaders.

And it all begins, sometimes, with something as simple as asking again: “Could you wrap it anyway?”

Ready to take the next step? We’d love to chat with you!

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