New BILL Leader's Counterintuitive Playbook: Slow Down First

By Nathan Brooks

Three months into a new executive role at BILL, a fintech company, one leader is making the case that the boldest first move is refusing to sprint. His argument: speed for its own sake isn't a strategy, and credibility comes faster from admitting what you don't know than from producing instant answers.

The essay, published as an Entrepreneur contributor column, lands at a moment when executive tenures keep shrinking and new leaders face pressure to show a plan in week one. "The first question people ask when you take on a new leadership role is usually some version of 'What's your plan?'" the author writes. "It is a fair question."

His answer, though, is not a plan but a discipline. He calls it learning before leading.

Why the old playbook doesn't travel

Every leader is tempted to bring the playbook that got them promoted. The author's warning is blunt: "Playbooks are a point-in-time representation of how things were done — perhaps in a different company, at a different time."

His frame for practitioners: 2026 is wildly different from even 2025, let alone 2020. Markets move, customer expectations shift, and AI keeps redrawing what teams can accomplish. A playbook written for last year's company is a historical document, not an operating manual.

That doesn't mean discarding experience. It means leveraging past lessons while building for current reality — a distinction he treats as the core job of a new leader's first quarter.

What does this change for incoming executives?

For anyone stepping into a new role, growing a team, or steering through a shifting market, the practical question is what actually earns trust in the first ninety days. The author's answer: clarity about goals, proximity to customers, and candor about gaps — not a list of things to fix on day one.

He structures that around five principles.

1. Question old assumptions — including your own. Past decisions should inform but not determine present choices. The right call a year ago, or even six months ago, may be wrong now. His diagnostic checklist:

• What is working well today?
• Where are customers encountering friction?
• Where do teams duplicate work?
• Which operating assumptions reflect current reality, and which are simply holdovers?

Not every inherited decision is wrong, he cautions. Just don't lean on the past to make go-forward decisions.

2. Diagnose before you decide. Observation before action is a practical operating discipline, not a delay tactic. Finding what's worth keeping matters as much as spotting what's missing. Before any reorganization, he asks: What problem are we solving? What does the organization and the customer actually need? Could technology address it more effectively?

This is where experience pays. He recently instituted a forecasting process at BILL that hadn't existed before. Its absence puzzled him, and his background told him it was critical to the company's future success.

3. Let experts be experts. The leader's job is to build, align and empower a team — not to be the domain expert in every function. The bigger and more complex the role, the more you have to let that go. New leaders earn trust by recognizing expertise already inside the organization and giving functional leaders real ownership.

4. Be candid about what you don't yet know. "Credibility does not require projecting total certainty," he writes. It requires honesty about where you need to learn and a disciplined method for doing so. His own responsibility: bring perspectives together and create the conditions for the team to succeed collectively.

5. Use AI to accelerate your own learning. This is the operational detail practitioners will copy. On arrival at BILL, he received hundreds of documents — board decks, internal materials. Using the company's primary AI tool, he built role-specific resources to help him operate.

"I use AI as a second brain," he writes, describing it as "a second voice that helps me sift through and recall large volumes of information." His concrete use cases: revisiting the history of an initiative, clarifying an acronym, or recalling the strategic rationale behind a decision. "It wasn't difficult," he adds — a useful signal for executives who assume AI tooling requires a technical lift.

The sprint comes later

The author is explicit that deliberation has a shelf life. "You cannot wait forever to make decisions, but speed for speed's sake is not prudent," he writes. The sequence matters: slow down at the beginning so you can sprint later.

His definition of the first weeks reframes the whole exercise. They are "not about proving that you have every answer" but about "creating the conditions for better answers" — getting close to the customer, learning from the people who know the work best, challenging assumptions and being deliberate about where to act.

The closing bet is on pace of learning as the real differentiator. In a market moving this quickly, the most effective leaders will be the ones who learn fast, ask hard questions, and give their teams clarity and confidence to move forward together. For incoming executives weighing a dramatic first move against a disciplined listening tour, the payoff logic is simple: the sprint lands harder when you know which direction to run.