Opinions expressed by Entrepreneur contributors are their own.
Key Takeaways
- Your playbook got you here, but it was written for a different company in a different year.
- The fastest way to earn trust in a new role is to admit what you don’t know and show how you plan to learn it.
- Slow down at the start so you can sprint later — speed for its own sake isn’t a strategy.u003cbru003e
The first question people ask when you take on a new leadership role is usually some version of “What’s your plan?”
It is a fair question. When you are new, there is a natural temptation to prove your value by showing up with quick answers, or a list of things you plan to fix. I have found that there is a better place to start.
I’m early on in my role at BILL. The questions I keep coming back to in these first three months are how do I want my first days, weeks and months to look. Where should I spend my time and why? How do I strip away noise and “get to signal” quickly? How do I create proximity to the customers and to teams without slowing down the organization’s work? These are things an entrepreneur is faced with every day, whether they are stepping into a new role, growing a team or navigating a changing market.
Every leader is tempted to bring their playbook. In my opinion, playbooks are a point-in-time representation of how things were done — perhaps in a different company, at a different time. 2026 is wildly different from even 2025, let alone 2020. We have to leverage the lessons from our past while building for the future, backed by modern technologies and customer expectations.
In a new role, credibility comes from being clear about what you want to accomplish and getting in the trenches. It comes from learning the business, understanding people’s day-to-day, and the customer pains that help inform a go-forward plan. Your job is to listen to the people closest to the customer and the work, identify the obstacles preventing them from moving faster, and empower them.
I believe it’s important to reconsider the possible, but change for the sake of change isn’t helpful. With AI evolving as quickly as it is, there’s more at stake. AI is reshaping what teams can accomplish, and markets and customer expectations can change quickly. The way I think about it is: How do we prioritize, sequence and bring the organization along on the journey?
Here are five principles I am using to learn before I lead:
1. Question old assumptions, and test your own.
Past decisions should inform but not determine present choices. The decisions that were right a year ago, or even six months ago, may not be right now. The mindset should be: What is working well today? Where are customers encountering friction? Where do teams duplicate work? Which assumptions about the way we operate are based on current reality and which ones are simply holdovers?
That doesn’t mean every decision made before you arrived is wrong, just don’t rely on the past to make go-forward decisions.
2. Diagnose before you decide.
As a practical operating discipline, observation before action is essential. Finding what’s worth keeping is just as important as finding out what’s missing or needs to evolve. A new process or organizational change may ultimately be necessary, but assess the need first. Ask: What problem are we trying to solve? What does the organization and the customer actually need? And could technology help us address it more effectively? This is one place where experience really can count. I recently instituted a forecasting process that didn’t exist before. Its absence puzzled me, and experience told me it was critical to the company’s future success.
3. Let experts be experts
Your role is to build, align and empower a team, not be the domain expert in every area. In the past, I have had jobs where I needed domain expertise, but the bigger and more complex a leadership role becomes, the more you have to let that go. A new leader earns trust by recognizing the expertise already inside the organization and making it clear that functional leaders have real ownership.
4. Be candid about what you don’t yet know.
Credibility does not require projecting total certainty. It requires being honest about where you need to learn and showing that you have a disciplined way to do so. In a role this broad, that means building and aligning the team while empowering the people closest to each domain to lead with their expertise.
My responsibility is to bring those perspectives together, help the team work toward its best and create the conditions for us to succeed collectively.
I use AI as a second brain. As I was starting at BILL, I received hundreds of documents, including board decks and internal materials. Leveraging them, I used our primary AI tool to build role-specific resources to help me operate. It wasn’t difficult, and I now use AI as a second voice that helps me sift through and recall large volumes of information. It’s something that you can use to strategize and validate alongside. There’s a lot to remember, and AI can really be a friend in that regard. I can use it to quickly revisit the history of an initiative, clarify an acronym or remind myself of the strategic rationale behind a decision.
Key takeaway
The first weeks in a new role are not about proving that you have every answer. They are 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.
You cannot wait forever to make decisions, but speed for speed’s sake is not prudent, so slow down a bit at the beginning before you start to sprint. In a market moving as quickly as this one, the leaders who will be most effective are the ones who learn fast, ask hard questions and give their teams the clarity and confidence to move forward together.
Key Takeaways
- Your playbook got you here, but it was written for a different company in a different year.
- The fastest way to earn trust in a new role is to admit what you don’t know and show how you plan to learn it.
- Slow down at the start so you can sprint later — speed for its own sake isn’t a strategy.u003cbru003e
The first question people ask when you take on a new leadership role is usually some version of “What’s your plan?”
It is a fair question. When you are new, there is a natural temptation to prove your value by showing up with quick answers, or a list of things you plan to fix. I have found that there is a better place to start.
I’m early on in my role at BILL. The questions I keep coming back to in these first three months are how do I want my first days, weeks and months to look. Where should I spend my time and why? How do I strip away noise and “get to signal” quickly? How do I create proximity to the customers and to teams without slowing down the organization’s work? These are things an entrepreneur is faced with every day, whether they are stepping into a new role, growing a team or navigating a changing market.