How to Prepare for Your First Month in a New Leadership Role

By Randall Kaplan

A new leadership role can create a powerful urge to prove ourselves immediately. We arrive with ideas, experience, and a title that gives our decisions more weight. It is tempting to start changing things before anyone can wonder whether we deserve the opportunity.

But the team has a history we haven’t lived. A process that looks inefficient may protect an important customer commitment. A quiet employee may have an excellent idea that previous leaders repeatedly dismissed. A problem described as urgent may be a symptom of something nobody has explained yet.

Our first month should help us understand those realities while establishing that we’ll act on what matters. We can create momentum without pretending we already know the whole story.

The Assignment Behind the Title

Before making promises to the team, we need clarity with the person who hired or promoted us. Why was this role created or reopened? What needs to improve? What authority comes with the responsibility?

We should also understand existing commitments. A delivery date, customer promise, or personnel decision may already constrain what we can change. Discovering those commitments early prevents us from making conflicting ones.

A useful opening conversation can distinguish immediate obligations from longer-term ambitions. If everything is described as equally urgent, we need help establishing priorities. Leadership begins with choices, and our own manager should understand the choices we’re preparing to make.

The Same Questions Across Different Perspectives

Early conversations become more useful when we ask several people about the same underlying issue. We might ask what repeatedly slows the team down, which work customers value most, and what a new leader should understand before changing anything.

We’re listening for both agreement and differences. If sales describes delivery as unresponsive and delivery describes sales promises as unrealistic, we’ve found a relationship to understand. We haven’t yet found someone to blame.

Our notes should preserve examples. “Communication needs improvement” tells us little. A description of a customer handoff with missing information gives us something to investigate.

Extreme Preparation® means pursuing enough detail to make our first decisions informed. It also means noticing whose perspective we haven’t heard.

The Work We Need to See

Conversations alone may not show how the work actually happens. Where appropriate, we can observe a handoff, review a recent project, or ask someone to walk us through a recurring task.

For example, an approval process may look straightforward in a diagram. Watching a real request move through it may reveal that nobody knows who can approve an exception. The delay lives in that unanswered question.

We should explain why we’re observing. People may reasonably worry that a new leader is evaluating them before understanding their work. Curiosity expressed with respect helps us learn more accurately.

Our first responsibility is to distinguish what we’ve directly observed from what we’ve been told and what we’re assuming. Those are different levels of understanding.

One Early Improvement With a Clear Purpose

An early improvement can build confidence when it addresses a real obstacle and stays within our authority. It should solve something people recognize rather than exist mainly to display our arrival.

Perhaps the team needs one clear owner for incoming requests. Perhaps a recurring meeting needs a decision-maker present. We can discuss the proposed change with those affected, identify what success would look like, and agree to review it.

The scale matters. A small change that reduces confusion can establish trust. A sweeping reorganization before we understand the team can create new problems faster than we can diagnose them.

We also need to explain what we’re still learning. Thoughtful uncertainty can make our judgment more credible when it is paired with a clear next step.

What We Want the Team to Know About Us

By the end of the first month, people should have evidence of how we lead. Do we listen closely? Do we keep commitments? Do we explain decisions? Can someone bring us bad news without first polishing it into something reassuring?

A coach can help us review the signals we’re sending and rehearse difficult conversations before they become defining moments for the team. That work can reveal whether our urgency is helping people focus or making them afraid to ask questions.

Our first month does not need to prove that we have every answer. It should establish that we’ll learn carefully, decide responsibly, and follow through. Those habits give the team a reason to trust the direction we take next.

About Randall Kaplan

Randall Kaplan is a serial entrepreneur, investor, and executive coach. He’s a co-founder of Akamai Technologies and the founder and CEO of JUMP Investors, which has invested in more than 100 early-to-late-stage companies, including Google, Seagate, and Lyft. For 25 years, he’s coached hundreds of entrepreneurs, business owners, and executives. He created Extreme Preparation® to help people pursue their boldest ambitions, overcome the obstacles standing in their way, and change the course of their careers, businesses, and lives.

He also interviews some of the world’s most successful people, including Mark Cuban, Tony Robbins, Mike Tyson, David Solomon, and David Rubenstein, on his podcast In Search of Excellence, which has reached as high as #3 in Entrepreneurship and #10 in Business on Apple Podcasts.

Learn more about executive coaching with Randall.