Winding River Consulting | Blog of Industry Thought Leaders

Are You Really Ready to Lead?

Written by David Toth | Apr 14, 2025

What Nobody Tells New Leaders About Being The Boss

Reaching the proverbial corner office is an achievement few attain. But the reality of leadership at this level is far more complex than most realize. High performers are often promoted quickly, but without formal leadership training. Many new leaders in the accounting profession struggle with delegation, feedback, and conflict because they’ve been taught only how to perform, not how to lead.
Leadership is a constant evolution filled with transformation, reinvention, and at times, isolation. There will be many surprises ahead, but here are some things to be aware of — regardless of whether you’re halfway up the ladder or this is your first rung. 

Making the Transition

In professional service firms, new leaders are often leading people who were very recently just their peers. Rebalancing relationships is a challenge. Don’t overcorrect collegial friendship with newfound authority by becoming too distant or too authoritarian.

You’re Being Watched. Constantly

Your team, peers, referrals, and clients are watching—not just what you say, but how you show up. Your tone in emails, your demeanor under pressure, how you respond to missed deadlines or shifting client demands—it all sends a message. Every action, reaction, and hesitation is observed and interpreted. In firms where leadership credibility is often earned informally, consistency and presence matter deeply. You’re setting the tone, even when you’re not trying to.

You’ll Spend a Lot of Time in Front of People

Leading team meetings, managing client presentations, navigating partner updates—it’s all part of the role. You may be directing conversations that feel more political than technical, more motivational than informative. Over time, you’ll build the muscle to speak with clarity and confidence. Preparation and perspective are key—whether you're talking to one direct report or presenting to the entire firm.



Difficult Conversations Will Become Routine


You will have tough, uncomfortable conversations—a lot of them. Whether it’s giving feedback to a colleague you used to grab lunch with, managing up to a demanding partner, or delivering tough news to a client, these moments are now part of your job. The best leaders don’t avoid these conversations; they enter them with clarity, empathy, and the intent to move things forward.

You Will Be the ‘Bad Guy’ More Than You Expect



Not every decision will be popular. Sometimes, doing what’s right for the team or the firm means making calls that upset people. That doesn’t make you wrong; it makes you responsible. Leadership isn’t about keeping everyone happy—it’s about making informed, fair, and necessary decisions. It’s also about understanding when you share your rationale and knowing when to know that you don’t have to explain yourself.

People Will Tell You What They Think You Want to Hear

Your role as a leader is to create an environment where honesty is valued over approval. Encouraging dissenting opinions and fostering trust will be essential to getting the information you need, not just the feedback that feels good. 

You Need to Build a Team You Trust

At times, you will feel isolated, the weight of responsibility, and the inevitability of scrutiny. The best leaders recognize they can’t do it all—nor should they. The most successful organizations honor a hierarchy of responsibility. Identify those you can rely on, delegate to effectively, and empower to take ownership. Invest in people who are capable and committed.

Develop Others As You Do Yourself

The accounting profession includes unique complexities, like client service pressures, billable hours, and technical excellence. Your growth and that of your teams are interdependent. Coach, develop, and advocate for others. Success isn’t about doing everything yourself; it’s about enabling others to excel. 

You Can’t Please Everyone. So Stop Trying

Your role is to steward the business and its people—not to maintain popularity. Lead with fairness, transparency, and purpose—and accept that some people will still disagree with you. Leadership isn’t a popularity contest; it’s about making the best choices for the organization and the people in it. The sooner you accept this, the more effective you’ll be.

Leadership Is a Journey, Not a Destination

You won’t wake up one day and have it all figured out. Leadership is an ongoing process of growth, adaptation, and learning. The best leaders are those who remain open to change, embrace challenges, and continuously refine their approach. They are continually learning and always growing. Leadership isn’t about having all the answers—it’s about being willing to evolve, even when the path ahead isn’t clear.