7 Principles for Leading When It’s Hard


I was confidently rolling through my day when I got an email intended for someone else. It was a strongly worded message criticizing my leadership, sent by a colleague who felt they’d been poorly treated.

Seeing that felt like a punch in the stomach. And the discussion that followed was really hard. But, like many hard things, it prompted a productive conversation that restored our relationship.

Leadership is much easier when you’re confidently rolling through your day, leading from your strengths and motivation. It’s a lot harder when you’re outside your comfort zone. In fact, it can be pretty painful and dark.

Maybe leadership is hard for you right now.

Jon Eisele has had his share of hard days. For over 30 years, he has been a Managing and Advisory Partner for Deloitte and a member of Deloitte’s Global Audit Executive Committee. I recently caught up with him to talk about the hard parts of leadership, and from responses, I learned seven specific instructions on how to lead with resilience and effectiveness. Here’s a recap of that conversation.

What was a deeply challenging time in your career and how did you grow through it?

Jon: Becoming a managing partner at a young age was intimidating because I had to manage people older than me. Shortly after my promotion, we lost our two biggest clients. It was a massive blow to the business, and it was under my leadership. I doubted my abilities. At the same time, I believed that I had earned the right to be in the position, and I continued to communicate my vision for the future to our company.

You mentioned your self-doubt. How have you managed unhealthy influences over your leadership effectiveness?

Timidity has held me back, especially in the early part of my career. I was reluctant to take risks, especially the daily risks to take a stand and interject my ideas in meetings. I learned to intentionally plan to speak up and be heard. On my way to a meeting, for example, I would decide that I was going to contribute to the dialogue, and I’d remind myself why that would be important.

Thank you for being open about your struggles. What role has emotional transparency and vulnerability played in your leadership? I’d imagine that audit practices, like the one you’ve been in, may foster a more guarded approach to leadership.

Vulnerability works best in one-on-one conversations. Leaders need to make time for emotionally transparent dialogue in personal settings where you can maximize trust and listening. A prominent Division I head football coach recently demonstrated this well after a game during which a player was hurt. Despite the player’s pain, the coach was adamant about the player staying in the game. After the game, the medical staff confirmed that the player had sustained a more serious injury than the coach had expected. He immediately went to find the player in the locker room. The player assumed that the coach was going to give him more criticism for not playing through the pain. But he didn’t. He reversed course and gave a sincere apology, admitting he’d done the wrong thing. Quickly admitting your mistakes is central to effective leadership.

What hard things have you learned to say “no” to, or who have you learned to disappoint to be a more effective leader?

I could take this question a few different ways but here’s one way I think about it: Once we had a very high-potential staff member who we discovered had lied on their resume during the hiring process. Several colleagues recommended that we look past it. The employee apologized and was, after all, a top performer. I wish I could have let it go, but I knew we had to take a stand for total integrity in our firm. I made the decision to terminate the individual’s employment. This disappointed some people, but it showed that I do what I say, and it was a marking moment in the firm’s culture.

What leadership attributes have you had to work hard to develop in yourself, and how have you done it?

Listening. I’m impatient and too often assume I know what you’re going to say or ask before you finish talking. I think this will save me time, but it costs me time and trust. I’ve really worked on staying present with people as they finish communicating their ideas. This has been significant in building trust and resilience in my leadership.

Leading and being human can be messy and painful. What lessons have you learned through the hard times of leadership?

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