What to Ask the Person in the Mirror

There comes a point in your career when the best way to figure out how you’re doing is to step back and ask yourself a few questions. Having all the answers is less important than knowing what to ask.

by Robert S. Kaplan

If you’re like most successful leaders, you were, in the early stages of your career, given plenty of guidance and support. You were closely monitored, coached, and mentored. But as you moved up the ladder, the sources of honest and useful feedback became fewer, and after a certain point, you were pretty much on your own. Now, your boss—if you have one—is no longer giving much consideration to your day-to-day actions. By the time any mistakes come to light, it’s probably too late to fix them—or your boss’s perceptions of you. And by the time your management missteps negatively affect your business results, it’s usually too late to make corrections that will get you back on course.

No matter how talented and successful you are, you will make mistakes. You will develop bad habits. The world will change subtly, without your even noticing, and behaviors that once worked will be rendered ineffective. Over a 22-year career at Goldman Sachs, I had the opportunity to run various businesses and to work with or coach numerous business leaders. I chaired the firm’s senior leadership training efforts and cochaired its partnership committee, which focused on reviews, promotions, and development of managing directors. Through this experience and subsequent interviews with a large number of executives in a broad range of industries, I have observed that even outstanding leaders invariably struggle through stretches of their careers where they get off track for some period of time.

It’s hard to see it when you’re in the midst of it; changes in the environment, competitors, or even personal circumstances can quietly guide you off your game. I have learned that a key characteristic of highly successful leaders is not that they figure out how to always stay on course, but that they develop techniques to help them recognize a deteriorating situation and get back on track as quickly as possible. In my experience, the best way to do that is to step back regularly, say every three to six months (and certainly whenever things feel as though they aren’t going well), and honestly ask yourself some questions about how you’re doing and what you may need to do differently. As simple as this process sounds, people are often shocked by their own answers to basic management and leadership questions.

One manager in a large financial services company who had been passed over for promotion told me he was quite surprised by his year-end performance review, which highlighted several management issues that had not been previously brought to his attention. His boss read several comments from the review that faulted him for poor communication, failure to effectively articulate a strategy for the business, and a tendency to isolate himself from his team. He believed that the review was unfair. After 15 years at the company, he began to feel confused and misunderstood and wondered whether he still had a future there. He decided to seek feedback directly from five of his key contributors and longtime collaborators. In one-on-one meetings, he asked them for blunt feedback and advice. He was shocked to hear that they were highly critical of several of his recent actions, were confused about the direction he wanted to take the business, and felt he no longer valued their input. Their feedback helped him see that he had been so immersed in the day-to-day business that he had failed to step back and think about what he was doing. This was a serious wake-up call. He immediately took steps to change his behavior and address these issues. His review the following year was dramatically better, he was finally promoted, and his business’s performance improved. The manager was lucky to have received this feedback in time to get his career back on track, although he regretted that he had waited for a negative review to ask basic questions about his leadership activities. He promised himself he would not make that mistake again.

In this article, I outline seven types of questions that leaders should ask themselves on some periodic basis. I am not suggesting that there is a “right” answer to any of them or that they all will resonate with a given executive at any point in time. I am suggesting that successful executives can regularly improve their performance and preempt serious business problems by stepping back and taking the time to ask themselves certain key questions.