9 Self-Assessment Questions Leaders Should Ask Themselves

There is tremendous value in a question. Not necessarily a question to other people – although this obviously has merit – but a question to ourselves. As executive leaders, we have the opportunity to better ourselves and those around us on a daily basis. Let’s take it a step further to say we have the responsibility to do so. That’s because our employees, customers and stakeholders depend on us to live out leadership in significant ways.

John C. Maxwell wrote the book on questions. Literally. In his work, “Good Leaders Ask Great Questions,” John teaches us why questions are so important, what self-assessment questions you should ask yourself as a leader, and what questions you should be asking your team.

The most effective questions aren’t designed to point out the things we don’t know, but rather the things we should be doing to improve ourselves and our leadership capabilities.

Near the end of every year between Christmas and New Year’s, I dive deep into a solitary self-assessment exercise.

I take a look back at the year that is coming to a close and look ahead to the one just a calendar page away. The questions I ask myself are challenging and introspective. They are also highly relevant to any executive experiencing a change in their career path or corporate role.

I challenge you to take some time this quarter to give the following self-assessment questions some serious, focused thought. The first four are meant to be reflective on the seasons in your past, while the final four are geared toward your future. No. 5 is the only question centered on your current situation. Let me know what you come up with – your answers may lead to unprecedented outcomes for both yourself as a leader and your organization as a whole.

1. What have I accomplished?

This is a positive exercise, so let’s start with a positive question. This inquiry should get to the root of what is working in your career. It also gives you an opportunity to reflect. In our executive leadership world, time is often short for these types of moments. So take advantage and dig a little deeper. Instead of focusing 100 percent of your attention on that multimillion-dollar deal you closed, lower the bar to find out what else you achieved. Sometimes the lower-visibility wins are just as important to celebrate.

2. What have I learned?

As much as it pains me to admit, New England Patriots coach Bill Belichick is on to something when he says that he learns more about his team after the season is over than at any point throughout the year. (Full disclosure: I am a diehard Miami Dolphins fan but also root for the Falcons with The John Maxwell Company being based in Atlanta). That’s because having some time to step back from both achievements and failures Is key to holistic understanding. Giving yourself this kind of space can open your eyes to what you truly learned along the way.

3. Who did I lead?

The mark of an influencer is not in the number of followers, but rather in the number of leaders he or she has produced. Think leader replication. We only become the type of leader that people want to follow when we breathe value into their lives. If we want our people to be teachable, hungry, passionate and growth-focused, it’s up to us to make sure that’s who are are recruiting, hiring and on-boarding into our organizations.

4. What held me back?

Chances are you fell short on achieving all of your goals last year, last quarter or even last week. That’s OK. But let’s look closely at what caused these diminished returns. How you answer this question will likely lead to even more questions. Were there things you could have done differently? Did you check out on a certain aspect of your responsibilities that could have make the difference?

5. Do I still love what I do?

#LoveWhatIDo. You’ll find this hashtag plastered across my Twitter feed. Whether I’m delivering a presentation to a crowd of 1,800 leaders in Odessa, Texas, or discussing country transformation with Guatemala’s president and cabinet, I sometimes have to pinch myself. I am absolutely loving this season of my career. But like you, there are certainly parts of the job that I don’t like. The moment these tasks start to outweigh the greater message, I will likely answer, “No,” to this question. Our ability to be effective is directly tied to our ability to be passionate about what we’re doing.

6. Am I willing to pay the price again?

My job requires a lot of travel. A LOT of travel. And with family life hanging in the balance, this question can be one of the most difficult on the list. John says, “Everything worthwhile in life is uphill all the way.” We must figure out if what we’re working for in our careers and leadership development journeys is worth the ascent. For me, I know that my values and goals are in such alignment with The John Maxwell Company that I am willing to pay the price again and again.

7. What are my priorities?

As entrepreneurial, results-driven executive leaders, we are saddled with a dreamer’s mentality, meaning we always have an appetite for more. More change, more revenue and more success. We are easily diverted from the task at hand by the next shiny object or the next big opportunity. The key to overcoming this barrier is by choosing your priorities. It comes down to this: If you have too many priorities, then you have no priorities. Ask yourself this question to identify, assess and ignore these damaging diversions.

8. What habit change will aid me most?

We all know that there are some habits that hinder our progress as intentional leaders. No matter how hard we try to repress them or channel them into positive behaviors, there they are: Traffic and noise to our goals at hand. The first step to overcoming these habits is realizing they exist and being self-aware enough to identify them as impediments.

9. What is my focus word?

Every year, we should all be acting out a “focus word.” Choose a word that defines what you’re hoping to achieve, and then take this word into battle with you every single day. Great words to consider include, “intentional,” “influence” or “collaborate.” Crystallizing and living out powerful words like these will keep you hyper-focused on your mission ahead.

I have guided hundreds of entrepreneurs through these self-assessment questions and along the journey have found that they are worthless without honest, authentic answers. In the end, you are the only one grading this exercise. Those around you, however, are grading your performance as an executive leader.

How will you respond?

Mark Cole is CEO of The John Maxwell Company, EQUIP, The John Maxwell Team and The John Maxwell Leadership Foundation. The enterprise’s fully custom offerings are built on the timeless principles of John C. Maxwell, a #1 New York Times best-selling author, coach and speaker who has sold more than 26 million books in 50 languages.