9 Year-End Reflection Questions for Company Leadership

The end of the year is a natural time to take stock of what's happened over the past twelve months in our personal lives and to set resolutions and goals for the new year. But I also like to encourage business leaders to go through the same exercise, to reflect honestly on what went well for themselves and the organization—and also what didn’t. Executives (and individuals!) often like to leave the past in the rearview mirror, but the exercise of looking back is often what most helps us look forward. Doing so ensures the organization is headed in the right direction, and that you, as a leader, are performing as your most successful self.

Here, then, are nine year-end questions for leaders to consider as they reflect on the past twelve months:

 1. Did I accomplish my professional goals? If not, what stopped me?

One of the first and most important questions we can ask ourselves is if we achieved what we wanted to achieve. If you did, how would you rate your performance and the results of reaching each goal? If you failed to meet any of them, what were the reasons for this failure? This helps us improve our goal setting for next year by making more realistic assumptions and timeframes for achievement.

2. Am I satisfied with how I spent my time this year?

I don't know of many executives who don't wish for more hours in a day. Your role as a leader or executive likely means that you're looking at the big picture, analyzing trends, and determining ways to set the course for your organization's success. Did you allow yourself the time to plan, create, and inspire this year? Or did you get mired in the details of day-to-day operations?  Looking back, where do you wish you'd spent more time this past year? Identify the things you should be doing but aren't, and eliminate or delegate tasks that take you away from the work that best adds value to your organization. Think about ways you can devote more time to this area going forward by evaluating how you manage your time, as well as the tools and people around you that can help you get there. Once you have your priorities for the year, don't forget to continually refresh and refocus these priorities as the year progresses to make sure you're devoting your time where it's needed most.

3. Did I take time to focus on special projects or new ideas for the company?

 As tempting as it is for an organization to simply stay the course or make modest strides year after year, true success comes from a willingness to innovate and try something new. Your company relies on you as a leader to blaze this trail of innovation. Did you dedicate a portion of your time this past year to special projects and new ideas? If so, were those projects and new ideas successful, or were they abandoned due to constraints on time or resources? If a project or idea failed, what did you learn from that?

4. Did I keep my commitments (i.e., meetings, events)?

Keeping promises and commitments is essential for any leader to build and maintain trust with employees, customers, and other stakeholders—and it sets a tone for others in the organization to do the same. How did you rate this year on keeping your commitments? If there are commitments you had trouble keeping, consider whether these commitments are truly important to you and your organization. If so, are there systems you could put in place to help keep you more accountable? If you're not keeping commitments because you don't view them as important, perhaps it's time to eliminate or delegate them going forward.

5. What am I proud that I accomplished this year?

While it's good to look back on the last year with a critical eye, don't forget to acknowledge those projects or initiatives that went well. Think about how this success was achieved: Are there strategies you employed that could help you reach future goals? Or was your success achieved only through sacrificing huge quantities of time and resources (and possibly your sanity!)? However you met your goals this past year, take a moment to give yourself a pat on the back—and then reflect on how you would or would not do it differently if you could go back in time.

6. In What Area(s) Did I drop the ball?

If there's not at least one area where you didn't feel like you dropped the ball this past year, congratulations! You are a rare leader indeed. But for most, I suspect, there's probably at least one nagging, uncomfortable area that you know you could have done better. What's yours? Being honest about where you're not performing to your best ability can help you assess where you might need some assistance, and prevent a repeat disappointment next year.

7. Can I change or remove one recurring appointment on my calendar?

A recurring appointment can seem like a good idea when you set it up—it both reserves the time on your calendar and ensures that you're checking in on a person or project regularly. But recurring meetings can often mean wasted time if there's no new information to report or decisions to be made. Is there a recurring appointment on your calendar that could be removed or changed? Could someone else attend in your place? Scrutinizing each recurring appointment on your calendar and considering its value could result in some much-needed time for you.

8. Did I give enough time to my direct reports?

A leader's time and attention to direct reports can often mean the difference between a well-oiled organization and a failed one. But between more demanding responsibilities and travel, an executive can often lose touch with those most in a position to help him or her. Did you give enough time to your direct reports this year? Think about the mode and frequency of communication you provide to your direct reports each week. Is your team engaged? Are they on the same page as you? Do they have what they need from you in order to succeed?   

9. Can a Chief of Staff help me be more productive in 2017?

If you've found yourself struggling with time management, prioritization, keeping commitments, or attention to direct reports this past year, it may be time to consider some help. Is a Chief of Staff the answer? A professional partner who anticipates your greatest needs and acts on them, a Chief of Staff may be just the person you need to help you focus on your company's growth, profitability, and overall success.   

So here's to looking ahead to a satisfying and successful 2017. May where you have been and what you have learned in 2016 bring you a clearer direction about where you're headed in the new year. And if you think a Chief of Staff might enhance your success in the year ahead, please don't hesitate to contact me. I am happy to chat with you further to determine if a Chief of Staff is right for you and your company.