Annual Retrospective: 40 Questions for Leadership Teams

To say 2020 has been a challenging year is an understatement, and for many of us, just having acknowledged that we survived will be as much of a retrospective as we need. For others, though, there may still be a desire to earmark some time for some annual reflection. I hope the following questions help to reveal some insights for you and help you to build healthy, happy workplaces in 2021 and beyond.

When things were great

How did you celebrate team members? What kinds of things were team members celebrated for? (For example, was someone celebrated for working over a weekend or for collaborating well with their team?)
How much customer value was shipped in 2020? If the metrics you care about improved this year, how much of it was because of your own effort versus external factors?
How often were compelling and exciting customer success stories shared internally?
How many team members took a nice chunk of time-off in 2020? For those that didn’t take the time off, why?
What actions did you take to create a more inclusive workplace where people can be themselves? What did you do to improve belonging?
In what areas did you and teams improve in 2020?

When things were tough

How did you respond when target dates or goals were missed?
How did you handle situations where there were disagreements? How were people that disagreed with you treated?
Did anyone leave the company this year? How was their departure communicated to staff? How were their responsibilities delegated?
When team members weren’t meeting expectations, how were they told? How soon were they told? How did COVID-19 and other difficulties of 2020 play into those conversations?
How did you and your team communicate about COVID-19 and its impact on our ability to work? More so, how did you match your actions to your words?
When you were given tough feedback, how did you respond? How did you act on that feedback? (If you received little to no constructive feedback, that’s probably a red flag.)
How much effort was “wasted” in 2020? (I’m not referring to prototypes or experimentation.)

When new faces joined

How involved were team members in helping to recruit and hire their incoming peers?
How were new team members greeted when they joined the company?
What kind of assistance or support did they receive during onboarding? How many questions did they ask, and how many of their questions were able to be answered with documentation?
How frequently did you touch base with new folks to see how they were doing?
How quickly were new team members able to be spun up and get into the groove of working?
How did you prioritize adding diverse backgrounds and perspectives to your teams?

When decisions were made

How was decision-making distributed across the company? What level of autonomy did individuals have over their work?
Think back to the most successful decisions and the decisions that failed. Who made which decisions? How was each handled after the fact?
How many decisions were made that you weren’t involved in yourself? (If you were involved in nearly every decision your company made, I’d say you’re working in a low-autonomy environment.)
What decisions were made that you disagreed with? How did you respond?
How are decisions documented and shared?

When people grew and developed

How many people were given promotions or compensation adjustments? What was good and bad about that process?
How many team members grew their skill set this year? How was that recorded and celebrated?
How did you handle professional development? How many team members took advantage of what you offered? If team members didn’t take advantage of it, why?
How often were team members given constructive feedback to help them improve?
How many new leaders emerged in the company this year?
How many times were team members able to share their knowledge with one another? How often did pairing or mobbing take place?

When it came to communication and transparency

How often did you reiterate your company mission, vision, and strategy?
How does everyone’s effort impact the metrics the company cares about? How is this communicated?
How much do teams know about your customers? How much do teams know about company metrics? How accessible is this information?
How many times did team members ask you hard questions and how did you answer?
How many avenues exist for team members to ask questions or give feedback?
What decisions or information did you choose to keep from team members? Why did you not want to share this information with them?
Did you communicate more synchronously (chat, meetings) or asynchronously (documentation, email) this year? Where did you communicate important information?

When it comes to the future

What is your strategy for 2021? How has that been communicated to staff?
Are there any major events or milestones coming in the next year? How have those been communicated and how are you preparing? How will you keep staff informed moving forward?
When your goals or your environment inevitably change next year (because change is the only constant), how do you plan to stay flexible?

Thanks for reading. Let me know what other questions you believe people should consider in their 2020 reflections.