Home IT management Three Questions You Should Ask Every Employee At The Start Of A New Year

Three Questions You Should Ask Every Employee At The Start Of A New Year

Three Questions You Should Ask Every Employee At The Start Of A New Year


The start of a new year often triggers a moment of evaluation. People often ask, “Am I in a better place now than I was twelve months ago? Am I growing? Am I happy?” During these moments, employees often look critically at their work experiences and decide if it is time for a change. As a leader or organization, if you want to keep your best people, it is critical to make time at the beginning of the year to meet with each of your direct reports to understand their goals and map out an employee experience that excites them.

It is important to remember that each of your people is on a journey, and the role they have with you is just a stop along the way. How long they stay with you depends on how much they feel you help them progress and how much the role supports them in living the life they want in and outside of work. When it comes to setting goals, leaders often mistakenly focus the conversation solely around workplace goals or goals for the person’s current role rather than the one they want five years from now. The conversation rarely extends to the person’s life outside of work. In order to support employees in their goals, leaders need to ask about both their work and personal goals, noting that not every person will be interested in sharing them.

Below are three questions you should ask all of your employees to better understand their goals along with a sample email to prepare them for the meeting. It is a good practice to send the questions to your team a few days before the one-to-one meetings so they have time to think about them.

Possible Introduction Email:

Hi Winston,

I look forward to our meeting next week. As this is the start of a new year, I want to use our meeting to understand your personal and professional goals to ensure we are doing what we can to make this a great year for you. Below are three questions that I would love you to reflect on prior to our meeting. Please know there is no pressure to share your personal goals, but if there are ways for me to support you, I am here.




How do you want to grow professionally in the year ahead?

What do you want to learn about? What kind of project do you want to work on? What experiences do you want to have? What skills do you want to develop or improve?

Do you want to acquire a professional certificate, work on your presentation skills, better understand marketing, event organization, or fundraising, take on more responsibility, get promoted, or develop management skills? What would you like to accomplish professionally in the next year?

How do you want to grow personally in the year ahead?

How do you want to grow personally? What experiences do you want to have? What do you want to make happen outside of work?

Do you want to go back to school, travel more, meditate daily, buy a house, improve your comedy, write a book, learn about Bitcoin, or start a side hustle? What do you want to make happen over the next year?

How can the team and I support you in accomplishing your goals?

What can we do to support you?

Do you want more opportunities to present in meetings, more regular feedback, or help to find learning opportunities at work? Do you want people to ask about your goals, not schedule meetings on Thursday after 5 pm so you can attend class, or let you know about networking events? What can we do to support you in the year ahead?

As the person shares, make sure to ask follow-up questions to understand the motivation behind the person’s goal.


Employee: “I would like to get my project management certification this year.”

Leader: “Okay, why is that important to you right now?”

Employee: “I feel like if I ever want to get promoted, I need to have one.”

By asking simple follow-up questions, you get access to some of what drives their goal and are better able to support them.

After you have gotten through all the questions, together, brainstorm simple ways to move forward on each. Once you understand your employees’ goals, they know you understand them as well. Together, you can design a work experience that has them feeling like this is the place to be if they want to grow. If you do, there is a greater likelihood they will have the same meeting next year as they will still be on your team!


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