Twelve Questions Great Bosses Ask

I originally published this content in this "What's Up, Doc?" newsletter from the archives, and it retains my copyright. You can find more newsletters at this link on my business home site. Actually, there's a lot of free, "how-to" content for leaders on the site, and there's a search feature as well, on the lower right side of any page. I thought I should share it on the blog since I am so often asked about it.

I recently compiled this list to help a client, and now, all of you benefit! Great bosses get the answers to these questions and remain in close enough contact with their direct reports to know the answers and how they may change. The main point is to create an open, trusting dialogue over time with your direct reports. The value of what you learn through these questions should be obvious, but less obvious is this: by using these questions to create a trusting relationship, any boss is in a much stronger position to make corrections that stick and shape ongoing performance. At the end of the day, your effectiveness as a leader is based on your ability to help people improve performance and learn. Use this question list to guide your efforts.

1. What do you enjoy most in your current work?
As a boss, you’re not obligated to assign only work that your people will enjoy. However, it is to your advantage to know what they enjoy. They will tend to do best what they enjoy most. Peak performance is your friend.

2. What do you enjoy least in your current work?
Again, just because someone may not like a task, it may need to be done. If it’s a core part of the job, then perhaps the person is not best for that job, and should be helped to find another position. If work assignments can be distributed through a team so that people can do what they most enjoy doing without sacrificing overall quality, then you win. Take note of what people dislike doing.

3. Who influenced your career choice, and how?
You should know why and how your people came to make their career choices? By default? Out of genuine interest and passion? You also want to know the best ways to influence your people, so knowing who has influenced them in the past, and how, is to your advantage. But of course, you have a responsibility to use your understanding responsibly, not manipulatively, or against your employees’ interests. Also, before you can help people move forward with their future, you need to know how they got to be where they are today. Understanding history is important.

4. From whom did you learn to become and behave like a professional?
This is another in a series of role model related questions. If you want to have a beneficial influence on your people, for their good and the good of your organization, you have to know what style and type of personal influence works best for each of your best reports. Also, by dealing with your people as professionals, and talking about professionalism, even for jobs that are considered to be of low status, you can inspire your people to think of themselves as “professionals,” and to act accordingly. You can also open up a continuing conversation of what it means to be and act like a professional, making job performance a matter of personal pride. Of course, to talk about this credibly, you had better be consistent and worthy of imitation in your own professional comportment.

5. Who have been your primary role models? What did you really admire about them?
When you learn what your people admire about the most influential people in their lives, you learn about their values. Different traits will come up for different people on your team. When you seek to understand what motivates each of your people, you had best have insight into each person’s unique values systems. A blanket corporate approach to “values” will only go so far. Great bosses motivate their people based in individual understandings of each team member.

6. Who in your life has taught you the most? What was it about that person's communication style that really worked for you?
The first part of the question helps you to establish a connection with your direct employees as people, not just as workers. If you want to be a great boss, your people need to feel you respect and understand them as people, and not just as means to some corporate or organizational end. The second part of the question is key for you if you want to know how best to communicate effectively with each team member.

7. How do you think you learn best?
Most people don’t know how to answer this question, as they have never thought about it. So , you can offer multiple choice answers:

a. Demonstration and observation
b. Personal, independent trial and error
c. Talking, asking questions, hands-on coaching
d. Reading
e. Audio resources such as tapes, CD’s, etc.
f. Traditional classroom training or seminars (this is not likely to be the best option for anyone!)

If your job as the leader is to help your people learn and adapt as your organization grows and adapts, don’t take a one-size-fits-all approach to helping your people learn. And guess what? It’s your job to help your people learn. Great bosses are teachers, or at the very least, they make sure their people have access to the people and resources (sometimes other team members) they need to learn. It’s not primarily the responsibility of someone in a human resources or training department to see that your people are learning: it’s your responsibility as the boss.

8. How can I become more effective in helping your success?
Ask this question a lot. The first time you ask, you may get no response: not many employees really believe there will be no consequences to saying something to the boss that could be interpreted as criticism. Great bosses are more interested in being effective than in appearing to be right. Ask the question, and listen. Everyone knows you’re not perfect, so get the information you need to be better, even when the employee you ask may be difficult or unreasonable. Just asking does not obligate you to agree, but you’ll never learn about your blind spots as a leader if you shut your eyes and ears. Even unreasonable people can see things about authority figures that may need attention.

9. In ideal circumstances, how often should I check in with you just to see how you are doing?
One person’s micromanagement is another person’s support. Find out the preferred mix for each person. On balance, you should use your time as a reward for those who do well, and minimize the degree to which you are always making corrections to your weakest performers. If they are that weak, they are in the wrong job. But still, you should know what the right mix is for each team member’s style, and learn to adapt your style accordingly. Some managers are more active with oversight by nature, and some like to be very hands off. Extreme styles in either direction are problematic, and the best style is to take an individualized approach.

10. What do you feel you do best?
Always give your people a chance to brag to you. They like to have the chance to say what they think they do well. You might learn something you don’t know, and your people will derive intrinsic satisfaction from your implicit act of listening to and recognizing their strengths. Besides, no one will listen to you about areas you think they can improve if they don’t think you understand what they do well.

11. Who is the best "boss" you ever had? What about that person made him/her the best?
It should be obvious why this question is good for great bosses to ask. If another boss has been successful, it’sbest not to have to reinvent the wheel when learning to lead each of your team members. Model your style, as much as you can, based on what you hear.

12. In what ways would you like to grow more?
You can break this out in a few dimensions:

a. Technical skills or certifications?
b. Communication skills?
c. Language skills?
d. Customer service skills or conflict resolution abilities?
e. Learning how to be a better mentor or guide to other team members or new employees?
f. Listen for, but don’t prompt for, a desire to grow in management responsibilities.

Be sure you know what your people want to learn. Compare this with what you would like them to learn. Help them get the learning experiences they need, especially if you can tie extra, rewarding learning experiences with high performance. Extra learning should be a perk you offer to your best people, to reward them, to help your organization grow through its people, and to show weaker performers that the way to get your time and attention is to deserve it through their actions.