Dear Dan: How to Explore Your Boss’s Aspirations
Good morning, Dan!
I had a thought this weekend and wondered what you thought of it.
In my annual mid-year check in/review, my boss and I (and my direct reports) talk about professional development. What we want to do to grow in our careers. I know what my direct reports want, and I tell my manager what my goals are. But something I don’t know is what my manager aspires to be in her career. I want to ask her.
I think it would help me help her. And I would also have a better understanding around her decision making. What are your thoughts on the idea of asking your manager what their ambitions are?
Sincerely,
Boss Booster
AI generated image, 09/02/2024
Good morning, Boss Booster,
What a wonderful thought. Leading up is a unique opportunity. I suggest you explore your boss’s career aspirations. Keep in mind that it may be difficult to get a direct answer.
Most bosses respond with politically correct answers when asked about their career aspirations. “I’m doing my best in this job. If an opportunity arises, I will certainly consider it. I’m content where I am right now.”
I suspect your manager would be uncomfortable telling others she’s looking to advance her career. She doesn’t want to threaten higher ups by saying she wants someone’s job. And she can’t say she’s looking for a job outside your current company. If there’s a current opening it might be easier.
How to explore your boss’s career aspirations:
#1. Focus on present aspirations.
“Hey Boss, I’ve been wondering what your aspirations are for our team.” Follow up with, “What can I do to help?” or “I’d love to contribute anyway I can. Do you have any suggestions?”
You might ease into the conversation by beginning with, “What’s working now?” and moving to, “What could be better?”
Uncover specific behaviors that she thinks would be helpful.
#2. Explore motivations.
Why did your manager pursue her job?
It might go like this. “Hey Boss, I’ve been wondering what your hopes and aspirations were when you took this job.”
Listen to her story. Discern her motivations. Clarify your understanding and offer to support any future aspirations she might have. “How could I better help you achieve your aspirations?”
#3. Reflect on the future by discussing the past.
“Hey Boss, I’m just curious. What are some of your career accomplishments that make you proud?” Be careful not to suggest that there’s something wrong. Follow up with, “What new aspirations or areas have you wondered about exploring?”
Don’t pry if she gives a generic answer.
Tip: Good questions need a soft runway. Begin with, “I’m just curious,” or “You seem to enjoy your role,” or “I’m wondering about ways I can help you achieve your goals.”
Considerations:
- Don’t suggest your manager is dissatisfied with her job.
- Be sensitive to the political situation in your organization.
- Begin with current goals and introduce future aspirations gently.
- Protect her sense of competency. Seek to contribute. Don’t imply she’s needy.
Conclusion:
Your question demonstrates a leadership attitude that’s refreshing. Even if your boss offers a politically correct response, asking the question shows initiative and care. If she avoids the conversation, express your desire to help and let it go.
Your effort will be appreciated, and I admire your thoughtfulness.
Best,
Dan
Author’s note: I suspend my 300-word limit on Dear Dan posts.
What suggestions do you have for Boss Booster?
Further considerations:
How to Coach Your Boss to Success without Losing Your Job
Leading Up: The Art of Managing Your Boss – Knowledge at Wharton
Thank you for asking this question out loud.
I’m guessing it may take several “failed” attempts over a period of time before uncovering insightful nuggets. I’m also guessing that just by asking that question, answers will bubble to the surface down the road as your attention is heightened.
@Boss Booster, I’d love a report on how it goes!
Thanks, Rob. You make an important observation. Success often comes quietly. It takes time, awareness, and gentle persistence.
Maybe try this: “I view part of my job as making your life easier. I’d like to learn a little about what priorities you have both for this unit/team/division and for your own professional growth. That way, I can do a better job of identifying how best to handle certain tasks without having to discuss them in detail with you.”
If they push back on “professional growth”, you can explain that, for example, if they want to work on presentations, then you will defer that work to them. On the other hand, if they really want to step back from presentations, then you will take on more of that work.
Won’t work with a micromanager, of course.
Thanks, Jennifer. It’s interesting you bring up “making your life easier.” It’s an idea that came up during my email exchange with Boss Booster. Love your illustration about presentations. Very practical.