Top Five Reasons to Ask the Question

Sometimes being the boss can feel like pressure to know everything. Asking about what you don't know or fully understand is actually a way to become a better boss.

Photo by Jonny Caspari on Unsplash

There is so much leadership advice out there - you could have a full time job reading and processing it all that would leave you precious little time for actually leading. What it means to be “the boss” shifts depending on the context and situation of leadership, the organization you’re leading and the impact outside events might be having on you, the organization, etc.

But one perennial tension for new leaders is does being the boss mean you should “know best” all the time? Or to put it another way - does asking questions or admitting you don’t understand something you know is important undermine your authority, expose weakness and cause people to lose faith in your leadership? Does it make you less effective or signal you are a pushover who doesn’t know what they’re doing? And I think there’s also a fear of being seen as a “micromanager.” ( I don’t think many people aspire to be micromanagers but on the other hand, be aware that in some cultures, any management might be derisively explained as “micromanagement.” And you do need to manage!)

This is not even a rational fear when you see it written down in print - of course, no leader can know everything, all the time - but it is a very real one.

Of course it makes no sense that an individual is an expert in everything. So then why does it feel so hard to ask a CFO to remind you how “budgeting for depreciation” works, again? Or ask the development director what LYBUNT means, again, when you log in to look at the donor database? Or “is the discount rate the same as net tuition revenue?”

I also think it can be particularly relevant as a new advancement leader when the communications function reports to you. If you’ve been in development your entire career, communications is a different animal and a different subculture. Maybe the communications function is used to being a “service dept” for development, writing and distributing their constituent communications but chances are more recently, the comms folks have been pulled in multiple directions. As the big boss, you may know zero about what the comms director has on his plate to support admissions or to assist the head’s office and yet the communication director is reporting in to you.

So this post is here to advocate: ask the question! Be curious! Use “normie” language that will get your point across. Don’t fake it! And (most of the time) It will help establish a relational dynamic as you get your feet on the ground.

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If you own your authority, asking questions or revealing you don’t “know it all” is letting everyone know you are comfortable exposing a vulnerability - and this shows confidence.