In the last installment of Moonlighting, we examined the importance of understanding the big picture at work. This week, we’ll consider one method of finding out more about the big picture: asking questions. Not the dumb ones. The good ones. So what are some good questions that can help us to see the bigger picture?

I solicited input from several general counsels, assistant GCs, etc., in different industries and here’s what they came up with. I know, I was surprised they got back to me too. I don’t know whether it had anything to do with the teeny white lie I told them — that they would be compensated for their answers with untold riches and fame — it’s a mystery. But here is what they said…


1. Show me the money. Now, I don’t like to say I told you so, but — oh wait, yes I do. The first response uniformly from all of the bigshot attorneys was: How are we making money? Per issue, contract, and deal — how does the money flow from beginning to end, and what impacts it? What about the company as a whole? I’m not gonna lie and say it won’t bore you to tears, but read the company’s financials and understand the business model. That’s how you learn to put each particular issue in perspective and how much importance to attribute to it. A related question: how are they (the other side) making money?

2. What are people’s incentives? A business person might ride you to finish up a contract because she’s trying to make her individual target numbers for the end of the month. Another might be on you because he’s getting asked about the deal every other day by the CFO. Yet another might just want to take off for his holidays without leaving anything outstanding. Incentives may be a little harder to figure out, but if you can do it, the knowledge will help you to prioritize and find reasonable solutions. Like maybe you tell that last dude so sorry, but he’ll have to keep his BlackBerry on hand while he sips his mai tai by the infinity pool. Life is hard.

3. How does this relate to or impact other matters you’ve worked on? For example, suppose you receive word that there’s been a fire at a company store and people have sustained injuries — they’re threatening to sue. Besides addressing the potential lawsuit issue, consider some related questions: Was inventory affected? Was there property damage? What does your insurance cover and what are the limits? Should you have been more careful waving around that butane torch at that company store this morning?

4. What’s the real risk of a significant problem arising? Be practical. You need to maintain credibility with your business team and that means you don’t flag everything as a major issue if it’s not. Remember the boy who cried wolf? Don’t be that boy. Nobody liked him and or felt sorry for him when he lost the sheep. They probably made offensive shepherd jokes behind the nasty boy’s back.

Learning more about the big picture will help you to prioritize and understand better how the world works. The world being your company of course. (Is there another world?) Are there other questions that have helped you to see the big picture? Email them to me at or comment below.

Susan Moon is an in-house attorney at a travel and hospitality company. Her opinions are her own and not those of her company. Also, the experiences Susan shares may include others’ experiences (many in-house friends insist on offering ideas for the blog). You can reach her at and follow her on Twitter at @SusanMoon.