Dear Rebecca,

I’m a 31-year-old tax accountant, working at a mid-sized regional firm. My wife and I just had our first child after trying for three years. We’re very excited, but now I’m in a bind.

My wife and I agreed during her pregnancy that we would only use daycare as a last resort. It’s expensive and inconvenient, plus we really want to be the primary caregivers for our daughter. My wife worked it out with her boss that she works at the office on Mondays and Wednesdays and stays at home with the baby the rest of the week. Her parents are willing to watch the baby on Mondays...which leaves Wednesdays.

My wife and I have agreed that I need to ask my boss if I can work a flexible schedule, e.g. four ten or eleven hour days, so I can be at home on Wednesdays. BUT...I’m terrified to talk to him. I’m afraid he’ll see it as a sign of weakness. He’s a real guy’s guy - cigars, cognac, late dinners, etc. Work is the center of his life, and it seems like the team picks up on these behaviors. Any advice?

- A New Father

Dear New Father,

Welcome to parenthood!

As I read your question, I wondered, “Does that agreement that you entered into with your wife during the excitement of pregnancy still hold for you?” If not, then you need to talk with your wife and family first. Simply tell them that you’re worried that your boss isn’t going to respond to your request, and see if there are other options you can brainstorm together.

If it still comes down to the need to ask your boss for Wednesdays off, I recommend looking around the firm and seeing if there are other high potential employees or leaders who work a compressed workweek. If so, you may want to talk with them about how they positioned their alternative work situation.

Then, prepare for your meeting with your boss and position Wednesdays off as a one-month pilot - for him and for you - to see how it will go. Be clear that you’re going to work all your hours...but you’re going to do it during four days, not five. And make sure he knows that if this isn’t working for him or the firm, you’ll renegotiate after 30 days.

Let me know how it goes!

Have a question for Rebecca? Email her: rr@nextgenerationconsulting.com.