Can I Secretly Record a Conversation With My Supervisor?

Q: Can I record my boss without telling him?

A: Voice-activated pens, spy-camera sunglasses, hiding behind the ficus … decisions, decisions.

Hawai‘i is a one-party consent state, so yes, technically you could secretly record a conversation. Some companies, however, have internal policies that forbid surreptitious recording, and employees who work in fields like law, medicine or finance are held to stricter privacy laws. Also be aware that if this is a long-distance phone recording scheme, some states – like California, Delaware and Florida – have two-party consent laws, so every party in the convo has to consent, or the recording is unlawful.

I asked for advice from Honolulu-based David Simons ( He specializes in employment rights and has been practicing law in Hawai‘i since 1978. “As a matter of logistics, recording a conversation has gotten much easier. Thirty years ago, you would have needed a really big purse or a gym bag.” (I’m picturing someone with a giant duffel bag stuffed with a reel-to-reel tape recorder nonchalantly strolling into the conference room.) These days, employees could easily record conversations on a mobile phone, but surprisingly, Simons rarely deals with clients using that as evidence. More often, they provide incriminating texts.

Although it’s legal to record, it’s often not impressive to jurors, explains Simons, using a past trial as an example. “When (the recording) came up, the jury really doesn’t like it; they felt like it is underhanded. The fact that my client had done that was a little offensive. That doesn’t mean it wasn’t effective evidence. But there’s a taint to it.”

Think about your motivation for making your recording. Are you doing it to make the workplace better for you and your employer? Then it’s consistent with being a good employee. Maybe you’ve seen fraud at the company, or need to document sexual harassment, derogatory language or other unacceptable behavior. “If a client is going to be wrongfully terminated, and suspects that during the meeting the employer is going to be candid, having that on tape can be literally worth a lot of money,” Simons says, “but it’s rare.”

When asked by clients, “Should I secretly record?” Simons replies it’s up to them, “but then a lot of times on the recording all I hear is them talking, so it’s not that effective.”

If you’re planning to bust out the spy gear, practice first. Ensure your phone or other recorder is capable of picking up conversation a few feet away. Second, make sure you are comfortable with the technology – you don’t want any wires popping out of your shirt. Awk-ward!

Q: Our new marketing director wants to start an internal newsletter. I’m skeptical. Is this a good use of her time? 

A: I side with her: Having an internal newsletter as part of an overall marketing plan is smart strategy. Like many things in life, corporate newsletters can be well done or be totally lame. (Lame: “Please stop leaving dishes in the kitchenette sink. We are not your mother!”) But having a quality, readable newsletter reinforces company culture and improves employee satisfaction.

Think of the employees as customers for this newsletter: What would they want to read about? Job postings (hello, promotion!) can get their attention. Go behind the scenes at a department, and share what that group does, like a “day in the life” story. This builds greater understanding and collaboration between teams. Or profile a few employees at a time, which is helpful at a larger company or one that is growing quickly (you may never again have to ask questions like, “Who the hell is Debra?!”). Gain insights by doing employee surveys, build excitement with a contest, give shoutouts for personal and professional accomplishments – and of course, weave in some relevant company updates.

Also think about frequency. Is this a monthly email, weekly, quarterly? Decide on a publishing schedule that will be engaging, rather than a burdensome information dump.

A: Everyone says we need to prioritize. But my project due dates often pile up on the same day – usually Mondays. Should I chip away by rotating between projects, every hour on the hour? Or try to finish one thing completely and start another? I get so stressed out thinking about everything I have to do that I don’t even know where to start.

Q: If you’re buried under a heap of work, it is hard to see the light, much less think clearly about your to-do list. For some advice, I turned to my favorite new time-management guru, Laura Vanderkam. She is the author of several time management and productivity books, including “Off the Clock: Feel Less Busy While Getting More Done” and “Juliet’s School of Possibilities,” and has a great podcast called “Before Breakfast” ( She does all this while raising four children, which to me suggests she must have her act together.

“Managing multiple concurrent deadlines is really about managing what happens before those deadlines,” Vanderkam says. “Whenever you get a new project, figure out all the constituent steps. Figure out how long each step will take. Block these into the time before your deadline – and make sure to leave open space.” This buffer acknowledges that sometimes (um, always?) other things come up or projects take longer than we thought.

As for fitting the projects onto your calendar, Vanderkam says, this is more about your work style than anything else. “Some people prefer to devote a whole morning to one project, then maybe tackle two different ones in the afternoon. Others might prefer to switch more frequently.” Studying the time logs of thousands of people, she has found that most of us have more discipline and focus in the morning, so you should probably tackle tougher work then and save afternoons for the easier tasks.

“The most important thing, though, is that you build in enough time for each project in the time before the deadline. Then it doesn’t matter if they’re all due at the same time – you’ve managed the pipeline in the days and weeks beforehand so you’re ready before that day anyway.”

One thing you shouldn’t do, Vanderkam says, is manage stress by checking email. “It’s so tempting, when we feel behind, to try to get on top of our inboxes. We can make progress quickly (look, I deleted 100 emails!), which feels really productive. But it isn’t.” So back away from the email temptation. You’ve got this.


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