My Biggest Work Fail: A Lesson for Millennials and Their Managers

My first job out of college was in the business development group of at the height of dot-com mania. Early on, I was tasked with negotiating a contract with a new client, something I’d never done before. But I was on it – referring to my notes and busily cutting and pasting verbiage.

When I was finished, the contract reflected everything we had discussed – I had nailed it! But as I like to say, you don’t know what you don’t know. And there was something critical I didn’t know: The customized contract was supposed to be redlined so the team could track what was changed from the original.

Oops. And not a little oops — a huge one. The lawyers on both sides went ballistic, and our firm spent a lot of time and money fixing the mistake.

Was it my mistake? Of course, and I owned it. But in some ways, it wasn’t. How could I have known the process if I had never negotiated a contract before? In hindsight, my manager probably should have walked me through a model. But I also should have asked for one, because if I had seen a sample I would have gotten it. That’s why a collaborative environment is key to success on both sides.

Millennials, You’re Not Being Pests When You Ask Questions

When you’re new to a job, or just taking on a new task, it’s great to be eager, but you’re not a mind reader. You have to ask the right questions before you can take the right action.

It’s also incredibly important to always clarify. When your manager says, “Call Ellen”, that probably means pick up the phone, not send an email or a text. But if you’re unsure, ask. Just refrain from asking every time. Chances are good that if you’re supposed to call Ellen, you should also call Evan.

Managers, You’re Not Being Micromanagers When You Offer Guidance

You don’t want to hover, but you have to remember new employees don’t have the institutional knowledge and experience you have. That means there’s a burden on you to make sure there’s some model or best practices information available to help them tackle new tasks.

Don’t fret that you’re being inflexible or not challenging your employees to figure something out themselves. Offering guidelines can make everything smoother right up front, especially in a multi-generational workplace. Millennials don’t know how things have always been done, and they don’t necessarily understand your references.

What Time Is ‘Early’?

I was talking to a law firm partner who mentioned a misunderstanding where he asked an associate to be in the office early the following day so they could prep for a client meeting. To the partner, “early” meant 7 a.m. But to the associate it was 9 a.m. The partner was fuming, and the associate was mystified.

We no longer speak a common language in the workplace, so managers need to be specific, and millennials need to ask. So if a manager asks you to come in early, just ask what time she wants to get rolling so you have a clear picture of her definition of early. (And then I recommend you come in 10 minutes before that.) It never hurts to clarify instructions, on either side.

What to Do When You Mess Up

Even with all this clarification, sometimes we all make mistakes. Here are three ways to put yours behind you.

  • Apologize immediately and sincerely. But only do it once. Over-apologizing just brings increased attention to the mistake.
  • Own it. Don’t just approach your manager and lay out the problem; come prepared to offer solutions — ideally several of them. In my situation with the contract, I offered to start from scratch or pay for the changes. I ended up starting from scratch, but I also “paid” in that I had to participate in the ensuing uncomfortable phone calls with the angry lawyers.
  • Don’t mess up again for a very long time. Make sure you completely understand what you’re supposed to be doing and take extra care in your work so you don’t become known for making mistakes.

Readers, what has been your biggest fail, either as a manager or new employee? I’d love to hear in the comments!

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Lindsey is a globally recognized career and workplace expert and the leading voice on generational diversity. She has spoken for more than 300 audiences including Google, Goldman Sachs, Estee Lauder, Stanford and Wharton. Lindsey is the author of four career and workplace advice books, and her insights have appeared in media outlets including The TODAY Show, CNBC, NPR, the Harvard Business Review and the Wall Street Journal.


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