The Careerist: I Screwed Up – What Do I Do Next?

Q: I’ve got a great job with a real estate development company, but I’m afraid I’m about to get fired. I screwed up a project, missing a deadline, mixing up job orders and costing the company real money. I’ve done what I can to fix it, and my boss doesn’t know yet. Is there any hope for me or should I pack up and disappear?

A: Slow down, Superman. Let’s look at the facts. Is this an isolated incident, or have your juggling skills failed you all along? Were you flung into orbit without rocket boosters – or colleagues – to get you safely to your destination? Or do you insist on being a one-man spaceship, saving the development world all on your own?

I feel for you, so I turned to David Striph, executive VP of Howard Hughes Corp. and a man who knows a bit about juggling multiple development projects. “Go tell your boss – immediately,” he says. “Don’t hide things. It only makes it worse.”

Mistakes happen – at home, at work and out in the world. It’s how we handle them, and how we prevent them from happening again, that defines us. Striph tells employees what he tells his kids: “’Fess up. Don’t blame anyone else, take responsibility, fix it and move on.” Beating yourself up has the same end result as a pity party – a waste of time and a lot of hyperventilating without any progress or solution.

Before you think all is forgiven, Striph quickly points out the boss will look at your work history, your patterns and how frequently this sort of thing happens. Missing deadlines is usually preventable, so what happened? And how’d you let it get so far without calling in reinforcements? And you’ve got two jobs now: Fix the original mistake as best you can, then identify the root cause and fix that, too.  “You’ve got to show your boss an action plan, with ideas and real, actionable items to prevent it from happening again,” Striph says. In other words, you can’t sweet-talk yourself out of this one. You’ve got to deliver.

If you are smart and lucky, there are potentially some welcome waves at the end of this mistake tsunami. “I remember an employee who walked into my office a couple of years ago and said, ‘I made a mistake,’ ” Striph says. She got the help she needed and fixed the problem, but that’s not what stuck with Striph. “To this day, I know I can trust her,” he says. Earning the boss’ trust is employment gold, worth the walk of shame it takes to get there.

Q: “Help! I’m the manager of a sales team for a local startup and, while we’ve hired what appeared to be a good crop of young recruits to pound the pavement, I feel like I’m herding cats. Their office hours are sporadic at best; they are slow to return emails; and I’m never quite sure what they’re working on. It’s early in the game and their preliminary numbers look promising, but I have no idea how to manage these people!”

A: Oh, those pesky Millennials. Is this how our parents felt when we Baby Boomers started our world-domination tour? Senior writer Lavonne Leong’s February 2015 in-depth report on Millennials in the Hawaii workplace revealed strong opinions among managers around the state, ranging from, “They think they know everything” to “How long is this going to last?” Leong answered that question with a sobering Ernst & Young report predicting that nearly half of the U.S. workforce will be Millennials by 2020. Batten down the hatches – they’re here to stay.

The thing is, they aren’t necessarily slacker know-it-alls as they’ve been portrayed. These guys have rent and school loans to pay, and they are looking to make their way in the world. They just think the 9 to 5, cubicle-style work ethic is the world of Mad Men’s Don Draper, not the ideal for today’s workplace.

Who’s to say they’re wrong?

MacGregor Greenlee is the GM of the successful Breakout Waikiki, an escape room catering to groups who love solving puzzles to free themselves from themed, locked rooms in under 60 minutes. He relies on a staff of 18 – all under age 28 – to keep his doors open, his TripAdvisor reviews sparkling and his money rolling in.

He opened Breakout about a year ago, and much of his core staff has been with him from Day One – a respectable retention rate for anyone, but particularly for the lower-wage entertainment business. A Millennial himself (27 years old), Greenlee’s thoughts offer guidance. “Millennials want to be part of something,” he says, “a community where they can contribute and where they understand ‘why’ you do what you do.” He relies on apps to communicate with his staff, using GroupMe to alert and engage them about work news and “shenanigans” (team-building events) and the When I Work app for their shift scheduling and other administrative tasks. “Their phones are always at the ready,” he says, “And it saves me a lot of time and administrative energy by letting the apps do the work.”

As for the shenanigans, these team events are central to his management strategy. He says holding creative events like Waikiki scavenger hunts keeps them engaged. “They have to work through different puzzles in teams, much like our customers do,” he says. They compete for prizes, but, more important, the pride of beating their colleagues. “We work, and we stress sometimes. Then we sweat and have fun.”

Greenlee’s strategy is more than a fad to engage Millennials with a short attention span. He knows their enthusiasm rubs off on customers, who come back again and again. “Over half of our customers are repeat visitors,” he points out, “and our TripAdvisor reviews routinely mention the enthusiasm of our staff.”

As for engaging your sales team, Greenlee says, he believes Millennials don’t simply take a job for the paycheck – they want to be able to personalize the job to reflect who they are and want to feel like they are part of something. Maybe it’s time to give up on cat herding and try a management style that engages them in their native environment, including communication tools to build community, results-driven work incentives that highlight their successes (not just their work hours), and a strategy that gets them excited about the business and vested in the outcome.

Consider the upside. These guys think email is something formal, from the dark ages, akin to handwritten notes in blue or black ink. Since estimates say most of us spend around 30 percent of our days managing emails, imagine our collective productivity if we could cut that in half?

Have a question about work, life and that place in the middle where it all gets tangled up? Ask me at:

Categories: Careers, The Careerist