Would Your Manager Walk a Mile in Your Moccasins?

Six Ways to Enlighten Your Boss About the Value You Bring Your Company

By Published on .

Traci Armstrong
Traci Armstrong
After the Super Bowl, CBS premiered a new reality show: "Undercover Boss." The show features CEOs of major companies going incognito and working side-by-side with their employees. The first episode followed Larry O'Donnell, the president-chief operating officer of Waste Management, sorting recycling, picking up trash, even emptying portable toilets alongside his employees. O'Donnell learns first-hand how challenging the jobs of his employees are -- so much so, that one of the supervisors actually fires him the first day on the job.

The program reveals the insight and empathy a boss can walk away with after spending time experiencing what his employees do on a daily basis. For example, during his day picking up trash, O'Donnell uncovers the fact that his worker literally has to pee in a can each day because there is not time built into her schedule for a bathroom break. The discovery leaves him mortified, but incited to be an advocate for his employee and create an immediate policy change.

At the end of the show, when the boss reveals he is actually the COO, the employees are deeply touched. They feel appreciated and recognized for their work. The show is sure to strike a chord with the overworked and underpaid of our nation's workforce in this down economy. And the show's message will hopefully be a good reminder to bosses everywhere to stay connected and compassionate while advocating the career progression of their employees.

In a perfect world, all work leaders would make a practice of role-reversal. Unfortunately, most don't have the luxury of delaying their real work to do the work of their employees. As employees, we can all be proactive. If you feel as though your boss is clueless about your day-to-day activities, empower yourself to enlighten her about your routine. Here are some ways:

1. Over-communicate. Despite the fact that my supervisor gets flooded with e-mails, I still make a habit of over-communicating the things I'm working on. I know she may not read everything -- and we cover many of the issues again in phone statuses -- but I like to make sure she at least receives the information. My personal rule of thumb: If the communication is with any of my supervisor's peers or her boss, she gets cc'd on the e-mail.

2. Anticipate and be proactive. Don't wait to be asked. My boss and I formally check in once a week. When we meet, she may have a handful of questions. But I can't expect that she knows all of the activity happening behind the scenes. So typically, I prepare a status list of projects and issues for us to discuss. This saves her the effort while keeping her informed of my workload and challenges. Using this list, she advises me on priorities and provides feedback regarding how to move through any roadblocks.

3. Wear your entrepreneur hat. I owned a small business for many years, so I have a tendency to view things through the lens of, "If this were my business, would I ..." Fill in the blank: Spend this much money? Hire this person? Prioritize this project? This way of thinking allows me to be more solution-oriented rather than simply presenting problems to my boss. I find this helps to inform her without adding to her already heavy workload.

4. Prove your worth in numbers. Establish quantifiable benchmarks with your boss that, in her mind, are evidence you're having success. Only the two of you can determine what those numbers are. Quantifying your benchmark is like the difference in declaring "I'm going to lose weight" or "I'm going to lose 20 pounds." The goal with a specific benchmark is a clear milestone proving success. Once the benchmark metrics are determined, provide results at regular intervals: monthly, quarterly, annually.

5. Provide a "day-in-the-life" inventory. If you're feeling your manager is really out of the loop, take a week to journal each day in 15-minute increments. This will take a lot of extra effort, but will be insightful to both your manager and yourself. A detailed account of the day will highlight things like interruptions and time drains that could be addressed. It can also help rationalize business reasons for assistance or additional resources.

6. Be your own squeaky wheel. I once learned a valuable lesson from a former colleague who happened to specialize in PR: "If you don't toot your own horn, no one else will." Broadcasting your own success can feel awkward for the bashful or humble. However, if done in a way that showcases how your personal success is benefiting the business, leadership may view it as less self-serving and more as a wake-up call to how you impact the bottom line.

As effective as boss role-reversal might be, there may be some situations in which a manager can never really know how it feels to do the job of his employee. I look forward to the upcoming "Undercover Boss" episode in which Hooters CEO Coby Brooks goes stealth in his restaurant chain. The show's producers will have an empathy success story on their hands if they talk Brooks into walking a mile in a Hooter girl's spandex. Unless he's a successful cross-dresser, I'm not sure he'll fully understand what its like for his well-endowed waitresses to be ogled and propositioned by the customers. ("Mr. Brooks, can we please wear shirts that aren't two sizes too small?" "Mr. Brooks, these hot pants make it difficult to pick up spills on the floor.") Hey, a girl can dream.

Traci Armstrong is the director of talent acquisition at Organic. Follow her on Twitter at @tannarmstrong.
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