My boss asked me to do what? How to handle worrying work requests

Too often, employees are put in a quandary when asked to do something that makes them uncomfortable, with no right or wrong answer. Here's how to respond in those situations.

Consider this scenario: An IT worker—let's call her Amy—is asked by her manager to destroy data on a particular server in the office. The manager—let’s call him Todd—tells Amy the data must be destroyed because it’s potentially vulnerable to a data breach. But Amy is worried that the destruction of certain data may be illegal and that following through on Todd’s order might put her in a compromising position. She raises her concerns with Todd. He tells her it’s standard IT practice and to get on with the task.

The dilemma is one many workers face every day, in many forms. You believe you’re doing good works in your job, but then you, a lowly IT worker, are asked to do something you deem questionable. There are dozens of examples, tech-related and otherwise. Such a request might include the destruction of sensitive data, illegal hiring and termination practices, the use of pirated software, or an undisclosed security breach that you’re told to keep quiet. Sadly, it’s probably easy to think of more items to add to the list.

How do you respond? Such requests in the workplace are nothing new, but the issue has particular resonance with the IT community. Research shows that IT is the most popular industry for independent workers, including consultants, gig workers, and independent contractors. These workers tend to move from project to project at various companies, and they generally don’t enjoy the same legal rights, benefits, or protections as full-time employees. In addition, because IT supports every department, its staff often touches data and processes across the organization, providing a window into others’ behavior. For example, security professionals can see what data is gathered in other departments.

However, pushing back against a project for such reasons is unlikely to endear you to your managers. The actions you take are fraught with danger. Here's how to navigate questionable situations.

Use your gut

Requests that make you pause generally fall into two broad categories, and those categories suggest the appropriate tactics for an employee (or contractor) to adopt, says Lynn Taylor, a national workplace expert and author of Tame Your Terrible Office Tyrant: How to Manage Childish Boss Behavior and Thrive in Your Job. When the act is clearly illegal, such as the destruction of data, “never comply,” Taylor says. “No job is worth permanently damaging your reputation and future career options.” Involvement in something illegal can follow you throughout your career, and of course it can have serious legal consequences.

If a manager or employer asks you to do something that falls into a gray area—that is, you think it may be questionable or possibly illegal—gather all the information you can. Think carefully about all the potential outcomes and options before you agree, Taylor cautions.

“Use your gut,” Taylor adds. “Step back for a minute and ask yourself if what’s being asked of you feels right. That’s a big litmus test.”

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It’s also worth asking yourself if the conundrum you face is an imbalance between your personal choices and your employer’s policies. You might see problems where others do not, says Stephen M. Byars, an associate professor of clinical business communication at the University of Southern California’s Marshall School of Business in Los Angeles. If you feel you can’t fulfill the request from your superiors, and you feel bold enough to make a stand, there are a number of options you can try.

Speak up

If your manager asks you to do something that makes you uncomfortable, the best thing to do is ask lots of questions, says Taylor. Tell the manager you want to understand the request more clearly. Ask to hear the request again, and then paraphrase it, using your own words. Next, ask what the company’s motivation is for the request, and whether there are any alternative approaches.

If you detect that your manager might be open to discussing alternative approaches, try explaining your concerns for your own career and the company as a whole, says Byars.

Stress that you want to be helpful and that you value your job, Byars suggests, but that you wonder if there may be another path for you to help a particular project. If you’re lucky, you can be transferred to another division or project; in that case, you can still support the company but not have to violate your own moral code, he says.

The language you use is important, notes Taylor. Avoid accusations or criticism. Instead, ask for clarity on the company’s objective. As you hear about the problem in greater depth, you might get ideas that could help the company or make your boss’s job easier. You might also learn that your initial read on the situation was mistaken.

It’s always possible your boss hasn’t thought through the fallout. “Sometimes managers get caught up with pleasing their own boss,” Taylor says. “They just want to get the job done,” which can mean turning a blind eye to the downside risk.

What if your manager doesn’t help? You can try speaking with their supervisor. Or you could discuss your misgivings with a manager in the company’s HR department.

However, this approach is not without risk, says Byars. “No one likes being passed over, and so this approach can come with complications that are harmful to one’s career,” he says.

Build your case

If you want to change your manager’s mind, the most convincing arguments are those backed up with data and clearly reasoned, notes Jose Godinez, an expert in business practices and an assistant professor at the University of Massachusetts. 

Build a “stakeholder analysis,” clearly documenting who or what will be impacted by the action. Show how that will come to pass, in both financial and non-financial impact, Godinez suggests.

Then go back to your manager to demonstrate the possibility of a detrimental affect on the company. For example, accepting a client that runs a gambling site and has a reputation for aggressively targeting vulnerable customers may lead to reputational damage or negative press reports. That may lead to the loss of top-performing employees, threatening the company’s ability to capture high-profile clients.

“Usually, managers respond more to the financial consequences you highlight,” Godinez says. “They are usually focused on the company’s bottom line, and not the less tangible consequences, so state the pros and cons clearly.”

He adds, “With the data clearly articulated, you can have a meaningful discussion with your supervisor. Otherwise, the discussion becomes a debate about positions and feelings, as opposed to quantifiable evidence. If you can quantify the consequences, you have a better argument.” 

There’s another reason to collect data: It serves as evidence that you did your best to prevent a corporate debacle. 

For instance, if you discover the company is engaging in what you perceive to be insurance fraud and you tell the boss about the problem but they override your written warnings, at least you have documented your efforts. That may not save your job (though it may be evidence in a wrongful termination lawsuit), but it might save your reputation if the business goes ahead with the behavior, particularly if you feel moved to report it.

Start your job search

If your entreaties fall on deaf ears, you might want to start looking for your next job. You may feel you’ve lost respect for your employer because the company even considered such a breach of proper behavior. Taylor says, “It doesn’t speak well of the company you work for and its moral compass.” You might conclude this request is the tip of the iceberg.

Without trust and commitment, your efforts at work are likely to suffer. You may also think your company’s long-term prospects are bleak, and question whether you really want to invest more of your time working for that employer.

“Ultimately, you need to ask if the employer is one you want to be associated with,” says Byars. “However, in a tight economy, you might not have that luxury.”

Byars adds, “Companies are not democracies. They proclaim that they respect individuals and their views, but I don’t think that’s always the case.” Sometimes the only option is to separate from the company that puts you in an uncomfortable position, he notes, and you might be wiser when you choose your next employer.

Do what’s right

Self-protection in the workplace is paramount, Byars says.

“There is behavior we wouldn’t engage in if completely autonomous, but when we are working together, there is great subconscious pressure to conform to the standards of the group,” he says. “All of us are prone to this behavior at work, and the tech industry is no exception.”

So, for example, if the boss champions a new company policy, there’s a great deal of pressure to fall into line and subscribe to it. We might have private reservations, Byars points out, but we don’t speak up if the consequences might be fatal to our careers.

Longer term, consider finding a work mentor, someone you can confide in and from whom to get advice when questionable situations arise, Byars adds.

In the end, this is your career. The choices you make follow you forever, so consider your options wisely, says Taylor.

“There will always be short cuts and quick bucks, and there will always be companies that look to take the easy route,” Taylor says. “Global competition has never been more intense. There will be more and more of these issues in the future.”

Workplace dilemmas: Lessons for leaders

  • When an act is clearly illegal, never comply. No job is worth permanently damaging your reputation and future career options.
  • Ask lots of questions; ask to hear a request again, and then paraphrase it, using your own words, so it’s clear that you understood it.
  • Arguments that are backed up with data and clearly reasoned are likely to be the most convincing.
  • Sometimes the best option is to brush up your resume and find a job where you aren’t asked to comply with wrong-headed policies.

This article/content was written by the individual writer identified and does not necessarily reflect the view of Hewlett Packard Enterprise Company.

This article/content was written by the individual writer identified and does not necessarily reflect the view of Hewlett Packard Enterprise Company.