Challenging Your Boss: Why, When and How You Should

Published: 10 Feb 2014

You haven’t agreed with the recent decisions of someone you work with, but said nothing. You have some great ideas you’d like to share with her, but haven’t. You just don’t feel comfortable speaking your mind.

Why? She’s your boss.

While your hesitation to not “rock the boat” is natural, your silence could create problems. First, you were hired to make valuable contributions to the organisation. If you’re only willing to be a “Yes Person” — and accept the status quo or poor decision-making — you’re neither doing your job well nor helping the company to succeed. Most senior executives are looking for employees to speak up, as lack of new ideas is often a barrier to innovation in their companies.

Also, your unwillingness to articulate concerns or ideas could hinder your career path. Your manager may be looking for you to challenge her on occasion, and you’re not seeing it. And even if it’s true your boss would prefer you go along with every decision she makes, others around you (and above her) may wonder why you always choose to keep quiet. You therefore risk being perceived as someone who lacks leadership qualities and is easily dismissed. 

In summary, silence is not always golden. So, are you ready to speak up? Here’s some advice to help ensure your boss will listen to your feedback and ideas with a positive ear:

  • Preparation builds a stronger case. Don’t just present a list of problems to your boss. Be ready to offer solutions, and explain why those ideas could be better options. An example: “I know we’ve been using XYZ accounting software for years, but I think ABC software could help us work more efficiently. Here’s what my research shows …”
  • Choose your ‘battles.’ While you may be tempted to tell your manager about everything that frustrates you at work, instead centre your conversation on one or two issues you consider important to the organisation and which you may be able to change. Also, avoid setting a negative tone. Instead of starting the conversation with “I don’t like …” or “This has really been bothering me …” try “I would like ...” or “I want to share with you …”
  • Less is more. Effecting change can take time, and depending on the issue, your manager may need to step back and process your comments. Help make it easier by keeping your message simple and to the point. Practice your delivery beforehand and bring along brief notes, if needed, to ensure you make the best use of time.

Trying is everything

Of course, no matter how well you prepare, there’s always a chance your input will not be well received, or acted upon, by your supervisor. But that’s a risk you must take if you want to have an impact at your firm and fulfill the expectations of those who hired you.



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