Tough Talks With Boss Must Be Made

By Lindsey Novak

August 16, 2018 5 min read

Q: I returned to a full-time professional job after working as an independent contractor for the last 20 years. The owner, who has turned out to be a micromanager, and I am not accustomed to working in this type of environment. His micromanaging has made me nervous, and I've been making small mistakes in calculating figures for blueprints. The owner proofs the work and makes snide comments with each error he catches.

I need the job but hate the environment. I don't know how or if I should approach the owner to explain why I have been making mistakes.

A: According to Paul Falcone, author of the bestselling books, "96 Great Interview Questions to Ask Before You Hire," as well as "101 Tough Conversations to Have With Employees," one of the risks small business owners take when hiring individuals who have worked freelance for years is that they may "buck" the system in the beginning from the day-to-day leadership and supervision involved in the new role. "It's difficult getting used to having a boss, much less working closely for and reporting to for sign-off." It's also a risk for the business owners who hire long-term independent consultants as full-time employees. The independent-contractor-turned-employee can be a successful and dedicated employee, but will likely experience unique pitfalls along the way.

For most employees, it's difficult to do one's best work when the boss is looking for mistakes, making snide comments when one is found or otherwise undermining one's self-confidence. Working for a micromanager poses a threat to every working relationship because micromanagers, by definition, are overly controlling. They have a hard time trusting others, so trusting a subordinate's strengths and confidently delegating responsibility doesn't come easily.

Falcone says this new hire has two choices: "(1) Continue in the role without saying anything and without showing any vulnerability to the boss — and plow through this difficult time period, hoping things will work out, or (2) Extend an olive branch to the boss, letting him know you're committed to making this work, but share your concerns about the nature of the current relationship." Express your willingness to make this a long-term successful position where you can contribute to the company's success, but also explain your need for a greater sense of independence in the role. Affirm your desire to earn his recognition and appreciation over time, but tell him you don't perform well when over-managed and that you'd appreciate more freedom to do your best work.

This second choice employs open and honest communication, which some bosses don't accept well (a risk you may need to take to be happy in your job), so the boss could choose to end your employment without much notice, which is allowable under the "at-will employment" concept. It will boil down to whether you can power through this challenge and ultimately gain the business owner's trust over time.

There's risk in either option: The business owner can end your employment for not communicating enough and continuing to make errors, or for communicating too much and making the boss feel uncomfortable. To make the best decision, remove the termination-risk factor from the equation and analyze the two alternatives from a sense of opportunity rather than fear. You must decide what you want your working relationship with your boss to feel like and choose your action plan.

Regardless of your choice, continue your job search, since you never know when the owner may pull the plug on the relationship. Making yourself vulnerable may hasten your demise if the business owner is looking for a reason to terminate you. On the positive side, though, if you want this to work over the long-term, you're going to have to step up and communicate all concerns so respect and trust can enter into the relationship — even if that means guiding your new boss on how to best provide feedback to you.

Candor and frankness, a tough choice for some, always wins if you want a long-term solution; silence and burying your head in the sand works better if you're only concerned about keeping the cash flow over the short term, while focusing your career energies elsewhere. You've got to be willing to have that "tough conversation" to move the relationship in a new direction. And no job is worth having your self-esteem and self-worth attacked daily — no matter how lucrative the pay or appealing the security.

Email career and life coach [email protected] with your workplace questions and experiences. For more information, visit and for past columns, see

Photo credit: at Pixabay

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