5 Confrontational Business Situations That Are Opportunities for Choice

Shaun H. Ruff

7 min read

Opinions expressed by Entrepreneur contributors are their own.

Whether you’re just starting on a career path or have climbed to the top rung of the ladder, there are some things in business that will always result in regrettable endings if not tackled head-on. In my personal management style, the solutions I look for in challenges initially derive from integral humane intentions. However, sometimes the best intentions won’t cut it, and difficult decisions have to be made. I’m no stranger to these tough choices and have learned not to hesitate in making them as I rose to the C-Suite and attained Industry authority and thought leadership within-and-for multi-million dollar institutions.

These five important assessments may seem harrowing at first, but on closer examination, they’re largely openings for success:

1) Setting boundaries

It’s important that at the start of your organizational life that you spell out terms of , from agreed hours of work to measured areas of responsibility. But, be on the lookout for an eventuality of hearing the words “team player” as a motivator, not an accolade. Once that misappropriated adjective enters the scene, then all bets are off. You may find that you’ll have to renegotiate your time, conform to reasonable or sometimes unreasonable requests and deadlines, and acclimate to shifting standards. When this happens, you shouldn’t immediately flop defeated and set the bar low. However, you also don’t want to fold and go in the other direction. It is critical to be cognizant of limitations. That is true of life as it is in business.

If you value your time outside of the office, be firm, but know that you cannot be rigid. The current is no means solvent. As invaluable as you think you are, everyone is replaceable. And for better or worse, once you’re promoted to management in a growing , the work you inherit demands more audacious solutions and responsibilities that were once your boss’ worries are now yours. Knowing this will give you a leg up when entering the workforce. Be prepared to lose sometime, but try not to lose it all.

Related: The 8 Characteristics of Healthy Confrontation

2) Besting the boss

Unless you’re running a company or independently employed, you’ll be reporting to someone. Getting to know “that someone’s” personality is key to your success or failure within that organization. Whether you respect or resent that person, you should evaluate your role and weigh potential battles. At some point in your career, you will have to disagree or contest with the person who pays your salary. There’s no happy way to go about this. A calculated, disciplined discussion is one thing, but when passion reveals itself as a driving factor of deviation, hands will rise off the table, and little-to-all formalized compliance will likely go out the window. You don’t want to incite, defy, or criticize your employer publically. Unless you have the support of your boss’s superior or the ear of the organization’s decision maker, thinking of “besting your boss” is a surefire way to be escorted out on your ass. But, if you are thinking about forming a coup and feel successful in your plight, you’re likely at a point in your career where you can find the same success in starting your own company— one that would be a healthy competitor— opposed to expelling decency and ushering a potentially unrecoverable discredit of credence. It’s an idea worth considering.

You may think of your boss as a “tool,” but if that person founded (or significantly grew) the company on lawful means, like it or not, your boss earned some right to its stake. So, when the time arises wherein conflict can’t be avoided, remain focused and steer towards an outcome where both parties can keep their shirts. Be aware that the trajectory won’t always take you there, but try. A career is more valuable than a job. 

Related: 7 Steps for Keeping Conflict Healthy

3) Going to the other side

When you build up your resume and make it to a point where you’re regularly positively interacting with a variety of respected experts in your industry, you’re going to start getting noticed. With proven excellence in your work and actively creating favorable strong impressions, your value is bound to extend visibly beyond the walls of your company. When this happens, it’s certainly flattering to be entertained with options, but your next steps are not going to be without consequence. You might have the best relationship with your employer, but believe me, if you’re a star player and you leave to work for a client, competitor, or affiliate who’s poached you for your talents, trouble may follow. While you might be off to greener pastures by taking the offer, chances are your former employer is not as pleased with this move as you are—and it’s rare that once you leave for the other side, you’ll be taken back. Remember, the relationship may not be severed, but it will be sorely damaged. Be educated when making this kind of decision.

Related: How to Transform Conflict and Gain Respect

4) Walking away from the table

A deal can sound great— often too good to be true. Those deals usually are. But whether it feels wrong from the start or becomes apparent after taking the scenic road to realization, if the fit isn’t quite right, it may never be. Once a deal’s in motion, disengaging without repercussion is one of the trickiest decisions you might have to make. Unless this kind of choice is enacted with mutual interest and no fiduciary implications, the byproduct is likely bad blood. Deal-breaking decisions vary in severity from small-goal setbacks to sinking an entity into the abyss. And be aware that these decisions can often backfire in unrecoverable ways. If you must be the person to end a business relationship, do so with confidence and prepare for imminent consequences. As Charles Bukowski put it: “what matters most is how well you walk through the fire.”

5) Dismissals and firings

Sure, one could argue that the process of layoffs and terminations gets easier, but anyone with a soul can attest it’s never a fun responsibility, especially when the person you’re letting go has an A+ personality. You’re going to feel like you’re the bad guy. And that’s something you’ll have to live with. I’ve had to let go of employees who’ve become good friends over the years. Some of the relationships have upheld, but they’re not the same, and because humanity is dependent on us being emotive sentient beings, we scar. Over time scars naturally, reduce in presence, but they remain. A good and decent boss wants employees to succeed. It’s in the best interest of everyone. It’s in the best interest of the company, too. A good supervisor will try to pinpoint the reasoning for unsatisfactory results from a report and take a spec
ial interest in working with the employee to improve. But if there’s little-to-no improvement and all else fails, you’ll have to pull the rug from the person standing on it. And that’s a fall that always hurts.

Remember that the person you’re letting go breathes the same air as you. Be respectful. Be professional. Be sincere. Find peace with the choice. Don’t justify it. If it had to be done, it had to be done. And, don’t lose sight of being mindful, sympathetic, and kind.

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