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Why the Best Entrepreneurs Have Employees Who Disagree With Them

You may have the highest respect for the late Steve Jobs. But would you have ever dared to disagree with him?
Why the Best Entrepreneurs Have Employees Who Disagree With Them
Image credit: Prakasit Khuansuwan | EyeEm | Getty Images
Guest Writer
Freelance writer
5 min read
Opinions expressed by Entrepreneur contributors are their own.

It’s an intuitive fact: To be successful, entrepreneurs must be powerful leaders whose employees immediately fall in line with their every command. When they make a decision, their employees follow almost automatically, and with respect, obedience and trust that their leader is experienced or knowledgeable than they.

Related: How Billionaire Philanthropists Bill and Melinda Gates Settle Disagreements

This does not mean that that leader is necessarily a nice person, however. Consider the number of now-famous entrepreneurs who made a reputation for themselves despite being somewhere on the spectrum between “difficult” and “abrasive.” It's not hard to imagine why these leaders would prefer -- even require -- that they be surrounded with loyal, borderline sycophants. 

In reality, however, businesses tend to perform better when their entrepreneur-founders recruit partners and employees who typically disagree with them, or at the very least willingly voice a dissenting opinion.

Critical thinking and new perspectives

The most obvious benefit of critical thinking is that conflict naturally encourages progress, as described by five-time CEO Margaret Heffernan in a 2012 TED Talk. Disagreements force you as leader to confront the weaknesses of your ideas; otherwise, those weaknesses remain unchecked.

For example, if you lay out a plan for how to market your startup, a dissenting employee might raise concerns about the budget, or point out an issue with how you intend to reach your primary audience. At worst, such dissent forces you to spend extra time on research to reinforce your idea. At best, it alerts you to a critical flaw and prevents you from wasting time, money or energy.

Every person is susceptible to cognitive biases, but those biases tend to be byproducts of our genetics, history and personal beliefs. If you think of biases as blind spots, you can almost guarantee that employees who frequently disagree with you will have different blind spots than you do; in this way, you compensate for one another’s cognitive limitations and can come closer to seeing the full “truth” of a given problem.

Stubbornness and compromise

The stereotypical entrepreneurs are notoriously stubborn. They have a vision for what they want their company or product to be, and they aren’t willing to sacrifice it. Steve Jobs is the go-to example here; he would often demand impossible features to be included in products, or impossible deadlines to achieve some key advantage; and he would frequently lose patience with employees who couldn’t meet those expectations.

This kind of stubbornness, allowed to run rampant, is also a weakness; it may lead businesses to waste time on bad ideas, or to experience disappointment when an impossible goal isn’t met. Having employees who disagree with you allows your stubbornness to be challenged when that's appropriate. And if it turns out that both people are rigid, they can work out a solution favorable to both.

Related: Conflict Among Team Members Can Lead to Better Results

Trust, honesty and resentment

You can practically guarantee that your employees are going to disagree with you, at least on occasion. The real question is whether they’re going to express that disagreement openly and productively, or keep it to themselves. Employees who openly disagree with you trust that their disagreement won’t be met with retaliation; likewise, you, as leader, can trust that these employees won’t withhold their true perspectives.

This open atmosphere makes employees feel more comfortable and respected, and gives entrepreneurs the confidence that their team isn’t just paying them lip service.

Alas, openness isn’t a widespread feature of modern workplaces. Only 58 percent of women and 68 percent of men in a SurveyMonkey study said they believed they could express a dissenting or unpopular opinion at work without any negative consequences. This is unfortunate: Ultimately, it stifles the exchange of ideas in your work environment, and ultimately leads to resentment.

Cultivating an atmosphere for disagreement

The challenge for you as an entrepreneur, then, is creating an environment that allows for constructive disagreements without jeopardizing your leadership or the respect of your employees. You can do this with several strategies:

  • Hire experts and critical thinkers. Not all dissenting opinions are valuable. Try to build a team full of experts, critical thinkers and professionals capable of constructing meaningful counterarguments for dilemmas in their respective fields.
  • Give employees conversational space. Whenever possible, allow the conversational space necessary for employees to voice their opinions. Only the boldest workers will go out of their way to express dissent, but if you go out of your way to ask for individual opinions, employees will be far more likely to share them.
  • Minimize negative consequences. The minute you introduce any kind of retaliation or negative consequence into the conversation, employees will be more wary to introduce their dissenting opinions in the future. Avoid berating, embarrassing or undermining employees who voice their opinions (unless it becomes a counterproductive problem, in which case, consider handling it in private).

Related: Are You Getting Your Money's Worth From Disagreements?

Having employees frequently disagree with you is a sign of a strong organization, so long as you’re cultivating those disagreements constructively. So, learn from the perspectives of your most valuable teammates, even if you don’t change your mind, and embrace the benefits of critical thinking, compromise and trust.

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