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The Biggest Risk You May Need to Take as a Leader

There is a lot to being a leader. You have a team that’s looking to you for a vision and continual motivation. You have a leader that’s evaluating your performance and the results you inspire. You have customers and projects that are waiting for your time and energy. But you’ve successfully navigated the path to leadership and that demonstrates your ability to take big risks in your career.


Photo: Courtesy of Renwick Brutus

While you’ve managed to build a successful professional path, there will come a time, if it hasn’t come already, when you need to take even bigger risks. These risks may unfold in any number of ways. Sometimes what may appear risky to you may not feel so risky to another. True, the gravity of risks is determined by the taker. But there is one area that we can all agree on to be the biggest risk of all—challenging your leader.

Whether it stems from a disagreement on resource allocation, positioning team members, or implementing new strategies, processes, or products, no two minds will always agree. Yet challenging your leader is a risk. It can result in conflict or worse, termination. But there isn’t anyone who can call themselves a leader who hasn’t found themselves in this position. If not yet, buckle up, it’s coming.

How do you prepare for such a big risk?

There are several things that come to mind based on my years of coaching leaders who’ve had to confront their boss. When you are up against a wall finding yourself facing the lion with its teeth bared, you have two choices: capitulate or confront. If you decide the reward of outcomes is worth the risk, then don’t roll the dice and cross your fingers. Instead, enter in with a plan that will increase your chances for a win-win outcome. Here are a few things you should keep in mind.

Outline The Concerns. Often leaders are unaware of the obstacles they’ve created or how they’ve negatively impacted the corporate culture. It’s daunting to outline concerns to one’s leader, but if they are unaware of their behaviors and the resulting negative impact, they cannot improve. Remind them that you know that they care about the mission of the organization, its success and the ongoing ability to serve its stakeholders.

Enumerate the Costs. Gently remind them what could be lost if things don’t change. The clients will suffer. Employees at large will suffer. And the organization will suffer the cost of lost productivity, higher health care claims, and increased turnover. They may be resistant to this reality, but if you share well-researched proof of possible costs, it could improve the outcomes of your confrontation.

Illustrate With Examples. There should be plenty of examples you can share with your leader that show where you needed to confront someone about something and after doing so, gained improved results. I would hazard to guess your leader has their own stories. Open the dialogue about how gentle confrontation is needed at times and how it’s worked to improve circumstances. Help them see the light through examples of confrontations they’ve successfully led and how you’ve learned by their example.

Talk With Others. Don’t make threats but let them know that you are prepared to speak with the Board of Directors, if necessary, but would hope that as leaders you could design a solution. Share what clients would need to be notified if things were not to improve. If need be, share the talking points you’ve developed from talking to these clients who are also desirous of change. Talking with others beforehand or letting your leader know this will be your next step, is another way to open their minds to the gravity of the situation.

Share Plan B. You never want to enter any negotiation without a Plan B. In other words, if you don’t succeed in persuading change because of your confrontation, you will need to go another path. Sharing your Plan B with your leader may be just the impetus they need to acquiesce. When they see that you will go in another direction—which could include leaving the organization—they may decide it’s time for them to change. Again, this isn’t about making a threat, it’s about discussing the future. What will it look like if your leader will not budge? One way of entering this discussion is to ask them what they would do if they were in your situation?


Renwick Brutus' career has spanned roles as research economist, investment advisor, entrepreneur and consultant. He holds an MBA from Fordham University and has been recognized for his outstanding achievement in sales and business leadership. Today, Renwick applies his unique blend of business strategy and interpersonal skills to help individuals prosper and companies grow. He owns multiple companies and is in great demand to consult with business leaders. Contact him by email and LinkedIn .

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