What do you do if your boss's strategic thinking needs influencing?

One of the most basic fundamental working principle is to be able to understand your Boss / Reporting manager. Her/His aspirations with regards to business /team and self Align yourself along with the Team and Your Boss This automatically demonstrates your Competency

If you believe your boss's strategic thinking needs influencing, approach the situation with tact and respect. Start by understanding their perspectives and the rationale behind their strategic decisions. Prepare well-researched alternatives, presenting them through a constructive lens that aligns with the company’s goals and your boss's priorities. Use data and case studies to support your points, showing tangible benefits or precedents from similar organizations. Opt for private, scheduled discussions to avoid putting them on the spot in public or group settings. Facilitate open dialogue by asking insightful questions that might lead them to reconsider certain aspects without feeling challenged.

The basis of all effective and productive work relationships is trust. Trust is fundamental to enable open and honest discussions, where the listener understands that the conversation is focused on the betterment of the situation. If you boss trusts you, then the suggestions that you make will be received as an effort to improve the performance of the team and/or your boss. It will reduce the resistance to listen to tough feedback.

It's important that you understand how your boss is being measured by the organization, what are the key deliverables, what are his/her pain points in delivering results. This understanding will help you define what will be valuable feedback, what will be actionable and the potential impact of your feedback on his/her overall performance. This understanding will also help you build trust when you provide your boss feedback because he/she will recognize and appreciate your deep understanding of his/her situation.

In my experience, the worst feedback you can provide (or get) is simply stating what you are doing incorrectly. This is often the case in large organizations where you end up with a list of things you are doing incorrectly but without further guidance. If you want to help you boss and build higher levels of trust, make sure that you feedback also includes well defined and specific potential solutions. In my experience, it's best to describe a couple of options and then provide your opinion on the best alternative given the time, resources and other constraints.

Make sure that you understand your audience and that you adjust your communication style to them. In the context of providing feedback, the most important aspect is to be very clear on what the issue is and what the solutions might be. This is because the ultimate goal of the feedback is for your boss to take action, so focus on the actionability of your communication.

The place and time of the feedback is important in all circumstances but it's specially critical when it's managing up. In my experience, the best option is to ask for 1:1 time to define improvement actions. This will create a safe space, will set the tone for the overall conversation, and will enable a more receptive audience.