Ten Tips for Initiating Difficult Conversations With Your Manager: A Caring, Professional Approach

Working with a boss with different work styles can be challenging. In the best of circumstances, the manager – employee relationship is a symbiotic business relationship of resources or input, output or production, and feedback. The employee provides satisfactory output or production to make the manager look good. The manager provides the necessary intrinsic and extrinsic motivational factors to sustain and/or improve output. In the worst scenarios, an autocratic or micro-managing style can cause emotional pain for the employee or team and disrupt this symbiotic relationship.

In regards to voluntary terminations, research indicates most people leave their managers not the company. Thus, organizations generally support and encourage managers to effectively lead their teams and create the best environment to meet business outcomes. Unfortunately, not all managers are exemplary managers in regards to building relationships through setting expectations, open and effective communication, collaboration, timely feedback, rewards, recognition, and managing team dynamics. In some instances, communication styles, personality preferences and leadership styles may interfere with the manager-employee relationship to the point that output decreases, employee engagement suffers, and voluntary turnover ensues.

Depending on the economic situation and the job market, it may not be easy to just leave and try to find other employment. For many individuals, staying actively employed is a necessity and thus, the employee must balance job satisfaction and the financial needs of employment. So what you can you do if you work with a manager whose style is different than your own? How can you approach the situation in a caring, thoughtful, logical manner that can potentially become a win-win for you, the manager and thus, the organization? How can you initiate a constructive and compassionate dialogue with your manager?

1) Patiently suspend judgment. Our culture is grounded on labeling individuals to categorize and use these categories to approach individuals and manage situations. Jumping to conclusions through categorization may prevent you from learning more and making the best decision and approach possible.

2) Calm the inner voice that wants to be decisive based on emotions. The person may have hurt you feelings or has done something from preventing your needs being met, but do take a quiet moment to calm the voice to help you process your next steps.

3) Gather facts and information to gain a broader perspective. What was happening before or during the difficult interaction? Is this the first time the interaction happened? If not, does there appear to be associated factors that stimulate the response? Does the manager treat everyone on the team in the same manner? What do you know, not think or believe, inspires the manager to succeed and thus engage the team to support the success?

4) Review your emotions. Ask yourself what is bothering you the most about the manager’s actions. Write them down. Ask yourself if you think the person knows they are hurting your feelings or not meeting your needs. Ask yourself “do I know for sure if the person realizes they are hurting my feelings or making it difficult for me to do my job by…” If the answer is “no”, then consider verifying your concerns.

5) Put yourself in your manager’s shoes. Consider the business, the team, the objectives and goals. What would it be like to be the manager for a day? This activity is not to justify actions but to gain a broader and deeper perspective.

6) Determine what differences there appear to be between you and the manager and assess if there is something that can be learned or gained from the differences.

7) Prepare to address the differences or “needs” in a meaningful, non-confrontational, non-threatening conversation and dialogue.

8) Depending on the circumstance, decide if you will discuss immediately after the next interaction occurs or schedule an appointment to specifically share your concerns. If at all possible, try not to share your concerns in front of others. It is always best to take the high road and preserve the manager’s dignity by discussing privately, especially if you are feeling reactive. You are trying to create a collaborative session, not an adversarial moment.

9) Regardless of the outcome, thank the manager for allowing you an opportunity to share your concerns.

10) Document the conversation for future reference.

If the actions and behaviors continue and you are not able to work effectively, then perhaps then it may be necessary to seek other employment. If the actions begin to reflect bullying or workplace violence behaviors, then share your concerns with your organization’s human resources department.