You’re facing a tough conversation with your boss. How can you make sure it doesn’t go off the rails?

The goal is important, but for tough conversations, the delivery and words you chose are much more critical. Teeing up the conversation with a comment like "feedback is a gift" or a compliment will make the tough conversation go much easier. Always remember to praise in public and critique in private!

While knowing your goal is important, initially focus on the why more than the how. What do I mean by that? Here is an example to demonstrate the difference. If you start with, "I want to be invited to more of the strategy meetings," then you have shared the how instead of the why. If you say: "I want to be a resource for you when you are working on our business plan for next year. I have a few ideas for developing the skills and I also look forward to your advice." The first version is a demand without explaining your goal. The response may be a yes or no. The second version invites a collaborative discussion. The same goes for your opinion, an apology, etc. Know your why and communicate that at the start.

Focus on making it 'two-way' rather than just what you want to achieve for yourself. Be open to ask how your boss would have expected it or handled if they were in your shoes. Make it truly a conversation so you receive some feedback. Don't dwell much on the 'incident' that's the reason for the conversation, instead emphasize how you plan to handle it better in future to avoid such incidents.

Planning is underrated but success is overrated. He who comes prepared & pre-planned, wins. I believe that the most talented person can be beaten the planned ones. Lemme explain with an example: Wanna win a negotiation, prepare yourself for it. Ask yourself the possible questions that can incurr during the situation QUESTIONS to Keep in Mind before negotiating. ?? Figure out what you exactly want to negotiate for? ??what is negotiable & what isn't? ??what is there for them to loose if this doesn't workout? ??What do you expect to get out of this negotiation? ??How can we both come up with a creative way to get both of us what we want ? ??THE ONE WHO PLANS MORE, WINS

When you have a difficult conversation coming up, it might be helpful to consider the three questions: 1) What do you want to gain from the conversation? 2) What challenges do you perceive in the conversation? 3) What can you do to overcome those challenges? One challenge that can come up are difficult emotions. You might get upset, or feel hurt, or even angry. Practising emotional regulation skills can help you continue the conversation in a healthy and effective way. So before you enter the conversation, consider coming up with a plan for what to do to if these difficult emotions arise. One suggestion is mindfulness. Deep, long breaths or momentary focus on the surroundings can soothe our nervous system.

One dynamic I experienced with a supervisor was where this person was consistently feeling sorry for themself which led to lots of feelings of helplessness, negative self-image, and inaction on behalf of his subordinates. They were very frustrated and challenged him openly at times which only led to increased feelings of inadequacy and negative spirals. Subordinates actively sought to eradicate themselves from his influence. Upon taking the time to listen to this person in detail, this person was dealing with significant depression and anxiety related to a history of witnessed and experienced trauma. After many talks this person was able to connect with a therapist, develop coping skills, and subordinates began to have a better experience.

It is difficult to have any tough conversation, especially with the person you report to. Go into the meeting knowing what has happened, what you can contribute to make happen in the future and the fact that you want to continue to be a valuable team member.

Just like a wife that knows the appropriate right time to get the attention of her husband, so also important for individual to know the mood and appropriate right time to discuss critical issues with their boss. Make your boss to see the positive aspects or reason why your suggestion will benefit the overall well-being of the organization.

Action speaks louder than words. Dwelling on what, why and how of the past incident that led to the present 'conversation' is less productive for both and to the team or org. Instead, focus on an action plan that both would agree to for handling better and avoiding in future. Choose to be a team advocate or mentor to share your own experience to benefit team members and enhance team effectiveness and lessen the burden for your manager.

You should have good understanding of your boss's schedule so that you can approach him/ her at the most appropriate time. You should be able to read the mood and atmosphere so that you can manage what to say and how to say it.

Delicate conversations necessitate a preparatory phase before taking action, with timing being of utmost importance. It's crucial to gauge the right moment, sometimes requiring patient waiting until there's an openness to acceptance and receptiveness from the other person. Observing their energy levels is key. Occasionally, your role is to simply be a sounding board, allowing the person to express themselves freely. Only offer advice or share your opinion when explicitly asked. Guide them towards discovering their own solutions; I've often been surprised by the insights individuals can uncover. Create a supportive space where they can feel okay, even when things aren't okay, recognizing that there might be a lot happening in their life.