The 5 Critical Conversations to Have With Your New Boss

five critical conversations to have with your new bossYou’ve recently started a new job. You definitely feel like the new kid on the block – everyone is watching to see if you’ll succeed, if they can trust you, are you a pushover, etc.

There’s a mountain of work to be done and meetings to be scheduled. It’s difficult to know where to begin.

A word of advice: Begin with your new boss.

At the start of a new job, there’s no more important relationship to establish and nurture early on than the one with your boss.

Your first instinct may be to jump into the juggernaut of projects and tasks awaiting you. Fight that instinct. Otherwise you run the risk of getting overwhelmed immediately and will lose the chance to set direction and goals based upon your boss’s needs.

It’s your responsibility to reach out to your boss, to find out what you need to know and make the relationship work. Don’t expect your boss to reach out to you.

There are 5 critical conversations you need to have with your new boss. These conversations can be thought of as a dialogue that continues over several meetings.

The 5 conversations are:

1. Where does the business stand? Does your boss see this as a turnaround situation, a start-up, a re-organization, or is the goal to sustain success? Do you see this the same way your boss does? Discuss the challenges your business situation presents and the resources that are available.

2. What are your boss’s goals/vision? The most important question to pose to your boss is: How can I help you be successful? Pay attention to your boss’s priorities and aim for early wins in those areas.

3. How will your boss define your success? How will your success be defined in the short and medium term? How often will you receive feedback on your performance? If you feel the performance expectations are unrealistic, you will need to negotiate those parameters in future discussions.

4. What is your boss’s preferred method of communication? How does your boss want to receive communications from you— in person, in writing, quick emails, voicemails? How often? What types of decision does your boss want to be consulted on, and what decisions can you make on your own? Your boss’s answers to these questions will give you insight into his/her management style.

5. What resources are available to you? What resources does your boss think are critical to your success? This may consist of additional staff, budget or the backing of your boss to push through needed initiatives. Ask the questions now before circumstances dictate the outcome.

The information and direction you gather from these early meetings will be invaluable to your success. Use your best powers of persuasion with your boss and cite the ROI that will be realized by investing time in early conversations.


Looking for an on-boarding plan to be successful in your first 90 days in a new position? Check out my executive coaching services.

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