Four Conversations You Should Have With Your Boss

yada-yada-1430679_640It goes without saying that regular communication between you and your manager is one sign of a healthy relationship. Ongoing, meaningful conversations are necessary to maintain your connection and ability to “read” each other. When you and your boss are in sync, work is smoother, more efficient, and more productive.

If contact is infrequent or impersonal, it can signify a lack of trust or a lack of engagement. Either is a sign of a degrading relationship and should ring alarm bell sin your head. A lack of regular communication is a symptom of larger issues that need to be addressed before things go too far. Should you find yourself wondering if you need to communicate more, you probably do.

But what kind of conversations should you and your manager be having? Beyond an exchange of pleasantries or questions about weekend plans, what kind of topics ought to be at the center of your dialogue? Here are four types of conversations you and your boss should be having:

The “What’s going on?” conversation: You and your manager should make an effort to keep each other in the loop regarding the current state of the business.

  • Discuss your numbers – What’s driving them? Is that spike or dip an anomaly or something we should have expected? How are the activities the team engages in day-to-day affecting performance?
  • Discuss your customers – What are they saying? What hits and misses have impacted your ability to serve lately? What are they getting somewhere else that you aren’t providing?
  • Discuss your team – Are people happy and engaged? If so, why> If not, why not? What seems to be working or not working as a team?

The “What’s coming up?” conversation: You and your manager should make an effort to look ahead in order to anticipate problems or spot opportunities.

  • What are the issues keeping your boss up at night?
  • What outside factors are putting pressure on the business?
  • What outside factors might provide an advantage for growth?

The “How can I help you?” conversation: Your manager has their share of projects to manage. You should be looking for ways to help them be successful. Never miss an opportunity to make your boss look good.

  • Identify ways you can add value.
  • Communicate your specific steps you can take and your desire to help.
  • Follow through with any commitments.

The “Will you help me?” conversation: It’s the job of the boss to help you, so they’re expecting this one. Save this conversation for last to illustrate your desire to work as a team, but don’t just dump your problems at their feet.

  • Identify specific steps you’d like for the boss to take.
  • Communicate the necessity of acting and the impact their actions will have.
  • Express gratitude for their continued support.

It’s tough being a boss. People look at you differently and most try to avoid conversations – either out of fear or a desire to appear independent. But your boss has the same needs you do – they want people they can talk to, confide in, and collaborate with. Make a point to be that person.


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