Ten essential conversations every leader must initiate with the boss

Fifteen months ago, Mark Newton was the hotshot hired to turnaround the organization. He had the resume, the talk, and the charisma. Yesterday, he was the fired.

Mark’s boss told him in the termination meeting that he had failed to deliver the needed results. Mark argued back he had increased sales 3 percent, he hired 2 new people, and they were on track for next quarter. His boss acknowledged those outcomes but said they weren’t the priority. Mark tried to counter that the boss never let him know. That argument went nowhere and today Mark is job hunting.

You may want to make the case that the boss should have done a better job of defining success—and you would be right. However, in spite of being right, the consequences fell on Mark, not the boss.

Most bosses feel they have clarified the direction. They said it once or twice and assume you are on the same page. Yet, the reality is that you and your boss may have significantly different perceptions about processes, priorities, and results.

How can you avoid this dilemma with your boss? You need to proactively initiate ten conversations (And, you don’t just do this when you start the job).

  1. What are the key results we need to achieve over the next 90 days, 12 months, 3-5 years? How will you know we succeeded? (You must make sure you are both going the same direction. Find out the story in the bosses head, not just the high-level bullet points).
  2. What constraints do we have? (Make sure you understand the perceived and real limitations and obstacles of the situation. You need a clear picture of the playing field).
  3. How have we performed over the past 3 (6 or 12) months? Is it meeting/exceeding expectations? (Make sure that you understand the bosses perception of your results and the organizations results).
  4. How are you being measured? (Determine the pressures your boss is under. Make sure your actions facilitate his or her success).
  5. What is the reality of politics? How do decisions get made? What relationships are critical? (You must understand the rules of engagement. It’s not petty for people to want their needs to be met. It’s life).
  6. What decision-making authority do I have? (Find out the boss’s willingness to let go — but realize most bosses back off of what they said when times gets tough).
  7. What are your communication preferences? (Some leaders argue that this is one of the tests of leader—can you figure it out without asking. However, others say get in and ask, “How do you like to hear bad news?” “When do you want in person versus email?” or “What are your pet peeves”).
  8. What feedback do you have for me on ____________? (Ask for feedback on specific areas so the boss can give relevant feedback and you can take immediate action on the right things. Remember, if you think it is hard to get feedback throughout the process, trying the pain of getting it at the end).
  9. Let’s talk about my team’s successes (Sharing successes does not have to be politicking. Sharing success provides your boss with important data to make decisions. If you don’t share it, it never happened. Share your team’s successes throughout the project)
  10. Are we still aligned? (If you ignore this one, it may not matter what you did in all your other conversation. You must periodically check in to make sure the direction you are going, the process you are using, and the relationships you are building are on track).

Creating clarity between you and your boss is a series of conversations. Each interaction creates the path for more trust. One of the most enjoyable conversations you will ever have is sitting down with confidence and saying, “Here are the results you asked for.”

The converse of this is to ask yourself as a leader how well you are doing at providing clarity to your people on the 10 items listed above. Most leaders think they are doing better at these than their people do. Take the time to make things clear. This job is never done. It requires retelling and retelling.


About the Author
Dave Jennings accelerates meaningful change. He has worked with leaders from 20 of the Fortune 500 and spoken in 23 countries. His articles and commentary have been featured in The Washington Post, Forbes, and thestreet.com. He is author of Catapulted: How Great Leaders Succeed Beyond their Experience. Contact Dave at dave@davejennings.com.
  1. Ken Lader Reply

    This is a great list. As a manager in a new role, I’ve been using this in conversation to focus in on my boss’s expectations. Clarity and direction are cornerstone values for workplace success.

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