Crucial Skills®

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Crucial Conversations for Mastering Dialogue

Approaching a Hard-to-Please Boss

Dear Crucial Skills,

I have a problem at work involving a boss who is never satisfied. Our branch has the highest ratings possible and yet our annual letter from the boss always says, “I know we have the potential to be good.” This wording sounds as if we are not good now, despite having the highest possible ratings. How can I show my boss that a more positive approach would improve employee morale and help productivity?

Discounted Employee

Dear Discounted,

What a frustrating situation: the glass seems to be full, but your leader describes it as half empty. This is a perfect opportunity to use the Crucial Conversations skills: master my stories and explore others’ paths. You receive an ambiguous and disappointing message from your manager. You see his or her story, but you don’t know the facts behind it. In addition, you draw conclusions and tell yourself a story about your manager.

The key to solving this issue is to learn what your manager is really trying to say—and to make sure you interpret the message accurately. Let’s imagine his or her motives and then explore solutions.

The annual letter may be more ceremonial than informational. Your leader may send similar letters to every branch every year. In this case, the letter isn’t meant to be taken personally. Instead, it’s meant to convey your manager’s overall philosophy: that your company has great potential to do good work.

Before you talk to your manager, touch base with a coworker from another branch to make sure you’re not overreacting. If you find out the letter is just ceremonial, then put it in perspective. It may not be worth a conversation.

Your ratings may not tell the whole story. There may be other metrics, such as overtime, staffing levels, market penetration, profitability, and the like, that aren’t captured in the ratings but that still matter to your leader. If this is the case, then your team needs to track these other metrics and work to improve them.

This is a conversation you and your peers need to have with your manager. Here is a possible starting point: “Your letter made me wonder whether our number-one rating isn’t really telling the whole story. You said we had the ‘potential to be good.’ Are there measurements of our work that aren’t reflected in the ratings—aspects we need to improve on in order to be ‘good’?”

Your manager may fear complacency. Even the best individuals and teams need to continually improve or they’ll be left behind. Some leaders are afraid too much praise will cause people to become content with their current level of performance and slow their continuous improvement efforts. If this is the case, then your team needs to have clear and visible stretch goals so your manager can recognize your progress while acknowledging your achievements.

This is another conversation you and your peers will want to have with your manager. A starting point might be, “As you know, our branch is ranked number one. Yet, your letter didn’t exactly celebrate our achievement. You said we ‘had the potential to be good.’ I want to check in with you to see if you think we’re becoming complacent or if there is some other problem I’m not aware of.”

Overall, it sounds as if you have two tasks: First, to make sure you and your leader agree on how the branch is performing. That’s the focus of the suggestions above. Your second task is to help increase the motivation, morale, and productivity in the branch. Here are a few suggestions.

Manage the data stream. Make sure your leader and your team monitor the same dashboard. Work with your manager to determine a few metrics that create a balanced snapshot of the branch’s performance. Set challenging improvement goals and then update your progress daily, weekly, or at least monthly. Frequently seeing this feedback and progress will reduce any gaps between how your leader and your team judge the branch’s performance.

Increase opportunities for feedback. An annual letter should be one piece of feedback among many. Additionally, this feedback should come from a variety of sources beyond your immediate manager. Consider the variety of internal and external customers your branch supports and then create forums for getting their feedback. Listen for the good, the bad, and the ugly. When possible, include your leader in these information-gathering sessions so he or she can hear about your performance from those who are most affected by it.

Create personal experiences. A letter isn’t nearly as impactful or motivating as face-to-face dialogue. Find ways to visit internal and external customers. Invite leaders—your manager and others—to visit your branch. Encourage these leaders to share their views on how your branch can achieve broader business goals, where your performance is on track, and how you can improve.

Share mission moments. Take time to relate incidents that tie the branch’s work to its mission. One story per meeting is plenty. These stories should be timely and involve everyone. These stories of actual incidents will prove far more motivating than any yearly letter could ever be.

I hope these suggestions help you get started. Please don’t have the crucial conversation with your manager until you’ve first checked your perspective with a few trusted peers. Focusing on an annual letter your manager sees as nothing more than symbolism might get you labeled as a complainer or as overly needy.


You can learn more insights and skills like this in Crucial Conversations for Mastering Dialogue

3 thoughts on “Approaching a Hard-to-Please Boss”

  1. Bill Deeb

    David Maxfield’s analysis, friendly approach, and comprehensive review of the situation as described by the branch employee is thoroughly commendable. He focuses the employee on best practice approaches to meet the needs of the branch staff. This is the sort of wise counsel that helps less experienced staff mature professionally at an accelerated pace.

  2. Gary Cohen


    Sound advice. My experience tells me that this type of leader without a desire to change and without help, will create a demoralizing environment for those not set up to cope with the glass always empty, never satisfied personalities. What is your take? Gary

  3. Assistant

    My problem with this tactic is that it feels like you’re feeding fuel to the fire. You are trying to adapt to a toxic environment set by the manager. How long do you think you can sustain?

    A leader must lead, but if he is not capable of noticing his flaws then he is a failure.

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