Steps for Dealing with a Difficult Boss

A client asked me how to deal with her difficult boss. She felt angry and upset about her manager’s duplicitous management style. He professed a democratic, consensus-building style while making command decisions. At the same time he seemed oblivious to the inconsistency and its impact on his staff.

My client was less upset about the command style – her manager could run the office as he saw fit. The frustration came from the gap between the manager’s self-image and the actual actions. This gap created distrust, anger, and was the reason for her calling me. Below is my summary of the advice I gave my client.

What to do?

The short answer is approaching your boss about a pattern of behavior you find disagreeable is risky. There is a very small chance that your boss will thank you for opening his eyes to bad behavior and offer you a promotion for speaking truth to power. A more likely response is that your boss will get angry, dismiss you (and your complaint), and will not welcome your presence and ideas for many meetings to come.

Does that mean you don’t let your boss know what happened? Hardly. In fact, your boss’s alleged transgression is a great opportunity to practice your conflict leadership skills, as well as build a stronger relationship. Doing this, however, requires a soft touch and clear understanding of your interests, as well as your manager’s.

Step 1 – Determine the trigger.

Before approaching your manager, make sure you understand what happened. It’s important to determine the exact trigger (or triggers) so that you can effectively relay your complaint to your boss. Specific issues are more actionable and easier to address.

When did you first feel that something was amiss? Was it in a meeting when you were caught off guard by a decision or was it an email that copied the world about something that you thought was confidential?

What is so important about this particular issue that landed poorly with you? Was the actual conversation/email/etc. so egregious or was it a minor issue in itself, but served as a reminder of a larger issue? It’s an important distinction and we will return to it later.

Did the way in which you found out play a role in your distress?Was getting the message in public particularly unpleasant? Or was the timing particularly poor? Maybe it was the method (email or phone vs. a face-to-face meeting).

Step 2 – Clarify the impact.

Now that you understand what triggered this incident, get clear on what effect that trigger have on you. It’s equally important to be clear about the impact the triggers had. Be mindful, however, of limiting the impact on you. Be careful to avoid the perception of trying to represent others (unless they specifically asked you to speak on their behalf).

What was the emotional impact TO YOU of what happened?How did finding out what you did, in the way that you did leave you feeling? Offended? Betrayed? Livid? Alienated? All of the above? It is critical to accurately identify the impact of the incident on you. It is equally critical to contain these reactions to you and only you.

We are often tempted to buttress our points by herding others’ experiences with our own (e.g., I am not the only one who feels this way. The whole group thinks so, too.). The likely impact of such a statement is alienation and defensiveness from the person hearing it. After that, there will be little chance the person will remain open to your point.

Was there an impact on others? If so, identify it, and then reframe it as impact TO YOU.

It is quite possible that in addition to the impact on your work, your boss’s failing impacted your staff, colleagues and others. You may even feel that it is your duty to inform your boss of this. However, in doing so you are risking appearing arrogant and giving your boss an easy excuse to dismiss your point. (After all, who do you think you are to purport to know better than your boss about the impact his action had on others? Or did you go talking behind his back? - See where this could go?)

You will be on safer ground by describing this part of the issue as feeling protective of your subordinates who, might have to work late, etc. Phrasing the problem this way will make the point without intruding on your boss’s authority as well as make you look like a good manager who is concerned about your people.

Step 3 – Set your goal.

The last step before asking for a meeting is making sure you know what outcome you would like. It helps to be as specific as possible. Do you want your boss to be more inclusive or just more consistent about the style he applies? Becoming clear about what behaviors you would like to see is vital to having a successful meeting.

As soon as you determine your goal, understand that you might not even bring it up in your initial meeting. In fact, it might take several conversations before your boss invites you to let him know how to act differently. So, be ready, but not attached to this part of the conversation.

Step 4 – Choose your location and timing.

Once you understand the trigger, its impact on you and what you would like your boss to do differently, it’s time to meet with your boss.

Pick a time and place that is more conducive to him being receptive and engaged. Be sure to consider the time of day of your meeting, your boss’s mood, energy level, etc. Also think about where you would like to meet.

It would not serve your purpose to make your boss feel set up for a public shaming. Since you are taking the leadership role in approaching your boss, it is up to you to pick a place that is most appropriate and conducive to your conversation.

You could ask for a meeting in his office; a conference room, or, even a local coffee shop. Any of these could work, as long as he understands that your proposed location is aimed at making him feel more relaxed, comfortable, and free from public scrutiny.

Step 5 – Invite your boss.

When asking for a meeting, select an approach that subtly communicates the importance of the meeting to your boss. The manner in which you make the appointment is up to you, as long as it shows that you are serious about the meeting without making your boss feel caught off guard. Beware of making him feel forced to see you. If he does, it will make it that much harder to communicate your points effectively.

Your boss will likely ask what the meeting is about. Saying “I didn’t like what you did and want to discuss it” is risky as it will likely put your boss on the defensive. You might say something like “I received an email that concerned me” or “I heard something in a meeting that concerned me.” Using this phrasing you are being truthful and alerting your boss as to the broad theme of the meeting without making him defensive.

Step 6 – Have the conversation.

It is likely that the beginning of the meeting will feel tense, at least for you. This is natural and that feeling will go away quickly once you delve into the meeting. Of course, acknowledge the accommodation your boss made by seeing you. This will make your boss feel more relaxed, engaged and willing to hear your point.

In communicating the substance of your grievance, follow these rules:

Be sure to stay on your side of the line between your boss’s actions and their impact on you. SPEAK ONLY ABOUT THE IMPACT.

Avoid labeling your boss’s intention and actions.

Be specific about the trigger(s) which caused your original upset (refer to Step 1). Make sure to limit your triggers to the number your boss can digest.

For example, you might say: “When I received your April 10 email, I became upset because of what I perceived as ...” or “When I heard you say ... in our April 10 meeting, I became upset because of what I perceived as ...” Use this specific language to allow for room between your boss’s intentions and your perceptions.

Once you explained your point, give your boss a chance to respond. Don’t overwhelm him with too much information and emotion. If your boss seems engaged in the conversation (even if it is only with his body language), from this point forward let him take the lead by remaining silent.

In most cases breaking the silence will take a few seconds. Your willingness to remain silent will let the boss know you are waiting for him to take charge of the conversation. From this point on, if he asks you more questions about what happened, answer them. However, don’t try to drive more points home, or insist that he take some corrective action unless he invites your suggestions.

You may have to wait for your boss to commit the same mistake twice and repeat this conversation at that time. If you do it effectively, each time your boss will be more trusting and more accepting of your suggestions (assuming you keep each conversation confidential).

If your boss tries to change the subject or avoid the issue during your meeting, bring it back to your point by restating the impact on you: “I am still upset about the email/meeting.” Remain respectful and patient - some people need longest to enter into a difficult conversation.

However, during your meeting, continue to come back to your point until you get acknowledgement. At some point your boss will likely acknowledge your point by asking you a question about it. Once he does, you have dialogue.

Alex Yaroslavsky