Managing Your Boss

How do you manage your boss? Is avoidance your preferred strategy, keeping out of your boss’s way as much as possible? When you have to meet your boss are you in a passive, defensive frame of mind, just waiting for criticism or difficult questions? Maybe you were awake half the night thinking of how you will defend yourself against any possible criticism.

I worked with a woman a number of years ago who was very critical of her boss. She thought she should have got the job that he got. She criticized the new boss, even to his face. I said to her: “If you were a retail business, how far do you think you would get criticizing your customers for not buying enough from you?” A lose-lose tactic, criticizing customers. To better achieve your own goals, try to see your boss as an internal customer, likely your most important one. This shift in mindset should stimulate you to see meetings with your boss as an opportunity rather than as a burden.

The best way to serve customers is to begin by learning their needs.

Asking your Boss: “What do you want?”

Begin by stressing that you see your boss as your most important internal customer. Say something like: “To best support you, as a key internal customer, I really need to know what’s most important to you. What are your objectives, priorities or needs? What would you like me to do differently or be better at?” What does success look like to you?” “How can I best support you?” Using this approach to managing your boss, you are asking engaging questions of the form “What do you want?” This is very self-empowering to avoid just passively waiting for our boss to tell us what to focus on.

If you don’t ask your boss “What do you want?” questions, you are making up your priorities for yourself. This is like throwing darts in the dark. Yes, you know your job but your success partly depends on helping your boss be successful. This means thinking strategically about yourself with questions such as: “Should I do what I think is most important here or should I find out what my boss most needs from me?” If you address this question with a customer-first mindset, then you should be adjusting your focus to put more emphasis on your boss’s priorities. This is simply thinking strategically about yourself with a customer-first mindset, about how you can add most value in a given situation.

Asking about your boss’s priorities doesn’t mean being a doormat. You can also ask questions that are challenging but not confrontational. If your boss makes a suggestion that you think will not work, express your disagreement by first saying what you like about your boss’s idea, then make suggestions, in the form of questions, to get around any obstacles you can see: “If such and such an obstacle arises, how do you think X would work to get around it?” “If you don’t think that would work, what other options would you suggest?” “What do you see as the pros and cons of those options?” Keep making suggestions in the form of engaging questions such as “How do you think X, Y or Z would work?” As with any customer or client, you need to strike a balance between meeting their needs and helping them see that there may be better ways of addressing their needs than the suggestions they make. Striking this balance means ensuring that your clients don’t feel that you think they are idiots for having dumb ideas. Keep in mind that most bosses may be even more sensitive than clients about being made to feel dumb by a subordinate.

Asking “What do you think?”

Suppose you want to impress your boss by making suggestions about changes you have thought of or solutions to a current problem. Keep in mind that organizations are hierarchies of authority where most bosses feel that they should have all the answers. Some are more sensitive about this than others. If your boss is on the sensitive side in this respect, offering your suggestions could backfire as your boss may think that you are trying to be smarter than you should be as an organizational inferior. Enthusiastically worded suggestions, no matter how good they may be, can seem like criticism to many bosses. It can sound to the boss like: “You can’t be that smart or you’d have thought of this yourself.” You can reduce the risk of seeming to be a threat to your boss by putting your suggestions in the form of “What do you think?” questions.

If you have a suggestion to make about a process that could be more efficient, you could ask your boss:

  • How do you think we might make this process more efficient?
  • What options do you think we have for addressing this issue?
  • What option do you think would work best?
  • How do you think we might go about implementing one of your suggestions?

If your boss can’t think of a fix, offer your suggestions in the form of “What do you think?” questions:

  • How do you think X would work as a solution?
  • How might we modify X to make it work better do you think?
  • What obstacles or risks do you see if we were to adopt X?
  • How might we best address any such obstacles or risks?
  • How do you think Y would work to address the risk/obstacle you mentioned?

Engaging questions are less confrontational than statements and more likely to foster constructive two-way dialogue. By asking such questions, you are acting as a facilitator, coach or catalyst instead of as a clever solution generator. Using engaging questions shows leadership while offering your own solutions is acting more as an individual contributor. Asking engaging questions fosters collaboration or team work, shared ownership and shared commitment.

Appraising your Performance

Most bosses find performance appraisal difficult. They want to improve your performance but, at the same time, avoid demotivating you. Some bosses over emphasize your shortfalls because performance is number one for them. Others over emphasize your achievements to avoid demotivating you.

A more customer first approach makes the whole process easier for your boss. Offer to lead your performance appraisal meeting by talking about three things, inviting your boss to add anything you missed. Here are the 3 things you should talk about:

  1. List the key things you feel good about that you have achieved since your last appraisal.
  2. List the things you feel did not go as well as they might have done.
  3. List the steps you plan to take to address the shortfalls in your second list.

This approach makes it easier for your boss and is a great opportunity for you to make sure your boss knows all the good things you have been doing. You can use the same approach with regular updates with your boss, whether weekly or monthly. Offer to take the lead in the same way. End the meeting by asking what are some things your boss would like you to do differently or better.

Taking the initiative to lead your own appraisal makes it easier for you as well as your boss. By creating a chance to tell your boss all the good things you have done, you have less to fear than if you are just passively waiting for your boss to drop bombs on you. When you fear criticism, your natural reaction is to be defensive by dismissing your mistakes or blaming someone else. But when you can talk about your successes first, it is then easier to admit your own slipups.

Volunteering

By regularly asking your boss about new priorities or challenges, you can volunteer to get involved in a new challenge that might help you learn some new skills or raise your profile in the organization. By focusing on your boss’s priorities, you build trust with your boss and are less likely to be seen as a threat if you volunteer to be delegated new challenges. Stress that you see this as a learning opportunity for you, so that there is no implication that you want to usurp your boss’s role. Don’t forget to ask your boss a “What do you want?” question like: “How often would you like an update and in what detail?”

Conclusion

When you ask engaging questions of any colleague or external stakeholder, you are showing interest in them, their needs, priorities and experience. Showing interest is often a better way of selling yourself to people than telling them how great you are. People like you better when you ask questions that get them talking about themselves and their ideas. It’s a subtle form of flattery, a good way to build a relationship with bosses and other stakeholders.