Imperfect Boss? Perfect Opportunity.

Jan 24, 2019

By Stefanie Smith

Helping your leader also helps you. It’s not a zero sum game. In fact, it’s the opposite. The more win-win experiences you establish, the more you’ll gain.

You may adore and admire your boss. Or, you may or not be compatible on a personal basis. I’ve heard it all, including “I hate his guts and hope he dies soon so I can have his job.” Rather than plotting his early death, act to contribute to your own advancement—there’s a lower risk of jail time, and higher probability of a salary increase.

Everyone realizes the boss is in control from a financial or organizational perspective. But you can gain immediate power and confidence in the relationship from calling to mind reasons to feel gratitude and acknowledging areas of positive influence.

Whether you seek to take your partnership from strained to good, or from good to glowing, reframing it in a context of mutual advancement benefits you in three ways:

  1. Adds to your sense of achievement and self-esteem. Anything you accomplish that happens to help your boss is also part of your permanent track record.
  2. Establishes positive predisposition and puts you on the same side. You’re worried about your boss? Guaranteed she is worried about her boss too. Or she is worried about the Board. When you are both working toward the same goals, you combine your energy rather than wasting it in a power struggle between the two of you.
  3. Demonstrates to everyone around that you are an asset. For others on a project team, your boss’s boss, or the guy interviewing you for the next higher powered job, if it is clear that you scored a win for your boss, you are instantly more desirable to have on board.

This will be fast and practically painless. I promise. But it does require active participation from you, because, truth is, I don’t know your boss like you do.

Please take 60 minutes to write out your responses to the following five questions. These are practical, not rhetorical questions.

Print this out and take it to lunch with a pen, or copy the following questions into a Word document. Either way, the real value lies in your real answers.

I. What three things do you appreciate or admire about your boss or learn from your boss?

These don’t have to be huge, just honest. We all want to work for someone we respect and someone who can help us advance. So this is our starting point. Consider both professional and personal traits.

Does your boss remind you of an appealing character in a movie or a novel? Does she communicate with style or use expressive vocabulary you find effective? Can she motivate others in a way you admire? Do her edits improve your writing? Does she consistently make eye contact and let you know she’s listening? Does she have an energetic approach to attacking an overwhelming task list?

Even after you’ve done this brainstorming, you have the right to remain silent. Or, at the right time you may choose to tell your boss –if and when if it feels authentic. But please, no gushing praise a week before your bonus review or the day after you put in a request for holiday time during a prime week. Even if you are overcome with a sudden wave of gratitude at those times, it may appear just too much of a coincidence.


II. What are your boss’s personal and professional weaknesses?

Go ahead. It’s absolutely fine to derive some enjoyment from writing this list. Yes, you can add more if you can’t possibly stop at three.

What areas does he find truly challenging? What skills can he simply not seem to master? Does he have weaknesses that embarrass him?

But while you are writing, start to really consider that some of his challenges may not be easy for him to overcome. I feel that way about some of mine, and you may feel that way about some of yours. It would be nice to have a perfect boss. It would also be nice to find a pot of gold at the end of a rainbow. If your boss is imperfect, you have a perfect opportunity to be valuable and be valued.


III. What three things could you do to make life better for your boss?

Maybe his weakness is your strength. Maybe you can help him through an upcoming challenge by putting in an extra hour a week. Maybe you can teach him some key phrases in Spanish before his sales trip to Mexico.

Some thoughts:

Respect his time. Everyone wishes he had more time. How can you give him more time to do what he needs or wants to do?

Respect his position. Everyone wants to feel good about his role. How can you add to his prestige?

Respect his concerns. How can you solve a problem for him? How can you directly contribute to his achievement of an important goal? How can you leverage your strong points to make your boss look better or feel better? How can you further his goals or compensate for his defects? If you resent him too much to do this, ask yourself why you continue this relationship and when you will start looking for a new boss. Not every boss is worth staying with, and that is a determination you should make as part of this reflection.


IV. What are three concrete ways your boss can enhance your job?

This is not an abstract question. Be as specific and short-term as possible. What do you want and how can she help you? Can she approve your attendance at a class or event? Can she delegate a leadership responsibility to you that will enhance your role? Can she spend thirty minutes to coach you every other Tuesday morning? Or would she approve the budget to hire an outside executive coach for you? Would she approve hiring a temp four hours a week to offload your filing?


V. How and when will you communicate these mutual opportunities to your boss?

In upcoming conversations with your boss, try to apply some or all of these responses, and focus carefully on his reaction. You know your boss, and you know what will work best. But don’t confuse ”what will work best” with “what feels most comfortable.” Those may be two separate answers.

Make the most of your chance to communicate respect and enthusiasm for an opportunity for mutual success. Remember: 93% of communication is nonverbal. So please consider a face-to-face discussion unless e-mail or phone is truly your first choice.

Again, this isn’t an academic thought process, it is a means to an end. Your goal is your advancement, or at least your sanity. Now you have a plan. More power to you!

If you would like to share your thoughts and experiences, please contact me.

About the Author(s)

Stefanie Smith leads Stratex, an executive consulting and coaching firm based in Manhattan. As an executive consultant, she works with business and government leaders to plan and execute strategic projects. Stefanie Smith also provides customized group workshops and private coaching programs to help executives and their teams reach the next performance level. For more information, see, speak with her directly, or subscribe to her blog at