At some point in our careers, we all run into a boss that we have difficulty working with. I know my clients face this all too often. Countless articles and books have been written about “managing up” and actively promoting your work to your boss. But often the guidance comes off sounding cynical and manipulative. Being a “yes man” or playing office politics is not likely to improve your relationship with a boss.
Instead, a better approach is to partner with your boss. There are three predominant types of bosses I have encountered, and each requires a different approach when it comes to partnering with them. They each care about different things and have different styles and ways of working.
Visionary Boss
The Visionary boss is a big-picture strategic leader who can have a million ideas, some of which are brilliant and some a waste of time. Your job is to help define and implement the brilliant ideas. This type of boss tends to stay out of the details, trusts you to make the vision a reality, and rewards you for figuring out how to implement the best ideas. Visionary bosses tend to be positive and not critical. They can also leave you out of decisions and not communicate changes that may affect you—not from malice; they’re just not paying attention to details.
Since this boss is so big picture, it may be hard to understand what she wants. As a result, you may find that your efforts to develop project plans were wasted because your concept didn’t hit the mark. But asking your boss to better define her ideas at the outset will not likely be taken well. Rather than constantly throwing darts into the dark hoping you hit something, try developing an outline (or “beta” or strawman) so you can get the early feedback you need to know you are on track.
In partnering with this type of leader, your role is to put meat on the bones of her ideas, add details that she might not have thought of, and clarify areas where she is vague. When she sees that you understand her vision and she can trust you to bring her ideas to fruition, she’ll become one of your strongest supporters.
If going from vision to plan isn’t your strength, you will likely find a Visionary boss frustrating. If you work best with structure and clarity, you will probably always struggle with this type of boss and may want to find another person to work for.
Detail-Oriented Boss
On the other side of the spectrum is the Detail-Oriented boss, who may be perceived as a micro-manager. This type of boss tends to think he can do everything better than his direct reports, and often he can. He can be critical, picky, and reluctant to give those on his team much autonomy. But he knows that to be successful as a leader he needs to get out of the details and think more strategically. You can help him out of this bind if you demonstrate your ability to get the job done to his exacting standards. The mistake in dealing with micro-managers is to respond by withholding information. “Starving the beast” will only increase his distrust and need to control. With this kind of boss, I find including him early and often will build his confidence in your ability and create trust. While the Visionary manager can be frustrated with detail-oriented questions, this boss enjoys getting his hands dirty and problem solving with you. He is happy when you include him and value his expertise.
The key to partnering with this type of boss is not to get out ahead of him. Keep him informed of your work so that he feels in control. Make sure you are factually correct and pay attention to details. He will notice mistakes and doubt your competence if you make too many, regardless of how inconsequential they seem. And if you don’t own up to them, he will not trust you. If you aren’t detail oriented, you may feel like you can never please this type of boss; you may even come to resent what you think of as his excessive attention to the smallest details. When he comes up with a small correction, instead of being upset or feeling that you are never good enough, realize that you gave the boss a chance to feel he added value.
Laissez Faire Boss

In the middle is the Laissez Faire boss, who is neither visionary nor detail oriented. Her bastion is the steady state and she avoids sticking her head and neck out above the ramparts. Her motto: “If it ain’t broke, don’t fix it.” She has survived by minimizing risk and staying under the radar. The worst thing you can do as her direct report is to attempt something that might turn out great, but could also fail miserably and conspicuously. Rather than playing to win, she is playing not to lose. She may not trust her own expertise, and certainly not yours, so it can be helpful to determine who she does trust and build a relationship with that person. When she learns that person has blessed your idea, she will be more willing to give it a shot.

The best way to partner with a Laissez Faire boss is to demonstrate your own commitment to minimizing risk. A small pilot that tests your idea—and includes a thorough risk assessment and mitigation strategy—will put her more at ease. If, even with successful pilots, your ideas prove too dicey for this boss, you will want to look for a less risk-averse leader.
Winning Strategies with Bosses
Regardless of your boss’s style, being a productive partner means alerting him to problems and offering solutions. Three benefits result from this: 1) you demonstrate your expertise and problem-solving skills, 2) you obtain feedback that helps you be more successful, and 3) you show your boss that you value his expertise. You may think that keeping problems from your boss—solving them on your own without seeking his input—makes you a better employee, someone who doesn’t need to be constantly managed. But the reality is that your boss may not be aware of all the challenges you are tackling. Seeking his input after you have thought through the issues is a good way to keep him apprised of your work. Including your boss in this process may also cause him to feel some ownership for your success. Even secure bosses can feel irrelevant when you accomplish great feats on your own.