Leading other people is a noble pursuit. When you can help someone develop skills and realize success, it can be gratifying. Humbling. Rewarding. Hopefully, that drives you to become a better leader.
Leading others can also be challenging. We’re dealing with humans, so there are unique behaviors, motivations, psyches and backstories that each of your employees carries with them when they walk in the door each day. Personal needs. Triggers. Blind spots.
It can get messy. Uncertainty abounds.
With that in mind, you reach out for best practices on communicating, delegating, and all the other skills that come with managing others.
But what about your boss? How do you effectively manage “up”?
It can be a risky proposition. Your boss can impact your future opportunities. Your career.
But your success may require you to influence your boss. Your team may need you to take on that responsibility.
There are some realities about the role of the boss that you need to understand. And there are some behaviors you need to model and some responsibilities you need to embrace.
So that the relationship will work. So that you can be successful.
The Realities of the Boss Role

You may have a great relationship with your boss and be lucky enough to be working for the dream boss. 😇Congratulations, you’re in a minority.
You may also be working for the boss from hell. 🤯 You have my condolences.
Most bosses sit somewhere in between.
In any case, there are some realities that go along with the relationship with your boss that you need to keep in mind:
- They have influence over opportunities that can come your way
- They have influence over your compensation
- They can impact your visibility in the organization
- They can impact your reputation and your political capital inside the organization
- They can impact the pace or trajectory of your career development
- They can fire you (yeah, no way to sugarcoat that one)
Depending on the lens through which you look at these, they suggest that there is potential value when the relationship is working well, and some risks when the wrong dynamics are present.
Keep in mind that the boss / subordinate relationship is one of mutual dependence. As such, it takes some effort to not only understand it, but to improve it.
There are also some realities about the person that you currently call your boss.
- They’re human
- They have flaws
- They make mistakes
- They have an ego
- They have personal needs
- The have their own career aspirations and concerns
- They’re likely delusional***
***In 2016 McKinsey surveyed 52,000 managers and 86% rated themselves as inspiring and good role models. During the same year, Gallup conducted a survey where 82% of employees said their managers were uninspiring and only 13% of the workforce was engaged. Historical studies suggest that the higher a person is in an organization, the more they lack self-awareness. This is both the challenge and the opportunity for you.
***This should get your attention, like a flashing neon sign. If the majority of leaders are delusional, take pains to be informed and self-aware. This is one of those times you don’t want to join the majority. 😳 Seek honest feedback and act on it.
Specific Strategies for Managing Up Success

You may or may not be working for the person who actually hired you. That was probably the only time you had a chance to pick your boss.
When you were interviewing. While you were looking for a job. Not necessarily the time in your career when you are most discerning and at your objective best (although you should be!).
But here you are.
In order to create the healthiest relationship, here are some strategies for you to pursue:
- Seek to identify your boss’s strengths, weaknesses, blind spots, and hot buttons, in order to inform where and how you can add value. You want to help them leverage their strengths and make sure you can either support their weaknesses, or at least not let those weaknesses impact your effectiveness. You can help them see their blind spots, when appropriate. Be careful not to push the hot button topics. You’ll likely get an emotional response that doesn’t do them — or you — any good.
- Know your boss’s favored communication style (brief and concise vs. data and facts vs. verbal and conversational, etc.). When the outcome is critical or the interaction is important, make sure you approach them in the style that resonates most effectively with them.
- Make sure you know, at any given time, the #1 most important thing they need from you. Make it a topic that you check in on regularly. Take responsibility for making sure it is verbalized and you have clarity around expectations (quality, time frame, cost, etc.).
- Operate with a perspective of “no surprises.” If something is off-track, related to completion date, quality, etc., let your boss know, along with your plan to get it back on track. Try to communicate any issues in advance to protect your boss from the threat of being blindsided.
- Know your boss’s most important goals and how you can best contribute to their achievement. You can determine the frequency of this, but I would check in at least monthly. If you know their goals, you may be able to identify sources of stress before they ever show up in the workplace. If your boss isn’t good about identifying priorities, this may be a subtle way to get him or her to make some progress.
- Be aware of their leadership weaknesses and don’t allow those weaknesses to negatively impact your performance. Overcome their weaknesses, so that you don’t have any excuses. For example, if they’re poor delegators, you can reverse-engineer the delegation process, to get the information and understand the expectations, in order to be successful. If they are poor communicators, set up systems to get the appropriate information and insights that you need, when you need them.
- Create a cadence for communications, so you can share relevant information that they need to know in a timely manner. If you don’t currently have a weekly 1×1, you may want to suggest it. Some bosses don’t like them because they feel the burden of coming up with agendas, or it becomes little more than reviewing your to-do list. If you believe the meetings are important, you can take responsibility for setting the agenda, creating the accountabilities and follow-up, as well as validating the mutual benefit of regular meetings.
- Make sure you know what drives them. This isn’t always expressed, but it shows up in how they spend their personal time and resources, or what lights them up in conversation. Look for opportunities to allow them to focus on those areas. It may be making them aware of opportunities, or eliminating other tasks that keep them from being able to experience their most important drivers or interests.
- Work hard to develop a level of trust so that you can share your honest observations with your boss. Trust is critically important and some bosses are better at extending trust than others. Keep working at it and don’t do anything to violate that trust. Sometimes, the emperor needs to be told when he isn’t wearing any clothes. Some bosses are more open to feedback than others, but your relationship needs to get to a point where candor safely exists. The greatest practice you can prioritize to build trust is to do what you said you would do. Every time.
- Keep the monkey on your back. This refers to the Harvard Business Review article, “Who’s Got the Monkey,” that warns leaders not to allow subordinates to dump problems in their laps — even after it has been delegated. You can ask for help, but once you take responsibility for something, own it. If your boss has to complete your tasks or do your dirty work — then they don’t need you. 🤨
Note: No part of this relationship, or these recommended strategies, is based on brown-nosing, sucking up or being a political animal. It is based on professionalism, confidence and doing the right thing. It also assumes that your boss never asks you to compromise your ethical and moral compass. Sometimes you have to hold up the mirror. Sometimes you have to stand for what you believe in, despite the consequences. Most bosses want to do the right thing. Unfortunately, some are toxic. Distinguish between behaviors that are mistakes in the moment and those that are a pattern of destructive acts and ill intent. Life is too short to stay tethered to boss who is a terrorist or a toxic jackass.
You Own This!

As leaders, we often focus our skills and development on how we manage and lead our direct reports.
That takes plenty of energy and attention.
But we also need to be mindful of our own bosses and the importance of that relationship to our careers. To the performance of our team. To our leadership brand.
Bosses come in all shapes, flavors and sizes.
They might be somewhat dysfunctional.
They might even be delusional. 😬
But the relationship is too important for you to wait for them to shape it or direct it.
If you are working for a toxic personality, it is time to work for someone else. Or for yourself.
If the relationship could stand for a bit of improvement, then it is time for you to take responsibility.
For your actions. For your part.
Don’t be a victim. Don’t wait on someone else to determine your future.
You own it. Implement the strategies outlined above to improve the relationship. To make a difference.
It’s your career.
Your team.
Your brand.