It’s hard to sit down for a 1×1 with a problematic boss.  Bosses can be problematic for many different reasons, some of which are relatively addressable by you, others less so.  This post discusses how to get the most out of your 1x1s despite your boss’s particular issues and how to minimize the chances they will go badly.  How exactly you do all that, of course, depends on which type of problematic boss you have.

An overworked but otherwise benevolent boss.  With the overworked boss, you are going to get less of his or her time than you would from someone with a normal workload.  That means you must manage your time together carefully: you must schedule your 1x1s, rather than rely on being able to have them when your schedules allow, because your boss’s may not.  You must follow up (usually via email) promptly and consistently afterwards with notes about what you agreed to, if your boss’s being overworked results in forgetting details about what you are doing.  And you must be careful to bring all the information you need to your 1x1s, because an overworked boss won’t have time to reschedule.  Do everything you can not to waste the time of an overworked boss.  1x1s are not wasted time, for either you or your boss, but inefficient or sloppy ones are.

A boss ignorant of your field or project who wants to learn.  This kind of boss usually arrives in your workplace life after a reorganization, when s/he takes on teams and projects new to him or her, or when a new project comes along and lands in your boss’s lap.  If you have worked on it for a while, you may understand more about it than your boss. In your 1x1s, you have to allow more time than usual to give your boss the context of the project s/he needs, and you need to make sure the information is available in project or group documentation, because you can’t assume shared knowledge.  If it is a new field rather than just a new project your boss takes on, s/h is not going to learn an entirely new field quickly, so be sure to provide critical information first in support of decisions s/he will need to make.

A boss ignorant of your field or project who doesn’t want to learn.  Sometimes a boss doesn’t want to learn owing to laziness, sometimes owing to work overload.  Either way, you have to be extremely selective about the context and information you provide to your boss for decision-making: you must describe the managerial decision you need them to make, give them the context or information they need to make it, and explain why it is necessary.  In general, you have to ask this kind of boss “How much information would you like about [topic]?  I have information that is critical, some that is helpful, and some that is nice to know.”  Then make sure you give him or her all the critical information, and make sure everything to say is critical really is.

If a key decision is coming up, and your boss doesn’t want to or can’t take time to absorb the context necessary information to make the decision carefully, you have to point out, tactfully but explicitly, what is at stake in the decision, and what information you believe is necessary.  Then follow up with a short confirming email after your 1×1.  This will look less like CYA behavior if you send brief follow-up notes after every 1×1, which you should do anyway.

A boss who doesn’t like your work.  As a project or time goes on, you may sense that your boss doesn’t like some aspect of your work, even if s/he doesn’t tell you directly.  Don’t let that simmer below the surface: difficult as it is, you need to ask about it directly.  The key to doing so successfully is to ask about a finite, addressable part of your work, and make comments on the basis of data rather than on the basis of personal feelings: say “In the review meeting I saw that you didn’t like my last proposal draft much; can you tell me where it went wrong?” rather than “I get the sense you don’t like my stuff.”   Then fix what gets called out, and focus on that aspect carefully going forward.  Many bosses will only figure out what they didn’t like when they get asked a clarifying question, and it is in your interest to ask.  If the comment is general rather than specific to a project (“I find your market analyses weak”) ask if there is formal training, review material, or mentorship available to fix your weak areas.

A boss who doesn’t like you.  We all like some people more than others, but it is hard to have a 1×1 with a boss who doesn’t like you much.  That dislike may be because of a personality difference, or it may be because your boss was personally fond of the last person to hold your job and holds it against you for not being that person, or for any of a hundred other reasons.  There are two diametrically opposed ways to handle 1x1s with this kind of boss.  You can focus your 1x1s entirely on the work, and keep the workplace professional, without much of the personal chitchat that takes place when people in the workplace know each other well.  The implicit position you are taking is that this is a job, and you’re here to do it, whatever your boss may think of you.  The other approach is to address the matter directly.  The next time you get evidence of your boss’s opinion, address it as soon thereafter as you reasonably can: “Did you not like my last presentation?  Is there some way to make the next one better?”  If you start off by talking about work, you may get to a better working relationship by showing your boss you are making an effort to do so.  Above all, you do not want to fail to address a legitimate work issue because you write it off as personal dislike.

Sometimes your boss’s personal opinion of you will not rise, and is not a solvable problem.  If you come to that conclusion, particularly if you are in a small workplace or a small team, make sure to do your work well and keep your professional reputation strong and to have good relationships with other colleagues.  Keep your résumé up to date (which you should always do, even if you like your boss and your job) and keep an eye out for openings within your organization or in another one.

A boss with a bias against you.  This case differs from a boss who doesn’t like you in the reason for that dislike and in the result: the reason is a bias owing to your race, sexual orientation, gender, religion, or some other characteristic of yours not related to your work performance, and the result is unfavorable treatment of you in your workplace, whether in personal treatment, individually or in front of others, or in work assignments or evaluation.  If you suspect or know this is going on, you should conduct your 1x1s carefully: you should keep them professional and you should follow up with email notes afterwards about what you agreed.   You should keep all those emails, and you should also keep a running record with dates and brief notes, of your boss’s treatment of you.   These 1x1s are more likely to be hard to take, and you should if possible block off some time before hand to prepare, professionally and mentally, and some time afterwards to decompress.  Particularly if these 1x1s routinely make you angry, you should try not to go right from them to a key presentation or meeting, especially with a customer.

Whether you address the bias explicitly with your boss depends on a number of things: whether you believe your boss’s behavior is typical or atypical of your workplace, whether you believe doing so will put your job at risk, and whether you can afford to lose your job, how likely you are to be able to find another job in your organization or where you live, how discreetly you can conduct a search for another job, and whether you are locked into your job and for how long (for example, you are working on a graduate degree in a lab and must finish your research under that principal investigator, who is the problem).

Before you confront your boss, if you decide to, you should inform yourself about your organization’s policies are in this regard, if they have them. Larger organizations generally have such policies; small ones may not.  If you have a Human Resources department or staff, you should consult them about your situation.  You are entitled to expect those conversations to be kept confidential, but not everyone handles these situations well, particularly if the HR staff is junior or inexperienced with such issues.

Here are two other posts on the topic of 1x1s:  the post on how to have a good one, and the post on what to do after a bad 1×1 with a generally good boss.   If you don’t see an answer to your question about this topic in those two posts or in this one, you can email me at akrook@comcast.net or find me on Twitter @akrook.  For further reading on difficult people in workplaces I recommend both The No Asshole Rule and my own book, “Now What Do I Say?” Practical Workplace Advice for Younger Women, in paperback, ebook, and on iBooks.