I’ve been writing a series of posts on management based on my experiences. If you’re starting with this one, you may want to have a look at: https://www.jlgoodwin.com/words-pictures/2020/9/17/management-the-job-of-a-manager

Introduction

Sooner or later every manager ends up in a situation where they need to get their boss to do something and directly asking them isn’t going to work. This is what “managing up” is. Of course, it is always best if you never have to do it; ideally your boss is doing their job well and you are in alignment with them on what your team is doing and how it is performing and on the overall goals of the organization. The first alternative is to try the direct approach and give your boss the chance to do the right thing or give you a different approach to use. But, because humans are flawed, organizations are a bit fucked, and you don’t often get to recruit and hire your boss, you’ll eventually have to try managing up.

When to manage up

My boss was promoted into a role that was way beyond their experience level due to friendship and nostalgia for the early days of the company. They realized that they were completely over their head and that in reality, I was both their most experienced direct report and more qualified for their role than they were. I wasn’t interested in their new role, and I wasn’t jealous. I offered to help in any way I could. Instead of accepting my offer of help and trusting me, they decided they needed to tell me how to organize my team, manage my directs, and run certain key projects. This was mostly so that I would “respect” them. After a while, I stopped trying to clue them in to where they were failing and instead I did the nonsense things they asked for and minimally complied. While never openly opposing their processes, I demonstrated better processes on my team that my other peers noticed and began to copy. I followed my own direction with my team and we succeeded more and more. The contrast wasn’t flattering vs. my boss’ other failing teams, which took up most of my boss’ time. Eventually my boss stopped meddling in my team and was heard to point to us as an example of a successful team.

In many cases, managing up isn’t worth it. If you look at the entire operation of your organization and your company and it’s a chaotic failing mess (and there is no obvious path to a good upside for you), then you should focus on finding a new job and just surviving this one in the meantime. However, if your boss is an anomaly in an otherwise good organization, then it is probably worth managing them a bit. I can’t emphasize it enough that you don’t want to take over your boss’ entire job in the process; many are lazy and incompetent enough to accept the offered scapegoat. You only want to manage them relative to your goals and your team's goals and succeeding for the company.

Some signs that it is time to manage up may include a situation where your manager commits your team to deadlines and deliverables without speaking with you or the team. You end up in a review meeting with your boss’ boss and find out that you’ve failed at a goal you either never heard of or were told wasn’t high priority. Or your team is regularly disrupted by “last minute” projects that seem to come from nowhere. Or you are constantly asked to take on more work and to get your team to “work harder/faster” without any clear explanation of why and no offer of more humans to do the work.

Some techniques

I was the Software Architect for the team and nobody reported to me. The problem was that while I could design the software system to my heart’s content, the team seemed incapable of making progress on implementing it and putting it into production. The manager of the team was a major contributor to the problem: They were a “yes” person and agreed to everything they were asked. Sprints were packed to the gills with all kinds of tasks that had little to do with the platform we were supposed to be building. At the same time, much of the team’s time was spent fire-fighting an existing system that was critical to the business and riddled with technical debt, major design flaws, and single points of failure. The manager never focused any effort on root cause analysis or technical debt reduction, only on random tasks, which also didn’t get done because of the fire-fighting blowing up the sprints. Eventually, my boss’ boss called me in to castigate me for not fixing these problems. I was genuinely perplexed: I was hired to deliver an architecture for a new platform, not fix the team. After a heated discussion, I agreed to fix it, but only if I was given a completely free hand. I then engaged in a detailed root-cause analysis that didn’t stop at just the technical issues, but examined the process and management problems that let the production issues persist, thereby putting the business at risk. I hijacked the whole team and we fixed the major issues in the existing platform. It became clear that the manager was one of the major root causes, since the same team that couldn’t get anything done before was immediately very effective. I ended up managing the team temporarily and helped them recruit a much better manager.

You want all of your efforts to be perceived as positive and supportive of your boss. Arguing with them about their mistaken ideas is largely a waste of time; often they are insecure, attempting to cover their failures by acting the way they think confident people act. Always listen to them, always show them that you’ve heard them completely, always try to minimally comply with any stupid stuff they want. I propose a process that a former manager of mine dubbed “parallel monologue” where instead of trying to refute your manager’s position or argue with it, you merely acknowledge it and then add your ideas. Often you can just tell other team members and peers your idea and after a while you’ll find these ideas making their way to your boss.

Find out what your boss’ goals are supposed to be from their boss, from sales, from marketing, from support. Find out what the business actually needs your team to do. After listening to your boss, start a parallel monologue with them about what you’ve learned matters to the business. Not in opposition to them, but in addition to them. If they resist, accept it and say thanks for the guidance. Assign people to the real goals, even if it is part time. Seek opportunities to show your boss’ boss that you and your team understand what the real priorities are. Share all the credit with your boss to gain credibility and leverage with your boss’ boss.

When you know your team is going to be disrupted, say “Yes, Boss!” Then, very positively say, “I’m just going to let folks know that we’re not going to be able to work on [the true high priority] so they can replan.” If they demand that you keep the information to yourself, you should make sure to reiterate your suggestion that folks be notified in an e-mail or status report, and note that you’ve followed their guidance and are grateful for it. If they’re starting to see the benefits of your parallel monologue, they may at this point start to reconsider disrupting the team and your team cadence and productivity can improve.

Develop a relationship with your boss’ boss (or even higher up) and talk to them about how wonderful your team is. If they ask you direct questions one on one about your boss, be honest, note all of their positive attributes first, then explain how you’re often surprised by their actions that cause your team to fail. Repeat your parallel monologue on how you think things could be better, showing that you know what the business needs from your team.

Through everything, keep up the parallel monologue with your boss, agree with them, then say “and,” followed by your thoughts on what to do. Make sure to do this one on one. For many of them, once they see positive results from your team, you will hear your words coming out of their mouth. Don’t note this, don’t take credit, just keep up the parallel monologue and keep focusing your team more and more on the real business goals of the company.

Replacing your boss

One result of processes like this is that your team will start to look like a bright shining star in an otherwise murky sky. Folks will begin to wonder why the rest of your boss’ organization sucks so bad and yours is doing so well. Depending on the level of incompetence in the upper management of your particular company, they will eventually do the math and want to replace your boss. You don’t need to be that person if you don’t want to, even if they offer it to you. Only do it or ask for it if you feel ready and actually want to. But otherwise, you must work to get involved in recruiting your new boss, up to and including volunteering to run the recruiting process. This will give you the best opportunity to get someone into that position who will be good for you and your team. Yes, it will be a lot of work. Yes, it will be worth it.

Have you been “managed up”?

Recognizing when one of your team members is trying to manage up can be informative and a signal that perhaps you’re messing up. Being far from perfect, I’ve had the epiphany several times “Heeeeeyyyy, they’re using my techniques on meeeeee!”  After some introspection I usually own up to my blunder, ask them to take charge of the process they’re trying to manage me into, and praise them for taking initiative. In some cases, it isn’t so positive, often when it is a  purely self-serving move on the team member’s part. I’ve had managers try to get me to do their presentations for them, deal with the performance problems on their team, fire people for them, even get rid of peers they think are competing with them. These sorts of things don’t make me inclined to trust, promote or empower someone. In fact, I usually give them a lot more direction, deliverables, and scrutiny to see if they’re doing any of their job right. Sometimes you can provoke some “managing up” from your direct reports, when I see all my direct reports playing chicken with a task that needs to be done with the team, I have been guilty of proposing a heavy “brute force” process in order to provoke someone into volunteering. The clever ones will try to “improve” my process for me and then I have my volunteer. 

Losing your job

Sometimes your boss will see your efforts as a threat no matter how positive your actions are. This is why documenting your compliance with their wishes, your extra efforts for the company, and your advice to them (which they ignored), is good insurance. But you should always be prepared to get fired. If possible, keep your finances in good shape, keep your resume up to date, and make a list of some peers or stakeholders who can give you good references. I’ve never been fired, but I have been threatened with it several times for doing my job and making my boss or an executive above them feel uncomfortable as I did it. The discomfort usually comes from them getting information inside their executive cocoon that most people are trying very hard to keep out of there. The thing that has saved me every time was being more valuable to the company than my boss or the comfort of the particular executive. If you’re going to have a dispute with HR involved and all of that, you want to be doing it from the moral high ground with good documentation.

What does success look like?

In the best case, your boss will realize that you are acting in their best interest. They will start treating you like a valued collaborator and confidant. Or, you’ll get a new boss, one that you helped to hire, and they already like you and trust you because you got them a new job.