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Managing up: two key skills you need to “teach” your boss

Managing up: two key skills you need to “teach” your boss

I once had a boss who managed all of his senior managers through an online performance management system because he was unable to speak to us directly about our accountability.

In one to one meetings, I could never get a word in about what was going on in my team, good or bad. He would talk non-stop for the whole hour. I knew enough about his wife and kids that I’m sure they would be mortified. But we would never talk about the work.

All of us staff had to spend inordinate amounts of time filling in his electronic system that was neither fit for purpose nor useful in its practice. We had all eventually learned to game the system so that we spent as little time as possible entering information so that it wouldn’t send red flags to the boss.

What came out in the end was that the team leader with the most seniority among us was failing badly, but this new CEO didn’t have the guts to confront him on his poor outcomes. So he enforced this meaningless, onerous system on all of us to provide him with red-amber-green ratings against our objectives.

It did nothing to help him solve his problem with his renegade manager, it cost thousands of pounds, and it damaged his relationships with the rest of us. He lost our respect, and he had no idea how any of us were actually performing.

This kind of fearful and weak leadership undermines organisations and cheats professionals of all kinds out of good career development.

If you have a leader like this, acting out of fear or insecurity, overcoming it can seem impossible. It can make you hate a job you once loved, or feel like you are no longer growing and developing in your role because you are not getting any guidance.

It may help to understand what is behind the behaviour. Have they been promoted beyond their abilities? Is it their first leadership role? Are they younger than the people they manage? Trying to understand the underlying factors may help with dealing with its manifestation. Not only will you be able to sympathise with the person, but it can give you insight into how you can support them, and “manage up” to try and make the situation better.

Regardless of the ‘why’ (because of course they may just be jerks), there are two key skills you can “teach” your boss to help change this way of behaving:

1) How to listen to the team

2) How to feel secure enough to be transparent with the team.

Here’s why, and how

When the boss listens instead of talking they no longer have to appear to know it all, which helps them with their feelings of being a fraud. Being transparent means that they don’t have to hide problems, insecurities, or their own weaknesses from the team. They can begin to trust that their team are there to support them as much as they are them, which leads to stronger relationships so that you can get more open in your conversations. It becomes a virtuous circle.


You can be quite frank with your boss in your next one to one or conversation. Start by saying that you want to share your progress or risks with them. Let them know that by being able to do much more of the talking, you will find these sessions more useful, and would value their reflections on what you share. If you think they are covering up insecurities, acknowledge that the problems or issues you are having may not have ready answers, but that you think that just sounding them out together may help.

They won’t have to know the detail of your work at this point, so they won’t need to bluster or blag their way through the conversation. As you present overviews of your work during each one to one session, they will become familiar with what you do and the challenges you face, as well as what you are doing well.

This takes no bravery from them and actually takes the pressure off of them. This begins to raise their confidence levels and they become more useful as a leader.

They will come to realise that most people are trying to do a good job and want to share with them the work they are proud of. They should see the value of talking less and listening more, and become better at it.


Being open and honest about what is not going well, what you are unsure of, and where you see risks perpetuates this transparency in others. Sharing these things with your boss can help them relax and not feel as though they can’t show any signs of doubt, or weakness, or insecurity.

It gets all problems out on the table, and it takes the power out of them as scary issues that should be kept hidden. Tackling these breeds confidence and an understanding that dealing with things openly and together greatly reduces their impact.

Conversations between the boss and the team start to fulfil their real purpose of providing a safe and supportive environment for professional development. You begin to learn from each other, and find each other supportive allies in the work that your team strives to do together.

Be the brave one and go first- start to open up about things you are dealing with in your work that are a bit uncomfortable or scary to share. Unless you have a truly poor boss who shouldn’t be in a leadership position at all, this should open them up to do the same.

It’s not always easy to influence a boss’s behaviour, especially if they are just pigheaded or inherently bad leaders. But ‘managing up’ and teaching your boss these two basic skills can help you create a more plugged in and useful leader. It helps you build a better relationship and improves your own quality of experience at work.

My first book, Becoming a Fearless Leader: A simple guide to taking control and building happy, productive, highly-performing teams is out now. You can find access to a free pdf workbook that accompanies it on my website. If you do read my book, I would love to hear your comments.

I write about how I became the founder of a tech startup as a non-techie, over-40 female with no entrepreneurial experience, and all I am learning along the way. You can see more here. If you think this might be helpful for others on their entrepreneurial journey, please recommend and share.