• Alena Bennett

What your relationship with your boss says about you


What is your relationship with your boss like?

Pause. Shuffle in your seat (make sure they're not watching you read this). Fine, I guess. Move on and keep reading. 

Is it working for you?

I’m not trying to be inflammatory here, nor am I trying to suggest that your relationship with your boss is bad. In fact, I hope yours is great and high functioning. But it may not always be, and like all relationships, you may go through a bad patch. 

To follow on from last week’s introduction of the power base pie and the opportunity flow, I want to explore how you can set up your relationship with your boss so that it works for you.

Why does my relationship with my boss say anything about me?

Is what you might be thinking. And I get it, you probably think you performance should speak for itself. But like it or not, people have a view about you, they have a view about your boss, and they have a view about your relationship. From that information, they extrapolate a conclusion about things like (1) what you’re like to work with, (2) what you’re like to work for and (3) are you executive material? Why this is important to them (and why you need to be mindful of the conclusions drawn) is that they’re thinking, ‘what does this mean for me?’. 

Perception is reality. I’m sure we’ve all worked for a dysfunctional leadership team, where you observe the interpersonal relationships between the leaders and as a result you’ve had some pretty strong opinions about them as leaders and the level of performance they are capable (or incapable as it may) of achieving. I’ve certainly experienced it, have you? 

What does your CEO think about you? Are they thinking, ‘they are executive material’ or are they thinking, ‘who is that?’. Are you not even a blip on your radar? If it’s the latter, your relationship with your boss is failing you.  What do your business stakeholders think about you? That you and your boss are interchangeable and both of you support their business unit achieving their performance targets? Or do they need to wait for your boss’ approval or go ahead before they move forward on any work with you? Again, you’re not capitalising on your relationship with your boss.  What do your peers think about you? Do they think you’re the leader amongst the team, or do they see you as simply one of them? What would you rather be?

So what exactly do I mean by having your relationship with your boss ‘work for you’

I mean do you have a high functioning relationship with your boss? Does he or she send you to meetings in place of them? Do they actively give you opportunities for growth, help you establish new strategic, beneficial relationships? And by this, I don’t mean they put you on a project last minute to get through the grunt work. I mean do they actively take an interest in your career development and find opportunities for you to grow? At a very fundamental level, do you get on?

I had a client who worked for a boss who did all of those things. Her boss gave her new opportunities to increase the breadth of her role, and gave her the space to make it her own. He paid for her to have executive coaching so that she could work on her C-suite skills and ready herself to take the next step. And in the 12 months she worked for him, she really flourished and started operating at a C-suite level.

When you have a high functioning relationship with your boss, they value your contributions….and tell you. They don’t walk around the office without stopping by to say hello to you. They don’t take credit for the work you do, nor do they throw you under the bus. By contrast, in your regular 1:1 meetings, they ask whether there’s anything you need from them, they engage with and respond to your requests quickly and they communicate with you honestly. There is no question about where you stand with them. You get on and you produce quality work together.  

Experience says this is not always the case. So often I hear, “my boss probably doesn’t even know what I do”, “my boss is never around - I never see them”, “my boss always cancels my 1:1 meetings”, and even “my boss went around my back”. When I hear this, I know feelings of resentment, anxiety, resistance and a feeling of isolation exist in the relationship. These are not the characteristics of a high performing leader or team. There is no question in my mind, that when I hear these things, performance isn’t at its prime.

In the absence of intervention or guidance, this breeds further isolation and underperformance…in fact, it’s a bit like when you have an argument with your partner or family member and you find yourself walking on eggshells around them. The relationship is in need of help.

No one is to blame

Working with a boss when your relationship is fractured or non-existent is emotionally tiring. In fact, it can be exhausting. You’ll know this is you if you’ve come home from a day of work completely spent but not actually achieved that much, or worked that long a day. It’s easy to slip into victim mode and play the blame game. And venting is good. Persistent blame isn’t. It breeds toxicity and consequently underperformance. 

I was recently listening to one of my favourite podcasts by master life coach, Brooke Castillo. In this podcast she shared the concept of a ‘Want Match’. She did so in the context of a personal relationship context, and I want to break it down for you in a business context because I think there is valuable application. Simply put, when there is a want match, there is a match of wants. For example: I want to do strategic work, and my team want to do detailed work. Want match. I want to spend my time in collaborative workshops, you want to get on and do the work. Want match. I want to email you, and you want to read emails (as opposed to have a face to face meeting). Want match.

But….how many times do we go into a relationship - any relationship - and articulate our wants clearly to each other? Certainly not in a work relationship. For the most part, we don’t choose our bosses (very often we don’t choose our staff) and so it seems bold and bolshy to front up with your boss and share with them your list of what you want in a job. Even if you felt you could do that, you might not, because you’re so focused on delivery and getting to your next meeting. It feels indulgent and a ’nice to have’.

It’s not. Sharing your wants with your boss is the fastest way to gaining efficiencies (if efficiency is your goal). It’s also the fastest way to forming connection and cohesion which ultimately enhances quality. For senior finance leaders, quality is always a goal. Identifying these ‘wants’ and whether there is a ‘match’, or not, is the work we do with our clients using the Inventory of Work Attitudes and Motivators (iWAM) tool. In short, we find out what really floats your boat, and compare that to what really floats your boss’ boat. The gains are immediate and observable, when measured in terms of both productivity, quality and fulfilment.  When you know exactly why a tension or friction exists in any given relationship, you can address it in an objective, non-threatening way. Using a common language provided through the use of using a tool such as iWAM, enables you and your boss to modify your communication with and behaviour towards each other deliver better results. When you know exactly how your boss wants to consume information, you can deliver it to them in that way first time and reduce the back-and-forth. It will save you time. Reduce the frustration. When you know exactly how they think, and the filter in which they look at the world, you can cater for this when you preparing for meetings.No one is to blame. It’s just them. Different to us. And it’s okay.

What to do? The 4 steps to establishing a relationship with your boss that works for you


1. Awareness: What is your relationship with your boss like? How is it characterised? How is it perceived by others around you? What conclusions are others drawing about you as a result of their observations of your relationship with your boss?

2. Strategic thinking: What do you want your relationship to look like*? What outcomes do you want it to lead to? What opportunities do you want them to open up for you? What structures and systems around you can you leverage or invest in to get the most from your relationship with them?

3. Take Initiative: Do the work. Once you know what you want it to be, take the steps that you need in order to make it happen. Be proactive and make it easy to achieve your goal.

4. Speak up: You don’t ask, you don’t get. Have the conversation with your boss to make this happen for you. Share with others the work you’re doing to improve the relationship you have. The changes will be noticeable. When they notice you’re partnering with your boss, they’ll also want to partner with you.*You do not have to like your boss. But you do need to coexist in order to deliver high quality work. Do this by identifying a shared purpose or common goal that can bring you together with focus.

Your relationship doesn’t need to be ‘broken’ or ‘damaged’ to do this work

No, of course not. But remember: your relationship with your boss speaks volumes about you. It gives the CEO an indication about whether you're a valued member of the leadership team that can operate as peers with the other C-suite. It tells the executives whether you’re a follower or a leader. It indicates to your staff about who’s really in-charge of things: you or your boss. When it is damaged (and a fractured relationship is visible a mile off), it tells everyone around you your strength of character: are you a pushover or a victim, or are you a pragmatic leader of high integrity that will do what’s right?

I don’t think it’s right to put your head in the sand when your relationships aren’t working. Especially with your boss. 

Don’t find yourself playing a character in ‘Horrible Bosses - The Sequel’.


I invite you to shift your possibilities this year.

Amplify your Impact.


PS. If you think you may have some misalignment with your boss' wants, download this extremely simple want match diagnostic to see where you might need some help and identify the steps you can take to deliver success.  

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​© 2020 Alena Bennett Pty Ltd.

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