How To Get Your Boss Working For You: 3 Questions To Ask Your Boss To Get Ahead

The boss can be such an important ally in your pursuit of success, however you define that. But how do you convince them you are worth helping?

When I was serving my days in the trenches, in my 20s and 30s, it always seemed so hard to get the boss’ attention. Why don’t they notice my hard work? Why don’t they reward me for working my guts out? Why don’t they care about my career?

The questions I should have been asking myself is: Why should the boss care? Why should the boss help me?

It’s not until you actually become the boss that you realise the boss is just like anyone else – struggling day after day to keep everybody afloat and on track. It’s hard to find the time to ask employees what they’d like to achieve in their career or talk about how they can evolve.

Years later, when I was managing a billion dollar mining company, I noticed that the problems floating around my head were different to the problems that employees shared with me. Sometimes, the differences were exasperating. How was I ever going to get these people to understand my reality from their perspective?

So I started explaining to them what kept me awake at night, what was most critical to creating value in the company and where they stood in the process. I noticed that my teams started to listen very intently, asked great questions and always walked away from these conversations very keen to get on with their tasks. Their enthusiasm encouraged me to share as much as I could and we ended up discovering and building one of the largest open-cut nickel mines in the world in just under five years – a record speed for a mine that size.

How ironic that I’d been as frustrated as a subordinate that my boss didn’t understand me as I was as the boss that my subordinates didn’t understand. The answer seems so obvious in hindsight – asking the right questions.

My ideas on how to create value in my company didn’t come from a supernatural epiphany or even from creative genius; they came from asking questions of the company’s board of directors, major shareholders, stock brokers and other stakeholders. I saw my job as understanding what drove value from the perspective of all these people, forming a strategy and implementing it in the most effective way possible. Asking questions was a normal part of how I formed my strategy and it was clearly engaging for the company’s stakeholders.

Often, those that I spoke with said that discussing strategy and new possibilities was their favourite conversation. It’s true that there is something about a creative conversation that opens up the mind and lets a fresh breeze blow through. We walk away from these types of conversations feeling that we are in the right frame of mind and often I find myself thinking of new ideas that are completely unrelated to the discussion.

You can do the same thing to motivate your boss to help you by identifying their interests and showing them you care about and are working towards their interests. This one deed will hopefully translate to your boss realising that when they help you, it also helps them. And there is nothing in business as reliable as self-interest.

You do need to follow through though. It might even mean more work, but hopefully, it’ll mean more efficient work. Employees are not always aware of their boss’ highest priorities, either because the boss isn’t an accurate communicator, or due to a focus on the wider priorities of the business.

Taking the time to talk to your boss and making them feel comfortable enough to open up about their own goals and interests can help you pinpoint what your main focus should be on and identify other goals you could also work on, to specifically help your boss. It’s also a good opportunity for you to demonstrate your skills and value – since you’re at the coal-face, you might be better placed to identify and provide solutions to barriers hindering employees from achieving your boss’ goals.

The whole idea of this process is to create a dynamic where they can see your work is directly helping them, which predisposes them to help you out. This is obviously a better situation than you working your guts out to impress the boss, only for them to see this as just part of your job, which they therefore have no obligation to reciprocate.

While we’re always told to think of business as ‘not personal’, it’s actually really important that this process with your boss is a somewhat personal one. If they know you’re interested in their goals on a personal level, the dynamic you are trying to create will be more easily internalised by them, which means that it becomes second nature for them to see their interests and yours as intertwined.

To get the conversation going is the hardest part. Try asking your boss the following three questions:

  • What is keeping them up at night?

  • What is the most important thing they’re focused on to create value?

  • What are they focused on to make it happen?

Get the boss sharing these things and watch what happens next. If they take your queue, they’ll jump straight into the strategy of the company and open their mind to you.

If your boss is more suspicious or cynical, you might have to take a more surreptitious approach. Try dressing up the questions with context; for example, get the conversation going by talking about the mood around the office. While the boss might seem pretty glum talking about difficult business conditions, they’ll cheer up when you start asking about what might be possible to create value or to prepare for an uptick in business conditions. Or you can simply say that you want to make sure that you are directing your energies towards the most important goals your boss has right now.

Another way to begin the conversation is to share an example, such as a task you’ve recently done at work, which attracted a lot of positive attention. You could ask him if you received acknowledgement because it related to the bigger goals of the company.

Keep an open mind about where the boss takes the conversation. They might be too busy to answer right then and there, or you might have taken them by surprise. However, it’s rare for a manager to not appreciate these questions. Most likely, they’ll be keen to get right back to you, if not immediately available.

Allow them the space to open up by giving them time and actively listening. Here’s a clue: if you’re thinking about what to say next before they’re finished, chances are you’re not listening.

The boss might not have thought about the questions you’re asking and might even ask you some questions back like: “What do you mean?” or “Did you have something in mind?”

Let your boss know that you’re interested because you’re asking yourself similar questions about what you want to achieve: ‘Where are you now?’, ‘Where do you want to go?’ and ‘What are the three things you need to do to get there?’.

The funny thing is, people don’t care about how much you know until they know how much you care. By asking these questions you’re showing your boss how much you care about your work and the success of the company. If your boss isn’t interested in a conversation like that, it might be time to start questioning if you’re working in the right place.

Now that you have shown you are on your boss’ frequency and that you are open to discussions from their perspective, it’s rare that a manager won’t acknowledge how much they appreciate your support.

When you reinforce the idea that you’re working directly for the benefit of your boss, your boss just might start working for you.

Nick Poll is a professional mentor and is putting together an online magazine for aspiring CEOs and those who want to achieve their greatest potential. Contact details:


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