You can listen to this episode, or read the contents below.


Bottom line of this article:

If you want your boss to listen to what you have to say, and buy in to your idea or recommendation, you need to think about the subject through their eyes.  Tap into what is important to them and how they like to receive information, and then present things in a clear, precise way that gives enough but not too much info.  You need to take the time to do this, even if for you all the advantages and reasons are perfectly clear.

Remember – you cannot control the outcome of the conversation with your boss – because that relies on what someone else does or says.  You cannot control someone else’s actions or thoughts.

But, you can control what you do or say – and you can do all you can to line yourself up for success.

This episode with give you three key questions to think about before you see your boss in order to help you do this.


When you go speak to your boss and propose something to him or her – do you ever feel like you are not being heard?  They have their own agenda, things that are important to them – and this is not one of them.

Maybe it’s a new idea about how to process invoices, or a technical interpretation of a new service being offered by your client, maybe it’s during your yearly review and you want to ask for a pay rise.

But no matter what you say or do, they either simply don’t have time to listen to what you have to say, or they don’t seem to get how important the recommendation is.

So instead of listening, they just shut you down.

It’s frustrating as hell – I know.  Been there.

Oh, so many times.

I even remember one boss in particular for whom the answer was always going to be no – so long as it was someone else’s idea.  But then a couple of days later he would appear from his room with this amazing idea that he wanted to tell everyone about … an idea that was remarkably identical to the one I had been talking about … though of course, that might just have been my imagination.

Anyways …

I had to learn to navigate all this – and find a way to be heard.

A big part of that was to really see the recommendation or idea through the eyes of my boss, and make sure that when I presented it, I knew the buttons to push to maximise my chances of success.

Perhaps you have a similar situation you want to think about, and it that is the case this article is for you.

You cannot control how your boss will react to what you have to say – but you can control how you say it.

And so this article sets out three questions to ask yourself before you go into that meeting.  These questions will be relevant for your boss, but also if you are making recommendations to a client, or to the Board …

The questions are the following, and I will take each in turn:

  • Where does this recommendation fall into the bigger picture?
  • What is important to your boss?
  • What are likely questions or objections and how will you handle them?



Where does this recommendation fall into the bigger picture?

The first thing you need to remember is that this recommendation that you are making to your boss is not in a vacuum.  Your boss is going to do something with this, be it make a decision based on what you have told him, or pass the information up the chain to someone else to make the decision.

It is important to understand which case you are in, as this will impact the information that you need to present.  For example, if your boss will pass things up the chain, he may need to know more about the background to the case so that he can answer any questions that he might get.

Another thing to think about in terms of the bigger picture is to see where the recommendation fits into the overall strategy of the firm. If you can identify that, and can show how the recommendation will help everyone fulfill those strategic elements this will really help your case.

Do you know what the strategic priorities are for your firm?  If not, how could you find out?

To help in that reflection, think about these aspects:

  • Money – the firm will likely want to drive up revenue and drive down costs
  • Market – drive up market share, drive down time to market
  • Risk and reputation – drive up retention of staff and clients, reduce risk

Think about the recommendation, and see how it helps your boss achieve those strategic outcomes.  After all, if you can make him or her look good, that is bound to be a good result.


What else is important to your boss?

Over and above the strategic elements for the business, what else keeps your boss awake at night?   What are his or her own objectives and goals?  Tap into these and show them how your recommendation will help them achieve these, and this will set you up to succeed too.

Think too about how they like to consume information.  Do they like to receive something written that they can then go through in detail at their leisure?  Or do they prefer to receive things in a visual way and see the visual connections?  Maybe they are happy that you just come see them and chat things through.

Tapping into their way of consuming information will mean that you don’t have any surprises – like prepping a slide deck for hours for them just to say “give me the bottom line”, or alternatively for you to rock up with a couple of talking points and them to ask for all the background and support material.

I have found with these situations that it is a little bit like sitting an exam at school or uni – the content is about 5% of the answer – but the way you answer is the other 95%.  Get the exam technique right, you are home and dry even if the final answer is not right.  Present the information in a way that your boss prefers to get the information, and that’s really going to help.



What are potential questions or objections that your boss will have, and how will you deal with those?

Come on, you know your stuff, and you also know how your boss thinks about things.  Think about what they might likely object to, or areas where there could be questions.  Think about questions you yourself had when you were thinking through this idea, or think about instances where you might have talked to others about it – and work out how you might handle those questions or objections if they came up.

Think also about the Critical Information Requirements for your boss.  What are the things that they must absolutely know about – elements without which the entire scenario changes.  From my old VAT days an example of critical information regarding a recommendation about costs and where to put them would be the VAT recovery right of the company receiving those costs.  That’s a VAT techie example, but I am sure that in your industry or field there will be equivalents.

If you are having problems identifying these elements, who would be the best people to help you with that reflection?  It might be your boss directly – you could proactively speak to him or her, tell them that you are going to come present something to them, and ask how you could make it an easy yes.  If that’s a no go, who would be other allies who can help you answer similar questions?



So, there you go for three questions to think about before you make a recommendation to your boss.

  • Where does this recommendation fall into the bigger picture?
  • What is important to your boss?
  • What are likely questions or objections and how will you handle them?

If you go away with nothing else, let it be this:

It might be completely clear why you want to make this recommendation, but if you don’t manage to get this across to your boss, you will be lost.

You have got to put yourself into the shoes of your boss, and see things through their eyes so that you can identify what is so important from their perspective.  Make it your objective to craft that recommendation in the best possible way, and put all chances of success on your side.


Let me know what your experience is – do these questions resonate for you?  How could you use them in your own situation?