Have you ever had an uncomfortable or critical situation, either work-related or personal that you needed to inform your boss about?

How do you feel about taking your boss aside and asking for something you need?

You may feel scared to approach your boss because you’re just starting out in your career and you’re not sure how to communicate what you want to them. You may wonder, my boss looks so busy, how can I get their time and make the best of that time with them. Or perhaps you have a boss who is unapproachable, lacks empathy, or is quick-tempered. Whatever the situation might be, everybody wants their boss to be on their side as they can help you grow in your career. If you can build an open and positive relationship with your boss, you’re more likely to be involved and exposed into exciting situations at work, and less likely to face negative consequences if things don’t go well.

We have worked with bosses for a few years and have learned what makes them tick. Here are our five tips to yield positive results and a resolution to your communication worries.

Be solution-oriented

  • Ask yourself, is this really something I need to approach my boss about? If you can solve the issue on your own or with your colleagues’ help, then do so. Bosses are busy and if it’s an issue you can handle, don’t waste their time. Asking for your boss’s help on a matter you’re able to solve yourself can make you come across as being incompetent, and you want to avoid that.
  • If it’s an issue you have to approach your boss about, then come up with a few possible solutions on your own and present them to your boss. This will make their job easier. By coming up with your own solutions, you will make a good impression as you’re portraying that you are a problem solver, you have strong ownership, and you are responsible.

Prepare what you’re going to say before you say it.

  • If you’re nervous and not able articulate your thoughts coherently, your boss may get confused and will not understand your situation well. Bosses are busy, and you need to make the best of your few minutes with them. Write down what you need to say with your proposed solutions. Start with the big picture, give necessary details and end with a clear request. You should also write down their feedback to avoid any confusion later on.
  • If you’re making a request that you worry your boss may not be receptive to, then think of what concerns they may have. Can you address their concerns already in your request?

Seek extra support for the unapproachable bossafrica-anger-animal-55814

  • If you’re truly uncomfortable with approaching your boss, perhaps because you feel that they are not empathetic and understanding in their nature, then consider tagging someone along who you feel comfortable with. This person’s presence alone can help you gain that extra boost of confidence you need in order to approach your boss.
  • Ask your colleagues about their approach when they communicate with the boss – what do they do that works? If you’re new, this is especially helpful as your colleagues have become accustomed to your boss’s nature and may have some useful tips that can help you.

Timing is everything

  • Never wait until the last minute when the situation is critical. Approach your boss ahead of time with the matter to avoid surprising them and causing them unnecessary pressure and stress. Most bosses appreciate a heads-up of a potentially critical situation, especially if you tell them how you’re handling it.
  • With a personal matter, you want your boss to pay attention right? Ask the boss when they’re available in advance to ensure they have time for you, and specify that it’s a personal matter and how much of their time you may need.

  afraid-1299617_1280Just do it

  • Having hard conversations at work is necessary, just muster up the courage and do it. We promise, it gets easier with time so just keep practising and hang in there!


Practising your communication skills is necessary to strengthen relationships in the workplace and make them as constructive as possible. We hope our tips will help you out, and if you try them out with your boss, let us know how it went! If you are a boss yourself, would you add anything to the list? Do you disagree with any of the tips given? Let us know!

If you want to replace worry and blame in your career with new skills and awareness to be in charge of making your dreams come true, then join our career happiness coaching programme. Email Martha at martha@edgeperformance.co.ke to find out more. Also, subscribe to our newsletter for recent updates on exciting new roles, office updates, talent trends, and to read our feature blog post.