By Telana Simpson

The dynamics between us and authority figures, and our views on those in positions of power, contribute significantly to the way we engage in difficult conversations with them.

They are, after all, still human beings like us, as fallible as the next person. Yet they play a different role, and that role often has the ability to influence our life considerably.

This fact though shouldn’t stop us from having conversations that count with them, and especially when the issue or outcome of that conversation impacts our quality of life.

To have a vigorous conversation with your Manager at work, here are a few pointers to keep in mind, and to open the way for a more mutually beneficial outcome.

Scenario: Unfair situation at Work

The scene is in your workplace. You love your job and are prepared to make some sacrifices to get ahead, within reason though. Balance is also a value, and you strive to work hard, and then play hard on the weekends. Outside of work hours is your time to catch up with your family and friends, and keep some sense of work/life balance.

Yet your boss has this bad habit of giving you crucial and apparently urgent assignments last thing in the day, or just as you’ve about to leave on a Friday afternoon.

So you’re spending more time with your laptop than quality time with your family, and it’s becoming an embarrassing broken record of having to cancel social engagements, usually at the last minute.

So how do you go about bringing up this unfair situation at work with your boss, knowing the delicacy of the matter and the challenges this could create for your relationships at work, if it’s not well received?

How to have a difficult conversation with your Boss

As always, make sure you have done the groundwork for having difficult conversations.

Set the Scene:

Ask your Manager when you could talk to him/her, setting the agenda as being to discuss the timing of receiving your assignments. Book a private meeting room for the discussion, rather than your boss’s office, so that it’s in neutral turf. Alternatively, if you feel a more casual tone would be appropriate, suggest you have a coffee in the cafeteria to have this discussion.

Remember, you want to give the person a heads up on the topic to be discussed, so that they have time to prepare, and so that you can keep on topic for the meeting, and not get sidetracked with whatever has come up during that day.


To start off the conversation, you want to affirm where you stand, and also seek out understanding of where your manager stands, before you jump to any conclusions or can problem solve effectively.

So start off by making these types of points, ensuring they are authentic to you and your situation:

  • Let your boss know that you want to do your best but feel that the quality of your work might start to be jeopardised if you keep getting the assignments so late in the day or week.
  • By getting an assignment at 5:00 or late on a Friday afternoon, it cuts into your time you’ve scheduled to be with your family, and you’ve noticed that you are starting to feel resentful of the lack of balance. Your work is not your best as you are not getting enough time to work on it, or to rest and be with your family to recharge for work.
  • Then ask him/her what is going on that the assignments are always “life or death” at the last minute, as the understanding might help you manage your perspective.


These would be the areas to avoid, and the pitfalls to not get yourself trapped in:

  • Don’t refuse to do the work – rather negotiate on the timing of when the work will be due, even if you get given the assignment late in the day.
  • Don’t accuse your boss of being disorganised, lazy, or unable to manage his/her time. Rather focus on explaining the impact of the timing of receiving the task, and what you suggest might be a more useful strategy.
  • Don’t complain about overtimes. Rather clarify the criteria for urgent work that requires overtime, as not all work is truly that pressing that it cannot be started first thing the next morning.

Difficult conversations shouldn’t damage your career

If you’ve worked on your own views of confrontation, and are continuously building rapport with your superiors and developing your relationships at work, having a conversation that counts with your boss will lead to more productivity and understanding between the two of you.

So focus your points in the conversation on wanting to deliver high quality work on time. And don’t be scared to negotiate the deadlines. If we don’t ask, the answer is 100% no.

Remember also that we teach people how to treat us. So if we don’t ask for reasonableness, we’re much less likely to get it or to be treated reasonably.

Also asking your boss how you can help him/her more, so that there can be less of the last minute assignments given so late, will go a long way towards you coming across more as proactive and willing to collaborate.

Having this kind of attitude, rather than a blaming or defending one, opens up discussion and encourages problem solving.

As Henry Ford said,

Don’t find fault. Find a remedy.”

Be real,


About the Author:

Our Coach, Telana SimpsonTelana is a dynamic, transformational Personal Coach and Blogger who specializes in communicating and relating.  She helps people have no regrets in life by having conversations that count.   Follow her on Twitter or her podcast show, Let’s Talk Communication.