This is part 2 of the article “How to make your workplace a safe place for difficult conversations”

In a recent survey (HR Daily July 2021) one in three respondents stated they will not have a difficult workplace conversation, one in four will not deliver a difficult message about workplace change, and one in two will not give feedback to a more senior colleague – even though each of these conversations are considered highly worthwhile (87%, 84% and 71% respectively)

Of these three specific workplace conversations, giving feedback to a senior colleague is deemed as being most risky,” says Insium founder and director Dina Pozzo.


Types of conversations that are difficult:


       B. From an employee to manager (or someone more senior)

In healthy workplaces, good managers establish an environment that welcomes feedback and ideas. Even so, it can be nerve-wracking to suggest an idea that could be perceived as criticising your boss. Smart employees will make sure they have built good working relationships and established their own credibility as a strong contributor before they start suggesting better ways of doing things. One of the keys to any relationship working well is respect. Where lines of authority are involved, it is even more important to be respectful, even if leadership is lacking. Otherwise matters can become personal, and if contention develops, the employee will usually lose.


The kinds of conversations that can be awkward include:

  1. Asking questions about direction that is unclear. Asking good questions is the best way for someone who is not in authority to engage with direction that they do not understand. If direction is unclear to you or to your team, ask a question that helps everyone understand what the manager is trying to convey. If you do this in a respectful way, then it will only be the highly insecure managers who will react poorly.
  2. Making suggestions to improve a policy or procedure in a business. Depending on the dynamics of your work situation, if you want your idea to be heard, sometimes it is wise to ask if it okay to make a suggestion. If there is a lot of detail involved, it may be smart to write an email to your boss. Most managers will be glad you are thinking about your work but sometimes there are time pressures that mean they are not open to new ideas. It is best to ask good questions and make sure your idea will be helpful before you spend a lot of time or effort.
  3. Sharing why you think something is not working and why it needs to be changed. The best time to come up with creative ideas is when there are obvious problems being encountered. If you can see how to solve a problem your credibility will rise with your employer. Make sure you understand the issues, and then test your idea to your employer or a colleague with whom you have some trust. If you can get a few people to see the benefit of your idea, then it will more likely be adopted.
  4. Challenging a perception that has developed or a judgement call made by a manager. Sometimes a manager can adopt an attitude towards you that seems unfair. To react emotionally will usually not help you change a negative perception. It is better to seek to understand how they came to that assessment by seeking a meeting and asking clarifying questions. Once you understand why they have made their judgement, you can develop a plan to change their perception. This requires patience and discipline but will usually help you win.
  5. Asking for time off. The best planned person usually wins. If you organise your personal calendar so that you know 6 – 12 months in advance when you would like to take holidays, you will be able to submit your leave forms early. Usually, you will be granted the leave requested. If you ask on a whim with a week’s notice, you will probably get knocked back.
  6. Asking for more flexible work arrangements to help you better integrate personal life and work. If your workplace is still working out their post covid flexible work policies, it is a good time to be developing your case for the arrangements you prefer. Since your company is paying you, it is smart for you to be able to show how the arrangements you are seeking will not only help you but help the company achieve their goals. If you would like to be mostly based at home, you need to demonstrate that your productivity is better at home than at the office. The past two years have given you ample opportunity to show that. Companies are working out what they need. Many are going to trial various arrangements. The role of the office is being redeveloped. If you can contribute to that discussion in a positive way, it will likely help you get what you want as well. There is a shortage of skilled workers. Most employers are a little wary of making tough demands about work flexibility on their top performers, for fear of losing them. The better prepared you are about what you would ideally like, the better for all.


There are many other difficult conversations that an employee has with their manager. What other ones can you suggest?


INTEGRATE: Why Work Life Balance is a Myth | John Drury

Integrate: Why Work Life Balance is a Myth and what you really need to create a fulfilling lifestyle

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