To Tell or Not to Tell

May 11, 2023 8 Min Read
people, business, work, conversation between two people

Vector image is from by @gstudioimagen

Navigating Important Conversations with Your Boss: Approaching Work-Related Concerns Thoughtfully


There are many situations at work where you can wonder about the best time to talk to your boss about something that matters to you.

You may be thinking of leaving, feeling bored at work, wanting to explore a side hustle or wanting more flexibility with work. Whatever the context, you want to approach the conversation thoughtfully.

The approach you take depends on the nature of the relationship.

In my corporate days, I was ready for my next move within the organisation, and I wanted to be upfront with my boss about this. It turned out this wasn’t a good tactic. When I broached the subject, they responded, “That doesn’t work for me”, and then tried to block all my internal career moves.

In contrast, I worked with a person who knew, before he left corporate, that he would set up a consulting firm. Every spare minute he had, he used it to get ready. He set up his brand, website, value proposition, and infrastructure – everything he needed to leap into his new career. He did this whilst working full-time and keeping his work commitments ticking along, and his boss knew about it. In fact, his boss then hired him to do consulting work once he left corporate.

It’s a reminder that how the situation plays out depends on several primary factors – the nature of the relationship and your objective, as well as the context of the conversation.

Know the relationship

Whether you tell your boss depends on your relationship with them and whether you think they’ll support you or try sabotaging your efforts.

There is no right or wrong here. You must use your intuition, understand the relationship and work context, and be realistic about what could happen.

Crystallise your objectives

If you are going to tell your boss, be clear on what you want to say to them and what you are looking for from them. Is it to inform them, or do you need their support somehow? Also, consider how the news may impact them and how they may react.

It also helps to know your rights before you go into the conversation.

Understand the context

There are also specific considerations depending on the nature of the conversation. For example, the approach you use, if you are exiting, differs from a discussion about boredom at work.

To help you out, here are four situations and the different approaches you can take.

Situation 1: Planning your exit

If you are planning on leaving and there’s a potential for a conflict of interest or a potential concern that your new work may compete – even in a small way – with what you do currently, then be very careful about what you say and do.

In sales and roles involving intellectual property, employees are often given their marching orders as soon as they hint they are thinking of leaving.

Be prepared to be let go on the spot. Have everything you need in place, so if you are walked out, you only need to return to your desk and collect your personal items.

You want to preserve relationships as best you can. The old adage, ‘Don’t burn any bridges’, is critical.

There are also other factors to consider.

  • Choose the Right TimingFind when your boss is relatively free and not preoccupied with urgent matters. Consider scheduling a meeting to ensure you have their undivided attention and can have an open and honest discussion.
  • Prepare Your Thoughts: Before the conversation, organise your thoughts and prepare what you want to say. Clearly articulate your reasons for leaving, emphasising the positive aspects of your decision. Express gratitude for your opportunities while working with them and the organisation.
  • Be Professional and Respectful: Approach the conversation with a professional and respectful tone. Be constructive and future-focused rather than dwelling on any frustrations that may have led to your decision.
  • Offer a Transition Plan: Outline any pending projects or responsibilities you are currently handling and suggest ways to transfer them to a colleague or assist in finding a suitable replacement.
  • Written NoticeFollow up with a formal resignation letter or email after the conversation. Keep it brief and professional, stating your intention to leave, the date of your last day, and reiterating your appreciation for the opportunities you’ve had.

Situation 2: Starting a job on the side

Many people have jobs on the side. This may be because they want to explore opportunities, diversify their income streams, earn more money or develop new skills.

If you plan on setting up a job on the side, often known as a ‘side hustle’ or ‘moonlighting’, ensure all work connected with that second gig is done using your equipment and technology. Have a separate laptop, mobile phone and all the infrastructure you need to set yourself up.

Some organisations have strict guidelines that prohibit or restrict employees from engaging in outside work, especially if it creates conflicts of interest or affects job performance. Depending on your employment contract, you could be in a sticky situation if it’s not handled correctly. This means it’s crucial to read all your employment documentation – even the small print you might typically ignore. Know what your rights are and what they aren’t. You may need to get written consent from your employer to get involved in outside work.

There are also several other factors to consider.

  • Reflect on Your Motivations: Before approaching your boss, take the time to reflect on your motivations for pursuing a side hustle or additional job. Is it to fulfil a passion, gain new skills, or supplement your income? Understanding your objectives will help you articulate your reasons effectively and demonstrate that your side endeavour will not compromise your commitment to your current role.
  • Consider Time Impacts: Assess the impact on your current workload and ensure the second job will not interfere with your primary job responsibilities. Assure your boss that you are aware of the potential challenges, are committed and are willing to potentially adjust as necessary to maintain a healthy work-life balance and ensure the smooth functioning of both positions.
  • Communicate Openly and TransparentlyBe clear about your intentions, explaining how this additional work won’t interfere with your performance, commitment, or availability.
  • Discuss Potential BenefitsHighlight the benefits this brings to your current role. Consider how the skills or experiences gained from your additional work can contribute to your performance, complement your professional growth or offer new insights.
  • Confidentiality and Conflict of Interest: Address any potential concerns regarding confidentiality or conflicts of interest. Emphasise how you will maintain strict confidentiality and adhere to company policies, ensuring that your outside activities do not compromise sensitive information or cause conflicts of interest.

Discover : How To Navigate Difficult Conversations 

Situation 3: Wanting more flexibility

Many of us are now used to working from home and see it as a ‘right’, not a ‘privilege’. Some senior leaders are now mandating senior employees come back into the office on a full-time basis. In contrast, some European companies and parliaments are enshrining work from home as a legal right.

But flexibility isn’t just about where you work. It’s also about the hours you work and how you work.

So how do you approach the conversation with your boss around flexibility? Bearing in mind the earlier commentary, here are additional considerations.

  • Reflect on Your Needs: Consider your personal circumstances, such as family commitments or health reasons, or your need to balance other interests. Clarifying your objectives helps you articulate your reasons effectively.
  • Research Company and Organisational Policies: Know the organisation’s policies regarding flexible work arrangements. There are rules, but there are often exceptions to the rules too. So be ready with examples of what other people are doing.
  • Timing is Key: Avoid approaching the topic during busy periods or when the team is under significant stress. A calm and focused environment will contribute to a more productive discussion.
  • Prepare your caseA well-thought-out proposal outlining the benefits of what you are seeking is crucial. For example, if you want to go part-time, consider how reduced hours will impact your current workload, responsibilities and the team. Offer potential solutions and highlight the potential benefits, such as increased efficiency, improved work-life balance, and the retention of valuable skills and experience within the organisation. You want to demonstrate the value a flexible arrangement can bring you, your boss and the organisation.
  • Consider your leverageThese conversations are often more straightforward when you are clear on the value you bring to the organisation, and those skills are in high demand. So, know your points of leverage.
  • Communicate Clearly and ProfessionallyClearly articulate your needs, highlight the benefits you bring and be prepared to address any concerns your boss may have about the impact on team dynamics or productivity.
  • Provide a Trial PeriodDepending on the situation, you may offer a trial period that allows the opportunity to assess the feasibility and effectiveness of the new approach while allowing for adjustments if needed.
  • It’s a negotiation: Be open to negotiation and compromise during the conversation. Approaching the discussion with flexibility and willingness to find common ground increases the chance that you’ll reach a favourable outcome.

Read also: How To Have a Courageous Conversation With Your Boss?

Situation 4: Bored and looking for more

Simply turning up and telling your boss ‘you’re bored’ isn’t likely to deliver the outcome you want.

You want the conversation to be positioned positively and productively because this is an excellent opportunity to highlight to your boss that you want to contribute more and can see other ways to add value.

  • Self-ReflectionReflect on why you are bored. Is it a lack of challenging tasks, insufficient opportunities for growth, or a mismatch between your skills and the role? Understanding the root cause will help you articulate your concerns effectively.
  • Gather EvidenceHave evidence that demonstrates your progress and value. Identify specific instances where you can contribute more, feel your skills could be more utilised or have outgrown the role.
  • Frame it ConstructivelyAvoid blaming others or criticising the organisation. Instead, focus on your desire for growth and your commitment to contributing meaningfully. Frame your concerns as an opportunity for personal and professional development rather than a complaint. Emphasise that you’d like to broaden your experience and are looking for ways to do more.
  • Offer Potential SolutionsCome prepared with potential solutions. Propose projects or tasks that align with your skills and interests. There may be upcoming projects or initiatives you could get involved with.
  • Be Proactive: Expressing your willingness to take on additional responsibilities or explore new projects within your current role, demonstrates your commitment to finding solutions within the existing framework.

Of course, the list of conversation topics isn’t exhaustive. There are plenty of other conversations that can be challenging. For example, requesting a pay rise, addressing workload issues, providing feedback and raising sensitive topics such as bullying, harassment and marginalisation. In all situations, remember if you don’t raise the issue, nothing is likely to change, and while having the conversation can feel challenging, and even risky, it’s important to stand up and back yourself.

Republished with courtesy from

This article is also available in Chinese.

Edited by: Kiran Tuljaram

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Michelle Gibbings is a workplace expert and the award-winning author of three books. Her latest book is 'Bad Boss: What to do if you work for one, manage one or are one'.


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