Insightful takes on scaling your business

How to disagree with your boss without losing your cool… or job

how to speak up and disagree with boss
Yessi Bello Perez
Story by
Yessi Bello Perez

Senior Writer, Growth QuartersYessi leads the writing efforts at TNW’s Growth Quarters. Yessi leads the writing efforts at TNW’s Growth Quarters.

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Over the years I’ve learned that it’s absolutely fine to disagree with your boss — as long as you know when to speak up and how to do it. Remember: It’s not about what you say, but how you say it. 

This wasn’t always the case though. When I first started working, I thought it was better to keep my opinions to myself — even if I felt that my manager was wrong, or didn’t have all the necessary information to make a decision. 

I’ve also — as I’m sure you have too —  witnessed several heated discussions between colleagues and team leaders, and given that I don’t like conflict, this has made me even more uncomfortable and anxious to speak up in the past. 

[Read: Most mobile apps suck — here’s how to fix them]

It doesn’t have to be this way though. You can totally express your opinion to your boss or manager without losing your cool.

These are some of the scenarios where speaking up would be justified:

  • If you feel very strongly about something. For example, if you have significant concerns about over-promising on a project or its delivery date. Another good example would be to open up about a current situation. One scenario is being understaffed, and it’s affecting morale and performance.
  • When your expertise or experience can add value to the conversation. If you’re working on a project that’s closely tied to what you’ve done in the past, you have every right to share your insights and learnings with your boss and the rest of the team.
  • If you have relevant information that could directly impact a business outcome, you have every right to speak up and share this with your manager.
  • If you’re concerned about a specific activity, or activities, being unsafe, unethical, or illegal. This can be a difficult scenario to navigate so make sure you treat the subject with the consideration and caution it requires.

Timing and context are key and you’ll need to pick your battles. Think about how high the stakes are. If they’re low, you might want to save your energy for another time. 

The biggest mistake people make when they speak up is that they fail to take into account several factors that could have a huge impact on how the conversation unfolds.

As you know, timing and context are key, but it’s also important to read the room. If your boss is having a particularly stressful day or week, you should consider holding off until things calm down. 

It can be hard to hold off from speaking up but it’s almost always worth it — say the ‘wrong’ thing at the wrong time and you’ll likely end up feeling frustrated and deflated. Just choose your moment. 

How to communicate your grievances

The tone is vital. You need to remember that you’re not looking to spark conflict; the conversation doesn’t need to be adversarial and you need to do everything in your power to ensure you’re collaborative and communicative.

You need to appear confident, but not defensive. You need to strike the balance between speaking with authority — almost matter of factly — and coming across too strong. Take all emotion out of the equation and focus on the facts: what the problem is. 

It’s always advisable to think about the conversation in your head before you approach your boss. Outline the problem and try and come up with several solutions — this way you’ll come across as a problem solver and not a conflict instigator.

Instead of saying “I don’t agree,” saying something like “If we took that direction, I’d be concerned about X,” or “My experience has been a little different. Would it be OK if I shared some my learnings and concerns?”

Ask questions, but don’t put your boss on the spot. “Have we considered X,” or “have we factored in X,” are a good way to go about this.

Try and move away from using language that perpetuates the ‘us’ versus ‘them’ mentality — make it seem like you’re on their side and you’re a team.

Be polite, consultative, and listen to what they have to say. It’s important to understand their perspective and empathize.

The interaction is not about asserting yourself or your personality, the objective is to communicate your thoughts and opinions in a safe space — and your boss should be able to do to the same.

What happens if you still disagree

It’s possible that you may not agree — or even agree to disagree.

If this is the case, you need to take it in your stride and be thankful that you were given the opportunity to express your concerns.

A good boss should appreciate the fact that it’s not always easy for employees to speak up and will be grateful that you care enough about the business and the rest of the team to do so.

If the conversation doesn’t reach your desired outcome, you’ll need to think about whether the issue is important enough for you to either consider moving on or consulting someone else from management. If you opt for the latter, be transparent and mention you’d like to explore it further.

You may also want to ask to trial your process for a limited time. Let them know you feel very strongly about this and ask whether they’d be open to letting you try your method for a couple of weeks. It’s plausible that your boss will be open to allowing short-term change, as opposed to committing to changing things in the long-term.

These conversations will be draining. You’ll have to make a concerted effort to keep emotions at bay, and you run the risk of not getting your boss to agree with you. But, if you follow these guidelines you should be able to have a productive conversation without losing your cool, and hopefully, your boss will respect you even more after you’ve expressed your opinion.

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Published August 17, 2020 — 10:28 UTC