If you want to talk to your boss about a problem, it's best to be solution-focused. This image is a chalkboard with two words written on it in white chalk: "Problem" and "Solution". The word "Problem" is crossed out in red chalk.

How to talk to your boss about a problem

Dave Labowitz Career, Leadership

What’s the best way to talk to your boss about a problem if no one likes a complainer? This is a challenging issue because the wrong approach can be rather damaging. You can accidentally hurt your relationship with your boss and even mess up your career if you get associated with the words “complainer” or “negative”. 

Of course, you probably don’t have the option of simply not saying anything. You undoubtedly tried that the first several times. Most people don’t run right to their boss the moment they have an issue! Now, though, the challenge you’re dealing with has gotten worse… and you’re more frustrated. 

The good news is that, if you talk to your boss about problems the right way, you will not just get more help and engagement from them, you’ll walk away with a reputation for being productive and constructive. The next time you find yourself about to complain, keep the following eight tips in mind.

The right way to talk to your boss about a problem

Honor the chain of command

If you want to talk to your boss about a problem, that necessitates you actually talk to your boss, not to someone else. Remember the chain of command is there for a reason. While it’s entirely possible that management at higher levels than your boss have open-door policies, it’s best to start with your boss and only work up if you have to. Going over your boss’s head is an easy way to get on their bad side.

Be specific, not vague

If you’re going to describe a problem to your boss, it’s critical you’re specific enough that they get a good understanding of what’s going on and why you’re struggling. Details will prove you understand the full situation and help your boss come up to speed. If you’re too vague, your frustration will come across more than the issue itself.

Talk to your boss about facts

If you’re making a case for something to change then the best way to do that is by presenting facts. It’s far better to present objective data than just your subjective opinion. As an example, “The graphic design team is taking an average of seven business days to deliver a wireframe while we need them in four,” is a far stronger case than “We never have the wireframes when we need them.”

Don’t get too emotional

By the time you feel you need to involve your boss, you may already be rather frustrated. That’s completely normal. However, storming into their office and throwing a temper tantrum is the wrong thing to do. Take a few deep breaths before going in. Don’t think as much about what’s been wrong. Instead, think about how excited you are to work in tandem with your boss to fix the problem. Looking forward will help you keep a positive mindset while looking backward at all the frustration will put you in a negative mindset.

Talk to your boss about the business case

If you’re asking your boss for help with a problem, it’s because you’re looking for a resource of some kind: time, budget, authority, etc. You can make it easier for your boss to agree and commit the resource you’re looking for by presenting a compelling business case. Talk to your boss about the problem, not just how it impacts you, but how it impacts the company. Is it costing money? Slowing things down? Hurting morale? Then talk to your boss about how solving this problem will benefit them, the team or department, and the company. Are there any risks of taking action? Point those out, too.

Talk to your boss about what you’ve already done to address the problem

You shouldn’t be talking to your boss about problems you haven’t tried to solve yourself; that’s just complaining. It’s far better to explain all the steps you’ve taken to resolve the issue and what their results were. Your boss will respect that you took the initiative to try and will be more likely to help you. The one exception here is if you don’t have the authority needed to attempt to solve the problem. In that case, read number seven.

Offer some suggestions

It’s likely that you understand the details of the problem better than your boss does; that’s why you’re the one bringing it up. So you’re also in the best position to solve the issue, assuming your boss agrees with your business case. Help your boss help you by offering a few suggestions on how to solve the problem. This shows you’re committed to achieving the desired result rather than just getting stuck in what’s wrong.

Be clear about what you’re asking for

Since you’ve thought through and presented some suggested solutions, it should be relatively clear at this point what you need from your boss. But in case it’s not, make sure to explain precisely what you’re asking for. What do you want your boss to do? When do you need it by? If you leave ambiguity here they may not do what you need, the way you need, by the time you need it.

The next time you have a challenge you can’t solve on your own, keep these tips in mind before you go into your boss’ office. You’ll build a better relationship with your boss, they’ll learn to trust you and respect your initiative more, and you’ll get better business results, too. 

If you want some help on applying these tips before an important conversation, a leadership coaching session might be of great value. If you’d like to discuss working together, click here to book a free consultation call, or send me an email below.