No matter how skillful you are in your job, problems, challenges and issues are unavoidable. Some of them will be ones you can handle on your own without anyone else being the wiser.

But often, you’ll have to tell your boss. And that’s where things get interesting… and stressful.

Because bosses come in many shapes and sizes, and they each have their own temperaments, there’s no single best way of communicating problems or challenges.

Fortunately, there are some rules of thumb that may be helpful when presenting challenges to different types of bosses, which I’ll get to in a minute.

But first, there are two keys to success no matter what kind of boss you have.

Be Timely When Communicating Challenges

The first key to success is timeliness. You want to tell your boss about problems, challenges and issues early enough that there’s still time to fix them.

Or if they can’t be fixed, then at least give your boss enough time to do damage control and manage the fall out. And rather than come with just the problem, it’s important to come with your proposed solution. 

The three timeframes to think of are:

  1. As soon as you see signs of a potential problem looming on the horizon. That’s a great time to flag the issue with a simple, “Flagging this as something to keep an eye on. If it progresses, I plan to do X and will keep you updated.”
  2. When the problem or issue is looking likely. This is when you really need to have a proposed plan of action and get input from your boss. The best way to communicate is to stick to the facts and describe the situation, then your proposed way forward, and ask for their thoughts. It’s also a good time to suggest the action that you need from your boss.
  3. If the problem is already here and you haven’t had time to do the early warnings, then the best way is to tell them the current situation calmly and succinctly – what’s happened and where things stand, what you propose to do, and what support you need, if any.

Get in the Right Frame of Mind

The second key when you’re facing a challenge is to get yourself under control.

Breathing, quieting your thoughts and replacing them with calming words like “focus on what we can do” or “you can do this, May” work well for me. What works for you?

See how you can reframe the situation for yourself so you can get in a constructive mindset and stay out of “fear mode”. When you’re in fear mode, you can’t think. You can only react, and that won’t serve you well.

This is a great time to look for the opportunity in the challenge or problem. What can you learn from this? How could this become a positive for you and your team? Where’s the silver lining?

Being in an opportunity-based frame of mind will help you communicate professionally with your boss and come across as the leader you are.

Keep in mind that this is about getting yourself into a proactive rather than reactive mindset. It doesn’t mean presenting the challenge as an opportunity to your boss (it’s up to your boss to say that, not you!).

The sign of a great leader is to be able to keep a clear mind even when things go wrong, so do your best to manage yourself and your emotions.

Once you’ve gotten into the right frame of mind, it’s time to give some thought to the most effective way to approach your boss. How does your boss like to be communicated with? What style and approach has been most effective in the past?

Communicating Challenges to Your Boss

You will have the best insight into how to communicate with your boss based on your knowledge of their temperament and your past experiences, so trust your judgement.

If you’re uncertain, you can also ask mentors and colleagues you trust for their input if they’ve had more experience of your boss than you.

In my experience, there are four main types of bosses:

  • The Micromanager
  • The Hands Off Boss
  • The Drill Sergeant
  • The Too Busy Boss

As you formulate your thoughts, you might find the following observations useful about their tendencies and the strategy that works best for presenting challenges to each of them.

The Micromanager Boss

Their Tendencies:

A micromanager is usually someone who needs to feel in control of what’s going on. They’re concerned about making mistakes and letting others down… and having it reflect badly on them.

Often, they’re also perfectionists who subscribe to the idea that “if you want something done properly, do it yourself” but have gotten to the point where they physically can’t do it all on their own. The next best thing is to “closely supervise” someone else (i.e. you!) to do it exactly the way they would have done it.

They may also be new to their role and want to make a good first impression.

Your Strategy:

Tell your boss early and often. Keep them updated more often than you might think necessary. Since micromanagers hate surprises, give them plenty of warning so they can take the actions they think are necessary.

Keeping your micromanaging boss apprised all along the way will put you in a better position in the event the problem becomes real. If you don’t and the problem pops up as a surprise, they’re likely to beat themselves up internally for letting this problem occur and double down on micromanaging to prevent the issue from occurring in the future.

Once the problem or challenge is real, be ready to provide complete details in a succinct way. When a micromanager is under stress, they’re likely to be impatient even though they still want to hear all the facts. Again, if you’ve kept them in the loop all along, things will go more smoothly and your relationship can even improve.

The “Hands Off” Boss

Their Tendencies:

The “hands off” boss is the opposite of the micromanager. Their tendency is to leave the team to get on with whatever needs doing. They expect you to be resourceful and creative. They tend to focus on the big picture and don’t want to be bothered with the minutia of day-to-day operational details.

They’re more interested in results than the process of getting from here to there, and their expectation is that you’ll be up to the task without needing a lot of input from them.

However, if you do need their help to achieve the result (like make a phone call to their counterpart at the client or negotiate for more resources), they’re usually happy to help. In a way, the tables are turned in that you’ll need to direct your boss to do what you need them to do rather than the other way around.

And even though they’re “hands off” when things are going well, some Hands Off bosses can suddenly become Drill Sergeants (coming up next) or Micromanagers when faced with a problem that makes them look bad.

Your Strategy:

When you tell your “hands off” type of boss about a problem or challenge, remember that their default is to let you deal with it, so be prepared to do just that. Think through your proposed course of action, including any input or interventions you need from your boss.

When you speak to him or her, present the issue along with your proposed solution and get their thoughts on what they would add or change.

Be direct in letting them know what you need them to do and why it’s in their interest to take that action. If there’s a deadline, let them know that too. To get what you need from a Hands Off boss in a crisis, it helps to lay it out calmly and clearly for them.

You will want to strike the right balance between telling them enough of the background so they understand the issue quickly, and giving them all the information you’ve been living with in the lead-up to the problem emerging.

Your Hands Off boss will appreciate your being able to give them just the right amount of information at just the right time to avert disaster and generate the desired result. In essence, you’re providing leverage for them to spend the smallest amount of time managing you for the biggest return for the team and the organization.

Doing this successfully requires that you understand your boss and have a trusted relationship on the one hand, and also have a grip on the challenge and how to solve it on the other hand.

Done well, you can even gain a reputation for being good in a crisis!

The Drill Sergeant Boss

Their Tendencies:

Most Drill Sergeant bosses believe in “tough love”. Putting you under pressure and testing your limits is part of what’s necessary for you to become the best you can be. It’s a tough world out there, and it’s the boss’s job to make sure you’re able to thrive in it. 

They also tend to be direct. They don’t sugar coat or mince words. They tell it to you straight, even if it stings.

In some cases, Drill Sergeants may be unable to manage their own stress. This is when they go beyond simply testing you and it starts to feel personal.

The key is to not take things personally (frankly, that’ll make your life more enjoyable whether or not you have a Drill Sergeant boss). Instead, think of it this way: just be glad you’re not married to them!

Your Strategy:

With a Drill Sergeant boss, it’s best to tell it like it is. Think of it as the “Rip off the Band-Aid” approach. Get to the point and stick to the facts.

They tend to be uncomfortable with other people (you, in this case) showing emotion. Even if they’re shouting, it doesn’t mean they want you to shout back. They may not even realize they’re yelling at you.

What they do expect is that you can take the heat without crumpling. So expect the heat blast response, breathe through it and stick to being matter-of-fact. Let them get their initial reaction out of their system so you can go on to a more rational discussion.

And if they go on for a long time yelling at you, but you need to move forward, then say something like this: “I respect that you have every right to be angry with me and I’ll be around all day to continue this part of the discussion, but in the meantime we have a room full of people waiting to hear the next step. Here’s what I propose (describe your plan). I’m interested to hear your advice.”

The Too Busy Boss

Their Tendencies:

The Too Busy Boss tends to be a nice person who has a hard time saying “no” and may struggle to delegate effectively. That’s why they have so much on their plate and so little time to focus.

While they do their best to please everyone, they end up stretching themselves thin across too many tasks and projects. Often, they feel frazzled and as though they’re not on top of things. They are likely to worry about things falling through the cracks and feel anxious about depending on their team members to handle things.

Unless they have a great Personal Assistant, they may be a bit disorganized as they’re juggling so many “priorities” and commitments. This means they may not have read your previous briefing documents or may struggle to even find them.

Because they’re pulled in so many directions, it’s often hard to get on their calendar or to count on them to follow up on what they’ve said they will do.

Yet they care about you and the rest of the team and want to be a good boss if they only had time to do it well.

Your Strategy:

They’re likely to be hard to reach, yet still need to know. So, you’ll need to be quite persistent to get their attention, and clear in your recommendations on what to do.

Reducing your “ask” to the 1-2 actions you need them to take and making it easy for them to get it done while you wait is a strategy that has worked well for me. For example, giving them the 3-bullet point script for a phone call you need them to make, drafting the email for them to forward, or bringing a copy of the memo you need them to sign off on can work wonders.

Recognize that while the Too Busy Boss is typically a nice person, they may react emotionally because they’re frazzled and overwhelmed with too much else going on. Again, don’t take this personally. Stick with being matter-of-fact and maintain your composure.

In a calm moment after the challenge has passed, see if you can agree a special signal or way to get through to them when it’s critical to do so. As in when there’s a challenge or problem they need to know about.

Your Challenge is an Opportunity

When you have to present a challenge to your boss, treat it as an opportunity to strengthen your relationship.

When done on a timely basis in a manner that matches your boss’s style (and yours), you can demonstrate your composure under pressure and ability to find solutions that save the day. And more importantly, build trust.

We all face challenges, problems and issues. The key is how you handle yourself when challenges hit.

Now, I’d love to hear from you…

What’s been your experience of presenting challenges to your boss and what strategy has worked best for you?

Leave me a comment and share your experiences.