How to Work With The Boss

We all have a boss somewhere, even if it is yourself. I have been a boss and subordinate for most of my military career and have learned to understand what my boss requires.

It’s challenging to know what your boss expects from you if you haven’t set the expectations.

Your boss wants four things from you that I’ll discuss in detail: honesty, predictions, problem-solving, and doing your job.

I have written articles about handling employees and peers as part of this professionalism series.

These are things your boss expects of you.


Problems are like leftovers; they don’t get better with time. Be honest about your struggles. If I had a nickel for every problem that one of my soldiers hid from me, I would be a rich man. Similarly, it would help if you let your boss know what’s going on.

If you have an unfriendly boss, try to resolve the issue by bringing it up in private. If you can’t resolve the issue, bring a friend with you to help share the load-bearing news. No boss likes to get blindsided by an avoidable problem.

Even more, if you get in trouble for something, own it. Take responsibility for your actions. What’s even better is if you’re proactive.

Approach the boss, admit your mistake, tell the boss your solution, then move on. That way, the boss can’t get mad if you already have a solution in mind. Ensure that your proposed solution will resolve your issue.

Be honest. You’re not doing your boss any favors by hiding significant issues. However, do not bring up every little problem you have. That would inundate the boss with your concerns.

Only address the things that would concern your boss or if you’re unable to handle the issue at your level. Here’s a guideline of questions to ask yourself whether you should elevate the problem to your boss’s level:

-How will this issue impact the entire team?

-Will this issue embarrass the boss or team?

-Will this issue impact other teams?

There could be more depending on your situation but use these questions as a guide. The intent is to make the team look good. If your problem could make it worse for you and your team, then you should probably talk to the boss about it.

How to work with the boss

Photo by fauxels

Predictions and Risk Management

As the employee, the boss expects you to provide analysis. Within your cubical, you have your sphere of responsibilities. But your boss isn’t looking over your shoulder the whole time at your data. So, they don’t know what you know.

It’s your job to tell your boss what you know and how it impacts the organization. Think of yourself as a weatherman. How does the weatherman talk about the weather?

-He tells the highs/lows of the day

-Tells you about how the weather impacts the person (it’ll be hot/cold)

-Makes a recommendation (wear a jacket or shorts)

For your job, you state your problem, how it impacts the organization and then make a recommendation for fixing it. Charles Duhigg authored a book called Smarter, Faster, Better, where he discussed predictions. To create accurate predictions, people must assign multiple outcomes to a problem with a given percentage that each outcome will occur.

Using this method, you’ll be able to see future possibilities to problems and assign resources to solve your issue.

Bosses have a risk-mitigation mindset. So, bosses must view a problem in terms of risk vs. reward. In short, brief the issue with its associated risk and couple that with a solution.

As the employee, you have to spell it out for the boss. For instance, what risks are they taking by implementing your solution? What risk is there if he/she leaves the problem how it is? It’s a balancing act, but an employee must inform the boss on making the best decision possible for the team.

How to work with the boss

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Problem Solver, Not A Problem Creator

Being fully accountable for your job is critical to your success.

Solving complex issues comes with anticipating friction points as they come. For instance, have you looked at the company calendar and found conflicting deadlines? You’re now responsible for resolving that issue.

Also, don’t look at your job description and say, “well, I only do what they tell me,” or, “that’s not in my job description.” That attitude hurts the team and especially your boss. I mean, if you want to do well,  you’ll need to look outside of your “job description” to figure it out.

Keep in mind; your boss hates it when you bring up problems without solutions. It drives your boss crazy because now he/she has to spend time trying to solve your problem.

It’s one thing if you bring something up and have a half-baked solution for which you’re asking for assistance. However, it’s another thing entirely when you say, “Hey boss, this thing is broken…” then silence…

In your boss’s mind, he’s thinking, “Ok…go get it fixed! What am I supposed to do about that?!!?”

Make your job easier. If you need help with a problem, have a working solution and ask for resources from the boss. Also, don’t just go up to the boss and say, “what do I do now?” That’s your job to figure out.

Just Do Your Job!

If everyone just did their job, didn’t harass anyone else, and did the absolute BARE MINIMUM, that team would be the best in the organization.

By default, we think in terms of high, mediocre, and low performers. Even though bosses love high performers, those employees cannot sustain the team. Low performers and mediocrity weigh the team down because they pull resources and time away from the boss.

I can’t tell you how much time, mindshare, and frustration I expended on soldiers who did not pass their physical fitness tests, were not in compliance with their medical appointments, or generally performed poorly.

I remember when I wasn’t meeting my boss’s expectations early in my career. In essence, I was a low-performer. The pressure was real because I knew I wasn’t performing the way I needed to improve my organization.

Fast forward later in my career, I had been reading more books and engaging better with my bosses. Moreover, I learned to do the minimum and then do more. I couldn’t be a high-performer unless I did the minimum that was required of me.

Now, you want to shoot for gratefulness. Your boss loves high-performers because it makes their jobs easier. That’s where you want to be.

If anything, do your job, and you’ll be alright.


All your boss wants you to do is do your job, help your peers, and support decisions. Even a mediocre worker can do that.

Overall, encourage others to contribute to solutions for your boss. Also, provide candid feedback to superiors because they can make changes that will help you.

Working with your boss can be a good experience, but it starts with you first.

What expectations does your boss have for you? Let me know in the comment section below. Thanks for reading!

Books Mentioned

Smarter, Faster, Better by Charles Duhigg

Image Credit

Featured Image: fauxels

1: Sora Shimazaki

2: fauxels


4: Chevanon Photography


6 thoughts on “How to Work With The Boss”

  1. These are great tips! I always find if I’m proactive and show my boss my mistakes that they work with me. I find it imperative also to present to your boss the solution to your mistake. I try to explain what was learned and what steps we can put in place to prevent it from happening again. You won’t believe how much respect you gain! great article! I’ll be looking for more!

  2. We agree with you on dont wait to have the boss tell you what to do just start doing your job and stay on track with work.
    This hurts the team and will not build good relationships with your peers to have a good structure in the job zone.
    I know that these little tips that you have for us to keep strong and be encouraged to help others out and not be selfish.
    The article is relevant to us we are our own boss and have a structured life that we have for ourselves to get things done quickly and efficiently.
    Look forward to seeing what your next article is about and see what other skills we can build from the relevant contextual content you are writing.


  3. Hi Robert, Thanks for this!

    I’ve certainly wished that team members (and some bosses) would have worked this way! My biggest gripe – as both a team member and a boss, is people who bring problems, expecting them to be immediately solved – without having taken any time to consider what a solution might look like. I’m happy with half-baked, wacky, out there potential solutions it shows initiative!

    But I think the key is the honesty section – owning up to mistakes shows a level of courage and maturity that is often missing in organizations!

    What other books would you recommend to help employees develop their skills for working well with the boss (Other than Smarter, Faster, Better)?

    Cheers, Lisa

    1. Lisa,

      You’re absolutely right! Having issues and developing solutions is a great way to support your bosses. For books about skill development, I recommend Extreme Ownership by Jocko Willink and Leif Babin and Turn the Ship Around by David Marquet. I have reviews on those two books (and others) here on the site as well. Thanks for your comment!


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