5 Strategies for When Your Boss Doesn’t Know How to do Your Job

(Author’s note: To begin, I’d like to share life experience with you that led me to write this… but if you want to head straight to the 5 strategies, by all means — scroll down to the middle for the juice! -Nikki)

When I was 14, my first job was working as a server in a 1950’s style ice cream parlour. I worked there for over 4 summers and I still look back fondly at those years because the workplace was fun, it had a great sense of community and I met lifelong friends there. But the real reason I stayed was that the company was managed by a charismatic and caring owner, who passionately knew everything about ice cream. She knew every job, inside and out.

The owner was a retired widow who used her family’s savings to buy the ice cream parlour and start her life anew. She was also a grandmother, so I always felt like she cared for the dozen young teens she employed like her own. It wasn’t an easy job though, because we lived in a seasonal tourist town, and as you can imagine, running one of the most popular ice cream places around came with all the challenges of impatient customers, ogling men who loved the sight of young women bending over with each scoop, and of course penny thieves who often “didn’t have enough change on them” so we had to dip into our tip jar to balance the register. There were about a dozen young ladies like me working for her and it was very busy from opening to close, sometimes a line would form around and outside of the building on the hottest of days.

Over the 4 years I spent there, I was offered jobs by other local business owners for more cash (I now know this is called headhunting) that paid more for less hours. While attractive at first, I turned down all offers because I knew the reputations of those owners and managers to be hard, unforgiving and to be uninvolved with their teams — basically they were known as “Asshole Bosses”. They owned the place, so do as they say, not as they do. Truly though, the reason I stayed at the ice cream parlour was because I felt valued and respected by the owner, and that respect boiled down to one saying she always told us. It simply was

“I would never ask or expect any of you to do something that I wouldn’t do myself.”

And she wasn’t lying! I distinctly remember on a hot sweltering day, while doing my bathroom spot-checks and cleans, I realized someone had a literal explosion. To this day I have never seen anything like it. I immediately locked the bathroom, tried not to vomit and went and told the owner. Because 15-year-old me at the time, had literally, never, ever seen anything like it… (I’m in my mid 30’s people, this was pre-internet and 4chan days). As I began to tell the owner what I had encountered, she softly stopped me and said, “Don’t worry, I’ve got it. I would never ask you to do that if I hadn’t done it myself.” And off she went with more determination and fearlessness I have ever seen in any grandma. My hero.

Lucky for me I never had to experience another bathroom explosion like that and I never really had to “take my turn” in that sort of mess. But when it comes to the working world today, more horrible things have happened to me since then, than some bathroom explosion mess. Some of these things actually upset me and made me sick to my stomach. You see, we now live in a world where many of the corporate, administrative and computer-based jobs are being managed by people who don’t know how to do the work of their employees. We have a massive gap of the leaders and the doers, and we’re still a couple of decades away before “that” generation retires out.

Before I became a business owner, if I could put on my hand one overarching reason why I really wanted to quit or leave a job… it always came down to mutual respect and inclusion from my boss or leaders. I’m not talking about the morning salutations and lunchtime social invites type of inclusion or respect, I’m talking when a manager or leader is asking you to do a job that they don’t know how to do themselves — and how they handle it.

The days of

“I would never ask or expect any of you to do something that I wouldn’t do myself.”

are now the days of

“I am asking you and expecting you to do something because I can’t or won’t do it myself.”


I realize now that the ice cream grandma’s principle has had a huge impact on how I relate and appreciate my leaders and managers throughout my career. It is extremely difficult to work under a boss who doesn’t understand what you do. If they hit a point of redundancy, then they will either learn and educate themselves to improve or… you guessed it… delegate their redundancy downward to the young whippersnapper in the workplace.

*Cough* *Cough* That ’s you.

Technical skill redundancies are something that my generation has grown up with and expect just as much as we do another Kardashian baby. I remember in middle school using typewriters for basic typing skills, and now I’m able to dictate this entire story into Word with voice recognition. Most of us have accepted that we are living in a generation of redundancy, where as soon as you master one skill or program, a new one comes along to replace it. It is impossible not to become redundant in our working world, so I feel for many of us, we have embraced this fact.

So, what do you do when you have a boss that won’t do the tasks they are asking you to do, but literally doesn’t know how to do them either?

Abandon ship?

Nothing is more soul crushing when your boss volunteers you for a task that they think will take 20 minutes, when really, it’s at least a 3–5-hour job and they slide it on your desk as they head out for their extended lunch break. Then that same boss hovers over your desk when they are back pining and prodding about when that “small request” is going to be completed. Because really — it’s their reputation on the line, not yours, right? After all, you’re the workhorse, and they are the brains, right? Ugh.

So, if you’ve experienced some redundant-ignorant-boss-hand-me-down scenarios like me, you might need some strategies in your back pocket:

5 Strategies How to Handle a Boss That Doesn’t Know How to Do Your Job

(Disclaimer: While most of these things have worked wonders for myself and my clients, I did have a super-horrendous boss once that was so uptight and rigid, they would just ignore me for weeks instead of responding to any of the remedies below. When you have a boss like that — just GTFO. Track everything and believe me that they aren’t going to change, so cut your losses early and find greener pastures.)

Strategy #1: Don’t Make Them Feel Stupid

This is the hardest one. When a boss signs you up to do something quick without understanding any of the work involved, you need to remain calm and get as much information as you can while the work is being explained to you. If you get work assigned via email or slack, go for a walk, grab a cuppa or do something else for 10 minutes before responding.

First remember that if your boss is handing you extra work or responsibilities, much of the time it’s because they trust you to do it. That is unless they are trying to bury you in work to burn you out — and if that’s the case, GTFO vibrant one, you can do better.

Second, if your boss is asking you to do something they don’t know how to do, they are relying on you far more than you realize. With this knowledge comes the internal power to know that you have an opportunity to become your boss’s greatest asset or the biggest thorn in their side.

Responding to new work assignments with “why don’t you just…” or “this is not part of my role…” or “how did you not already….” Or “who made this mistake…” is a great way to insult and make your boss feel stupid. What do people at work do when they feel their intelligence is questioned? Lots of bad things that I don’t need to explain here, right?

Above all, uphold the confidence of your boss when they mistakenly assign you something they don’t understand themselves.

If you look for the bad in the scenario — that’s all you’ll see, so be calm, stay positive and move on to #2.

Strategy #2: Ask Questions

This is your chance to make sure you understand key elements of the work like scope, urgency vs importance and the timeline/deadline. Try not to accept new work willingly without knowing these key elements as you and your boss may have very different expectations. Clarity is key, because no one wants to spend an entire day of effort on a back-burner-destined idea-fart.

Once you have established the key items for the assignment, now you can ask questions related to your day-to-day work. Meaning, if the work is urgent, then request overtime by coming in earlier or leaving later to get it done on time. Overtime or time off in lieu not possible? Then ask to have another important and less urgent deliverable bumped to a later deadline or pass some of the work off to a fellow colleague.

Don’t make assumptions. Does your boss need oversight or final review? If this is “urgent” but you don’t think it’s important, make sure you understand why your boss is pressing this assignment. If you determine your boss doesn’t think it’s urgent but gives you a vague deadline — set one yourself and ask them if they are “ready to review” the completed work on a set date, which will make them realize the deliverable they just gave you still needs their time to be reviewed and approved.

Strategy #3: Educate Your Boss While Updating Them

When you’re asking questions, this is a great way to slide in some of the elements of the work your boss doesn’t know how to do, solidifying your value. If there are “must dos” in your line of work that your boss doesn’t know about or understand for this new assignment, start explaining it to them in updates and communications as you work on it. This can be simple statements like “Just have to get the ______ setup, then I can move into the _________, before I do the finishing touches on the _______” or “It takes 2 hours for the configuration, so during that time I will work on the other important elements which are…”

If you’re not meeting with them regularly about the work, send them progress reports. When I worked for a super busy, maxed-out-by-meetings manager I felt the only way I was able to show my value and what exactly I was doing in my day-to-day was to write an “End-of-Week” or “End-of-Day” email report. I would state high-level examples of what I worked on, the status for ongoing projects and set delivery dates. I even included a short list of “upcoming” projects and deliverables, so they knew I was swamped once I finished my current workload. The 5–10 minutes it took to write those emails saved me hours of questions and backtracking when it came to my boss. Then, when I became that “super busy maxed-out-by-meetings” manager, I had my team send their versions of daily or weekly reports if we weren’t able to have a face-to-face meeting the next workday morning next day so I knew where the team’s mindset was before I delegated again.

Innovate! If you know a better, faster, more efficient way to do the job than how you’re expected to do it, sometimes you can convince your boss to let you do it your way. When updating them, you can ask things like “Hey, we usually do it this way, but I know it will be more efficient if I do this instead…” or “I learned how to do this in half of the time by doing it this way…” or quite directly “If you can put your trust in me to do this, I want to try a better way.”

If you can’t convince your boss to change a time-sinking process the first time around, that’s okay! But know, if you don’t update the process or efficiency, your uninformed boss won’t do it either. And so the head-to-desk banging cycle continues.

Consider innovation for progress and change in your workday as much of your own responsibility as the people who approve it, because as the informed/educated/”woke” employee it is up to you to educate the higher-ups if there is a better way to do it next time. Then, if you do explain there is a better way, the next time they delegate a similar task to you, your boss should be expecting your request to change the process early the next time around, saving you from looking reluctant of accepting new assignments.

If they know you’re willing to make improvements instead of going all Maverick on them, you’re more likely to be approved and seen as a team player, rather than another over-worked walled-up complainer.

Strategy #4: Be Organized

If something is going to take a lot longer than your boss thinks, ask them if the “other” deliverables can be moved to later dates to accommodate for this unplanned workload.

If you use a calendar system your boss or team can see, set visible time aside for deliverables that they have zero-time concepts of, so they can see you are spending a % of the week or day on something that they asked you, because they can’t do it themselves. This will also allow you to turn away meetings and other work requests, because you’re doing the work you were assigned based on urgency/importance.

In one particularly trying manager-employee relationship, I frustratingly used a time tracker when I felt that too much of my workday was delegated work from my boss’s portfolio to show how much time I was losing to them outside of my regular day-to-day work. When I had enough data, I requested a meeting to show them that I would either like a promotion, raise or to hire a new part-time staff member to report under me if I was going to be able to sustain the additional and unforeseen workload, long term. Did I get any of those things? I did! But it took patience, and months of working with my boss and HR to get there . I rarely have worked for a boss that can snap their fingers to approve a request for a raise, promotion or new hire— remember, your boss has a boss or some sort of oversight, so good change takes time. Which leads us into the last strategy:

Strategy #5: Recruit or Get Some Help

If you’re working in a department with many roles that are open to cross-training, use this “open door” to identify team members who are interested in your work and teach them some core duties and responsibilities. The less time you must spend on everything, the more time you must take on greater responsibilities from your superiors, collaborate with your team and have some extra backup for your role when you’re busy or on vacation time.

Is there something your boss DOES know how to do that you can hand “up” to them to cover while you cover them? Depending on your relationship with your boss this is a great way to learn how they expect things to be done when you get to watch them dipping their toes back into work, they thought they grew out of. Sometimes a simple “hand-up” can change how everything is “handed down” to you, because a new perspective for your workload is sure to emerge if they agree to help you out.

Depending on where you work, you may be eligible to hire volunteers, interns or even part-time support for some of the simpler processes of your day to day work. Think about it, for every role and responsibility in your company, someone had to make the case for it to exist before the job was posted, hired and filled. Never assume that a “hiring-freeze” means no new people, because the most creative and dynamic leaders I have known have built entire departments around themselves during “hiring freezes”. Use data, facts, budget and everything you must make a case to recruit yourself some help.

Lastly, if you think often that “there must be a better way to do this”, then you’re probably right. Get on Google, search some blogs and see if there are other people out there that can give you some solutions to your problems.

That’s all for now! What do you think? Are there any more strategies you’d like to see here in dealing with a boss that doesn’t quite “get” what you do? I’d love to hear them!

And if you’re a boss reading this, I have one strategy for you:

If you can’t do the job of your team, at least make them feel respected and valued.

Again, these are just some ideas and strategies, and while I think they will help you manage the good-hearted and fair bosses who don’t know what you’re up to — they won’t work on everyone. You just can’t pick a list of strategies to use with someone who doesn’t respect you or give you the time of the day. Always seek a place of work where you feel excited about arriving.

But, if you’re finding that dread, that dark emotion boiling up inside you before you head into your workday because you know how bad it’s going to be before you get there — you’re not alone. I’ve worked myself out of some hairy situations and have helped people across many industries reignite their careers by switching or adjusting their direction. If you’re looking for a Fresh Perspective on your future — please reach out, it’s my greatest joy to help others find their perfect fit in their workplace and world.

Fresh perspectives on work, life and the “why” of humans. Consulting with conscience, resiliency and curiosity. Founder of www.snowberryconsulting.com

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