5 Reasons Why You Should Want A Tough Boss

Whenever I encounter someone struggling under the weight of new professional demands, I share the story of my very first job.

I was 18 years old and straight out of A-Levels. After re-sitting Chemistry, I took a job for a few months at a boutique before starting University in the fall. My attitude going in was that working in a retail clothing store would be dead easy.

Charmaine was my boss. Every day, she would grill me on the exact way to write up receipts, make sure all the hangers faced the same direction, and how to fold the clothes so that they formed precisely uniform stacks. The racks were to be dusted twice per day, and all the windows had to be double and triple checked when leaving in the afternoon. Smiles were to be bright, greetings always perky, and customers always to be treated like royalty.

Charmaine was tirelessly exacting about everything. Customers should never walk in and find you seated, or with your back turned. Suggestions must always be made for accenting and completing every outfit. Colors were to always be described using yummy names. Every day for my first week, I went home and cried my eyes out. My soon to be off to University self-esteem was taking a beating. I wanted to quit. I hated her. Who makes such a fuss about working in a silly clothing store? But I toughed it out and stayed.

Charmaine taught me what it means to take pride in my work and to be excellent. The experience of working at ‘A Thousand Flowers’ boutique for a few months shaped my work ethic for life. Charmaine is still one of the people I hold most dear today.

My first tough boss, Charmaine, and me in 2008, 15 years after we first worked together.



People fantasize about their dream bosses, they dream of working for the kind of slacker who lets you get away with murder, go for lunch as long as you want, come in late, and who would never dream of insisting that you actually work hard to perform your duties properly. What you should really be wishing for is a boss who is smart, great at their job and demanding.

In short, you want a tough boss who is better at your job than you, and will notice every single mistake you make and call you out on it. The best bosses I have had are the ones that insisted on the highest standards from me and forced me to see and live up to my true potential. I read a great article yesterday which reminded me of this. The original article has an irreverent style and some strong language, so here’s a cleaned up summarized version of the 5 reasons why you should want a tough boss:

#5. Tough Bosses Don’t Hide Information Due to Insecurity

Many people rise to the top not because they are the smartest or best, but because they are intent on acquiring an unfair advantage. They covet information, and hide details. On the other hand, people who are really smart don’t rely on  controlling information. They’re confident in their abilities, so they are comfortable giving their employees the tools to shine. Smart bosses don’t waste time manufacturing games to make others fail; they spend their hours doing their job well. It might be hard to work for someone possibly smarter than you, but it is better than having to work for someone who maintains power through deceit.

#4. Tough Bosses Don’t Create Fall Guys

Bosses who are hypersensitive about their failings always create distance between their decisions and the project to be accomplished, so that there are more people to blame if something goes wrong. They create fall guys. A truly competent boss got where he or she is by doing the job better than anyone else. That boss won’t want anything substandard under his or her watch. They take the excellent performance of their teams personally. They will want to review projects before they are due, and that will be irritating. You should be grateful for this. If it is wrong, they will tell you in no uncertain terms to get it right, instead of having you fall on your sword to make them look good when it all falls apart.

#3. You Know Where You Stand With Tough Bosses

Many treacherous and incompetent bosses are super nice. Having everyone like them is a trick they used to become the boss in the first place. Nice means nothing. Even when things get really bad, they still act nice! None of the act is true and most people never see the knife in the nice guy’s hand.  Smiles and silence come easier than honesty. Distance grows more from things left unsaid, than things said in anger. Unspoken words and phrases build walls of hurt and insecurity. Those same walls can obscure the wrecking ball that’s coming toward your head. Yelling is not all bad. Raised voices and reprimands don’t have to be the same thing as abuse. It is always better to know exactly where you stand. “Nice” people are just not good at that.

#2. Tough Bosses Can Keep the Company Alive

Sure, a nice boss who doesn’t expect too much sounds great, but how good is he at keeping the company and your job afloat? The skills that rise a half-talent nice guy to power and keep him there are not necessarily the same skills that can keep a business successful. Clients and the public expect real competence and results. Sometimes all the hidden information, charming smiles, slick compliments and tricks cannot compensate for mediocrity. A truly talented boss can help keep the company alive, and keep your bread and butter coming.

#1. Tough Bosses Make You Smarter, So You Can Eventually Become the Boss

Bosses set tones. Even those who aren’t leading still set an example. If you work for a boss who rose to power and maintains it through deceit and guile, you will learn to play your cards close to your chest instinctively. You will learn to be distrustful, but you still won’t be any good at your job. A talented boss will teach you how to actually be good at your job, and not just how to appear successful. Even if you don’t think they care about teaching you, just the exposure to a competent boss will make you a better employee. It will give you a real skill set that you can take with you into the future, and give you the ability to become the boss one day. Your talent and intelligence will then create better employees and better future bosses.

6 comments for “5 Reasons Why You Should Want A Tough Boss

  1. Reeva Armstrong
    March 19, 2013 at 11:05 AM

    Hey Joya!

    Today I am experiencing a similar scenario. It’s not even having a tough boss its having a tough Accountant! In 2012 The Board of Directors of ACYM (the company I work with) hired an Account named Ava Samuel from Derrick & Watt’s Accounting firm. She was hired to clarify accounting challenges that occurred way before my time. She not only cleaned up the company accounts she cleaned up the entire organization of the firm! What a world wind this lady was! I often said to myself how could one person be so meticulous? She scrutinized and criticized everything I did, from office and file organization, to computer programs, to the way I spoke or answered emails. At the time I considered her to be a royal pain in the ass! However since Mrs. Samuel came on board, the painstaking implementations and polices she put in place has improved the running of the company. All the spreadsheets, reorganization, new formatting procedures really work! It was worth the effort! She has definitely strengthened my command on my position and made me even more comfortable in my career.

    • March 19, 2013 at 11:24 AM

      Kudos to Ms. Ava Samuel! And kudos to you, Reeva, for taking the challenge as a learning and growth opportunity!

  2. July 8, 2012 at 8:37 PM

    Thanks, Alan!

  3. Alan Scholl
    July 4, 2012 at 3:41 PM

    Just to digest this, I had to read it 3 times…

    Great stuff.

  4. Christian
    April 2, 2012 at 3:03 PM

    What you describe is not necessarily a tough boss, but an honest boss whose interest is the quality of the work being done. Acting tough is not what makes a boss good, it can also be a sign of being insecure, a control freak, exploiter, or sadist.

    During my entire professional career I’ve worked for people who were nowhere near as good as I am at my job. However, I have a different job than my bosses.

    It makes managing people much easier when you can do their job better than them. Good managers however, don’t depend on that. They are not threatened by good team members. They know that they bring entirely different and helpful qualities to the team.

    On the other hand, I definitely have to agree that one of the best ways to learn a profession is to work under a kind and knowledgeable master whose interest is to improve the work being done by improving you. Kind does not mean soft: The faster a mistake is corrected, the smaller is the opportunity for the mistake to become a habit. Unfortunately, big companies almost always actively promote competition between employees, thus strongly disincentivising being a kind master.

  5. March 22, 2012 at 10:41 AM

    Outstanding article. Very well written and hits on a great many points I bring up in my Leadership Seminars.
    Nicely done, you are spot on!
    Let me know if I can ever be of service to you. Keep doing what you are doing and never lose that attitude. You’ll be light years ahead of those who don’t!

    Donn Carr
    President/Principal Partner
    Carr Managment Group
    Saint Lucia, West Indies

Leave a Reply