The Underboss

As the clock ticks closer to 1:00 pm, the room falls silent. Fifty-seven more seconds. There is a palpable sense of panic. All staff members are present, spread out across the room. Desks had been taken out and seats arranged forming a circle specifically for this session. Twiddling thumbs and foot-tapping betrays the poker faces everyone is trying so hard to pull. Nobody has any idea how this is going to play out. We are clearly in uncharted territory. 

Two men walk in and take empty seats set up right next to the door. I glance at the older man. Shoulders hunched over under the weight of an invisible load. Considerably aged overnight. He has a defeated look on his face. Possibly due to the emotional toll that comes with running such a dynamic startup. Our eyes meet. Fear written all over them. An emotion I had never seen him display before. This takes me back to how it all began.

The year is 2015, I am straight out of college. Suddenly uprooted from the safety, identity, and order that comes with being a varsity student, under the care of parents, catapulted into the murky waters of adulthood. Nursing the loss of my company. A firm I founded in my final year, clinched a contract that saw me subcontract three of my lecturers to undertake the works. After classes, I would walk into their offices to discuss the project details and suggest the changes I wanted to be effected. The company was set to be my golden ticket out of campus only for it to fold even before I graduated.

The management trainee programs I had applied to all sent back their regret emails in the same week. I was banking on joining one of these programs in order to acquire the requisite managerial skills that would enable me to better manage my future ventures. Hell, even an organization I had applied to as an unpaid volunteer turned me down. Everywhere I turned the world seemed to remind me that I wasn’t good enough.

Stuck at home, unsure of what the future holds for me. Hit squarely by the Kenyan quarter-life crisis, I delved deeper into the only thing that hadn’t rejected me. Writing. I poured my heart out into every piece I published. Earnest cries of a young man with big dreams now tethering at the end of hope after being dealt with life blows. 

Thousands read my articles, mostly young people who were in the same predicament. We shared words of encouragement in an attempt to numb the feelings of despair and disappointment in ourselves.

On the same platform accomplished men and women, possibly reminded of their younger self, reach out asking for a meetup. Sadly, a good number pitched to me the most absurd ideas. They saw a desperate young person who had some little influence they could exploit. 

I remember a man who ran one of those shady multi-level marketing firms tried to have me convince five friends to fork out Ksh 50,000 each in order to buy some products he alleged had unparalleled health benefits. In return, he would give me Ksh 20,000 with a promise that in less than a year, I would be swimming in money.

“If I can convince five friends to loan me a total of Ksh. 250,000, why would I hand over the entire amount to a complete stranger who would then give me back less than 10% of it and overpriced placebo products without a ready market instead of injecting this capital into my business where I had control over my investment, could actually offer employment to fellow youth and add value to the economy?”  I posed. 

Suffice it to say, he couldn’t come up with a convincing answer. I politely declined his offer.

Back at home, my folks, relatives, and mentors were on my neck to move to the U.S. or Europe for my postgraduate studies. All through my schooling, I had always topped my class. They felt I would best fit in the world of academia. But deep down in my heart, I knew I wanted more to life. To use my skills and talents to empower actual people. Even better, give them the dignity of earning a decent living while still making good returns to my investors. Entrepreneurship.

When I received yet another email from a man asking me to meet him at his office along Statehouse Road, every fiber in my body urged me to turn down the invitation. I couldn’t handle another disappointment. However, my old man urged me to go meet the guy.  

“What have I always taught you? Opportunities lie in people. The more people you meet the more opportunities you open yourself to. And even if you don’t find one, there is always something new to learn from them.” 

A cab drops me at what used to be Hillcrest Business School. From the road, the property looks rather unimpressive. The main gate opens up to a large empty parking lot. Walking in, I discover the property is essentially a U-shaped single-story structure that housed studios, a restaurant, and offices.  

Going down the steps I meet a tall, athletic, middle-aged man dressed in a blue-striped shirt, tucked in fitting denim jeans, with brown boots, and a matching belt. Smiling broadly, hand stretched out. 

“ Thank you for coming down here. I’m Tom.”

“Mark Maish.”

He introduces himself as the CEO of a Pan-African multimedia production company that produced sports TV shows, animations and news that went out to global broadcasters. 

After exchanging pleasantries he takes me on a tour of the office. Abstract canvas paintings hanging on Portland Orange painted walls, flower pots, director’s chairs and ambiance announced it was a creative space.

There are two sections separated by a paved courtyard. The main block which hosts the larger team, working on TV shows, features private offices, a coworking area with a series of huge iMac desktops, studio speakers, and young fellas sitting around them, headphones plugged in, working on MacBook Air laptops. We go round as he introduces me to the team. Each one passionately talks about what they do. 

The news section is entirely different. The head is in a suit and everyone has this serious demeanor on their face.

“They have to send out all our stories before the morning deadline,”Tom offers.

After the tour, we sit at a round wooden table near the main block where he grills me about my life plans, nodding and smiling as I talked. A meeting that was set to be brief ends up taking three hours as we converse about various topics ranging from the media industry to the deep love we both have for Africa.  

He asks me to come back three days later. Which I did, spending the day hanging around the different teams trying to better understand what they did. At the end of the day, we sit again at the table.

“You have real talent, big dreams, and the right mindset required to achieve them. I also like how your writing is not only authentic but also appeals to a diverse segment of readers. If you let me, I will mold you into a better and all-rounded creative.” He says, before making me an offer. Meanwhile, the HR manager is sitting right next to us working on a job description, creating a new position for me.  

An emphatic yes. How could I turn down an opportunity to work with such vibrant creators? Plus I was straight out of college with no work experience and here is someone offering to train and pay me for it.

On my very first day at work, I was tasked to sub-edit news scripts that were then voiced over and sent to broadcasters together with video footage. Without a journalism educational background script writing and editing proved to be a formidable challenge. Often I would write a script too long to voice over within the required time. In other cases, I would inject emotion into the script.

“This is news. You have to be impartial, short and precise. There is no room for personal opinions.” He would say.

Once we met the news deadline, I would move to the other office and sit right next to him. He would create time to inculcate in me basic journalistic skills. In a few weeks, I got better. I adopted a lean writing style where every single word is strategically placed to achieve a desired effect. No fluff.

When I mastered news scriptwriting, he threw me into another deep-end. I was now tasked with co-writing the TV show scripts, which is a complete opposite of news. The language on the shows was energetic, colorful, and required a mastery of the subject. One of the shows was on basketball. I had to start watching the game and constantly consume related news. I had to do the same for the other TV shows.

On Tuesdays, every video producer was required to submit a final cut of their piece. At midday, we would have a showtime where every segment would be played to the entire team. At the end, each member would point out what needs to be corrected in order to improve the piece.

“Correct the jump shot at 1min 23seconds.”

“Your piece is not well graded, work on that.”

“The background music is completely off.”

“Your montage begins with high energy then drops all the way to the end. You have to maintain the tempo.”

“As a viewer, I don’t connect with your piece. It is totally bland.”

Now, imagine having shot and sifted through hours of footage only to have a bunch of coworkers deliberately finding fault in your work. It was hard on the producers, strangely they all took it in a stride and worked on the corrections

The showtime would be repeated every 2-3 hours. Each time we would find more faults. This sometimes went on until 3 am. You could only go home once your segment was perfect. Good wasn’t acceptable.

Quality was never compromised. The man was a perfectionist. Everything you did had to be perfect. If not you would repeat it over and over until it was. This was a requirement for everything whether a business proposal, script, video edit, or even a poster. With time this trait rubbed off on me. 

As months went on, he took me through photography classes. From framing, lighting, props to capturing the three basic elements of photography. I was now tasked with joining the camera crew as they went around the country shooting. My role was to take pictures of the activities, behind the scenes, and live-tweet from the events. 

As it is the case with highly skilled individuals, producers preferred being behind the camera hence it fell upon me to handle the people side of things. Whether it was getting a vox pop for a news story, getting members we would like to interview to handling the curious crowd whenever we shot scenes on the streets of Nairobi, I became the go-to person.  

As my understanding of what the company does improved, the CEO decided to leverage on my people skills. I was eased into a marketing and PR position. Tasked to spearhead both on-ground and online marketing campaigns in order to grow both viewership and online followers. I would often attend events, exhibitions, and tag along when he went to meet business partners and clients.

“Our target audience isn’t just Kenyans, it is people across Africa. This means everything you do must have a continental appeal. Does your Ad appeal to someone in North or West Africa? Can anyone in South or Central Africa read your press release and relate with it?”

In an effort to appeal to a pan-African audience I spent my nights learning more about the peculiarities of other African countries. From parkour in Morocco, sand dune surfing in Botswana, Ghana fashion scene to car-spinning in Cape Town.

At first, all I did in the meetings was to listen and take notes. However, with time he guided me on how to create enticing PowerPoint presentations and pitch business ideas to potential clients.

Unbeknownst to me, the main reason he hired me was to groom me so that I would be able to launch and lead a new subsidiary of the company with my own team, majoring in digital media.  In essence, I was going through a crash-course on how to become an executive. In less than a year, I had moved from being an inexperienced engineering graduate to a media executive-trainee. 

The HR manager stands up from her seat dragging me back to the present. She opens up the meeting in a diplomatic way. Setting the stage such that both management and staff felt safe to air out their views without fear of repercussions. You could tell she was brilliant at her work by how she played this delicate role, wisely making sure to protect the interests of both parties. 

Having set the agenda of the meeting the managing director takes charge.

“First I would like to express how grateful I am to you all for continuing to work and giving your best even through such difficult times. We are working on other alternatives to get some cash to cater for your salaries since the bank rejected our request for an overdraft… I know how tough it is on you and your families as it is for me, nonetheless, we shall persevere as this is the nature of startups…When I started this company I made a decision to give every team member a stake in it. 24% equity, which we are now finalizing so each one of you can own a part of the company…” He goes on beseeching the members to have faith.

Never before had I seen him this vulnerable. Uncertain about the future of the company he had invested everything he owned. As a trusted associate, I was privy to the kinds of sacrifices he had made to keep the company afloat. Once he was done the HR invited the staff to also speak up.

One member after the other stood up and revealing how the delay in salary payment had impacted their lives.

“My landlord locked me out of my apartment. I am now squatting at a cousin’s place.”

“My bank has heavily penalized me for failing to make my monthly loan repayments in time. I don’t even know how I could ever repay the loan and interest accrued…”

“My car was repossessed last week. It was such a traumatizing experience…”

” Last night my son fell sick. I took him to a hospital but couldn’t afford to pay 900bob for his medication. I failed him as a father.”

In a few weeks, everyone’s life had been turned upside down. Having lost everything the previous year, I was leading a spartan lifestyle thus had enough savings to take me through a few more months.

When it was my turn, I maul over how to raise an issue the team had tasked me with. A coworker with a bushy-bearded shoots me a look as if to remind me of what awaits should I fail.

See, earlier that day, I stumbled upon a secret meeting by the staff happening behind one of the office blocks. Our salaries had been unpaid for about six weeks now thus members were absolutely livid. The caucus was meant to drum up a strategy for the meeting slotted at 1 pm. Even after working there for a year, I was still regarded as the new guy and spent most of my days working closely with the boss, which is probably why I hadn’t been invited to the meeting in the first place. Some expressed fears I couldn’t be trusted. It was unanimously decided that I would be the one to address a pertinent issue or face their wrath. Keen on earning their trust and eager to prove that I wasn’t a sellout, I agreed.

“Tom, we absolutely appreciate everything you are doing to address the money issue. I am certain it will soon be addressed. Since this is an open discussion the team asked me to raise a completely different issue we all share…We would like to kindly request you to have more faith in us. You are like an army general and we are your foot soldiers. As a general, you have lots of important and bigger tasks to handle, which is why we feel you are spreading yourself too thin by having to approve even the minute tasks each one of us does on a day to day basis. By guiding and trusting us we will be able to be more productive. Thank you.” 

There were smiles and murmurs across the room. The CEO, however, was not amused with me for publicly airing out his weakness of micromanaging every employee from supportive staff to the most skilled members. His eyes narrowed. My words gutted him. It was like a dagger through the heart from someone he thought had his back.

By the end of the week the company was liquid once more, every worker got his dues. However, things were never the same between us. As days went by, it became clear that I was no longer the trusted associate. In an effort to earn the trust of my colleagues, I had committed a mortal sin. Betrayed the man in charge. 

I was officially the villain. Every task I accomplished after that was trashed.

“Your proposal is pathetic, tasteless, and pedestrian at best.”

With each passing day I became the target of passive-aggressive behavior and at times outright hostility. I tried my best to make up for everything, earn back his trust but nothing seemed to work. The negative energy was chipping away a little piece of my soul every single day leaving me in a foul mood. 

Walking on eggshells. The office moved from being a creatives nirvana I longed to go to every morning to a place I would dread to go to. Most nights I couldn’t sleep well knowing what awaited me the very next day. Subjected to continuous verbal torture, scathing criticism, and an overly toxic work environment I tender my resignation four months later.

Despite the bitterness I harbored, we parted ways in good terms. I chose to ignore the negative aspects and concentrate on the good parts. In less than two years, I had moved from being a clueless fresh graduate to a versatile content producer, marketing expert, a team leader, and an underboss. 

In retrospect, this period taught me the most important lesson about being an underboss. As young graduates, we often venture into the world with an ideal image of how it operates. Our naivety, false confidence, and aggressiveness that propelled us through campus blind us from unwritten corporate world rules.

Never publicly hold a position contrary to the boss or air out their weaknesses because your relationship is built on mutual trust and your resolve to cover their flank. Objective debates about such matters only work in the confines of intellectual forums. Once your loyalty is questioned, there is no going back. 

Picture this, a bunch of high school teachers may engage in heated political debates in their staffroom, publish long Facebook posts criticizing government policies and even tag the president without facing any repercussions. However, if a cabinet secretary to the Ministry of Education publicly airs out any views that contravene the appointing authority, they will be most likely summarily dismissed.

Consolidating power calls for a more calculated and subtle approach. The higher you go the more sycophant you are required to become in order to stay in power.

Written By Mark Maish

PS: For the next couple of weeks I will publish a series of articles under #TheUnderboss campaign, which essentially captures my experiences and lessons I have learned working for a number of accomplished men.  


Add Yours
  1. 1

    “The higher you go, the more sycophant you are required to become in order to stay in power.” I’m reading this for the third time. Now I believe it is true and I’ll stop judging sycophants the way I have done before.

  2. 4
    Ngosyi Mtinda Nzikali

    Bro, this is absolutely amazing…. I’ve read it more than twice… It once happened to me, I aired my Principals faults in a meeting with the cabinet in campus, for sure it was hectic..,

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