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Client Horror Stories

Learning to be comfortable with uncomfortable conversations: A leader’s burden in choosing between professionalism and camaraderie

Learning to be comfortable with uncomfortable conversations: A leader’s burden in choosing between professionalism and camaraderie

This article was based on Episode #25: Kison Patel’s Story featured on our show’s last take and unveiled here for us alongside Our Beloved Host, Morgan Friedman. Please watch the complete episode here!


“You can enjoy the work if you enjoy the people you’re working with.” – Kison Patel

It has been common in prior episodes to hear stories from employees who have been mistreated by their clients or bosses. We understood their plight from their perspective and empathized with them as they described their harrowing ordeal. 

However, in this episode, hearing horror stories from the usual standpoint of employees, we’ll hear them from the boss’s perspective. Kison Patel’s story revolves around a horrible dilemma; to let go of his client working with his perfect team with whom he had a great relationship or recruit new people to match the client’s expectations, but at the cost of terminating the people he’s worked with for years. 

What would Kison choose? Would he choose professionalism or camaraderie? Continue reading to find out! There are also a lot of lessons in this story on how to become a good boss, so you better grab your notes and listen to Kison’s client-horror story.

The story began when Kiso founded his own company. But before it came to that point, Kison spent close to 10 years working in M&A as an advisor. His work was able to help buy and sell businesses, and he mainly worked with hospitality, hostel assets, and small financial institutions. Because of his experience in that field, Kison was able to determine and get familiar with that industry’s problems and pain points. 

Kison founded a small company, providing digital marketing skills and other technical support. During those times, Kison was genuinely interested in this emerging technology space and kept on popping up on the web. 

Kison was interested in this because he was thinking about the future and seeing younger kids getting heavily attached to their technology and devices, so he was thinking that everything was going to be all about tech soon. Kison involved himself in a marketing technology startup, but sadly for him, things went sideways and didn’t pan out the way he wanted to. 

However, Kison’s experience made him realize that if only software engineers would share their project management tools that help them manage building software, they might be able to help a lot of industries progress. 

Let’s say, for example, if software engineers shared bug tracking, which is one of their project management tools, it would really help a lot of workers in the digital marketing industry. To-do lists in emails get lost most of the time, especially when you receive plenty of emails coming from your clients. 

With the help of bug tracking, you can track your to-do lists in your email for you, and you won’t have to worry about forgetting a single email. Another thing that Kison realized was that you have to have a good team with expertise in each field that you need for your product to work. 


1. When building a team, choose individual expertise rather than a jack-of-all-trades

Hiring a person who is an expert on a specific field of work is better than someone who knows a lot but is an expert to none. When building a team, you have to evaluate first what kind of product you want to sell or what kind of services you want to offer. 

For example, you want to sell furniture. It is better to hire a person who is an expert at designing, woodcutting, and upholstering rather than hiring three individuals who know a lot but aren’t a specialist.

Going back to the story, Kison failed in his first attempt at a marketing technology startup. However, he still tried to do some ventures related to tech, but this time he did it right. Before deciding to create a product with his team, he looked for individuals who were experts in specific fields. 

He was fortunate enough to have found a young person that was really good at rapid prototyping. Kison said that rapid prototyping was a key component in creating the product he wanted, so he hired a person specializing in rapid prototyping. 

Kison was really confident in this young man’s skillset, and they established a pretty good partnership with each other. According to Kison, establishing a good relationship with your workers is a good thing because “you can enjoy the work if you enjoy the people you’re working with.”


2. The intimate level of friendship is different from the professional level of friendship

You may have already encountered this lesson before, but still, this is worth the second time. Always know the difference between the professional and intimate levels of friendship. Both have benefits and consequences, so you must be ready to take them. 

If you are close with your workers and have an intimate level of friendship with them, your work environment would be very healthy, and your employees would really love to work every day in the office. You treat them as equals, and you share your meals with them, which is not a big deal. 

However, when it comes to reprimanding them, you, as the boss, couldn’t easily tell them what they did was wrong because the intimate level of friendship is holding you back. A professional level of friendship is where you still establish a good relationship with your employees, but you have to let them know that you are still the boss and that respect towards work must always be present in the workplace. 

Also, never hire your friends in your company no matter how badly they need it. You can still help them by recommending them to other companies and letting their resume do the convincing, but avoid hiring them just so you can help them. 

That is because you already established an intimate level of friendship with them, and when there comes a time when they did something unforgivable, and you want to fire them, they will not take it lightly, and it would destroy your friendship even if you just did your job. 

Most of the employees want a professional level of relationship because people often want someone who corrects them and tells them what to do to improve, rather than receiving flowery compliments from their boss even if they know they messed up.

Going back to the story, Kison and this young man built a great professional relationship, and they started to build prototypes of effective products, and it went out to the market in an instant. These prototype products were really amazing, and people were starting to request for them to become real. But this was where Kison made his second common mistake. 

Being a future creep is a common mistake for all entrepreneurs. This is where you get so excited about the product that you had thought of. You remodeled it in your mind, and you enhanced its uses. You already had a lot of ideas in your mind on how to improve your product until you reached the point where your product already does 20 different things. 

Don’t get me wrong, dreaming big is not a bad thing, but if reality is so close to you, you have to think first of the possible and achievable things. 

In Kison’s case, his ideas were good, and the prototype was cool, but he overthought and got a lot of possibilities even if he still needed to solve his next problem: who and how they are going to build this prototype product. Kison managed to stop his overthinking and talked to his team about what they should prioritize first. 

Take note that the only expert in Kison’s team was that young man who was an expert at rapid prototyping. The other team members were his old teammates with whom he had already established a good professional and intimate relationship. So Kison and his team had a meeting, and they settled on what they were going to prioritize first. 

Kison’s team was well-organized, and they all worked together coordinately. The team was following Kison’s command and everything was on schedule. After 13 months of working for that product, Kison realized that they were essentially building a sophisticated dumpster for deals. Kison’s team did nothing wrong. In fact, they were doing their best. 

But even if they were not slacking off and were doing everything they could, they were not experts at creating that kind of product. Kison wasn’t an expert, so they relied on little knowledge from their brainstorming and went with it even if it isn’t 100% guaranteed to work. Kison didn’t feel right about their product, so they started going back to the drawing board and had a meeting with his team again. 

What helped Kison realize that their product was not going in the right direction was this one person who was a marketing expert. One day, this person asked Kison, “I really want to check your business model. I want to check your business model and make sure the economics work; otherwise, you’re gonna waste a lot of money.” The person cited some minor problems, but even if these were minor, this pushed Kison to look at a different angle. Then, he indeed noticed that something was wrong with their product.  


3. Spend the time to understand who you’re trying to sell your product

Kison specifically pointed this out. He said if there is one thing he must teach the young entrepreneurs, this would be it. New entrepreneurs tend to have a lot of amazing ideas and prototypes that can become a global sensation in the market. 

You get an idea, and you’re super excited about it. You hired professionals to build it. You posted it on the market thinking that people would go crazy about your amazing idea, yet you got surprised as no one bought your product. It turns out that there’s already an existing product that offers the same functions as your product, has better quality, and is way cheaper than yours. 

This is why spending some time understanding and pinpointing who you’re trying to sell your product is very important. Spend some time interviewing your potential customers and ask them personally what their problem was and what could solve it. 

For example, you go out and ask people what their problems are with their sofa. Some would say it is hard to clean; it is not that soft, and others would point out that their sofas get torn out easily because of the cold and sometimes hot environment. After hearing these problems, you would then invent a sofa that is easier to clean, super soft and comfortable, and very durable that could withstand the hottest summer and the coldest winter. 

With that, you already have buyers waiting in line to buy your product because you solved their problem. You can do a series of these interviews. Let this be a challenge for entrepreneurs to try and do about 40 of them, and there’s a guarantee that this technique will sell your products instantly. 

Personal interviews with 40 people are effective because it’s not quantitative analysis. You’re not looking at a bunch of numbers on a spreadsheet and trying to analyze the probability or the percentage of your success. You are doing qualitative research where people tell you their problems regarding this product. If most of your interviewees have the same problem, you make a product that solves that problem, and automatically you have 25-30 customers waiting for your product to come out. 

Kison also stated, “You have to be very proactive about it. It doesn’t cost you money, it costs you time. Spend the time to do it. You learn so much you learn a lot about the problem you’re solving. You learn how to speak about it better articulated in the prospect or customers voice goes too far.” 

Then if you got to the point where your investors or partners don’t believe that your products will get sold in the market, you could easily persuade them by saying you already did 40-50 personal interviews. You are 95% sure that there are people who will buy your product. If you can already sell your product even before building it, that is your cue that you are in the right direction. 

So going back to the story, Kison and his team went back to the board and realized that they didn’t have a targeted audience yet. They were so caught up with their idea that they forgot the most important factor when you are in the business industry: the customers. 

So their first big challenge was how they would acquire their customers. Kison knew someone who worked at a reputable bank, and he thought that he was going to be their first customer, but Kison’s friend replied, “No way we’re not putting 100 plus million dollar transaction on this platform.” Kison continued looking for customers; he knocked on doors and went to LinkedIn to pitch their products. After weeks of searching, Kison was able to look for his first customer. 

There was this one investment banker named Felix, and he was amazed by the idea of Kison’s product. Kison also told Felix that there is a prototype already, and they are now focusing on changing the model of the product for it to work. Felix was thrilled, and he told Kison that he wanted to meet with him personally. 

So, Felix went to Kison’s town and talked to him. When Felix and Kison met, Felix told Kison, “Do you want do you want me to put you on this?” Kison replied, “Yeah, I like that. This is what we’re looking for.” Felix offered them an Initial Public Offering, and it was $400 million worth of IPO. That was really huge for Kison, so he didn’t want to let go of his potential customer. 

After that conversation, Kison flew to Felix’s hometown and had dinner together. They went to a Steakhouse in Chicago, and they were doing business while establishing a professional level of relationship. While Kison and Felix were in the middle of their conversation, Felix received a phone call. He picked up his phone, and Kison got shocked after hearing the conversation. 

Felix replied to a voicemail from his client and said, “Hey, I already got a solution for the mid data management, blah, blah, blah. Send Kison a contract over because they’re interested and you know, they’re ready to pay that whatever amount we agreed to.” Kison was shocked because he only expected a dinner, but it turned out that there was already a deal that was closed during their dinner. 

But this wasn’t a bad thing for Kison. In fact, he was very happy. Felix was so nice, and Kison liked him because he knew that they were just a small startup. Kison also felt Felix’s empathy because Felix also experienced what Kison went through. Felix funded Kison’s project because of its involvement in the IPO. They had enough budget to finally finish their product and fix minor problems. 

Everything worked out well, and the transaction went smoothly. Kison went through the process for the first time, and they learned many things about working with a professional company during the onboarding. The deal took place, and everything went well until Kison had another client. This client reached out to Kison and said, “Hey, I actually use your software working on that deal right there.” He added. “I’m in this new role, and we need to get software like yours.” 

Kison was really excited, and he accepted the offer. They went through the wholesale process. Kison showed this new client a demo, they were thrilled, and they liked the idea, signed contracts, and things started well with them. This was important for Kison because this was potentially their biggest client with over a large billion-dollar fund. 

Kison and his team were pretty excited. They were already talking about the pricing, but what happened next is truly horrifying. Kison received an email from this new client saying, “Hey, my permissions just changed. You know, they just, like changed on their own.” Kison replied, “Oh, that’s weird. What are we talking about?” 

Shortly after that, Kison checked the product, and it turned out that someone or something reset this new client’s access. They looked for the problem, and Kison found out that it was a bug. Kison immediately worked with his developers and got rid of the bug. Kison then told this new client that everything was now good. Their new client responded, “Well, do I have to worry about this happening again?” Kison replied, “No, no, you don’t have to worry about this happening again. We got it under control.”

One of the interesting things about Kison’s situation is that a software developer realizes and always expects bugs to happen, which is not such a big deal. The software developer can look for ways to fix this like it’s just part of the normal course of their day. But when you work with clients who are not that techy, they would treat a bug like it’s the end of the world. 

People that are more hands-on in managing the transaction and who are really under the gun are the ones working the hardest, working a lot of the critical tasks, a lot of the tactical TAs, late nights, they’re really grinding it out, and they’re carrying the burden of what’s at stake. Those people understand, and they are not hard to deal with. 

Luckily for Kison, this new client was not ignorant of modern technology. The client knew that bugs are always expected, and she trusted Kison that they had already removed it. 

So Kison told this new client that the bug was taken care of, but 2 or 3 days later, the bug occurred again, and the client got a reset on her account again. Kison was shocked, and he was trying to quickly fix it to avoid getting ashamed. 

He immediately told his team that there was a bug, but most of his team are from the Philippines, and they don’t have the same time zone. Nothing’s really getting done until his team gets up early and immediately tries to help address the issue. Kison’s team fixed the bug, but still, on the next day, it kept on coming back. 

Kison’s team was still the same. He was a senior engineer, a slash senior, and the CTO lead developer. No one in his team is really an expert at fixing or completely eradicating this bug. Even if Kison wanted to look for a new member of his team, he wasn’t completely sure which of them he would let go of because he had a good relationship with his team. 

However, the client’s situation kept getting worse and worse every day. Kison was confused about what he should do, he was down, and it came to a point where Kison took an envelope and wrote a note saying, “I’m really sorry for the experience you’re having. At the very least I owe you a night out.” Kison placed $200 into this envelope and mailed it off to this new client. 

That’s how bad Kison felt, and that was how hopeless he was. Kison didn’t know what to do during that time, and he didn’t have complete control of the situation. He and his team were all doing their best, but they just didn’t have the skill set to finish the job. 

Kison got the recruiters running around looking for him, he was interviewing folks, but some of them were not confident in joining the team because no one wants to ride a ship that is on the verge of sinking. Kison had six or seven people during that time, and they were all gathered in Kison’s condo. They had an office prior to that, but Kison decided they needed a new environment to strengthen the team’s bond and have an even more healthy working environment. 

Kison really established a good relationship with his team, but he only had one person working and fixing the bug. There were a couple of interns helping in fixing the bugs but still, they weren’t enough. But when everything seemed lost for Kison, a miracle was waiting for Kison in the elevator. 

Kison went back to the condo after looking for solutions. When he was inside the elevator, this one person was with him and asked Kison, “Hey, what floor?” Kison told him that he was going to the 30th floor, but when he looked at the numbers, he noticed that the person had already clicked the 30th floor. So that was the only time that Kison realized that they were neighbors on that floor. 

Kison and this guy started talking to each other, and Kison shared with this guy that he runs a tech company and was using his condo unit on the 30th floor as their office. 

When they were about to part ways on the 30th floor, Kison said to this guy, “Hey, by the way. If you know somebody that is a developer that knows AWS, at this point, we realize there’s a lot of system admin problems. It’s kind of the crux of the problem. So if you know anybody, it’s like AWS system admin. You let me know.” 

Shockingly, this guy looked at Kison, gave him the one eyebrow raised, and told him, “I actually happen to do that.” This was a miracle for Kison, and he was really happy that someone would finally have the chance to solve the bug problem. Kison immediately explained to this guy the situation, and he told him that he could hire him on contract immediately and start solving these immediate problems. 

The guy in the elevator didn’t hesitate to agree and helped Kison with his problem. Kison created a small contract because he thought that the bug was the only problem and this new guy’s work would only be for 2 or 3 days. But when Kison thought everything was going well again, he got hit with another problem. 

This new guy told Kison, “Hey, you got a lot of spaghetti code here. And this stuff really needs to be reworked. This is the kind of stuff you’ve been iterating on and building on top of each other. And it’s not even a way that a normal programmer can really follow. So even if you try to grow, you can’t even add people that can help grow this because it’s just so confusing for them to learn. And essentially, you need to rebuild this application with more of a microservices architecture. So that you have as you grow, you add different capabilities to your product. You break it out so they work modularly and one thing doesn’t break the other thing.” 

This means that Kison needs to look for professionals who will finish this product because if they kept tampering with this product with less knowledge, this product would be going nowhere but the trash. So, Kison was really facing a huge dilemma. 

Should he fire his team with whom he had established a good relationship and hire professional workers to finish the job, or should he just stick with his team and abandon his potentially huge client. 

Before he decided, Kison shared that he really had a good relationship with his team members from the Philippines. They built a great camaraderie with each other. Kison also shared that he traveled to the Philippines just to have teambuilding with his employees. Kison spent a month in the Philippines and made some trips there. They went on annual dive trips, island hopping, snorkeling, did fun activities on the beach, and did a picnic. 

He really had an amazing and jolly team, which was why it was really hard for Kison to choose what he should do. Kison asked his old team what they should do, and all of his employees agreed that Kison needed to hire professionals to finish the task. 

They understood that they were building a dream house. Kison and his old team were successful in finding the best location for this dream house. They all knew that that was the right spot for the house to be built, but the problem was they could not build the house on their own. They helped Kison figure out the perfect location for the house, but they accepted that they weren’t capable of building the house, and Kison needed professionals to build their dream house. 

Firing someone isn’t always negative. His team members were okay and were willing to get fired just so experts could finish their product. They know that they cannot do it, and they need real professionals to do the work. So even if they had amazing chemistry and the team was a happy team, firing them was a good decision for him to finish the product. 

Kison then decided and started looking for different talents to help fix his product. Kison ended up hiring high-caliber engineers and professional workers with an excellent skill set and transformed his team from junior to intermediate level instantly. So Kison magically transformed his team into senior-level engineers. 

Kison’s new workers knew how to write codes for scale, knew about the bugs, knew about the updates, basically everything they had been working on for months. His new team completed it in 2 days. The project was done all because Kison parted ways with his old team. 

But this wasn’t a bad ending because, unlike others, no one was angry or depressed from Kison’s old team. His team understood the problem, and they still helped Kison solve it. There was no bad blood between them. In fact, Kison and his old employees are still keeping in touch with each other to this day. 

This story is filled with lessons not for employers but for bosses and CEOs. I know that these people are often prideful and don’t admit their mistakes, but bosses and CEOs have to acknowledge that these lessons will make them even better bosses. Admitting mistakes is an uncomfortable matter for CEOs and employers, but in this episode, the conversation is getting comfortable with the uncomfortable conversations. 


4. Have a tight feedback loop

One final lesson that Kison left for the listeners is the importance of establishing a tight feedback loop with your customer, workers, and even your bosses. 

You must have a strong feedback loop with your customers to figure out what you need to change, continue, exactly what their issues are and how to resolve them. 

Next, you’ll want to set up a feedback loop with your employees. You must constantly offer them a rating of their work. It doesn’t matter whether the feedback is nice or bad; you must share it with them. First and foremost, you must help them understand that providing criticism is not intended to be used against another person, just as getting bad feedback is not anything to be embarrassed about either. 

Giving feedback may be done in various ways, some of which are better than others. It is up to you as the CEO of your firm to decide which course to go. Is it more important to prevent controversy by delivering only good feedback? Or would you take a stand and advise your employees to consider criticism as a learning opportunity. It’s also important to seek methods in which you can make your team feel at ease giving you feedback, even if you’re the company’s boss. 

Employees may be reluctant to provide feedback to their executives for fear of being fired if they do. That suggests you’re not doing a good job if your employees don’t want to tell you what they think. In other words, you’re sending a message to your team that you’re in charge, not them. 

While a boss commands by waving a finger, a leader empowers others to accomplish their goals while keeping tabs on their progress. It’s time to reassess your leadership style if your staff isn’t treating you as a person they can approach. Maintaining a healthy work environment is one of the most important aspects of running a successful business. 

For the sake of completeness, Kison was able to let go of his old team, who had worked with him for many years, and established a good relationship with and employed new people to finish the project. In this story, there were many lessons to be learned. Remember them all, and we’ll see you again on the next edition of client stories.


This article was based on Episode # 25: Kison Patel’s Story, please watch the complete episode here!