Making of a Manager & Crucial Conversations

I have two go-to books for anyone who wants to be a tech manager:

The Making of a Manager: What to Do When Everyone Looks to You by Julie Zhuo
Crucial Conversations: Tools for Talking When Stakes are High by Kerry Patterson

What I like about the first book is that makes you feel like you can do it! The hardest part of being a leader is the nagging feeling that someone should be doing it. Even after years of experience, of seeing people I admire and put on pedestal fall of it and reveal themselves to be fulling functioning and flawed human just like the rest of us, I find it helps have a cheerleader somewhere behind me saying โ€œGo on, you can do thisโ€ and Julie Zhuo does a great job of that interspersed with practical advice on managing people. The second book, Crucial Conversations effectively teaches you how to do what julie Zhuo does so well in her book. Kerry Patterson outlines when to see you are having a crucial conversation and then gives practical advice on how to frame these conversation in a way that empathetic, clear, and tackles the problem in a non-emotive way that facilitates conversations rather than placing barriers to response.

This is a good summary I found:

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ChatGPT Enterprise

ChatGPT was released to the public a couple of days before we created a policy for how engineers engage with the tool. I am 100% behind using any tools to solve problems and speed up delivery, but keeping possession of our Intellectual Property is also important. Even more important in the credit and collections industry it is critical that we safeguard personal information as much as humanly possible. Having data in Europe or UK the important, keeping on our own cloud services is ideal. There are some real challenges with compliance with channels like WhatsApp when they want to move data to the US.

It will be interesting to see how far Enterprise ChatGPT goes with addressing these concerns.

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T-Shape or H-Shape Skills Set

Being a CTO requires a diverse set of skills. Career advisors often refer to building a “T-shaped” skill set, where you possess in-depth knowledge of a specific skill while also having a broader but less detailed understanding of various other skills. In the case of being a CTO, it usually begins with a deep practical technical expertise. However, as time and one’s career progress, some of those practical skills may diminish, making room for a broader yet less detailed technical knowledge. The most challenging part of this transition is often the need to deepen your business skills.

For me, this journey has involved learning more about legal aspects, budgeting, accounting, HR and people management, project management, leadership, communication, the industries I’ve worked in, negotiation, stress and cognitive load management, risk management, and the list goes on. It leads me to wonder if my career is evolving into more of an “H” shape than a “T,” with deep and extensive IT and engineering skills, along with substantial business knowledge. Then, when I reflect on the skills I’ve developed, communication skills seem to be the most crucial and profound. This encompasses written communication, skills for framing “crucial conversations,” empathy and understanding, as well as tactical skills for knowing what to say and when.

So perhaps I am a “T” with serifs: deep technical skills, a broad range of other skills, and a dip representing business knowledge and communication. Or maybe communication is becoming my primary skill now. What are your thoughts? Is your skillset more of a “T” or does it lean toward an “H”?

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๐—ง๐—ต๐—ฒ ๐—ฃ๐—ฒ๐—ฟ๐—ถ๐—นs ๐—ผ๐—ณ ๐˜๐—ต๐—ฒ ๐—ก๐—ผ๐—ป-๐—ฅ๐—ฒ๐—ฎ๐—ฑ๐—ถ๐—ป๐—ด ๐—˜๐˜…๐—ฒ๐—ฐ๐˜‚๐˜๐—ถ๐˜ƒ๐—ฒ: ๐—ฆ๐˜๐—ฎ๐—ด๐—ป๐—ฎ๐˜๐—ถ๐—ผ๐—ป ๐—ถ๐—ป ๐—Ÿ๐—ฒ๐—ฎ๐—ฑ๐—ฒ๐—ฟ๐˜€๐—ต๐—ถ๐—ฝ

๐—ง๐—ต๐—ฒ ๐—ฃ๐—ฒ๐—ฟ๐—ถ๐—น ๐—ผ๐—ณ ๐˜๐—ต๐—ฒ ๐—ก๐—ผ๐—ป-๐—ฅ๐—ฒ๐—ฎ๐—ฑ๐—ถ๐—ป๐—ด ๐—˜๐˜…๐—ฒ๐—ฐ๐˜‚๐˜๐—ถ๐˜ƒ๐—ฒ: ๐—ฆ๐˜๐—ฎ๐—ด๐—ป๐—ฎ๐˜๐—ถ๐—ผ๐—ป ๐—ถ๐—ป ๐—Ÿ๐—ฒ๐—ฎ๐—ฑ๐—ฒ๐—ฟ๐˜€๐—ต๐—ถ๐—ฝ

In today’s fast-evolving business world, “knowledge is power” holds paramount importance. Yet, some boardroom leaders neglect regular reading. This non-commitment to knowledge not only limits their personal growth but jeopardizes entire businesses, especially in sectors like credit and collections.

๐—ง๐—ต๐—ฒ ๐—–๐—ผ๐˜€๐˜ ๐—ผ๐—ณ ๐—ก๐—ผ๐˜ ๐—ฅ๐—ฒ๐—ฎ๐—ฑ๐—ถ๐—ป๐—ด

๐˜”๐˜ช๐˜ด๐˜ด๐˜ฆ๐˜ฅ ๐˜›๐˜ณ๐˜ฆ๐˜ฏ๐˜ฅ๐˜ด: In industries like credit, understanding market dynamics and regulatory shifts is crucial. Reading provides depth that briefings can’t match.
๐˜•๐˜ข๐˜ณ๐˜ณ๐˜ฐ๐˜ธ๐˜ฆ๐˜ฅ ๐˜—๐˜ฆ๐˜ณ๐˜ด๐˜ฑ๐˜ฆ๐˜ค๐˜ต๐˜ช๐˜ท๐˜ฆ๐˜ด: Reading offers diverse viewpoints, fostering empathy and creativity.
๐˜”๐˜ฆ๐˜ฏ๐˜ต๐˜ข๐˜ญ ๐˜ˆ๐˜จ๐˜ช๐˜ญ๐˜ช๐˜ต๐˜บ: Reading sharpens cognitive abilities, enriches analytical thinking, and aids clear-headed decisions.
๐˜Š๐˜ฐ๐˜ฏ๐˜ต๐˜ช๐˜ฏ๐˜ถ๐˜ฐ๐˜ถ๐˜ด ๐˜“๐˜ฆ๐˜ข๐˜ณ๐˜ฏ๐˜ช๐˜ฏ๐˜จ: Top executives, from Bill Gates to Oprah Winfrey, use reading for perpetual growth.

๐—ง๐—ต๐—ฒ ๐—–๐˜‚๐—น๐˜๐˜‚๐—ฟ๐—ฒ ๐—ฎ๐˜ ๐—ฆ๐˜๐—ฎ๐—ธ๐—ฒ

A non-reading leader risks cultivating a culture of stagnation. If the helm doesnโ€™t value learning, the entire organization may follow suit, stunting innovation and growth.


In our rapidly changing world, leaders have a duty beyond profit-makingโ€”it’s setting a growth precedent. Not committing to reading risks stagnation, a gamble no business can afford.

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Aligning Business with Technology

Aligning business with technology seems like it should be the simplest task in the world. Yet, it’s astonishing how challenging it can become. Often, it feels as if the tension arises from balancing cost against quality, or in defining UAT metrics that engineers can aim for. However, the issues can be much subtler than they appear.

Several years ago, before Webio, we worked on a webchat widget that utilized intent recognition to decipher customer inquiries and deliver appropriate responses. We dedicated considerable time and effort into training an IBM Watson data model to understand these questions and offer the answers. Concurrently, we developed an agent console to facilitate these conversations. All this was undertaken within an innovation lab, which aimed to revamp an outdated platform.

We pursued both tasks with enthusiasm. We located datasets, trained the AI, constructed workflows, and refined our strategies. We also determined contracts, calculated costs, and simultaneously, developed a state-of-the-art (for its era) extensible, restful API agent console, employing every conceivable framework and library to ensure its excellence.
Eventually, we secured a client. During our meetings, the client expressed significant excitement about becoming one of the pioneers in their industry to adopt this AI technology. Upon completing the product, we showcased it. The AI performed impressively; its intent recognition was almost flawless, save for the rare misunderstanding.

However, a pivotal moment came when one of the senior managers, who had been our staunchest supporter, assessed our work. She commended our achievements but then posed a simple question: “Wouldn’t it be easier for the customer if we just used buttons instead of intent recognition?” And she was unequivocally right. It simply streamlined the process. Consequently, we chose to retain the AI, but relegated it to a backup role, favoring a menu-driven interface. The overriding metric for success was usability, and this change aligned with that goal.

From that experience, I’ve consistently employed a balanced approach: using intent recognition for intricate queries and opting for buttons when only a few common questions are anticipated.

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In a very subtle way, FigJam has radically transformed our approach to software planning. Special kudos to David Power, our Dev Experience Lead, who recognized its potential for R&D during a management course and championed its adoption. Figma has been a popular tool among UX and design teams for some time. FigJam, however, is a hybrid between Figma and tools like Visio or Lucidchart. What sets FigJam apart is its user experience, which is highly conducive to the free flow of ideas, making it particularly effective when groups of engineers are tackling complex problems. Its use of bright colors, stickers, and curved lines creates a more creative and friendly environment, avoiding the rigid, technical feel that can hinder idea generation by demanding perfection. While rigid diagrams are still necessary, especially for working through specific details and helping with compliance, FigJam strikes the perfect balance for planning stages.

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On Diversity

Diversity in hiring might be the single most important aspect of building an innovative team.

A few years ago, I was lucky enough to go to Dalian, China (not far from the border with North Korea) and work with a team there. The office was in Dalianโ€™s tech quarter, and on approach, you could tell you were in the tech quarter because almost immediately the style of clothing, the posture, the shops and cafes, all began to look depressingly similar to any tech quarter you might see in London or Paris or Berlin or Vancouver or Ottawa or New York.

This got me thinking about diversity. Up to then, my thinking has always been about building diverse teams in terms of gender, LGBTQ+ representation, and a good cultural mix. But I then realised that this really isnโ€™t enough. People tend to view and see the world the same if they share a salary structure (paid monthly for example), similar values (all went to university), and a common language (everyone has English in common) and common neurological traits (engineers), which means if your hires have a good representation across genders and ethnicities, you may not get the diversity you need to truly innovate.

At Webio, where our primary focus is on the Credit and Collections industry, often it helps us to explain to engineers what the realities are for someone who is paid weekly, or not at all if they injured themselves, or the experience that someone has if their only access to IT and the internet is through a phone and a limited data plan but engineers that have lived that experience just ‘get it’. Similarly, very few engineers have a lot of insight into the experiences of people with sight, hearing, cognitive, or mobility barriers, yet so often it is understanding these โ€œedge casesโ€ which is so critical to innovation. You cannot come up with something new by having the same people doing the same thing!

Once a diverse team is assembled, the next innovative key is to make sure that they stay diverse, which means letting each of the team members grow and experience and think in their own way, and not try to funnel everyone into a common corporate culture that encourages groupthink or try to mould people into your ideal. This isnโ€™t as hard as it sounds, as long as you can let go, avoid the need to micromanage, and focus on building on peopleโ€™s strengths rather than trying to break them of their weaknesses.

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“Amateurs talk about tactics; professionals study logistics”

“Amateurs talk about tactics; professionals study logistics” might be one of my favorite quotes despite no clear attribution to who may have said it. But as a CTO of a tech company trying to develop software for the Credit and Collections industry, it is a constant theme. From a strategic perspective, we dream of an automated assistant that works with creditors and the people they service to enable everyone to have the financing they need and to stay in control so their debt does not spiral. On a tactical basis, this means looking at the different maturity models for innovation in AI and messaging, this means building robust and modern RESTful APIs and WebApps that can be used to integrate the channels that our clients’ customers are on and to automate as much of those messages as possible. But logistically we have to work with what we have and recognize that different companies are at different stages of their digital journeys. This means making sure we can accommodate the use of SFTP where possible, being mindful that even the smallest interface changes can have a profound impact on call center productivity, and making sure that everything we do is aligned with the latest requirements in terms of the FCA, GDPR, and any other applicable regulatory framework. Every company needs a strategy, needs the tactics to implement that strategy, but the best strategy will always hang on the logistics!

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Meetups and Engagement

Engaging with tech and business communities is important, engaging with the right communities is critical. As a tech leader it is important to balance technical knowledge with industry knowledge. Meetups are a great way to do this, at the moment my go-to group is the Nottingham Data Science and AI meetup which has a great mix of particle and theoretical AI workshops and talks.

I also spend some time on the Tech Nottingham and Irish Tech Community slack groups and have found CTO Craft group a great way to keep abreast of tech leadership trends and issues.

What are your go-to places for industry news and community?

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