The Best Leadership Books I Read Last Year

6 Recent Reads That Have Impacted My Approach and Thinking as a CEO 

I’ve been a reader my whole life. I practically read a book a day when I was a kid (all fiction, of course!). As I got older, life got busy, and I had less time for fiction. I was starting a career in software development and learning as I went. After a few years in the field, I decided to focus less on reading tech-focused books, which I was fortunate that my job gave me the time and opportunity to do, and start reading business books. Before long, I formed a habit. I was always looking for the best business and leadership books that would help me, and later my teams and my company, grow. 

Today, the books I consume continue to shape how I approach solving problems, making decisions, and building relationships. However, I realized last year that I now read almost entirely leadership and business advice (see my 2022 reading list, for example). As a result, I vowed to expand into more genres. While I still haven’t spent much time back in the world of fiction (though over the holidays I started reading Andy Weir’s Project Hail Mary at my teammate’s recommendation!), I did add biographies into the rotation. At least I’m getting more of a story! 

The 6 Best Leadership Books I Read in 2023

If you’re looking for your next read or a gift for a business leader in your life, here are a few of my recent favorites.

Four Seasons: The Story of a Business Philosophy

By Isadore Sharp

This is an inspiring story of a seemingly ordinary person–a child of immigrants and a son of a builder–doing extraordinary things. Isadore Sharp, the founder and chairman of Four Seasons, shares how he developed a brand now known worldwide by following his gut, taking big risks, persevering, and committing to his vision. You’ll learn where he drew inspiration and ideas from and see the power of asking for what you want. Sharp’s memoir also reinforces the importance of building relationships, earning trust, and being true to your word.

Building a Second Brain: A Proven Method to Organize Your Digital Life and Unlock Your Creative Potential

By Tiago Forte

This book isn’t just one of the best leadership books I read this year–it’s one of the best all-around books on this list. Everyone can benefit from this, and I certainly took a ton of notes! Building a Second Brain is full of practical tips for those of us juggling to-dos and information for our teammates, clients, loved ones, and more. The techniques will help you remember, capture, organize, distill, and express your ideas, notes, and work to maximize the value and impact on your life. The book can also guide you in deciding what information to keep and what to let go of. Reading this has helped me be more systematic and strategic in both my personal and professional life. Shout out to my friend and fellow CEO, Patrick Patterson, for this sanity-saving recommendation.

The Power of One More: The Ultimate Guide to Happiness and Success

By Ed Mylett

In this motivational book, Ed Mylett urges us to keep pushing when we would otherwise stop. He emphasizes how much we stand out and achieve when we are willing to go above and beyond expectations. Take the additional meeting. Do one more round of practice. Over time, this philosophy will pay off in surprising ways! (Haven’t heard about Ed Mylett? Look up some of his talks on YouTube for a preview of what to expect with this book!) 

Boundless: A New Mindset for Unlimited Business Success

by Henry King and Vala Afshar 

King and Asfhar draw on years of experience leading digital teams and transformation initiatives to outline a path to business success. The pair focus on how to overcome silos inside your organization to enable the free flow of information and resources. The book focuses on seven areas: connection, integration, decentralization, mobility, continuity, autonomy, and shared success. I’m fortunate to know the co-authors in real life and know that they also practice what they preach!

Soundtracks: The Surprising Solution to Overthinking

By Jon Acuff

Are you an overthinker? Don’t worry – you’re in good company! We’ve all occasionally fallen into the pattern of overthinking. This book is an easy read that prompts you to examine the soundtracks (the thoughts) that repeat in your head. It then provides a guide to help you change what your brain tells you. Once you take control, you get back time to accomplish what you want while also unlocking your creativity in productive ways.

Titan: The Life of John D. Rockefeller

By Ron Chernow

Titan is a fascinating look at a person with an incredible impact on industry in the United States. It’s a very long read (or listen, in my case), but I kept coming back to it throughout the fall and winter. This biography examines the rise of an ordinary man to immense power and, along the way, reveals how so many things we take for granted first came to be. If you’re interested in American history and business (and it all really wasn’t that long ago!), I’m certain you’ll enjoy this book.

Want to share the best leadership books you’ve read?

Send me a note on LinkedIn – I’m always open to recommendations, and your book might just make my next list. Happy reading!

How to Win Big with Your Customer Experience

It’s all about the customer journey!

In a world where customers are demanding value for every penny and the economy is challenging to say the least (recession? best job market ever? both?!), your edge isn’t just in top-notch products or services. It’s in unforgettable experiences that turn heads and open wallets. Remember this: In today’s fierce market, leading with customer experience isn’t just a good strategy; it’s the golden rule.

Schools, stores, banks, name any type of business — targeted, personalized experiences are central to the success of every online, in-person, or hybrid offering. And personalization can’t happen without truly knowing your customers and users. You have to start with understanding their journeys. Examine everything from their vital tasks, preferences, and pain points to their moments of happiness and delight. Effective personalization and engagement is impossible if you don’t know what your customers are doing or how to meet their needs as they move throughout each day.

To increase engagement, start with…

Providing a holistic journey-driven customer experience

As you look to differentiate your brand, widen your view to consider the whole user journey associated with your offering. You may find overlooked opportunities early or late in the life cycle. At these touchpoints, you may be able to do more to build ongoing (perhaps even lifelong) engagement and advocacy.

To create a stand-out customer experience, some organizations are integrating with other services, offerings, and products — even those from outside organizations. For example, I appreciate that my favorite hotel chain has updated their app so that in addition to accessing hotel services, I can use their app to find nearby restaurants, book a reservation, and schedule an Uber pick-up to get them there. Is it that hard to copy and paste into the Uber app? Of course not. But, when on the go, these little conveniences inspire disproportionate gratitude and brand loyalty. Financial transactions are another place I see companies use this tactic, offering products that enable easy options like buy now, pay later at the point of purchase.

As you work to create holistic, frictionless user journeys, team and departmental silos inside of organizations often slow change makers like you down. Beyond trying to break down those barriers, you can also look to build (or buy) a digital experience layer that wraps around organizational silos and their disparate systems, such as providing single sign on and a consistent but personalized customer experience.

Adapting to new customer preferences

Everywhere I look, customer preferences and expectations are evolving. Chief among these changes is that customers expect products and services to be accessible whenever and wherever they want them. This goes beyond simple mobile and digital offerings. “Buy online, pick up in store” has become table stakes. Now, the point of purchase / point of sale is moving towards the customer’s house, whether through virtual consultations and support, Uber eats delivery, or in-home health care concierge services.

I’m also seeing growing demand from consumers to manage their own relationships with businesses and schools. In many ways, increasing self-service can be a win for all. Customers get what they want, and organizations can cut IVR/customer support costs and free up staff to focus on higher-level problems.

Personalizing products and services

As mentioned earlier, one-size-fits-all products and services no longer cut it in education, retail, healthcare, or anywhere. Customers seek unique products and personalized offerings. Of course, you’ll need to balance new feature development with cost. The choices you make here must be driven by the customer. Increasing personalization usually also requires selecting and investing in new (often automated and/or intelligent) technologies and configuration tools. This in turn requires developing and launching new policies. To ensure they’re maximizing and accelerating ROI, many organizations are looking to outside technology consultants and change management experts like my team at Robots & Pencils for guidance on these strategic decisions.

Strengthening relationships through content & communication

Outstanding content and timely communications are another way to build brand loyalty, engagement, and community. The first step in creating this content is understanding what info users need. You also want to get clear on when and how to present it during their journey to catch their attention. The final part is figuring out how to deliver this content at scale while maintaining personalization and localization. Automation and data and system integration will be a key focus of any project in this space. This data capture also helps to enable the adoption of new AI solutions that are creating huge impact throughout the organizations embracing them.

Want to talk more about the customer experience? Join us as we explore all of today’s top business and tech trends!

Request an invite to an upcoming Digital Trends Executive Roundtable, where innovators and industry leaders will join together to discuss their biggest priorities and challenges!

—PS: You may have noticed that this blog echoes my recent post about employee experience and efficiency. That’s intentional! I see massive overlap in consumers and employees looking for easy-to-use tech that meets their needs exactly when and where they arise. The companies that will excel most are the ones that care about both the employee AND customer experience.

This CEO report was written by Tracey Zimmerman, President & CEO of Robots & Pencils.

Employee Efficiency Accelerators

The Power of Empathy, Automation, and AI

In boardrooms, exec touch bases, and nearly every client call I’m on, everyone’s thinking about how to supercharge employee efficiency and reduce costs. Organizations are on the hunt for tools and processes that let them accomplish more without pushing employees to the brink or blowing their budgets. Every good solution I’ve seen has started with an empathetic view of the employee experience. Which tasks are unnecessarily hard? What bottlenecks slow people down? What can you automate and streamline to help your team? Where can AI scale human potential and cut spend? The answers to these questions will point the way to powerful savings and efficiency opportunities.

(This is blog 3 in a series on key priorities for business and tech leaders. In my last blog, I talked about digital modernization, including integrating data and systems–which everything I’m about to discuss will 100% require!)

Reimagining experiences around employee needs

Outdated tools and processes that were built largely around organizational silos are hurting productivity. But it’s not as simple as replacing old tools with new ones. First, you have to understand what your employees actually need!

This requires looking at how different types of team members spend their days. What are their most important tasks and how are they getting those things done? Sometimes, you’ll find a need as simple as additional training or upskilling. In other cases, you might find opportunities to improve communications, tweak processes, or introduce new tools. One need I see frequently (with our clients and as a consumer) is more flexible, user-friendly tools for employees in the field. Your workers should be able to access and share information and complete critical tasks wherever they are. Whether on a remote job site, at a retail counter, meeting with a potential customer, or simply working from home, everyday duties shouldn’t require extraordinary effort!

On the flip side, better understanding how your employees work can reveal where you’re wasting time and money on tools your employees don’t actually benefit from. Frequently we find two (or more!) systems where only one is needed. Eliminating and consolidating systems can be an easy way to directly improve your bottom line.

Once you address and focus on your team’s real needs, you’ll quickly see cost savings and employee efficiency rise. Gains in engagement, productivity, and retention will follow. Ultimately, you’ll be helping your employees to ensure better customer and student experiences, providing a win all around.

Empowering employee efficiency with self-service tools

After so much frustrating supply chain disruption and constantly fluctuating prices, consumers are paying super close attention to product and service reliability and pricing. This means we as leaders must focus attention on internal predictability and employee efficiency. Yet, I still come across employees unable to complete routine activities without assistance or permission from management, IT, or other overburdened departments. These employees require increased self-service features. While a real need for oversight or access limitations can exist, unnecessary permission bottlenecks have to go. From employee-led shift swapping to going beyond dashboards and reports to insights and suggestions, your employees need easy-to-use technology that allows them to take ownership of their work and operate without constant disruption.

Automating processes to free up teams for higher level work

In many organizations, highly manual (and painful!) workflows have led to incoherent data and inconsistent results. These problems requires an intentional shift towards repeatable processes with automation at the forefront. When you free employees from these time-intensive tasks, they can refocus on higher value work that benefits your business and customers.

Automation can also reduce acquisition costs and increase the long-term value of each connection. Education specifically has a large need to increase marketing efficiencies and automate communications across the student journey. Rather than relying on overloaded staff (particularly for straightforward messages and reminders), institutions can use automation to deliver the right information to the right learners at the right time in their journey. But watch out! Carefully designed, these automated flows can be delightful. When done poorly, it can cost you the trust of your customer, which is never cheap to rebuild.

Initiating AI-human partnerships

New AI tools are launching at a whirlwind pace, and I’m so excited to see businesses putting them to use! AI-human partnerships promise to accelerate product development, helping with everything from sorting user feedback, to writing Jira tickets, to coding with GitHub’s copilot.

Scaling support services and monitoring customer sentiment is another huge opportunity for using AI to increase employee efficiency. By strategically moving customers from FAQs to an AI chatbot to human support, organizations can scale support services while managing quality and cost as well as directing employee focus to advanced problems.

As for education, there’s ample potential for AI to accelerate staff processes and workflows in areas like:

  • Creating personalized custom experiences (1:1 content) for students
  • Reducing the costs of course design via AI authoring & modules
  • Accelerating presentation creation
  • Delivering student support services with less labor
  • Doing predictive modeling of student outcomes

In every industry, leaders need to think creatively and seriously about AI to stay ahead of the curve. As an internal team or with the support of outside experts, you need to start identifying use cases, setting up governance plans, and working with security and architecture departments to implement intelligent solutions that support teams across the business.

Want to share your thoughts on topics like employee efficiency, AI, and self-service?

Learn more about today’s business and tech trends — and join the discussion at an executive digital roundtable!

This CEO Report was written by Tracey Zimmerman, President & CEO of Robots & Pencils.

From Chaos to Clarity: The Digital Modernization Journey

“Barely controlled chaos in a highly complex environment with fragmented innovation solutions”–that’s how one of our clients recently described their organization. I hear versions of this all the time, so if that’s how you feel, trust me–you’re not the only one! We’re in a time when adaptability and speed are make-or-break, but fragile infrastructure and fragmented data, tools, and processes keep tripping up plans. I see it over and over. It’s why digital modernization is so important.

Organizations need a stronger foundation that makes it easier to extract insights that can really make a difference to business results, to adopt new tech, and to deliver products and services at scale. But building that foundation won’t be a quick or straightforward fix. I’m talking about consolidating your current tech stack, plus introducing new implementations, integrations, and system improvements. It’s a lot! To succeed, 3 areas in particular are going to demand your attention and planning–unlocking data, improving (or replacing!) aging infrastructure, and increasing interconnectivity.

(BTW: This is blog 2 in a series on key priorities for business and tech leaders. My prior blog intros these priorities and other influential marketplace trends.)

3 Essential Elements of Digital Modernization Efforts

Unlocking hidden insights by unifying fragmented data

Most companies struggle with disconnected data and insights spread across systems and departments. When we come into an organization, we routinely find departments trying to solve problems on their own with off-the-the shelf systems (including Excel).

While everyone has good intentions, what happens is that they create tech and data silos across the organization. Eventually, a dozen disconnected applications are capturing (but not sharing!!) similar data. The other challenge many clients face is the sheer volume and complexity of data collected for personalizing customer or student experiences. Data winds up scattered across different teams, files, websites, and systems, stored in ways that are too painful to query or analyze. Yet all this powerful data is just waiting to be unleashed!

As the purse strings tighten, leaders can’t afford to leave those insights untapped or to support disparate systems. And we definitely shouldn’t be missing out on sharing valuable data across teams, where combined with the power of human creativity, new ideas can emerge. Aggregating data so that it is easily accessible is a must-do first step in practically every digital modernization journey.

Organizations need to integrate and scale solutions that work, and ditch the rest. So often I see people throwing good money after a bad solution that’s not working for their business. If you don’t have the expertise in house, find a partner who can help centralize your data and transform this goldmine of information into actionable insights.

Increasing flexibility by addressing aging infrastructure

Tech debt and aging patchwork infrastructure are a real roadblock to innovation and growth. Perhaps the problems resulted from a merger or acquisition, siloed planning, or moving fast while addressing pressing issues (like responding to shifting customer behaviors in a pandemic for example!). Whatever the cause, aging and disjointed systems are holding companies back. It’s time to address that tech debt and commit to digital modernization. Say goodbye to archaic systems in favor of more resilient, flexible infrastructure. But know that lack of clarity around ownership and the impact of system deprecation is almost certain to cause problems. To minimize issues, start by gathering and documenting this info. Having a super detailed and thorough change management plan is also vital!

(A tip from our robots: API layers can help you transition aging tech stacks. Rather than fully reengineering a tech stack from scratch, you can leverage APIs as an intermediary to create consistent access and replace the systems behind the scenes piece by piece, allowing your organization to deal with the change in more manageable chunks.)

Preparing for the future by increasing interconnectivity

One huge positive is that everyone now sees the power of connected data, systems, and “things”. Companies recognize that data surrounds everything, and that data models should be planned intentionally from the start of a project. They’re asking the right questions, like: How will we use integration to connect this data to that data? Can we use sensors to track movement of physical items? How will we ensure data integrity across systems? How do we extract those juicy insights to become a more data-led organization? I’m so glad to see leaders doing this planning up front in their digital modernization initiatives!

In some cases, I see interconnectivity extending even further as companies expose APIs to products and experiences outside their organizations. For users, this opens the door for highly curated end-to-end experiences that cut across multiple tasks and organizations. Of course, creating these experiences is not without challenges, including dealing with data and API inconsistencies. Using AI to translate data between different formats could be a game-changer, benefiting both companies and users alike. Definitely keep an eye on advancements in this area!

Coming up Next…

In future posts, I’ll explore how automation and journey-centered experiences can help with cost reduction and efficiency. Later in the series, I’ll talk about trends in personalization and engagement, plus discuss when it makes sense to seek outside expertise and guidance on your initiatives. Stay tuned!

Learn more about today’s business and tech trends — and join the discussion at an executive digital roundtable!

Business & Tech Trends: A CEO Report

How to Maximize Impact and Future-Proof Your Business in an Ever-Changing World

At Robots & Pencils, I have the amazing privilege of supporting leaders on everything from bringing game-changing new ideas to market to optimizing products and services that have been at the heart of companies for decades. Over the last few years, together, we’ve navigated everything from lockdown, to an influx of customer spending and “growth at any cost” strategies, to preserving cash as we brace for a looming recession. In financial services, education, travel, healthcare, and so much more, my team and I have helped to shape tech and business strategy for everyone from fledgling startups to F500 companies amidst a sea of constant change. With no end in sight–and even more acceleration of technology and societal shifts on the horizon, I wanted to highlight the business and tech trends influencing decisions today–and call attention to 4 strategic areas with the biggest opportunity for organizational impact.

The State of the Marketplace and Technology

Let’s start with what business and tech trends I’m seeing and hearing from friends and clients on the front lines.

Limited Funding

Money is increasingly hard to access. Consumer spending is down. Interest rates are up. With boards and investors focused on operating margin and profitability, every initiative needs a strong business case and clear ROI. Guaranteeing growth through better and more customer engagement is extra challenging right now. As a result, securing funding for those projects has become trickier. Internal efficiency gains are easier to justify investment due to perceived greater ability to control the levers that are needed for impact.

Rapid Change

The speed of change is daunting, and companies are subsequently struggling to select future proof strategies and technology. Further, many companies rapidly selected dozens or more tools during the pandemic to keep business going. Now they aren’t sure what to keep, what to cut, or where to reassess the solution space.

Increasing Need for Flexibility

To provide a runway for innovation, businesses need iterative approaches that flexibly adapt to change. It’s easier to swap out a small thing than a big one–and only make big changes after something is proven to work. Whether for technical architectures, business processes, key partnerships, workforce and talent management (think the gig economy), and even stackable education credentials that may add up to a degree, or not, the desire for flexibility is pervasive.

AI Acceleration

AI is a rapidly emerging tech that has been in the periphery, but suddenly everyone has questions about it thanks first to the release of ChatGPT and now new tools launching literally on a daily basis. Wherever you look, both uncertainty and excitement about its potential are high. (We’ll get into this more in coming blogs!)

Top Business Priorities for Maximizing Outcomes & ROI

Given these business and tech trends, there are 4 areas that I think leaders need to focus on today and into the future to maximize ROI. I’ll intro them here, and, in the coming weeks, expand on each one.

1. Digital Modernization

Companies have launched new tools left and right in recent years, but too often projects are happening in isolation. Leaders need to take a step back to improve the underlying infrastructure and address fragmented data, tools, and processes. But it’s not easy! Getting everything in one place and systems working seamlessly won’t be a walk in the park. However, the payoff is the ability to effectively extract business insights and keep pace with the latest tech advancements.

2. Cost Reduction & Efficiency

Good luck finding a leader not thinking about efficiency right now! Everyone’s looking to automate processes, decrease internal costs, and hit targets without over taxing our teams or budgets. A huge opportunity lies in designing employee tools based on a deep understanding of their experiences and on-the-job needs (and perhaps backed by AI-human partnerships!). These efforts will help you both boost productivity and shift focus to the highest value activities.

3. Personalization & Engagement

It’s all about the user! To meet customer expectations and boost loyalty, companies need more unified and personalized experiences across platforms and touchpoints. To succeed, these initiatives must stem from an understanding of the user and have clear ties to revenue and business outcomes. In a similar vein, schools need better, more connected tools to attract students. From there, they have to keep them engaged with personalized content throughout their educational journey, and turn them into lifelong learners and active alumni.

4. Expertise & Guidance

With so much moving at lightning speed, it’s tough to plan for the future while avoiding costly short-term mistakes. From keeping up with user trends to prioritizing tech investments to maximizing ROI on new products, maintaining the expertise to make all these high-value decisions and plans alone just isn’t feasible. Leaders who seek guidance and support at crucial moments will be better equipped to stay ahead of market change and disruption.

Stay tuned for a deeper dive into these tech trends and strategic priorities — and join the discussion at an upcoming executive digital roundtable!

In my next blog post, I’ll explore how fellow leaders are approaching digital modernization–and the proven methods I’ve seen to navigate the roadblocks along the way. Later in the series, I’ll talk about internal cost reduction & efficiency strategies, approaches to product personalization & engagement, and where organizations are finding outside expertise and guidance most useful.

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An Executive Reading List: The Top 7 Books Our CEO Read in 2022

168 Hours: You Have More Time Than You Think
Laura Vanderkam

The thesis of 168 Hours is that not only do we all have the same amount of time, we all have enough time to do the things we want. Vanderkam advises we re-examine how we actually spend our time and posits that, with some prioritization and rescheduling, we can in fact achieve more than we realize.

The Effective Executive: The Definitive Guide to Getting the Right Things Done
Peter F. Drucker

The Effective Executive is a really good classic read. As the name suggests, Drucker lays out habits and practices essential to business effectiveness. In this book, you’ll get insights on how to manage your time, attention, and priorities, build your strengths, and make more effective decisions.

Wild Problems: A Guide to the Decisions That Define Us
Russ Roberts

Difficult decisions, like whether to get married or divorced or have children, can’t be made by logic alone. They require something more akin to gut or intuition. Often, decisions that are more difficult and less pleasurable in the moment are ones that teach us something about ourselves. They provide a test that can be profoundly meaningful. In this work, Roberts provides a path for navigating these wild problems that are entangled with who we want to be.

Skin in the Game: Hidden Asymmetries in Daily Life
Nassim Nicholas Taleb

Skin in the Game is about incentive alignment and how we think about risk and reward. It will make you think about how you work, how your team works, and how you partner with customers as well as the ways you operate in the world outside of your profession.

Together: The Healing Power of Human Connection in a Sometimes Lonely World
Vivek H Murthy, MD

Written by a former Surgeon General, Together is a treatise on why we need more human connection in our lives. He discusses how social isolation impacts people at school, at work, and across our lives. He explores the ways other cultures and happy people have historically connected as well as offers strategies for creating more connection in your life. I will say, once the ideas are introduced, it becomes pretty repetitive and feels like he was meeting book minimum requirements, so I suggest skimming the later parts of the book or speeding it up on Audible if you’re the type that has to finish any book you start.

Four Thousand Weeks: Time Management for Mortals
Oliver Burkeman

Burkeman’s book has similarities with the two other books on this list (Together and 168 Hours), but it’s still worth a read. Life is short, he reminds us, and we need to make the most of it. To do so, we must remember that we have more control over our lives than we think and that we can still make choices different from the ones we’ve made in the past.

The Genius Zone: The Breakthrough Process to End Negative Thinking and Live in True Creativity
Gay Hendricks

This book will help you identify your gifts, strengths, and talents. Everyone has a genius zone, where they can find creativity, fulfillment and satisfaction. Hendricks teaches us how to do more in our genius zones so that we can drive impact and happiness in our lives.

About Our CEO

Tracey Zimmerman is the President and CEO of Robots & Pencils, a digital innovation firm that helps clients transform their businesses with mobile, web and frontier technologies. With over 20 years of experience in marketing, technology, and process innovation, Tracey has driven significant growth at Robots & Pencils, including through championing strategic partnerships with Slack and Salesforce and building the company’s reputation in education, financial services, and retail and consumer goods.