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Leverage other people’s skills instead of hoarding your own, keep skills and data portable across Salesforce and HubSpot lock-in, and use AI as a sandbox—not a surveillance stack.
Clay before marble: redesign processes before you automate with AI, use real security layers like Brex, and don’t throw slop grenades.
Integrate your data systems for comprehensive insights and easier analysis, avoiding silos that hinder decision-making. Discover how to blend data for efficiency and profitability.
Tackle system inconsistencies to enhance efficiency and reduce hidden costs. Don’t tolerate inefficiency; explore sustainable alternatives to maintain reliability and productivity.
Introducing Efficiency Pro Max: a breakthrough tool designed to eliminate inefficiencies in your organization, crafted from recycled materials. Pre-orders open now, limited supply.
Reflect on March 2025’s data trends, client insights, and reader feedback in our latest blog recap. Discover how data is transforming business decisions and stay updated with future evaluations.
Learn 5 effective techniques to identify and eliminate unnecessary complexity in business processes and systems, enhancing efficiency and reducing hidden costs.
Learn why eliminating unnecessary complexity is crucial for your organization and how it can impact onboarding, productivity, agility, and employee retention.
Learn how managing natural complexity in business inevitably creates manufactured complexity and discover strategies to minimize unnecessary complications in your organization.
Identify and reduce unnecessary complexity within your organization to improve efficiency and streamline processes. Learn the difference between natural and manufactured complexity and take action today.
Discover how a proof of concept (POC) can validate potential solutions, engage stakeholders, and build project momentum. Learn practical steps to implement POCs effectively.
Incorporate a through line in your digital transformation sessions to maintain focus, drive curiosity, and align with overarching objectives for more effective discovery and design.
Overcome project stalls by acting rather than over-planning. Experiment with prototypes to break through design paralysis and maintain momentum in your initiatives.
Discover how Microsoft Teams and Slack reflect your organization’s culture and learn how to optimize their use to boost productivity and reduce friction.
February 2025 Recap: Insights and trends in client initiatives, executive conversations, and reader responses to shape your organization’s goals and resource allocation.
Enhance your team’s decision-making by integrating generative AI into your business processes, freeing up valuable human resources for more critical tasks.
Optimize your business processes by making your systems work for you, not the other way around. Discover how to leverage technology to free your people from repetitive tasks.
Learn the difference between pointless and useful friction in business processes and why some friction is essential for improving organizational outcomes.
Discover the key questions to determine if your organization truly understands its operational reality and how to optimize productivity, marketing, sales, and strategy alignment.
Learn how to navigate dissonance in digital transformation by distinguishing problems, root causes, and optimal solutions for better stakeholder alignment and project success.
Learn how to effectively allocate work by understanding capacity and estimates, ensuring efficient project delivery and preventing overcommitment.
Estimate project work using half-day or third-day blocks to align with natural work rhythms, reduce deviations, and allocate tasks based on capacity and capabilities.
Learn to estimate time effectively by understanding capacity through blocks instead of hours. This approach simplifies planning and increases accuracy in your project timelines.
When upgrading isn’t the best move, sometimes maintaining your current systems can be the optimal decision for your business.
Learn why starting with raw measures before defining metrics can help organizations frame problems better and avoid chasing the wrong goals. Discover a practical example in this insightful post.
Engage outside experts early in digital transformation to streamline business processes, leverage cross-industry insights, and reduce costs before system selection and implementation.
Learn how defining reusable actions in business processes can streamline design, reduce maintenance time, and improve documentation clarity.
Use lifecycle hooks to organize and simplify business process design, enhancing readability and identifying missing elements. Discover how to apply this method for effective documentation.
January 2025 recap: Trends in data and automation, AI agent discussions, nonprofit sector insights, and reader responses to recent newsletters.
Explore an alternative to traditional CRM by centralizing data, using purpose-built apps, and leveraging natural data emissions to improve workflow efficiency and reduce costs.
Evaluating whether your organization truly needs a CRM system by examining scenarios where CRM might be overkill and exploring alternatives.
Leverage AI and composite personality assessments to improve change management, align team dynamics, and ensure productive collaboration, using Enneagram and Ayurvedic Doshas insights.
Discover how combining Enneagram and Ayurvedic Doshas can enhance change management by understanding motivations, communication styles, energy, and stress responses for better team support.
Discover how understanding Ayurvedic Doshas can help identify energy and stress triggers, aiding smoother transitions during organizational change. Learn how to balance energy and mitigate stress effectively.
Discover how the Enneagram framework identifies motivations, communication styles, and conflict triggers to enhance change management strategies effectively.
Learn how personality assessments can enhance change management and foster empathy in your organization in our insightful five-part series.
Learn how to establish lean governance by creating a small, cross-functional team that passively oversees processes and systems without adding bureaucracy.
Centralizing documentation ensures efficiency and clarity by providing a single source of truth for processes, systems, and ownership, facilitating smoother operations and growth.
Assign clear ownership to each process and system in your organization to ensure accountability, streamline improvements, and enhance collaboration. Discover why this strategy is crucial for digital transformation.
Consider quick fixes only when there’s time pressure, isolated impact, and capacity for future optimization to avoid long-term issues. Read the full post for more insights.
Don’t reinvent already effective solutions. Learn how a resort smartly uses WhatsApp for communication, avoiding common pitfalls in app development. Embrace existing tools for better efficiency.
Learn how to leverage strong tailwinds like AI while maintaining discipline to ensure sustainable growth even when conditions change.
Navigating digital transformation requires caution; attractive strategies, processes, and systems may hide pitfalls similar to the deceptive beauty of the Portuguese man of war jellyfish. Proceed wisely.
Discover how sand castles can teach essential lessons for digital transformation: enjoy the process, use familiar tools, and embrace the impermanence of your solutions.
Maximize efficiency by implementing robotic process automation (RPA) now, instead of waiting for agentic AI. Learn how RPA can save time and reduce errors in your organization.
Understanding agentic AI: its potential to automate tasks with human-like intuition, the current marketplace, and why it’s not yet ready for your organization.
Discover how I can support your digital transformation in 2025 through newsletters, quick takes, strategy sessions, advisory services, and intensives tailored to your needs.
AI evolves as a thought partner, CRM bifurcates, and efficiency through sound strategy and well-designed business process still drives growth in 2025.
Avoid costly digital transformation pitfalls by validating needs, estimating value, and finding simple solutions. Learn how to prevent building unnecessary and complex systems for low-value problems.
Enhance your async collaboration with short, focused screen recordings. Learn how to create impactful clips and avoid sharing sensitive information.
Learn how to effectively manage technical debt by treating it like financial debt: use it strategically, then pay it down, restructure it, or eliminate it entirely.
We’ve all been tempted to ask for or make a quick fix, but it comes with a hidden cost. Let’s talk about how to mitigate the impact of these requests.
Whether you’re leading or working on a digital transformation initiative, your success depends on work getting done by others. Tracking these commitments is critical, but it doesn’t need to be complex.
It’s that time of year when chestnuts are roasting on an open fire and health insurance plans are available for open enrollment. Let’s take a look at how using AI can make this easier to decipher.
One of the common snags that delays or derails a digital transformation project is focusing too heavily on the looks of something instead of its utility. Let’s reinforce how to avoid this trap by focusing on value.
Shopping for a new system carries a similar set of tradeoffs as buying a new “off road” SUV. It’s all about how much you’re willing to spend to get one, then how you’ll maintain and extend it.
As we’re winding down 2024 and looking to 2025, I’m curious to hear what excites and worries you about next year.
Now that we know what digital transformation really is and examples of when it goes sideways , let’s take a look at a few examples of how organizations win with their digital transformation programs.
It turns out there’s an easy way to distill what digital transformation is and how it applies to your organization, even though the big consulting firms make it sound like a dark art.
We often dive into digital transformation projects because they tie into a strategic initiative or appear on a stakeholder’s wishlist, although the value of a single project is often murky. Let’s explore why that happens and walkthrough an example to see why it matters.
If your organization is facing capacity constraints and hiring full-time employees is off the table, automating or outsourcing are two other ways to free up capacity. Let’s explore which path makes sense based on the types of business process involved.
While the status quo is comfortable, organizations often miss opportunities for meaningful change as their strategies evolve alongside market patterns and platforms.
Let’s explore how applying the concept of composability from software engineering can improve how your digital strategy is executed by looking at three use cases.
Recursive questioning is an easy technique to apply when defining business challenges and designing solutions, although too often it is not used. Let’s take a look at three frameworks and why those are effective.
Regardless of whether you’re using the MSCW prioritization framework or something else, most stakeholders love to overload the higher priority categories. Let’s take a look at why that happens and how to counter it.
While entertaining two guests over the weekend, a discussion about their feelings of being overloaded with personal and professional challenges led to an interesting insight into how AI can be applied to unlock different perspectives.
When it comes to your current and future states of your business processes and systems, a critical component is the people involved. However, sometimes we overlook this and identify gaps later than would be ideal. Let’s see how Swiss cheese can help us.
Organizations that are just starting their digital transformation programs often face challenges around documentation and understanding why a business process or system is not working as expected. Let’s explore how test scripts solve both of these challenges.
Imagine you’re in the back of an Uber on the way to a meeting and need to get up-to-speed on how your organization has engaged with this account thus far. You’re staring at your iPad: what is on the first page in your BI dashboard?
Most organizations fixate on the licensing costs of their cloud platforms and SaaS applications, although when purchasing decisions are made, the cheapest does not always translate to being the most cost-effective.
While AI can generate meeting summaries, you should think twice about whether it makes sense to go down this path at your organization. Let’s explore why and how to do it if you’re adamant.
Practically everyone has been in a meeting that should have been an email, Slack message, or quick screen recording. However, so many organizations continue to perpetuate the cycle, even though async collaboration increases productivity.
Even though you might be excited to drive digital transformation within your organization, you’ll likely encounter folks that do not share the same level of excitement. Let’s discuss why people resist changes and how to help them adapt.
Yesterday, we explored how to identify and prioritize use cases for AI , which is fundamentally based on a bottom-up approach for auditing and documenting use cases by observing process execution and system usage. The same method applies if your goal is to recognize efficiencies through automation.
Figuring out where to integrate AI into your organization is a challenging exercise, as the viability of each use case requires granular understanding about the business process, people, and systems involved. However, it’s also essential to consider where AI can assist in streamlining and enhancing
A powerful use of AI is identifying accidental white space in how your organization positions itself and executes its business processes. Let’s explore how to find and fill these gaps using data and AI.
When digital transformation projects come to an end, we consider those changes to business processes or systems as being done (for now). However, this does not mean that we’re also stable. Let’s use a metaphor to see how done and stable are not the same, then we’ll take a look at three points to hel
Whenever we’re planning changes to how a business process or system functions, a bunch of information is captured upfront as part of meeting notes, research, and documented requirements. One of the challenges is how to organize these during the discovery phase, so let’s see how three passes helps ma
To help your organization estimate the total cost of ownership for a new technology platform, let’s look at how to structure your estimates, why these costs are essential, and where deeper due diligence can prevent underestimating or missing key items.
Embarking on swapping or adding technology platforms involves a mix of one-time and ongoing expenses, although organizations often are bound when their estimated costs are too low, thus running into budget constraints.
Plenty of folks have talked about how to use generative AI to write or edit emails, even crafting an entire marketing journey with a single prompt. Let’s take a look at a small but mighty use case, plus two prompts to use as a starting point.
When working on large initiatives or managing multiple clients as a consultant, you likely get messages late in the day that deserve more than a quick response. Use these easy techniques to let the sender know you’re aware of it.
Sharing async screen recordings is a great way to collaborate, especially if you’re collaborating with teams in distant timezones or your calendar is overcommitted. However, there’s a lurking issue that is easy to mitigate, yet so many people encounter it.
An area where you have complete control is how to maintain and grow your own productivity. Finding what works well can unlock your ability to make a larger impact in your organization, and potentially open doors to new opportunities elsewhere.
Delivering digital strategy and transformation initiatives can slip into a trap of having an endless project, whereby the scope continues to change and the timeline extends indefinitely. Let’s explore why this happens, how to recognize it, and mitigate it from happening.
A quintessential debate that has existed since the dawn of CRM platforms is whether you should use Leads or Accounts & Contacts as a place to organize your prospecting activities. Let’s take a look at considerations for how to decide which approach to use.
One of the trickiest things about this domain is how fundamentally different it feels, so I looked into Connor’s course to see how he frames it for business / non-technical stakeholders.
We talk about the hub and spoke model when designing systems architecture, although this wide perspective often loses sight of each stakeholder group. Beyond the entire systems landscape, each stakeholder group needs a hub, too.
If you’re curious about how to get started with generative AI, a benign place to get started is by creating a helpful AI assistant for your employees. Let’s explore why this use case and how to do it.
Now that we’ve discussed why you should ask for more details and educate a person after submitting a web form, plus a few options of how to do it , let’s talk about chaining this together in a full-featured solution.
Let’s talk about a few ways you can continue to engage a person after they submit a form on your website, as we covered why you should in a previous newsletter.
Practically all organizations are data hoarders and retain data longer than needed in their production systems. While there’s no reality TV show about this topic, it deserves a fresh look on why you want to archive your data.
Bloomerang and Qgiv released a second iteration of their research into how generational differences influence giving and engagement for nonprofits. Let’s explore takeaways across all generations and on a per generation basis.
Digital transformation sounds like a nonsense phrase, especially when so much of our world is already digital. At its core, the concept boils down to handful of activities. Mastering those make you a powerful force at driving digital transformation within your organization.
Organizations extend portals to their external stakeholders to make it easier to transact, get support, or collaborate in a place that simply works better than email. A lot of organizations forget to include marketing outside of logos and branding. Let’s see how this presents a huge opportunity.
Choosing to no longer invest in a project or program because it will not achieve desired outcomes is a valid strategy, and frankly, is underutilized within organizations. The challenge is using criteria and feeling comfortable with moving on.
Merging an acquired organization’s data and processes can be straightforward if you have strong change management practices and a solid understanding of both organizations’ systems. Here’s how to reduce risk of encountering challenges along the way.
Intentionally creating ambiguity about which generative AI vendors and models are being used helps mitigate risk, but it is an even larger opportunity as your organization learns and matures its usage of AI.
A lot of organizations organically adopted Slack or Teams, either as early adopters or from the outside force of the Covid-19 pandemic shifting how we work. Let’s look at three areas where most organizations stand to benefit from as it relates to how they’re using Slack or Teams.
You’ve probably heard someone respond with “putting out fires” or talk about how part of their job involves “firefighting”. Let’s unpack this metaphor a bit and see how it takes an uncomfortable twist.
Recommending products or services used to be a task that was best done using predictive AI, however, there is another way to approach this problem using generative AI.
Referring people to your website and being able to capture part of that data in web form submissions is helpful to create traceability for your marketing efforts, plus it can pre-fill parts of the form to save people time. Let’s take a look at ways to do this.
When developing technology solutions for your business, there’s often a tradeoff of “build vs. buy” as part of the evaluation process. However, in reality, most organizations end up with a “build and buy” mindset. Let’s take a look why that is with Uber as an example.
Deciding to engage one or multiple vendors to support a transformation program depends a lot on your organization and the scope. Let’s take a look at each option and its advantages and challenges, then look at a few questions to ask to help the decision making process.
One of the beautiful aspects of visual diagrams, especially those that offer the ability to link to other pieces of documentation, is that it lets you “time travel” to understand how and why processes and systems have evolved over time.
Understanding your organization’s culture as a whole and down to each person is not often talked about, yet it has a major impact as organizations undergo growth, restructuring, and embark on expensive and lengthy transformation programs.
Documents are part of every organization’s processes. Some rely on paper-driven workflows that result in typewritten or handwritten documents, and others need to process lengthy documents as part of their everyday work. AI can help streamline these workflows and make it easier to use the data in oth
Revenue models drive how your organization generates income, plus enables growth in a sustainable and efficient manner. Let’s explore each of these models, its benefits, and how it fits into digital strategy.
There are three trends in team and organizational dynamics that are limiting how organizations can achieve their fullest potential. Let’s review each trend and how to address it.
When someone has awareness of your brand, shows interest in what you do, and expresses desire to be known via a web form, it’s a great opportunity to ask more questions immediately afterwards to develop an even richer understanding of who they are and their motivations.
Whether you’re running a sales team or a group of fundraisers, your prospecting activities deserve to be split into different roles based on how you intend to engage.
RACI is a way to define how stakeholders align to specific roles for a project or program, which helps reduce ambiguity related to a person’s involvement.
One of the skills that is not taught in most industries is how to write meeting notes, which is a shame given the amount of time we collectively spend in meetings. Let’s take a look at how to write better meeting notes by adopting a structure and syntax.
Transformation initiatives and technology platform licensing often carry large explicit costs that seem expensive without proper context. Adjusting these into tangible terms breaks down hesitation and objections to the nominal cost.
Over the past few years, appointment scheduling with people outside your organization has become significantly easier to do as collaboration platforms created functionality that was previously requiring a paid add-on.
Defining constraints and communicating those transparently to all stakeholders involved is the easiest path to exceeding their expectations (or at the very least, meeting them). Projects that don’t take the time to do those end up leaving folks desiring more or bloated scopes that overrun timelines
I often joke that modern business apps are just “spreadsheets in the cloud”. While this is mostly true, it is a point of leverage that you can use to your advantage as your processes and organization evolve.
Technology implementation firms often include change management in their statements of work with nebulous, hand-wavy language, which is also the reason why it’s the first thing on the chopping block when a change order increases scope for functionality.
Technology platform licensing contracts vary in structure and some vendors with enterprise-grade products have virtually impossible to negotiate cancellation terms. Before you sign a contract, you should get a second opinion about the products and unit prices.
Transformation initiatives are often major shifts in how people work, and the tricky part is finding the right balance when designing a business process or system to avoid over-engineering, as this is equally as bad as under-engineering.
Using an informal and playful approach to defining level of effort, impact, or priority is helpful when operating on teams that deliver incremental changes on a regular basis.
A common mistake that occurs in digital transformation initiatives is conflating the roles of the consultant and systems implementer (SI). Some ecosystems curated by platform vendors actively create this confusion for their customers by applying the label “consultant” to what is actually an SI.
Microsoft and Salesforce both have used marketing to label AI as a copilot, although this is not the appropriate metaphor from aviation. As a pilot with over 600 hours in the cockpit, AI is an autopilot, not a copilot.
Yesterday, I led all-day workshop for a consulting firm based in New York City with a focus on establishing a foundation around the core domains of AI followed by a hands-on training to apply generative AI to use cases for their client base.
Finding the nearest and most suitable exit isn’t just for flying on planes and going to the cinema. Knowing how to exit systems is equally as important.
Generative AI has been and will continue to be a hot topic, yet it’s only one domain of artificial intelligence that your organization can be leveraging to improve business processes. If you’re dipping your toe into the waters of AI, you can approach it serially or in parallel.
There are many frameworks for prioritizing, although MSCW stands out as being easily understood by functional and technical stakeholders with its unambiguous definitions.
Data analytics platforms and “data clouds” have become more accessible as technology platforms mature and costs to acquire and maintain are historically lower than ever. Yet, organizations still take a cautious approach to implementing a data warehouse and/or standalone analytics platform.
Let’s take a look at how the 5Ws framework gets applied to an example business case . If you haven’t taken a look at that example business case, pop over there first before continuing to read.
Now that we’ve gone through all of the Ws in the 5Ws framework , let’s apply it to a sample business case for an organization embarking on a digital transformation and modernization program.
Let’s take a look at how to use the “why” of the 5Ws framework to define problems and gather requirements for a digital transformation initiative.
Let’s take a look at how to use the “when” of the 5Ws framework to define problems and gather requirements for a digital transformation initiative.
Let’s take a look at how to use the “where” of the 5Ws framework to define problems and gather requirements for a digital transformation initiative.
Let’s take a look at how to use the “what” of the 5Ws framework to define problems and gather requirements for a digital transformation initiative.
Let’s take a look at how to use the “who” of the 5Ws framework to define problems and gather requirements for a digital transformation initiative.
The same 5Ws that we learned in primary school is a helpful framework to use in digital transformation initiatives. When architecting business processes and systems, it is useful to learn about an environment and can make others question assumptions that have been made.
Authentication and authorization are two concepts that are often misinterpreted when designing and integrating systems. Fortunately, there are a couple of relatable metaphors to use in discussions.
Leveraging outdated systems and manual processes in the age of automation and AI increases costs to find and retain talent, plus reduces the productivity and competitive advantage relative to peers.
Before you take a bite or melt it for fondue, the iconic Emmental cheese can be sliced up and used to identify and mitigate gaps in your digital transformation initiatives.
Incorporating frameworks like SCQA is helpful to facilitate discussions and deliver presentations. It establishes context, gains alignment from participants, and identifies potential solutions.
A/B testing in email campaigns is inconsistently adopted across multiple segments of the market, despite most email marketing platforms offering this functionality. It’s time to start using this more often and aggressively, especially when you have more to gain from the insights it produces.
There are a handful of concepts related to address data and systems that are helpful even if your organization doesn’t send letters or packages to customers.
Operating without backups of your systems is like driving a car without wearing a seatbelt.
Troubleshooting process exceptions and system bugs have a compounding effect when there are many places to look. Three steps get you in a better position to deal with uncertainty.
Using independent software vendors (ISVs) to satisfy parts of your digital transformation project can accelerate when timelines and enables you to realize value faster, yet it comes with tradeoffs.
Demos and presentations are common, and whether it’s happening live in person or virtually, or recording for folks to watch later, here are a few ways to make it land better.
Action items have a higher chance of getting done the first time if it’s clear what to do and it has a single owner.
Systems and dogs have a lot in common. I love using metaphors to unpack big or unfamiliar concepts. Let’s see how this one holds up.
Every weekend, I carve out time for a weekly review and one of the first steps is to get to inbox zero. I use this for both emails, messaging, and tasks, but let’s dive into how this works for communication.
Office politics has a strong influence on how changes are rolled out within an organization and has the power to build cohesion or entirely derail an initiative.
A few people ask me each month “what are you using to write your meeting notes”, and recently they might ask a follow up like “are you using AI”.
It’s inevitable in digital transformation projects that you will encounter vendors that follow somewhat rigid sales processes and use account executives.
Attention to detail pops up all over the place on digital transformation projects. Being able to have a keen eye to spot things that are out of place is a helpful tool.
Teams within your organization may start using AI to solve specific challenges, but letting each group attempt to self-organize increases the likelihood of missed opportunities and potential inefficiencies.
Underestimating the time and effort required to deliver changes regularly appears as organizations embark on digital strategy and transformation projects. At its core, this is a cognitive bias called the planning fallacy, which also touches on underestimating risk and overestimating benefits.
Despite having a a simple framework for digital transformation (spoiler: it’s just a three word hierarchy ), countless organizations see their digital transformation programs go sideways. Let’s explore a few examples to see why that happened, and what you can do to avoid falling into the same trap.
Surveys are a powerful tool to gauge customer sentiment, but most organizations fall short by failing to create mutual value when asking for feedback. Let’s unpack why that is and how to avoid it with an example.
Launching a portal for external stakeholders can streamline interactions, reduce the workload on your team, and boost overall efficiency. However, there’s a common pitfall that organizations make by trying to perfect everything from the start.
Predictive AI relies on training algorithms with data, and often the data that is used by the algorithm is actually derived from your raw data into a set of “features”. Let’s explore why you want collect and enrich your data to make this process more impactful.
Framing a problem is almost always harder than designing the solution. This is typically because there is not sufficient understanding of all of the dimensions and the impact that it has on people, business processes, and systems.
After attending Salesforce’s Agentforce World Tour NYC 2024 event today, it’s clear that Salesforce wants you to use as much of their products as possible. But, does that actually make sense?
The concepts shared are from Tiago Forte’s Building a Second Brain and The PARA Method , two books that I read over summer holiday (yes, nonfiction is my flavor of “beach read” books).
A common mental trap that you can fall into with digital transformation projects is assuming that less vendors results in less complexity. However, this is highly dependent on knowing how mature and complete the set of features are that you’re using.
Best practices is treated like a buzzword phrase within digital strategy and transformation projects, although the issue with this starts with the superlative nature of the phrase.