Quit Kicking Cans

Let’s Talk About Debt, Baby (insert bad 90s cover music)

If you’ve never done it before, run a search for definitions for the word ‘debt’. Depending on where you look, you’ll get a wide range of answers. From the practical: ‘an I.O.U. for money, goods, and/or services’ to the more idealistic (and slightly ominous sounding): ‘trespass or sin requiring reparation or expiation’. Debt is one of those terms that can cover a lot depending on the context. 

For the sake of this discussion, let’s keep it simple and say that debt is an obligation or liability that is owed to someone else. In general, debt involves an agreement to get something now with understanding that repayment will occur at some point in the future (usually with interest). For a lot of people, the most common way to relate is from a financial perspective: one party borrows money or assets from another party with the agreement to pay later. This could be in the form of loans, bonds (well played Mr./Ms. Monopoly), or credit. Because very few things are ever free, let’s keep that part about interest in mind!

Debt can be both a good and bad thing depending on the context and how it is used. In some cases, debt can be beneficial. We can all think of financial examples of ‘good debt’, like taking on debt to invest in a new business or some form of education. This kind of debt is generally considered ‘good’ because it can greatly improve your future financial growth and potential prosperity. The same for debt you take on to buy assets that appreciate in value, like a home.

On the other hand, debt can also be harmful if it’s not used responsibly. Taking on high levels of credit card debt can lead to financial strain and difficulty making payments. Similarly, taking on too much debt in a business (which we just heard could be considered good) can lead to financial difficulty and even bankruptcy if it’s not managed properly. Good or bad, the concept of debt is an important part of life and is used by individuals, businesses, and governments everywhere. 

You might be saying to yourself: “Self, I’m not a finance person. In fact, I am a technical person! Why did I just spend time reading the last 300+ words about debt?”

My response is simple: It’s because the concept of debt is not limited to money and finance!  

In fact, debt is all over in the technical/business worlds and the same underlying principles apply: its virtually unavoidable and needs to be managed (just like financial debt).

To prove my point, let’s look at two common types of debt: Technical and Organizational.

Technically Speaking… Debt can be Technical!

(WARNING: All puns intended) The term ‘technical debt’ is widely attributed to a software developer and computer programmer named Ward Cunningham. He used the metaphor of financial debt as a way to explain the trade-offs between short-term gains and long-term costs of owning complex systems. To paraphrase his explanation, technical debt is the cost of additional rework caused by choosing an easy, corner-cutting solution now instead of using a better, well-thought-out approach that takes longer. 

Basically, it is the cost of doing things the ‘easy’ way instead of the ‘optimal’ way. It is the sum of all the trade-offs, shortcuts, and sloppy practices that went into the product as it was being built. It’s the reason every product has technical debt even if we don’t necessarily see it. No matter what product we make, we all build this type of debt in as we make it.

Examples of technical debt include:

• Inefficient software/code that requires a higher upgrade or patch frequency.

• Lack of standards/practices that lead to poor performance and/or drive rework.

• Poor planning on integration that causes increased complexity and longer timelines.

• Cost cutting on hardware component that cause product to be slower/less compatible and physically limits your products functionality.

Just like with financial debt, there is interest on technical debt. At some point, you’ll have to pay for those corners that were cut! Anyone who has ever had to go back and add unplanned/unsupported features or integrate two completely independent products can tell you how fun that process can be! The costs can sometimes be more than the original cost of the product, depending on the level of complexity and how much technical debt had accrued.

Because we rarely make perfect ‘optimal’ products technical debt can’t be eliminated. We have to make trade-offs as we go. We just hope the ones we make are the right ones. Due to the cost, resource, and other potential impacts, it is essential that we be aware of and monitor technical debt so that it doesn’t accumulate to the point where it derails your product (or worse!). 

Organizational Debt (a.k.a. Proof You Were Right About How Dysfunctional Things Are!)

The organizational equivalent of technical debt is known as (<queue drum roll> wait for it…) organizational debt. Organizational debt is the cost of running, maintaining, and updating an organization that has been built in a way that is less than ideal. We call it ‘organizational’ because it can be an entire company, a project team, a business unit, or any combination. Basically, any group tasked with making a thing can be affected. Similar to technical debt, organizational debt can hide lurking in processes, structures, and systems and causing havoc in ways that are hard to understand, hard to change, or difficult to improve. 

Because running any organization is filled with trade-offs (just like technical development), it’s nearly impossible to eliminate organizational debt. That means we are left with monitoring and management as the way we control the effects it has on development and maintenance. Because its a type of debt, it accumulates over time and if not addressed, can become a significant obstacle to achieving organizational goals. Identifying causes and developing ways to reduce them can help organizations to improve their performance, adapt to changing market conditions, and create a more agile and resilient organization.

Examples of organizational debt include:

• Bureaucratic processes that slow down decision-making and hinder innovation.

• Silos and lack of communication that hinder collaboration and information sharing.

• Inefficient and outdated systems that cause delays and errors.

• Lack of clear roles and responsibilities that leads to confusion and inefficiencies.

Organizational debt also has interest. Not dealing with a poor performing employee can cause the entire team to function at a reduced level or even break down entirely. Repeatedly choosing suppliers or vendors based largely on non-technical factors (read this as ‘cheaping out’!) can cause your organization to develop products using inferior parts, leading to unhappy customers, increased support/repair footprints, etc. Hiring unqualified or inexperienced personnel to save money can lead to poorly written code with more bugs that will take time and money to fix. This will in turn cause your customers to throw things, say bad words, and potentially find a new solution to their problems.

Organizational debt also needs to be monitored, but it can be much harder to do for this type of debt. This is because it accumulates in, across, and between every functional area. It assumes different forms in each case. Basically, this type of debt is the chameleon-like monstrosity lurking within organizations of every size. People at every level need to be looking for this type of debt, developing strategies to monitor it, and be empowered to mitigate it. The goal of every organization should be to keep debt in check before it grows and destroys your business (before stomping off to eat the capital city of an Asian island nation). 

Conclusion (a.k.a. The Payoff)

Both technical and organizational debt can have significant impacts on a business. Any time someone says to deal with a problem later (and kicks some poor, unsuspecting can down the road) they just added to your debt! Technical debt can create issues with product quality and customer satisfaction, while organizational debt can create issues with employee retention and business growth.

If you are part of the technical team responsible for making a product, technical debt can have you pulling your hair out. If you’re constantly fighting fires instead of building products, it may be time to call a time out and rally your troops to look at why. There’s a good chance the root cause is technical debt coming due. (With interest!)

If you are a manager, business owner, or other stakeholder who is sick of fighting folks who are supposed to be on the same team, you should probably start taking a hard look at why. Sit down and start asking hard questions. Bring in fresh perspectives and consider making changes to how business is done. Pay down the organizational debt before it’s too late. Change isn’t easy, but it is a necessary part of life. (No matter what business you’re in!)

So, how can businesses avoid technical and organizational debt?

To avoid technical debt, businesses should:

• Build your technical culture around accountability, quality, and maintainability.

• Prioritize minimizing technical debt in project planning and budgeting.

• For software: best practices! Also, regularly review and refactor code.

• For hardware: best practices! Also, don’t cheap out and test, test, test.

• Take process improvement seriously and look at everything as a process.

• Use automated tools to detect and manage technical debt.

To avoid organizational debt, businesses should:

• Prioritize communication and tear down silos! Put away the Blame-throwers!

• Empower group leadership to handle issues and actually resolve problems. Stop kicking those cans!

• Implement continuous improvement and effective learning.

• Regularly review and update processes and systems.

• Establish clear roles and responsibilities.

• Use data and analytics to identify and address inefficiencies.

At the end of the day, debt can be good or bad. It depends on you and how you handle it (or don’t handle it). But for Pete’s sake, leave those poor cans alone… They’ve suffered enough!

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You Really Should Question Everything…

The Case for Why You Should Question Everything (to a Point)

What comes to mind when I say something like: ‘Question Everything’? A few different images could have popped into your head. Maybe you saw an inquisitive 6-year-old; the kind who relentlessly asks ‘why?’ after every answer and is never satisfied. Or perhaps you saw some angst-filled person obsessed with finding deep, cosmic understanding; the ‘how do I know I’m even really me?’ type who wrestles with unanswerable questions. I’m going to shoot for something in between those two extremes. I want to lay out the case for why you should ask a lot of questions and I plan to do it against the backdrop of the universally applicable (yet eminently hair-raising) problem: ‘What’s for dinner?’

Before we jump into that minefield, it’s worth clarifying a few points:

• When I say: ‘ask a lot of questions’, I don’t mean endlessly asking ‘why?’ to everything. That is unhelpful (and could result in bodily injury if you’re annoying enough). I mean asking the right kind of questions, based on your current point in the process and the task(s) in front of you. This will hopefully become clear as we walk through our example. Just remember – the questions you ask must be targeted!

• The goal of asking questions the way I’m talking about here is NOT to have all the answers before making a decision or taking an action. It’s not driven by self-doubt or paranoia that you’ve missed something. The goal here is to double-check that the plan is as correct as it can be based on the available information at the time. It’s about ensuring you’ve taken the time to consider possible results of whatever action you’re about to take, not that you have endless contingency plans in place. This is another point that will hopefully be made clear through our example. Keep in mind – the questions you ask must have an answer and a scope!

So, What’s for Dinner?

Let’s say that you are hanging out with your favorite group of people. At some point, the dreaded question comes up: ‘What’s for dinner?’ After your internal panic dies down, think about what you normally do in that situation. To make it a little easier, we’ll assume that everyone has agreed to order take-out. So, what happens next? For most of us, some version of the following occurs:

• Information gathering happens - Phones come out and people look for what options are close by. They’ve already started asking targeted questions, like: ‘what restaurants are near us?’ and ‘which ones offer take-out?’

• Down-selection happens – Conversations pop up and people start narrowing down the list of potential food choices. They’ve asked even more targeted questions, such as: ‘what does everyone feel like having?’

• Decisions are made – Once all the targeted questions of where to order are answered, then each person must decide what to eat. They start asking more targeted questions, but with a different focus: ‘what do I want to eat from Kung Pao Palace*?”

*Author’s Note: I made up a plausible sounding restaurant for the purposes of this example. I have no idea if Kung Pao Palace is a real place and therefore cannot endorse or promote such a restaurant if it does exist.

To make it easier to see what we’re talking about, let’s break down what’s happening using a tiered approach. The highest tier will have the broadest focus, while the lowest tier will have the narrowest focus. Right now, we’re talking about the perspective of the group as a whole and we can say:

1. The team identified a problem - they’re hungry.

2. They came together to reach a solution - they need to get food in order to not be hungry.

3. Each team member identified their piece that needed to be incorporated into that overall solution - their part of the order. 

4. The solution was implemented - someone called the order into the Kung Pao Palace.

The team was focused on a strategic problem and asked questions targeted to a decision at the that level. In our personal lives, we do things like this all the time without even thinking about it consciously. In a work setting, people sometimes struggle with reaching a workable solution. We’ll get into reasons why that happens after we’ve finished our example, but first let’s keep it moving! Everyone is hungry!

The order is in. The make-believe staff of the Kung Pao Palace is diligently preparing the team’s order and you’re tasked with retrieving it. What happens now? The next level of our tier approach will look at the collection of tasks each individual needs to accomplish to deliver (pun intended) their piece of the solution. To keep things simple, we’ll assume the other members of the group are doing their own thing and just focus on things assigned to you.

In general, it goes something like this:

• Information gathering happens – Your phone comes out again and you pull up your favorite direction-providing app. Even if you know how to get to the restaurant, you may still use the app to let you know if traffic is bad or which route is faster. You’ve already asked targeted questions, like: ‘how’s traffic right now?’ or ‘which way should I go?’

• Down-selection happens – The super-smart app developer folks have used their big brains to crunch all the numbers and provide you with several options of route based on their list of targeted questions. You simply need to tap the route you want and ‘Presto!’ 

• Decisions are made – You tap on the ‘Go’ button and begin your journey to the land of promise and delicious dumplings: Kung Pao Palace.

We went from looking at what the entire team was doing to looking at what a specific member is working on. The list of things that need to get done has become more focused, because you have a specific part of the overall solution to consider. We are closer to the actual action being implemented, but not quite there yet: 

1. The team member was assigned a task – you must get the team’s food and make it snappy! (People are getting a little hangry).

2. The team member figured out how they wanted to do the task - you decided to focus on driving and let the app do the navigation.

3. The team member stared executing the task - you started driving.

The team member was focused on figuring out how to complete their specific pieces and again used questions targeted at the appropriate level to reach a decision. We’re two-for-two on things we do all the time. We naturally get to an answer without needing a lot of extra input or required thinking. It’s almost like we’ve practiced it or something, but we’ll go into more details about that later. You need to get moving! 

You dutifully set out to retrieve the take-out order from Kung Pao Palace. For this part, we’ll assume that you’re a good driver. Being a good driver, you follow all the required laws and regulations. You never speed, always signal your intentions for the other drivers, and would definitely not read an article about questioning everything while driving at any point. (Speaking of which, you should probably focus on the road. You are driving right now…) So, let’s look at what’s involved:

• Information gathering happens – You are watching your surroundings and taking input from your trusty direction-providing app. During the trip, you constantly ask yourself targeted questions, like: ‘is there enough space between me and others?’ or ‘when do I need to move over for my next turn?’

• Down-selection happens – When the time comes for you to move over, you signal your intentions, check that the area is clear, and look over your shoulder (because we said you’re a good driver, remember?). You ask yourself ‘is it safe to move over?’ and then double-check to make sure you have all the information you need to confirm. 

• Decisions are made – You move over and make the turn into the parking lot of the Kung Pao Palace!

We said the lowest tier of our approach has the narrowest focus, on the exact activity being worked/as it’s being worked. That sounds like driving. Which means our final breakdown looks something like this:

1. While executing the task according to plan, the team member was constantly asking themselves targeted questions that were directly focused on the work that needed to be done – you were driving safely and wanted to continue driving safely.

2. The team member verified that expectations matched reality (to the best of their ability) - They asked questions to ensure they were doing the right thing and double-checked the best they could - you didn’t blindly follow instructions from the app which would not have been driving safely. You merged that info with the things you do as a safe driver: signaling properly, checking your blind spots before moving over, etc.

3. The team member successfully executed the task - you made it to the Kung Pao Palace safely.

In this case, you used targeted questions while doing the work to help you get the job done. That’s three-for-three on things we do all the time. Since you did such as great job, we’ll finish up our example by saying you made it all the way back to the group with piping hot take-out! You are celebrated as the hero of the day and get the extra dumpling as a reward.

How to Question Everything in Four Easy Steps

You enjoy the imaginary spoils of your imaginary hard work. I’ll wrap up by explaining why you should even care about the topic of questioning things. A lot of times, people get the entire concept really wrong. They convince themselves that in some situations making decisions/taking actions is somehow different (or more difficult) than it is ordinarily. I would humbly say it’s not. There is absolutely no difference, and I can prove it.

You make consequential decisions all the time. Take driving for example. If you decide not to stop at that red light, there are some dire consequences. As a driver, you ask yourself (at some level) what the wise thing to do would be. Changing lanes without looking? Same situation, same stakes, same questions. We do it thousands of times in our daily lives and it barely even registers. 

What is the main difference between driving and some other risky scenario? I would say: practice! We do it so much, we don’t think about driving for the most part. From the perspective of an outsider, driving involves making important decisions on a timetable, with potentially life-changing consequences, and constantly changing circumstances. All while hurling ourselves along inside tons of metal at breakneck speed. From the perspective of an insider, we’re listening to an app tell us where to turn and daydreaming about dumplings. We manage to do that because we’ve practiced the task. A lot!

But what happens when we come across something new? It’s unfamiliar. We get nervous because we aren’t so sure of what to do anymore. We start feeling pressure. We haven’t practiced enough to know how to instinctively handle the situation. It happens all the time. Especially in the workplace. Management can’t decide which new course of action to take. Coworkers who can’t seem to figure out exactly how to do their portion of the new product. Sometimes we can’t make a tough decision for ourselves because we’re too close to the problem and don’t have proper perspective. We’ve already touched on a couple of examples of why it happens. Anyone can fall prey to things like:

• Trying to have all the answers before making a decision or taking an action.

• Having too much information and not being able to decide on how to use it.

• Self-doubt or paranoia that something has been missed.

Questioning Everything Effectively

So how can we avoid those traps? How can we be sure we’re on the right track and avoid trouble in the first place? How do we get in the driver’s seat, so to speak? By getting yourself into the practice of questioning everything in an effective way! Here are my recommendations on how to start:

1. Make it a habit to ask yourself questions like:

•  Is this the best way to do things?

•  How do I know?

•  What am I missing?

•  Am I looking at this the right way?

•  Who else can I ask for input?

•  Does their input change anything?

2. Understand the goal when you ask questions. This isn’t about self-doubt or covering every base. It’s about making sure you have what you need to make a decision about the task at hand. It’s the same as checking your blind spots while driving. You check them, incorporate that information, and adjust your plan accordingly. You don’t veer to the shoulder, screech to a halt, and wait for every other driver to move off the road.

3. Target the questions for what you’re trying to do. Knowing the number of pages in War and Peace will not help the group answer the question of ‘what’s for dinner?’ Asking people their likes/dislikes/allergies would be very helpful. Knowing the correct internal temperature to heat a dumpling to is useful if you’re cooking dumplings, but not so much if you’re just eating them. Figure out what level you’re at and scope your questions appropriately. 

4. If you’re still having trouble getting to a solution, you might be asking the wrong people. Maybe it’s time to find new people and new ideas!

Now go practice! Good Luck!

Thanks for reading! Please let me know what you think. I respond to all comments personally.

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Outsider Perspective (and Why You Should Care)

Part 1 - Making the Case for Why You Should Care

If you’re reading this, chances are you are looking for insight to help reduce friction in your organization. Before we get to the answers for all your burning questions (and since it has direct bearing on the ‘why you should care’ part), let’s start by clearly defining the problem. No matter what business you’re in, there are major problems common across most organizations.

Pitfalls that can affect organizations over time include:

• Resistance to Change - Decision makers become resistant to change and unwilling to adapt their practices to new circumstances. This prevents the organization from evolving and adapting to the everchanging business environment.

• Outdated Practices - Organizations that don’t keep up with the latest practices and techniques will fall behind and struggle to remain competitive.

• Poor Communication - Poor communication leads to misunderstandings and conflicts between the organization and its employees, negatively impacting morale and productivity.

• Lack of Transparency - If decision makers are not transparent, trust erodes, and conflicts break out within the organization.

• Ineffective Leadership - Negatively impacts morale and productivity within the organization, leading to high turnover rates and difficulty attracting top talent.

These aren’t just ‘big company’ problems. Given the right conditions, these issues can (and WILL) affect organizations of any size. It’s important for people in these organizations to be aware of/constantly vigilant for these potential pitfalls. They also need to actively take steps to avoid them in order to ensure that their management practices remain effective over time.

Here are some ways to avoid those pitfalls:

• Embrace Change - Encourage a culture of continuous learning and be open to new ideas and approaches.

• Stay Up to Date - Keep up with the latest practices, techniques, and ways to incorporate them into your organization.

• Foster Open Communication - Encourage open and honest communication and (most importantly) listen to feedback and concerns.

• Be Transparent - As much as possible, decision making and communicate clearly with your employees about the reasons behind your decisions.

• Develop Strong Leadership - Foster a culture of strong leadership by providing actual leadership training and active development opportunities for managers.

By taking these steps, you can help your organizations avoid the debilitating pitfalls that develop over time.  You ensure that your organizations remain effective and adaptive. So, there you have it! A simple, clearly defined plan to make every organization run more smoothly and efficiently. No muss, no fuss!

Still here? Is it because you’re already experiencing some (or all) of the problems I listed above?  Do you want to know what to do when those pitfalls are already problems impacting your organization’s ability to deliver? That’s an easy one: Call in the outsiders!

Don’t worry about sounding professional. Sound like you. There are over 1.5 billion websites out there, but your story is what’s going to separate this one from the rest. If you read the words back and don’t hear your own voice in your head, that’s a good sign you still have more work to do.

Be clear, be confident and don’t overthink it. The beauty of your story is that it’s going to continue to evolve and your site can evolve with it. Your goal should be to make it feel right for right now. Later will take care of itself. It always does.

Part 2 - What do ‘Outsiders’ Bring to the Table?

First, let’s establish exactly what we mean by an ‘outsider perspective’:

1. A view or perspective that comes from someone who is not part of a particular group, organization, or community. (This seems self-explanatory, given the whole ‘outsider’ part.)

2. The ‘outsider(s)’ providing this view possess the required skills and expertise to necessary to facilitate what you are trying to accomplish. (This part is not as obvious at the outset, but it makes sense when you think about it.)

The type of outsider perspective described above is extremely valuable in cases where an organization is experiencing pitfalls like the ones outlined in Part 1. Because they come from outside an organization, they aren’t influenced by the same biases, assumptions, or experiences as those who are normally part of the group. Outsiders who can understand technical challenges can also bring different tools or approaches to the table. Basically, the right outsiders come equipped with a very useful superpower: a fresh perspective on the situation that allows them to offer new ideas and insights than those inside the group might have considered.

Here are some added details on the benefits of outside perspectives:

• Fresh Ideas and New Viewpoints - By seeking out diverse perspectives, you can gain new insights and ideas that you may not have considered before.

• Improved Decision Making - Hearing multiple perspectives can help you make more informed and well-rounded decisions.

• Increased Creativity - Getting input from a variety of sources can stimulate your creativity and help you come up with more innovative solutions to problems.

• Enhanced Communication - When you can see things from another person's perspective, you communicate more effectively with them.

• Greater Empathy - Seeing different perspectives helps you develop a deeper understanding of the larger picture and empathy for the position of others.

Part 3 - Conclusion (and Caveats)

There are a couple of important pieces of information you need to take into consideration. Like all things, this solution comes with a ‘Warning: Use in Moderation’ label. It’s important to recognize that outsider perspectives do have limitations. The fact that outsiders come from outside the organization means they can’t have the same depth of knowledge on a particular product or the level of understanding about the group as those who are part of it.

Outsider perspectives can help you get to a solution. They aren’t likely not THE solution. The decision-makers (meaning you) need to recognize this distinction and plan accordingly. Seek to strike a balance between insider and outsider perspectives in order to get a well-rounded view of a situation (and the best solution to your problem!)

The second consideration is to make sure you start things off by clearly defining the problem for everyone involved. What is the scope? What are the ‘rules of engagement’ for everyone? What is the overall goal? Before embarking on the journey, all the stakeholders need to understand where they’re going and how they’ll get there (or they won’t even get on the bus).

If the process doesn’t start this way, you’ll keep getting more of the same. Sadly, there’s not some special magic no one told you about until now that will magically make all your problems go away. If it was that easy, someone would have figured out how to box it and sell it years ago. That leaves the tried-and-true method of good old hard work and ingenuity!

Lastly, be aware of the paralysis that comes when facing hard problems. It’s not uncommon! It’s hard to move when every path seems bad and every destination seems wrong. Just because everything seems murky doesn't mean you stay put. Every journey starts with a step (even if it’s a small one). Figure out the first step and take it. Plans can change. Solutions evolve over time. You just need to start. Anything that moves you forward is a step in the right direction!

Start looking for people who can offer an outside opinion. Sit down and write out your problem. Rough draft some rules of engagement you’d use if someone else asked you for advice with the same problem. When combined with clearly defined scope and rules of engagement, outsider perspectives will help you overcome the pitfalls we talked about earlier. Through thoughtful planning and deliberate action of everyone involved, outside perspectives will help you to find the solutions you need to get your edge back.

Thanks for reading! Please let me know what you think. I respond to all comments personally.

Also - please consider signing up for the Leitwolf newsletter!