Bob Dylan and What’s Wrong with IT Today – Part I


I decided to come back to my writing process with a musical approach and related to a topic we all see quite often, even if we are not paying attention or just deciding to look away. Let’s get right into it.

What’s the Bob Dylan Reference?

I’m not a Bob Dylan expert, but you don’t have to be quite knowledgeable to respect a Noble prize winning artist with almost 60 years of writing songs (started in 1959). The song that I’m referring in this case is “It’s Alright, Ma (I’m Only Bleeding)” (from album “Bring It All Back Home”, 1965) and the specific quote:

“Proves to warn that he not busy being born, is busy dying



I’m not going to go over the message around the entire song, there are already entire articles and papers published about that. I’m going to focus in the particular quote mentioned and how this relates to the IT culture.

Bob Dylan’s message in this quote is fairly simple: If you stop reinventing yourself, you’ve started dying. IT is no different, ever changing technologies and solutions as we have today require redefining yourself, your goals and paths moving forward.

In IT, as in many other industries, the challenge is to live and grow with a constant presence of uncertainty and change. We feel obligated to be aware that the notion of failing to continue growing, is the same as killing our careers.

How many of us have seen IT people, roles, departments or even entire organizations with a steady and unchanged definition and position around technology in general? Even though we can see that as a very common factor in the industry, how many of us are actually convinced or willing to make the change for a transformative approach?


Article Series Approach

The idea in this series is to go over the common scenarios I’ve discovered and discussed with companies around the true IT Transformation present in most of these organizations.

Being “true IT Transformation” the key term. As you probably know, some organizations or leaders refer to IT or Digital Transformation as simply a way to represent budget reduction or asking to implement that fancy new definition in today’s industry (some of them call it “cloud”, “big data”, “blockchain”, you name it) but without any true strategy behind it.

The first section I’ll cover will be the “Busy Dying” portion, which is the summary of some of the common bad habits present around IT and companies. Some of the behaviors that define an IT organization that can’t or won’t innovate itself and the business they are supporting.

The second section will be the series of recommendations and best practices I’ve seen IT departments take in order to truly transform themselves, the “Busy Being Born”.

Ironically (or not), we’ll start with the part that relates to “dying”, this is needed in order to comprehend and assimilate the areas where we may be having problems or at least there’s room of improvement. If we don’t acknowledge this first, will most likely mean that any innovative approach, “being born”, will be a new thing where old habits will prevail and nothing changes.

There must be a transparent and honest assessment of the “as-is” environment in order to be ready to define the “to-be” state. I’ve learned that this is something any organization should do, it doesn’t matter if you just have a small shop or you are a Fortune 50.


Busy Dying: Business Disconnect

This is by far the most common discussion topic that I’m sure most of us already heard enough about it. After all, IT can’t thrive if it’s not collaborating with the business to succeed.

business concept conflict megaphone

We will also notice that some of these areas about to cover in this issue are related to other topics described later in this article.

I would like to list some of the most common scenarios and talking points I’ve found, including the different perspectives between IT and the business itself. Hopefully, if you are starting the path of defining your current state, some of these should sound familiar:

The IT Perspective about the Business Disconnect

  • “How can we add value within IT if we don’t have any insight into business planning?”
  • “Our IT management does not have a seat at the table when important business decisions are being made”
  • “We don’t have the authority and/or funding to do what needs to get done”
  • “We keep getting requests to reduce our IT budget in order to support other business units”
  • “IT is not invited to participate on key business initiatives unless is absolutely necessary”
  • “How can we look for innovation in a corporate culture that’s deadline driven?”
  • “We have to provide 24x7x365 support and almost all of our man hours to maintain old and complex applications”
  • “Business is asking us to implement nice and shiny dashboards and get a brand new look for their day to day apps, but still our systems are supporting legacy applications the business is not willing to change”.

The Business Perspective about the IT Disconnect

  • “IT is telling us that we have to provide funding. How much of their development should come out of our budget?”
  • “Funding should support the business needs and not IT’s”
  • “How do we get CIO/IT Director commitment around fulfilling corporate objectives?”
  • “IT seems more interested on resume building instead of driving business value”
  • “We don’t understand when IT is talking to us”
  • “We don’t have any option to obtain support if IT says they’re too busy”
  • “How can we trust in IT when the organization keeps changing their technical personnel constantly?”

As we can see, some of these scenarios could be related to communication issues and not necessarily to unwillingness to support from one to the other. I’ve received some of these similar contradictory comments within the same meeting between IT and business leadership.

We need to understand within IT that if we are looking to lead with innovation but the business people are not actively engaged, as much as you can promise that innovation is coming, it probably won’t mean much to them.

The other key takeaway regarding this is that, as long as business stakeholders stay alienated from IT, they will make assumptions about what IT can and can’t deliver. Which is a quite dangerous to say the least.

Another big misconception with IT departments today is that they confuse saying yes to everything with being a business driven department. Saying yes to any ask doesn’t make you automatically understand and prioritize properly what the business really needs, on the contrary. Most likely in order to say yes to something you had to say no to different ask.


Busy Dying: Lack of Training and Effective R&D

When a company says they invest 20% of their time/budget around research and development, in my mind I’m leaning more to a 2% being the real percentage.

As you can imagine, this does not relies only on the business side “allowing” IT to obtain the proper training and knowledge, it also relies on IT being able to prioritize accordingly and having a good sense of strategy around the research and training we are looking for.

There’s some clear reasoning around the business comment mentioned earlier about IT being more interested on resume building and getting that really nice certification that few people have. Therefore, do we understand what are the key business asks that we need to support and therefore commit with R&D according a business prioritization? Have we formalized that plan and share that with the business to obtain feedback?

There’s seem to be a misconception of IT people that believe they are being hired solely because of their specific skillsets/experience; the truth is you are being hired to support a business requirement.

And of course on the other side, organizations and business leadership must have the willingness to support IT if innovation is required. Making assumptions that IT by default will always have free time and budget available to support their own R&D is an erroneous belief.


There’s another aspect that IT suffers regarding R&D based on the amount of new solutions and technologies being released on daily basis, it could generate confusion and “paralysis” from IT leadership on deciding what is the right approach and solutions to start investing, and the “easy button” in most cases tend to not to invest on anything instead of making a mistake. This, again, has to do primarily with the strategy behind and having a business integration.


Busy Dying: Fear of Strategy Definition

So, what are we talking about when we say “strategy”? Basically strategy is the craft we follow on figuring out which purposes are both worth pursuing and capable of being accomplished, with the main objective of gaining competitive advantage.

The key aspect to understand about it is that building your strategy is a never ending journey, especially around technology. With solutions and requirements that constantly change, strategy is just something we should define and revise periodically.

The problem with strategy definition and IT is that seems outside of everyone’s comfort zone; there are certain IT leaders that feel their main focus should be around defining the right approach for platforms operations. In addition, that approach is mostly concentrated around resource allocation, budget and IT projects, but without any innovative or strategic quality.

What some IT leaders call IT strategy definition ends up being operational planning to keep the lights on.

On the the continuous quest of strategy definition and adaptability is fundamental to be inherited from an organizational culture. It’s quite challenging for an innovative IT leadership to succeed if the organizational leadership is saying “Don’t worry about it, we’ll be just fine with the solutions we have now”.

After all, “culture eats strategy for breakfast”.

“It’s OK. We’ll be fine”

Those are the words that first came out from BlackBerry CEO, Jim Balsillie, to Mike Lazaridis, the founder and vice chairman of BlackBerry at the time, when the iPhone was first launched in 2007.

Jim Balsillie and Mike Lazaridis, the good old days for Blackberry

Lazaridis was so amazed with Apple’s product that called his CEO, Balsillie, to review the launch video and the features of the smartphone that changed the industry entirely.

Blackberry’s CEO was confident that, because of iPhone’s poor battery, security concerns and other aspects, the BlackBerry market control in the Enterprise space was not even close to feel threatened. “It’s OK. We’ll be fine” said Balsillie to Lazaridis. The company’s leadership shared the same confident with a “not to worry” message to their entire organization.

We all know what happened. BlackBerry (ironically enough originally called RIM – “Research in Motion”) came from a +$1.9B profit on yearly basis to -$5.8B deficit in less than 5 years.

Unfortunately there are CEOs that, when they connect strategy and IT, it’s usually in the context of saving costs or outsourcing systems and skills.


Busy Dying: IT with No Connection with the Rest of the Organization

This is related to the business disconnect mentioned earlier, but an IT organization with a clear idea of what the business is requiring can still be failing on connecting and collaborating with other areas within the organization.

Being “too busy” to talk with HR around their onboarding process, or saying “not our priority” to support the new campaign for the Marketing department, it is also another way of failing.

Have you seen an IT department that is defined as successful in an organization but has little to no communication with other departments?


Busy Dying: Prioritizing Formal Processes and SLAs instead of Trust and Integration

Every IT organization that has been around for some time will have formal processes and governance models that are required to be consistent with the services you are providing. But there are some drawbacks that some of these organizations fail to see as areas of improvement.

A good and simple example are the IT committees designed to revise and approve requirements. Sometimes these committees will review every request made to IT, even the simplest ones. This, if not designed properly, can slow things down tremendously and generate a lot of frustrated stakeholders. Some of the issues residing here could be around having a lot of members in these committees, making the decision process longer since generating consensus in a large group is always harder.


Service Level Agreements (SLAs) can also represent a trap for IT. There are IT organizations that treat SLAs as their main contract vehicle and try to shield them behind it at all cost. In those cases, IT just stops worrying about the end result or business value, as long as IT is respecting the contract, they feel like their job is done. Sometimes these agreement contracts are outdated or inadequate, considering goals that are no longer the same since the business goals might have changed as well.


Busy Dying: Lack of an Offering and Failure to Provide New Services Periodically

Probably if you are not offering a new service every month, you may be starting to lose credibility and trust within your organization.

If the problem resides on the fact that IT is not able to offer new and enhanced services because they are still supporting old legacy applications, which may have been with the company for +20 years, they are slow and outdated, we must remember that the organization’s perception is that IT is the one slow and outdated. We, as IT, are tied to the perception generated by the systems we support.

These new services IT should offer periodically are not usually required to be complex solutions that radically change the organization, it could be as simple as new set of applications, improving recurrent communications, etc. These interactions and new offerings will facilitate the legitimization process for the IT organization. Even if you are limited, if you are showing a clear intention to add value, your actions will do the talking.


Busy Dying: IT Only Being Measured to Keep Lights On

There’s a common behavior in most organizations around their CEO or leadership missing the opportunity on providing clear and valuable performance metrics. It becomes more relevant and impactful for IT when there’s a CEO not very comfortable around technology in general.

Unfortunately there are plenty of CEOs and CFOs continue to measure IT on the trendiness of their smart devices, email uptime, and office applications. In addition to that, this leadership is constantly revising IT costs, system availability and help desk response time as key metrics. This represents a huge challenge for IT to maintain a good reputation and relationship while you need to innovate.


There’s also another recurrent discussion from leadership about Total Cost of Ownership (TCO), usually oriented on reducing these costs as mentioned earlier. TCO discussions don’t care about benefits, even more, they tend to discourage benefits and value. The explanation for this is simple: The easiest way to cut costs is to support technology that is less functional and capable; even though some would not refer to this concept literally as described, and probably use terms like “optimization” or “efficiency”. If you reduce the utilization of a service, you are reducing costs.

There’s a reality behind all this, IT needs to excel at running the day-to-day platforms so you can discuss going beyond the activities around keeping the lights on. Most of the times when we hear about an IT leader that was removed from his/her position is due an operational failure; it is really uncommon to hear about a person being removed because they were succeeding in operating IT but failing to incorporate innovation.


Busy Dying: Lack of Understanding between Important and Urgent

Managing your time comes down to one important thing: understanding the difference between importance and urgency. A big part of the challenge of time management emerges when you start to lose the sense of importance.

Email is probably the worst vehicle for conveying urgent, time-sensitive information. Soon as you sit in your computer, emails start coming up and you feel the need to start answering them, if you are really considerate you’ll start replying the older ones first (typically received the night before or really early in the morning) since those people have been waiting longer than others. It feels urgent, but it isn’t urgent.

Differentiating important with urgent tends to be more of an intuitive decision. The propensity for confusion here is related about IT, in general, prioritizes on short-term concerns with faster results than long-term initiatives. The intention is to go deeper around this topic in the next article, but the best reference around understanding the difference relates to the Eisenhower Decision Matrix.

Eisenhower Matrix
Eisenhower Matrix summary from

Related to some of the discussions earlier, IT feels far more at ease solving technical challenges around the platforms they are supporting. Technically inclined staff are more comfortable playing in the technology sandbox than solving business problems. So, IT might “feel the urgency” to solve a challenge that does not have much criticality instead of supporting a business request that does not involve a technical challenge.


Busy Dying: High Dependency on Manual Provisioning and Discarding Self-Service

A recent report from McKinsey suggests that half of the job functions performed today by people could be automated using existing technology. This does not represent less jobs for IT, it means there should be more freedom to be more strategic.

If you are able to demonstrate real value, no one will eliminate your job. And we have to embrace that a lot of times in order to show value, you need to think strategically. Even more, these McKinsey reports state that jobs may grow in the upcoming years since productivity increases and, with the progression in technology, more and new type of roles will be required in IT.

We’ve all seen our fair share of scenarios where shadow IT takes preference among power users/organizations (i.e. development teams). Shadow IT happens, BYOD has become BYOIT for some companies. If they can obtain the full environment they need within minutes by doing it on their own, or alternatively they can ask IT and get it after several days or weeks, the selection process it’s not that hard. And this problem isn’t an intrinsic limitation from IT, it’s a choice.

Today, lots of IT is happening outside the IT department, mostly in the form of SaaS/PaaS brought in by business managers as islands of automation. We must be ready for that.

With millennials being the workforce of the future (estimated 75% by 2025) it is nearly impossible to ignore self-service capabilities. Millennials do not require much training around applications, that’s a known fact, most of today’s productivity (like most smartphone apps) is represented by intuitive processes. Our IT services need to be flexible, accessible, engaging and predictable in order to keep the final users invested.

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