How to Kick-Start Digital Transformation Without CEO Support?

July 11, 2017

Many IT leaders in mid-sized businesses strongly believe that digital technologies are undervalued by their employers and that they could be playing a much more influential role in shaping the future of the business.

If you are such an IT leader, however, you will also know just how hard it is to convince other senior leaders (including the CEO) to see the same exciting future you see.

Your one option is to chip away at their reluctance and hope they will come around over time.

You just don't know how much time this will take and your past experiences are not really encouraging...

Or you could adopt our proven 7-step kick-start guide and gain serious momentum in as little as 3 months....

The choice is yours!

Which one will it be?


1. Decide to Become a Digital Change Agent

If you are really serious about embedding digital into every aspect of the business, you have to start with yourself and make sure you are really committed towards the overall goal of starting your business on a digital transformation (DX) journey.

To do this, your first challenge is to ensure that your IT management practices in general, and project coordinationservice desk and IT budget in particular, are well implemented and respected.

Without these basics in place, any mention of the word "digital" or a desire to contribute at a more strategic level will just be met with scepticism.

If your IT function faces some critical challenges, and you feel it is not all your fault, you may consider calling on an external business technology advisor who often can, due to their outsider status, overcome structural obstacles with ease whereas anybody within the business would just struggle to achieve the same.

Once your house is in order, spend some time to properly understand what is meant by digital or digital transformation (DX), what the specific challenges are for mid-sized businesses and why it is so important to get started (these links all point to previous, well-researched blog articles).

Next you need to buy into the notion that every mid-sized business, including the one you currently work for, will, within the next 3 years, appoint a business-focused CIO.

This means there is a massive growth and career development opportunity if you move forward and find ways to deliver value to your organisation through adopting digital.

Unfortunately, the flip-side is also true.

There is significant risk to your career ambitions if you fail to figure out how to accelerate the adoption of digital and your CEO is forced to appoint somebody else ahead of you to fulfil this strategic role you covet so much.

This is quite possibly a big thought for you and it might be hard to swallow.

Don't worry, you are not alone!  

My advice would be to take your time and make a real effort to come to grips with these implications.

Fortunately, there are at least three complementary approaches you can use to further build your personal business case for DX:

  1. Read up on the theory, watch case studies and otherwise immerse yourself in topics relating to digital in your industry. You will be amazed at just how much info there is available free of charge.
  2. Get out of your IT silo and informally chat with other leaders in the business. Ask them about the potential for technology in their function and listen carefully when they talk about the business problems they are trying to solve. Not everybody will respond to your outreach efforts, but there will be some individuals that have just waited for this opportunity to engage with IT about their real business challenges.
  3. Broaden your horizons and become active in a CIO community, join a Mastermind Group or even take up formal studies in the field of Business Technology Management (for some ideas check out "Career Development Options for IT Managers in South Africa").

The final and most important part in this step is to make a personal commitment towards growth and choose to become a change agent for digital (think Chief Digital Officer) in addition to your regular IT management duties.

What this means is that you will have to be prepared to lead boldly and without much initial support from other leaders.

It also means that you will sometimes have to embrace the leadership mindset of:

Ask for forgiveness, rather than permission!

2. Prioritise Digital Culture Above Digital Technologies

Next up you need to rid yourself of the notion that all IT value can be reduced to some or other technical project that delivers a specific business outcome and can be managed as part of your project portfolio.

Huh? But isn't digital transformation (DX) just another project that can be managed within the existing IT management paradigm?

Of course, DX is a project, but whereas regular IT projects are primarily concerned with implementing some new technology, DX primarily focuses on changing mindsets and culture and only then asks what technology needs to change as a result.

The best way to explain this is to move away from digital transformation for a moment and rather think about the almost universal need for greater business agility.

In the good old days, a business could introduce a new product and know it had a good number of years to capitalise on it as it traversed the various stages of the product life cycle.

Due to a number of really major forces such as globalisation, cloud, mobile and rising consumer expectations, however, product life cycles everywhere have been shrinking...

... and they still continue to shrink with the end result being that there is a rising demand for organisations to continuously rejuvenate their product line-up.

In short, they need to embrace change as the new normal and innovate like mad in all areas of their business.

While it is easy to see why innovation should incorporate digital tools and technologies it is even more obvious to everyone that we have to change many of our default behaviours and approaches in order to achieve true business agility.

And this really has very little to do with technology!

Cap Gemini did a land-mark study of 400 large organisations and found a high correlation between increased business profitability and a primary focus on what they call "Transformation Management Intensity" (which focuses on the management aspects of DX) as contrasted with a focus on "Digital Intensity" alone (which measures the sophistication of digital technologies employed).

Of course, the most successful organisations are the ones that focus on both the cultural elements and on finding new ways to leverage digital technologies, but the overall message is very clear:

Changing digital culture should be prioritised above just implementing new digital technologies.

Yes, you have read correctly.

If you want to be successful at DX, you have to understand that your primary challenge will be to transform the hearts and minds of leaders around you to become more agile and accept that technology is now everybody's business.

Only move on to the next step when you can successfully resist the urge to see DX as just a series of technology projects.

3. Understand Digital Readiness of the Business

Considering that successful DX is more biased towards organisational change than technology, it is reasonable to assume you are somewhat of a novice in this department.

Unfortunately for you, this has to change if you want to have an impact and contribute true business value as opposed to just being the "nuts and bolts person who keeps the infrastructure running".

Start by collecting information that helps you understand the inner workings and priorities of the business as it is today.

Some of it you may already have, but here is a more complete list to get you started:

  • What is the annual turnover of the business?
  • What are the annual operating expenses of the business?
  • What is the total IT budget (including salaries) and how does this compare to the operating expenses of the business?
  • What are the strengths and weaknesses of the business as well as the opportunities and threats it faces?
  • How do reporting structures of the business work? Can you lay your hands on an up-to-date organogram?
  • What are the strategic business priorities for the next three years? For the next year? 
  • How does the business measure success? What are its KPIs? Is data about current performance easily available to key employees?
  • What major business technology projects are either currently running or are in the pipeline for the next year(s)?
  • How does the business feel about the IT services provided by your department? Are things running smoothly or are there critical issues that require attention?

Your business may not have all of this info available, but just asking for it can already raise your profile as few have ever heard their IT leader ask such questions.

Next you need to read up on one of the many digital transformation frameworks available and understand how digitally mature your organisation is.

The Xuviate DX Maturity Model has been specifically developed for the needs of mid-sized businesses and identifies the organisational structure as one of the major determinants of overall digital maturity.

Before you get despondent about just how much work there is ahead of you, I want you to know that most businesses are still classified as either Stage 0 or 1 and still have some way to go before they reach the pivotal Stage 3 when digital is embraced by all senior leaders.

Armed with this information you will be able to greatly narrow down your options and have a much better understanding of the challenges you are likely to encounter on your journey.

Ok, so this was the easy part.

Now you need to engage an even broader base and find out what the current digital readiness of the business is, as perceived by all the stakeholders.

This is important for three reasons:

  1. To generate awareness and talking points for digital opportunities within the business (in many cases, this will be the first time that people really engage with the promise and realities of "digital in the workplace");
  2. To benchmark your current digital readiness along many dimensions and within all teams so that you can plan improvement projects and measure progress over time;
  3. To create your first real chance to engage with the broader employee base and leadership on a topic that is not directly related to back-end IT services and support. The feedback can be invaluable to understand how much natural momentum there is for DX and where your natural digital supporters are. 

4. Assemble Your Team of Digital Mavericks

Since you are operating in an environment where you don't yet have formal approval nor active leadership support for digital transformation, it is absolutely critical to lead by example ("show", rather than "tell") and get some significant quick-wins under the belt.

Key to this is finding a group of volunteers who are unhappy with the status quo on digital and are prepared to go the extra mile and support you in your quest.

Although one can go to great lengths in selecting just the right team of between 5 and 15 individuals, there is often not really much choice and your selection criteria are usually straight forward.

At the minimum, only include individuals who

  • believe that the business could leverage technology a lot better, 
  • are eager to contribute, 
  • are willing to prioritise team activities and commitments without affecting any of their regular duties and responsibilities (this is why we call these people mavericks), 
  • who get things done and are generally considered to be "doers" (i.e. people who have relevant skills) instead of the "managers" and
  • who may have key competencies necessary to create a good all-round team. What works well and creates many options later on, is to include an IT generalist (this could be you) and, if available, a data specialist and a business analyst.

In some businesses the established hierarchy is so strong that you first need to get one senior business leader to act as a sponsor for the initiative and help create the right conditions for this cross-functional team of mavericks to get together and work on a quick-win project (outside of normal governance processes).

When you first invite others to your team of "Innovation Mavericks", create a sense of excitement and make it clear how special it will be to become part of this group.

What follows is an example of such an email invite that was sent to everybody who participated in the DX Readiness Analysis of the previous step.

Expend some political capital if you need to, but make sure that you under no circumstances compromise and include individuals that do not want to be there!

5. Choose a Significant Quick-Win Project

If you have diligently done your preparation up to this point, you will now be ready to schedule an inaugural workshop with your band of mavericks to officially form the team and identify one significant quick-win project that, if achieved, will create massive momentum for your initiative.

Identifying a good candidate project from the many ideas that will no doubt be put forward by the team, however, is usually not trivial.

What helps is to have a strong set of guiding policies to distinguish the really great ideas from the more questionable, insignificant or overly risky ones.

By far the most important constraint you should set for the group is to agree on just how ambitious you will want to be in your project selection and then find a way to express this in terms senior business leaders will understand well.

There are few outcomes that are more visible than achieving a substantial ROI (10 times?) within a short period of time (1 year?) after the project commences, but there are many other operational and industry-specific metrics that could work just as well.

Here are some more guidelines (arranged in no particular order) to help you during the selection process:

  • Requires no or little additional budget - Asking for money (irrespective of how promising the reason) always slows you down. Only plan to use funds for which you have already budgeted or could otherwise easily obtain funding (e.g. from your own "slush fund").
  • Aligns well with company strategy - To avoid complications be careful of choosing improvement or innovation projects that cannot easily fit into the company strategy or plan.
  • No impact on other significant deliverables - Since this is a rogue unit you need to be careful to not upset the status quo and affect any of the other critical deliverables.
  • Digital technologies play a significant role - Although many other projects could benefit from the more collaborative and team-based approach you are following, your particular focus is on creating value by adopting digital technologies and mindsets.
  • Duration of 3 or less months - By the very definition of a quick-win you need to keep the delivery timeline short (3 months or less) and largely within your own control.
  • Requires significant cross-function effort - Functional silos have been identified as the biggest impediment to business agility and this project should demonstrate just how much value there could be when collaborating better across teams to implement non-trivial projects. 
  • Doesn't require significant new digital capabilities - Although your greatest challenge is to nurture digital capabilities and mindsets over time, you need to initially limit yourself to only use the capabilities that are readily available to the team. The very success of this project will provide the momentum to invest more broadly in DX capabilities.

With this in place, team members can now proceed to list all their candidates for possible quick-win projects.

Don't worry if this is a long list and some of the ideas obviously do not fit witin the guidelines set out before.  

The objective is to think outside the box without too much scrutiny early on in the process and only at a later stage to filter out any ideas that obviously don't fit the criteria.

Left standing is a list of good candidates and any number of facilitating techniques can now be used to select the top quick-win project candidate for the team to work on.

6. Embrace Agile to Deliver Quick-Win Project

You probably noticed something odd during the guidelines section of the previous step.

Instead of starting with the requirements of the quick-win project (i.e. features) and asking how much time and budget will be needed to complete it, we rather chose to constrain ourselves on the time and budget dimensions, leaving the features fairly flexible.

Turning the triple-constraint of traditional project management (also called the Iron triangle) on its head to make way for a more flexible implementation approach is one of the most critical paradigm shifts of what is known as Agile Project Management.

The rationale for introducing this thinking here is best expressed by Jim Highsmith, one of the original founders of the Agile movement:

If a business pursues "repeatable manufacturing", traditional project management methods work, but if the business pursues "reliable innovation", then the Agile Project Management methodology is more likely to yield good results.

For a primer on Agile and some interesting thoughts on Agile and IT you may want to read "The Speed of Agility - How IT is Teaching Business a Lesson".

The way we constrain our quick-win project, however, is not the only concept we borrow from Agile and there are quite a few other concepts we can learn from to ensure we can deliver maximum user value in the shortest amount of time.

The high-level processes to execute our quick-win project and drive results can now be mapped out as follows:

a) Define Project Scope

It is finally time to get down to the nitty-gritty of really understanding the vision for our project, its scope, all role-players involved, dependencies and assumptions, hypotheses to be tested, risks as well as any other pertinent details to help your team properly understand the outcomes they are looking for.

Two critical roles that need to be defined and assigned are the roles of the:

  • Product Owner - the individual who is acting as the customer and will be intimately involved during all major stages of the project.
  • Project Coordinator - the individual best positioned to manage the overall process and remove obstacles for individual team members. Will be very involved during all stages of the project.

There are many templates to use and you may already have your own for defining the scope of projects.

If not, Lean-Agile consultancy AgendaShift adapted the Toyota A3 problem solving method and created a template that is useful for our purposes.

For more info and a download link go here.

b) Develop Feature Backlog

Next you need to convert the project vision into a list of system and/or user features (stated as valuable outcomes) that need to implemented.

In Scrum, the most popular Agile methodology, this list is called the Backlog and it will be the source of work items for the various team members as the project progresses.

c) Select Work Items for First Sprint

One of the mantras of Agile is "release early, release often".

The idea is to get a working version of a product or solution into the hands of end-users after every short product development iteration (aka Sprint) for prompt feedback and course-corrections. 

In fact, due to the flexibility of Agile, course-corrections are embraced by the entire team to create real value for end-users along every step of the journey.

Sprints are usually between 1 and 4 weeks long with 1 or 2 week Sprints a more obvious choice for our quick-win project initiative.

Once a duration has been decided on, related Backlog items are assigned and moved into the first Sprint interval using a Kanban board to visualise and prioritise the work.

Since you are operating in a mid-sized business and also lead a Maverick team you will have to pay even more attention to resource availability (very important as there are other commitments team members have), complexity of the work required and other dependencies that may affect delivery.

d) Maintain Flow Through Frequent Check-In Meetings

To maintain flow during a Sprint and deliver meaningful results it is essential to schedule a short daily or bi-weekly "stand-up" meeting to report on progress since the last check-in, current focus of each member and any issues that need resolving.

To keep the meetings short and on-target (between 5 and 15 minutes), the Project Coordinator commits to resolving issues and/or conflicts off-line with affected individuals.

e) Review Progress and Plan Next Sprint

At the end of the Sprint it is time to review overall progress, release the next prototype or deliverable and assign work from the Backlog to the next Sprint.   

This is also the best time to consider the implications of user feedback and modify the actual Backlog to incorporate learnings from the previous Sprint.

What happens during these sessions is extremely valuable and your best tool for ensuring the project you have selected will actually deliver the value you are looking for.

A meeting of this nature should normally not take more than 2 hours.

f) Start Simple and Refine Over Time

It is very important to keep the process as simple as possible and to only refine once the team gains confidence with the new way of working.

One of the decisions best left to a later stage is to introduce a new software tool to facilitate communication, visualise the Backlog, view work-in-progress in Kanban style and provide an online home for all documentation.

If the organisation, however, already uses a product such as Slack or Microsoft Teams/Planner it may make sense to leverage this capability earlier and create some more momentum for the tools your business already owns.

7. Complete Quick-Win Project and Celebrate Success

At the end of the period set aside for the quick-win project, the Agile delivery process will have created an immediately usable outcome for the Product Owner and should be well on track to deliver against the significant project expectations your team agreed on in step 5.

At the Project Close Meeting (half-a-day should be enough), the team gets together for a final time to dispense with high-fives and evaluate the entire process to extract any learnings for even more ambitious projects.

A nice touch would be to take the team out and celebrate as they have just achieved something significant and proven that it is possible to deliver a major outcome within a short period of time and without any major support of the business. 

Just imagine what effect this will have on everybody else who suddenly also realises that they would like to be part of something great that really moves the needle in a positive way?

Of course, the CEO and other senior business leaders should be invited as part of your strategy to create buy-in for the next stages of your DX initiative.

Conclusion - On to Your Next, More Ambitious Project

It is absolute magic when people for the first time realise just how much potential there is for applying digital solutions to solve long-standing business problems in record-time. 

The work you have just completed should have brought you a lot closer to this stage (if you are not already there) and you now need to carefully plan your next, more ambitious project to further improve digital maturity and embed digital thinking even deeper throughout the business.

While you will continue to evolve the approach introduced in this article, you also have to start investing effort to advance the critical digital business capabilities and culture identified in step 3 when you did the DX Readiness Assessment.

With the good-will you have just earned, you should in fact be in a good position to actually re-run the assessment and this time get a lot more actionable and engaged input from your stakeholders. 

And this will be the true win of this exercise as it will create the platform for starting your work on the people-transformation that is so important to any DX journey.

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About the author

DX Sensei, Mastermind Facilitator, Abundance Thinker or CEO, call me what you like, but know this: I am extremely passionate about helping IT leaders from mid-sized businesses discover their true potential and realise just how important they are to helping their employer survive and thrive in our increasingly digital world.

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