The Hard Thing About “Digital Transformation”

The Hard thing about Digital Transformation by Mukesh Gupta


Everywhere you go on the internet, there is one thing that is prevalent. No, I am not talking about Donald Trump, though he seems to be prevalent almost everywhere as well. I am referring to “Digital Transformation”. I have been reading about digital transformation everywhere i go on the internet for sometime now and yet, I don’t yet see true success story of a brand or a business that has actually successfully gone through and transformed, in the true sense of transformation. The question is why is this so?

Any transformation is difficult, digital transformation, more so: 

As any leader who has attempted to change an organisation or a team of people will readily accept – change is difficult, both at a personal level and more so in a group. And if the change is not small but is at a scale where it can be called a transformation, the scale of difficulty goes up by a few notches. In the case of digital transformation, it is change at every level.

It is about how the business engages with their customers, partners, vendors and other stake holders. It is also about how they work within the organisation. It is also about how they think about these things. It is also especially difficult because this also requires everyone in the organisation to learn new tricks (and we all know how difficult it is for people who are senior enough in a organisation to first accept that they need to learn as well, then to go on to actually learn).

Is there a playbook for successful digital transformation? 

I don’t think so. If someone says that they have one, I would assume that they truly don’t understand the magnitude, complexity, customisation and the level of difficulty involved in running a digital transformation. No two organisations are the same and have the same challenges and hence can be transformed in the same way. So, that, in my opinion rules out having a playbook for digital transformation. Whatever approach one takes, it needs to be custom built for that specific organisation and developed in-house, maybe in consultation with external consultants.

So, What does that mean?

This means that digital transformation is a virgin territory. Every leader or an organisation will need to figure out how to traverse in this territory. Having said that, the same basic concepts that are important for every change project is applicable here.

Some of these concepts are:

  1. Self Realisation: As with every other change effort, it should start with self-realisation that there is a need for change or transformation. If you start a project for digital transformation, just because, everyone else seems to start one or every alternate vendor is talking about it, then you are doomed to fail, even before you start.
  2. Start with the why: Once the leader senses the need to change, it is important that they communicate this insight or understanding with their team. It would serve them well, if they are able to clearly articulate, why the need for change and what will happen if they don’t successfully change (we all know that negative consequences are more powerful motivators than positive outcomes).
  3. Then move to Where: Once it is clearly articulated and the teams buy-in the reason, why change is imminent, the leaders need to work with the team to create a vision of what the successful change could look like. While it is important for the leader to have a vision herself, it is equally important that they don’t share it with the team upfront, to avoid HiPPO’s (Highest paid person’s opinion) bias to take hold. Leaders would be surprised with the creativity and passion that could be unlocked within their teams, once they give them the permission to revv up their imagination and imagine what the future could look like.
  4. What would need to be true: Once the vision for the future is agreed upon, you might think about the assumptions that you have made while imagining the future. You can think of it as a series of “what would need to be true for __x__ to be real”.
  5. Experiment to test the assumptions: Once the assumptions have been identified, we need to create experiments to test these assumptions and learn from them. The learnings need to be communicated to the team and the vision updated accordingly.
  6. Pick a starting point: The easiest way to lose a change project is to go big. While there are change projects which are big and transformative, that succeed, the probability of such a project (specially, one which is going to be in unchartered territory) to succeed, is small enough for me to suggest that, it is best to start small. The way you do that is to pick a starting point. It could be as simple as updating your internal IT system to enable cross-functional collaboration or training employees on the basics of new technologies or how you engage with your customer in the sales cycle. I would pick a starting point that is totally in the control of the leadership team and doesn’t involve external stakeholders first. Also, the important point to remember in this step is that we need to pick something that forms the foundation on which we can build the transformation effort. Usually, it is about changing mindsets or toolsets, and in some cases both.
  7. Create a ripple effect: Once you have identified a starting point, enroll the people who will need to change to make the transformation work. Find ways to create some initial success and build on the success. Once you have successfully done transforming the first phase, pick the next point of transformation. Once you have done two and learnt what works (and more importantly, what doesn’t work) in your organisation, incorporate the learning back into the next phases. Once this is done, then look at involving external stakeholders.
  8. How to select the projects: There are multiple ways to select which areas should be picked for transformation and in what sequence. Some people pick the areas that can have the most impact, some pick the projects that are the easiest to successfully complete, some rely upon the recommendations made by consultants that they have engaged. My personal opinion is that we should pick the projects, just the way an architect builds a building. The most important is the foundation on which the entire building will rest. Then comes the walls followed by plumbing, electricals and finally fittings, flooring and finishing. The leader needs to discuss and decide what is this sequence for them. The only criteria is that each project’s success should make the next one easier to complete and succeed.
  9. Communication is the key: As any change manager would readily agree, it is critical that you monitor and report progress through good communication with the entire team. Regularly. All through the change effort.
  10. This transformation doesn’t stop: Unlike other change management projects, digital transformation is unlikely to have an end date or state. Also, because of all the rapid change that is happening in the world of technology, it is quite possible that you might have to re-visit your vision to ensure that it is still valid and the right one to go after. And due to this, I believe that the digital transformation would not end-up being a project but will become a way-of-life.


All of this means that while we all hear a lot of noise and too many people trying to sell their own IP on how to go through digital transformation, leaders need to be aware that it will take much more than that in order to truly transform to the digital era. It also might mean, that as a leader, you are the first person who needs to understand and personify the kind of person it takes to go through such a change initiative, so that others can learn and model them (the list of characteristics that they need to display is a topic for a separate post sometime soon).

In conclusion, I would just argue that

Digital transformation is not a project to complete, but a way-of-life to run your business by. Click To Tweet

I hope you have all the success in your journey.


How to Get Better at Dealing with Change

We live in an age where we see accelerating change all around us. Large, extremely successful businesses go bankrupt in a matter of years, if not quarters; companies with billion dollar evaluations are born in the matter of years; as consumers, there is something new that is becoming a rage almost every week.

Change is all around us. Whether we like it or not, we will have to deal with change – in our personal lives as well as in our professional lives.

The question then is the following:

Do we embrace change and benefit from it or resist change and remain stuck in a world that no longer exists?

Change in personal lives:

The speed at which things change in our personal lives is also unprecedented. There are new tools, products and services that are launched with the promise of redefining our lives. Some of them do and some of them don’t.

Having a sense of our true north:

When you are navigating change all around you, you need a map to help you navigate the change. If you don’t have a map, you at least need a compass, which can help you know where is the true north and thereby help you navigate the unknown territory. Today, it has become a lot more important and critical for each one of us to know what is our true north. What is most important and dear to us.

What are the musts (non-negotiables), shoulds (you would love to have/do if possible), could’s (non-critical but nice to have/do) and Won’ts (actively avoid) in your lives?

This clarity will help you identify changes, innovations and new opportunities that you can benefit from and also the changes, innovations and opportunities that you need to avoid.

Personal productivity:

Once you have defined your true north, actively look for opportunities that can help you make your life more productive and enjoyable.

Time is the only variable or asset that is non-renewable and depleting. So, block some time on your calendar to explore new innovations that will help you eliminate/automate activities from your life so that you get more time to do what is most important to you.

This approach will help you not only actively look for change in your life but also make it much more productive and a happier life.

Remember Rule No – 6:

In their book – The Art of Possibility, Rosamund Zanders and Benjamin Zanders share the story of a diplomat. The story goes like something this:

Two ministers were sitting together discussion matters of national importance, when one of the secretaries of the minister who was hosting the meeting came rushing in, all flustered and totally animated. The minister then tells her – remember rule no. 6. The moment she hears this, she totally transforms and becomes calm and walks out of the room.

A little later in the meeting, another assistant of the minister walks in hurriedly and tries to whisper something in the ears of the minister. The minister again tells his assistant – Remember rule no. 6 and he also calms down and bows and walks out of the meeting.

The visiting minister was now curious. He asks the host – if I may ask, what is rule no. 6?

The host replies – Never take yourself so god-damn seriously.

The visiting minister then asks – what if i may ask are the other rules?

The host replies – there are none.

The point is that in our day-to-day lives, we end up taking every little thing seriously. This is what leads to a lot of stress. Once we decide not to take ourselves so seriously, we start to slow down and that enables us to develop a longer term perspective and find some humour in all kinds of situations. This takes all the stress about impending change away, as fear and humour cant be room-mates.

Change in Professional Lives:

The pace at which organisational change their business models, their go-to-market strategies, their product mix, their org structures is unprecedented. In this scenario, there are a few things that you can do to not just embrace this change but also thrive in it:

Understand the reasoning behind the change:

The biggest reason why we fear change is because we don’t know what it will bring with it. As they say,

The fear of something is always worse than the actual thing.

The biggest reason why we resist change is because, forced change makes us feel out-of-control. We don’t like being out-of-control.

Once we understand the reason behind the change, we can feel a sense of control back. Also, once we understand the rationale, we can also understand what the change is driving us towards. Once we know the end-game, we can understand what is in store for us in the new reality.

We then need to use something that is innately a human trait – imagination.

We need to imagine the new reality and what would it look and feel like.

  • What would it take for someone to be successful in that reality?
  • Will our skill-sets be an asset in that reality or will they become liability?
    • If they are an asset, how can we build on that and showcase it to the right people (who would these right people be?)
    • If they become liability, what will need to be done now, so that we can change that and develop skills to become an asset instead?
  • What new opportunities and threats will the new reality bring with it?
  • How can we use these to become a more valuable contributor to the team and the organisation?

Once we have thought through these, the fear of change will reduce and will be replaced by an optimism for the new reality, as you will know what the new reality will look and feel like. Once you already know how you will succeed in that new reality, so there is nothing to fear about.

Stay away from gossips:

The biggest culprit of spreading fear of change is gossips in the organisation. Gossips happen when there is not enough communication from the leaders of the organisation about the reason for the change and the vision for the new reality.

If that is the case, then it is best to stay away from gossips. While it will be very tempting to participate in the gossips, it is extremely counter-productive as these gossips will only increase your anxiety and thereafter your fear for what the future holds. We already know that the fear of something is much worse than the thing itself.

So, lets do ourselves a favour and stay away from gossips.

Be a Corporate Adventurer:

The way we see ourselves makes a big differnce in how we deal with change coming our way. If we define ourselves as a corporate adventurer, who is out there in the wild to do new stuff, explore new territories, learn new things, meet new people and have fun along the way, then every change that is thrown at us becomes yet another adventure to go on.

Instead of becoming fearful of the change, we start looking at the new places this change will take us to, what kind of new people will we meet on the ride and what fun will we have all along.

Instead of feeling out-of-control, you will long for new change initiatives to be launched, so that you can go on your next adventure.

Attitude to change matters more than anything else. Lets invent one that suits us.

Find some humour in the situation:

Finally, it is important for each one of us to find some humour in our professional lives as well. Most of us have forgotten to have fun at work. Play or fun seems to be delegated to when we have leisure time.

In my experience, I have found that leaving fun or play to leisure time is a big mistake and one that we are all guilty of doing. Have some fun at work. Play. Find some humour in the little things in the office.


There is an inherently human trait that each one of us have – We see what we seek.

So, if we seek anxiety, we will find it all around us;

if we seek fear, we will find it all around us;

if we seek negativity, we will find it all around us;

This also means that

if we seek positivity, we will find it all around us;

if we seek opportunity, we will find it all around us;

if we seek fun, we will find it all around us;

if we seek adventure, we will find it all around us;

if we seek meaning, we will find it all around us.

So, instead of focusing on all the inherently negative emotions, lets start looking for all the positive things in our lives and in the changes that are forced on us and have one hell of a ride with it.

PS: Have some fun watching the below:

When its time to change, you have to rearrange…

PBTO27: Selfish, Scared and Stupid – A Guide to Navigating Change

Unexpected Change Ahead

In this episode of Pushing Beyond the Obvious, we host author and innovation consultant Dan Gregory to talk about the Impossible Institute and changing human behavior.

We are living today in a world that is rapidly changing and evolving. In order to navigate this ever changing, constantly evolving world and succeed, we need to be able to keep pace with the change. Some of it involves organisational change and personal change. I can tell by my personal experience and from what i read that neither organisational change nor personal change is not easy.

So, in order for us to succeed in such an environment, learning how to continuously and successfully change (our behavior and the behavior of our teams) is a critical meta skill to learn and master.

This has also led to an enormous amount of research being done in the behavior design space.

What Dan Gregory and Kieran Flanagan have done is to simplify the research and combine it with what have have learnt in working with transforming entrepreneurs and large organisations and create simple strategies for us to win this struggle with change in their book “Selfish, Scared and Stupid“.

They talk about evolutionary human nature to be selfish (self preservation), scared (survival instinct) and stupid (irrational or emotional) and how it is better to use these natural instincts to embrace change rather than fight it. They share simple strategies that we can use in our daily struggle with change to come out smiling and adopting the change.

In this conversation, Dan shares some of these strategies and also talks about the work that the Impossible institute does with entrepreneurs. He shares the approach that they take to radically alter the way entrepreneurs think about their businesses.

I enjoyed the conversation and learnt a lot. Hope you will do so as well.

You can reach Dan Gregory at @DanGregoryTII on twitter.


PBTO14: How do you change behavior of an experienced sales person with @DaveKahle

Who is on the show today:

In today’s episode, we have Dave Kahle. He is also known as the Growth Coach.

Why is he on the show

Dave Kahle is one of the world’s leading sales authorities. He’s the author of 12 books, including 11 Secrets of Time Management for Salespeople, and How to Sell Anything to Anyone Anytime.

He writes a weekly Ezine for salespeople; and has presented in 47 states and ten countries.

As a salesperson, he was the number one salesperson in the country for two different companies in two totally distinct industries.

For over 20 years, he’s been President of Kahle Way(r) Sales Systems, a sales training/consulting company. In that capacity, he’s trained tens of thousands of salespeople and sales managers.

What are we talking about

In this discussion we talk about how to change behavior of experienced sales executives. One of the difficult task of sales managers is to get their sales people to change their behavior (specifically the behavior of sales people who have or were successful in the past and need to change to adapt to the new realities.
Dave walks us through his 7 step process to help such experienced sales executives change and transform.
This discussion was inspired by a blog post that he had written. You can find the post with the same title as this episode here.

Buy his book

You can also buy her book on amazon by clicking on the book image below. This is an affiliate link.

You can connect with him at and on twitter @DaveKahle.

PS: Please do leave a rating or a review on iTunes if you really liked the episode 

A blog post that Dave mentioned:

Transforming Organization Culture

This weekend I happened to watch a play by “Yours Truly Theatre” titled “Bhagwaan Dhoondo“, which loosely translated means “The Search for your Own God”. It was by all means an enthralling performance, which ended with a standing ovation from the audience. It was funny, thought provoking and entertaining throughout.

What was most interesting thing about the play was that it was of a genre called “Interactive Theatre”, which is a kind of Improv theatre and has two parts to the play:

  1. The first part is rehearsed and performed by the actors. This part tells a story of the protagonist. It stops at a place, where the protagonist is at a cross-road and has a decision to make.
  2. The second part of the show is decided by the audience. The moderator of the play comes on stage and leads a discussion about the situation and what options does the protagonist have and what should he/she do in this situation. Based on the audience reactions, the actors then incorporate the feedback and play out the rest of the story impromptu.

When I stood applauding the performance, it stuck me that this would be a great way for an organization to design or transform its culture.

If  as a leader, you want to transform the culture of your organization, you want everyone in your organization to understand and act according to the new values.

Gather around your employees and get them to play out the situations that they face in their day-to-day work and stop them at a moment-of-truth, a moment where they need to make a decision and act on it, a decision that defines the culture of the organization. Now, stop the role play and ensue in a discussion about the various choices that the employees have at that juncture and let them offer their choices. Most of this will be based on the current culture. Now you can either continue to steer the discussion towards the decision that you want them to make as that will reflect the new culture you want to inculcate. Then get the same set of employees to improvise and enact the rest of the scene on this course.

In order to be successful, you as a leader need to be able to determine the Keystone habits of your organization that needs to be changed and use this exercise to influence that habit, which can then start an avalanche of change within the organization.

This method of influencing the culture of the organization has some significant benefits like:

  • This leaves no scope for ambiguity in the team as to how they are expected to behave in the specific scenarios that have been staged.
  • This can also bring forth all the other ramifications that need to be taken care of, all dependencies exposed, which can then be worked upon. It is in such details that most culture transformation exercises fail.
  • This also allows you to try the different options for the teams in a way that does not cost money or lost time.
  • This is also a fun activity for the team to do. Specially, when the team is able to exaggerate the situation a bit and is able to have some fun at themselves and the current policies.
  • This also creates a sense of caraderie among the team along with a sense of ownership for the new behavior as it was arrived together with them and not ordered by someone in the “Corporate”, who doesn’t understand a thing about how things work in reality. This substantially increases the odds for the new behavior to take root.

Do share your thoughts about this approach for culture transformation.

You can connect with me on twitterlinkedinfacebook or email.

You can also subscribe to my weekly newsletter here.

PS: Charles Duhigg talks about Keystone habits and how to change habits