18 months ago, I adopted the Chief Technology Officer (CTO) role at a group of companies, which is responsible for administering approximately 750 pension schemes. 

With £250M+ of assets under administration, 1,000+ clients and 30+ members of staff, it was always going to be a big challenge. 

When you also consider that almost everything was being done via email and phone calls, with 30+ disparate systems being used behind the scenes, the challenge went to a whole new level of complexity. 

So, what was the mission? 

Well, as with with most missions, it came down to identifying and solving a key set of problems. 

In this case, the key problems centred around:

Thus, the solution needed to deliver against 3 key objectives, namely:

So, what was the plan?

Well, it is my view that before attempting to solve any problem, one needs to develop a very deep understanding of it.

This involves the asking of questions. A lot of questions. Often the same questions asked in different ways, sometimes of the same people and sometimes of different people.

Gaining a deep understanding of problems also requires open-mindedness, humility and patience, along with great interpersonal and communication skills.

On the subject of interpersonal and communication skills, it is of paramount importance that you create an environment, in which people feel safe to speak freely and share all their knowledge, frustrations and ideas with you. Human psychology is a very powerful thing. You will do well to understand and respect it. One of the best books I've ever read about psychological safety and creating a great culture is The Culture Code: The Secrets of Highly Successful Groups by Daniel Coyle. 

This part of the process is all about building an intelligence picture. Having gathered all the intelligence, the next challenge is figuring out what to do with it. The key thing to avoid at this stage of the process, is jumping to conclusions.

It is mission-critical that you entirely disregard how things are being done currently and embrace first principles thinking. In the immortal quote, often attributed to Henry Ford "If I had asked people what they wanted, they would have said faster horses." This is the trap, which must be avoided when considering how best to solve any particular problem.

Imagine all the pieces of intelligence you have gathered, as being pieces of a jigsaw puzzle. The key, is to lay all these pieces out on the table, but before considering how best to put them together, you should first consider which pieces are missing and which pieces can be disregarded.

Once you have asked enough questions and applied sufficient levels of first principles thinking, solutions will start to present themselves.

At this stage, it is essential to think in terms of a Minimum Viable Product (MVP) and focus on delivering tangible results, as quickly as possible. This will instil confidence in the team, secure buy-in from the sceptics and help to establish momentum.

In delivering the MVP, particularly if a lot of programming work is involved, I would encourage you to create a focussed environment for yourself, which is free of distractions. Doing so will allow you to be far more productive. If you'd like to dig deeper into this topic, I would encourage you to read Deep Work: Rules for Focussed Success in a Distracted World by Cal Newport.

In line with the teachings of The Lean Startup by Eric Ries, once you have your MVP, you should waste no time in shipping it, so that you can gather real-world feedback, which can inform your next steps on the journey of continuous improvement.

The thing to keep in mind, as you continuously iterate upon your MVP, is that technological solutions alone, are not enough to transform an organisation. You also have to support your customers, team members and key stakeholders at every stage of the process, so they work with, rather than against you and the changes you're trying to implement.

You can be assured of meeting with resistance at every stage of the journey, often very staunch resistance from certain quarters. Your challenge, as a leader who is tasked with delivering the technological transformation, is to figure out how to overcome that resistance and keep the mission on track. At times, you will find the process deeply frustrating and painful. For the chess enthusiasts out there, you can think of this process as a game against a particularly cunning opponent. Your challenge is to always find the move, which will allow to keep moving towards the endgame and ultimate victory. Having the full backing and support of the executive team will be mission-critical, so be sure to work very closely with them. 

Depending on the number of people involved, you are likely to encounter tough decisions along the way. It is all but guaranteed that some people will embrace the change and others will rally against it. Where you encounter resistance, sometimes it will be possible to secure buy-in from people. Other times, no matter what you do, some people will persist in working against you and trying to sabotage your efforts. In such cases, you will be left with no choice but to remove these people from the project and potentially the company, as anything else would result in mission-failure, which is not an option. In such situations, I would encourage you to trust your instincts, whilst being tough but fair, in the pursuit of excellence. 

At every stage of the transformation process, you will need to strike the balance between deep thought and focussed action. Where in doubt, I would encourage you to be pragmatic, in finding creative ways to retain momentum and keep moving forwards.

Likewise, in the wise words of Warren Buffet, I would encourage you to identify and remain within your own "circle of competence." To this end, effective collaboration is absolutely essential, so focus on building a team and staying in your lane. 

I'm glad to report, that in the case of my project, whilst there remains a great deal of work still to be done, much has been accomplished and things are continuing to move in the right direction. 

When working to deliver your own technological transformation, I would encourage you to heed the hard-earned lessons contained in this article and to keep the faith in your own abilities, when working through the many challenges, which you will inevitably be confronted with. 

You've got this!