Convincing different personality types to invest in Digital Transformation

James Gadsby Peet
Nov 17, 2016 · 6 min read

TL;DR — how you make decisions is not necessarily the way that others do. There are lots of different preferences and the more awareness you have of them, the more likely you are to be able to persuade people to invest in Digital Transformation

Now more than ever, it is obvious that different people fundamentally see the world in different ways. For every single ‘truth’ that you hold to be self evident, there will be those who disagree with you without question. For every inclining, that you feel in your gut, there will be someone else who knows in their heart of hearts that you are wrong.

When at their best, our families, organisations and societies celebrate these differences and work together to find common ground on which we can build. At their worst, they create impasses that seem so difficult to climb that it makes you want to climb back under the duvet covers and watch cat videos.

Many of us have jobs where we are trying to change organisations. In these roles, what we are really trying to do is change people’s minds. As such, it is crucial that we have an above average sense of how others think, feel and perceive the world. Otherwise we will not know how to present our case to them in a way that makes sense, and if they don’t understand it, then the last thing in the world they’re going to do is support it.

So using Digital Transformation as your goal, here are a few thought about how to get different ‘types of people’ on board and engaged.

Disclaimer: I don’t like putting people into ‘boxes’ — so I would suggest thinking of these as possible starting points for the conversation. In my experience people tend to display attributes of different models at any one time or in any number of different circumstances. The most important lesson is to understand that the way you make decisions, is not the way that everyone makes decisions.


Taken from the Values Modes framework, this group of people are security driven and want to feel like they are in control. Risk is the worst thing in the world for them.

  • Show other ‘heritage’ organisations that they trust which are doing interesting digital work.


Again, using the Values Model Framework, these folks want to show others how successful they or their organisation is. They always want to be bigger and better and follow that pragmatist approach over a particular values / ethical set.

  • Show the growth which could be achieved once you’ve improved the effectiveness of your organisation digitally.


This group are driven by wanting to do the right thing and are willing to explore a variety of options to get there. They are not afraid of getting things wrong and are usually considered innovative and driven to be the best they can be.

  • Link the change to the organisation’s cause and what digital transformation will do for your mission.


Charismatics account for 25% of all leaders. They are easily intrigued and enthralled by new ideas, but experience has taught them to make final decisions based on balanced information, not just emotions. Richard Branson is often thought to identify with this way of thinking.

  • Boil the benefits down to their simplest form — such as an increase in efficiency or the ability to test new ideas quicker


Thinkers account for 11% of leaders and can be the toughest executives to persuade. They are impressed with arguments that are supported by data. They tend to have a strong aversion to risk and can be slow to make a decision because they want to consider and understand all perspectives. Bill Gates famously falls into this category.

  • Use data to show the growth of digital both within your organisation and outside of it.


19% of leaders fall into this category. They tend to be highly suspicious of every data point presented, especially any information that challenges their worldview. They often have an aggressive, almost combative style but this is usually not as emotionally charged as it comes across.

  • Gain credibility long before you try and get this person to sign something off. Help them or their team on a project that meets their goals and improves their measures of efficiency / quality. Something highly demonstrable like a PPC audit or email strategy can work well.


Followers account for 36% of leaders. They make decisions based on how they’ve made similar choices in the past or on how other trusted executives have made them. They tend to be seen as risk-averse.

  • If you do nothing else, illustrate how other organisations that they respect have evolved Digitally and the benefits that has brought them. Sell the story of these improvements rather than focussing on the detail, although have it to hand. Speak to people internally at these other organisations to get first hand insights.


Kind of like a combination of Skeptics and Controllers, these are often the hardest people to convince of something that they don’t already hold to be self evident. They can’t deal with uncertainty or ambiguity and anyone that comes to them with something that sniffs of being unprepared, will be given very short shrift indeed.

  • Bring in external experts to present the details of your argument.


‘Change the way you persuade’, Williams G.A. and Miller R. B. Harvard Business Review ,May 2002

William Joseph

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