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The First 5 Questions Business Transformators Need To Ask

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The first 5 questions Business Transformators need to ask

If you want to transform your business or help your clients transform theirs and want to do it quicker, with less resistance, then this is for you.

The biggest problem Business Transformators have today with helping Clients with their Business Transformation isn’t what are the answers you need to have, to your Clients questions – of how are you going to help them. It’s actually – ‘what are to questions you need to ask your client?’

You see I use the term “Business Transformator”, there is a reason for this, two in fact:

The biggest problem Business Transformators have today with helping Clients with their Business Transformation isn't - 'what are the answers you need to have to your Clients questions?', it’s - ‘what are the questions to ask?'

  • First – Business Architect have a bad name, I wrote this is a previous post. They are accused of hiding away in their ivory towers, isolated away from the Business – the very same people that they are there to help, they come up with their ‘designs’ only (nothing to do with implementation, pretty pictures only), they are written in a language and level of detail that only they understand – think “French speaker, meets English speaker”. Sounds pretty, but don’t ask them to recite it back to you straight away, they might get it after one or two attempts but the moment you turn away, they are back to speaking English). This is what happens when “Business Architects” lug their ‘designs’ over the fence to the Business, the Business will agree to it in the room (the board room, where they are presented), then the moment they walk out the room, completely ignore them, the ‘transformation’ they were there to assist goes nowhere, the Transformation is deemed a failure),and
  • Second – Business Transformators have moved on passed just ‘design’ only, and include part-strategist, part-designer, part-collaborator and part-negotiator, and provides oversight of implementation, stakeholder management, coordination and negotiation.

Business Transformators know they don’t have the answers, they don’t need too. They have the questions (they also have the structure and framework to work with the Business to help draw out the answers to those questions), the key questions – Why, Who, What, Where, How and When?

1. WHY?

WHY? is the first question you need to ask. Why are you doing this? This is the Vision (the little secret in Business Transformation is there are actually two WHYs – this why here, the ‘strategic’ why? this is what does the Organisation want to achieve, we call that the BIG Why, and then there is the LITTLE WHY – the Operational Why? – these are the Business Benefits that the Organisation wants to realise from the transformation, as a result of implementing the changes delivered by the transformation project.

2. WHO?

The next question is WHO? Who is involved? These are the people, the key people, called Key Stakeholders, they are “key” because they are ‘key’ to the success of the project. You not only want to identify and agree who these people are, but also their role in the project, specifically, their role in the decision making process, in the risk management process, how risks are managed, and decisions around scope, because if you’re not careful, you will be paying ‘service’ to wrong stakeholders.

3. WHAT?

The next question is WHAT? What are the problems and opportunities you are trying to solve and take advantage of? This is effectively understanding and baselining the organisation today, the Current Operating Model. This is one of the biggest problem areas in business transformation today – our good Technology friends run around telling everyone to chase the ‘shiny new objective’, that the ‘sky is falling’, the ‘platform is burning’ – we must get off it now (referring to the current ‘legacy’ systems that the Business is currently operating on, which has been under threat for years, sometimes decades, that is held together with patch work after patch work, it isn’t actually going to fall apart at the seams (pardon the pun), it’s just a marketing technique used by Change Management that Technology Stakeholders took out of context, and repurposed it to get the Business, to agree to adopting some new technology that is “more hype” than substance, but it did sound good at the time, when it was announced for the first time in the world, ever, last week.


This is WHERE and HOW the Organisation needs to change from its current state (the As-Is) / Current Operating Model to where it wants to be in the future, the (To-Be) Target Operating Model (TOM). This is the fun stuff that Technology live for – playing with their new toys and making stuff. Business Operations like this too but they seem to be more pragmatic, mostly because they are the ones that live with anything that Technology develop.

They are the ones that have the most to lose (and gain). Like the ‘Chicken and the Pig Restaurant’ fable in project management – The Chicken wants to start a restaurant together with the Pig, and call it “Ham and Eggs”. The Pig doesn’t think it’s a good idea, because in his words “I would be committed, you would just be involved”. This is the relationship with Business and Technology. Technology will build it and throw it over the fence to the Business to use, and leave. Meanwhile the Business is left ‘holding the ham’ (so to speak). Hence the resistance from the Business?!


The last question is WHEN? When do you want (or when will) the changes be implemented, and most importantly, when will those little WHY – Business Benefits be realised?

Those are the first 5 questions you need to ask.

The key to those questions, is two things:

  • First – there is an order, an intentional order, as each question builds on the last, and
  • Second – you ask one question at a time, and only one question.

Clients may have been living the pain of their inefficient processes, customer complaints and/or losing business and want to have their problems solved before you walked in there, but trying to answer two questions at once, or any question out of order, is fraught with problems. 

These questions are actually also known as the 5W1H questions – the 5 strategic questions you need to ask to implement your or your clients Business Transformation.

When I developed HOBA®, I intentionally aligned HOBA® and the 6-Step Design Process that implements HOBA® to the 5W1H question for this reason, because this is how the Client sees their world, and this is the order they ask questions – in the order of what is important to them. That’s THEM, not You, and not Technology either (Key point – Technology and sometimes senior Execs want to start at the “HOW and WHEN” questions. This is pointless. Unless you understand WHY, WHO, and WHERE first, you dont know ‘why?’, you dont ‘who’ for?, and you dont know what the problems exactly your solution is there to solve!).

You will notice how each question (and answer to that question) builds on the previous one, while in terms of the Business Architecture and answering each of the 5W1H questions, you also are defining specific aspects of the Organisations Business Architecture, capturing the different conversations you will have with your client in their respective reference models, building blocks, and blueprints, all managed in an agile fashion, getting the different and various blueprints out to the Business iteratively, and updating them iteratively, because here’s the thing:

As you share more and more of the Business Architecture as it develops through the Business Transformation journey you are taking your client through, they will change what they think is important to them, and also the priority, and therefore change their mind. Instead of thinking “the client won’t change their mind” (they will!), you should expect they will, and have the ability to change built into your process.

If you want to learn more about the 6-Step Agile Business Transformation framework already used by thousands across the world to transform their business, including the UK Government, FTSE 100 Companies and startups, check out here.

If you want to read why others are calling The Business Transformation Playbook, the “Business Transformation Bible” read the reviews on Amazon here or see its listing on The Business Strategy eBook List of All Time, click here.

Hope you find that useful. If you did, let me know in the comments below what you like and would like to see next and share this with anyone you think would benefit from it!


Heath Gascoigne

P.S. If you want to join our Business Transformator community of like-minded Business Transformators, join the community on the Business Transformator Facebook Group here.

P.P.S. If you want to learn more about business transformation, check out The Business Transformation Playbook here.

For more information, visit https://www.hoba.tech.

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Heath Gascoigne

Heath Gascoigne

Hi, I'm Heath, the founder of HOBA TECH and host of The Business Transformation Podcast. I help Business Transformation Consultants, Business Designers and Business Architects transform their and their clients' business and join the 30% club that succeed. Join me on this journey.

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