Start with Why – but How?

Most people who are in Enterprise Social and Digital Workplace space are familiar with the TED talk by Simon Sinek – “Start with Why” – and if not, they have probably heard about it. Heck, I think that most people working with any kind of transformation will have come across this one way or the other. There’s also a book, but I’d skip that. Stick with the video and you’re good. Trust me on that.

While being in the process of ironing out details for a new job (more on that in a later post) I had the privelege to attend no less than two events last week and it was interesting to see both the difference in audience and the difference in messages.

The first event I attended was IntraTeam Event. Frequent readers of the blog will know that I’ve been a regular at this event for many years. I will not go into details on that part, but let’s just suffice to say that it feels a little like a family reunion and I always leave full of energy and inspiration.

IntraTeam Event attracts a diverse and quite international crowd and everyone has a shared interest that lies somewhere between Communication, Employee Engagement and Knowledge Management. Interestingly, very few people care deeply about the underlying technology. Most have a high proficiency in this, but it is more like a necessary evil. The interest is really about helping people achieve more by building useful solutions. You do this by focusing on the people who you are serving and questioning the existing – by asking “Why?”.

The second event was the Microsoft Cloud Roadshow in Copenhagen. 2800 participants over two days – more than 10 times the number of people that attended Intrateam Event. Clearly this was about technology. It was about showing IT people what they could do with the things they had bought (or were thinking of buying). Most sessions started with a quick song and dance and some marketing slides and then proceeded to what everyone was there for: The Demo! Show me, don’t tell me! Don’t get me wrong, I understand the power, and I love a good demo as much as the next guy. This was about “The How”.

I thought about this on the way home and it once again confirmed how important it is that these two worlds meet on the right terms. I could argue that there is an imbalance in the fact that the Cloud Roadshow is a factor 10 larger than IntraTeam Event, but that would not be fair. I could argue that more people should focus on the quality of solutions and that would be more fair but in all honesty the main thing I brought with me was the importance of making the “How?” and the “Why?” meet on equal terms. Usually this starts with having all the right stakeholders involved in the process.

The one thing I have had against Mr. Sinek’s “Start with why” is that I believe that every “Why” is preceeded by a “How?”. How do we solve a given problem? In the HBR article “The Secret Phrase Top Innovators Use”, the words “How might we…” are highlighted as the differentiator as it signals that you may or may not succeed:

…as soon as you start using words like can and should, you’re implying judgment: “Can we really do it? And should we?” By substituting the word might, he says, “you’re able to defer judgment, which helps people to create options more freely, and opens up more possibilities.

You don’t start with “why” – it is always “how”. Does this mean that you shouldn’t ask the “Why?” question? Far from it. In my humble opinion It is just as important to ask why you want a change as it is to figure out how and to bring the right people together. After all, Innovation rarely happens in a vacuum.

Starting with “How” or “Why” – It doesn’t really matter, but asking one without asking the other is absolutely pointless.


Thank you – and kudos – to both IntraTeam, and Kurt in particular, as well as Microsoft for two interesting and inspiring days.


2 thoughts on “Start with Why – but How?

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