The Single Most Important Question in Business

…is the one we ask least often.

As responsible business owners, we invest a lot of time answering the “what” question. What will I sell? What should my price be? What kind of marketing should I do?

We find “how” intriguing as well – How will I find clients? How will I make ends meet this month? And we’re even okay with “who” (who is my ideal client) or “where” (where do I locate, advertise, network, etc.?).

All of these questions – who, what, where and how can be just plain fun to play around with. Why? (hint – this is a pretty important question) – Because they are largely theoretical questions. I can answer ALL of them brilliantly and do absolutely nothing – frozen in my tracks but feeling as if I’ve made great progress. But we’re really just playing office again. Merely doing complex (but easy) things that make us feel important and impress others.

The 2nd most important question in business (see last week’s post) is “when”. We avoid it like the plague because when we attach it to all the other questions (who, what, where, and how), we suddenly lose control of our future. Instead of managing our plans, we are now managed by our Plan, required to take action and move forward when we’d rather sit around thinking about it and just play office some more.

But the biggest, most important question in business is avoided even more then “when”. And it’s the most important question for determining our success.


On the most strategic level, if you don’t know why you’re in business, you’re going to fold when the going gets tough. And on the most tactical level, if you don’t know why you want to buy that snazzy new printer, you’re going to wonder why you can’t make money.

The “why” question should be attached to every other question you need to answer. What should I sell (why should I sell it)? How will I find clients (why do I want those clients)? Where should I locate (why is this a great place to be?)

And most importantly, “why” even needs to be attached to “when”. When do I want to be at 100 clients (why then and not later/earlier)? When do I want to have a fully mature business (why then and not later/earlier)?

When we ask why, we have a better chance of making decisions that are all aligned with our long-term plan (asking “why” makes us get a long term plan). When we avoid asking why, we make individual decisions in individual vacuums and wonder how we ended up right where we started at the beginning of the year. The result – a business going many directions at once and ultimately going nowhere.

Why gives us clarity of purpose.

If you won’t ask why, don’t bother with the other questions. They are all mechanical questions and don’t matter outside of “why”.

Why are you in business? Why do you do business they way you do? Why do you think it will take you 20 years to grow a mature business (why not 5)? Why do my customers buy from me? Why am I stuck at the same revenue as last year?

Why don’t you ask why more often?

Seth Godin wrote a book called The Dip in which he contends we quit when we shouldn’t and don’t when we should. If we asked why more often in business, Godin, wouldn’t have had a book to write. Answering why helps wake us up to stupid habits that aren’t helping us but just make us comfy (or impressive). And more importantly, answering why we’re in business gives us the motivation to push through the dips, to move from survival, through success, to significance.

Every time you ask a who, what, where or how question, ask “when”, then ask “why”. You’ll make more money in less time. Why do you think that might be true?