….and I’m being generous when I use the term ‘good’, which for the sake if this post is meant to signify advice given with good intent but has turned out to be not entirely useful. Trying to maintain a constructive (versus critical) vibe.

We’ve all been there, both personally and professionally. We get both solicited and unsolicited (!!) opinions on the regular from friends and family relative to our personal problems and/or at major decision points. In the business world we experience the same phenomenon; and, for the sake of focus, I’m going to in this piece tend to isolate the more one-way direction that comes to us through our broader ‘feed’: blogs, panels, social media, presentations and other forums we experience in not only live settings but in print and recorded video. The entrepreneur space is especially full of opinion, in part because of the sheer growth of this universe and in part because startup culture is one of sharing and giving back. Consequently, advice and information circulates both intensely and consistently.

So now I’m going to ask you to reflect on the body of advice that you have received from all of these sources over the last several months to a year. No doubt, you’ll note some that you have valued and incorporated into your work and life. But, I’m most curious to know to what extent you have heard/seen/read/received ‘good’ opinion or direction that has left you simultaneously inspired and directionless as a result.

I’m not talking about Facebook memes of inspirational quotes. They come to us from people who don’t necessarily live their words and they are read by people who are not in their hearts prepared to make life changes. X them out. Let’s look at the business side, where I’ll cite TED talks, startup founder presentations, blog posts with 30 breakthrough ways to generate leads or engage your consumers. That stuff. If you think carefully, you’ll start to mentally catalogue the number of times you’ve been impressed by what you took in but you’ll then realize that the bulk of this content inspired no concrete action on your side.

The reason for this lies in one word that forms a key question:


That word is the missing piece. It unlocks the magic of what makes good/OK/passable/crappy advice truly great. Or, at the very least, advice the audience can actually use.

The question of ‘why’ has a number of elements.

Here’s the first and biggest one which I’ll share via a little story that more poignantly originates from my personal life.

Know your audience…because it’s truly just about them.

One of my closest friends recently had something life-changing happen to her. She got a pile of money dropped on her, completely out of the blue. Not enough to retire on by any stretch but definitely a game-changing amount. I’ll leave it at that for the sake of privacy. Stop for a minute and ponder how this would impact your life had this happened to you.  When you complete that thought process, read on.

So she called me to discuss what happened. All I got was the facts and not even how she felt about it but it was clear there were decisions at hand as a result. My counsel to her was this: “I know your first instinct is to get rid of it. Don’t. Don’t do anything. Don’t spend it, put it somewhere safe in a low risk investment for a minimum of six months and every night, meditate for at least 30 minutes to gain clarity on why this happened to you.”

‘Whaaaaaaa?’ is mostly likely what you’re thinking, am I right?

In your mind you’re thinking trips, pay off mortgage, maybe something charitable, nights out, fun, events, etc etc

So the question is: why did I give her that advice….?

The answer is because I know her. Well. And to give great advice you have to know your audience.

See, my friend is a Buddhist. Not Buddhist-of-the-month like some people who go to a few meetings, read a book and wear a wrist band. I’m talking quarterly retreats and I would say at least 30 years of never. having. skipped. a. night. of. practice or meditation. Ever. Like…ever. She’s a former stock broker and current healer, in the medical field. Not a robe wearing hippie as some would expect, but instead a regular (and awesome!) person with a clear moral compass and a deeply ingrained set of values.

A Buddhist isn’t attached to money or material things that can be here today, gone tomorrow. Money means little. Money is but a tool to inject positivity into the world, while too much of it can breed thoughts or behaviors and are counter-productive to this pursuit. So, to a real Buddhist, a stack of 10s and 20s isn’t universally a good thing.

So the first part of my advice was to reinforce the credibility I have with her. Made that connection by stepping into her mind and guessing correctly what she’s thinking, that she wanted to just give it away so as not to be overwhelmed by the meaning, implication or intent of this windfall. I knew that she wouldn’t make the right decision for her unless she processed this event in the way she makes most of her decisions.

When you tell people what you would do, you’re only being truly helpful if your audience thinks and processes the same way, and has the same priorities and values. It’s actually fairly rare that all this synchs up perfectly, even with best friends or siblings. Keep in mind, then, what you would do is little more than context for your advice, if anything. Your final advice should always be framed in how your audience sees the world, or your words will fall on deaf ears, if they don’t irritate them.

What’s freaky is that I was the only person to give her that advice. No one, not even her sisters, went there. She recently told me that now, a year later, this was indeed the perfect advice.

This is why I rarely share my problems with anyone. First, I have tools to sort myself out on my own, so I’m lucky. Second, I usually feel worse after people dispense their advice because they reveal through the process how little they truly understand me, even though they care. So, I just don’t. I’m running my race, not yours, but thanks anyway.

In the business world, I similarly preach a strong customer orientation. I belabor the point in my post on why digital founders fail hard. Not only can they fail to embed themselves in the consumer, but they can fall in love with their product at the expense of the consumer. Your customer’s needs and problems are the context for everything, and if you don’t design a product that helps them meet those needs in the way they would prefer to approach it, you could be sunk. Customer first, product second.

‘Why?’ also means ‘under what conditions?’

And now we move more deeply into our business experiences for a variation of ‘why’. I’ll begin by giving an example from my corporate life and then follow with some situations in the startup world.

I have hired a number of agencies and business partners over the years in my corporate gigs. Among my more recent activity involves the RFP I created to hire a PR firm to handle media relations and event marketing for the Canadian gaming business when I was a Director at Warner Bros.

As we filtered through to the final two candidates, I requested an in-person pitch on a business case I created for our superhero-themed gaming line. I outlined the product, the objective and all details, and asked for a 15-20 min pitch on the go-t0-market plan. I typically give criteria on how the pitch would be evaluated but this time decided to leave it open ended.

Company A came in and presented about 8 distinct tactics of how they would take this to market. All kinds of interesting ideas, and quite a fun and spirited presentation. Let’s cast aside for a moment that two of the ideas took illegal license with a trademark which was a massive flag for me. My one question to them was this: ‘if we only had the money to do 3 of these ideas, which would you do and why?’ I completely stumped them and before me began an internal debate, which yielded no clear answer.

Moving on to company B. They waltzed in and took a different approach. They talked about how they interpreted the opportunity. They shared what they know and believed about the consumer, the competition and environmental factors. They relayed their experiences of what they learned from similar executions in terms of what works and then explained how this campaign was similar or different. In short, they concisely told me why they would be recommending what they were before they even revealed their ideas. They won before I even heard their ideas.

When I coach my teams on presenting, I remind them that the setup is arguably more important than the content. If you get heads nodding by how you connect to your audience and its business to the marketplace – how you see the opportunity — you will similarly be most of the way to #winning. For the magic is in the ‘why’; it separates trial and error from disciplined, strategic thinking; it separates business sense from luck.

founder presentationI have since transported my soap box to the entrepreneurial domain where my ambitions are both professional and charitable. Unless you have the beautiful mind of only a select number of entrepreneurs you will need much help on your path. And the help comes not only in the form of information and ideas, but a framework to understand which of these are right for you.

Ever read articles such as this one with 63 lead generation strategies and get that inspired-but-confused feeling I talked about earlier? The problem is that you now feel armed with tools but have no idea under what conditions to use them or prioritize them. Excited yet immobile. That’s what’s largely missing from advice that takes the form of tips and tricks….or the stories of “I threw together some code, and yadda yadda yadda check out my private jet”.

I no longer attend that many panels or founder presentations for the primary sake of learning. I do learn, but not nearly as much as I usually hope to, which makes for poor ROI on my time to schlep over there. I do it mostly for networking. There is a lot of advice out there that sounds great on the surface but can actually be destructive to your company if incorporated so I find myself either disagreeing or raising flags. A lot. Instead, I take in these presentations more as heartwarming stories than I do wholesale advice. Makes for a consistently-positive experience.

Take Wealthsimple for example. Great idea. Great company. Awesome founder. Successful. If you click to my article on the Dark Side of MVP you’ll find more discussion and a link to a 10 minute presentation on how the company started.

(Note: this is not all about criticizing anything to do with Wealthsimple and more about making a point, by the way. They do God’s work)

At that moment in the company’s lifecycle, Katchen was publicly advocating the MVP approach because it worked for him. The problem is that it worked for Wealthsimple because the conditions were right. New category. High barriers to entry, mostly due to regulation. There was lots of time to figure this out. You had to recruit competencies that aren’t widely available. You could launch MVP and incubate over time because you were breaking new ground. Consumers would stick with you and be patient as you stumbled along because they had nowhere else to go to service this specialized need.

My point is, your story won’t work for everyone, a point my article reinforces with rationale. Maybe most know this already, but not all do. I’m sure a number of entrepreneurs in the audience went back to their team and said “Hey! We can launch our idea as a spreadsheet we create in 3 hours because it worked for Mike and look at his company!” That’s not a compelling ‘why’, if you ask me. And this is why founders are prone to taking the wrong steps….or taking no steps because they hear several different opinions on an issue which they can’t reconcile. I’m seeing this quite a bit, and I’m helping to fix it…by bringing ‘why’ to the table.

That’s my lot in life because that’s just me. I’m a ‘why’ guy, much more than a ‘what’. It’s also why I don’t worry about creative problem solving or purposely think outside of the box. I don’t recognize a box, because if your ‘why’ is solid, the ‘what’ could be quite the boring answer, yet no less effective. Results tend to be my first priority.


When I was at the manager level, I had an awesome director named Marisa. I am so lucky to have shared workspace with so many of brilliant and passionate people of which she is certainly one. She had a five year old (at the time) named Matthew, or Matthew J. Precocious kid, based on the stories she told. One day we were talking shop in her office and she started to laugh and said to me “you remind me of Matthew J. Everything I say he answers with ‘why, Mommy?’ Can’t get him to do a damn thing without answering that question”. *Shrug* Yep, I’m inarguably an overgrown five year old, a badge I wear with honor. I could only hope for such clear vision and unfiltered authenticity.

The answer to ‘why?’ in my firm belief is the reason we move forward, close the deal, or even evolve. Our approach to the word establishes credibility, builds our confidence and demonstrates not only our insight but our wisdom. It calms us down when complexity makes us anxious or when our temperatures rise with the decisions before us. It stops us from rolling our eyes when our well-meaning friends and family butt into our lives to pontificate.

‘Why’ is a powerful little question when used in constructive ways and with positive intent. It has caused me to look outward as much as I look inward. It has made me someone people turn to for advice, which has in turn strengthened my relationships and advanced my career to a place I can be proud of. And Matthew J? If you ask me, that kid, too, is gonna be all right.



Start with Why. From a business/marketing perspective this is 100pct true. You unlock everything once you understand why you do what you do and make the decisions you make. Lots of truth in this classic video from Sinek, although I, like Forbes, think he’s full of hot air most of the time.