Outcome, Strategy, Projects

Adopting the hierarchy of Outcome -> Strategy -> Projects (thanks to some well-timed coaching :-)) has been a recent revelation of sorts in driving better thinking, higher quality communication, and, thus, more productive conversations.

Conversations that derail or go nowhere are almost always conversations about projects. And, these conversations are transformed when we move up the hierarchy to talking about outcomes and strategy instead.

It also turns out that working through outcomes and strategy before getting to projects helps create the kind of focus that leads to the right projects being discussed and prioritized.

Win-win-win.

Bad prioritization, Good prioritization

Bad prioritization: Make an ordered laundry list and intend to make some progress on everything. Easy. Ineffective.

Good prioritization: Use judgment to pick the top 1-3 items we’re going to focus heavily on – an outcome of sound strategy. Agonize over saying no to perfectly good ideas that just aren’t making the cut at this time. Tough. Powerful.

Applies just as well to building good products, planning how to spend time on a holiday, and building a better quality life.

Strategy and trade-offs

Good strategy involves making explicit choices that are backed by a clear articulation of the trade-offs that accompany those choices.

Articulating strategy well isn’t about listing everything required to be done to win. That part comes easy.

The challenge with crafting good strategy lies in picking the path to winning with the limited resources (and they are always limited) at hand. More often than not, that path involves investing heavily in your own strengths while doing just enough so the weaknesses don’t get in your way.

There are obvious trade-offs with that (or any) approach. But, again, if there aren’t clear trade-offs, it isn’t strategy.

Acceptable error

Our Table Tennis coach used to have a rule when we were learning how to hit a top spin forehand – hit the ball out if you must but don’t let the ball hit the net.

Hitting the net, in his mind, was a result of a weak attempt. He knew we’d make plenty of mistakes on our journey to learn how to hit the top spin right. And, he made it clear that he’d rather have us try an expansive stroke and fail – that was an acceptable error.

It turns out that the acceptable error concept is a useful tool in helping us accelerate our learning, execute better, and be kinder to ourselves. Imagine you are running an important project for the next three months. There is no way you’ll walk out of the experience knowing you’ve done a perfect job. There is no perfect job. You’ll always have some constructive feedback.

What would you rather the feedback be? For example, would you rather the feedback be about your propensity to go fast? Or, would it be about your desire to ship with the small details taken care of?

If you decide that erring on the side of speed is an acceptable error, for example, it’ll do two things.

First, it’ll bring a lot of clarity in your day-to-day execution. When push comes to shove, you’ll know to prioritize speed and you’ll walk away with lessons from consistently doing so.

Second, once the project is over, you’ll also know to expect feedback about your focus on speed. When you know to expect it, it won’t sting as much.

Acceptable error, as I’ve come to appreciate, is just another way of expressing strategy. Every strategy has its downsides. But, if chosen well, it’ll help us build on our strengths, learn, and provide clarity as we execute.

Said clarity is worth a lot.

Spending time with the why and the how

As you can tell, we’re in the midst of a series of end of year tradition posts. Today’s tradition is one that accompanies the annual review – spending time with my why and how.

This exercise involves revisiting how I define my why/purpose/mission, how that translates into my values, my culture, my approach/strategy, and the 3 most important principles I live my life by.

I have two reflections from this iteration. First, while most of it is consistent to the first version from 5 years ago, every tweak reminds me of the fact that this is a “living document” that I need to re-commit to.

The second reflection is a reminder of the power of deliberate iteration. Each iteration pushes me to articulate this better by making it flow more logically and simply. And, the more logical and simple it is, the more easier it is to live by.

v2018 is now below and on the “About” page.


My personal mission/“why”/“purpose”/what I care about: Build active relationships with framily (close friends and family), learn, and contribute positively to the world.

Thus, my simplified 3 word version articulation of what I value is – people, learning, contribution

My culture or the norms with which I make decisions flows from what I value. I aspire to show up every day by being thoughtful about how my actions impact the people around me, learning focused, and hungry to contribute. Again, in 3 words that would be – thoughtful, learning focused, hungry.

I approach my days by aiming to do my best in my 4 roles – I think of this as my strategy or my “how.” :-) These roles are sorted in priority order:
1. Leader of self
2. A caring member of my framily
3. A learning focused teammate
4. A responsible contributor to my community, i.e., the world

3 principles that I attempt to live my life by are:
1. Integrity: Integrity is making and keep commitments. This means walking what I talk and talking what I walk.

2. Love/Growth: Love is the will to extend oneself for one’s own or another’s spiritual/mental growth. This means committing to to doing small things with extraordinary love and investing in continuous growth.

3. Half-scientist, half student: I aspire to live my life as a mix of scientist and student. This means engaging with life to consciously take the time to define problems, build hypotheses, experiment, and then learn. Life, after all, is simply a series of experiments and learning opportunities. 

You and future you

For the longest time, you didn’t have too much of a say in crafting the “future you.”

Even two decades ago, those who worked “above” you in your organization had a big say in what opportunities you got to work on. Want to make that big career switch? Or, want in on that exciting new project? You just had to wait to get picked by the powers that be.

But, that’s changed.

Now, you have access to an incredible set of media tools to shape “future you.” You could demonstrate your penchant for coming up with ground breaking insights about the industry you want to work in on your blog or on LinkedIn. Facebook or Instagram can be incredible platforms to show off your artistic abilities. And, Twitter is a great place to build a following around your comedic wit or knack for pithy dialogue.

Like all good things in life, these tools are entirely what you make of them. You can use them to consume an endless stream of sticky content. Or not. If you decide to do so, these tools can be your customized digital garage to work on projects that would open up opportunities for “future you.”

Here are 3 simple questions to help craft your approach toward social media –
1. What sort of projects would you like to work on in the future?
2. What do you need to learn and ship to get access to those opportunities?
3. Which 1-2 social media tools could you use to build that body of work? If you really love the consumption, pick one other tool to consume (guilty pleasure allowance) and nix the rest.

You could choose to unconsciously engage in social media in ways that simply benefit their parent companies and hurt you.

Or, you can harness the tremendous power these bring and pick yourself to do work that matters.

5 strategy questions

Strategy can be a nebulous concept. How do you define a good strategy? Do you know one when you see one?

A wiser friend shared 5 questions from a book by former P&G CEO A G Lafley and Roger Martin – “Playing to Win.”

• What is our winning aspiration?
• Where will we play?
• How will we win?
• What capabilities must we have in place to win?
• What management systems are required to support our choices?

I love frameworks that boil complex things down to simple idea. And, if I were to simplify further, the core questions are “where will we play” and “how will we win.”

For the next time you are thinking about strategy…