Planning and Reflection: Two Sides of the Same Coin

Last week, I wrote about my end-of-year Journey Mapping ritual on the Faster Than 20 blog. Yesterday, I saw this kind tweet from David Daly about my post:

I don’t know David, but his tweet made me want to know more about his yearly reflection process. Fortunately, he documented it on his blog. It’s smart and well worth reading. A few things jumped out at me:

  • His reflection starts with a review of his previous year’s goals
  • In addition to his yearly review, he does daily, weekly, and monthly reviews, and he takes notes for all of them
  • His planning naturally follows from his reflection

Even though he’s allocating a significant amount of time for end-of-year reflection and planning, his whole process is both integrated and iterative. As he explains:

There are a few interesting side-effects of the review process. First, they let me see the big picture across timespan we don’t normally have the time to think about. Big change takes time and we are often focused on very small time spans. The second side-effect is it let’s me see my accomplishments more clearly. I had a very good 2019, accomplishing a lot of my goals and pushing many things forward. It’s nice to pause to see the forest for the trees periodically. It also makes it easier to keep pressing forward on the hard things when I can see that I’ve made progress on them or similar hard things in the past.

His process nicely reiterates some things that I constantly find myself harping on.

First, planning and review / reflection are two sides of the same coin. Trying to do one without the other doesn’t work.

Second, long-term complements short-term reflection and planning, and vice-versa. There’s a school of thought that wants to claim that you shouldn’t plan long-term because the world is too dynamic and uncertain, as if everyday learning somehow conflicts with long-term goals, which is a fallacy. As David writes, when you do both, it helps you see both the forest and the trees.

Norms, Strategy, and Thanksgiving Duck Revisited

It’s been nine years since I and my family started eating duck for Thanksgiving. I have also happily introduced several friends to the concept, although surprisingly, I know of no permanent converts. Some (many?) of my friends actually like turkey. But I think the biggest factor is that culture, norms, and traditions are remarkably powerful.

I get it. My family ate turkey for over thirty years before converting. When I consider how much more I enjoy Thanksgiving now, and how much less stressful it is to prepare the meal, I marvel at how long it took us to make the switch.

I see individuals and groups struggle with this all the time. Goal-setting and strategy are more often an exercise in documenting what you’re already doing rather than a deep examination of where you’re trying to go and why. The latter requires that you make a choice, and making choices is hard.

That’s not to say that doing things because that’s why you’ve always done them is a bad thing. The most important thing is that you’re being intentional, and that you know why you’re being intentional. Chesterton’s Fence definitely applies.

A Quick Note on Probability and Strategy

As folks continue to monitor the presidential elections, I think it’s worth revisiting an important truth about probability and strategy.

If someone is given a 90 percent chance of winning something, that means if you replay the same scenario 100 times, that person wins on average 90 times.

Ninety is not 100. When you only get to play that scenario once, and the person favored to win 90 percent of the time loses, that doesn’t necessarily mean that the probabilities were wrong, and it doesn’t necessarily mean that the strategies that resulted in a loss were wrong either. They all could have been wrong, but it requires much deeper analysis to evaluate that.

If there’s a silver lining to the last two presidential elections, it’s that we’re collectively learning this in a very visceral way. The better we understand this, the better we’re able to make strategic decisions and prepare ourselves for different outcomes. It’s not just true in presidential elections, it’s true in business, and it’s true in life.

Professional poker players understand this. (I highly recommend Maria Konnikova’s The Biggest Bluff for more on what we could learn from professional poker players on strategy and decision-making.) Bill Belichik understands this. Nate Silver and the good folks at Five Thirty Eight are constantly trying to explain this to the rest of us. It’s very human not to understand this, but it’s helpful to keep trying.

Reflecting on Some Incomplete Scenario Thinking from 2011

In August 2011, Kristin Cobble, Rebecca Petzel, and I had a planning meeting for Groupaya, the consulting firm we would start several months later. As part of that, Rebecca led us through some initial scenario thinking, which consisted of brainstorming certainties (trends we thought were almost certainly going to happen by 2016) and uncertainties (trends we thought were possibilities).

Here were the initial lists we brainstormed:

CertaintiesUncertainties
  • Economy really crappy in 2015
  • Mobile dominance
  • Africa will be online
  • Design firms flooding into the business (good design the price of entry)
  • Communication and Advertising Firms coming into the business
  • There’s a backlash against “collaboration”?
  • There’s a backlash against “social”?
  • Earthquake in San Francisco
  • Skilled, cheaper consultants coming here from developing countries
  • Knowledge work in the US in the decline
  • Knowledge work undervalued in the US
  • Net Neutrality
  • Trust in Internet services? Things like Wikipedia, AirBnB, eBay rely on trust
  • Institutional clamp down or continued democratization
  • Middle East political situation
  • U.S. “Arab Spring” coming?
  • Backlash against rationalism; rise of fundamentalism
  • Large factory consulting firms hijacking our business

Our “Certainties” list wasn’t very good. The economy was not “crappy” by conventional metrics in 2015, although we were continuing to feel the impacts of widening inequality. And we didn’t really see communications firms come into the business.

Our “Uncertainties” list was far more interesting. We no longer have net neutrality, at least at the federal level. Trust in several social media (Facebook and Twitter in particular) is down, and deservedly so. And reading the bullet point, “Backlash against rationalism; rise of fundamentalism,” now makes me want to cry.

I review these notes every few years out of curiosity and sentimentality, and I pulled them up again last month as COVID-19 was wreaking havoc on our lives. A few things come up for me when I look at these:

  • It’s possible to have an interesting scenarios conversation without a lot of prep. We were clearly already connected to a lot of interesting people and perspectives, which was how stuff like “backlash against rationalism” made it onto our list. (Kristin contributed that one based on conversations she had had with her friend and former colleague at Global Business Network, Eamonn Kelly.)
  • Prep would have helped broaden our perspectives and address some blind spots.
  • Pandemic wasn’t on the list of uncertainties.

The biggest thing that comes up for me is that we never truly benefited from the power of scenario thinking, because we treated it as a one-off. Imagine if we had returned to this list once a year, even without any additional prep, and talked through the possibilities. What might have come up? How might this have changed our thinking? What might we have done differently as a result?

This is a regret I often have about my own past work, and it’s something I find with consulting work in general: We barely benefit from the work (which is often time- and resource-intensive), because we never revisit it. There are lots of reasons we never revisit it, but the most common one is that we’re going too fast. I’ve been able to correct this with my own work (although it took several years and lots of focus and failure), and I continue to try to help others do the same. It’s been really, really hard, which is sad, because it’s so beneficial.

Baselines and Narratives

I haven’t read Jonathan Allen and Amie Parnes’s Shattered about Hillary Clinton’s failed presidential campaign, but I have found the reviews and their virality fascinating. Here’s what the New York Times, National Review, and Rolling Stone had to say. The Amazon.com reviews are mediocre at best.

There is something lurid and compelling about reading a retrospective about a failed campaign. It’s like looking at a train wreck — it’s hard to tear your eyes away, even if you want to. Unlike a train wreck, however, it’s hard to assess how “bad” Clinton’s campaign actually was, and what I’m reading about the book doesn’t seem to help.

In my experience working with organizations and their leaders, including some very good ones, there is a baseline of dysfunction that would surprise most people. Internal effectiveness and good strategy matter (which is what keeps me employed), but they’re not the only factors that contribute to success. You have to be very careful about attribution bias, especially when dealing with complex, systemic challenges.

So far, most of the retrospectives and commentary I’ve read have reeked of attribution bias.

The one thing that stuck out for me in reading the reviews were the points about Clinton’s lack of a clear narrative. The National Review, for example, wrote:

In Shattered, we learn that ten speechwriters, consultants, and aides had a hand in writing Clinton’s announcement speech, which unsurprisingly turned out to be a long, muddled mess. Obama speechwriter Jon Favreau, briefly brought in to help, concluded that the speech (and by extension, the whole campaign) “lacked a central rationale for why Hillary was running for president, and sounded enough like standard Democratic pablum that, with the exception of the biographical details, could have been delivered by anyone within the party.”

Again, I see this all the time working with leaders. It’s hard to identify a clear and compelling narrative and to stay on message, but it’s important. In their book, Made to Stick, Chip and Dan Heath attribute this challenge to the Curse of Knowledge. Effective leaders have lots of knowledge, but that knowledge can get in the way of telling a clear story.