Better Decisions – Advice from Anne Duke

Annie Duke seems like a surprising person to give advice about making better decisions. She’s a poker champion turned author of a bestselling book, “Thinking in Bets,”. I’ expected that her ideas are about how to take high risk bets and do them well. I recently listened to an interview of hers[1], which was refreshingly different. There was an early aha moments for me that made me go on (more shortly). Then, she said she’s now a ‘decision facilitator’ to some of the world’s top Venture capitalists. What’s a decision facilitator? And why is a poker champion advising venture capitalists about decision making.

Here are my reflections on listening to her. At the outset, there’s a practical toolkit of tactics that are both fun and actionable. Then, some sage observations on why we make poor decisions. Finally, there was a provoking idea, which make me think a lot. One of the reasons I write is to help clarify such provocations to myself. Let’s dive in.

What we are most prone to

Annie’s sage observations about what makes us poor decision makers. She says we:

  1. have overconfidence in our intuition. We place too much faith in our gut instinct
  2. are too present-focused, with intense but fleeting feelings that inhibit rationality
  3. carry illusions of unique insight. Although in reality, other people see our situation more clearly
  4. are reluctant to use de-biasing techniques. Wouldn’t that be admitting our poor judgement?

“We think a lot more highly of our intuition than we really ought to….of our ability to notice things in the moment and act rationally toward”

Annie Duke, author of “Thinking in Bets” and “How to Decide”

Over-confident, present-biased, egocentric and generally unwilling to do something about it. That’s us.
Sobering.

Adversarial collaboration

Annie speaks of an interesting story from the late legendary Daniel Kahneman’s life.

“Kahneman actively sought out strong disagreement or contradictory views, not to argue against them, but to collaborate with those adversaries in hopes of getting closer to the truth through joint empirical investigation. It was an eagerness to prove himself wrong if the evidence pointed that way.

One of Daniel’s defining works (along with Angus Deaton) is a famous study in 2010 that got a lot of press[2]. It said that money doesn’t buy happiness beyond $75,000 annual income. The idea was that once your basic needs are met and you don’t have to worry about paying rent and so on, more money doesn’t increase happiness by much.
About a decade later, Matthew Killingsworth’s found this to be not true. Money and happiness are correlated at all income levels, he found. The more money you make, the happier you tend to be. Our normally to this is trying to dismiss the other view as wrong. “But instead, it was vintage Danny – he said, ‘Alright, let’s do this together!’ He joined forces with Killingsworth and Barbara Mellers to basically try to resolve that issue through collaborative research. He was just always seeking out situations like ‘Why am I wrong?’ He was eager and excited to prove himself wrong if the evidence pointed that way.”

This is the idea of adversarial collaboration, my aha moment. It reminded me of an interview of Daniel Kahneman I’d heard on Shane Parrish’s knowledge podcast[4]. I’d read his book “Thinking Fast and Slow” laboriously. I was a bit shocked when, in the interview, he said, some of the ideas in his book “didn’t replicate”. For example the priming effect I found fascinating was found to be untrue[4]. I remember feeling a tad angry then, having to “unlearn it”. But he’d spent years discovering those. Years. Yet, he wasn’t attached to what he found (more on what they jointly found coming up).

Daniel Kahneman did have the luxury of being a researcher. He could afford to go back and spend time on something that turns out to be wrong. Some of us practitioners need to decide on the fly and then live with how things turn out. Our “adversaries” are simply too opinionated, poorly researched counter views. You can’t collaborate and resolve on most occasions. Yet, I have to admit that, on several occasions I could have practically embraced “adversarial collaboration”, but didn’t.

Two Tips for instantly better decisions

These two tactics from her tactical tool-kits are so simple, that I’m already trying them out:

  1. Mental Time Travel: “One thing I used to do with my kids when they were really upset about something, I had to impose on them. I’d say ‘this is going to be so great for you when you’re grown up. At Thanksgiving you’re going to be able to tell these stories to your children and it’s going to be the best. You should be thanking me, so you can talk about your crazy mother.’ It allowed them to get some time and space to realise ‘this is going to be funny at some point’ no matter how horrible it seems now.”
    With the benefit of hindsight, I see this working really well for us adults too.
  2. “Nevertheless”: “Let’s say my children are arguing about why something I’m imposing on them is unfair. I’d say ‘I hear you, nevertheless you’re grounded for two weeks.’ In essence, I’m saying ‘I hear what you’re saying and I understand, nevertheless this is what’s going to happen.’ The key here is to genuinely make people feel heard (which is not hard, although we rarely do it). In the workplace you can say ‘I heard you and your input. Trust me it was incorporated into the decision. Nevertheless this is the path we’re going to take.'”
    If they feel heard, people will accept it, even if they don’t like it.

Avoid decision meetings

“Too often in meetings, we try to do discovery (finding out what everyone thinks), discussion (debating those views), and decision-making all together. That’s extremely flawed.”

The only thing we should do in a meeting is discussion… No discovery, no decision-making.

Annie Duke

When people voice their opinions live in a shared space, the loudest or most confident person tends to have an outsized influence, regardless of whether they are actually right. Social pressures like that undermine sound judgment. Instead, in the discovery phase – solicit everyone’s true independent opinions and reasoning, says Annie. It’s quite easy to do in an asynchronous manner, where people can’t influence each other. For example, before a product roadmap meeting, send out a list of potential features to the team. Have everyone individually rank and rationale their priorities, without seeing others’ responses first.

Only once you’ve independently gathered this raw information should you convene to discuss the differing views and rationales out in the open. The meeting itself should focus solely on areas of disagreement. Then the final decision should be made independently. Not as a live group in the meeting. People can either vote privately on their personal leanings, or the decision-maker(s) can take the call.

The key is separating those three phases – discover, discuss, decide. This preserves true independent thought in the begin and end stages.

Driving alignment is toxic

This provoked me. Yet, I see the wisdom in it.

Says Annie, “drop the misguided pursuit of alignment coming out of meetings. It’s naive to expect everyone to agree, nor should that be the goal. It breeds coercion. Disagreement is healthy and captures the full decision landscape for leadership. If you can implement this independent model of getting raw unbiased opinions first, an open discussion in the middle, and a final decision independently, it greatly improves decision-making. It’s a game-changer I’ve seen work.”

Here’s why I feel provoked. First, this feels hard when I’m at the receiving end of this. Second, it requires exercising power, which breeds the fear (and possibility) of making enemies. If they’re not aligned, how will we execute? What will I do when I hear, ‘which is why I told you this is not the right decision’.

When I reflect on this more, we often allow our decisions to degrade to the level of alignment. If we need high quality decisions, we need to raise the bar on culture. We need to embrace taking unpopular calls. People need to truly embrace disagreeing and committing. Great decisions and need great culture.

On quitting

Stewart Butterfield shut down his startup Glitch at an unexpected juncture. Stewart was the creator of a product called Glitch, a massive multiplayer online world-building cooperative game. When Glitch launched, it received tons of great reviews and word-of-mouth praise – it was described as “Monty Python meets Dr. Seuss.” Prestigious investors like Andreessen Horowitz and Accel invested $6 million. And Glitch had 5,000 diehard users who played over 20 hours per week.

However, the customer acquisition numbers revealed a major issue. For every 1 user playing 20+ hours weekly, there were 95-99 users who just tried it briefly for 5 minutes before leaving. It was a customer acquisition nightmare. To combat this, in 2012 they committed to 6 weeks of paid marketing. During those 6 weeks, new user acquisition grew an impressive 6-8% week-over-week. But at the end of that 6 week period, on a Monday morning in November 2012, Butterfield woke up with “the dead certainty that Glitch was over.” He still had most of the investor money in the bank. He did some back-of-the-envelope modeling their growth and customer acquisition costs going forward. His calculation was that it would take 31 weeks until they broke even. But he realized that was an absurdly optimistic assumption, as their acquisition costs would inevitably rise once they saturated the core gaming market.

Butterfield realised Glitch was not going to be a venture-scale business model. And even though his team didn’t yet see it, he decided he needed to shut it down. Not just because it was a financial drain, but because it wasn’t fair to keep stringing along employees who had taken equity, when that equity likely had no future value.

So against all conventions, he sent an email to his investors and co-founders admitting defeat and declaring his intention to shut down Glitch and return the remaining money. Who actually does that? But he knew it was the right call, though he admits he probably should have made that call even before running the paid marketing push.

Now for the most interesting postcript. Two days later, Butterfield realised the internal communication tool his team had been using and loved could actually be a product itself. He pitched that idea to his investors, who rolled their Glitch investment into this new communication platform – which would eventually be named Slack.

The key learning, says Annie, is “we get so focused on ‘but what about everything that I’ve put into it’. Sunk cost fallacy. What we forget is there’s also the cost of not pursuing other opportunities that might be available to you,” she said.

“And as smart as Stuart Butterfield is, he couldn’t see Slack until he quit Glitch. And that is a true cost that he would have borne of continuing with Glitch … Slack would not be something that we’re all using today.”

How to quit objectively?

Her simple adivce – set up a “kill criteria” in advance. Kill criteria are specific scenarios or trigger events which signals that it’s time to pivot, cancel, or kill the initiative. You pre-commit to the action if they occur. This is, says Annie, the antidote to our irrational persistence bias.

“For example, when working with a sales team, I had them do a premortem exercise imagining they spent 6 months pursuing a lead through an RFP process, only for the deal to fall through in the end. I asked them to identify warning signals they wish they had heeded early on that foreshadowed the failed outcome. Some kill criteria they identified included:
1) If the RFP seemed tailored for a competitor
2) If the customer refused to do a demo and only wanted to discuss pricing, and
3) If they couldn’t get an actual decision-maker in the meeting room after initial conversations.

For each of those flags, they pre-committed to a specific action. For the pricing-only request, the kill criteria was to walk away immediately without pursuing further. For the competitor-tailored RFP, they’d directly ask about the competitor’s involvement and how advanced they were, then killing the deal or proceeding based on the response. For lack of decision-makers, they’d offer to elevate to an executive meeting and kill the deal if the customer declined.

“That’s actually the best use of a pre-mortem – to create kill criteria. It’s an upfront exercise to combat our human tendencies toward irrational persistence once we’re emotionally invested in an initiative.”

I’m now tempted to pick up Annie’s next book. “How to Decide”, although I’ve already read quite some literature on this.

Sources and more interesting notes

  1. Interview link
  2. High income improves evaluation of life but not emotional well-being
  3. Kahneman resolves conflict on income-wellbeing study
  4. Don’t read the book “Thinking fast & Slow”
  5. Disclosure, I’ve lightly edited her quotes for brevity
  6. Illusion of unique insight:
    “We tend to think that we have insight that other people don’t have when actually the other people probably have more insight into our situation than we do.”
  7. Reluctance to use debiasing techniques:
    “I think that’s where the issue comes in…if I’m willing to do it think about what an edge I’m going to have over people who aren’t willing to do it.”

Responding to Microaggressions

Micro-aggressions are verbal, behavioural or environmental indignities that communicate hostile, derogatory, or negative racial slights and insults to the target person or group. These could be accidental or on purpose.

There are three main ways to react:

  1. Let it go – this can be emotionally draining to confront. Yet silence places an emotional tax, making your ruminate on what happened and why.
  2. Respond immediately – call it out & explain its impact while the details of the incident are fresh. Immediacy is important to correct bad behaviour. However, but this approach can be risky – the perpetrator might get defensive, leaving the target feeling worse.
  3. Respond later – Here, the risk lies in the time lag, for it requires helping the person who committed the micro-aggression to first recall it and then to appreciate its impact. Bringing it up might be deemed petty — like someone who has been harbouring resentment or holding on to “little things” while the other party, having “meant no harm,” has moved on.

Framework for determining the best course of action:

Discern. If it is worth responding to. Knowing that you can choose to respond or not can also be empowering
Consider:

  • The importance of the issue and the relationship : If either is or both are important to you, chose to respond. Don’t avoid.
  • How strong is our feeling or emotion Honour the feeling, experience it and factor it into if, how and when to respond.
  • How you want to be perceived now and in the future :There are consequences to both speaking up and remaining silent. Determine which holds more weight in this situation.

Disarm. If you choose to confront a micro-aggression, be prepared to disarm the person who committed it. One reason we avoid conversations about race is that they make people defensive. Explain that the conversation might get uncomfortable for them but that what they just said or did was uncomfortable for you. Invite them to sit alongside you in the awkwardness of their words or deeds while you get to the root of their behaviour together.

Dig-in. Challenge the perpetrator to clarify their statement or action. Acknowledge that you accept their intentions to be as they stated but reframe the conversation around the impact on you. Explain how you initially interpreted it and why. If they continue to assert that they “ /didn’t mean it like that/,” remind them that you appreciate their willingness to clarify their intent and hope they appreciate your willingness to clarify their impact.

Decide. You control what this incident will mean for your life and your work — what you will take from the interaction and what you will allow it to take from you. Let protecting your joy be your greatest and most persistent act of resistance.

Remember to

  • Express yourself in a way that honours your care for the other party, and assert yourself in a way that acknowledges your concern about the issue.
  • Allow yourself to feel what you feel, whether it’s anger, disappointment, frustration, aggravation, confusion, embarrassment, exhaustion, or something else. Any emotion is legitimate and should factor into your decision about whether, how, and when to respond.
  • With more-active negative emotions such as anger, it’s often best to address the incident later. If you’re confused, an immediate response might be preferable. If you’re simply exhausted maybe it is best to let it go — meaning best for you, not for the perpetrator

When you maybe at fault, remember

  • Intent does not supersede impact
  • Seek to understand the other person’s experience
  • Believe when they choose to share their insights; don’t get defensive
  • Get comfortable rethinking much of what you thought to be true about the world and your workplace
  • Accept that you have likely been complicit in producing inequity

sources

When and How to Respond to Microaggressions
emotional tax
Avoidance can be the wrong approach.

The Generalist’s Dilemma

Playwright Robert Greene infamously referred to his peer, William Shakespeare as “Johnny do-it all”, in an oblique reference to Shakespeare being an actor turned playwright. Jack of all trades, master of none is an often used phrase today. In Middle Age England, several trades had a jack of some sort – lumberjacks, steeplejacks and Jack-tars (sailors). These jacks were often master craftsmen in their chosen trades. The original, “Jack of all trades” didn’t actually carry negative connotations, until ‘master of none’ got added much later.

Today, most of us can feel this dilemma. At our best, we experience the imposter syndrome of not knowing if what’s the right thing. At our worst, we toot chauffeur’s knowledge & managementese. There are as many specialisations today as ambiguous problem statements, that I often don’t even have the right word to explain that feeling of trying to keep pace.

Recently, Elon Musk, the world’s riches person added fuel dilemma when he said in a tweet [4]:
“I strongly believe that all managers in a technical area must be technically excellent. Managers in software must write great software or it’s like being a cavalry captain who can’t ride a horse!”. This, coming from a business man whose span ranges across diverse domains like space travel, electric cars, tunnel transportation and social media – to put it mildly – was odd.

This is the generalist’s dilemma – “How much specialisation do you need to contribute effectively?” The answer, as I now understand, is both – not much and a lot. Both at the same time.

Expert managers often undermine the work

Ian Siegel, who built ZipRecruiter from his kitchen table to a listed company, recalls this story as pivotal moment for him,
“I had this rude awakening. I remember it so clearly. They had me interview someone who had come out of a marketing media company who was a buyer and in the interview, I had with him for 20 minutes he said not one thing I understood but they were all excited about him. I was like “guys, you are going to hire that guy. I have no idea what he does or how he does it. Like, he made no sense to me. He spoke in jargon the entire time.” So, we hired him over my apparent objection. And the first day he was on the job, he goes, “Hey, where are the audit logs of ads running?” And I was like, “What’s an audit log? He is like “the thing you get from the TV stations that show you that they ran your ad when they said they did so that you can make sure you’re not overpaying them.” And literally the first day he saved us a million Dollars because they had not been running the ads. …

At the stage Zip recruiter was then, a million dollars was probably game changing.

With that in mind, let’s start with the premise Elon’s is wrong. So, How can a good manager without coding skills know the project is well done?
Firstly this questions belittles the creative aspect of coding. It is like saying unless you are a master artist, how can you know my art is good? The simple answer, as eloquently articulated by an expert engineer turned manager Attila Vago, is – “You don’t. Not from looking at the code, for sure. A good manager will ensure they have the right people in the team to enable productive development environments, stringent testing procedures and the skills of each member compliment each other enough to have high enough confidence [that] only quality software goes live.”

Companies and managers hire engineers not to tell them what to do, but the other way around. One hires professionals to rely on them, not put them on a leash.

~ Attila Vago [5]

If, as a managers, your instinct is to roll down your sleeves each time to expertly guide the cavalry, you will become the rate limiting factor.

This raises an uncomfortable question — doesn’t my manager need to understand what I’m doing? The answer is – yes but certainly not at the level you think. Says, Vago, “Your [engineering] manager will need to know that what you’re developing is according to requirements, that you address merge issues, adhere to testing and design guidelines, and you’re conscientious enough to deliver on what you promise. Everything else is between you and your team-members, from the designer to the quality engineer. For great code, you’ll get praise from your engineer colleagues, not your manager. Your manager will pat you on the back for getting the desired results”. Ian takes it a level higher, saying I literally am practicing the discipline of not even giving my opinions anymore. What I try to do is ask questions. Tell me why you are thinking a testimonial-style commercial is a right approach for us at this point? I try to just elicit them to explain their strategy to me, so that they are listening to themselves, explain it out loud, and then, we have a dialogue about their answers instead of me saying like, “I don’t think we should do a testimonial-driven commercial right now. Too many people are doing it.

Yet, if generalists are all about soft skills that are often hard to reflect on oneself or others, how does one know where to improve? Doesn’t this open up room for all the Dilbertese today? To me, the answer is counter-intuitive. The term generalist is a misnomer, often misunderstood as the opposite of a specialist.

A generalist is a different kind of specialist

It is usual for CEOs to be generalists but rarely so for a head of finance or legal or technology, right? Wrong. To be really good at their jobs, each of these functional leaders need to be generalists. So what then constitutes a generalist?

To me generalists are folks with a special skill set, a secret ingredient – systems thinking. In business this is a deep understanding of the company’s environment, its business and operating models. Generalist are experts in understanding & building complex systems. Each functional leader needs to build unique and intricate mental models (& system models) in the domain they oversee, which also has myriad specialisations. However, it also needs to be expansive enough to overlap with others domains. To be able to see interlinkages and to identify both opportunities and possible points of stress and failure in the system.
Collectively the management team’s models form the company’s system, which evolves dynamically. The CEO operates similarly, but from a different perspective of integrating functional management, shareholders, regulators and lately, even the society.

Why do so many of us love to work with specialist bosses then? That’s often because, we usually don’t have all the skills for that role and expect our managers to teach us. Teaching you is not their day job, although learning to be effective is yours. Rarely, it can happen that the knowledge involved is so specialised and intricate that you need an apprenticeship model to transfer knowledge. That, however need not be a manager-reportee relationship. As in Ian’s media buying example, the inverse of this is more common.

However, organising work with system design principles has two key challenges. First this needs a dual mindset that is not intuitive at an operating level; and second we need to learn a new mental toolkit to help us design, build and observe system flows..

The generalist’s mindset

Kenneth Boulding’s personality itself is a great example of the dual mindset needed for system thinking. Kenneth, was an economist and one of the founders of general systems theory. He had varied interests spanning across peace studies, general systems, volumes of poetry, ecology and social theory, to name a few. Elise Boulding, his wife, wrote:

Kenneth delighted in life. Nothing was too small to escape his absorbed attention. He always carried a tiny but powerful magnifying glass in his pocket so he could absorb details invisible to the naked eye of any object. By the same token, nothing was too large or too far away to escape his interest. At night he would mount his trusty telescope on the porch and lose himself in the stars.… his way of seeing things was so unique that what people remember best about Kenneth was the unexpectedness of his observations, the unusual connections his mind was always making. Kenneth’s mind at work was a mind at play.

The book, System Thinkers [7]

This mindset is the ability to zoom in with curiosity and zoom out with wonder and yet always look for new patterns, unexpected connections in an imaginative, playful manner.

The mental toolkit

I don’t consider myself an expert in system thinking, so I wont delve into some of its core concepts yet [8], but I’ve discovered a broader toolkit that is helpful as a starting point. I’m only including brief ideas summaries here as inspiration

  1. Learning quickly: The ability to learn something new fast enough from a diverse set of resources – books, articles, people, courses and more
  2. Creating new abstraction models: Summarising learnings into abstractions & models that an eight grader can understand and technical experts reluctantly agree
  3. Rethinking these models: When something doesn’t make sense, slowing down to listen deeply for critical learning so you can upgrade your models
  4. Reverse mentoring: Learn from younger folks, create abstractions they agree with and rethink those models as you learn something new
  5. Sythnesis : The ability to combine two or more things to create or infer something new or novel
  6. Attention to feedback : Pay attention to the feedback loops. Look for things that confirm and for those that don’t conform.
  7. Ask better questions: The simple act of searching for the right question is more powerful the knowing the right answer. I’ve written a separate essay on this (here ).

This is, but a starting point in resolving the generalist’s dilemma, not the solve. What are some others ideas that you deem worth exploring ? Let me know in the comments below.

Sources

[1] The saying ‘Jack of all trades’ – meaning and origin.
[2] Nandan Nilekani on rethinking how to regulate
[3] Unified Payments Interface – Wikipedia
[4] Elon Musk on Engineering Managers
[5] Managers who are experts undermine the work
[6] https://www.linkedin.com/in/attilavago/
[6] 2021: The year UPI became the undisputed payments champion
[7] Systems Thinkers | SpringerLink
[8] The 6 Fundamental Concepts of Systems Thinking
[9] [An introduction to systems thinking | Draper Kauffman
[10] 20VC: The Job of the CEO is Do As Little As Possible