Pessimist, meet Optimist

Hoping for the best, prepared for the worst, and unsurprised by anything in between.  

—Maya Angelou

A co-write with Pat Kua (The Optimist) and Jonny Schneider (The Pessimist).

Being optimistic isn’t better than being pessimistic, and being either exclusively isn’t enough to win. Instead, high performing teams acknowledge the role of both, and create systems of work that exploit their benefits equally. Let’s unpack optimism and pessimism, and look at ways to make the most of both in your team.

The miracle project

We’ve all worked on a Miracle Project during our time building digital products. These have an ambitious scope, often with a fixed deadline, and all the stars have to align in order to succeed. I remember working on a complex programme, trying to help a cash-rich company aiming to launch a complicated social network. They’d bought seven smaller companies, figuring that integration was going to be the easy part. They didn’t realize each company used significantly different technology stacks, had products with strong overlap in some areas while missing gaps in others, engineering quality was variable, and many of the same terms were used to mean different things. No amount of optimism could help this project meet the deadline handed down. Instead, a healthy dose of pessimism might have saved this company time and money.

There is a time and place for both optimism and pessimism.

Big vision

It’s hard to envision possible futures that are worth pursuing without letting go of the constraints of today. Optimism becomes table stakes for imagining what might be possible, creating excitement, and motivating people. It’s how we think bigger, push boundaries, and get beyond local optimisation to reach new peaks. While a lot of customer innovation happens through persistent, methodical, and diligent work to iterate to success, most of the world’s great innovators aren’t known for it. Instead, they live in the future, obsessed with impossible missions, and are often considered unhinged and a little bit whacky.

Teams and organisations need both optimists and pessimists. Without big thinking and unhindered optimism, it’s too easy to become preoccupied with incremental change that makes things better but doesn’t change the world. Yet executing on a big vision requires us to systematically identify and de-risk big assumptions. It’s how we manage risk, because ignoring them and focussing on optimistic thinking doesn’t make them go away.

Stay with us to find out how to embrace both in your team. Find out how to see your team’s bias, what to do about it, and some practical methods for exploiting optimistic and pessimistic mindsets at different stages of the product development lifecycle.

Know your bias and don’t apologise for it

Pessimists exploit their state of mind to be well prepared, predict future challenges, and find multiple ways around them. There is value in this mindset. Jonny is naturally a pessimist, and he is not sorry, even when the optimists among us find it uncomfortable. He likes big ideas, but also believes that ideas are cheap, and we can save a lot of time, money, and grief by killing bad ones before even getting started.

This can be problematic. When pessimists work with pessimists, we risk a pity party. We perceive it will never work, failure is inevitable, and there can be no path forward. Okay, now what? That’s a dead end. Things go better when pessimists mix with others who have an equal and opposite bias for optimism. The people Jonny loves working with the most are not like him, and it works because they’re different. Optimism tempers pessimism. We don’t have to change our beliefs, agree, or even get along with someone who has a different mindset. The healthy tension of disagreement is often positive. We can acknowledge the difference, and use it to break through dead ends.

When developing strategy, a pessimist might focus too much on low-risk goals that are likely to be achievable. This usually is not the bones of meaningful product innovation – we do not build things only because we can. Optimism disrupts this default thinking. Sure, the wackiest thoughts and ideas might be high risk, packed with assumptions, and challenging to execute. But when we get the balance right, we’re drawn into the sweet spot.

Now we have a meaningful aspiration for the tomorrow we desire, we are motivated to act, and although there will be challenges to navigate, we move with eyes open, and can tackle what’s ahead. Think of Elon Musk’s visions to build an autonomous electric car with Tesla or live on Mars with SpaceX. Tesla and SpaceX wouldn’t have existed without the optimism of doing something that has never been done before. At the same time, both would have remained only a vision without a dose of pessimism to recognise and overcome current constraints. Now think of Theranos. That was all optimism, and no pessimism, and it didn’t work out for Elizabeth Holmes.

Ways to exploit pessimistic and optimistic mindsets

Here are a few favourite ways to bring the pessimist to the party:

Doomsday planning

Get your futurist hat on and challenge yourself to think about multiple possible futures for your business. Focus on the most destructive or disruptive scenarios, e.g. what would you do if there was a structural change in your industry, or how would you respond if Apple entered as a competitor. Further reading: The Art of the Long View: Planning for the Future in an Uncertain World (Schwartz, 1996)

Chaos engineering

To test performance and resilience of technology infrastructure, engineers intentionally introduce turbulence to create conditions of failure, for example, randomly killing a network service or dropping servers, databases, or other infrastructure. These experiments reveal how systems respond to failure modes, so that vulnerabilities can be addressed and resilience built-in. Netflix created a tool called Chaos Monkey, to run failure experiments in their production environments. Knowing that it could run at any time helped them to not only build fault tolerant services, but to recover gracefully from big failures.

Add artificial constraints

Big audacious goals and aspirational visions can sometimes feel insurmountable. If you’re stuck on where to start, try adding constraints. For example, ask: What if we had only 6 weeks instead of 6 months investment runway? Now see how that changes the discussion. You might be surprised how quickly this brings into focus the things that really matter. Create your own list of ‘what if…’ questions to jam on with your teams.

Embrace criticism

In Radical Candor (St. Martin’s Press, 2017), Kim Scott encourages what she calls an ‘obligation to dissent’. In her work training managers at Google, Scott found they were missing out on insight, critical thinking, and feedback that would help teams to win because people feared their input would not be well received, and they didn’t want to be seen as detractors. Recognising the missed opportunity, Scott normalized critical feedback by implementing a simple mechanism in meetings. Obligation to dissent is where participants are asked, encouraged, and expected to openly share criticism on the topic. And when they do, their contribution is valued and celebrated, without fear or consequence or repercussions. While unnatural at first, Scott eventually created a culture of feedback that helped teams perform at their best.

Similarly, In Design Crits, the best designers anticipate criticism of all kinds. They actively encourage critics to purposely break the solution, and then take the feedback into the next cycle of design improvement.

While these approaches from management and product design are applied differently, they are both examples of embracing a pessimistic mindset to harvest insight that improves ideas.

Now that we have some strategies for getting best from the pessimists, it’s time to look at how to use optimistic approaches during product development.

  • Blue Sky Thinking (remove constraints) – During discovery or brainstorming processes, ask people to imagine the possible and ignore the constraints or rules of your current organization. Separate generating ideas from evaluating or critiquing those ideas to have the broadest possible choices.
  • Ask, “What if?” – If you find your discussion blocked, ask people, “What if X were no longer a barrier?” Ask people to temporarily suspend their worries or concerns and you might find your discussion flows further.
  • Draw on Futurespectives or Pre-Mortems – Retrospectives or post-mortems look at events after they happened. Futurespectives and pre-mortems imagine a future where you’ve overcome all obstacles to reach your goal. Draw upon these activities to identify potential obstacles but also to start building plans to prevent the obstacles from being complete blockers to your goal.
  • Set big ambitious goals – People are drawn to missions that have never been done before. Ambitious goals create opportunities for people to invent new approaches and techniques, learn and grow and a huge sense of accomplishment with every step forward.

What it all means, and how to get started

As humans, we tend to group up with likeminded people. That might be more comfortable, but it’s probably a mistake in product innovation. When it’s all pessimism, the art of the possible gets lost in the weeds, we lower the bar and wind up with plans that are pedestrian at best and hard to stay motivated by. When it’s all optimism, we risk being seduced by fantasy and invest in unwinnable missions that set teams up for failure.

The best thinking often happens when we purposefully seek diverse inputs from people with different mindsets, opposing views, or competing beliefs. This isn’t about consensus, and we don’t need to agree. The debate of many minds makes our thinking more robust, strategy more resilient, and informs better decisions along the way.

You likely have a sense of where you and your team fit on the spectrum of optimism and pessimism. Have the conversation with your team, and start implementing strategies like the ones in this article to help your team think differently to its default state. There’s individual growth here too. As a team begins to value both mindsets, in time, many who identify as optimists learn how to think like pessimists, and vice versa. It’s a killer skill for life and work, and one that’s worth investing in.

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