Good Mistakes

Delivering sales results requires taking chances and better decision making

How many decisions do you make in a day? Numbers widely range depending on the source from 70 to 35,000 decisions, but it is probably more than you may think.

Our ability as sales professionals to make good decisions is critical for our success. What makes sales so interesting and frustrating is the human dynamic, the building of relationships, and weaving multiple motivations, initiatives, and resources to seal a deal. If we make enough right decisions, we can build a repeatable sales process and generate consistent revenue.

With that in mind, I want to dive into some strategic frameworks over the next several weeks that can help us as sales professionals make better decisions. To kick off this series, I want to share an essay I wrote for another newsletter I publish with some modifications from the original to better align to a sales context for this community.

John Lewis was a portrait in courage. Already weathered by his experiences standing up to hatred and racism across the Southern US, he faced his hardest test yet on March 7, 1965 before the Edmund Pettus Bridge in Selma, Alabama. He stood with 600 others on a march to Montgomery when the marchers were attacked by state police. Lewis sustained a skull fracture, and many others were injured in an incident to be later known as “Bloody Sunday”.

Last week, I watched a documentary about the life of John Lewis. He never stopped fighting the good fight, even up till his passing last July. If there was one theme that could capture the full breadth of his life’s work, it would be summed up by his quote:

“Never, ever be afraid to make some noise and get in good trouble, necessary trouble.”

He understood that to make change means disrupting the status quo. To disrupt centuries of institutionalized racism meant an even greater change in culture, society, and politics. The only way to ensure change builds momentum and leads to an end to racism and injustice would be to confront people and systems intent on maintaining the current order. Good trouble was John Lewis’ way to bring about positive change.

With fifty years of hindsight, we can all agree that the events in Selma was wrong. At the time though, this was not the case. Institutionalized racism in the US was accepted instead of being seen as an affront to dignity and human rights. It took the brave few to walk across the bridge and speak up against unfairness, cruelty, and oppression.

"When you see something that is not right, not fair, not just, you have to speak up. You have to say something; you have to do something."

Over the past several weeks, there have been several instances of the people speaking up against injustices in the tech world. A well-known AI researcher and ethicist at Google, Timnit Gebru, was abruptly dismissed over the publication of one of her research papers. More recently, GitHub got into hot water for firing an employee posting in a company chatroom comments about the racist ideology of some of the participants of the January 6th riots at the US Capitol. In both incidents, employees spoke up to expose injustices and push for change.

If the initial mistake was bad, the official response was even more tone deaf. It follows a typical pattern. The first response is to blame the victim. Next is to place fault with the systems. Then it is to issue a tepid apology that avoids directly addressing the concerns raised by the injustice. Last step is to hope everyone forgets the controversy and to avoid any real concerted efforts to change. To GitHub’s credit though, they did eventually take ownership and responsibility for their exceedingly poor judgment.

These are all examples of bad mistakes, the type of mistakes we do not learn from. The reason learning from mistakes is hard is because we think of mistakes as one way doors. The blame and embarrassment overshadow the potential for catharsis, reconciliation, and understanding. Our brains are hard-wired to avoid blame and to prioritize short-term desires, preventing us from acknowledging the mistake, unwinding our bad decision, and apologizing.

In corporate blame culture, we observe the same ritual. A critical app goes down, a big deal unravels, or a marketing campaign flails, and we need to find fault in the people or person. There is little appetite for mistakes, so employees and teams avoid risks, suppress change, and engage in elaborate exercises to pass the blame while hoarding the glory.

It would be a mistake to call mistakes one way doors though. The vast majority of decisions we make are never final or irrevocable. Often we make decisions based on incomplete data or experience, only to discover something new and enlightening in the process that allows us to continue on, pivot, or roll back our decision. In that sense, mistakes are really two way doors, or what I call good mistakes.

Good mistakes are ones that we learn from and that improve our decision making. Many mistakes can be good mistakes if we operate in a blame-free environments, the type in which the culture values learning and transparency. Even terrible mistakes can be valuable if they lead to better ways of handling future situations.

Do all mistakes have value though? In my talk “Failure at Scale”, I proposed rather than looking at failure as a binary result, it is better to see failure as a scale. On one end, there are failures that result from incompetence, lack of attention, or outright maleficence. On the other are those failures that clarify, provide insight, or expand of our thinking. As an example, some mistakes lead to tragedies like Chernobyl or the Challenger disaster while some lead to surprise innovations like the polio vaccine or the light bulb.

Culture in this case plays a significant role. Good mistakes thrive in a generative culture where everyone is aligned to the values of the organization, trust is strong and the default interaction mode of people and teams is collaboration. The more bureaucratic or pathological the culture, the less likely good mistakes will arise, be supported, or advance positive change.

Another consideration when it comes to mistakes is one of impact. On sales teams, there are thousands of seemingly small decisions we make each day, any one of which can have major downstream impacts. We put little emphasis on the small bit of research and personalization in our prospecting, when this little bit of extra effort can help us stand out with prospects. On the other hand, we over-index on demos and pitch decks when the most impactful thing we can do is have an open and thoughtful conversation with prospects. This is what made the difference when selling in APAC, a region of the world where I had no connections or experience.


The last consideration is speed. Startups are generally faster to act and faster to iterate over larger, more established organizations. When mistakes arise and new insights are revealed, the lack of established process, embedded political structures, and organizational barriers means change happens sooner. This leads to faster innovation, swifter adoption of change, and more nimbleness when taking corrective actions, if enacted fast enough.

Framing decision making in the lens of value, culture, impact, and speed with the understanding that very few decisions are one way doors leads to better outcomes. Good mistakes in that sense are really just experiments towards better understanding that give us the safety to reverse ourselves. The more generative the culture, the more willing they are to accept that mistakes are not errors, but unexpected results that open new doors.

There is a lot more to making effective decisions that I will discuss in future essays, especially recognizing cognitive biases and the role empathy plays. In his recent Presidential Inaugural address, President Joe Biden asked, “If we’re willing to stand in the other person’s shoes just for a moment.” Indeed, if we could spend more time to listen, understand, and empathize with the perspectives of others, how much better would our decisions be?

This is the starting point in elevating the state of the sales profession and the impact we can have, which I will discuss in the next post.

Mark Birch, Founder of the Enterprise Sales Forum

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