If you want to shift a culture the most effective way to do it is to change who you hire. It’s far easier to hire for traits you need than to try to transform a person who doesn’t have them into someone that does. The more people in an organization that successfully demonstrate a trait, the easier it is for others to emulate and adopt it.

How to shift a culture

Some people ask more questions, have more doubts, and are willing to act on them. They are harder to manage since they naturally challenge authority, but if you want assumptions challenged that includes the assumption of hierarchy.&nbsp;If healthy debate is encouraged the results will be the best synthesis of different assumptions.

Better at challenging assumptions

If you as the manager continually demonstrate that you are comfortable being challenged, or yielding your idea to a superior one suggested by a colleague or subordinate, everyone who works for you will emulate that behavior.&nbsp; If you dismiss challenges or yell at people who challenge you, the culture of fear your behavior creates will dominate no matter who you hire or how great you proclaim it is to challenge assumptions.

It takes great confidence

Healthy debate is easy if no one is taking the results personally. Most heated debates involve people who have trouble separating their opinions from their identity. If I draw what turns out to be a bad idea on a whiteboard, in a healthy culture it’s reinforced that the idea is lame, but I’m not. I can still be smart and valuable.

Separate people from their ideas

<ul><li>Postmortem / Debrief: after every project, a long conversation should take place where people review what happened, what assumptions were made, what went well and what could have gone better.&nbsp;</li><li>Experimental attitude:&nbsp; “Let’s try working this way for a week and see what happens.” The continual exposure to the cycle of “assumption, test, learn, repeat” diminishes fear around asking questions and raises everyone’s comfort with making, challenging and testing assumptions.</li><li>Discuss books about thinking: Are Your Lights On? is a favorite for inspiring people to think more critically, and humorously, about everything.</li></ul>

Challenging assumptions

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From Monday's <a href="https://scottberkun.com/2013/qa-monday-ask-me-your-questions/">pile of questions</a> reader <a href="https://scottberkun.com/2013/qa-monday-ask-me-your-questions/comment-page-1/#comment-141380">Ev Larsen asked</a>:
<blockquote>
Assumptions have an unnerving way of becoming facts and received wisdom over time. How do you build some functional assumption-checking into a project team, a process that generates useful feedback and moves the team effort forward?
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The best answer to questions of culture is you hire for it. Culture change is slow, much slower than technological change. This mystifies technocrats, as it should. People are much more challenging and powerful than machines will ever be.
Want more creative teams? Hire creative people. Want more risk-taking? Hire for it. No single act defines an organization's culture more than who is hired and why. If you want to shift a culture the most effective way to do it is to change who you hire. Yes, you can try to lead your current staff in a new direction, but if you've hired people in the past primarily for being polite and staying in their lane, the shift to preferring debate and challenging assumptions won't be an easy one.
The reason is simple: people are stubborn. By the time we're 25 many of our personality traits, desires and habits are well defined and unlikely to change (it's certainly possible but odds are against it). The primary point of leverage then is who a manager hires (and fires) and why. It's far easier to hire for traits you need than to try to transform a person who doesn't have them into someone that does. Even if transformation is the goal, we are social creatures and learn best from the examples around us. The more people in an organization that successfully demonstrate a trait, the easier it is for others to emulate and adopt it.
One weakness of managers is their faith in the omnipotence of management. There is the belief, reinforced by management consultants and business books, that simply by decreeing "be innovative" or "work smarter" magic forces that transcend the limits of sociology will transform conservative or stupid people into being otherwise on your behalf. The ability of a manager to achieve something depends heavily on whether the people on staff are even capable of doing that thing. You couldn't convert the local bakery into a nuclear physics research lab simply by changing the manager or the management philosophy, but that doesn't stop executives from trying. The current trend of organizations built for decades around core values of conservatism and rule-following magically transforming into entrepreneurial risk taking powerhouses simply because the CEO tells them to is a classic example of this hubris.
A related challenge is for a leader to embody the change in their own behavior. Anthropology teaches us that people respond best to leaders who model behavior, rather than those who simply dictate it. But this requires a leader who is self-aware enough of their own tendencies and who is willing to embody the shift they want in their organisation in their own behavior.
My broad ranting aside, to answer the specific question some people are instinctively better at challenging assumptions than others. They ask more questions, have more doubts, and are willing to act on them. I don't know why they are this way, but I know these people exist. If you want more assumption checking, hire for it. If you don't have the power to hire, provide a new way for them to make themselves visible. Then promote and reward people who exercise these traits, as that's a way to signify to others what is valued and what is not.
These people are harder to manage since they naturally challenge authority, but if you want assumptions challenged that includes the assumption of hierarchy. Diversity is a natural way to bring more questions into an organization as people with different experiences naturally question each other when they get together to build something. Age difference is one of the most useful kinds of diversity as new graduates and old veterans have many different assumptions, and if healthy debate is encouraged the results will be the best synthesis of those perspectives.
The second part is how you as the manager respond to having your assumptions challenged. If you continually demonstrate that you, the person in charge, is comfortable being challenged, or yielding your idea to a superior one suggested by a colleague or subordinate, everyone who works for you will emulate that behavior. Alternatively, if you dismiss challenges, or yell at people who challenge you, the culture of fear your behavior creates will dominate no matter who you hire or how great you proclaim it is to challenge assumptions.
The platitude "there are no sacred cows" is very easy to say, but I've rarely heard it said by someone who didn't really mean "only my sacred cows are sacred." It takes great confidence as a leader to keep an open mind as the size of their empire grows.
The third part is behaving in ways that separate people from their ideas. Healthy debate is easy if no one is taking the results personally. Most heated debates involve people who have trouble separating their opinions from their identity (the lack of ability to find any humor in a debate is a good sign that someone is taking the issue too seriously). If I draw what turns out to be a bad idea on a whiteboard, in a healthy culture it's reinforced that the idea is lame, but I'm not. I can still be smart and valuable. Perhaps my lame idea will help lead to a great one. This trust in coworkers is what allows ideas to be debated, attacked, torn down, twisted, reused and improved without any fear of offending anyone. Most successful creative cultures in history were based on this separation. It's another set of behaviors that leaders must demonstrate regularly. Many talented organizations produce little of merit because of how <a href="https://scottberkun.com/essays/35-how-to-give-and-receive-criticism/">sensitive people are of criticism</a>, and the fear of offending people or being offended trumps everything else.
There are definitely techniques that encourage the challenge of assumptions but they only work if the above factors are true. My favorites include:

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	<li>
Postmortem / Debrief: after every project, a long conversation should take place where people review what happened, what assumptions were made, what went well and what could have gone better. If lead properly (and witch-hunts and finger pointing are avoided) these conversations are gold. They inject introspection and self-awareness into the culture.</li>
	<li>
Experimental attitude: The basic notion of an experiment is you have a hypothesis (which is really a set of assumptions) and you find a way to test it to see if it's right. Most experiments fail, but the attitude is it's the only way to learn. Leaders should always be running experiments of some kind with their teams. "Let's try working this way for a week and see what happens." The continual exposure to the cycle of "assumption, test, learn, repeat" diminishes fear around asking questions and raises everyone's comfort with making, challenging and testing assumptions.</li>
	<li>
Discuss books about thinking: many books address problem-solving, question asking, and challenging assumptions, and if read as a team provides a meta-example for exercising what the books try to teach ("e.g. what assumptions in this book about questioning assumptions should we question?) Although it's more about problem-solving, <a href="https://www.amazon.com/exec/obidos/ASIN/0932633161/scottberkunco-20/">Are Your Lights On?</a> is one my favorites for inspiring people to think more critically, and humorously, about everything.</li>
</ul>

What do you think? Are there other methods to encourage a culture of questioning assumptions?
<a href="https://pxhere.com/en/photo/1448359"><img src="https://i0.wp.com/scottberkun.com/wp-content/uploads/2013/06/bbe8d551d7d4adf1a37e6fb8d9d0-1448359.jpg?resize=600%2C400&amp;ssl=1"></a> </div>

From Monday's pile of questions reader Ev Larsen asked: Assumptions have an unnerving way of becoming facts and received wisdom over time. How do you build some functional assumption-checking into a project team, a process that generates useful feedback and moves the team effort forward?

How Do You Build a Culture of Healthy Debate?

How to shift a culture

Better at challenging assumptions

It takes great confidence

Separate people from their ideas

Challenging assumptions

It's time to
Read like a Pro.

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How Do You Build a Culture of Healthy Debate?

How to shift a culture

Better at challenging assumptions

It takes great confidence

Separate people from their ideas

Challenging assumptions

It's time to Read like a Pro.

How Do You Define Startup Culture?

How to Build Culture in a Remote Team and Scale

A Simple Introduction to Lean UX

It's time to
Read like a Pro.