The Mindset of “Try It” then “Learn From It”

During my last ten years at Microsoft, the company went through a significant cultural transformation.  In order to innovate, create long-term partnerships, and retain mature talent, Microsoft had to evolve. The days of being a brash dominator were over, and Microsoft entered into a new era of greater collaboration.  The CEO, Satya Nadella, had a saying: “Be a Learn-It-All and not a Know-It-All.” On the surface, this seems simple, but there’s a lot to it. In this article, I’ll tell you how I think about it, the ways to put it into practice, and the benefits you’ll gain.

We all have that Know-It-All person in our life.  Go ahead and think of them now.  Are you making a face?  Maybe you feel a little queasy?  Perhaps a zap of pain remembering an uncomfortable conversation?  Whatever you feel, it likely isn’t positive.

I have some news for you.  ALL of us have moments of being that Know-It-All. We CAN break out of those Know-It-All moments and become a Learn-It-All.   This mindset applies to both individuals and organizations, and is so powerful that:

  1. Fear is reduced.
  2. Risk tolerance increases.
  3. Innovation is unlocked.
  4. Thinking, communications, and actions are freed up.

The primary difference between a Learn-It-All and a Know-It-All is that a Learn-It-All is open to asking questions and trying something new. They learn from failure, adapt, and then try again.  As a bonus, a Learn-It-All is generally more pleasant to be around.

A Know-It-All will reject all new ideas.  Why?  Because they Know-It-All!  Trying something new is at the heart of innovation. And innovation demands a Learn-It-All mindset.

What Does a Learning Mindset Look Like?

Okay, I want to be a Learn-It-All.  It seems like I should just ask a bunch of questions, and I’m all good… right?  Not exactly.  You must be intentional in how you word your questions and express your values.

How to word Learn-It-All questions

Be clear that you’re asking questions with the intention of learning.  When we ask questions, we can have many different purposes.

  • Sometimes we’re pushing someone towards an outcome.
    “It’s cold outside. Do you want to wear a coat?”
  • Or we are asking them to commit to something.
    “We hosted Thanksgiving last year. Do you want to host this time?”
  • Or we are trying to choose between options.
    “I can’t decide between the pink or the mustard shorts. Which ones do you like?”

When trying to understand, be very clear that you are wide open to learning.  When you do this, the person you’re talking to will share more openly and honestly and be less guarded.  Ask questions such as:

  • “I know a little bit about this but have some gaps. What do you think?”
  • “I’m interested in what you’re saying. Tell me more.”
  • “I want to learn about this. Please fill me in.”

Use the magic words: “Tell me more.”

Express Your Learn-It-All Values

It’s not enough to ask good Learn-It-All questions.  While many folks around you will pattern match and follow your lead, not everyone will do so.  By stating that you value a Learn-It-All mindset, you are leading those around you with clarity and strength.

How to do this?  It’s simple.  Tell people what you’re doing in plain language.

  • “I want to be a Learn-It-All and not a Know-It-All.”
  • “I don’t believe there’s only success or failure. Every time we don’t succeed, we learn, and I expect us to adapt and grow from those learnings.”
  • “We will take smart risks. If they pan out, great.  If they don’t, then we’ll adapt and try again.”
  • “I want to try ‘X.’ After two weeks, we’ll circle back and assess ‘X’ and figure out what worked and what didn’t.”

Now that you know the vocabulary and how-to’s, what gains should you expect?

The Benefits are Real. 

When you function this way, you can drive a massive upgrade within your environment.

  1. Don’t think in terms of “Success or Failure”. 
    This is too binary. You KNOW there will be many failures – especially in businesses that rely upon innovation to survive.
  2. Instead, think in terms of “Success or LEARNING”. 
    We didn’t fail.  We tried something, it didn’t work exactly as expected, we learned more, and we can now set a better direction based upon those learnings.
  3. By embracing a learning mindset, you are establishing psychological safety for your organization.
    Why?  Because if the risk doesn’t work out, it doesn’t count as a “failure”.  It counts as a “learning”.
  4. When people feel safer, they are more likely to take risks.
  5. It’s those risks that drive innovation and growth.

Success or Failure Learning

Be willing to put this into practice:

  • Agree to someone’s two-week experiment – even if you think it won’t work.
  • Say you’ll try out something three times and then assess.
  • Make a change you’ve been putting off and set a monthly reminder to evaluate how it’s going.

You may have some successes, and at minimum, you’ll exit with some learnings.  Most importantly, you and your team will be building your Learn-It-All muscles.

Learn-It-All: Take SMART Risks.

Learn-It-All is not a license to make poor decisions or take bad risks.  And, I’m NOT advocating for going hog-wild and changing everything that’s currently working.  That would be leadership malpractice.  In fact, if you – or others in your organization – acquire an endless list of “learnings” and zero successes, you may be in the wrong role.

I AM encouraging you to open up and take some calculated intelligent risks.

Adapt your mindset.  Consistently be a Learn-It-All, and watch yourself and your teammates grow.


In 2018, I published my 11 most important lessons from Microsoft email, and over 25,000 people read it and forwarded it to their friends and colleagues. Many people asked me to write in more depth about the topics in the email, so that’s what I’m doing. I’ve spent the last year writing and will share more of that content at If you find this interesting, please forward the articles, subscribe to my email list, and follow me on LinkedIn.