The Best Lessons I Learned from Mike Kropp


Lessons Learned from Mike Kropp - 2

“When the student is ready, the master appears.” — Buddhist Proverb

Mike Kropp has been one of my best mentors at Microsoft.

He’s been my mentor for several years, growing my skills and maturing my thinking.

In my experience, Mike is one of the most effective leaders at Microsoft. He makes things happen with skill.

He sets a high-bar for himself and he leads by example.

Drive from Impact

Mike is always testing himself and improving. He drives from impact, and he empowers people to make things happen.

And, when it comes to employee engagement, he’s a tough act to follow.

Mike also has very seasoned executive skills from real-world experience, the school of hard knocks, and his amazing mentors. These skills are gold, and I’ve greatly appreciated the lessons he’s shared with me over the years.

A Greatness Coach at Heart

Mike also has unique experience in that he’s successfully started businesses from scratch within Microsoft. If you know what it takes to start a business at Microsoft, that’s a non-trivial statement.


True to his nature, Mike started the patterns & practices team at Microsoft to share proven practices for customer success.

He’s a coach at heart. In fact, he’s been a soccer coach for years. He brings this coach mindset to work to help people play their best game, and lift people up to be their best.

Top 3 Best Lessons

These are my top 3 great lessons from Mike:

1. A sense of urgency.

There’s no time like the present.  A sense of urgency leads to inspired action.  People take decisive action and make moves like they mean it.

When there’s no sense of urgency, there’s no compelling reason to take action and ideas and change die a slow crippling death or get lost in analysis paralysis, or people get bored and move on to new things.

2. Win the hearts, the minds follow.

Mike’s super skill is connecting with people’s passion and creating a compelling future.  He doesn’t start with the business case.

Instead, he starts with, “How is the world going to be different?”

It’s about dreaming big and putting together dream teams.  If the vision isn’t compelling, let’s not even start.  If the vision is compelling, then let’s find a way to carve it up and make it happen.

Now we can go to the details of the business cases.  Let’s not kill great ideas out of the gate before exploring how we can make the world a better place for our customers.

3. It’s all about impact.

Make an impact.  As a colleague put it, “this is your footprints you leave on the world.”

It’s all about impact.

Mike taught me the value of impact over efficiency.  First make impact, then you can optimize it.  Otherwise, you’re optimizing things that might not matter.

When you drive from impact, you inspire yourself, and you inspire others.  Small wins snowball into bigger successes and this creates momentum.

Your momentum feeds your passion, and the cycle starts all over again.

42 Best Lessons from Mike Kropp

Here are 42 nuggets or stratagems, where each one is a useful arrow to have in your quiver:

1. Live each day like it’s your last, but plan to live a 100 years.

What are you waiting for?  Take action now and start making impact today, but balance that with the fact you might be around a while.  In other words, don’t put your dreams on hold.

2. What are you about?

It all starts from here.   Lead from the inside out.  What’s your personal brand stand for?  Know your values.

Play to your unique strengths, and compensate for your weaknesses, where you need to.

Play where you can make the most impact, in a way that you can have the most fun.  Another way to think of what are you about is in terms of value to the company, your customers, or your tribe – what is the perceived future contribution you will make?

This is where your capabilities and brand paint a picture.

3. Ask better questions.

Before you can find the right answer, you need to ask the right questions.

One cutting question is always, “Who’s the customer?” or “What’s the customer experience?”

Asking better questions is a skill, and you get better with practice.

4. Do what you say you will do (DWYSYWD.)

This is leadership 101.   If you say you are going to do something, then do it.  It doesn’t take long to erode your credibility by saying one thing, but doing another.

When you do what you say you will do and you’re open and transparent with people, you build trust.

People feel like you got their back.  This means they will go out on a limb for you.  They don’t have to worry whether you mean what you say, or whether you’ll pull the rug from under them.

This is vulnerability-based trust in action.

5. Know the system you’re in.

Find the “centers of gravity” and know the levers in the system.  The centers of gravity are the key opinion leaders or people with power.

Walk the system end-to-end, identify the key levers in the system, and the key players in the system.

Walk the life cycle or map the system over time.  Know how decisions are made, how to influence the outcomes, and shape the impact.

Build allies before you need them and align your work to other workstreams where you can.

6. Use the system to educate.

Use the outside system to educate the inside system.   For example, rather than argue your opinion, leverage customer stories and data to educate on the inside.

Otherwise, it’s an uphill battle of proving your own credibility over just leveraging the system.

7. Don’t flip the bozo bit.

Always deliver compelling value, and focus on quality over scope.  Once you flip the bozo bit, it’s tough to flip it back, and people write you off.

8. “Would you bet your job on it?”

People quickly go from over-confident to more thoughtful, when Mike asks this question.

To be clear, it’s not a threat.

It’s a quick check to see how confident somebody really is when they make bold promises or pie-in-the-sky thinking without any accountability or thinking through any ramifications.

9. Get their fingerprints on it.

If you want support for your plan, from the people that will do the plan, then get their fingerprints on it.

Otherwise, you are on your own.  You can set yourself up for success if people who own parts gets on board.

10. Have the right people in the room.

Without the right people in the room, you have buy-in.  Without the right people in the room, you won’t think about the problem with the right lens or perspective.

Having the right people in the room means that you have the right coverage of the problem.

11. The tyranny of “OR.”

Rather than think “this” or “that” … challenge yourself to find the “AND.”

12. Survival of the fittest.

Mike often reminds us of the realities of business and competition with a dose of Darwin – “scarce resources drive the competition that leads to survival of the fittest.”

13. Read the situation.

The writing is often on the wall, if you look for it and are open to it.

Test the waters – ask questions.

14. Build a coalition of the willing.

Part of winning over your naysayers is having the right allies on board.  By getting the opinion leaders supporting your idea, you build momentum in the system, and this will help you deal with your worst critics.

An effective coalition isn’t a numbers game – it’s a perception game and it’s about having the right people backing your plan.

15. Are you a quarterback or a blocker?

Know whether you’re the one makes the passes or whether you’re the one blocking for somebody else.

It’s a simple metaphor but it can help remind you of your role or how you help out in the current situation.

16. Bow to the revenue god.

Just like you can’t argue with results, it’s tough to argue with revenue.  Profit speaks volumes.

If you’re trying to make a business case, or push your next big idea, you have to stack it up against the profit plan.

Passion is necessary but insufficient.  Profit is a key part of any sustainable business efforts – otherwise, you’re somebody else’s funding or cost or problem.

17. Make a product, the Star.

If a product group doesn’t support you, you’re done.

This is an important point, especially at Microsoft.

18. Know the waypoints.

You can use waypoints as a way to check direction and show signs of progress.  In GPS terms, a route is made up of two or more waypoints.

You can use this metaphor to think about how to chunk up a path from point A to point B.

When you chart a path, you figure out the waypoints to get there.  You can add milestones or checkpoints or other ways to check progress and direction along the way.

19. Know your Achilles heel.

Everybody has one or more things they wish they were better at.  Know your Achilles heel and pair up with people that help make your Achilles heel irrelevant.

If your Achilles heel is a real liability, then work at it, but don’t spend all your time trying to make it a strength.

Instead, spend that time investing in your strengths to make your true strengths that much better.

20. Speak softly, but carry a big stick.

Getting louder isn’t how you command respect or authority.   Think back to school to the teachers that controlled their classrooms effectively.

They didn’t do it by yelling.

In fact, the teachers that constantly yelled were the ones that were usually out of control.

21. Just enough process.

How much process do you need? … Just enough, and no more.  Process won’t make up for good people and it can get in the way of good people getting their job done.

Whatever process you use, make sure it’s more value than tax or overhead for the business, the people, and the outcomes.

22. Sometimes the best job, is the one you already have.

You can always start by making the most of what you’ve got.  Knowing your job and being great at your job sets a foundation to shape your job.

23. Don’t confuse concept with implementation.

Recognize a good idea when you see one.  Just because an idea doesn’t work out, doesn’t mean it was a bad idea.

Sometimes the market isn’t ready.

Sometimes the system you’re in wants something different.  If you factor out the implementation from the idea, then you can test different implementation paths.

24. Run the decision into the ground.

A lot of ideas sound like good ideas until you consider what it takes to make it happen, and what the impact will actually be.

Drill into the business decision.

An analogy is running a cost down – such as estimating the developer cost of a work item.   This is how you get clarity, know the trade-offs, and get a better handle on the work involved.

A simple way to test somebody’s decision is ask them, “Would you bet your job on it?”

25. Go up to the balcony.

You always think you have more power than you do.  Go up to the balcony.  Get a new vantage point.

Take a vertical slice of the problem and reflect on what’s at stake, who has interests, and who has the power.

26. Distinguish between adaptive and technical challenges.

When you’re up against a challenge in the system, first figure out whether it’s an adaptive challenge or a technical challenge.

The most common mistake leaders make is to treat an adaptive challenge like a technical challenge.

A technical challenge means you can apply your current know-how and authorities can do the work.

In an adaptive challenge means you have to learn new ways, and the people with the problem do the work.  If you recognize an adaptive challenge, you can slow down and read the situation.

This will help you see where things are stuck and where the real levers are.

27. Give them something they can react to.

It’s hard for people to react to a blank slate. When you lead, you often have to create the strawman for people to react to.

28. The Baby’s ugly.

When somebody has an idea, it’s their baby.  You might have feedback for their idea.

However, what you might think is feedback, might come across like you’re calling their baby ugly.

29. Managers clear the path for team.

Leaders find the path through the jungle.   Managers clear the path for the team.

It’s about enabling, empowering, and optimizing.

30. It isn’t personal; it’s business.

When you get run over by the system or caught up in politics, remind yourself that it’s not about you.  Attacks can often seem personal, but it’s part of the game.

Just like in soccer, people go after the person with the ball.  It’s not personal; it’s about getting the ball.

If you separate yourself from the situation, then you can better think about the plays and the motivations that are really driving the situation.

31. Balance connection and conviction.

Don’t tip the scales too much to one side or the other.  Balance your conviction for making things happen, with connection to the people around you.

When you’re conviction is out of balance, you make things happen while burning bridges, making enemies, and leaving dead bodies.

When your connection is out of balance, you try to make everybody happy and you lose yourself and your way in the process – and you end up not making anybody happy.

32. Shipping is a team sport.

It’s not about shipping through heroic efforts.  It’s about playing well with others.

Effective teamwork is a part of the process by design.

33. When people know the frame, they self-correct.

Focus on the goals and feedback loops.  When people know what success looks like, and they get effective feedback, they can self-correct.

The anti-pattern is to micro-manage and get in people’s business, instead of set the frame and get out of the way.

Part of an effective frame is co-creating goals so that people buy in.  When they don’t buy in, they vote with their feet, and go somewhere else, or they drag their feet and slow everything down.

What you really want is people racing to the finish line, because they can see the end-in-mind.  This is how amazing results happen.

34. If you set the frame, you win.

People tend to operate against a frame, whether it’s explicit or not.  In any system, if you get to set the frame, this is like setting the rules.

It’s carving out what’s in the frame, and what’s not, as well as what the outcomes are.

When you set this frame, and people buy into this frame, you win.  You’ve basically created the end-in-mind.  The rest is execution and implementation details.

35. Productize, then commoditize.

Productize first.  The market will naturally drive things towards a commodity, as more competition enters the market and it’s easier to reproduce without any qualitative difference.

36. Make a good decision quickly, or the next one will be free.

Moving up the stack means making effective decisions and using good judgment.

If you can’t make decisions, they’ll be made for you.

37. Focus on empowerment and accountability over making people happy.

Happy will be a by-product.  Chasing happy is a slippery slope.

38. Two things get in the way of progress.

There are two things that commonly get in the way of progress:  charters (who owns what) and business models.

39. Don’t react.

When something unexpected happens, don’t react.  Think it through so you can respond.

Respond over react.

This is especially true in re-orgs where the natural reaction might be to just react.

40. Three ways to look.

There are 3 ways to look at any situation.  You can see it as a do-over, a challenge (change and adapt), or a leadership opportunity (lead through ambiguity.)

41. With the org, because of the org, or despite the org.

When you get something done at a corporation, you can think about whether it was with the org, because of the org, or despite the org.

You can use this same check for a team, too.  Was it with the team, because of the team, or despite the team?

This helps you get clarity on whether the org or team is enabling or crippling.

42. There’s no wood behind the arrow.

This is about backing things up with real action or real results or real impact.

Those 42 lessons from Mike have served me well.   But I’d like to share a few more nuggets of wisdom from Mike that have also helped me in a number of situations, and have helped me shape my leadership philosophy and approach.

Maximize Your Strength Quotient

Build teams to maximize strength quotient.  You do this by first discovering your strengths, and then surrounding yourself with strengths that create a whole greater than the sum of the parts.

That’s where the magic happens.  For example, you mind round out a team of strengths to cover some important bases:

  1. ship / deliver (execution makes life easier)
  2. customer focused
  3. strategically sound
  4. detail and business orientation
  5. tell your story (internal and external communication)

I saw first-hand how the collective team was a powerful combination for strategy, results, and impact.

Managing Up

When it comes to managing up, Mike has two simple rules that have served me well:

  1. Speak in their language.  If you don’t speak in their terms or bridge, they’ll just tune you out.
  2. Think about what their job is trying to accomplish.  How is what you’re doing relate to why they care and what’s keeping them up at night

While they are simple rules, they are very effective.   They are both great reminders to map the value of what you’re doing back up the chain, and be able to articulate the value in a way that makes sense to key decision makers.

Guiding questions for Choosing Jobs

Mike uses a very simple set of guiding questions to evaluate a job.  I’ve used these time and again as a guide for myself and a guide for others:

  1. What problem do I get to work on? For example, needs to be hard, challenging, and attract killer talent.
  2. Who do I get to work with? For example, surround yourself with smart, capable, and amazing learning machines
  3. What impact do I get to have? For example, you might set your bar on world-wide impact.  This is easy to say… but harder to do and find.
  4. Do I trust who I work for? For example, do you really trust them?  This is the “Who’s got your back?” test.

Going from Vision to Results

Vision is how you keep your course.  Mike sticks to the basics and focuses on first getting clarity on the following:

  1. how to get there (the map or path and how to chunk it down)
  2. execution plans
  3. accountability

Framing and Storytelling to Execs

Mike shared some very pragmatic guidelines for effective storytelling with execs:

  1. They get it. In fact, not only do they get it, but they tell the story to others.
  2. Emotional connection.  It has durability at the emotional level (life changing)  The caveat is to be careful about creating an emotional response.
  3. Keep it simple.  The key here is to think about who you are talking to.  For example, you can use metaphors to quickly paint ideas or relate information.
  4. Jump to instances.  Light up abstractions with concrete examples and instances (for instance, blah, blah, blah.)

As you can see, Mike is a wealth of wisdom and I continue to learn all that I can from him.

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  1. Overwhelming!!
    If I’d need to choose my three from the list this is what I’d pick:
    – respond vs. react.
    – win the heart, the mind follows.
    – what are you about.

    and i love the frame for choosing jobs… a lot.

  2. Wow! That’s quite a mindful of wisdom. it restores my faith in employment to know that there are excellent mentors like Mike on the job. I especially appreciate these:
    “Would you bet your job on it?”
    When people know the frame, they self-correct.
    Balance connection and conviction.

  3. You were really inspired by your mentor. I Mike was proud to read this.

    My favorite part of this article were:

    – ask betters questions (This used to be a weakness of mine, but now it’s come close to a superpower)
    – creating a sense of urgency (I’ve been learning to apply this to more of my projects)
    – Know your weaknesses (I used to believe that I could level up my weaknesses. Oh what a mistake. Now I work with my strengths 80% of the time. So much more productive.)

  4. DWYSYWD – I like this lesson. The fact that it’s acronym is a palindrome yet the lesson seems to be about having a mirror between one’s words and action so they line up rings so true for me.

  5. JD
    When I read this post, I do not feel so alone…I feel empowered, I just can not do all these things very fast…I have to learn them on the one person show stage….

    I do not know what flip the bozo means? Is it crucial to my future success?

  6. These are powerful, but without the awareness of ourselves we cannot make any real change. Without being mindful of who we are and our propensities we’ll not see where we are going. 🙂

  7. @ Alik — I was talking with Mike today about the power of one-liner lessons … so many of these are sticky. I find myself using a lot of them on a regular basis — little stratagems of insight and action.

    @ Tom — Some people really know how to share their insight in a way that hits home. It’s people that Mike that really do make work a journey of excellence over just doing a job.

    @ Karl — I showed it to him today and he was surprised I was able to hone in on so many of the nuggets.

    @ JB — I used to take it for granted that everybody just does what they say they will do, but now I see why it’s such a crucial trait of a leader. It would be hard to follow a leader that says one thing, but does another 😉

    @ Patricia — We get by with a little help from our friends.

    Flipping the bozo bit simply means that you lost credibility with somebody and that it can be tough to get it back.

    @ Walter — I think that’s an important component of growth — knowing ourselves enough to know where to grow ourselves with skill.

  8. There’s a tremendous amount of wisdom that you have garnered, indicating both a great mentor and a great mentoree! I find your blog unique among the sea of self-development blogs. I appreciate your guiding principles and what you are trying to accomplish here is excellent. Here’s to more sources of insight!

  9. @ Sandra — Thank you! What I like is that Mike is in the game. His lessons come with scrapes and bruises and he can play the role of warrior, king, or sage.

  10. JD,
    What a GREAT guy to be around!!!

    I especially am connecting with the “win their hearts, the minds will follow” message. If we can really get that – get their heart into something – the investment is so much more meaningful. (and something I can sometimes let slip – so a good reminder, also…)

  11. @ Lance — You said it! One of Mike’s super skills is getting people fired up — challenging them to test their limits. Really, it’s the sports coach in him helping people play their best game at work.

  12. Hi JD .. the power of now #1 .. yes I know we are spurred on – so develop that sense of urgency. How true #2 & #3 are .. the impact will link with the heart .. and you’ll achieve more happily. Love the way you put these … the snowball effect, and start small dream big …

    The decision .. ‘would you bet your job on it’ .. you have to know what you’re doing and be totally confident that you’re in the right place, with the right product .. daunting, but right. Speaking in their language .. to me is so necessary in all walks of life and situations .. and giving them something to value and be passionate within their job, which is why they’re working with you in the first place – we all have aspirations at work ..

    It’s fascinating how important story telling is .. we do relate to stories and remember them .. Yes – I can see how you’ve learnt so much from Mike – what a wonderful position to be in .. and thanks for sharing here with us .. it’s great to read about &have as an ongoing resources … Have a good rest of the week – Hilary

  13. @ Hilary — When I first started meeting with Mike, I knew the gems of insight would build on each other, and sure enough they did. It’s like a constellation of wisdom. Mike’s way of wording things helped me really internalize the insights and I draw from them regularly. It’s like those moments of choice, then I hear Obi-Wan’s voice and make a better move. Mike is actually a great storyteller and I still need to build my skills here. Thank you!

  14. I sent this over for my hubby to read. The sense of urgency are my household words. Excellent and in such detail. I like your 3 lessons best…but the 42 go into such depth for more work for all of us!

  15. @ Farnoosh — A sense of urgency sets a tone and pace that what you’re doing matters. The irony is that when you feel what you do matters, it actually does.

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