Why Asking Great Questions is Key to an Effective Plan
LisaMarie • May 20, 2019
“Someone’s sitting in the shade today because someone planted a tree a long time ago.” — Warren Buffet
The 1st pillar in my 7 Pillars of Leadership is: Great leaders – or leaders worth following – start with a written plan.
To create an effective plan, they understand the importance of asking great questions and making asks of others on the journey.
How many times have you stopped yourself from pursuing what you want because you asked the wrong question?
Or, worse yet, you held back and didn’t ask the question you wanted to ask?
To fully understand any situation, you’ve got to become incredibly well-versed in the art of asking great questions.
When I’m stuck and don’t know what question to ask, I simply invite the person to “Tell me more about that…”
This allows me to more completely assess a situation, especially when I’m going to make an ask.
Asking for what you want can feel more risky (and scary for some people) than asking great questions.
You have to build your foundation, understand your value, and have a clear sense of “why” your mission is important.
You also have to be able to speak it in a manner that has others want to listen and lean in to your request.
If you’re serious about what you want, you can’t sit around and hope others will telepathically understand what you want and then give it to you.
To get to the end you have in mind requires risk – and seeing that desired outcome is the 1st step in “The 5 Steps to an Effective Plan” taught at my annual Design Your Destiny Live 3-day leadership conference.
If a person doesn’t agree to what I’m asking for – or gives me an outright “no”, my mind is actively thinking about how I can still move in the direction of my vision.
Similarly, Pam Johnson, outdoor education expert and my long-time client, grew up with the belief that “No means yes.” Pam shares that this mindset about “no” developed because if her Dad didn’t say “yes” to something, she mind-mapped that it wasn’t a closed door, it was an opportunity to find another option or door to be opened.
This form of critical thinking has become her success habit which many people in the Upside Thinking and Destiny Designers community have benefitted from in their own decision making processes.
Great outcomes come from great plans.
Great plans come from great questions.
Both visionary and inquiry require courage, creativity and perseverance… the same qualities of great leaders.
Action:
The Upside Challenge of the week is to sit down and think about your own written plan for getting what you want. Is it clear? Is it mapped out? How good are you at asking great questions? Asking for what you want?
The world needs you and your brilliance.
By Lisa Marie Platske
•
January 19, 2026
By Lisa Marie Platske
•
January 12, 2026
No matter how happy someone may seem, they have moments when they question if they can go on. And no matter how strong someone may appear, they have days when they feel like they're falling apart. That's one of the most confusing aspects of leadership. See, most leaders feel that because they're the one at the helm steering the ship, they should have it together and be "on" 24x7. And that's unrealistic. Yet that belief has caused many leaders to sink their ship because of the inability to reach out and ask for help. No one can go it alone. Every leader needs someone to lean on. Phrases like "Only the strong survive." and "You gotta just 'man' up." do more damage than good. I learned this when I was working in Federal law enforcement and 9/11 hit. The superhuman requests to work hours that pushed the body to the limits were a recipe for certain disaster. Men and women who may have needed someone to talk to themselves to process their grief were thrust into the grim reality that they were needed more than ever—and needed to be stronger than they knew how to do. One of the NYPD beat cops that I had befriended was in the middle of a shift when he had a full-blown meltdown on 5th Avenue in New York City six months after 9/11. The walk of leadership never has been—and never will be—a solo affair. You need other folks around you that you can trust and rely on in good times and not-so-good times. And I'm not talking about a friend, spouse, or family member. I'm talking about a trusted advisor with whom you can turn matter what is working or on fire. Because every leader deserves a space to be real, to be guided, and to be reminded of the truth of who they are . The kind of space I’ve devoted my life to creating for those called to lead from purpose. And when leaders have that kind of support, the moments that once felt too heavy begin to make sense. They find the strength to keep going because they’re no longer doing it on their own. ACTION: The Upside Challenge for the week is to think and name one person who you can turn to when leadership feels heavy. Reach out to one of them this week. Tell the truth about where you are. Because even leaders need a place to lean.
By Lisa Marie Platske
•
January 5, 2026
As I look at how to move forward with a new year...I’m tasked with identifying what to do to take action in the here and now. It sometimes feels hard... which is why I’m grateful for friends who lend a listening ear. It feels as if no matter how much I wipe the surface of my white board, my old writing shows through. Leaders face this challenge all the time. ~ How to erase what’s holding them back... ... and how to embrace what will propel them forward without old stories seeping through. I believe that’s why this time of year is confronting for people. They’re faced with the dilemma of honestly facing whether they’ve taken action on what they said they wanted last year ... and looking at how much energy and effort they put into their commitments... while assessing what's still flippin' gettin' in the way. Some people run and hide – and then lie to themselves. Others play the blame game. Only the courageous take personal responsibility for their shortcomings... with renewed energy to do better moving forward. To do this, you’ve got to get curious. Looking at where you’re at in this moment will determine how successful you will be tomorrow. And, you can’t get to self-regulation without self-awareness so that’s also critical. You’re born with a certain success set point and tolerance for risk... ... as well as a boatload of behavioral characteristics... ... some which serve you and others that get in the way of your success. Over time, you can make adjustments or choose to step into old habits. Blind spots are places we just can’t see on our own. Upside Leaders was born out of my desire to walk alongside leaders in this very space... where the unseen becomes visible, and small, intentional shifts create lasting transformation. When I spoke with a friend, he said perhaps it's just allowing for a small shift to the left or right, rather than an uncovering. For me that 1% tilt has made all the difference... ... especially when I look through that lens with humility... ... which precedes personal and professional growth. You cannot improve where you’re headed unless you improve yourself. See this as a time to erase what is no longer relevant... put some effort into making sure the old writing on your "white board" doesn't seep through. You are writing a new story. ... look in the mirror... ... and commit to doing better. ACTION: The Upside Challenge for the week is to look at your current goals and circle the one that feels the most familiar. Challenge yourself to reimagine it and to stretch it by 1%. Ask, “ What would this look like if I led with full conviction instead of comfort? ” Then pause and listen for what you’re being asked to release so greater vision can unfold through you.
By Lisa Marie Platske
•
December 29, 2025
Most folks are introverts at heart. They prefer to hole up and live inside their cave vs. venturing out to try something new. And most folks have a lot of excuses when you invite them to experience something that will require them to stretch their growth edges. ~ "I don't like to travel." ~ "Traveling is hard." ~ "I can't be away from my family." ~ "My business can't run without me." ~ "It's too much money." The thing is ... you've got to escape your cave—and be with other people. This isn't optional. It's how your ideas and path gets challenged in ways that are easier than finding out you're one decision from going out of business because you didn't see that train coming. When you do choose to connect with other folks, it's important that you're choosy with who you give your precious time to and where. That means if you go someplace that's free or cheap, that's likely the depth of the conversations you'll have. I get invited to lots of seminars, mastermind groups, and peer networking circles. Most of the invites are for me to come for free because having me in the room is valuable. I turn most of them down and go to the events that cost money. Why? Because there are TONS of free or cheap places to go to hang out with others in business ... and if that's where you spend your time and energy, you'll be stuck in the same place 5 years from now. When you come to an Upside Thinking event, you notice the folks around you are a little different. So if you're not showing up at least once a year at an Upside Thinking event, you're missing out on something important. Personally, I go to about 5 meetings a year where I seek to NOT be the smartest person in the room, actively inviting folks to challenge everything I'm saying. You should do the same. ACTION: The Upside Challenge for the week is to commit to attending at least one high-caliber event in the next twelve months where the investment of time, travel, and money feels like a stretch. Choose a room where you expect to be challenged, not affirmed, and where the conversations push you to see blind spots you didn’t know you had. Put it on your calendar now so it’s a non-negotiable.
By Lisa Marie Platske
•
January 19, 2026
By Lisa Marie Platske
•
January 12, 2026
No matter how happy someone may seem, they have moments when they question if they can go on. And no matter how strong someone may appear, they have days when they feel like they're falling apart. That's one of the most confusing aspects of leadership. See, most leaders feel that because they're the one at the helm steering the ship, they should have it together and be "on" 24x7. And that's unrealistic. Yet that belief has caused many leaders to sink their ship because of the inability to reach out and ask for help. No one can go it alone. Every leader needs someone to lean on. Phrases like "Only the strong survive." and "You gotta just 'man' up." do more damage than good. I learned this when I was working in Federal law enforcement and 9/11 hit. The superhuman requests to work hours that pushed the body to the limits were a recipe for certain disaster. Men and women who may have needed someone to talk to themselves to process their grief were thrust into the grim reality that they were needed more than ever—and needed to be stronger than they knew how to do. One of the NYPD beat cops that I had befriended was in the middle of a shift when he had a full-blown meltdown on 5th Avenue in New York City six months after 9/11. The walk of leadership never has been—and never will be—a solo affair. You need other folks around you that you can trust and rely on in good times and not-so-good times. And I'm not talking about a friend, spouse, or family member. I'm talking about a trusted advisor with whom you can turn matter what is working or on fire. Because every leader deserves a space to be real, to be guided, and to be reminded of the truth of who they are . The kind of space I’ve devoted my life to creating for those called to lead from purpose. And when leaders have that kind of support, the moments that once felt too heavy begin to make sense. They find the strength to keep going because they’re no longer doing it on their own. ACTION: The Upside Challenge for the week is to think and name one person who you can turn to when leadership feels heavy. Reach out to one of them this week. Tell the truth about where you are. Because even leaders need a place to lean.
By Lisa Marie Platske
•
January 5, 2026
As I look at how to move forward with a new year...I’m tasked with identifying what to do to take action in the here and now. It sometimes feels hard... which is why I’m grateful for friends who lend a listening ear. It feels as if no matter how much I wipe the surface of my white board, my old writing shows through. Leaders face this challenge all the time. ~ How to erase what’s holding them back... ... and how to embrace what will propel them forward without old stories seeping through. I believe that’s why this time of year is confronting for people. They’re faced with the dilemma of honestly facing whether they’ve taken action on what they said they wanted last year ... and looking at how much energy and effort they put into their commitments... while assessing what's still flippin' gettin' in the way. Some people run and hide – and then lie to themselves. Others play the blame game. Only the courageous take personal responsibility for their shortcomings... with renewed energy to do better moving forward. To do this, you’ve got to get curious. Looking at where you’re at in this moment will determine how successful you will be tomorrow. And, you can’t get to self-regulation without self-awareness so that’s also critical. You’re born with a certain success set point and tolerance for risk... ... as well as a boatload of behavioral characteristics... ... some which serve you and others that get in the way of your success. Over time, you can make adjustments or choose to step into old habits. Blind spots are places we just can’t see on our own. Upside Leaders was born out of my desire to walk alongside leaders in this very space... where the unseen becomes visible, and small, intentional shifts create lasting transformation. When I spoke with a friend, he said perhaps it's just allowing for a small shift to the left or right, rather than an uncovering. For me that 1% tilt has made all the difference... ... especially when I look through that lens with humility... ... which precedes personal and professional growth. You cannot improve where you’re headed unless you improve yourself. See this as a time to erase what is no longer relevant... put some effort into making sure the old writing on your "white board" doesn't seep through. You are writing a new story. ... look in the mirror... ... and commit to doing better. ACTION: The Upside Challenge for the week is to look at your current goals and circle the one that feels the most familiar. Challenge yourself to reimagine it and to stretch it by 1%. Ask, “ What would this look like if I led with full conviction instead of comfort? ” Then pause and listen for what you’re being asked to release so greater vision can unfold through you.
By Lisa Marie Platske
•
December 29, 2025
Most folks are introverts at heart. They prefer to hole up and live inside their cave vs. venturing out to try something new. And most folks have a lot of excuses when you invite them to experience something that will require them to stretch their growth edges. ~ "I don't like to travel." ~ "Traveling is hard." ~ "I can't be away from my family." ~ "My business can't run without me." ~ "It's too much money." The thing is ... you've got to escape your cave—and be with other people. This isn't optional. It's how your ideas and path gets challenged in ways that are easier than finding out you're one decision from going out of business because you didn't see that train coming. When you do choose to connect with other folks, it's important that you're choosy with who you give your precious time to and where. That means if you go someplace that's free or cheap, that's likely the depth of the conversations you'll have. I get invited to lots of seminars, mastermind groups, and peer networking circles. Most of the invites are for me to come for free because having me in the room is valuable. I turn most of them down and go to the events that cost money. Why? Because there are TONS of free or cheap places to go to hang out with others in business ... and if that's where you spend your time and energy, you'll be stuck in the same place 5 years from now. When you come to an Upside Thinking event, you notice the folks around you are a little different. So if you're not showing up at least once a year at an Upside Thinking event, you're missing out on something important. Personally, I go to about 5 meetings a year where I seek to NOT be the smartest person in the room, actively inviting folks to challenge everything I'm saying. You should do the same. ACTION: The Upside Challenge for the week is to commit to attending at least one high-caliber event in the next twelve months where the investment of time, travel, and money feels like a stretch. Choose a room where you expect to be challenged, not affirmed, and where the conversations push you to see blind spots you didn’t know you had. Put it on your calendar now so it’s a non-negotiable.
