Self-Aware Leadership: The Art of the Ask
- Marissa Krupa
- Jun 25
- 11 min read
Many leadership gurus are now speaking about "self-aware leadership". Self-aware leadership means a person is aware of their own strengths, weaknesses, and emotions, but more importantly, how that combination impacts others. Self-aware leaders, then use this knowledge to guide how they communicate, interact, and execute.
Here's an example: Fiona knows that she operates best in the morning when it comes to team management and decision-making, yet, not everyone on her team is a "morning person". So, she schedules the team meetings right before lunch, and sometimes makes the team meeting a "lunch" meeting. This way she can still perform at her best before the afternoon drowsy period, but also not too early for those who only may be getting their brains turned on after a two hours of coffee. She polled the team to see what they thought of this arrangement, and although not everyone is 100% keen on it, most everyone agrees it's been the best way to meet everyone's brain needs. The meetings are often lively and people are eager to make decisions and "get things done" because they want to get to lunch.
How did Fiona arrive at this workable arrangement for herself and her team?
She asked.

Why is asking an important tool for self-aware leaders?
Asking puts you into listening mode.
Hearing another's perspective allows your perspective to widen.
You can learn others' needs and how they best operate/function.
But, like all communication strategies, asking is an art form. Asking bluntly, or with sarcasm, or with accusations, is not a helpful strategy.
The key to make any tool successful is the mindset you bring to it. One of the trauma-informed classroom strategies I learned as an educator was instead of asking "What's wrong with you?" to a student who is acting out, try asking "What happened to you?" or "What's going on for you right now?"
Even with the shift in words, though, it's critical to bring curiosity into the tone and delivery of the question. "What's going on for your right now?" could sound like an attack if it's said with an accusatory tone.
On David R Hawkins' "Map of Consciousness", which he explained in his seminal book Power vs Force, the first level in the higher energy vibrations is Courage, and the emotion associated with it is Affirmation. The level above that is Neutrality with the emotion Trust. Hawkins does not specifically label curiosity on the map, but it is a type of affirmation. When you've been curious about something in the past, hasn't it been a type of affirmation for "what is" and a desire to know more of "what is" (the what is that you don't know) about that thing? And, don't you also have trust that you'll find the answer?
For example, let's say a child is curious about an insect, and starts to play with it. They will quickly find out the answer of whether it bites, flies, stings, or oozes a fluid if squished. In this way, curiosity brings us into a "child-like" mind that is open and receptive. And, gaining more knowledge is a great way for leaders to become more aware of themselves and others.
Asking is also a great way to speak up for what you need without seeming like you are making demands or being insistent. It's a wonderful way to express authority or influence over others, without coming across as controlling. Adults in the workplace are adults, and should be treated as such. That means they don't want to be told what to do like children, because that wipes out their sense of autonomy. Check out this example. Which one sounds more appealing to you?
"Hey ____! Please email me the ticket I paid for. I want to print it out. It will be much easier than trying to hunt everyone down beforehand. Thanks!"
OR
"Hey ___! Will you please email me the ticket that I paid for? I want to print it out. It will be much easier than trying to hunt everyone down beforehand. Thanks!
OR
"Hey___! I was thinking about the upcoming concert you bought tickets for. It might be hectic to meet up beforehand. Could you forward on the ticket I paid for, so I can go in separately in case we need to? Thanks!"
All three essentially say the same thing. But, which one feels better to you? Likely the last one, right? Even though the second example also includes a question, what makes it not quite as good as the third one? The words "will you please" versus "could you". "Will you please" sounds much more demanding than "could you", doesn't it? And, the last example still includes a connection. There's an assumption that the friends will still go into the concert together, but "just in case", they now have their own tickets. The other two imply that they cannot be bothered to meet up beforehand, and so want to go in alone.
This example highlights how subtle communication with asking can get. Especially in an email, the difference could mean keeping or losing your job. I've been reprimanded for email communications that are much lighter than even this! It's really easy for a person to get their feathers ruffled, especially these days when most workers are extremely overworked, stressed out, underslept, and the like.

The thing about asking is it taps into our innate desire to help others. This is a character trait most humans have. Asking gives everyone a choice, but it also helps people lean more towards "yes" because they want to help you. Helping others feels good, and it stimulates positive brain endorphins. Many volunteers will tell you they feel very satisfied with their volunteering work, even alongside a paid worker at the same organization who feels miserable. It's because the volunteer is helping another with their time and energy, and they feel that difference.
And, another great aspect to asking also comes from the trauma-informed lens, which is giving the person who hears the question an opportunity to choose how to respond. Most of the time, if worded well, a person feels inclined to agree to what is being asked for. If the question is not worded well, it can come across as a demand, even with the best of intentions. Either way, when phrased in a question, the recipient still has a choice as to how and when to respond.
Offering choice is essential for a person to feel safe in any relationship. Being a self-aware leader in relationship development means helping those you are interacting with to feel safe, without sacrificing your own sense of safety. You can read more about how safe leaders create safe spaces here.
One final point, the frequency of how often you ask questions about a particular topic also matters as to the effectiveness of your ask. If you are a manager asking your team members about something that will impact the procedure of your meeting, try to ask for that information in plenty of time to collate the data for the next meeting. If your team meets every two weeks, try asking at least a week in advance. Give your team several days to respond before sending a follow-up. If people are feeling pressured or pestered to answer within a short window of time, they will be just as annoyed or decide to ignore the question as if you made a demand instead.
This also means being acutely aware of when to mark something "urgent". Self-aware leadership means understanding that not everything you think is urgent is also urgent for others. If your team doesn't know the "why" behind the urgency, then they still won't act with urgency no matter how you phrase the ask. And, if every other ask is "urgent", then like The Boy Who Cries Wolf, no one will believe you when the urgent matter does come to a head, and you'll be left with problems as well as destroyed credibility with your team.
If the art of asking is starting to feel overwhelming, don't worry. There are some simple things you can try to begin honing this skill.
Begin with asking yourself
How we work up the courage to ask things is by asking ourselves questions. Even in our own minds, we tend to tell ourselves what to do. When was the last time you asked yourself a question? Even something as easy as "What would you like for lunch?" Or did you simply say to yourself "I'm going to grab tacos for lunch." without thinking much more about it?
Self-awareness also comes from asking ourselves questions, so this is kind of a 2-for-1 awareness strategy!

Begin by asking yourself some things that could be easy to answer like "How does the temperature feel to me in my office?" or "Do I like the taste of my coffee right now?" or "What is your favorite lunchtime eatery, and why?"
Questions like these seem silly, but it begins to train our minds to become more curious about everything. It also softens our own self-talk, enabling our minds to develop a more compassionate mindset towards ourselves. It says a lot about a person's mindset when they tell themselves what to do all the time. Asking yourself questions helps to foster many things:
Getting into the present moment. Just in the moment of asking yourself the question, you have paused and become present.
Getting curious. Like mentioned above, a curious mind is one that affirms and trusts.
Getting clear. When we don't ask questions, we assume a lot, which can get us into trouble. Asking regularly creates the habit of seeking more information.
Try to just start by asking yourself a couple questions a day, and see how it goes. From there, you can begin to use questions as a tool for being present within your productivity. Here are a few to try on:
What is the next right thing to do in this moment?
What is the most urgent thing I need to tackle right now?
When is the next closest deadline I must meet?
After about a week or so, reflect on your question-asking habit. If it feels good, and you learn more about yourself, then begin by asking questions to others. Let's explore how in the next section.
Use "small" questions to practice with others
Just like we started with silly or innocuous questions with ourselves, now let's take those questions to others.
Whether you manage a team or are a team member, asking questions does a lot of positive things to help you build good working relationships:
You'll become known as someone who is generous and interesting rather than selfish
You'll learn so much about how your colleagues best "operate"
You'll learn how to best support your colleagues with exactly what they need

How to get started? Other than the usual faire of "do you have children" or "are you married" or whatever, which to some might be a little offensive because it doesn't fit in with their lifestyle, try some "smalltalk" questions like these:
"What's your favorite lunch place near here and what do you like about it?"
"How did you get interested in ____? What lead you to that hobby?"
"What are the things you like most about your role and this team? How come?"
This last one especially is great because 99% of people are expecting to be asked what they "hate" about their role or this team. It's a totally different vibe when someone asks what they like most. Watch their body language and the way in which they answer, just as much as listening to their answer. These signals will tell you a lot about their mindset and how they view the world. With this information, you can discern things like a) Do I want to align myself with them, fully? Or is the jury still out? b) With this type of mindset, what might be some challenges to working with them? and c) How can I make sure that my work with them will not be considered a threat, but rather, an invitation to collaborate?
It's amazing what a person can learn about others when they ask questions. Instead of jumping into a new work environment, asking questions and listening strategically can allow you to become intentional with your work behavior, instead of just reactionary. With a vision and goals list to strive for, your newfound knowledge from the questions you ask your colleagues can now become integrated into your strategic plan.
Pretty nifty, eh? :)
But, what if you're the team manager? Or vice president, or the like? Asking questions is a great way to keep your own growth mindset sharp, as well as learn better how to support your team. Let's explore more...
When in doubt, ask for more
Whether managing a team meeting or conducting a 1:1 session with a subordinate, it's never a bad idea to "ask for more", especially when they are taking the risk of sharing a new idea.
Let's pretend you're having a meeting with a team member, and they are sharing a new idea that seems pretty much insane, and very likely to fail. You could say something like "Let me get back to you on that." But, the subordinate will know that they are being blown off, and they'll be crushed. Thing is, anytime we hear a new idea, it's hard to get a hold of it sometimes. Try saying, "Tell me more." That's it. Just Tell Me More. See what they say. You might pick up on another layer or dimension of the idea that you hadn't heard previously because alarm bells were going off in your head that this idea was insane.
You can also get specific and say, "Tell me more about ____. How would it work?" Or, "How would it work with ____?"
This phrase is wonderful because you are not actually committing or agreeing with the person and their crazy idea. The phrase itself is neutral. Even so, most people will interpret it as interest, and they'll really get talking. Thing is, even the craziest of ideas has some validity, because you may hear a part of that crazy idea that is actually brilliant. If you didn't inquire, and ask for more, then you'd never hear that one small tiny brilliant thing that saved your company/made you a bajillion dollars/disrupted the market/etc.

In another blog, I wrote about how you can ask your team or individual contributor what they learned about something or a particular data point, or whatever. This is a nice 2-for-1 on growth mindset AND learning more about their style, desired career path, etc. It also helps create a sense of safety in the relationship, so really this type of ask is a "triple whammy"!
To expand beyond the one-on-ones, you could ask an individual or team, "What's your takeaway from that meeting?" Or "Did you have any 'ah-ha' moments from that client call?" These asks get the brains of your supervisees moving, thinking, processing, and then hopefully they'll share great insights for you to help with your management of them as a team, as well as the productivity of all of you.
Whether in an organization or running their own business, successful leaders act like the dumbest people in the room, and ask the most questions. This, in and of itself, is growth mindset. They take what they learn, and apply it in new and innovative ways, not only to help them learn how to "code switch" when interacting with various members of their team, but also how to support their team members in such a way that the best is brought out in them.
Yes, leaders are rewarded for their production and execution. But, they are also rewarded for their reputation. When a great leader helps their people to be their best, and shine in other areas of the company if they decide to move up the chain, they are hard not to notice. This reputation is not easily won. Yet, even more so, once it is lost, it is almost impossible to reclaim.
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Now, it's my turn to ask. What did you think of this blog? Was it useful to you? Would you recommend others read it? Why or why not? What do you wish was different about this blog? What did you like about this blog? What would you like to see in other blogs?
Ok, I'll stop there. :)
You don't have to answer any or all of these questions but I ask because I would like to know. Your opinion is valuable to me. Please share in the comments, or get in touch in the contact form at the bottom of the page.
If you don't ask, you don't get. Happy asking!
Marissa
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