Starting the conversation…

How important is it to ask for what you want, and what we have to do to speak up when it really matters?

Host: Jess Dewell
Guest: Nathalie Gregg

What You Will Hear:

Be fearless in what you want.

Own our fearlessness (even when we aren’t in the mood).

Our tribe matters.

Take action – follow your steps to ask for what you want – especially on days where we aren’t getting it.

Reasons we tend to hold back and not ask for what we want.

It’s how we recover from failure that tells us the most.

How to we build a fierce asking muscle. How to practice letting stuff go.

Collaboration and synergy can be facilitated with the integration of several soft skills.

A story of asking for what we want.

Audience Question: When we talk about triggers, that sounds like manipulation to me, maybe I’m wrong, I’d like to hear more

Audience Question: How do I find my trigger?

It’s ok to feel selfish sometimes, don’t let it be a limiting belief.

Synthesize all points of learning.

New ways to learn.

How to get to where we want to go.

Audience Question: What happens if we can’t find a mentor, where should I look for?

What makes it BOLD to ask for what you want?

Notable and Quotable:


Jess Dewell 6:23
We’re not good at a skill that we’re good at overall, all of the time.

Jess Dewell 7:18
Regardless of our skill set, and how strong those skills are, there are still times that we don’t feel as confident in them. We don’t use them to their fullest capability for whatever reason.

Nathalie Gregg 7:44
I believe in affirmation. I say them continuously. And I am so grateful that I have a tribe of advisors, and also the trusted collegues that continue to encourage me, pick me up and cheer me on.

Jess Dewell 9:49
Right? Our tribe can come from anywhere,

Jess Dewell 10:04
How amazing the continuous to go back, to go back, to go back, to go back. And I feel like that’s a similar process of this concept of an ask. I think it could be for getting something done. I also think it could be for thinking.

Nathalie Gregg 10:46
Amazing what can go on in your head when you actually sit down to think, and when you actually do the process of basically getting away from the noise, and really getting focused in on what you want to accomplish. It’s amazing what things happen at that time.

Nathalie Gregg 11:36
But I think a lot of times that we don’t ask, because we fear that we’re not going to get what we’re looking for. Or we fear that it’s going to be rejection. Or we feel like that the person is going to judge us and say why she asked for that she, knows she’s not confident enough half of that. So I think there’s so many that goes on, you know, between our ears that make us a little hesitant about making the ask, but once you actually do it, then I think it becomes easier. It’s like exercise, it becomes easier the more you do it,

Nathalie Gregg 13:17
We beat ourselves up because we’re not the same every day. Some days were extremely disciplined. And then some days we’re like, okay, who is this person?

Nathalie Gregg 13:35
We need to focus on the days when we’re in flow, and we’re really in that space that we really focus on the things that we need to get done right then and there. And the days that we aren’t, give ourselves some grace.

Jess Dewell 14:11
When your skills roughly match your challenges, you go into a flow state.

Nathalie Gregg 14:28
A lot of times we overthink things, and it’s the simplicity of things that actually help us I think a lot of times to stay in the flow. Because we tend to overcomplicate things, I know that I do. It’s amazing with the things that I can come up with. In my mind.

Nathalie Gregg 16:19
We fail greatly all day long. And sometimes it’s the public failures that we see most. We just have to know failure’s part of leadership. Failure is part of growth. And understanding that when we fail, not if we fail, it’s when we fail, how do we recover? What’s our recovery plan?


Jess Dewell 17:39
Part of this fierceness and this grace, is to let the things go. To own them. To show up and say them, and then to let them go.

Jess Dewell 17:48
Sometimes there’s no good way, there’s not a tactful way to say, wow I messed up. So we just kind of have to do that blurt thing Hey, blurr blurr. And however it comes out, it comes out. Because when we have the right intention, things tend to work out, even if they’re a little bumpy along the way. It’s still the shortest path,

Jess Dewell 18:41
We need to put a stake in the ground to know where we’re going. We also need to go. well what’s actually tied to the state we put into the ground? The kite at the end of the line versus the cloud that’s going to keep going. Which is the kite and which is the cloud?

Jess Dewell 19:38
When we know what we’re working on, and when it lines up with the skills that we have, we tend to go into this flow state, and things can go incredibly fast. And that ability to let go, or discern what is attached to our stake in the sand and what it’s not, makes a big difference, because you do it for ourselves. Now we can model it for the team that we are a part of. The collaboration that we have in our workplace as well.

Jess Dewell 21:07
There’s a vulnerability that shows up. We can’t be fierce unless we know how to be vulnerable

Nathalie Gregg 21:31
Meditation, affirmation, that puts me in a place where it doesn’t allow my brain to take over. That it puts me in a more creative place, to where I can listen, to where I’m open to information coming in, as well as open the conversations. And I really think that it helps me dissolve the barriers that I have up most of the time.

Jess Dewell 23:06
It’s all about cooperation. It’s all about the energy of the people that are showing up together, for some sort of a common goal, that everybody has agreed upon.

Nathalie Gregg 26:13
And it’s important to know which member has what trigger. And there’s going to be, you know, accountability, even with accountability triggers, people with responsibility, trainers, but you know, so as a person that leading the team or as a manager of a team, it’s important to know, who has what trigger and also how does that trigger show up. For instance, you know, you have some people on the team, you just tell them a goal and leave them alone, they out of their way. And then other sometimes you have to encourage to do so and so, you know, this is due tomorrow, and this is what we need to look at a we can make sure that this happened. So the everybody is on the team, but you have to know the triggers and actually what excites them that will get them to the expected outcome.They were about 350 women there.

Nathalie Gregg 30:07
I’m always researching and taking polls. And I asked, “Has anyone asked asked you to mentor them?” And they said “no.” And so I waited about a week later, then I called a couple more participants, and I asked them I said, has anyone asked you mentor them? And they said, “no.” And I was really disheartened because I was like all of these amazing women in one room and no one has asked for mentorship. So I’m like, okay, that’s another conversation around the power of the fearless ask.I don’t know if a lot of people know what having a mentor me will you describe in your words, what it means

Nathalie Gregg 31:06
Mentorship means someone who’s there to guide, encourage, motivate and sometimes carry.

Nathalie Gregg 34:22
All of us are wired in several different ways. My trigger is, “Is it meaningful? Is it going to mean something to me, if I do this project or if I do this work?”

Jess Dewell 35:41
The trigger is, what makes us go? What makes us turn into the Energizer Bunny? What makes us want to be fierce to make change, which is a positive.

Jess Dewell 38:12
Thinking we’re selfish when we go for an ask is a limiting belief.

Nathalie Gregg 38:29
It’s only selfish if we don’t share it. If we don’t share our talent, if we don’t share ideas. It’s really selfish if we just keep it to ourselves, and we don’t share.

Jess Dewell 39:50
The behaviors and the results of those behaviors, what happens when we take action? And how do we take it action and make it more purposeful as we go through? And somebody who is already doing that and does a well, they might want to do the opposite, or attempt to do the opposite, to get more context to learn more.

Nathalie Gregg 44:03
And so you have time, whether it’s 15 minutes in the morning, whether the 15 minutes at lunch, whether 15 minutes in the afternoon. So you would be amazed at what the power of 15 minutes can actually do for your learning, and also for you being able to attain your goals.

Jess Dewell 44:39
There’s a fear of asking of others. I think there’s a bigger fear of asking of ourselves, Deciding what’s to say no to, because when we say yes to something, we’re saying no to something else, and recognizing are we saying no to our priorities,

Nathalie Gregg 44:55
Go find someone who’s doing something that you would like to enjoy doing, or someone who’s two or three or four steps ahead of you in those areas that you’d like to have improvement. And make the ask. And if the first person says no, no problem. Because I always say, sometime you need to kiss a lot of frogs to get to the prince.

Nathalie Gregg 47:21
They are people that are willing to mentor you, but most of them have never been asked. That the sad part about it. All these people that have all these gifts, and talents, and abilities to do all these amazing things. But no one has asked them to mentor them, whether it’s informal or formal.

Nathalie Gregg 48:52
Thank you so much for this opportunity to have this courageous conversation with you today. I am so excited about what you’re doing, the whole business radio, I’m sleeping out of my seat. I want to encourage everyone to go out there and to be so confident and feel it, because if you have the intention and you asked for it, the sky’s the limit.



confidence, mindset, behavior, discipline, simplicity, priorities, intention

It’s important to ask for what you want; equally essential is what we have to do to speak up when something really matters. 

How do we know when to speak up and not back down to get what we want? Socially acceptable behavior, tactfulness, and even proactivity are just some of the pieces we need to get what we want every time. To “cut to the chase and just ask already,” Jess Dewell talks with Nathalie Gregg, change agent, organizational developer, adjunct professor, public speaker, published writer, and television personality.

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