‘Lead With Confidence’ An Interview With Leadership Coach Christina Holloway

Andrew Wayfinder Hryniewicz
11 min readJun 1, 2021

The Destiny Awakening Interviews is a podcast with Andrew Wayfinder and his guests.

Every week (sometimes more) we have a short focused interview with an expert, author, speaker designed to bring you powerful insights, inspiration and ways to break free, live life by your vision and values, and make a difference in our changing and challenging world.

Listen to the podcast at: https://www.andrewwayfinder.com/blog/DA0023

Andrew Hryniewicz

So hello everyone, and a very warm welcome to another edition of the Destiny Awakening Interviews.

I’m Andrew Wayfinder Hryniewicz and I’m joined today by Christina Holloway, leadership expert, consultant, and speaker.

And a very, very warm welcome to you, Christina. Where are you hanging out today?

Christina Holloway

Oh, thank you. I appreciate that. I’m just outside Chicago and enjoying the spring weather.

Andrew Hryniewicz

I guess it’s not minus 40 anymore or anything crazy like that.

Christina Holloway

It is not as it’s in the 60s, and the flowers are starting to pop out a little. So, it feels pretty good.

Andrew Hryniewicz

Great.

So, let’s get on to your work and your experience, which is really fascinating.

Christina Holloway is the founder of christinaholloway.com, where she helps professionals, entrepreneurs and executives become leaders, influencers and trailblazers in their field.

Christina has consulted for a wide range of clients including Accenture, PWC, Google, McDonald’s, Spotify, and more. She’s been named a top mentor coach at 1871, Chicago’s premier technology incubator. And the number one executive coach in Chicago, by Influence Digest.

She’s also been featured in Forbes magazine, Fast Company and the Huffington Post. And has spoken at the University of Chicago, Yale University and CFO Forward on leadership development.

A passionate champion of social change, Christina contributes a portion of her profits, to support Connections for Abused Women and Their Children, a nonprofit organization dedicated to awareness and prevention of domestic abuse.

Thank you, Christina, for your time today.

Christina Holloway

Thank you for having me.

Andrew Hryniewicz

And, the topic we’re going to be looking into, is “Leading with Confidence: How a Powerful Leadership Brand can take you from Excellence to Mastery.” Christina is going to unpack that idea by answering six questions.

The first question, Christina, who is your ideal client? and what’s the transformation your work helps them achieve?

Christina Holloway

So these days, if I were to look back at 2020, I’m looking at people who, quite profoundly, are affected by the changes in their work environment.

Either through work from home initiatives, or just being downsized, or laid off.

They’re finding that they now have to reevaluate what it means to be a person who shows up for work in changing times.

I typically work with people who work inside organizations. They’re trying to get promoted. They’re managers, senior managers, directors, trying to be promoted, even up to VP, the C suite.

And then, I also work, like you mentioned, with tech incubators.

So, I’ve spent time volunteering mentor hours to people who want to… they have an idea, an innovative idea… So they want to get out there, and they want to figure out what’s the quickest way for them to get visibility for their new innovative idea.

So, I’ve spent quite a few years working as a mentor coach for tech entrepreneurs.

And then, also people who, either run their own businesses that’s quite established. Or they’ve inherited a family run business, and they want to make it their own.

And then, like we mentioned, the people who are inside a company, who really want to know “What does it mean for me to be successful?”

But the underlying request that they have is, “Help me find my confidence.”

In 2020, where our confidence was chipped away. So, help me find my confidence…

“Help me understand what is my voice? What am I trying to do? Who am I impacting?”

And then, my bigger question: “Do I still belong here? Is this a place, a company where I still need… where I’ll still find engagement? Where I still want to work?

Is there something bigger out there for me?

And, “If opportunities are there for me, how am I going to go about doing that?How am I going to meet the right people? Get in front of the right people? And ask those questions? So that I can empower myself for my career trajectory.”

“It’s either still here at this company, or it’s somewhere else… Help me, help me figure that out.”

And, that’s what I’ve been spending most of 2020, all of 2020, really doing. So, we’re in 2021 now. Okay, so you help me find clarity.

“How am I going to make this plan actionable?”

“So now we’re working on, how do we take it forward?”

“How do I show up in a new world?”

Andrew Hryniewicz

Okay. Actually, it sounds like you’ve answered question number two, which is what’s the biggest challenge that they face?

Which it sounds exactly like, how do we make our way in this new environment? And who am I now? And who do I want to be?

Christina Holloway

Yeah…

“Who am I now?”

“Who am I in this new world?”

And, “How do I want to show up?”

And, “What does that mean?”

So when we look back at what it means for your personal brand, it’s easy for us to look back and say… “Well, maybe the past 10 years, I was just showing up, I was getting paid”.

“I was working with good people; I would go… commute to work every day…”

It all was on autopilot. And I was doing fine. You know, I could pay my bills, I could take vacations.

What a basic way, for me to explain how life used to be in 2019. And how it all got torn apart in 2020.

And then, in terms of brand, I needed to go back and ask myself, “Who do I want to be, when I show up now?”

Maybe, that wasn’t the life that… because it was just easy for me. Maybe that, necessarily, isn’t where I want to be now.

So we’re asking those questions. If you’ve come to this new realization that life is a little bit different. Or you’ve decided, I’ve now decided I’m going in a new space…

Maybe I was promoted to a bigger job…

Maybe I was given a raise and asked, “You’re going to have these new responsibilities.”

Maybe I was transferred somewhere else…

These are all people I’ve actually worked with. And then, maybe I was asked, or I realized there were opportunities at another company.

And all of those questions are, “How do I show up so I can be successful right out of the gate?”

Andrew Hryniewicz

I think that ties in perfectly with question number three, which is what’s the one insight you would share with them? To help them right now and those sorts of situations?

Christina Holloway

So, when we develop that type of persona, we’re looking at “How am I really communicating?”

If I look at the basic fundamentals of what it means to coach somebody through a difficult situation, we’re going to look at the fundamental part which is:

“How am I communicating?”

“What kind of information is coming my way?”

“How am I processing that information without it being overwhelming?”

And then, “how am I responding in a way that doesn’t set me off and accidentally trigger me to say something I’m not supposed to say, or that I shouldn’t have said?” Right?

So, we want to act from a space of being intentional, and not from a space of being reactive.

So, communication is the underlying theme…

“How am I communicating powerfully? How am I communicating so that my voice is being heard?”

“How am I understanding that the way I put myself out there and the things I say, I’m reflective of?”

I’ve had somebody say, “Every time I say something, somebody misinterprets me” or “Why do they assume that I’m this kind of person? When I’m really not… I don’t understand where it’s coming from?”

That’s what we’re trying to correct. That’s what we’re trying to fix.

If there’s a disconnect, we have to build that bridge.

And we have to help these other people understand who you really are. And what you’re doing to show up.

And, if you’re not creating enough boundaries… if you’re not speaking up for yourself… if you’re not correcting people when they make the wrong assumption…

So, it’s all part of you figuring out what your brand is, and how you’re showing up, with a little bit more ease, naturalness and confidence.

Andrew Hryniewicz

Okay, great. Sounds like some very important stuff.

So question four is: What concept, book, program, talk or experience has been the most impactful for your own development?

Christina Holloway

I’m actually going to say, I’ve referred back to the book “Influence: Science and Practice” by Robert Cialdini and the book “Nudge: Improving Decisions about Health, Wealth, and Happiness” by Cass Sunstein and Richard Thaler.

So, these two books are directly related to influence and persuasion. I did speak about that recently at another presentation I did.

So, in this example, a lot of this is asking yourself, “How does the world see me? How are we navigating the world?”

“Do we just believe everything that we see in front of us?

Are we showing up in a way that helps people understand who we are?” And “How are we creating that level of influence, so that they come along with us on our journey?”

This isn’t about manipulating people, but it’s about helping them understand who I am, and where I want to go.

And then asking them… “Are you going to come along with me? This is where I’m going. Are you coming along?”

And, this has a lot to do with being a manager, working on teams. Or even running your business and having either clients or people who work for you.

Saying, “You know, I don’t know if we’re on track here?”

So a lot of this is about… how am I communicating with more clarity… and how I’m making sure that people understand my point of view…

And then using these types of simple techniques to just make sure they can come along with me and understand.

It’s a lot about working with personality types and getting into the head of a person who needs to be convinced, or who needs to understand.

And making sure I’m communicating in terms of each person, that’s a recipient of how am I communicating so they can receive what I have to say.

Those books are quite profound. I refer to them a lot. And, they form a foundation of a lot of what it means for human condition, decision making, and understanding of our habits.

Andrew Hryniewicz

That reminds me of, I think it was, the book was “Leadership Jazz”. It was by the ex CEO of Herman Miller; I think it was Steve DuPree or Max DuPree maybe.

And he said that, “The leader’s job is to set the vision, and say thank you”.

Christina Holloway

Exactly.

Andrew Hryniewicz

So, that seems very similar to that…

Okay, so question number five, what’s a free resource you’d like to share with the audience, that can help them out?

Christina Holloway

So today, I will be sharing my ebook, which is related to this framework. And this is about developing a powerful personal brand.

And it’s about just showing up, taking it from average to excellence.

And so we talk about in this framework: what does it mean to build authority? When I ask myself: What do I know most? What do I know best?

Starting to identify with how I want to define who I am?

“Am I greatest at accounting? Am I a great engineer? Am I great at project management? Problem solving?”

I start to figure out what the definition of myself is, as I show up to work.

And the second part is, how am I building respect?

Which is how am I showing up at this job or this company? And allowing people to understand. The better I communicate, the more I define my brand and who I am. What will I tolerate.

“Do I appreciate high standards? Do I appreciate transparency? Do I speak with conviction and with respect to other people?”

I’m putting that out there and I’m asking others for that as well. So I’m building this level of respect that people can work with me.

And then the last part is, how am I building trust?

So, it isn’t just that I’m asking for respect, or I’m giving respect and finding this mutually respectful professional relationship.

But also, “How am I building trust? How do I show them that there’s credibility? How am I creating this level of… I believe you, therefore, I’m coming along with you.”

This is all about…

Building a personal brand is all about communicating effectively. But also building powerful, personal or professional relationships that are going to help you go to the next level.

We don’t do it alone. You and I both know: we don’t do this alone.

So, how are we creating powerful relationships that help us go? And keep going?

And then what we learn is:

“I can keep going, but… I have impact. I impact those people around me. I impact the people above me. I impact clients. I have impact.”

I’m doing it in a way that I’ve defined: this is the kind of person I am. I can step with confidence forward, knowing I’ve defined this is who I am, this is what I will and will not tolerate…

So that’s my downloadable.

I hope people enjoy it.

Andrew Hryniewicz

Okay, so that will be at christinahollaway.com/profitable-brand-ebook/.

Okay, Christina, the last question. What should I have asked you that I didn’t?

Christina Holloway

Oh, gosh, let me think…

I’m trying to think of something clever. And I’m coming up blank.

So, alright…

I’ve done the work. I’m figuring out my communication. I’m figuring out my boundaries. And figuring out how to create trust with other people.

Now I have all these foundational elements, “Where am I going to go next?”

Then figure out, how am I going to show up?

And then figure out, how am I carrying myself forward?

Those powerful conversations are with those people who are decision makers. Those ones, “the big client that I always dreamed of getting?”

“How am I getting in front of that person?”

And, when I do have that opportunity, how am I going to make an impression, without, you know, coming across… with the wrong impression, right?

Or, if I’m talking to decision makers who are responsible for my promotion, or for the job I’m supposed to have…

“Who are my stakeholders? Who are the people who are going to advocate for me, so that I can get promoted?”

The first step is, which was what we’re talking about today, “How do I realign who I am? How do I redefine who I am as I show up in this new world?”

And then, step two is “How do I take action?”

In coaching, small change makes big impact. It’s known, that this is what coaching does…

We make small changes every day. If you run into problems with somebody… you just want to go every day… go in there with just a small change in attitude, ask a different question.

Do something different than you did the day before. And then, observe what happened? How did the dynamics shift? How did it ripple across other relationships?

And then ask yourself, “What can I do tomorrow?”

Set small goals for yourself, and then keep moving forward, keep taking steps…

The difference between someone who’s successful and someone who isn’t is that the successful person kept trying.

And that’s what matters.

Andrew Hryniewicz

I think it’s the famous Winston Churchill.

Christina Holloway

Right? I paraphrase.

Andrew Hryniewicz

You go from disaster to disaster without a loss of enthusiasm.

Christina Holloway

Yes. That’s perfect.

Andrew Hryniewicz

You know what? You know, he was an amazing example of that.

Christina Holloway

Yeah.

Andrew Hryniewicz

Well that’s perfect. Christina, thank you so much for your time today.

Christina Holloway

Thank you for the invitation. I appreciate it. It was a pleasure talking to you.

I’m very happy to contribute and I’m really excited to hear when the podcast comes up.

Narrator

Thanks for listening to the destiny awakening interviews. If you have a friend who would benefit, please share, and subscribe to the show on iTunes and leave a review. We really appreciate it. And remember, always use your power for good

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Andrew Wayfinder Hryniewicz

Philosopher. Shaman. Architect. Therapist. I love time spent with friends and family, creating beauty and magic, and this amazing planet we all share.