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Jennifer Einolf With Bold Whisper LLC

June 2, 2025 by Jacob Lapera

High Velocity Radio
High Velocity Radio
Jennifer Einolf With Bold Whisper LLC
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Jennifer Einolf is a leadership coach, speaker, and founder of Bold Whisper LLC, where she partners with visionary leaders to translate complexity into clarity and channel creativity into powerful, aligned action.

Drawing on her background in design and her unwavering belief in human potential, she leads Ditch the Doom—a revolution that rejects the paralyzing narratives of fear and scarcity in favor of courage, collaboration, and creative leadership.

Her work challenges the norms of marketing by rooting visibility in trust and positions coaching as a strategic, truth-centered engagement that catalyzes bold outcomes.

Connect with Jennifer on LinkedIn and Facebook.

What You’ll Learn In This Episode

  • Visionary leadership and everyone is creative–cultivating creativity for leaders and teams
  • Ditch the Doom–the revolution she’s starting to move is from the Doom song to singing hope with courage, collaboration, and creativity
  • Pain points and coaches–building trust and still being able to market to pain points

Transcript-iconThis transcript is machine transcribed by Sonix.

 

TRANSCRIPT

Intro: Broadcasting live from the Business RadioX studios in Atlanta, Georgia. It’s time for High Velocity Radio.

Lee Kantor: Lee Kantor here. Another episode of High Velocity Radio, and this is going to be a good one. Today on the show we have Jennifer Einolf. She is the clarity coach and founder and CEO of Bold Whisper. Welcome.

Jennifer Einolf: Thank you. So glad you invited me for this conversation.

Lee Kantor: Well, I’m excited to learn what you’re up to. Tell us a little bit about Bold Whisper. How you serving folks?

Jennifer Einolf: Certainly. So I work with creative leaders, the kinds that think of 4 to 5 new worlds before breakfast, and then bring that to their team and create a lot of chaos. So I work with leaders who need to design the clarity necessary to be able to explain what it is they see, and then uplevel their communications so that they can communicate that to the people, the key stakeholders that are going to make it happen and support it, and to harvest all of that creativity in themselves and their teams. I also work with teams doing retreats because I believe everybody is creative, and sometimes we label some people as creative, but everybody is. You wouldn’t still be here if you weren’t creative. You’ve solved a problem at some point. And so it’s really critical for organizations, for leaders and teams, to understand their own brand of creativity so that they can nourish it and they can harvest it.

Lee Kantor: So what’s it like working with leaders who are kind of in the classic, like you described, the the creative that the visionary who’s coming up with idea after idea and then, you know, excitedly shares that with the team and then kind of intellectually moves on to their next great idea that they’re having at lunch. And then while the rest of the team is just like, are we not doing what we did yesterday? Like, is this the new most important thing? Like, how do they actually create systems to move from idea to execution?

Jennifer Einolf: Yeah, absolutely. One of the big misunderstandings that you just outlined so beautifully is the difference between something that occurs to you and something you want them to do. And so working to leave plenty of space for all of that messy ideation and creativity and starting to build, build an awareness and a skill set around determining which ones they need to pay attention to. And when I’ve worked with leaders who mention things off the cuff and everyone thought they meant by next Tuesday and they meant, oh, in the next 30 years, this is probably what’s going to happen. And their brains require that they need to play. They need to poke at it and say, well, what if we do this? And what if we do that? They also need if they want to have the most important things actually happen, differentiate between that bucket of interesting things and the pointed things they want to get done. So that’s why communication is a big part of what I do with my clients. It’s not just communication skills. How do you stand up and speak in front of people? A lot of them are very accomplished at that. It’s the communication skills of how do you design your clarity sufficiently, and then how do you bring that to people? A lot of leaders feel like if I said it once, then they should know.

Jennifer Einolf: But the very dynamic that you just outlined is the reason that most people aren’t sure. Is this the one? Is this the one? And so there’s a negotiation in it. There’s a if you need a certain way of processing, how do you get the space for that processing and create enough social contract with your direct reports, with your colleagues, even with your bosses to say, okay, this is one of those situations where I’m doing this and in a minute I’ll tell you what the outcome is. So there’s a lot of reframing that can go on that doesn’t eliminate all of that beautiful mess. And I think a lot of creative leaders, a lot of creative people in general, are very afraid that someone’s going to cut them off. They’re going to shut it down and say, no, you have to be like everyone else. We really don’t want them to be like everyone else. We need those beautiful brains, but they need to find that touch point where they can communicate effectively with everyone else. And so how do you, like I said, how do you create enough space for all that beautiful mess and signal? When the mess is over, you’ve put the toys away and now it’s time to actually do this. One version of it.

Lee Kantor: Now does.

Jennifer Einolf: It.

Lee Kantor: Does it require somebody on the team to be kind of the translator or the intermediary that the the creative can, you know, kind of vent and process and, and bounce ideas off of and that person then kind of hones in on the priorities it can.

Jennifer Einolf: And a lot of times that happens organically anyway, you know, you gravitate towards the person that understands you, especially one that’s had success in explaining you to other people. Um, it’s what a coach is for. It’s it’s what I do too. Um, and by working with a coach, you can start to understand how to develop those relationships with different members of your teams, because there may be different people for different messes, there may be different people for different forms of creative iteration and design cycle thinking that have different strengths, and identifying who those people are. Yeah, that’s really critically important.

Lee Kantor: So does it ever occur where you have a visionary who has ideas and maybe started as a solopreneur themselves? So they were kind of executing the stuff. Then they grew a little bit, and then they get to the point where they’re now like a frustrated visionary, where no one really understands and no one’s, you know, getting their their ideas out the door in a, you know, monetized manner.

Jennifer Einolf: Yeah. I was very tempted to respond in a sarcastic manner, but I wasn’t sure it would read properly. Of course. Absolutely. There is a growth pattern in all leaders and the the founder to leader that well, the crazy idea guy founder leader. Pipeline is a is a very common story where you did these amazing things and you attracted these amazing people to you and you said things no one else was saying, and you created all this energy, and then you went and you took that, and you venture pitched it and everybody was excited. And then you go into the office one day and you realize, wait a minute, now I have to execute on this. I have to herd these cats that I have attracted to me. I have to I have to be able to make good on this. And that is a crisis point for a lot of leaders. It’s an absolute crisis point. It’s also the place of amazing opportunity for both growth and development of them as leaders, but also for what their organizations can do when that traction starts to happen. So yeah, absolutely. It also happens in in the corporate world where they hire in the, the the bright new guy, the bright new woman who’s going to change everything. And then the organization itself Self begins to resist that person. Yeah, but we’ve never done it that way. And even if they don’t say it out loud, you can kind of hear it. And so those transition moments where what got you there isn’t going to get you there. Those are absolutely the moments where having a coach, having someone who is very much invested in what happens to you without being invested in the situation can really help you see, what am I not seeing? What’s missing here? What’s the potential? Because in those moments of crisis, you have a choice to either shut down or go fish for where the opportunity is. And I’d much rather that they fish for where the opportunity is now.

Lee Kantor: Um, is most of your work with, uh, kind of smaller, more nimble firms, or do you work also with kind of larger enterprise where, like you mentioned, they hire, you know, somebody into a more bureaucratic environment and they say this person’s here to disrupt the status quo, and then everybody realizes that they’re part of the status quo and they don’t want to be disruptive.

Jennifer Einolf: Wait a minute. I didn’t mean for them to disrupt me.

Lee Kantor: I didn’t want any of that on me. That was for the other people.

Jennifer Einolf: Well, that’s it. Go fix. Go fix them. Um, the mandate to go fix them. I work in a variety of settings. A lot of times it’s, uh, someone will meet me or hear from me and realize that this is the time. And that time happens in a lot of contexts. So I work in a lot of contexts. I’ve worked in corporate, I’ve worked in, I’ve worked I’ve done a lot of work with the federal government over the last few years, and you can imagine that that’s that’s a transition for me right now. Um, and also small firms. Uh, firms that are about to venture pitch firms that are, uh, post funded. And so it’s really more about those moments of leadership transition of, okay, how do I continue to harvest this incredible creativity that I’m bringing to the plate because something is resisting, whether it’s the situation has changed or the people who hired me don’t know whether they want me to do this thing, or just that deer in the headlights look of your team. You know, everybody knows that it’s really lonely at the top. But what people don’t realize is it can be very lonely out in front where you think you’re charging forward and everybody is with you, and you turn around and there’s nobody there. And that happens in all kinds of contexts. So I work in those moments, and as I said earlier, I also work with teams. So doing, um, retreats or team trainings or team coaching to really get at. He’s not the only creative person. She’s not the only one here with spark. Let’s see what your spark is, because you’re going to need to be creative in delivering this thing. And I love when I get to do, you know, get to play the dynamic in that direction where we get to bring people closer to that center point where the ignition actually happens. So, yeah, an answer to your question. I work in a variety of contexts. It happens everywhere.

Lee Kantor: But it sounds like one of the kind of linchpin, uh, People involved in working with you. There has to be somebody that’s a creative visionary, either for themselves, they need help, or they see the value of bringing that type of skill to their team.

Jennifer Einolf: Yeah, it’s usually the visionary themselves. Sometimes I’m brought in to work with a visionary, but I find that that often doesn’t work because the person who’s bringing me in often feels like they need to fix the visionary instead of enable the vision or enhance the visionary. I have been able to do that successfully a few times, but often it’s it’s partnering, partnering with that leader that I just really believe that the quality of our leadership right now is what determines what happens for us as a species on this planet. And partnering with the people who are hearing things and seeing things, the rest of us aren’t to make sure that those things happen, because that’s how we go forward. That’s absolute jet fuel for me. So it tends to be me forming, forming partnership with the leader. And then if I’m working with their team, it’s in service of getting everybody forward.

Lee Kantor: So what’s the what’s a symptom that that leader may or may not have the self-awareness to know that they have a problem. But there’s if certain things are happening, it probably warrants at least a rethinking. Is there some things that happen in their organization or in their kind of emotional state that is signaling, hey, maybe you need a coach to help you get through something.

Jennifer Einolf: I love.

Jennifer Einolf: That question. So how do you know if we’re talking about you? That’s such a good question. That’s a really good question. So some of the things that happen are the leader starts to get really frustrated because they keep being brought, things that they didn’t know they asked for. And they see their team getting frustrated because the team has worked on this thing. You know, that’s that’s the most obvious version. And then you don’t know. You said this last Tuesday and they’ve been working on it for a week or for a quarter or whatever. A real disconnect between it’s those points of resistance when when you when you have a vision of what you want to see happen, how smoothly is that happening? You know, you’ve got good people. You trust your people, you’re amazed by your people, and yet somehow you’re getting beat to market by other companies with similar products that you didn’t know anybody else had even thought of. You’re just feeling that resistance. And like I said, that deer in the headlights look. Or it can be employee retention issues where people are wandering off because they’re frustrated, looking for signs of that frustration. In a high functioning team, that frustration is not happening. And so, yeah, one of the one of the first awareness points are I had a I had a coach, I had a coach for me at one point who asked me to carry a paperclip around in my pocket, in my pocket, in my wallet. And it was to remind me that a paperclip is sometimes simply for putting two pieces of paper together, because I’m the kind of person that looks at a paperclip and thinks of all the hundreds of things you could do with a paperclip. Sometimes if you if you enjoy that, that’s the light of your skill. The shadow is is that disrupting other people? Is that disrupting your ability to ever get traction on the things that you really want to move forward? Do you need to carry a paper clip just to be reminded that sometimes simple things aren’t the enemy? They’re the answer.

Lee Kantor: Now, when you’re working with somebody, what are those early conversations look like? Uh, you know, how do you kind of assess where they’re at and the outcome they desire?

Jennifer Einolf: Oh, absolutely. So I’m trained in ontological coaching, and ontological coaching is based on the idea that we take actions, we get outcomes, we don’t like those outcomes. So we go and take a totally different action and we get the same outcome. So it must be this must live somewhere else. So it’s about building our awareness of who we are and how we see the world that starts to create opportunities for us to open up new possibilities. So working with my clients includes a variety of ways of getting at that. So we use words. We use words beautifully. We can use words. We can also use physical awareness. How does that feel in your body? I know that sounds really woo woo, but this idea that you are living in this body and it may have some things to tell you and emotion. We in our culture, we’re not very good with emotion. And so what are your emotions telling you? What? I was really surprised that I felt sad or I really surprised that I felt angry. Okay, what might that have been telling you about your response to what was happening? So we go back to really fundamental ways of knowing who you are. Um, I use some really fun modalities. I’m trained in Lego serious Play. Sometimes when you’re stuck, you can export what you’re thinking into a physical object, and in exploring that object and making meaning out of what you just built, you can unlock things.

Jennifer Einolf: So much of coaching is about unlocking. And then when you’ve decided that you’ve seen something new, something you haven’t seen before, what are you going to do with that? So co-creating an experiment with my client. Okay, wait a minute. I just realized that this thing is happening that I have been ignoring, or I really want to do something with this. All right, what does that look like? Is it a new habit? Is it an experiment we’re going to run? What does that look like? And that’s why coaching unfolds over time, for the most part, because you need that time to have the aha moment with the coach and then go do something with it in between. And that’s where the real transformation starts to happen. And when it comes to leadership skills, there is a real need for awareness. And I think a lot of us are afraid if we go too much into what we think or what. How is that helping me communicate with other people? But it’s the it’s the things we’re not seeing. It’s, you know, the fish is the last one to understand that they’re swimming in water. It’s the things that we’re not seeing that blind us. It’s not that we’re blind.

Jennifer Einolf: And so working with a coach to really build awareness, to figure out where you even want to work on things. And then there’s the skill set. There’s working on communication skills. There’s you know, sometimes we do we do role play. There’s a difficult conversation coming up. Let’s talk about how you’re going to approach that. Or there’s a really critical thing you want people to understand. Let’s let’s really play with that and think of all the ways that this could this could be delivered and what the what the outcome is that you’re, that you’re shooting for. So it’s a, it’s an ongoing unfolding of, of possibility of potential with a lot of real world practice in between sessions, which gives you a real edge on people who are not learning, not growing, and not trying to figure out what they need to do. So basically that’s yeah, that’s how that’s how I work. We go in, we rearrange your brain. I, I have an interior design background. I used to be a commercial interior designer. So I always laugh and say I used to do external interior design, moving furniture around. Now I do internal interior design, moving your internal furniture around. But you never know. Are you tripping over the same chair in your head over and over again? Let’s let’s move the chair now.

Lee Kantor: Is there an exercise you can share with our listeners that maybe would kind of at least spark a glimmer of light in what they’re doing now that might uncover something that they need help with. Do you have kind of a basic homework or an assignment you give people or something? They can just try right now?

Jennifer Einolf: Yeah. Basic homework. You know, if you’re trying to build awareness and, you know, we all have people have meditation practices or they are resisting meditation practices, which is a whole other thing. Um, but awareness really comes from having a moment to notice what’s happening. And so one of the things I like to do that, uh, with my clients is set some random alarms. We’re all carrying alarm clocks around in our pockets now, so set some random alarms and on the alarm rate. What’s happening right now? It can be that simple. How do you break into the flow of what you’re doing anyway? To create a moment of awareness? And you may catch yourself, oh, I thought I was doing this, but I feel really angry or I, I am doing something that I would rather do because I’m putting off doing the thing I should do. I don’t know, I don’t know what it is. But if having having passed you ask present you an intrusive question can start to build that awareness. How else are you going to break into the flow of what you’re doing? So set 4 or 5 alarms for tomorrow. Set them at random times, and when they get when they go off, ask yourself, wait, what’s happening right now? It’s worth a shot.

Lee Kantor: Yeah. And you’ll find out if you’re doing the things that you want to be doing to lead that ideal life that you think you want to lead, so.

Jennifer Einolf: Your life to build.

Jennifer Einolf: Are you building relationships or tearing them down in that moment?

Jennifer Einolf: Right.

Jennifer Einolf: Are you, um, are you moving forward or are you spinning wheels? How are you feeling about it? I’m doing it, but I’m really upset about it. Well, what could you do to be a little less angry about what you’re doing? Whatever emotions come to tell you what you’re up to, you don’t have to stick with them. You can say, well, I think I would rather do this from a place of and maybe there’s a shift of mood you could make, which might make things easier. So yeah, just just doing that basic awareness can be a really good start. And what’s happening because I’m doing this might be that’s your extra credit question. So what am I doing right now. And then what’s happening. Because I’m doing this. Well I’m really angry because I got cut off in traffic this morning and I’m talking to my colleague. Oh, and I’m still angry. And and they have this frown on their face. So in the flow of it, I don’t know if it’s worth the experiment to check in on ourselves occasionally, you know. A big part of building creativity or nurturing creativity, um, is breaking through habits. Our brains do a lot of things to save energy because our brains are energy hogs. They they use a tremendous amount of energy, which is good.

Jennifer Einolf: That’s why we’re so successful. And if we never ask our brains to do something outside of those habits, then we don’t know what else is possible. So something as simple as writing with your other hand, or taking a different route to get to where you’re going, even if you’re walking from one office to the other or driving to the supermarket, taking a different path, you know that road that you’ve passed a hundred times and you don’t know where it goes. Take that road every once in a while in in asking your brain to do something new, you are growing your capacity for creativity and creative people still need to nurture their creativity. That’s why famous artists, famous writers get writer’s block because they haven’t nurtured it. They’ve just continued to utilize it until they’ve depleted it. And so having a habit, like having a trying a little experiment, like, what am I up to right now, can give you some insight into that too. I need a creative break. I need to take a breath. I need to take a drink of water. But maybe I need to just soak in this beautiful view outside the window. Or maybe I need to o engage my creativity here. You never know what your brain’s going to answer when you ask that question.

Lee Kantor: Now, is there a story you can share that maybe from one of your clients? Don’t name the name of the client, but maybe share the challenge they came to you with and how you were able to help them get to a new level?

Jennifer Einolf: Yeah, that’s always a difficult question because trust is the most important thing with my clients. And so how do I tell these stories without ever running the risk of having someone know, um, that that’s who I was talking about. But I worked with leaders. This has happened several times, so maybe they won’t hear themselves in the story. I’ve worked with leaders where the container that they’re in, the room that they’re walking into is impacting how they’re communicating. So for instance, um, a, a large space where you are an afterthought way down below the slides and you’re, you’re needing to command that room. Sometimes it’s as simple as booking a different room. So don’t have 50 people in a room that seats 300, have 50 people in a room that’s almost standing room only. And make sure you’re positioned up and up and in front. So some of the some of the things that some of the solutions that pop into people’s heads come when we shift, what question we’re asking and we shift shifting the question from, why am I uncomfortable doing this? To what am I trying to accomplish here? And what might help that happen. What might what might facilitate that. So yeah, that’s a that’s a pretty decent example because that has happened on numerous occasions where the answer was hiding in plain sight, and it was a matter of asking a different question.

Lee Kantor: So if somebody wants to learn more, have a more substantive conversation with you or somebody on the team, uh, what is the website? What’s the best way to connect?

Jennifer Einolf: Absolutely. Bold whisper comm. And if you go to the About About Me page, there’s a place there to connect with me, and I, I love conversation, I would love to speak with you.

Lee Kantor: Well, Jennifer, thank you so much for sharing your story today. You’re doing such important work and we appreciate you.

Jennifer Einolf: Thank you so much. I really appreciate the chance to come in and speak with you.

Lee Kantor: All right. This is Lee Kantor. We’ll see you all next time on High Velocity Radio.

Tagged With: Bold Whisper LLC, Jennifer Einolf

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