Dashing Leadership Pre-call FAQ

Intro

If you're reading this, you're probably firefighting your way through several decisions while your team waits for answers. You know intellectually that you need to delegate more and think strategically, but something keeps pulling you back into the weeds. Usually it's anxiety about dropping balls, fear of losing control, or just not trusting that others will handle things the way you would.

This document will help you understand whether coaching, specifically my approach to coaching, can help you shift into a different way of leading.

If you have any questions, feel free to email me at brian@dashingleadership.com or text me at 201-658-9525.

Why hire a coach in the first place?

You probably already know what good leadership looks like. You've read the books, listened to the podcasts, maybe even hired that VP who was supposed to "bring the process." You understand you should delegate more, give clearer feedback, make decisions faster, think more strategically.

So why aren't you doing it consistently?

Usually it's because something emotional is getting in the way. Anxiety about letting go of control. Fear of conflict when giving hard feedback. Perfectionism that makes you redo your team's work. Or maybe it's the voice in your head saying "if I don't do this myself, it won't get done right."

The problem isn’t knowing what to do. It’s the emotional patterns that hold you back. My job is to help you deeply understand those patterns so that you can make different choices. This may even sometimes feel like therapy, though it’s not quite that. The point is we're always connecting it back to your leadership and the results you want to create.

The same applies if you're working through challenges with your cofounder. You probably both intellectually understand what needs to happen: better communication, clearer decision rights, more aligned vision. But something keeps you stuck in the same patterns. We go deep on what's really happening emotionally between you, then translate that understanding into action on the actual relationship and company challenges in front of you.

How I Work

I work at the intersection of practical leadership and deeper emotional work. Sometimes I'll ask questions that help you discover your own answers. Sometimes I'll share direct perspective from my experience as a founder. Sometimes we'll explore a fear or pattern that feels therapeutic in nature.

What I'm not doing is making you choose between "tactical leadership advice" and "emotional processing." The best leadership development requires both.

What this looks like in practice:

  • You bring a challenge (difficult conversation, strategic decision, team conflict)

  • We investigate what's making it hard, sometimes that means surface-level tactics, sometimes it means going deep on your emotional patterns

  • We figure out what to do about it (new approach, different perspective, concrete practice)

  • You go try it, report back on what happened, and we adjust

I'm influenced by frameworks from Art of Accomplishment, Conscious Leadership Group, Internal Family Systems, and Coherence Therapy. These are all approaches that take emotional and psychological work seriously. I also bring my experience as a founder and operator.  I use whatever is most useful for unlocking the change you're trying to create.

An Example

Let's say you hired a VP of Engineering six months ago and you're still making all the technical decisions. You tell yourself it's because they're ramping up, or because you need to maintain quality, or because "it's faster if I just do it."

As your coach, I might help you see that you can't effectively delegate without the capacity to tolerate the anxiety of not knowing exactly how things will turn out. We'd explore what makes letting go feel dangerous. You might discover a belief that your value comes from being the technical expert, or a fear that if you're not essential, you're replaceable.

Once we see the pattern clearly, we work on what to actually do. Maybe that means practicing staying present with discomfort when your VP makes a decision you wouldn't have made. Maybe it's redefining what "maintaining standards" actually means. The depth work creates space for you to actually start delegating instead of just knowing you should.

What kind of founder gets the most from my coaching?

Stage: You're typically post-seed, scaling toward or through Series A/B. Your company is growing faster than your leadership capacity and you feel it. The problems you could solve by working harder or being smarter aren't working anymore.

You're stuck in patterns you know aren't serving you:

  • Jumping into execution mode instead of empowering your team to own outcomes

  • Avoiding difficult conversations until they become crises

  • Making decisions reactively instead of stepping back to think strategically

  • Feeling constant anxiety about outcomes you can't directly control

  • Struggling to trust your team to handle things without your involvement

  • Micromanaging because letting go feels terrifying, even though you know it's unsustainable

If you're working with a cofounder, you might also notice:

  • Communication gaps that turn small disagreements into big blowups

  • Resentment building because responsibilities feel unclear or unfair

  • Avoiding hard conversations about equity, decision rights, or performance

  • Falling into the same argument patterns despite "resolving" things multiple times

  • One of you feeling like you're doing all the heavy lifting while the other doesn't see it

Your mindset: You're willing to look at your own emotional patterns, not just learn new frameworks. You understand that sustainable change requires understanding why you do what you do, not just what to do differently. You're curious about yourself, even when what you discover is uncomfortable.

You want to grow, not just solve problems. You recognize that the challenges in front of you require you to become a different kind of leader than you've been. That's uncomfortable work, but you're willing to do it.

What happens in the sessions?

At the start of the session, I'll ask you to reflect on what progress you've made since our last meeting. This is an opportunity to crystallize any learnings you've had, celebrate wins, as well as identify where to continue your focus. Usually this part will take 5-10 minutes. From there, I'll invite you to bring forth a challenge or goal you want to work on, which is what will take up most of our time. As we explore and develop clarity on the nature of your situation, a few different variables might emerge: decisions to be made, conversations to be had, and how you play into everything. It's the latter where it's often helpful to dive into the stories and mindsets you're bringing to your leadership. Eventually we'll arrive at some shift you can make to move the challenge forward. That's where we co-create practices and next steps, not just to move you closer to your goals, but to also advance your own development.

What do sessions actually look like?

Here are real scenarios we might work on together (details changed to protect confidentiality):

Individual Founder Coaching:

  • You need to have a hard conversation with a VP about performance, but you keep putting it off. We explore what you're afraid will happen; not just surface level ("it'll be awkward") but what it means about you if you have to have this conversation. Then we prepare you to actually do it, including roleplay if that's useful.

  • You intellectually want to delegate the product roadmap to your Head of Product, but you find yourself jumping into every decision. We investigate what makes letting go feel dangerous. Often there's anxiety about losing control, fear that things won't meet your standards, or even identity wrapped up in being "the product person." Once we understand that, we create a concrete plan for how you'll actually start delegating.

  • You're making a major strategic decision (pivot, fundraising strategy, key hire) and notice anxiety clouding your judgment. We create space to separate the anxiety from the actual decision factors. Sometimes that means just naming it and moving forward. Sometimes it means exploring where the anxiety comes from. Either way, the goal is a clear decision you feel good about.

  • You snapped at your team during a stressful week and now feel terrible about it. We look at what triggered it - what were you protecting or avoiding in that moment? - then figure out what you're going to do about it. Usually an apology to your team and a new practice for catching yourself earlier.

Cofounder Coaching:

  • You and your cofounder keep having the same argument about who makes final decisions on product vs. business. We help you both see what's underneath the argument; often one person's need for control, the other's fear of being sidelined, accumulated resentment neither of you has named. Then we translate that understanding into clear agreements and decision rights that actually work.

  • One cofounder feels like they're doing all the "real work" while the other feels unappreciated. We go deep on what's creating these perceptions and help you both understand each other's experience. But we don't stop there, we help you create new structures and communication patterns that address the actual problem.

  • You're avoiding a conversation about equity, role changes, or one cofounder potentially stepping back. We create a container where you can have that conversation with honesty and care. I'll help you both name what's hard about it, then support you through actually making a decision.

When we're not a fit

I'm very good at helping founders understand their emotional patterns and build new capacity. I'm not the right coach if you:

  • Need only tactical/operational advice. I can share perspective from my founder experience, but if you mainly want someone to tell you how to build your sales process or structure your team, you want a different kind of advisor.

  • Aren't ready to look at your own patterns. If you believe your challenges are purely external (bad co-founder, difficult market, incompetent team) and aren't curious about your own role in creating current results, this won't work.

  • Want quick fixes. The work of building new emotional capacity takes time. If you're looking for a framework you can implement this week to solve everything, you'll be disappointed.

Logistics

Format: We meet every 2 weeks or every week for an hour over video, depending on your needs. Engagements are open-ended with no minimum commitment. Some clients stay 6 months, others over 2 years.

Between sessions: Email (48-hour response), text for urgent matters (same day), and ad-hoc calls when you need them. I'll often send Loom videos for questions that deserve nuance.

Investment: The monthly retainer is $2,000 for biweekly sessions or $4,000 for weekly. This covers our sessions plus ad-hoc support between them. I occasionally make exceptions for earlier-stage founders.

Cancellations: Life happens. If you need to cancel, we'll reschedule if possible; if not, the retainer stays the same. If you need extra support before a big meeting, we can do that too. For prolonged breaks like vacations, billing is prorated.

How do I know if you're the right coach for me?

Great question! Only you can know for sure, but here are a couple of tips. First of all, talk to a few coaches - 3 is usually fine - to get a sense for personality, background, and coaching philosophy. This makes sure you get enough information to make a solid decision. Secondly, get clear on what you want: is it skill training? Then I'm probably not the best person for you! Is it cultivating yourself as a leader? Then we're much more likely a fit. Finally and probably most importantly, pay attention to how you feel energetically when we have our initial conversation. If you appreciate and want more of that energy, then that's a strong indicator we're a good fit!