Dashing Leadership Pre-call FAQ
Intro
If you're reading this, then you're likely considering the possibility of hiring me as your coach. This document is meant to help you understand what it's like to work with me, answer some common questions, and help you make an informed decision!
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?
Wise leaders recognize that they are the limiting factor to their company's success. Addressing those limitations requires a difficult - sometimes painful - process of gaining new skills and rewriting parts of their internal operating system. It's the type of growth that most people avoid. Instead, they usually double down on their existing operating system, which might get them by for a while. If they’re lucky.
But if you’d prefer not to rely on luck, then you’re left with no choice but to grow yourself. That’s messy work! It involves getting familiar with your fears. You have to be willing to try things you’ll probably suck at at first. But the process is worth it in the end. And a coach can help you massively accelerate that process.
An Example
Let's say you're trying to give feedback to somebody and you find that whenever they react defensively, you shut off the conversation. You conclude this person can't receive feedback gracefully and there is no reason to continue. Based on this information, I might assert that you can’t effectively share feedback without the capacity to be with somebody else's discomfort. As your coach, I would invite you to explore that compulsion to shut down. We might find a host of stories you have about the situation. You might discover a belief that says feedback should be delivered with no room for disagreement. You might even see a particular part of your identity you desperately want to hold on to but is keeping you blocked. As we take a look, we work to find new perspectives and practices that ultimately help you create the outcomes you want rather than leave you subject to those default reactions we found.
Why do I coach?
Having spent a decade in startups as a founder, investor, and product leader, I came to recognize a simple truth: most of us approach leadership unconsciously. Our default patterns run us and while that can work for a while, sooner or later things will start to break down. Then we flail, we double down on our existing approach, or we start to blame the outside world for our troubles. This response usually doesn’t create the results we desire, but I’ve seen it happen countless times both in myself and in others.
I coach because I believe the world needs more out of our leaders. And that can only happen when we do the work to get honest with who we are and who we need to become to meet the challenges in front of us. Coaching is how I support that work.
What’s your style of coaching?
You may have the impression that a coach does nothing but ask you questions, forcing you to come up with the answers all on your own. This is what I call an inquiry-driven approach. On the other hand, some coaches are much more directive and are not afraid to give advice, best practices, and tools. I’m somewhere in the middle, with a lean toward the inquiry side of things. Philosophically I believe that the best leaders emerge from a place of curiosity about themselves and the world. Their curiosity is the source of their wisdom. So I will most times work to help you cultivate that. But if I detect I can offer something from my own past experience that would support you in your development journey, I’m not afraid to offer it. Don’t be afraid to ask what I think, as long as we’re clear that the responsibility for your growth is yours.
My coaching is influenced and informed by Art of Accomplishment, Conscious Leadership Group, Internal Family Systems, and Coherence Therapy, along with my many years as a founder and operator.
What does your typical engagement look like?
Before we start, I'll ask you to fill out a questionnaire designed to help you develop self-awareness around your strengths, weaknesses, aspirations, and growth areas. This is not only an opportunity to help you know yourself better, we'll also use your answers in our first session to define your goals and the roadmap to get there.
We will meet every 2 weeks or every week for an hour over video call, depending on your needs and budget.
Engagements are open-ended in nature and I don't require a minimum commitment. That said, I aim to work with clients with whom I believe there can be valued long-term relationship. Some clients have spent 6 months with me and others have been with me for over 2 years. Your mileage may vary!
How do I get the most out of the sessions?
I wrote a detailed post on this but here's the high level:
Prepare: Take time to reflect on where you are and identify a topic/challenge that is meaningful to you and your goals.
Mindset: Adopt the perspective that we’re here to help you grow, not focus on problems. Yes, we’ll tackle challenges together, but we’re here first to support your transformation. At any point you should be asking: how am I growing right now?
Present: Be fully present and engaged. Remove distractions and focus on the conversation. Taking notes is fine, unless it takes too much of your attention!
Practice: Commit to practicing new things based on the learnings that come out of the session.
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 co-create practices and next steps, not just to move you closer to your goals, but to also advance your own development.
What do most clients work with you on?
Here are the most common areas of development my clients come to me for:
Making hard decisions in ambiguous environments
Exchanging difficult feedback effectively
Becoming more resilient & managing stress
Finding purpose & meaning in their work
Learning how to coach and develop others
Building a culture of conscious growth
Resolving interpersonal challenges and improving communication
Who works best with you?
I find that the people who get the most out of working with me possess the following characteristics:
Curious & learning-oriented: I work well with people who desire to learn more about themselves personally and developmentally. They’re eager to grow by getting outside of their comfort zone.
High EQ: In my experience, clients who are not afraid of emotion, are tuned into their own, and can detect the feelings of others around them typically do well with me. Conversely, if you find you are fairly shut off from emotions or are not willing to open yourself to them, we might not be a fit.
Open to novel approaches: At times, I might suggest experimenting with practices like inner dialogue exploration or somatic awareness as ways to develop more insight. Working in these ways isn’t required but I find them to be very useful.
Eager to practice: The most effective clients turn insights into new actions and practices. So if you are committed to not just gaining more self-awareness but also doing something new with it, that’s a good sign!
Who is not a great fit for you?
If more than a couple of these describe you, I might not be the best coach for your needs:
You are looking for somebody to tell you exactly what to do as you build your company
You find yourself spending most of our time reporting on what’s going on rather than bringing specific challenges/goals to the table. That doesn’t mean you need to 100% always know what to explore together, but I recommend clients come with even a rough sketch.
You can name your stuck points intellectually but aren’t willing to explore where you’re tripping over emotionally. In my experience, durable change comes from engaging with and even welcoming the fears that lurk beneath the surface.
You are hoping for a quick fix. The reality is that long term transformation takes way longer than most people care to admit!
How do I interact with you between sessions?
Beyond our regularly scheduled meetings, I usually interact with clients in a few different ways.
Email: I try to reply to emails within 48 hours during the week
Text: For urgent matters, clients can text and I’ll usually get back to them within a few hours
Ad-hoc calls: If you need to get on the phone for anything at all, just ask and I will schedule time with you if I have availability. This applies for all clients, no matter our regular schedule.
Loom: Often clients will ask a question that deserves some nuance. In those cases, I’ll usually record a 5-10 minute video over Loom sharing my thoughts.
Resources: I have a large collection of books and articles that I like to share with clients, depending on their needs.
What’s the commitment?
I don’t require clients to make any long-term commitments for coaching. However, you do get out what you put in. Clients find the most success when they show up to meetings consistently and put in their best effort. So when you’re deciding on whether to work with me, ask yourself how committed you feel toward this process!
How do billing and fees work?
I do not charge by the session or the hour. The reason is because I find that approach puts unnecessary pressure and stress on all parties. Tracking time can distract from the work of development and creates a counterproductive context.
To me coaching is about long term partnership focused on your development. So I charge a monthly retainer that reflects the commitment we’re both making to each other. If we meet every other week, the rate is $2,000. If we meet every week, then the rate is $4,000. On occasion, I will make exceptions to the rate depending on your company stage.
What happens if one of us has to cancel a meeting?
Baked into the retainer is an assumption that life happens and sometimes you’ll need to cancel a meeting and other times you’ll want to meet more often than our regular schedule. So let’s say you have to cancel a meeting because an investor call took priority. We will do our best to reschedule the meeting but if we can’t, the retainer does not change. On the other hand, let’s say we just met two days ago but you have a big meeting coming up and you want to spend 30 minutes getting your head in the right place, we can do that. The retainer allows us to account for both last-minute cancellations and needing extra support.
In the case of prolonged breaks, such as vacations, then billing is prorated to reflect that.
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!
What if I already have others to support me?
Great question! If you already have people like a cofounder, peers, or a mentor that are making you feel sufficiently supported, then hiring a coach might not make sense for you. On the other hand, sometimes even these types of relationships might leave you feeling like there’s a gap. Having me as a coach means you’ll have someone dedicated to your growth and your agenda, someone who will push you and find every way possible to help you grow.