Frequently Asked Questions

Real questions from sales leaders. Straight answers from someone who's been there.

THE TOP 5 BIG QUESTIONS

These are the most common questions I hear from sales leaders.

Expand to see answers to these questions

  • Here's what I can tell you: I've coached frontline managers with 3 reps, VPs with 200+ people, and individual contributors trying to break into leadership. Every situation is different.

    What makes coaching work isn't a one-size-fits-all formula. It's the combination of:

    • Your willingness to be honest about what's really happening

    • A structured process that creates clarity and accountability

    • Consistent action between sessions (not just talk therapy)

    I don't promise magic. I promise a framework, tough questions, and someone who won't let you off the hook when you make excuses.

    The proof? I offer reference calls with current and former clients. Talk to people who've been in your shoes. Ask them if it worked. Make your own decision.

  • This is the #1 question I get in LinkedIn DMs and emails. And it's the most important one.

    If you've been laid off or you're worried about the next RIF, you're dealing with more than just "updating your resume." You're questioning your identity, your value, your path forward.

    Here's what I help with:

    1. Reset Your Vision

    • What do you actually want next? (Not just "any job"—the RIGHT job)

    • What matters to you now that didn't matter before?

    • What are your non-negotiables?

    2. Career Transition Coaching

    • Interview preparation and positioning

    • Navigating offers and negotiations

    • Building a compelling narrative about your career

    • Identifying companies and roles that align with your values

    3. Rebuilding Confidence

    • Processing what happened without letting it define you

    • Reframing your story as growth, not failure

    • Moving from "I lost my job" to "I'm choosing what's next"

    In the past year alone, I've helped 5 sales leaders find new roles at companies that align with their values and career goals. Not just "a job"—the RIGHT job.

    If this is you right now: Let's talk. Free 30-minute strategy call. No pitch. No pressure. Just an honest conversation about where you are and what's next.

  • I don't want to take your money if coaching isn't going to work for you. Here's when coaching fails—and when you should look for something else instead:

    Coaching doesn't work when:

    1. You're not ready to change If you're hoping I'll validate your current approach or tell you everyone else is the problem, we're not a good fit. Coaching requires you to look in the mirror and be willing to do things differently. If you're defensive, resistant, or unwilling to be uncomfortable—save your money.

    2. You're looking for a quick fix Real transformation takes time. If you think 2-3 sessions will solve a years-long pattern, you're going to be disappointed. Most clients see meaningful progress in 90 days, but only if they put in consistent work between sessions.

    3. You want someone to tell you what to do That's consulting, not coaching. If you want a playbook or someone's "proven system," hire a consultant or find a mentor. Coaching helps YOU figure out what's right for YOUR situation. If you're not willing to think for yourself, this won't work.

    4. You won't do the work between sessions The magic doesn't happen during our hour together—it happens when you're applying what we discuss in the real world. If you're not going to test new approaches, collect feedback, and try uncomfortable behaviors between sessions, you're wasting both our time.

    5. You need therapy, not coaching Coaching is forward-focused. If you're dealing with deep psychological issues, trauma, clinical anxiety/depression, or need to process past experiences to heal—you need a licensed therapist, not a coach. I'm not a counselor, and I won't pretend to be one.

    6. You're being forced into it If your company is making you do this or your spouse is pushing you—and YOU don't actually want to be coached—it won't work. Coaching only works when the motivation comes from within.

    7. You have unrealistic expectations If you're expecting guaranteed results, instant transformation, or for me to do the hard work for you—we're not aligned. I provide a framework, tough questions, and accountability. YOU provide the effort and commitment.

    When coaching DOES work:

    • You're self-aware enough to know you need help but don't have all the answers

    • You're willing to be uncomfortable and challenged

    • You'll commit time and energy to the process

    • You want accountability, not hand-holding

    • You're ready to own your results, not make excuses

    If you're not sure whether coaching is right for you, let's talk. Schedule a free 30-minute strategy call. I'll tell you honestly if I think coaching makes sense for where you are right now—even if that means telling you to come back in 6 months when you're ready.

  • This is exactly why you should hire me.

    Here's the thing: if you hire a coach who's been in your exact role, you're getting their playbook. Their answers. Their biases about "the right way" to do things based on what worked for them.

    An ICF-certified coach doesn't give you answers—we help you find yours.

    Because I haven't been a CRO or CEO, I'm not locked into "here's how I did it" thinking. Instead, I can:

    • Ask questions without assumptions about what you "should" do

    • Help you explore options you might not have considered

    • Challenge your thinking without imposing my experience as the "right" answer

    • Guide you to clarity based on YOUR context, not mine

    Think about it: If you hire someone who's been a CRO at 3 SaaS companies, they're going to coach you based on those 3 experiences. But your company isn't those companies. Your team isn't their team. Your market isn't their market.

    What I bring instead:

    • 25+ years of sales experience (individual contributor to VP)

    • Deep understanding of B2B SaaS sales dynamics

    • ICF training in asking powerful questions and creating clarity

    • No agenda to prove "my way worked, so you should do it my way"

    You don't need someone who's done your job. You need someone who can help you figure out how to do YOUR job better in YOUR situation.

    That's what coaching is. And that's what I do.

  • Great question. Here's the truth:

    I coach evenings and weekends. My day job doesn't interfere with my coaching practice—because I intentionally keep them separate. And honestly? Most busy sales leaders prefer evening/weekend sessions anyway. You can't exactly block your calendar at 2pm on a Tuesday for personal coaching when you've got pipeline reviews and customer calls.

    Conflicts of interest? Everything is confidential. You and I both sign a confidentiality clause tied to the ICF Code of Ethics. Even if our companies are competitors, even if you tell me sensitive information—it stays between us. I'm legally and ethically bound to protect what you share.

    The benefit of my dual role? I'm not coaching from a beach somewhere, writing theory. I'm in the arena right now. I'm dealing with the same pressures, the same board expectations, the same people challenges you are. This week's problem you're facing? I probably dealt with a version of it this month.

    You're not getting someone who used to be a sales leader. You're getting someone who IS one.

Other Common Questions…

Expand to see answers to these questions

  • First and foremost: it's all about you, your objectives, and your goals.

    We don't jump immediately into coaching on the first call. Here's how it works:

    Before Our First Session: When you sign up, you'll receive a comprehensive intake assessment. This isn't a generic questionnaire—it's a thorough document that helps me learn everything about you and what you want to accomplish so I'm fully prepared when we meet.

    Why the intake matters: I need at least 72 hours (ideally a week) to review your intake before our first session. This allows me to come prepared with specific questions and a tailored approach that fits YOUR needs, not a one-size-fits-all program.

    During Sessions:

    • You drive the agenda - We work on what matters most to you right now

    • I ask tough questions - Not to interrogate you, but to help you see what you can't see on your own

    • We create accountability - You leave with clear actions, not just good feelings

    • Between sessions matter most - Real progress happens when you're applying what we discuss

    Between Sessions: This is where the real work happens. You'll be testing new approaches, collecting feedback, trying uncomfortable behaviors. The sessions are where we process, adjust, and plan next steps.

    Bottom line: If you want someone to tell you what to do, you don't need coaching. If you want someone to help you figure out what's right for YOU and hold you accountable to doing it—that's what our sessions deliver.

  • This is exactly why I coach evenings and weekends only. You don't have to sacrifice your workday or family time.

    Missed sessions policy:

    • 24-hour cancellation required - Give me 24 hours notice, and we'll reschedule. No problem.

    • One emergency button per package - Life happens. You get ONE session per package where you can cancel with less than 24 hours notice, no penalty.

    • If you no-show or cancel late (and you've used your emergency) - That session counts as completed toward your package. No refunds, no makeup sessions.

    Why the firm policy? Because accountability starts with showing up. If you're too busy for an hour every other week to work on yourself, your team, and your career—we've already identified the first problem to solve.

  • I don't pretend to know every vertical inside and out. But here's what I do know:

    • B2B SaaS sales dynamics - 14+ years in enterprise software sales leadership

    • What it's like to carry a number and have your job depend on hitting it

    • Managing up, down, and sideways in complex organizations

    • The pressure of forecast calls, pipeline reviews, and board expectations

    • What keeps sales leaders up at night - because I'm living it right now as an active VP of Sales

    I'm not coaching from theory. I'm coaching from the trenches of a 14,500-person Fortune 1000 company.

    Do I need to understand your specific product or customer base to help you? No. The challenges of sales leadership—accountability, forecasting, hiring, culture, performance management—are universal. The frameworks are the same whether you're selling cybersecurity or logistics software.

    If you're skeptical, let's talk. Set up a Free 30-minute strategy call. No pitch. Just a conversation to see if this makes sense for your situation.

  • Many clients continue with ongoing coaching after their initial package. We'll discuss options for continued support during your final sessions, including discounted continuation rates for existing clients.

  • Yes. If you’d prefer to begin with a smaller engagement or want support on a specific leadership challenge. These sessions require no consultation and are designed to give you clarity, momentum, and a taste of what working together looks like.

    I offer two focused one-session options.
    1. The Leadership Impact Session. Choose this if you want targeted support on a specific leadership or performance challenge.
    2. Career Transition Jumpstart. Choose this if you’re navigating a job search, RIF, or interview process and want help strengthening your career story or direction.

  • Yes, everything is 100% confidential.

    Per the ICF Code of Ethics, anything you share with me stays between us—unless:

    1. You give me explicit permission to share something with someone else

    2. You indicate intent to harm yourself or others (the only legal exception)

    We both sign a confidentiality agreement. Your company won't find out unless YOU tell them.

    But what if my company DOES find out?

    This is actually the opposite of what most people think.

    When your company finds out you're investing in professional coaching, it signals:

    • You're serious about growth

    • You're proactive about development

    • You're committed to being better

    • You're the kind of leader who invests in themselves

    It's seen as a POSITIVE, not a negative. Executives get coached all the time. Why? Because high performers want to stay that way.

    That said—if you're in a toxic environment where leadership development might somehow be weaponized against you, everything stays confidential. They won't know unless you tell them.

  • No, I don't guarantee results. Here's why:

    Coaching gives different results to different people in different timeframes. One client increased forecast accuracy by 40% in 3 months. Another took 6 months to land their dream VP role. Another built an accountability framework that transformed their entire org in 4 months.

    The variable isn't the coaching. It's the person.

    I also abide by the ICF Ethics standard which say coaches should not guarantee results.

    What I DO guarantee:

    • A proven framework

    • Tough questions that make you uncomfortable

    • Accountability that doesn't let you hide

    • Someone who's been where you are and knows what it takes

    Want proof? Talk to my clients. I offer reference calls with current and former coachees. They'll tell you what worked, what was hard, and whether it was worth it.

    Most clients realize ROI within the first 90 days. Not because I'm magic, but because clarity + accountability + consistent action = results.

  • Payment methods accepted:

    • Major credit cards (Visa, Mastercard, Amex, Discover)

    • ACH/Bank transfer

    • Debit cards

    • PayPal

    Payment plans available:

    • Pay in full (one-time payment)

    • Monthly installments (available for Core and Premium packages)

    Refund/cancellation policy: Once a package is purchased, there are no refunds or cancellations. You're committing to the work, and I'm committing to showing up. Accountability goes both ways.

    It’s also important to note that all coaching engagements include a clear coaching agreement that is signed by both parties outlining session scheduling, cancellation policy, and terms. We'll review this together during your discovery call to ensure we're a good fit before you commit.

  • Yes, many clients do.

    I provide all documentation needed to support your reimbursement request:

    • Coaching agreement

    • Professional invoices/receipts

    • Certificate of completion

    • Progress summaries (if required by your company)

    • Verification of credentials

    How to approach your company:

    1. Check if you have a professional development budget

    2. Position coaching as leadership development (not "I'm struggling")

    3. Emphasize ROI: improved team performance, forecast accuracy, retention

    4. Submit coaching agreement and receipts according to your company's process

    Need help? I can provide a business case framework and all necessary documentation.

    Want a complete guide? Check out my blog article: [How to Get Your Company to Pay for Executive Coaching] with templates, scripts, and step-by-step instructions.

  • No. Complimentary consultations are reserved for my 3-month coaching packages. The small-bite sessions are designed to be booked directly so you can get support quickly and without extra steps.

Didn’t See your Question? Contact me. I’ll be happy to talk with you.

A man in a gray blazer and blue shirt standing against a stone wall, talking on a cell phone.

Or, skip the back and forth and let’s schedule a complimentary 30 min strategy call. No pitch. No pressure. Just a conversation on whether coaching makes sense for you right now ,

Schedule your complimentary consultation here