Navigating change is exhausting.

Whether you are struggling with burnout, attempting to meet ambitious goals, or just trying to balance personal energy, it’s easy to feel link you aren't doing enough. Coaching helps individuals gain clarity, navigate uncertainty, and build habits that actually stick.

How We Work

Boss Insights offers individual coaching as well as peer support and team strategies to create sustainable, lasting impact.

  • Start with your goals—overcoming burnout, building resilience, or creating sustainable systems.

  • Leverage your strengths and address what’s holding you back.

  • Test new strategies with built-in accountability and reflection.

Our Philosophy

You cannot out-plan burnout. And you cannot earn your rest by working harder.

I often tell a story about my own burnout journey. I thought if I just changed jobs—found a better title, a new contract—everything would feel easier. But the grass wasn't greener, because the gardener hadn’t changed. 

My coaching practice is a container for that change. We stop looking for the "right" answer and start looking at your compass. 

  • We make space: To name what actually matters to you right now (not five years ago). 

  • We tend the roots: We look at your boundaries, your capacity, and your "quiet signals." 

  • We build structure: Because sustainable growth requires a trellis, not just sunshine.

An iterative, interactive process, tailored to exactly what you need. You will work with Boss Insights founder Whitney Kippes one-on-one to dig into root challenges, leverage your existing strengths, and test new strategies with built-in accountability.

Our Offerings

Choose the path that best suits you (or talk to Whitney about a custom program).

Strategy Session

For anyone who needs a little extra support.

Duration: Single Session

Includes:

  • 1 x 1:1 coaching sessions (50 mins, via Google Meet)
  • Body doubling, advice, and supportive coaching from Boss Insights founder Whitney Kippes

Investment: Pay what you can ($175 minimum, $245 recommended)

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The Launch Sprint

For the professional ready to make it official.

Duration: 2-4 Weeks

Includes:

  • 2 x 1:1 sessions including a strategic mapping call and a live body-doubling registration sprint to cross the finish line
  • Customized entity setup guidance tailored to your specific location, legal structure, and professional goals
  • Support to finalize your business name and domain availability ensuring your brand has a clear and ownable digital home
  • Curated resources and worksheets for immediate use
  • Bonus: Six week entry membership in the Bosscraft Consultant Network for peer support as you launch ($40+ value)

Investment: $449

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The Supported Boss

For the consultant ready to redesign their practice.

Duration: 2-4 Months

Includes:

  • 3 x 1:1 coaching sessions designed as a series of deep dives to untangle your service model and check your compass
  • Comprehensive service ecosystem audit to identify and prune draining tasks while centering your "zone of genius"
  • Live rate and capatiy review to audit your pricing against your actual metrics of "enough"
  • Curated Resource Library: Access to the Sustainable Rate Setting, Service Area Builder, and Ideal Week workbooks (and more!)
  • Bonus: Three month membership in the Bosscraft Consultant Network ($80+ value)

Investment: $659 (or 3 payments of $235)

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The Lead Cultivator

For the freelancer ready to end the "boom or bust" cycle.

Duration: 4-6 Months

Includes:

  • 4 x 1:1 coaching sessions dedicated to dismantling the "pitchy" ick and building a sustainable visibility ritual
  • Customized outreach and messaging framework through collaborative drafting of scripts and templates that actually sound like you
  • Strategic pipeline and community mapping to identify your natural connectors and high-fit client profiles without the hustle
  • Real-time navigation support via one month of asynchronous pitch review through Email or WhatsApp
  • Resource Library: Access to the Client Brainstorm, Lead Cultivation Workbook, the Art of Lead Cultivation course and Client Brainstorm guides
  • Bonus: Six month membership in the Bosscraft Consultant Network ($160+ value)

Investment: $949 (or 4 payments of $250)

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The Transformation

For the professional ready to change the way they work entirely.

Duration: 6-12 Months

Includes:

  • 9 x 1:1 coaching sessions delivered biweekly or monthly via Google Meet to facilitate deep behavioral change and long-term career architecture
  • Deep-dive leadership style assessment & ecosystem audit to move beyond immediate fires and build a practice that fits your actual life
  • Unlimited asynchronous support via WhatsApp or Email for real-time navigation and guidance between scheduled sessions
  • Full Resource Library access to all relevant Boss Insights worksheets & tools
  • Bonus: One year membership in the Bosscraft Consultant Network, if applicable ($300+ value)

Investment: $1,985 (or 4 payments of $515)

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Executive & Organizational Partnership

For teams that need to stabilize, navigate intense pivots, or retain high-potential talent.

If your organization is feeling the squeeze—ambitious goals but limited resources—I partner with leadership teams to rebuild systems that sustain the people doing the work.

Customized Program:
  • Engagement and support to encourage sustainable growth and professional development
  • Ad-hoc crisis support, including priority scheduling
  • Triad intake and conclusion meetings with you, your manager, and/or HR to harmonize goals (optional)
  • Confidential quarterly progress reports
  • Full suite of assessments and tools

Investment: Custom / Retainer-based

Schedule a Consultation

Book Your Free Exploratory Session

Book now

Who We Work With

  • Individuals

    Get support where it matters most—navigating burnout, clarifying your next move, and building sustainable leadership habits. Individual coaching helps you grow with intention and confidence.

  • Freelancers

    Work 1:1 or connect with other freelance consultants in the Bosscraft Consultant Network. Build authentic connections with peers, share experiences, and gut check your strategies with folks who really get it.

  • Organizations

    Retain your best talent engaged and thriving. Our coaching helps purpose-driven organizations cultivate talent, build trust, and create an organizational culture that makes people want to stay.

Real Words from Real Clients

Whitney is very good at shedding new light on something I may have already closed the door on mentally, and encouraging me to think longer and harder about things. She is a very good listener and can take what I say and synthesize it into more sensible language so that I understand my own foggy brain more clearly.

My supervisor immediately noticed my growth and confidence and my enhanced performance. It influenced my personal life in feeling more empowered and leaning more into my values that define me as a being - outside of my work.

By Session 3/6, I felt like I had accomplished so much. I identified my goals that were important for me to accomplish, I received the transformation coaching, I put the work in, and I am experiencing a renewed sense of power.

Whitney's ability to listen to her clients, not just hear them, but actively listen. She is very present and helps you to reframe perceived weaknesses to reveal actual strengths, thus making her clients feel more empowered and in control.

Life-wise, I also feel like I benefited because I feel more confident saying no to opportunities that don't clearly align with my values or ambitions. I also just generally feel more well-rounded and knowledgeable and have been able to pass that knowledge on to other peers and colleagues which has been very helpful.

FAQ

  • What is executive coaching?

    Coaching is an iterative, interactive process designed to help you make concrete changes to support your goals—both personal and professional. We help our coaching clients achieve their goals through powerful conversations that are intended to navigate to the root of challenges, inspire new thinking, and support the achievement of goals.

    Executive coaching can also be offered to staff in support of overall professional development, performance improvement, or retention goals. If you would like to provide coaching to your staff, email [email protected] directly.

  • Who can benefit from coaching?

    Leaders, freelance consultants, and mission-driven organizations can all benefit. Coaching supports anyone looking to prevent burnout, gain clarity, strengthen their team, or grow their business sustainably. Whitney's experience makes her exceptionally well suited to freelancers and individuals working in the humanitarian, international development, and social impact sectors.

  • How long does the coaching engagement last?

    Coaching is flexible. Some clients start with a single session to get unstuck, others engage in multi-session packages (like a 6-session program) or ongoing support for longer-term growth. Your coach can help you determine what support is right to meet your goals.

  • How often would I met with my coach?

    We recommend meeting with your coach once per week or every two weeks. Over many years, we've found that this frequency helps us maintain momentum and make lasting change happen.

  • Are sessions virtual or in-person?

    Individual coaching sessions are all conducted virtually using Zoom or Google Meet to ensure multiple options to connect. We also offer onsite sessions for teams and organizations where needed.

    Our Boss-to-Boss Consultant Network meet virtually in a private online community and in regularly scheduled virtual meetings.

  • What about confidentiality?

    Absolutely. Every coaching relationship is private and governed by professional ethical standards, so you can explore challenges openly and safely. Even when working in partnership with a corporate sponsor, we insist on confidentiality.

  • How much does coaching cost?

    We recommend starting individual coaching (after an initial consultation to confirm your coach is a good fit) with sessions priced on a sliding scale. Financial aid and scholarships may be available to those who qualify. If you are interested in financial aid, please contact [email protected].

  • How do I get started?

    Click any button on this page to schedule an initial consultation. We’ll discuss your goals and recommend the coaching approach that fits your needs, whether individual sessions, peer network membership, or team coaching.

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