Hill Holm Leadership Library
Leadership guides
Practical answers to the real questions founders, CEOs and executives face — each guide connects you to the workbook that helps you act.
- workbook
When Founder Decisions Feel Like Guessing: A Practical Way to Choose
You do not need certainty to make a sound founder decision. Define the outcome, identify the assumptions that matter, and choose a bounded next step that produces useful evidence without putting the business at unnecessary risk.
Read guide - coaching
New CEO in Australia? Choosing Executive Coaching for Your First 100 Days
A practical guide to choosing an executive coach in Australia, setting priorities for your first 100 days as CEO, and exploring Jessica Hill Holm’s 1:1 executive coaching.
Read guide - workbook
Performance Feedback That Protects Trust and Encourages Improvement
A practical guide from executive coach Jessica Hill Holm for founders and CEOs who want to address performance problems clearly, support improvement, and preserve strong working relationships.
Read guide - workbook
Feedback That Moves Performance Forward and Keeps Trust Intact
Address performance issues with clear observations, honest curiosity, and an agreed improvement plan. This practical guide helps founders and CEOs hold people accountable without making feedback feel like a personal attack.
Read guide - coaching
Executive Coaching for Founders and CEOs in the United States: A Buyer’s Guide
A practical guide to choosing executive coaching in the United States, preparing for a useful first conversation, and exploring Jessica Hill Holm’s 1:1 support for founders and CEOs.
Read guide - workbook
When Your Calendar Caps Revenue: Sharing Customer Ownership
To grow beyond your availability, transfer customer relationships and decision authority—not just meetings. Make your judgment teachable, give your team clear boundaries, and stay connected without remaining the default closer.
Read guide - workbook
How to Step Back From Customer and Product Decisions Without Losing Touch
Removing yourself as the company’s bottleneck does not mean disconnecting from customers or product strategy. It means making your judgment transferable, giving leaders clear decision authority, and replacing constant involvement with focused visibility.
Read guide - coaching
CEO Coaching in Sweden: A Practical Guide to Choosing Your Support
What to look for in CEO coaching in Sweden, how to assess fit, and how to explore Jessica Hill Holm’s 1:1 executive coaching.
Read guide - coaching
Finding an Executive Coach Who Understands Startup Founder Life
A coach’s firsthand founder experience can be valuable, but it is not enough on its own. Learn how to verify relevant experience, assess coaching skill, and choose someone who understands startup pressures without imposing their own playbook.
Read guide - workbook
When Perfect Keeps You Stuck: A Founder’s Guide to Taking Action
Overcoming perfectionism paralysis does not mean abandoning high standards. It means matching effort to risk, defining what is good enough before you start, and taking smaller steps that generate real feedback.
Read guide - coaching
Leadership Team Conflict in Denmark: Choosing Executive Coaching That Fits
A practical guide for CEOs and founders in Denmark who want to address leadership team conflict, choose the right kind of support and explore Jessica Hill Holm’s 1:1 executive coaching.
Read guide - workbook
Get the Project Out of Your Head: A Simple Work System for Founder-Led Teams
A tiny team does not need enterprise project management. It needs a shared place for priorities, clear ownership, visible next steps, and a short review rhythm. This guide explains how to build that structure without making the founder its full-time administrator.
Read guide - workbook
How to Build Team Ownership Without Constant Follow-Up
Real ownership grows when people have clear outcomes, decision-making authority, and a predictable accountability rhythm. Here is how founders and CEOs can replace chasing and rescuing with a practical system that develops independent leaders.
Read guide - workbook
Before the Meeting: Preparing for a Difficult Conversation with an Employee
A practical approach to preparing for a difficult employee conversation: choose appropriate support, separate facts from assumptions, plan a clear opening and agree meaningful follow-up.
Read guide - workbook
Empowering Accountability: How to Get Your Leadership Team to Take Ownership
A practical guide for founders and CEOs on shifting from a culture of dependency to a culture of ownership using the Three Rs framework.
Read guide - coaching
Why Every Decision Goes Through Me as CEO: Breaking the Bottleneck with the Three Rs
A guide for founders and CEOs who have become the central bottleneck in their organization, offering a practical framework to shift from reactive micro-management to scalable leadership.
Read guide - coaching
Why Every Founder Feels Lonely at the Top and How to Reconnect
Loneliness is an inherent part of the founder journey, but it doesn't have to lead to isolation or burnout. This guide provides a practical framework for CEOs to move from professional solitude to meaningful connection and clarity.
Read guide - coaching
Scaling Strategy: When to Hire Your First Executive as a Startup Founder
A practical guide by Jessica Hill Holm on identifying the operational and psychological tipping points that signal it is time to transition from a solo leader to a leveraged executive team using the Three Rs method.
Read guide - coaching
Signs of Founder Burnout and What to Do About Them: A Practical Recovery Guide
Building a high-growth company is inherently high-pressure, but chronic burnout is not a requirement for success. This guide outlines the psychological and physical warning signs of founder exhaustion and provides a structured framework—Reflect, Realign, Redesign—to help leaders recover their momentum and lead effectively.
Read guide - coaching
Scaling Beyond the Self: How to Build a Leadership Team as a Founder
A practical guide for founders transitioning from operational doers to strategic leaders by building a high-capacity leadership team through Reflection, Realignment, and Redesign.
Read guide - workbook
Giving Constructive Feedback Without Putting Trust at Risk
You don’t need to choose between honest feedback and a positive relationship. A clear, respectful conversation helps founders and CEOs address performance concerns, understand what is getting in the way, and agree on practical next steps.
Read guide - coaching
Strategic Thinking for First-Time SaaS CEOs: Resources, Practice, and In-Person Coaching
A practical guide to finding strategy resources, applying them to a SaaS business, and choosing in-person coaching that strengthens your judgment as a first-time CEO.
Read guide - coaching
Your First 100 Days as CEO in Germany: A Practical Guide to Executive Coaching
What to look for in an executive coach in Germany, how to approach your first 100 days as CEO, and how to explore working with Jessica Hill Holm.
Read guide - workbook
Breaking Perfectionism Paralysis: A Founder’s Guide to Moving Forward
Overcoming perfectionism paralysis does not mean lowering your standards. It means matching your effort to the stakes, defining what is good enough before you start, and taking smaller actions that produce useful feedback.
Read guide - coaching
Finding the Right Executive Coach for Founders and CEOs in India
A practical guide to choosing an executive coach in India, assessing fit and turning leadership challenges into focused coaching goals. Meet Jessica Hill Holm and explore her 1:1 executive coaching.
Read guide - coaching
From Founder-Led Sales to a Revenue Engine Your Head of Sales Can Own
Giving your first Head of Sales ownership takes more than handing over deals. Define the mandate, transfer founder knowledge, establish decision rights, and create a phased handoff that makes the new leader accountable without leaving them unsupported.
Read guide - coaching
CEO Coaching in Luxembourg: What to Look For and How to Begin
A practical guide to choosing CEO coaching in Luxembourg, preparing for a useful first conversation, and exploring Jessica Hill Holm’s 1:1 executive coaching.
Read guide - coaching
Is $14,000 a Year for Founder Coaching Worth It Before Revenue?
Coaching can help first-time founders improve decisions, address co-founder friction, and build leadership habits. But before revenue, a $14,000 commitment should depend on your runway, specific needs, coach fit, and evidence of progress—not a promise to avoid years of mistakes.
Read guide - coaching
Executive Coaching for Leadership Team Conflict in the United Kingdom
A practical guide for UK founders, CEOs and executives choosing coaching to address leadership team conflict, with steps to clarify the disagreement and prepare for a more productive conversation.
Read guide - workbook
Overcoming Perfectionism Paralysis as a Founder
Perfectionism can turn high standards into stalled decisions. Learn how to define what is good enough, limit unnecessary revision, and take responsible action without waiting for certainty.
Read guide - workbook
Preparing for a Difficult Employee Conversation: A Practical Guide for Leaders
Prepare for a difficult conversation with an employee by separating facts from assumptions, defining a fair outcome and planning how to listen. This guide also explains what leaders in Norway should look for when choosing support.
Read guide - workbook
Addressing Performance Issues Without Undermining Trust
Constructive feedback works best when leaders name the performance gap clearly, listen before drawing conclusions, and agree on practical next steps. You can protect the relationship without lowering expectations.
Read guide - coaching
Your First 100 Days as CEO in Finland: Choosing an Executive Coach
A practical guide to choosing an executive coach in Finland, setting priorities for your first 100 days as CEO, and exploring whether Jessica Hill Holm is the right fit.
Read guide - workbook
How to Deal With Founder Burnout Without Putting Yourself Last
Founder burnout needs more than a weekend off. Reduce immediate pressure, restore basic recovery, and change the responsibilities and expectations that keep exhausting you.
Read guide - coaching
Executive Coaching for Founders and CEOs in Belgium: Finding the Right Fit
A practical guide to choosing an executive coach in Belgium, preparing for a useful first conversation and exploring Jessica Hill Holm’s 1:1 coaching for founders, CEOs and executives.
Read guide - workbook
How to Delegate Customer Conversations Without Losing Customer Trust
When revenue depends on your availability, growth has a calendar ceiling. Build a team that can lead customer conversations, make sound decisions, and maintain trust without routing every next step through you.
Read guide - coaching
Choosing an Executive Coach for Founders and CEOs in Singapore
A practical guide to choosing an executive coach in Singapore: what to assess, how to prepare and whether Jessica Hill Holm’s 1:1 executive coaching is the right next step.
Read guide - box
Choosing a Leadership Development Gift for Executives and Teams in Finland
A practical guide for buyers in Finland choosing a meaningful leadership development gift for an executive or leadership team, with guidance on relevance, participation and purchasing checks. Discover Jessica Hill Holm’s work and register interest in The Leadership Impact Box®, on a waitlist for Q4 2026.
Read guide - workbook
Solo Founder Burnout: How to Reduce Pressure and Recover
Dealing with burnout as a solo founder requires more than a weekend off. Reduce immediate demands, protect your capacity, bring in support, and redesign the work so recovery does not depend on the business becoming easier.
Read guide - Difficult Conversations
Difficult Conversations Training for Executives
A strategic framework for senior leaders to navigate high-stakes conflict and performance gaps while maintaining high-trust organizational culture.
Read guide - Decision Making
Executive Decision Framework: Moving from Hesitation to Clarity
A guide for CEOs and founders on reducing the cognitive load of high-stakes choices through structured strategic frameworks.
Read guide - Founder Growth
Scaling Beyond Self: The Founder to CEO Transition Velocity
A strategic framework for founders navigating the difficult shift from hands-on execution to high-leverage leadership.
Read guide