coaching

Starting as CEO in the United States: Coaching for Your First 100 Days

A practical guide to choosing an executive coach, setting early leadership priorities and exploring Jessica Hill Holm’s 1:1 executive coaching.

By Jessica Hill Holm · Hill Holm Leadership Library

What to look for in a first-100-days executive coach

Your first 100 days as CEO are not a test of how quickly you can change everything. They are a period for understanding the business, agreeing your mandate and establishing how you will lead. An executive coach can provide space to examine decisions before pressure turns them into rushed commitments.

If you are looking for an executive coach as a new CEO in the United States, start with your actual situation. An internal promotion, an external appointment and a founder taking on a more formal CEO role create different challenges. Choose support that addresses yours rather than a standard transition checklist.

Look for these qualities:

  • A clear working focus: Can the coach help you define the leadership questions you want to address, rather than promising a successful transition?
  • Constructive challenge: Will they question your assumptions without taking over your decisions?
  • Explicit confidentiality: If the company pays, agree what, if anything, will be shared with the board or another sponsor.
  • Practical arrangements: Confirm availability across your US time zone, session format and any expectations about contact between sessions.
  • Appropriate boundaries: Coaching should not replace legal, employment, financial or clinical advice.

Ask how coaching differs from advisory work. Both can be useful, but you should know when someone is helping you develop your judgement and when they are offering a recommendation.

Start with the mandate, not a transformation announcement

Before setting out an ambitious plan, clarify what you have been appointed to do. Ask the board chair, owners or relevant sponsors: What must improve? What must be preserved? Which decisions are mine, and which require consultation or approval?

Write a one-page mandate covering priorities, constraints, decision authority and unresolved questions. Where expectations conflict, surface the disagreement rather than privately trying to satisfy everyone.

For a US-based business, governance and employment questions may require qualified advisers familiar with the company’s structure and relevant jurisdictions. A coach can help you prepare the conversation, but should not substitute for that expertise.

Days 1–30: listen with a consistent set of questions

Meet direct reports, key stakeholders and people close to customers and delivery. Use a few repeated questions so you can compare perspectives:

  • What is working that I should avoid disrupting?
  • Where do decisions or execution repeatedly stall?
  • What are we reluctant to discuss?
  • What would you need from me to do your best work?

Separate observations from interpretations. A missed deadline is an observation; “this team lacks accountability” is an interpretation that needs testing.

Keep a decision log with three categories: act now, investigate and revisit later. Urgent risks still need attention, but not every concern requires an immediate reorganisation. Coaching can be a place to examine why a particular issue makes you want to intervene quickly.

Days 31–60: narrow the priorities and clarify ownership

Turn what you have learnt into a small number of priorities. For each, agree the intended outcome, accountable owner, decision boundaries and review date.

Avoid becoming the new approval point for every difficult choice. Ask your leadership team which decisions they can own and what information or authority they need. Make escalation expectations explicit.

This is also the time to address gaps between your expectations and current performance. Prepare with evidence, explain the impact and hear the other person’s perspective before agreeing next steps. Do not use the first-100-days deadline as a reason to bypass a fair process.

Days 61–100: review progress and establish a sustainable rhythm

Review your early assumptions with the leadership team and board. What have you learnt? Which priorities still hold? What needs to change?

Establish a rhythm for decisions, performance reviews and stakeholder communication. Assess your own behaviour too: Are you delegating authority, or only tasks? Are people bringing you uncomfortable information? Does your calendar reflect your priorities?

For coaching, choose observable progress markers such as clearer decision ownership, completed conversations or protected strategic thinking time. These are more useful than expecting coaching alone to produce business results.

Who Jessica Hill Holm is and why she may fit

Jessica Hill Holm, of Hill Holm Leadership, is an Executive Coach & Advisor whose work centres on building and transforming innovation-driven companies alongside CEOs and founders, with a focus on People & Culture.

That focus may be relevant if your transition involves organisational change, leadership-team relationships or moving from personal involvement towards shared ownership. It is a reason to explore fit, not a guarantee of outcomes or evidence of a particular US transition track record.

You can review her LinkedIn profile and use an introductory conversation to discuss your context, expectations and practical arrangements.

Explore Jessica’s 1:1 executive coaching

Bring one live challenge: an unclear mandate, a difficult leadership conversation or a decision you keep postponing.

Book a free 30-minute discovery call to explore Jessica’s 1:1 executive coaching. Or talk to her AI advisor on this page right now to begin clarifying what support you are looking for. Avoid sharing confidential company or personal information with the AI advisor.

Frequently asked questions

When should a new CEO start executive coaching?
Before taking the role can be useful for clarifying expectations. Starting during the first 100 days can also help when real leadership challenges emerge. Choose timing around your needs rather than an arbitrary deadline.
Does a coach need to be based in the United States?
Location alone does not establish fit. Check time-zone compatibility, understanding of your organisational context and boundaries around jurisdiction-specific advice. Confirm Jessica’s availability and working arrangements directly.

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