The AI Questions CEOs Should Ask to Avoid the Wrong Executive Hire

Most CEOs know something’s not working — but they can’t always articulate what they need, or who they need in the seat.

Enter Artificial Intelligence.

Lately, we’ve noticed more CEOs coming to us with excellent summaries of their business situation — often generated with AI. Honestly? We love it. A clear brief = faster, better match to the right interim leader.

The worst place to be as a CEO is knowing something is off… but not being able to name it.

AI helps you find the language.

A proven interim executive helps you fix the problem.

This guide (written with the assistance of AI!) gives you the exact ChatGPT prompts you need to help clarify:

  • your situation
  • your problems
  • the outcomes you want
  • whether you need an interim, fractional, or full-time leader

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Virtual CFO vs. Interim CFO: Why Leadership, Not the Label, Determines Outcomes

On paper, a virtual CFO looks like the fastest solution to a financial leadership gap. In practice, many executives discover too late that what they hired is a service, not a leader. When your company faces investor scrutiny, cash pressure, or a pivotal transition, the real decision executives face isn’t virtual versus in-house, it’s transactional support versus decisive leadership.

InterimExecs CEO Robert Jordan discussed the differences — and asked for insights on when an embedded CFO is the right move — in conversations with two successful interim Chief Financial Officers, Vic Datta and Mike Winer. Here’s what their years of experience have taught them.

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Expanding and Scaling Your Company: The Growth Interim’s 4-Part Success Strategy

When a company reaches the point where momentum alone can’t sustain growth, it often faces the hard truth: the systems, people, and leadership that got it here may not get it there. That’s where a growth interim steps in — to stabilize, realign, and set the stage for sustainable expansion.

Whether you’re running a manufacturing business or scaling an SaaS company, the principles of disciplined growth remain the same. You must assess what’s working, fix what’s broken, and put the right leadership in place to grow without losing quality or direction.

Below, veteran growth interim Charlie Shalvoy shares the four success stages that help organizations scale strategically — and what to do when the CEO can’t scale the company alone.

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The Downside of Management Consultants and Why Interim Executives Deliver Results

Market volatility, supply chain disruptions, and rapid technological change have left many companies in need of effective leadership. Often, those companies turn to consultants for instant help. But they continue to struggle. Why? Because consultants strategize and deliver impressive decks. But they don’t stick around to turn those ideas into results.

What those companies really need is an effective leader who can strategize, AND deliver results. And they need it now.

The answer is a rock star interim executive who can be on-site, taking charge and making progress in as little as 48 hours.

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What is the Role of an Interim CIO? 5 Common Use Cases

In today’s fast-moving, tech-driven business environment, the role of the CIO is more critical — and more complex — than ever. Whether your organization is navigating digital transformation, merger integration, or large-scale ERP system upgrades, an Interim Chief Information Officer (CIO) can deliver immediate, strategic value without adding long-term overhead.

(Learn more about our Interim CIO Services and Fractional CIO Services here.)

Unlike consultants or rising IT managers, a seasoned interim CIO brings deep operational and leadership experience. These executives are not only capable of taking on the same responsibilities as a permanent CIO, but they also offer a focused lens on change, transformation, and rapid results.

Here are 5 common use cases where an interim CIO can be a powerful asset to tackle high-impact technology initiatives, IT leadership gap coverage, or specialized project execution:

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Fractional vs. Interim Executives: What Are the Differences and Which is the Right Path?

Interim and fractional leadership lies at the intersection of leadership gaps and the gig economy. They are the answer to the challenges organizations face in today’s dynamic business landscape. But what are the differences between the two approaches and which one is right for your organization? And which is the right future career path for you as a high-level executive?

Let’s break it down.

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Top 5 Qualities of a Great Interim CIO

When technology stalls or transformation fails, it’s rarely because of tools or code. More often, the root issue is leadership — misaligned, ineffective, or stuck in the weeds.

That’s where interim CIOs step in. The best ones don’t just manage systems. They stabilize teams, reset direction, and accelerate outcomes — often under immense pressure and tight timelines.

At InterimExecs, we work with elite interim leaders across the globe through our RED Team. We sat down with some of our top-performing interim and fractional CIOs to understand what separates the good from the truly great.

Here’s what we found:

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Guide to Hiring a Fractional CFO: What to Know Before You Make the Call

Hiring a fractional CFO could be one of the most impactful decisions you make this year. Whether your company is preparing for growth, managing a complex financial challenge, or gearing up for fundraising, a seasoned financial leader can bring clarity and direction — without the overhead of a full-time hire.

In this guide, we break down when to bring in a fractional CFO, what to expect, how to choose the right one, and how InterimExecs can match you with a RED Team leader who’s ready to make an immediate impact.

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When Does it Make Sense to Structure an Interim Gig as a Statement of Work Contract?

One of the hottest trends in the hot market for interim executives is structuring interim engagements as a “statement of work” contract. Here, we take a deep dive into this trend and look at when it makes the most sense for a company to negotiate a statement of work contract, when it makes the most sense for an interim, and when it simply doesn’t make sense for either.

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