Chemistry Matters: The Right Questions to Ask When Interviewing an Interim Executive

At InterimExecs, we’ve spent years developing a proven methodology for matching companies with experienced interim executives. While skills, experience, and track record matter, one factor consistently rises to the top of the list: chemistry.

Whether the interim executive will be working with a private equity fund, a company owner, a board, or an existing management team, alignment and trust are essential. Once we recommend an executive—or team—tailored to a company’s needs, the next question almost always follows:

“What should we be asking in the interview to know if this is truly the right fit?”

Below are several targeted interview questions designed to help you assess both capability and chemistry—so you can move forward with confidence.

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8 Questions to Ask to Decide Whether Your Family Office Would Benefit from Interim, Long Term Fractional, or Outsourced  Leadership

When families begin to question whether their office is operating as effectively as it should, the challenge is rarely a lack of commitment — it’s a lack of perspective. The eight questions below are designed to prompt an objective review of leadership effectiveness, cost alignment, and governance clarity, and to help determine whether temporary leadership support could be valuable without forcing permanent decisions.

1. Are rising family office costs clearly tied to measurable value?

 If operating expenses have increased but performance, transparency, or peace of mind have not improved proportionally, it may be time for an objective operational review by an interim executive. The right ongoing answer might be a fractional executive so you can get all of the firepower of an experienced leader at far lower cost.

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Using AI Without Exposing Your Crown Jewels: A Practical Guide for C-Suite Leaders

Artificial intelligence has moved from “interesting experiment” to “board-level priority” with remarkable speed. Most CEOs and executive teams now believe AI can materially improve efficiency, decision-making, and growth. At the same time, many share a quieter concern:

How do we use AI safely so we don’t put our most sensitive data, IP, and competitive advantage at risk?

The good news is that companies can unlock real value from AI without putting proprietary information at risk — and they can do so without rushing into a costly, permanent hire before they’re ready.

Here’s how.

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Boards Must Lead on Technology Oversight: From Risk to Strategic Growth

In an age of AI disruption, ransomware attacks, and cloud dependency, boards of directors face a new kind of fiduciary responsibility: ensuring that technology risk is understood, governed, and turned into competitive advantage.

Without active board engagement, companies risk falling behind—or worse, facing catastrophic loss. But when boards get technology right, it opens the door to innovation, security, and sustained value creation.

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When and How to Divest: A Guide to Strategic Spin-Offs and Carve-Outs

The strategic playbook of most companies focuses on growth through mergers and acquisitions. But that focus on M&A deals overlooks one of the most powerful tools in their arsenal: a clear, proactive divestiture strategy. The strategic shedding of underperforming assets can be a robust engine for value creation and an essential component of dynamic portfolio management for boards, C-suite executives, and private equity funds.

“While there’s plenty of evidence to suggest divestitures can create more value for shareholders than acquisitions, only about 30% of S&P 500 firms engage in them annually,” says Emilie Feldman, professor of management at Wharton and author of Divestitures: Creating Value Through Strategy, Structure, and Implementation.

This underutilization, she posits, is partly due to a psychological bias: “M&A is associated with positive terms like ‘growth’ and ‘opportunity,’ while divestitures are linked to negative terms like ‘failing’ and ‘lagging.'”

Overcoming this misperception is critical to unlocking substantial enterprise value.

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How to Build a Better Board of Directors in 4 Easy Steps

“A world of no surprises.” That is the lofty goal of private equity investors Eli Boufis and Steve Thompson when they take on a new company. It involves open communication with the CEO – including reminders of how much money they can make if the acquisition succeeds – and a plan to build a better board of directors.

Building a better board of directors is a four-part process:

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The Low-Hanging Fruit for Fixing a Poorly Performing Board of Directors

Much has been written about board governance best practices. Much less information is available to help you figure out how to fix a board that isn’t delivering peak performance.

InterimExecs CEO Robert Jordan interviewed two experienced private equity investors, Eli Boufis and Steve Thompson, to talk about how to build a better board of directors.

To start, they believe board composition should include independent directors — people who are employed neither by the company nor by the private equity fund — to ensure effective governance. But, they noted, there are six ways independent board members come up short on corporate governance.

Helping them improve on these six issues is the “low-hanging fruit” of improving board effectiveness, they say.

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When it Comes to Sarbanes-Oxley Compliance: Will You Choose a Babysitter or a Change Agent?

You’re on a public company board and the phone rings at midnight and it’s not good news: Your CEO or CFO has passed away. The next morning, the board convenes in emergency session. There’s only one subject beyond condolences for the tragic passing: Who is going to step into the interim CEO or CFO role?

Will you choose a placeholder from among your board, or will you choose to do something more proactive?

Let’s dive into the options.

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Private Company Governance: Why You Need a Strong Board of Directors

Bruce Werner has a blunt message for company owners. “Owners are leaving money on the table. They’re not getting full value from their boards,” he says. “We can improve the outcomes in your business, make your life a little better, and take risk out of the business by having a board do what it ought to. And it doesn’t take that much more effort. You just have to ask a few important questions.”

Werner came up in the family business, a $500 million company that made ladders until it was sold in a leveraged buyout in the mid-90s. After the sale, Werner started, grew, and sold four companies, was a partner in a private equity fund, and served on more than 10 boards, mostly for family-owned firms.

He’s distilled all of that experience into two books, Your Ownership Journey: 12 Secrets for Personal and Business Success, which published in 2022, and Navigating Private Company Governance: The Savvy Business Owner’s Guide to Developing an Effective Board, which published in 2023.

We interviewed him in the wake of the publication of Navigating Private Company Governance and asked him about his advice for business owners wondering whether they need a board of directors for better corporate governance.

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What is an Interim Executive Director and Why Would You Want One?

The concept of an Interim Executive Director (ED) isn’t well-known among nonprofit organizations…yet. But, it’s becoming more mainstream and for many good business reasons.

On average, it takes a Board of Directors 9 months to recruit a new Executive Director. By the time they are on-boarded and contributing, a year may have passed since the departure of the prior nonprofit leader.

While nonprofit board members may step up to “mind the gap,” the truth is that stakeholders — employees, partners, and funders — can lose confidence in your organization during this leadership transition and key employees may leave.

Organizing payroll, developing a budget and/or managing human resources may keep the lights on, but without someone filling the executive director role during the transition period, your organization can be harmed and stymied while the Board is focused on the executive search for a new ED.

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