25 Strategic Interview Questions To Ask Candidates

With our firm having a front-row seat to thousands of executive interviews across industries, company stages, and economic cycles has taught us one thing: the best interview questions don’t feel like tests. They feel like conversations that unlock something real, something a polished résumé simply can’t show you.

So to mark our 25th anniversary this year, we asked our executive recruiting team to compile our favorite 25 interview questions we have found most insightful.

Mark Sonstein – CIO @ Chugach Electric

Chugach Electric Association, Inc. is Alaska’s largest electric utility, proudly serving more than 90,000 members across Anchorage and northern Kenai Peninsula. As a member-owned cooperative, Chugach Electric is deeply rooted in the communities it serves and committed to delivering safe, reliable, and affordable power while advancing a cleaner and more resilient energy future.

Marty Pearson – SVP, IT Operations & Infrastructure @ NW Administrators

Our Herd Freed Hartz executive search team was honored to partner with Northwest Administrators on a retained executive search to find their new SVP, IT Operations & Infrastructure in Seattle. Since 1958, Northwest Administrators Inc. has been a trusted third-party administrator with a long-standing reputation for delivering accurate, compliant, and member-focused benefit administration services.

Mel Ewing – CTO @ 3 Rivers Communications

Our Herd Freed Hartz executive search team was honored to partner with 3 Rivers Communications on a retained executive search to find their new Chief Technology Officer (CTO) in rural Montana. 3 Rivers Communications is a member-owned telecommunications cooperative providing broadband, VoIP, and related IP-based services to rural communities across central and western Montana.

Amy Spanik – CFO @ Johnstone Supply

Johnstone Supply (The Founders Group) is a leading HVAC/R wholesale distributor that has been serving contractors across the Western United States since 1953. Operating 20 branch locations six Western states, the company stocks products from more than 300 premier brands

Eric Rose – President @ Markey Machine

Our Herd Freed Hartz executive search team was honored to partner with Markey Machine on a retained executive search to find their new President. Since 1907, Markey Machine has been the global leader in the design, manufacturing, and servicing of high-performance marine winches and deck equipment.

Neill Bafus – CFO @ Rottler Manufacturing

Our Herd Freed Hartz executive search team was honored to partner with Rottler Manufacturing on a retained executive search to find their new Chief Financial Officer (CFO).

Rottler Manufacturing is the industry leader in CNC engine machinery and equipment used for remanufacturing engines across the Automotive, Marine, Mining, and Industrial Sectors. This 3rd-generation business has a 100+ year track record of success with its high-precision solutions for boring and honing engines, which are much faster, more efficient, and safer than anyone else’s. Their Made in the USA manufacturing now serves 1000+ global customers, including Caterpillar, Cummins, and MTU (Rolls-Royce).

Rottler’s innovative CNC machines enable precision solutions on engine blocks, working around the engine block, which saves time, quality, and safety. Their 50K sq foot manufacturing facility in Kent, WA, proudly builds “Made in the USA” machinery for their global customers. With 13% annual growth over the last four years and $40M+ revenues, Rottler’s unique market position attracted the strategic private equity investment in October 2025 by Bochi Investments for continued growth and innovation.

This retained executive search was led by Paul Freed/Managing Partner and Kevin Hartz/Managing Partner.

Learn more about Herd Freed Hartz’s track record in:
Manufacturing industry executive searches
Family Business industry executive searches
Private Equity industry executive searches
CFO leadership searches

Neil Moody – Director of Quality @ Red Dot Corporation

Our Herd Freed Hartz executive search team was honored to partner with Red Dot Corporation on a retained executive search to find their new Director of Quality.

Red Dot Corporation, a 100 percent employee-owned leader in mobile HVAC systems for heavy-duty commercial and military vehicles, is entering a pivotal new phase of growth and operational excellence. Reporting directly to the General Manager of Puyallup & Operational Excellence, the Director of Quality will define what world-class quality looks like for Red Dot and lead the organization toward that vision.

Founded in 1965 by Harcourt “Harky” Runnings in Seattle, Washington, Red Dot began by building rugged heaters for vehicles on the Alaska Highway. From those entrepreneurial roots, the company grew steadily, becoming a trusted supplier of mobile HVAC systems for trucks, buses, construction, and defense vehicles. In 2000, Red Dot became a 100 percent employee-owned company, embedding accountability and ownership into its DNA.

Today, headquartered in Puyallup, Washington, with additional operations across the United States and an established international footprint, Red Dot continues to invest in modernization, digital transformation, and operational excellence to serve a growing global customer base.

Key milestones include:
1965 – Founded as a builder of rugged mobile heating solutions
1980s–1990s – Expanded into full mobile HVAC systems for commercial and defense markets
2000 – Transitioned to 100 percent employee ownership
2006–2015 – Expanded operations and advanced HVAC technology capabilities
2018–present – Investing in continuous improvement, supply chain modernization, and strategic global growth

Red Dot’s leadership team values approachability, humor, and humility. The right leader will bring expertise without ego — someone who takes the work seriously but can laugh easily and build trust quickly. Red Dot is a hands-on, collaborative culture where leaders challenge, support, and inspire each other. Success here means leading by example, communicating openly, and helping every employee-owner deliver their best work.

This retained executive search was led by Scott Rabinowitz/Partner.

Learn more about Herd Freed Hartz’s track record in:
Manufacturing industry executive searches