Hiring Beyond the Checklist: Getting the Right Executive for the Job

Extraordinary Pursuits by BIP Ventures

What separates a “good on paper” executive from a truly transformational leader? In this episode of Extraordinary Pursuits, host Rachelle Kuramoto sits down with Kristian Schwartz, founder of Montgomery Group Executive Search, to dig into the art and science of hiring leaders who can move a business forward, especially when the stakes are high.

Executive hiring isn’t about ticking boxes or filling roles with the most impressive names and resumes. Kristian explains why it’s about clarifying the real business need, finding alignment on mission and culture, and having the conviction to recommend the candidate, even if they aren’t the one who looks “perfect on paper.” Whether you’re a founder building your first leadership team or an executive seeking to scale without making costly hiring mistakes, this is an episode that will help you think differently about talent, risk, and fit.

‍It’s not about finding the ‘perfect’ candidate. It’s about identifying the right one for the right reasons.

Key Takeaways:

• Why 40–70% of executive hires fail, and how to avoid the common traps of misalignment and poor onboarding

• How to clarify the true business problem a new leader is meant to solve before you even start the search

• The importance of transparency around candidate risk profiles (and why some risk is good)

• How to use both data and intuition to make a confident, high-stakes hiring recommendation

• Strategies for validating role specs with real candidates and making final selection decisions that last

Points of Wisdom:

• “Making the recommendation requires a lot of conviction, and when it sticks, it’s incredible.” [09:27]

• “40–70% of executive hires fail in the first 18 months because of poor role definition, misalignment, and onboarding gaps.” [12:49]

• “Have a very clear role specification based on what the first-order problem is.” [16:54]

• “De-risking and being transparent with risk is key because different people have different appetites for risk; understand where a person is and what their comfort with risk is.” [20:22]

Timestamps:

[00:01] – Introduction: Rethinking Executive Hiring

[03:47] – Kristian’s Background and Entrepreneurial Journey

[08:24] – Conviction in Hiring: Finding the Unicorn

[09:55] – The Art (and Reward) of Executive Search

[11:34] – Strategic vs. Tactical: Getting Clear on What Matters

[14:29] – Why “Slowing Down” Can Accelerate Better Hires

[16:45] – Filtering Candidates for Fit, Not Just Skills

[20:22] – De-Risking the Process: Understanding Appetite for Risk

[22:54] – Validating Role Specifications with Real Candidates

[26:12] – The Science (and Art) of Final Selection

[32:08] – Balancing Technical Skills with Culture and Support

[34:47] – Humanizing the Process: The Role of AI

[37:11] – Where to Connect with Kristian

About Kristian Schwartz:

Kristian Schwartz is the founder and partner at Montgomery Group Executive Search, specializing in recruiting functional leaders for digital marketing, transformation, and strategy. With a background as an entrepreneur and seasoned recruiter, Kristian helps high-growth companies find leaders who fit the context, not just the job description.

LinkedIn | Montgomery Group

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