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Most hiring failures do not start in the interview.

They start much earlier, when the role is poorly defined, success is unclear, candidates are not given the right context, and managers inherit a process that was never built to set anyone up to succeed.

In this episode, I sit down with Ashley Herd, former employment lawyer, HR executive at McKinsey and Yum Brands, and author of The Manager Method, to break down where hiring really goes wrong and what leaders need to fix before they open their next search.

We get into why most job descriptions fail to define success, how bad hiring decisions are often design failures rather than selection failures, and why the candidate experience so often promises one environment while the job delivers another. Ashley also shares her “tight jeans vs oversized sweatpants” framework for management, and we unpack what structured autonomy actually looks like in practice.

We also go deep on onboarding, executive failure, the role HR should play versus the role it often gets left with, and the question more leaders need to ask now: should this role even exist in the form we are hiring for?

If you hire, lead, or build teams, this conversation will change how you think about role design, interviewing, onboarding, and management.  

In this episode, Ashley Herd joins me to unpack why so many hiring decisions go wrong long before a candidate enters the process.

We explore the real root of hiring failure: poorly defined roles, vague success criteria, copy-paste job descriptions, and interview processes that generate very little signal. Ashley explains why most organisations are still hiring for tasks and years of experience instead of outcomes, future context, and the behaviours that actually drive success.    

We also get into one of the most useful frameworks from the conversation: tight jeans vs oversized sweatpants management. Tight jeans managers over-control. Oversized sweatpants managers create ambiguity. The goal is somewhere in the middle: structured autonomy.  

We cover:

• Why most hiring failures are really role-design failures
• What job descriptions miss when they describe activity instead of success
• Why unstructured interviews produce weak hiring decisions
• How candidates are often sold one environment and dropped into another
• Why hiring should be treated as the first phase of onboarding
• Why executive hires fail faster and more often than most leaders realise
• How to think about AI when redefining roles and headcount
• Why hiring works best as a partnership between HR and the business

Key ideas from the episode

• Most jobs are defined too loosely to hire well against
• Success should be defined at 90 days, 6 months, and beyond
• The interview process should reflect the real working environment
• Managers need guidance, not just responsibility
• If you do not define the role properly up front, the failure cascades later

Follow Ashley Herd: https://www.linkedin.com/in/ashleyherd

Get The Manager Method: https://www.managermethod.com/book

Follow Konstanty Sliwowski on LinkedIn https://www.linkedin.com/in/sliwowskik/

For more insights check out www.schoolofhiring.com and newsletter.schoolofhiring.com