Most hiring mistakes aren’t obvious on day one. 

The CV looks great. They interviewed well. The references check out. The first few weeks feel fine. 

Then, slowly, you feel it: execution slips, standards wobble, and your leadership team starts spending time on issues you didn’t expect to be managing. 

If you’re hiring an executive, this is one of the highest-leverage questions you can ask: 

Based on what the business needs right now (results, strategy, urgency etc) have we made the right hire? And will we act immediately if we haven’t?  

A wrong hire isn’t just a people problem. It’s also a strategy execution problem. It shows up as missed priorities, slow decisions, and distracted leaders. 

Here’s how to get it right… 

 

Step 1: Start with the outcomes (not the person in your head) 

Recruitment specialist Nancy Slessenger (guest on The Inner Chief podcast), warns that many leaders unconsciously hire to a mental picture: a certain age, background, industry, or ‘type’. 

It’s not only unreliable - it can be damaging. 

Instead, start with a CEO-level brief: 

  • What must this role deliver in the next 90 days? 

  • What must it deliver in the next 12 months? 

  • What does “good” look like in observable behaviours? 

  • What values are non-negotiable here (and how would you see them in action?) 

Then get brutally specific about skills. 

“Good communication” isn’t a skill. It’s a label. 

A testable skill sounds more like: “When presenting to the board, they can explain complex ideas clearly enough that decisions get made quickly.” 

When you define skills in real situations, you can actually assess them. 

 

Step 2: Use the skills + character filter (and don’t negotiate with yourself) 

At Chief Maker, we subscribe to the Jim Collins principle: “Get the right people on the bus, and the wrong people off the bus”. 

A simple filter helps when assessing a hire (new or tenured):  

  • Skills: do they have the technical, tactical and social skills required to do the job? 

  • Character: do they bring the attitude, values, and emotional maturity your culture needs? 

But here’s what many leaders miss… 

It’s not a one-time decision. The context changes. The business changes. 

So keep asking… Do we, without a shred of doubt, have the team that can achieve the mission and goals? 

If the answer isn’t a confident yes, don’t ignore the nagging feeling. Don’t negotiate with yourself that it’ll work out eventually.  

Action is required (and fast) because every day you delay is a risk to strategy, culture and goals. 

 

Step 3: Make sure the seat is real (and at the right level) 

Sometimes the hire isn’t wrong - the seat is. 

Zaklina Craig (Business NSW and guest on The Inner Chief podcast) points out that many organisations don't design roles at the right level of leadership and complexity.   

Senior executive roles require systems thinking across multiple functions or jurisdictions, with a longer time horizon (often 3-5 years). Middle management roles tend to focus on more local systems, with a shorter horizon (often 1-3 years).  

A useful rule of thumb… roughly 70% of the role should be work at its true level of complexity.  

Get the complexity right and people will feel challenged, capable, and energised.  

Get it wrong and the result is predictable… 

  • The work is too simple (they disengage) 

  • The work is too complex (they struggle) 

  • The role is spread across too many priorities (nothing gets done well) 

Before you decide they’re not the one, ask yourself: 

Have we clearly articulated the level of leadership required? And do we really know what work they should be doing 70% of the time? 

 

Step 4: Run probation like a performance window (not a courtesy period) 

Even when you do everything right, sometimes it’s still the wrong fit - especially culturally.  

Carolyn Creswell (Carman’s Kitchen and guest on The Inner Chief) is direct about why probation exists: to make a clear call while you still can. 

In Australia, you typically have six months. Use it carefully. 

Her test is simple: At six months, would you enthusiastically rehire this person? 

If the answer is no, the cost of delay is huge. 

After probation, you’re often in performance management territory - draining managers, distracting leaders, and consuming energy that should be going into execution. 

 

Step 5: Don’t confuse “good person” with “right person for this chapter” 

Another hard truth: someone can be great, but not right for the next chapter. 

They may have been a perfect fit when the business was smaller. Then the business grows, complexity changes, and the role requires a different skill set. 

In many roles you can teach skills - but you can’t change who someone is innately.  

That’s why leaders need the courage to tell the truth early - and act with clarity. 

 

The CEO job: right people, right seats, decisive timing 

If you’re the CEO or Business Unit Head, you can’t outsource this responsibility. 

Your job is to: 

  • Put the right people on the bus 

  • Make sure they’re in the right seats 

  • And when it’s time for someone to hop off, have the courage to release them so they can find a new role they’ll be much happier in  

Because the cost of a wrong hire isn’t just salary. 

It’s momentum, culture, and the attention of your best leaders.