Leaders Letter Newsletter

Leaders Letter 194 – The 3 Box Challenge Interview Question

Dear leaders, I’m going to let YOU into a secret, there’s an interview question I love asking, it is one of three questions with challenges I ask to find out the best candidate(s).  

This is an in-interview question, not a challenge to set with any pre-warning. 

If There Were Three Boxes In Front Of You – What Would You Do? 

Here is the breakdown: 

You don’t know what is inside of  

  • Box 1 
  • Box 2 
  • Box 3 

Some Guidelines 

  • You have 30 seconds to view the boxes 
  • You can lift the boxes once 
  • You cannot shake them  
  • You cannot open the boxes or see inside of them – they are padlocked 
  • You can walk around the boxes and look under the table 
  • You cannot ask for the exact contents of the boxes – but there are varying amounts of money inside 
  • You have 5 minutes to complete this challenge – remember to set the timer so there is pressure associated 

Phase 1A

I will let you ask 3 questions to qualify the boxes 


I can give you 3 hints:

— Do YOU pick the questions or the hints? 

Phase 1B: Questions Or Hints 

The 3 hints are: 

  1. 1 sentence to explain vaguely what inside box 1 
  2. Offer you to pay a % of what is inside box 2 
  3. Box 3 needs breaking open 

Readers stop here: Question: What is the best option for you? 

Phase 2: Answer Questions Or Pick 

Answer questions with varying answers. 

Note: Almost all questions will be trying to validate what’s inside the boxes and which is best. 

Which do you pick?


Do you want to carry on qualifying? 

Phase 3: Select Step Forward Or Step Back? 

Ask: (1) Step forward and select a box 
(2) Do you want to step back — if step back ask them if they want to ask 1 more question or select 1 box to be removed. 

Phase 4: Offer A Question

If I were to ask you to start again would you change your decisions so far? 

Phase 5: Box Selection

Ask what box you are selecting and why?  

» So, which box did YOU select? 

Here are 6 presets to make this successful for you and the candidates:

  1. Set the money amounts for each box before the challenges 
  2. Vary these amounts at each interview some candidates share online and it could be gamed 
  3. Set the timers to view “the boxes” and the 5 minutes – many will run out of time 
  4. Have a slide with 3 boxes set up or a set of boxes you can pull out and run through the exercise 
  5. Work out if you are going to let the candidate see the other two amounts 
  6. Money could be £, $, €’s or could be notes, a cheque, a mocked-up bank statement, a USB stick etc – be sure to know the contents and the order of least to most 

I know what some of you are thinking, this is either a clever challenge or a stupid challenge and you might be right, it could be clever and stupid at the same time. The but: you need to understand the candidate and without some form of challenge and working session how do you get to know them? 

Why This Challenge? 

  • The challenge is designed to understand the decision-making process and understand first, second and third-order thinking from your candidates. 
  • One of the biggest challenges in interviewing is to understand your candidates’ working style and decision-making while asking questions 
  • No questions all answers are typically a red flag to me – this is where a gambler and a calculated risk taker are decided. This is on you as the interviewer to understand and bring out of the candidate 
  • This is a collaboration challenge – you learn if they are a collaborator or make their decisions on their own, if they select not to collaborate ask questions on why this was the case. Hint many selfish managers and above will make the decision not to collaborate, understand the engineering behind this 
  • Making a decision in a controllable environment is what they will likely have to undertake week in and week out 
  • You will find out a lot about the candidate’s confidence and conviction 
  • Candidates who think outside the box often get into the box 
  • This challenge doesn’t have a right answer per se and often within business you have to make a hard or what seems an impossible or stupid decision fairly quickly 
  • This challenge is a simple challenge designed to:
    • (1) Challenge the candidate’s mind 
    • (2) Understand if the candidate wants to change their mind and how many times they change 
    • (3) See how the candidate makes up their mind and challenges themselves and you
  • You find out if you would want to work with and trust this candidate in the early phases of working together 
  • If the candidate does not ask about the motive or what’s in the other boxes, do they demonstrate a growth mindset? Or have they decided to move on and not look back…

Why did I share this today? Many interview questions are bland and restrictive and they do not effectively test candidates in a working environment and you do not understand your potential colleagues at an operating level quickly enough. This is why I have 3 questions and challenges to test the candidates and the interviewing team to deeply understand each other and the dynamics moving forward. 

This week’s focus action is to review this challenge and see if you could use the 3-box challenge in your mid to senior candidates and whether you find out enough about your candidates in your interview process. 

Have a great week and I’ll land in your inbox again next week,


Danny Denhard

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