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47 QUESTIONS TO ASK
IN ONE ON ONES
By Jon Birdsong
CEO, Rivalry

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“The wise man doesn't give the right
answers, he poses the right questions.”
-Claude Levi-Strauss
“To raise new questions, new possibilities, to
regard old problems from a new angle,
requires creative imagination and marks
real advance in science.”
- Albert Einstein

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“The art and science of asking questions is
the source of all knowledge.”
-Thomas Berger
“Successful people ask better questions, and
as a result, they get better answers.”
- Tony Robbins

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Every smart manager knows the key to getting more out of your team is to help them uncover answers
to their questions.
Asking the right questions is the best way to uncover answers…and even more questions! You want to
be a great manager and leader of individuals — that is why you downloaded this book.
It first starts with building great relationships with each of your direct reports. Weekly One on Ones are
the best way to systematically build great, professional relationships.
Often times, One on Ones are stale. It’s either rushed, missed, or mislead. The perfect structure of a
One on One creates a formula of deep interest, great questions, and the intent of listening.
The following 47 questions have been hand selected by me after talking with thousands of managers.
What do they look to uncover? How do they lead? Which questions are the most meaningful? How do
you build the best relationship with your Direct Reports?
These were all questions I wanted to understand. This book is the start.
Sincerely,
Jon Birdsong
CEO , Rivalry

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Set the Agenda
The Weekly One on One is for the Direct Report. It is not
for the manager. It is a 30 minute meeting structured
around a set agenda. The best managers open the first 10
minutes to the Direct Report for whatever they would like
to discuss. Remember, a weekly One on One is to build a
great relationship. The better your relationship with your
direct reports, the better the results. This requires amazing
listening skills and immense patience. The following
questions will guide you.

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Set the Agenda Questions
• Set the agenda for our next One on One.
• What are the MUST REVIEWS for our next
One on One?
• Grade the week.
• How are you?

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Reinforce Good Behavior
Weekly One on Ones should be your Direct Report’s
favorite 30 minutes of the week. Highlighting good
behavior is critical to making this 30 minutes postive and
productive. Too many managers want to dive into what’s
not working. Direct Reports can quickly lose confidence
and get into a rut. Open up the communication channel to
what is really going well. Let them brag about themselves.
You will know what get’s them going and motivated.

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Reinforce Good Behavior Questions
• What went well this past week?
• What was the best meeting you had this week? Why?
• What was the best conversation you had this week? Why?
• What was the best personal development moment this week? Why?
• What is your strongest skill that sets you apart from anyone else in the company?
• Any new leads worth mentioning since our last one on one?
• What did you do last week to develop yourself?
• Name one thing you’ve accomplished since the last meeting that you’ve been proud of?
• Name a person who has helped you since the last meeting.
• Mention one thing you’re looking forward to in the coming week/month?
• Mention something interesting you’ve learned since the last meeting.

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Address Challenges/Areas of Opportunities
Weekly One on Ones revolve around a professional
relationship. It is more than just a time to shoot the breeze.
Your professional relationship with your Direct Reports
generates a level of expectations and commitments.
Challenging the Direct Report on Areas of Opportunities is
one of the most important jobs functions of a great leader.
Many managers get passive and lazy when focusing on
the difficult areas. Use the following questions maintain
exposure on areas of improvement.

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Address Challenges/Areas of Opportunities
• What went poorly this past week?
• If you could have a conversation to do over, which one would it be? Why?
• What was the worst meeting you had this week? Why?
• What is the biggest objection you faced this week?
• Is there anything keeping you from getting your work done?
• What are the biggest time wasters for you each week?
• What’s the biggest opportunity that we’re missing out on?
• Where are we least efficient?
• What’s one thing we’d be crazy not to do next quarter to improve our product?
• What are we not doing that we should be doing?

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Game Plan
Your weekly One on One is the opportunity to strategize
and game plan for the week ahead. This 30 minutes with
you could change the outcome of the 39.5 hours (at least)
they execute throughout the week. Now is the time to
focus and deploy strategic initiatives to your Direct
Reports.

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Address Challenges/Areas of Opportunities
• What are your priorities for the next week?
• Which 3 opportunities are closest to closing? Why those 3?
• What one skill do you want to get better at this week?
• What can we do now to promote long-term success?
• What is the one thing you want to learn this week (process,
customers, competition, etc)?
• What suggestions do you have?
• If you could do better than the week before, what would it take?

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Relationship Building
Knowing some of the quirks and unique traits of your
team members is a great strategy for building
relationships. It’s the different between an entertaining
and engaging conversation at lunch or a boring one. Some
of the best rapport is developed by forming bonds over
the most unique and random commonalities. As a
manager, find them out with the help from the following
questions.

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Relationship Building
• What would make you happiest on a work day?
• How do you celebrate your birthday?
• Where would you travel if you had one month off?
• You can only use one social network for the rest of your life! What is it?
• Who’s your dream celebrity interview?
• What is your biggest pet peeve?
• What did you want to be when you were younger?
• Pick a drinking buddy.
• Pick your next home.
• What’s the name of your Memoir?
• Best thing you have read lately?
• When was the last time you felt really challenged at work?
• Is there anything you need in order to perform your job better?
• What parts of the business would you like to be more involved in or learn about?
• What’s the most fun you’ve had while working here?
• What was the best part of working for our company this week? Why?

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