How to Run a 1:1 in a Startup

One-on-one's are essential to any team's success. Check out our CEO's tips for 1:1s that work.

January 5, 2022
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How would you describe your job to a five year old?
What season would you be?
What is a weird food you have tried? Would you eat it again?
What is your favorite holiday tradition?
Would you go in the mother-ship with aliens if they landed on Earth tomorrow?
What is your favorite season?
Do prefer working from home or the office?
What is your earliest memory of this job?
What is the best thing you have bought so far this year?
What is the earliest book you remember?
If you had to move to another country, which one would you choose?
You are the best criminal mastermind in the world. What crime would you commit if you knew you would get away with it?
What is your favorite movie genre to watch?
What was the last thing you ate?
What person from history would you add to Mount Rushmore?
What is a weird fact you know?
What is your favorite part of working from home?
Were the Spice Girls a good team?
Imagine you can instantly learn any language. Which would you choose?
If you could live in any state, which state would you pick?
Which fictional team is the best team of all time?
What did you want to be when you grew up?
What do you usually eat for a quick lunch?
What simple food will you never eat?
Show us the weirdest thing you have in the room with you right now.
Would you rather stay at a hotel or an AirBNB?
What is your favorite movie genre to watch?
Are you more productive in the morning or at night?
Who is someone in your community that makes a difference?
Who was your most unique pet?
Choose one famous person from history you want on your team during a zombie apocalypse.
What is a good way to give back to the community?
Which song could you listen to over and over again?
Is Hugh Grant funny?
What is your favorite thing to eat for breakfast?
Would you want to have an imaginary friend today? Did you have one as a child?
What actor or actress would you want to play you in the movie about your life?
What is the best super power?
What is your New Years resolution?
You can only eat one food again for the rest of your life. What is it?
What is the best work holiday?
What is the first gift you remember receiving?
Would you rather join Metallica or Backstreet Boys?
What is the best example of a community you have seen?
What is an easy way to do something nice for someone?
Show us your phone background and tell the story behind why you picked this image.
What was your first job?
Pick any band to play at your funeral.
If you could have an unlimited supply of one thing for the rest of your life, what would you pick?
Which superpower would you give to your arch enemy?
What is the most obscure superpower you would want?
What emoji best describes how you are feeling right now?
If you could live in any country, which country would you pick?
Would you rather live in a city or a town?
What is your favorite holiday?
What is something you accomplished as part of a team?
What is your standard office lunch?
What is your most used phone app?
What is your favorite season?
Have you ever won something as a team?
Imagine you are a professional baseball player. What is your introduction song?
Beach holiday or ski trip?
Have you ever been to a funny comedy show?
Would you rather live at the North Pole or the South Pole?
What is your favorite song to sing?
If you could live in any state, which state would you pick?
Imagine you could teleport anywhere. Where would you go right now?
What is the most unusual job you have heard of?
What was the last thing you ate?
You can visit any fictional time or place. Which would you pick?
What do your family and friends think you do all day?
What movie do you wish you could watch again for the first time?
Show us your most-used emoji.
What was the most unique style or fashion trend you ever embraced?
What movie defined your generation?
You are stranded on a remote desert island. Are you alone or with your worst enemy?
What is your favorite knock-knock joke?
Have you ever told someone Santa is not real?
Do you know how to speak more than one language?
On a scale of 1 – 10, how much of a team player are you?
What is your #1 recommendation in this city?
What is your favorite holiday?
What bucket list item do you most want to check off in the next six months?
What is your favorite mythical creature?
What was the first way you made money?
If you could be great at any Olympic sport, which would it be?
Which song could you listen to over and over again?
When did you start liking/hating mushrooms?
Where is your favorite vacation spot?
Do you take your PTO all at one time, or another way?
Which show do you remember most from your childhood?
Which beverage goes best with pizza?
Would you want to have a personal assistant follow you around everywhere and do what you asked of them?
Have you ever met your idol?
What did you want to be when you grew up?
Would you rather live 100 years in the past or 100 years in the future?
What is your hobby?
When you are alone in the car, what volume is the music at?
Imagine you no longer have to work. How would you spend a Tuesday?
What is your favorite type of sandwich?

I've been at small companies, large companies, public companies, and now a rapidly growing startup. Running a 1:1 is the same in each of those companies. After reading hundreds of articles on "the art of a 1:1" and using 10+ software tools over the years, I've come to learn there are only a few key elements that drive a successful 1:1.


Accountability extends to both sides of the aisle. As a manager, skipping meetings, not being prepared, and showing a lack of attention and focus to your 1:1 is a hard no. Managers should:

  1. Prepare a list of questions for each 1:1 that you can ask and monitor the changes in results week over week.
  2. Ask the questions well in advance so your reports can answer them in advance of your call so you can dig into the core of the content.

For example, great questions can be "how can I help unblock your work," "are there any obstacles you are facing on a weekly basis."

You should ask questions that are critical from a managerial perspective to have your reports operating smoothly, but you should also have a question in there where you ask what your reports want to discuss. As a manager, you might find your employee has excellent ideas about the work environment or business itself that you were missing.

  • Run your 1:1’s weekly
  • Send your questions out in advance of your in-person or zoom meeting
  • Review the answers to the questions before your meeting and have key talking points well prepped
  • This will show your report that you care, look out for their career progression, and want them to succeed
Actionable items
  • Make sure there are takeaways from both the report and the manager
  • Make sure the action items make themselves back into the 1:1 for next week
  • Please note whether the action items were completed or not\
  • Follow up here, accountability is key
What should the content of your 1:1’s include:
  1. Emotional Check-Ins

One of the questions should always be, how do you feel. You can break this down as simply or as complex as needed, but there should always be a 1-10 (how do you feel) one way or another. 

Since covid began, employees who come into the office could feel unnecessary pressure to do so, employees who work from home could be feeling fatigued and or isolated. There could be feelings of dissatisfaction that could be directly related to the job or external factors at home, personal life, etc., that could be affecting your reports work. The key is to be there for the person and make sure they can FEEL COMFORTABLE and perform at their best. 

  1. Career Progression

Some say happiness is progress. If that is the case, it's a manager's job to make sure all employees are put in a position where they can move up in the company if they over-perform. Ian Siegel, CEO of ZipRecruiter, always says you should never promote someone who wants to be in that role or title, you should promote someone who is already doing the job. 

Be attentive to your employees and what they want out of the company. Help them map out a clear plan for their next promotion, so no ambiguity is left on the table. Ambiguity and uncertainty on career path lead to searching for other jobs and potentially churn. If they cannot move up, the easiest way is out in a world where the average turnover is less than two years, the easiest path is out.

Assembly can bring all of your 1:1 functionality into one platform. If you find it difficult to send the 1:1 questions to your reports each week, Assembly can automate sending your 1:1 questions in advance and hold both you, the manager, and your direct report accountable. Please see below for an example of how you can automate the sending of your pre-loaded questions:

On top of the accountability, you can review the answers to the questions before the meeting and come prepared to get right into the heart of what your direct report wants to discuss. When you come to the meeting prepared to help your direct report succeed, your employee will know you care, and you paid attention to their feedback and personal goals.

All of the results will show up in one centralized location, so you don't have to go to ANOTHER TOOL to find what your report has been saying:

To learn more feel free to watch this video on how to set up a 1:1 and automate your routine with Assembly.

Should you have any questions and or want to learn more, feel free to book a demo here.

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