Questions - Deepstash

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A few questions related to various aspects of work:

  • Icebreaker: How has this last week been for you?
  • Productivity: Is there anything in your work life that you would like my help with?
  • Team: How is everything going with the people you are working with? Any specific interactions you want to talk about?
  • General: How happy you are in your current profile? What could make it better?
  • Work Relationships: Are you getting the right balance between working alone and working with others?
  • Career: What skills would you like to work on?
  • Manager Relationship: What aspect of your job you would like more help or coaching in?



1:1s (or one-on-ones) are worth every leader's time, help maintain employee relationships, and builds trust.

We need to equip ourselves for common challenges and choose the right questions to ask while ensuring adequate follow up.

Rather than being a clueless boss, it is imperative to become a respected leader, one who has harnessed the energy, resources, and processes to work optimally, with the right information at hand.

The Attitude Of The Leader

Once a leader realizes that there is a lot to be learned and everyone around us has an internal life as rich and conflicted as ours, a mutually benefiting 1:1 can be conducted.

One has to know the right questions to ask, not thinking of oneself as an authority figure, but as a learning partner of one's employees and as a student of their insights.

A Hearty Talk

A one-on-one meeting with an employee should:

  • Encourage disclosure.
  • Be regularly occurring in a private setting.
  • Psychologically safe.

One-on-one meetings open up a Pandora's box of valuable information and benefit everyone. By getting things off their chest and being assured of your support, employees see the leader as trustworthy. And if there is any problem or issue that comes out in the open during the discussion, it can get solved at a faster rate together.

Introduction To The Employees

If employees are not familiar with 1:1 meetings, they might think it is a precursor to layoffs, or think of them as another waste of time.

Make sure the right message goes across the team, ensuring that these sessions are now a regular occurrence, and involve you meeting with everyone one by one, to discuss priorities and problems that don't fit in other meetings.

If there is resistance or your employees are short of time, offer them assistance with their work, or accommodate them to a different time, while underlining the importance of the 1:1 session.

Common Challenges and Procedures

If the employee only wants to talk or badmouth co-workers, the leader needs to steer them back, making them focus on what can be controlled. Look for key points in their venting and check if anything that is mentioned is not unlawful harassment for anyone.

Some other ways to ensure compliance:

  • Have a pre-set agenda.
  • Keep the meeting brief(15 to 20 minutes).
  • Having a written recap or minutes of the meeting from the employee.

Unhappy And Distrusting Employees

Chronically unhappy employees are always at risk of quitting or committing a mistake. The leader needs to work with them and prioritize their growth, compensate them fairly, and optimize their daily work.

If the employee doesn't trust you, start with a clean slate and provide direct assurance that you are going to do your best in addressing any problem. If need be, you can apologize for any past issues.

Follow Up

Many issues cannot be solved in a 20-minute meeting, and it is a good practice to follow up and provide a solution at a later time.

Important points for Follow-up:

  • Do not promise or assure any solution in advance.
  • Retaliate that these meetings are confidential.
  • Take their buy-in on the problems and proposed solutions.
  • Park unanswered questions at a later date, finding the answer and getting back to the employee.
  • A written recap is a great way to summarize the team members' achievements, misses and patterns.

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