Check-ins are the backbone of agile performance management. A check-in is a one-on-one meeting between a manager and a direct report, that should happen on a weekly or fortnightly basis. From a manager’s point of view, check-ins serve many purposes, like:

  • Planning activities and helping employees prioritize according to OKRs
  • Helping employees achieve better results by identifying and removing roadblocks
  • Helping employees understand and learn what drove poor results and especially great results (What can be replicated and avoided going forward?)
  • Transmiting sensitive information down the organization (like a shift in strategy, a product pivot, or a major personnel change
  • Collecting and bubbling up information through the company (what is working and not working; potential ethical/legal issues; missed opportunities, etc)

To employees, most of these benefits are equally important. But also, they can:

  • Communicate expectations regarding future career moves and opportunities
  • Alert the company of potential roadblocks and challenges
  • Achieve better results by having help on roadblock removals and inter-team coordination
  • Get resources such as budget for areas of need
  • Getting advice and help on how to develop blind spots in accordance to current and future responsibilities and opportunities
  • Gathering structured feedback to improve

One interesting framework to guide the check-in, or one-on-one, is to let it be, predominantly, an employee meeting. According to Ben Horowitz, author of The Hard Thing about Hard Things, “The key to a good one-on-one meeting is the understanding that it is the employee’s meeting rather than the manager’s meeting.”

The check-in architecture

Not all check-ins are alike. Even tough they should happen every week or two, the agendas are different for every meeting. It doesn’t make sense, for example, to have career discussions every week with your direct reports: chances are these expectations won’t change that much in such a short time frame. Conversely, it makes no sense to talk about pressing issues on a monthly basis. Pressing issues should be discussed when they arise. Therefore, we’ve proposed a way to structure check-ins so that they remain productive and useful throughout the year.

In a very simple sense, topics accumulate in certain meetings. So pressing issues are discussed whenever needed. Task priorization and effort should be monitored in every meeting, as should the general level of happiness and well-being of the employee. Bi weekly, the manager should add broader questions to the 1-on-1, such as a discussion about the results the tasks produced (like monitoring KPIs and business metrics), as well as consolidating ongoing feedback that might have been received by the employee in the past weeks. General information gathering should also be done. On a quarterly basis manager and direct report should discuss the bigger picture, especially in faster paced companies: how the employee’s career is progressing, what are next development steps, general coaching guidance, etc. Lastly, bi-annualy, or yearly, a discussion about the allocation of scarce resources can take place, where promotions, bonuses, and raises, are addressed, as you can see on the picture below:

Check-in question bank

In order to help managers structure their check-ins, we’ve compiled a question bank that should uncover the right information from direct reports. They are generally grouped by topic, and can be modified, of course, according to need.


  • Are you happy working here?
  • Are you having the opportunity to do what you do best? Realize your potential?


  • What are your current career priorities and goals that excite you?
  • What have you achieved, learned, and are proud of since we last talked?
  • What challenges would you like to take on in the future?
  • What are your life aspirations?
  • Where do you see yourself in 5 to ten years?


  • How are your KPIs doing?
  • Are you facing any roadblocks to meet your priorities? Hit your goals?
  • Which goals you think you are not going to hit this cycle?
  • Why do you think you won’t hit them? Why? Why? Why? Why? Why? (root-cause analysis)
  • What can I do to help you achieve your goals and improve?
  • Which goals you think you are going to hit this cycle?
  • What did you do right? How can you make this the new standard? Why did you hit this goal? Why? Why? Why? Why? Why? (root-cause analysis)
  • Can you teach your peers on how they can also hit their based on this experience?
  • How can you further improve yourself and deliver better results in the future?


  • What suggestions or feedback do you have for me, your team members, and the organization?
  • Tell me about one opportunity in the past month in which you used one of our core values to make a decision?
  • Do you know our core values?
  • How do you translate our core values into action?
  • Do you think we’re acting in consonance with our core values as a company? Me as a leader?

Information Gathering:

  • If we could improve in any way, how would we do it?
  • What’s the No. 1 problem with our organization? Why?
  • What’s not fun about working here?
  • Who is really kicking ass in the company? Who do you admire?
  • If you were me, what changes would you make?
  • What don’t you like about the product?
  • What’s the biggest opportunity that we’re missing out on?
  • What are we not doing that we should be doing?


  • What drives you most? Cash? Equity? Experiences? How would you prefer to be compensated?
  • Are you happy with your current compensation? Why? Why? Why? Why? Why? (root-cause analysis)

General guidelines

Have the employee register the main takeaways of the check-ins in some system like Qulture.Rocks or Google Sheets. It will build up a very rich history of the employee’s performance and life within the company, for future consultation. Having the employee specifically register the takeaways serves the important purpose of empowering her to take ownership of her development and performance, as opposed to “acting like a whiny baby”

Set out the agenda upfront. Let the employee know what’s the goal of the meeting, and ask in advance if he has pressing issues to be discussed. This will both force her to prepare for meaningful discussions, and also to think through whatever should be bubbled up

Let the employee speak. Many managers make the mistake of overwhelming their reports with so much information. Check-ins should generally be a servant leader’s opportunity to hear and help, and not to talk and preach

Don’t force the meeting to go on for a specific amount of time, like an hour, if there’s nothing to be discussed. Alternatively, don’t let it extend beyond the allotted time, which should generally not exceed an hour. Managers can reserve certain halves of certain days for their religious one-on-ones, which can’t be canceled

If you’re a CEO, you should NEVER, EVER, skip one-on-ones, or be sloppy about them. The sloppiness will spread like wildfire down the organization, and in no time everybody will be skipping theirs. You should ALWAYS set the tone, which dovetails nicely into the next point

The CEO, and only the CEO, should train management on conducting their 1-on-1s. By running his great 1-on-1s with his direct reports, the CEO will logically be a step ahead in disseminating the right practices down the company, but it isn’t enough: the CEO should personally explain the hows and whys of perfecting 1-on-1s to each and every manager in the organization, so the idea really gets spread and calcified in people’s minds. The CEO, and this should go unsaid, can’t outsource management - his main responsibility - to HR

Build a good company

In his “A Good Place to Work”, Ben Horowitz discussed the importance of one-on-ones, by telling the tale of one day when he discovered one of his managers had left six months go by without having check-ins with his direct reports. He concludes that he had failed to persuade his VP by telling the what, but not the why. In the end, he threatens to fire the VP if he doesn’t get his check-ins done fast, and here’s why:

“was it really necessary for me to make such a dramatic speech and threaten one of my executives?

I think it was for the following three reasons:

  • Being a good company doesn’t matter when things go well, but it can be the difference between life and death when things go wrong.
  • Things always go wrong.
  • Being a good company is itself an end.

When things go well, the reasons to stay at company are many:

  • Your career path is wide open because as the company grows lots of interesting jobs naturally open up.
  • Your friends and family think you are a genius for choosing to work at the “it” company before anyone else knew it was “it”.
  • Your resume gets stronger by working at a blue chip company in its heyday.
  • Oh, and, you are getting rich.

When things go poorly, all those reasons become reasons to leave. In fact, the only thing that keeps an employee at a company when things go horribly wrong—other than needing a job, which isn’t so applicable in the current macro environment—is that she likes her job.

There has never been a company in the history of the world that had a monotonically increasing stock price. In bad companies, when the economics disappear, so do the employees. In technology companies, when the employees disappear, the spiral begins: the company declines in value, the best employees leave, the company declines in value, the best employees leave. Spirals are extremely difficult to reverse.[ˆfoo1]”


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