How and Why to Conduct a One-on-One Check-in Conversation with Staff or Family Members

A one-on-one conversation might be the most powerful tool you have to alter the trajectory of a person’s life or their relationship with you. Here’s how and why to do it.

Below I’ve collected notes from:

  • Ashley Goodall & Marcus Buckingham in NINE LIES ABOUT WORK: A Freethinking Leader’s Guide to the Real World
  • Andy Grove in High Output Management
  • Ben Horowitz in The Hard Thing About Hard Things
  • Tim Ferriss

Nine Lies About Work – Ashley Goodall & Marcus Buckingham

How often should team leaders meet with team members? Marcus Buckingham and Ashley Goodall, in the book Nine Lies About Work, insist that once per week is the right frequency for one-on-one meetings between Team Leaders and Team Members. These conversations should ask two simple questions:

  1. What are your priorities this week?
  2. How can I help?

The weekly check-in can be as short as 10-15 minutes if it specifically tackles a particular situation the team member is facing. The authors make the bold claim that the check-in is not only the most important part of leading, it IS the work of leading. Read more about this approach on Susan Cain’s Quiet Revolution blog.

High Output Management – by former Chairman and CEO of Intel, Andy Grove

The one-on-one meeting was a cornerstone of Intel’s highly regarded management philosophy. From the legendary business book, High Output Management by Intel’s employee #3, Andy Grove:

  • One of the fundamental tenets of Intel’s managerial philosophy is the one-on-one meeting between a supervisor and a subordinate. Its main purposes are mutual education and the exchange of information. By talking about specific problems and situations, the supervisor teaches the subordinate his skills and know-how, and suggests ways to approach things. At the same time, the subordinate provides the supervisor with detailed information about what he is doing and what he is concerned about. Obviously, one-on-ones take time, both in preparing for them and in actually holding them—time that today’s busier manager may not have.
  • I feel that a one-on-one should last an hour at a minimum. Anything less, in my experience, tends to make the subordinate confine himself to simple things that can be handled quickly.
  • What is the role of the supervisor in a one-on-one? He should facilitate the subordinate’s expression of what’s going on and what’s bothering him. The supervisor is there to learn and to coach.
  • “Ask one more question!” When the supervisor thinks the subordinate has said all he wants to about a subject, he should ask another question.
  • Both the supervisor and subordinate should have a copy of the outline and both should take notes on it, which serves a number of purposes. I take notes in just about all circumstances, and most often end up never looking at them again. I do it to keep my mind from drifting and also to help me digest the information I hear and see. Since I take notes in outline form, I am forced to categorize the information logically, which helps me to absorb it. Equally important is what “writing it down” symbolizes. Many issues in a one-on-one lead to action required on the part of the subordinate. When he takes a note immediately following the supervisor’s suggestion, the act implies a commitment, like a handshake, that something will be done. The supervisor, also having taken notes, can then follow up at the next one-on-one.

The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz

Student of Andy Grove, Ben Horowitz’s books are a next-gen continuation of High Output Management. Aside from being the best at incorporating hip hop lyrics into business literature, Ben is cofounder of Andreessen Horowitz and one of Silicon Valley’s most respected and experienced entrepreneurs. Ben continues to beat the drum of one-on-one meetings as good management practice in The Hard Thing About Hard Things:

  • While it is quite possible to design a great communication architecture without one-on-one meetings, in most cases one-on-ones provide an excellent mechanism for information and ideas to flow up the organization and should be part of your design.
  • A good practice is to have the employee send you the agenda in advance. This will give her a chance cancel the meeting if nothing is pressing. It also makes it clear that it is her meeting and will take as much or as little time as she needs.
  • If you are an employee, how do you get feedback from your manager on an exciting but only 20 percent formed idea that you’re not sure is relevant, without sounding like a fool? How do you point out that a colleague you do not know how to work with is blocking your progress without throwing her under the bus? How do you get help when you love your job but your personal life is melting down? Through a status report? On email? Yammer? Asana? Really? For these and other important areas of discussion, one-on-ones can be essential.
  • Questions to surface quality information and signals:
    • If we could improve in any way, how would we do it?
    • What’s the number-one problem in our organization? Why?
    • What’s not fun about working here?
    • Who is really kicking ass in the company? Whom 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 we are missing out on?
    • What are we not doing that we should be doing?
    • Are you happy working here?

Bonus: One-on-One Check-Ins with Family Members

This practice isn’t just important for work relationships, it is equally powerful for connecting with family and friends in an impactful way. Many of these approaches are easily translated to personal relationships.

Andy Grove has this to say about it in High Output Management:

  • To digress a bit, I also think that one-on-ones at home can help family life. As the father of two teenage daughters, I have found that the conversation in such a time together is very different in tone and kind from what we say to each other in other circumstances. The one-on-one makes each of us take the other seriously and allows subtle and complicated matters to come up for discussion. Obviously, no notes are taken, as father and daughter usually go out for dinner at a restaurant, but a family one-on-one very much resembles a business one-on-one. I strongly recommend both practices.

Similarly, Tim Ferriss has suggested a weekly meeting with your significant other (complete with meeting minutes!?!) as a tool to keep your relationship on the rails. He recommends this powerful question as a “soft” way to tease out issues with the goal of avoiding an offense that shuts down the conversation:

  • What would you like to see more of?” Or, if you are feeling brave, “What would you like to see more of FROM ME?”

Consider some of the sample questions mentioned in this post, but reframed for a family member check-in. I’ve found these ones helpful in my family discussions:

  • What’s not fun about being in this family?
  • If you were me, what changes would you make?
  • If you could change only one thing about your life right now, what would you choose?
  • What were the three best parts of last week?
  • What are three things you would like to see happen in the coming week?

Please let me know what has worked for you by commenting below or shooting me an email.

2 thoughts on “How and Why to Conduct a One-on-One Check-in Conversation with Staff or Family Members

  1. This is a really great post Jeff. Important to understand communication between coworkers and also family as it is so easy to create small misalignment between people week after week. Also, love the servient leadership woven in to this as well as a big part of leadership is facilitation and creating an environment for everyone to do their best.


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