Enjoy The Work blog post. One on one.

So many of us fear it. We try and strike it from our minds. We look for reasons to delay or even cancel. But then, once again it’s upon us. The dreaded one-on-one.

We know the routine. It starts with an awkward hello where the employee asks whether s/he should close the door behind them (a harbinger for whether the grim reaper might attend as well). You fumble through niceties about whether the weather might turn or if the local sports ball team might make the playoffs. Another moment of silence passes before one of you shifts the discussion toward professional topics.

What follows is predictable. The supervisor inquires about the state of various projects. The employee dutifully answers. Both parties silently count the minutes until the torture can end.

How many of you out there believe your one-on-one skills could improve? Mediocre one-on-ones display consistent symptoms. Hit the “Clap” button for this article for each “Yes” response to the following questions.

  1. There is no agenda distributed in advance of the one-on-one (1 clap)

  2. There is no articulation of the company’s biggest priorities and how they relate to the employee (2 claps)

  3. The supervisor spends more time talking than listening (5 claps)

  4. There is no time spent on the employee’s career path or personal development (5 claps)

  5. One or both participants are distracted by phones or computers (7 claps)

  6. When the employee shares that a project is delayed, the supervisor responds with (unsolicited) solutions rather than questions (10 claps)

  7. Notes and action items are not captured by either attendee (20 claps)*

If your total = 50 claps, thank you for increasing the post’s popularity, and shame on you. 🙂

Sound familiar? We’ve all participated in this clumsy dance. Without the active effort to improve the situation, the inevitable conclusions are the meetings first decrease in frequency before vanishing completely.

But I have good news. The single most powerful communication tool in a company’s management arsenal is still the one-on-one, and it takes shockingly little effort to shift them from drudgery to usefulness.

All it takes is P.E.A.C.E. = Presence, Empathy, Agenda, Check-In, and Exchange.


Get rid of your phone. Close your email, Slack, instant messaging, Skype or any other communication vehicles that might steal your attention. Practice active listening. Being fully in the room with your employee is the critical, untouchable, non-negotiable first ingredient to a successful one-on-one. We’re all moving so fast. A workday can be a blur. Make the one-on-one the calm eye in the middle of the storm.

Action: center yourself, even if just for a few minutes before the start of the one-on-one. Wrap up the task in front of you, take a couple of deep breaths, and remind yourself that the intention for the upcoming meeting is to serve the employee, not just yourself.


Prior to the meeting, ask yourself, how might my employee be feeling? What do I know is happening in the company or in their life that might be impacting them? Step into their very trendy shoes, even if just for a moment.

Action: zoom out and then zoom in. Consider the company as a whole, what is shifting, what is important, and what might be scary (or exciting) to the employee with whom you’re about to meet.


Good meetings have structure. Ask yourself the question, “What are the goals of TODAY’S one-on-one?” Answering this question will shift the routine and mindless into the unique and intentional. Every meeting has a goal, and the agenda (preferably distributed in advance) is what increases the likelihood of achieving that goal.

Action: Use a running shared document. Each week capture key updates and record action items. This will ensure a living memory of your one-on-ones. The benefits of this practice will be many ranging from informing your next agenda to future performance reviews.


At the outset of the meeting, start with some actual human connection. Remind each other that you are not simply fleshy robots meant to serve. See how you both are doing. Is one of you tired? Or caring for a sick family member? Anticipating a long vacation? Our energy is the context for our content (s/o Tony Robbins), so knowing how we each are feeling will add color to the discussion to follow.

Action: Make sure to ask real questions about worthy topics. Connection comes from relating to the person in front of you by discussing parts of life about which your employee cares. For me, that’s my wife, dog, friends, family and company (though the order of importance fluctuates regularly).


Time to share! The supervisor should start. Share big company news, strategic topics, or anything that might impact the department or the employee directly. Take special care to connect the big picture with the employee’s specific areas of responsibility. Next, it’s the employee’s turn. Follow the agenda and tick off the list of current projects and key metrics to indicate where targets are in danger, or help is needed. When done, both participants should wrap the meeting with action items.

Action: Leverage pre-existing documents to educate the employee on big company news. Leverage CEO letters (somewhat redacted) board decks, leadership OKRs, etc.

One-on-ones can be torture or joyous. They can be a place for healthy debate or one-sided dictation. When done correctly, both parties look forward to them and every topic from career advice to company strategy to personal tragedy is safe to discuss.

Many think of companies as machines where people are just one of the inputs required to deliver widgets to customers. But people are not machines, and real connection is often what gets the best out of us. That connection starts one-on-one. May P.E.A.C.E. be with you.

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