Three tips for successful one-on-one meetings

“Ugh, what are we even going to talk about?”

How many times have you looked at your calendar, realized that you have a one-on-one meeting with someone on your team, and fallen into a spiral of anxiety about how you will fill the time? Maybe you end up talking about their current project’s status, or you grab a couple of questions from that “101 questions to ask in a one-on-one” list and ask those, or, almost the worst of all, you just chat about life and industry news for 45 minutes.

This has happened to me. I remember getting caught up in the day-to-day of project work and then looking at the calendar and realizing that I have several one-on-ones coming up and that we never set up an agenda. I made a mistake.

Not setting up an agenda was not the mistake that I made, though.

The mistake that I made was not pushing on my direct reports to own their one-on-ones.

As a manager, you own the team’s outcomes and you own its morale, psychological safety, and your team members’ opportunities for growth, but you don’t own their careers. Each individual owns their own career, and it’s up to them to articulate what they’re looking to achieve, the challenges they face, and how you can help them.

A single one-on-one meeting is not a success in isolation; successful one-on-ones advance a dialogue. The outcome of the one-on-one process is rapport, relationship, and a shared ideal for the future around which is built a concrete execution plan. If a one-on-one meeting is not materially advancing that planning activity, take a few minutes to think about why that is.

Here are my top “do"s and “don’t"s for successful one-on-ones that should help you begin to make real progress.

#1 Never Skip!

“Use it or lose it,” as they say in the fitness world. Neglected muscles shrink, while exercised muscles grow. If you wish for your one-on-ones to produce real change and success for your team members, you need to have them consistently.

As a manager, your behavior acts as a model or template. If you repeatedly trample others’ calendars, reschedule planned events, or cancel meetings, not only are you teaching your direct reports that it is OK to do that, you’re also silently asserting what you think is important to spend time on, and if that is not one-on-one conversations with those people, they are going to come to the conclusion that their success is not important to you.

Don’t let that happen; always keep your one-on-one obligations.

There are always those edge cases when things need to get moved around or even canceled, but when you’re considering making that change, think about the message it sends.

#2 Don’t take on the planning burden!

Your job as a manager is to set expectations for your team, which you do through a combination of interpreting the company’s stated business goals and its expressed standards for performance (which varies by company size) and by making your own observations.

That said, it is the individual’s job to have ambitions, which means that it is their job to set the topics of discussion for one-on-ones, to understand where they need help, and to ask for it. That having been said, there is a lot you can do as a manager to support your direct reports as they get comfortable doing all of that.

Mountains of words have been written on this topic, but this one of the key areas where coaching is an effective tool. You can use powerful questions to guide your people into lines of thinking that uncover their true desires and fears, and then push them to commit to meaningful change over time.

I will explore this topic in depth in future articles, so consider subscribing so you don’t miss them, but suffice it to say there is a lot of latitude here for you to develop your personal style, and a lot of opportunity to create in people a strong sense of ownership over their own futures.

#3 Keep a record!

Famed management consultant Peter Drucker is oft quoted, “If you can’t measure it, you can’t improve it.” That has become a cliche and an excuse for some managers to avoid using their heads, but the basic notion is sound.

Create a shared doc with each team member to track what your one-on-one conversations cover. Record what you discuss, what the next steps should be, and what the outcomes are. This can be done in a multitude of ways, and there are even several products on the market that attempt to automate it including 15Five and Lighthouse.

A simple Google Doc or Dropbox Paper record should be sufficient, provided that you both can view and edit it.

This document can become the centerpiece for collaboration and conversation. Expect your team members to groom the document on a weekly basis, adding the things they want to dig into or get advice or coaching on. If topics are not getting added, that’s a symptom, and might be a topic itself.

Having this document at hand makes retrospective conversations, performance reviews, and other role planning activities easier.

These are the essential three tips that I would offer any manager in any industry. Clearly there is a lot more to say, and I will go further in depth in future articles. Please subscribe so that you never miss a thing!

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