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A leader's guide to one-on-one meetings [+3 templates]
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A leader's guide to one-on-one meetings [+3 templates]

One-on-one meetings may be common, but without some care, they’re not always effective.

October 22, 2020
Rob Lennon
Customer Education Lead at Hugo
Marketer and author with experience spanning a diverse 16 years in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

What makes for a good one-on-one meeting?

For some leaders, all it takes is a friction-free session of friendly conversation. For others, it’s about keeping tabs on team members to ensure they remain on track.

Neither approach is innately bad, but they’re not especially compelling on their own either.

Despite their popularity, one-on-one meetings are an often mishandled part of doing business.

To improve the quality of your one-on-one meetings, this guide outlines considerations for three of the most common types, also offering advice around how not to handle them.

Common one-on-one meeting mistakes

Some of the most talented leaders get one-on-one meetings all wrong.

Whether it’s because they have too much on their plates or they’re not sure how to provide value to direct reports, this usually results in lackluster meetings that don’t offer much for either party.

In worst-case scenarios, these one-on-one meetings may even prove more harmful than helpful.

Here are some of the most common one-on-one meeting mistakes to avoid.

Treating one-on-ones them like a freeform jam session

One-on-one meetings don’t necessarily need to follow a strict agenda, but expecting to wing it without any goals in mind will make them significantly less effective.

You can’t just show up and expect team members to do all the heavy lifting. It’s also unrealistic to expect the conversation to flow naturally. If both parties show up unprepared, it’s almost a given that awkward and unproductive conversations will ensue.

Dodging or avoiding uncomfortable topics

Did the company recently lay off an entire team on a Friday? Has there been extra pressure on your team to meet end-of-quarter quotas?

You’ll want to use one-on-one meetings to address any recent changes or challenges head-on rather than pretend they don’t exist—or worse, come across indifferent. You can never be sure how members of your team are dealing with certain developments, but you can create the room to discuss them.

Rescheduling or showing up late often

Your team gets it—you’re busy. But when you frequently deprioritize one-on-ones with direct reports, it sends them the unintended message that they’re not a top priority.

It’s also a good sign that your time management skills could use an upgrade. If you’re running from one meeting to the next more often than not, for instance, build a buffer between meetings to give yourself enough time to recover.

Treating them as an opportunity to grab a coffee

There’s nothing wrong with moving meetings outside of the office. A change of scenery can be a refreshing alternative to the familiarity of your favorite conference room.

But scenery can’t make up for substance. You still need to have something meaningful to talk about. When a leader routinely turns one-on-ones into an opportunity to grab lunch or get a coffee, it suggests they don’t take these meetings seriously and view them as a chance to take a break from their “real work.”

Focusing your energy on your laptop or things on your screen

Whether you’re in the office or on a video call, focusing too much on your laptop or other technology sets the stage for impersonal one-on-ones.

This may be unavoidable when reviewing a project-in-process, but more often, it indicates that the manager is either preoccupied with other things or uncomfortable with being present.

In either case, failing to engage with the person across the table (or screen) creates distance between a manager and their direct reports.

Becoming defensive or dismissive when challenged

Having and showing empathy is essential to mutually fulfilling one-on-ones.

The psychological safety needed for people to speak up erodes in seconds when managers become flippant or dismissive when receiving feedback.

If there’s one thing employees should feel comfortable doing during a one-on-one meeting, it’s asking questions or raising concerns. Make sure to maintain an open mind and even temperament, even when feedback catches you off-guard.


How to make one-on-one meetings worthwhile

For leaders, an effective one-on-one meeting serves three purposes:

  • Building and strengthening relationships
  • Identifying blockers and providing support
  • Ongoing realignment around priorities

Making your one-on-ones worth having means keeping each of these goals in mind well before any meetings begin.

Here are some tips for how to approach three common one-on-one meeting types:

Remote one-on-one meetings

Working remotely can make one-on-ones more challenging. Without the in-person element, building rapport and being present usually means being on video.

But as things like Zoom fatigue become more prevalent, the most empathic leaders give their remote reports more flexibility.

Instead of unofficially requiring remote staff to appear on video, consider making it clear that voice or screenshare-only catchups are not only okay, but encouraged.

Many people find it easier to focus on what they’re saying—and not so much on how they look or what’s happening in the background—when they’re not forced to appear on camera.

And according to several experts, meeting without video is likely to produce better discussions.

Here’s a meeting template for your next remote one-on-one:

Warm up

Start with a light, open-ended question. What’s been keeping you busy?

Highlight Achievements

What milestones have we hit since our last check-in? Note progress on important initiatives and emphasize takeaways.

Problem Solving

What’s stopping you from being more productive? How can management help you be more productive? 

Plan to remove specific inefficiencies or roadblocks. Create action items.

Two-Way Evaluation and Feedback

What are we doing well? What can we do better? Discuss ways to create value for manager, employee, and the organization.

Open Discussion

Provide space for open discussion. What’s got you excited? Worried? Annoyed?

Follow-Up

When is our next one-on-one check-in? Summarize any action items arising from the one-on-one.

Action items:


Goal-setting one-on-ones

Goal setting meetings are a great way to lend a personal touch to quarterly planning efforts.

But there’s one thing that limits the potential of this type of one-on-one meeting. Often, new managers and seasoned leaders alike forget that their direct reports don’t work purely for the enjoyment of helping the company meet its goals.

Each member of your team is likely to have professional needs of their own. Good leaders make it comfortable for their direct reports to talk freely about their aspirations. Exceptional leaders find ways to relate individual goals to organizational goals.

In practice, this means working collaboratively to determine how each team member can contribute to the company in ways that advance them professionally.

It may not always be possible, but when a leader knows his or her team members well, it’s much easier to identify these opportunities.

Here’s a meeting template for your next goal-setting one-on-one.

Big Picture

Where do you see your career going in the short/long-term? 

Career Growth — Organizational Mandates Alignment 

Where do the organization’s mandates most closely align with your career goals? Discuss how [the direct report’s] job function fits into organizational goals.

Goal-Setting Part 1 - Aspirational

Brainstorm measurable, meaningful short and long-term career goals

Goal-Setting Part 2 - Actionable

Brainstorm measurable, meaningful short and long-term goals to create stepping stones towards achieving specific organizational mandates.

Follow-Up

Do we need solo time to build on this? Should we review our goals again? When will we connect again to measure progress? 

Skip-level one-on-ones

A skip-level meeting pairs non-managers and individual contributors with their manager’s manager. 

  • A content marketer meeting with the VP of marketing
  • An account executive meeting with the VP of sales
  • A customer service rep meeting with the VP of customer success

While skip-level meetings should never serve as a replacement for meeting with an immediate supervisor, this one-on-one can significantly benefit each participant by breaking hierarchical siloes.

Managers who manage other managers without skip-level meetings might rely too much on the opinions of their direct reports—or worse, become completely out of touch with what’s happening “on the ground.”

Skip-level meetings enable them to connect directly with these team members to gain a broader perspective of team performance and individual morale.

This benefit works both ways. For the non-manager, a skip-level meeting allows them the opportunity to refine or expand their perspective around daily work activities since their manager’s manager can likely provide more insights about the company’s high-level business goals and strategy.

Unfortunately, skip-level meetings often suffer from a supreme power imbalance. When VPs and other execs treat these meetings too informally, they don’t benefit anyone. Don’t be one of those guys.

Here’s a skip-level one-on-one meeting template by Michael Brown, Regional General Manager at Uber for you to use:

Attendees

A skip one-on-one meeting is a meeting with managers or senior leaders in the company with those who are in junior positions. It is important not to have the meeting with a direct report in order to get honest and accurate feedback. To be truly effective you must create an environment in which the employee feels comfortable. Ideally, the manager should have a relationship with the individual being interviewed. Remember these sessions are about listening and learning from different perspectives in the organizations. 

Preparation

Managers should come armed with questions about the business based on data they’ve reviewed in advance — both qualitative and quantitative. 

Here are some questions you might want to ask in your one-on-ones:  

  • What is the morale in the office from their point of view?
  • How they are feeling about his or her team?
  • What their manager is doing well and not well?
  • What obstacles are they facing in their job? (If you are their skip-level manager, take steps to unblock these obstacles — it will mean a lot to the person that you took action.)
  • Do you understand the company’s goals and how your team’s goals fit into that picture?
  • Do you feel like you can do things you believe are right for the business?
  • Do you think leadership acts consistently with your values?
  • What would make work better for you?
  • When was the last time you took a vacation?
  • What is your sacred space? Do you feel like you have time for it?

Open Forum

  • Ask the interviewee if there is anything that was not covered above that they would like to add?


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Rob Lennon
Customer Education Lead at Hugo
Marketer and author with experience spanning a diverse 16 years in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

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